On a chilly October morning, high above Yosemite Valley, four men stood atop El Cap after climbing the hardest rock climb in the world. Each was an acclaimed climber, with notable first ascents to his credit. Each had already made their mark on American climbing, and each would go on to even harder and more daring ascents in their long and storied careers.

But for ten days in October 1964, they climbed together as partners, venturing into unknown and untraveled terrain with no expectation of help or rescue, wholly dependent on their relationship with each other and the skill they each brought to the task ahead.  When Royal Robbins, Chuck Pratt, Tom Frost and Yvon Chouinard made the first ascent of the North America Wall on El Cap, it ushered in a new era of American excellence, proving to everyone that these climbers were the best in the world.

Royal Robbins was the leader of the group and organized the North America Wall ascent.  One of the original Yosemite hardmen of his generation, Royal was the dominant figure in American climbing throughout the 1960s, equally adept at hard free climbing, difficult aid, and mixed alpine terrain.  He would go on to join the top American Guides of his generation at John Harlin’s ISM in Leysin, and then established his own climbing school in Modesto, California in the 1970s.  His iconic status enabled him to enter the outdoor clothing business in 1979 with his beloved wife and climbing partner, Liz, founding a brand that survives today.

As a child, Royal’s instruction manual Advanced Rockcraft was my bible.  When Royal and Liz owned a condo in Beaver Creek in the early 1990s, I had the opportunity to open a great bottle of Barolo with them at our favorite Italian restaurant.  Royal died in 2017 at his home in Modesto, CA.

Chuck Pratt was the best free climber in the group, and his early ascents of technical Yosemite cracks set the world standard in the early 1960s.  He joined Royal, Tom and Joe Fitschen for the second ascent of The Nose of El Cap in 1960 and made the landmark first ascent with Royal and Tom of the Salathe Wall in 1961.  That same year he established The Crack of Doom on Elephant Rock in Yosemite, a fearsome two pitch off width that was among America’s first 5.10s - it routinely spits out expert climbers to this day.

Chuck was also one of the finest mountain guides of his generation and spent most of his career with Exum Guides in the Tetons.  He spent his winters in Thailand with a wife and family, a part of his life no one knew about until after his death in 2000.

Tom Frost was the group’s anchor, an even-tempered expert on all types of rock and a frequent partner on Robbins’ cutting-edge exploits.  He was also the best educated of the bunch, with a mechanical engineering degree from Stanford, and was Chouinard’s partner and co-founder of their climbing equipment business in 1966.  He climbed hard into the 1980s when he moved to Boulder to establish his business, Chimera Lighting , the dominant worldwide brand in studio softboxes.

Tom was my neighbor in Boulder for many years.  Though we didn’t climb together, I recall a walk with him across Dakota Ridge in the late 1980s where I wanted to know about his attempts to preserve Camp 4 in Yosemite and he wanted to ask me about recent advances in optical processing and biotechnology.  He also pointed out some obscure boulder problems I thought I’d climbed first – he assured me that Dave Rearick , another Boulder neighbor and legendary California climber, had sent them all in the 1960s.  Tom died in 2018 at age 82.

Yvon Chouinard was the team’s equal in climbing prowess and hard first ascents in Yosemite. He made the first ascent of the Muir Wall on El Cap with TM Herbert in 1965, a route that Royal later soloed.  A genius at tool building, Yvon was the most successful of his teammates in business.  Chouinard Equipment, which became Black Diamond , and Patagonia are his legacies, and these two companies revolutionized all aspects of rock and ice climbing with Chouinard’s visionary advances in technology.

Yvon invented the curved ice axe, which changed the game in hard ice climbing in the 1970s – he then wrote the book to teach us all how it’s done .  I ordered a Chouinard ash piolet in 1978 after my first season flailing on Northeast ice and carried it with me throughout the 1980s, from the Alps to K2 to the Cordillera Blanca.  It now proudly hangs on the wall of my study at home, its shape a constant reminder of Yvon’s genius and its impact on my life.

Cisco’s stock price topped out in March at $80, we got our free trading shares on May 9 at $64 and distributed them on May 11.  Matt and I promptly sold every share we owned.  Along with the rest of the dotcom bubble, Cisco cratered that summer and bottomed out in October 2002 at $8 per share, a 90% decline from its high in March, 2000.

Cisco was a great American technology company then and remains so today.  As of June, 2026, Cisco trades at $130 per share.  If Matt and I had held onto our Cisco shares instead of selling them, we’d be 2X in 26 years.  There was nothing wrong with Cisco’s business in 2000, it was just way overvalued by enthusiastic stock market investors.

This summer, we’re witnessing the next great stock market bubble.  Three private companies, SpaceX , Anthropic , and OpenAI , are together preparing to sell more than $200 billion of stock to the public in what would be the three largest tech IPOs in history.  All three are growing revenues fast and all three are dramatically unprofitable.  An interconnected industry of chip companies, datacenter providers, private credit funds, and software companies are dependent on SpaceX, Anthropic and OpenAI raising the capital they need to spend with these vendors to enable the build out of their AI infrastructure.

No one is more anxious for these liquidity events than the VCs that backed SpaceX, Anthropic, and OpenAI - a large portion of all venture capital portfolio markups are in these three deals!  You can bet these same firms raised as much money as they could pitching their special access to these AI companies. Now it’s nail-biter time at these VC firms, all of them hoping to get their liquid public shares into the hands of investors before the reggae music stops. 

In my opinion, OpenAI is the most likely of the three to crater.  Its CEO, Sam Altman, has proven himself a skilled promoter and ruthless startup operator in one of the most competitive business environments in the world, Silicon Valley.  He is good at Mafia .  But none of his experiences as an entrepreneur or VC has prepared him to lead a large, fast-growing organization at the cutting edge of a new technology revolution.  Compared to the loyal, cohesive teams at SpaceX and Anthropic, there’s been a lot of management turnover and Board turmoil at OpenAI.

I love the product from OpenAI and Anthropic, happily pay a monthly subscription for both, and use them every day in my work and in my life.  I didn’t use them to write this post, but I did use them both to check for accuracy and I find it valuable to have two different AIs to compare against each other.  It’s not clear to me that either model is better than Google, who also just raised $85 billion in cash from a stock sale to ensure that it doesn’t run out of money competing against Anthropic and OpenAI.  No matter how good its product, I wouldn’t want to bet OpenAI’s success on outspending Google.

Big new technology markets invite lots of competition, and the top AI models are already being challenged by less expensive, opensource versions from China.  Many large enterprise customers are using OpenAI and Anthropic to automate their business processes but so far are seeing less value and slower progress than forecasted.  Just like in the internet bubble, those gains will come, it’ll just take more time than people expect.

All these trends point to valuation.  OpenAI already faces challenges in management, governance, access to capital, and competition.  Its last round of venture capital in 2026 valued OpenAI at 36 times revenue, the same as Cisco in the spring of 2000.  Here at the top of the AI Bubble, this summer’s OpenAI IPO will try and price its shares at a sales multiple higher than that. 

What if OpenAI craters? At Boulder Ventures, we hope to remain outside the blast radius. That means backing serial entrepreneurs who can navigate the market when the dust settles, regardless of which frontier model is writing their code.

Celestial Seasonings was the anchor tenant in the history of Boulder’s natural foods industry.  It was started by Mo Seigel and John Hays, two stoner hippies who gathered herbs and mushrooms in the hills above Boulder in the 1970s and made tea, among other things.  But Celestial didn’t become a company until Barney Feinblum took over as CEO in 1986 and led its buyout from Kraft in 1988.

Barney didn’t want to work at Celestial, but his wife Jules loved herbs and convinced him that it would be cool.  Barney was an original investor in Merc Mercure’s and my fund, Colorado Venture Management (CVM), and we were investors in Alfalfa’s , Hass Hassan and Mark Retzloff’s organic grocery store chain, where Barney was Chairman.

After he sold Celestial Seasonings a couple times, Barney took over as CEO of Horizon Organic Dairy , the first national organic milk brand in the US.  Barney didn’t start that either – Retzloff and Paul Repetto did with Mark Peperzak, a renowned dairyman.  But Horizon didn’t become a company until Barney Feinblum took over as CEO in 1996.  By then, Barney was a founding investor in my new fund, Boulder Ventures, and I knew what to do.

Barney and I raised two rounds of equity for Horizon Organic Dairy and took it public in 1998.  HCOW got to $100 million in revenues faster than any natural foods company ever had at the time, and Barney sold it to Dean Foods in 2004.  That was a great deal for Boulder Ventures I & II.

Around that time, Hass and Barney merged Alfalfa’s with another organic chain in Boulder called Wild Oats and took that public in 1996, a good deal for our CVM funds.  Part of that deal was that Hass and Barney wouldn’t start another organic grocery store in the US for a few years. 

So Hass went to London where he’d grown up and started the first chain of organic grocery stores in England called Fresh & Wild .  Barney and I financed Fresh & Wild with some fancy London investors, and Hass grew the chain to seven stores before we sold it to Whole Foods in 2004 for equity.  Whole Foods under John Mackey was a great stock and Fresh & Wild was a great deal for Boulder Ventures III.

Along the way Barney was the key investor or Chairman in a bunch of other successful natural foods companies that I wasn’t involved in but wish I had been, like Izze Beverage which got bought by Pepsi, and Seventh Generation which got bought by Unilever.  Today, Barney and I are backing Hass again in a chain of fresh markets in San Francisco called Luke’s Local.   Luke Oppenheim, the founder, worked at Colgate Palmolive after their acquisition of Tom’s of Maine (a Barney deal), the first organic toothpaste brand founded by Tom Chapelle.

This history serves to make a point about an American industry that started with Celestial Seasonings in Boulder:  all of it owes its existence directly or indirectly to Barney Feinblum, the greatest serial entrepreneur in the natural foods business.

Barney went to Cornell and supported its herb garden for many years. He and Jules decided that Colorado needed its own herb garden and endowed a new one at Colorado State University.   Cindy and I went to the dedication and groundbreaking last week, where Jared Polis, another great serial entrepreneur from Boulder and now our Governor, introduced Barney to the assembled dignitaries.

Referencing Celestial Seasonings, Barney said something profound: “You can change the world with a few small plants”.

When Guides fall, their passing echoes through the valley. 

Dick Jackson died peacefully at home the day before Thanksgiving, and within hours, everyone in the Roaring Fork had heard the news.  Within a day, Guides around the world knew that one of America’s greatest Mountain Guides had fallen.

When I was an aspirant guide in Chamonix in the early 1980s, Dick Jackson is who we all aspired to be: cool, competent, highly skilled on rock and on skis.  He was popular with both fellow Guides and admiring lady clients. 

Dick’s relationships with the leading European Guides enabled the AMGA to enter the IFMGA system in 1997. It was Dick’s leadership of the AMGA Board over the following decade that allowed us to drag the AMGA kicking and screaming into becoming a full IFMGA country.

Dick was a role model to young guides, and he exerted a profound influence on our culture.  Today, there are 191 IFMGA Guides in the USA, all certified to the international standard by the AMGA, all of whom stand on the shoulders of Dick Jackson and his stewardship of American mountain guiding.

Over the past three decades, Dick Jackson and I skied and climbed together all the time, all over the world, on his terrain and mine. We loved every minute of it and we loved each other. We represented the AMGA together at IFMGA meetings, and some of my best trips with Dick were to these events, where we ate and drank and skied and climbed with the head Guides of all the member countries.

My favorite memory of these was our visit to the Japan IFMGA meeting in 2007 where we climbed Mt. Fuji together in full winter conditions.  At that meeting, Dick and I proposed to host the 2010 IFMGA meeting in Boulder, and to our astonishment, the IFMGA Board agreed.

There was no prouder moment in Dick’s life than when he led the Guides Parade down Pearl Street at the front of the AMGA delegation with his daughter, Tashi holding the American Flag.

Dick Jackson was my friend, my mentor, my hero, and my fellow Mountain Guide for more than thirty years.  May his memory be a blessing to us all.

When I was a young aspirant guide in the 1980’s, I noticed that many older Guides in Chamonix skied on wooden skis.  I was quite proud of my high-tech touring setup then, a pair of Fischer Air Carbons purchased at great expense from Snell Sports .  Why would anyone revert to retro wood when new technology was faster, lighter and stronger?

My neighbor in Les Houches, Roland Ravanel, explained that wood skis translate force into your ankles, knees and hips in a more gentle way than metal skis, an appealing feature for aging Guides whose bodies contain a lifetime of tours.  I learned that the tradition of wood ski making in Chamonix dated back centuries and that the best craftsmen had always been sought after by Guides and Clients alike. 

I first heard about Peter Stelzner and Rabbit on the Roof when he established his shop in an old mill site on the outskirts of Chamonix in 2010.  It shared space with Stevie’s friend Andy Parkin, a renowned British alpinist and artist.  Word spread throughout the Vallee that Peter’s skis were the best, and soon the waitlist for a pair of his custom, handmade boards grew longer.

After much effort and a few good glasses of wine, I finally made it on the ROTR list for my own pair in 2015 and put down a deposit.  The next year, a fire in the mill destroyed Peter’s workshop and all his inventory.  Like many of his devoted clientele, I then paid Peter in full for my skis, in hopes he would someday resurrect his shop and fill the order.

Incredibly, Peter made them in the burned-out shop along with a couple others and used the emblems from his charred inventory to adorn my new skis.  He delivered them to me on a summer trip to Chamonix for my 60th birthday.

I love the skis that Peter made for me, and I ski on them almost every day.  They’re not light or fast turning, but they translate force into joy.  They are mounted with Marker Kingpins so that I can tour with them or ski on the piste.  After many seasons, I know their sweet spot:  whether on fresh groomers or untracked powder, my wood skis evoke flow and pleasure unlike anything I’ve ever had.  At the end of each season, I smooth out the nicks with fine sandpaper and apply tung oil to make them good as new. 

With the help of his partner, Anati and some strong Chamonix locals, Peter rebuilt his shop and re-established his business in its former location.  Rabbit on the Roof is a story of resilience and community, all based on one man’s mastery of his craft – themes that resonate with us across the many serial entrepreneurs we’ve backed at Boulder Ventures.

That story has now been made into an award-wining documentary by the Chamonix-based cinematographer, Pierre Cadot. It’s called Les Moulins des Artistes:

By Steve House There is a kind of quiet courage that does not get much attention.

It is not the kind expressed in triumphant summit photos. It is not loud. It is not flashy. It does not raise it’s arms at the top. It continues. It holds steady. It endures.

Enduring courage is what Kyle Lefkoff lives by.

I met Kyle through the mountain guiding world. But it was during this conversation that I began to understand how deeply the mountains shaped his view of everything he cares about: climbing, capital, mentorship, time, and place.

He grew up as an outsider. A Jewish kid in the 1960s Deep South. He was intense and curious in a world that often rejected both. He found relief in two contrasting places: books and the granite of Stone Mountain. As he taught himself climbing from Royal Robbin’s classic:, Advanced Rockcraft , the racist owners of Stone Mountain drilled and chiseled to create a memorial to the leaders of the Confederacy. Kyle named his final climb there “The Three Losers” in reference to the figures hewn into the mountain, and soon thereafter, climbing at Stone Mountain was banned entirely.

Bearing witness to others of contrasting values, the experience of falling in love with climbing, and that sadness of loss of climbing at Stone Mountain untethered him. And as he came into manhood, he awakened to the fact that Atlanta, Georgia, would not make space for who he was. So he left. He went west. He found Boulder, Colorado.

Boulder was not the biggest opportunity for the precocious University of Chicago business school graduate. But it was the only place where he could be both a serious climber and a serious venture capitalist. He did not want to choose between them. He wanted to live both lives fully. That decision shaped everything that followed.

He joined the 1986 American expedition to K2 . That season became one of the deadliest in the history of mountaineering. Kyle was there. He had a front row seat to the discussions and decisions that brought everyone on his team home alive. And it changed the way he approached risk in every part of his life. He stopped thinking about outcomes as destinations, and he started thinking about getting everyone home. The journey home passed through the outcome, the point of success as they defined it. Coming home meant starting it all again, pushing the flywheel faster by applying more high-performance human capital and more capital of the classic kind. Starting companies, investing in companies, building companies and selling them was not a linear path but a circle, a cycle. A cycle that created successes and failures, but most importantly, it created momentum.

He built Boulder Ventures in this spirit. His guiding lights were: Patient capital, long-term partnerships, and authentic relationships formed through shared effort. He stayed with Array BioPharma for twenty years. He helped it grow, stumble, recover, and finally succeed. He never left. He saw it through.

Eventually, there was enough human and financial capital to create the American Institute for Avalanche Research and Education (AIARE), a gift to the climbing and skiing community. That alone will shape and save numerous lives long after he is gone. That is where momentum creates a legacy bigger than any one man.

As we spoke, Kyle kept returning to one idea: where matters. Not just in a geographic sense, but in a personal sense, the places we choose shape us. And the commitment we make to those places determines what we can build. At the end of our conversation, I asked him if the 15-year-old Kyle could know everything that the 65-year-old Kyle now knows, what he would do differently. His answer, I’m sure you’ll agree, is truly astonishing.

I have come to believe that his true gift is not his success in either climbing, guiding, or venture capital. His gift is integration. Kyle chose a terrain and a community of people that entirely fit who he is. And he stayed with it. He built within it. He invited others into it.

He never left his mountain.

The rope is still not on the ground.

And Kyle Lefkoff is still climbing.

Listen to the full podcast here: The Geography of Risk

Bernese Mountain Dogs are spirit animals for Mountain Guides.  The breed first appeared two thousand years ago as the Roman Legions crossed the Alps with their mastiffs and bred them with local mountain dogs.  The Walsers moved from the Valais into the high mountain meadows across the Alps in the 13th century and bred their Sennenhunds for three missions:  pulling sleds, guarding livestock, and snuggling with their families during the long winter.

The Walsers also invented ski touring and climbing in the Alps and were the first mountain guides for visiting tourists in the 18th century.  Their Berners went with them everywhere and became adept in alpine terrain in all conditions.  With the advent of mechanized farming and modern transportation, the breed almost became extinct at the end of the 19th century, but were saved by Albert Heim , a famous Swiss geologist and dog breeder who popularized the Bernese Mountain Dogs among Swiss households in the early 1900s.  They made it to America in 1926.

Revelstoke the Berner was a COVID puppy who came to us from his breeder in California in the darkest week of the pandemic.  He was the third of our family’s line of Bernese Mountain Dogs and had the biggest personality of them all – he let you know exactly what was on his mind.

Revy loved to ski and climb with his family and was trained in the field with impeccable manners on the Snowcat or at the Crag.  In his brief life in the mountains, he encountered Bear, Moose and Elk and never backed down. 

One of the hardest and most rewarding things we do in life is building bridges.  Bridges are expensive and often controversial. Their span is a complex combination of engineering and art.  Their installation requires competence, planning, and coordination among a variety of interested parties over years of effort.  Once completed, bridges must be maintained for generations.

Even under the best conditions, a small number of loud voices will always oppose building bridges, and their opposition can thwart even the best ideas.  The most successful bridge builders have lots of other things to do and do not need the public scrutiny and headaches that often accompany these projects.  But these same individuals are not easily distracted by background noise in pursuit of a worthy goal.

Eldorado Canyon State Park outside Boulder is among the finest traditional rock-climbing areas in the world.  Eldo is a reason why many of us choose to live and work in Boulder, and its colorful sandstone walls and complex movement challenge the best trad climbers.  Rich with history, Eldo climbing is more like a ritual than a sport. In season, my fellow Eldo aficionados and I go climbing there almost every day.

The West Ridge is a fantastic section of the cliff and by itself would be one of the best climbing areas around.  The steep trail at its base was only accessible from the road via a technical and dangerous scramble across the slab above South Boulder Creek, or an even more dangerous traverse across the river in high water or on slippery rocks – both approaches have been the scene of many accidents over the years among climbers and hikers.

The sensitive riparian habitats on the banks of South Boulder Creek were disrupted each season by hundreds of climbers thrashing across the reeds to access the West Ridge trail. 

When there is a climbing accident on the West Ridge, rescuers had to rig a complex Tyrolean traverse across the river to rescue the injured party, adding hours to the rescue scenario.

In fact, the reasons for a West Ridge Bridge – climber access, improved riparian habitat, rescue safety – are all so obvious and so good that it’s astonishing that it hadn’t happened yet.  But inertia, money, and a small, vocal group of local climbers opposed to safe access kept the bridge from being built.

That changed in 2023 when a group of us conspired to create a public/private partnership to build a bridge under the leadership of Mike McHugh. 

McHugh is a special character in the history of Eldo.  For the past twenty-five years, he’s been the principal architect of the complex network of access trails that anchor the steep scree slopes below Eldo’s cliffs.  These trails take years to build and are each a work of masonry art that serve to both stabilize loose slopes and provide a landing zone for Eldo climbers about to begin their ascent.  During the Boulder Floods of 2013 , McHugh’s trails held Eldo together and prevented the Park’s ruin, a fact not lost on Colorado’s land managers. 

Since the Flood, McHugh and his team of builders have been busy updating and stabilizing Eldo’s access trails using public and private money.  The West Ridge Bridge is the cornerstone for McHugh’s visionary trail network on the east side of South Boulder Creek, and its design and implementation is a testament to his skill and experience in Eldo.  We formed a group to support Mike in this effort and raised money from private donors and the Land and Water Conservation Fund , a grant source that has been supporting the building of trails and bicycle paths in Colorado since 1965.

The new West Ridge Bridge was installed on August 26, 2025, and dedicated to the public on October 16, 2025, in a ceremony attended by Eldo’s land managers, neighbors and climbers.

Then we walked across the bridge we all built and went climbing on the West Ridge.

Our breakthrough came from commitment, progression, and a strong partner. My Colorado College classmate, Dr. Joe Forrester, is a highly skilled aid climber and the head of Trauma Surgery at Stanford Medical Center. Joe and I built our partnership over the years through progressively difficult aid climbs in Yosemite, like Ten Days After (2023) and Laughing at the Void (2024). Staring up at the Shield Roof, we knew that once we moved onto the upper headwall, the easiest way down was to go to the top.

Facing 100-degree temperatures, we wondered whether we had enough water or whether we were tempting a rescue situation due to heat exhaustion. We bet that cooler temperatures in the forecast would reward our commitment, and we finished The Shield in four days, three nights, a couple days faster than our time estimate.

Whether on the wall or in the trenches of a startup, breakthroughs result from preparation and discipline born from prior setbacks and learnings.

When my friend Sam Dryden was a senior advisor to the Gates Foundation, he once told me a story:  after he was President, Jimmy Carter went on a personal mission to eradicate the Guinea Worm , a terrible parasite in West Africa that infected millions of children.  It was easy to cure kids of the Guinea worm – just teach them not to drink the dirty water where the parasites live. 

The problem was that in all these African villages, there was a Witchdoctor who made a living selling some useless tribal remedy to the local families.  Curing the Guinea Worm with education threatened the Witchdoctor’s business, and they fought President Carter and his colleagues everywhere they went.

Witchdoctors aren’t stupid – they’re evil.  They know the snake oil they sell people doesn’t work and isn’t the cure for their misery, but they have a vested economic interest in preserving suffering. 

At Boulder Ventures, we invest in enterprise software and pharmaceutical startups, and everywhere we go, we find Witchdoctors.

Whenever we fund a new company whose product cures disease or solves a big problem, we encounter Witchdoctors who make a living convincing people that this is a pain they should endure as a natural part of their lives.  Our companies then spend a lot of time and money explaining why that’s not true and that our solution is safer, simpler, and better for them. 

Witchdoctors are powerful leaders in their communities, especially if they’ve been selling poison successfully for a long time.  As a result, most people would rather eat more poison than solve the problem.

Change is hard, and when there’s a new drug or a platform shift that threatens their economic model, the power of the Witchdoctors to resist change is strong.  But in the end, Witchdoctors always lose.

In 1986 there were 3.5 million cases of Guinea Worm in West Africa.  In 2023 there were 14.

Jimmy won.

In every valley of the alpine regions on Earth, there is a distinctive culture – it’s one reason why these places are marvelous to visit.  After a guided trip, Clients can accurately describe the differences between the cultures in the Val Gardena and Arco, or between Aspen and Telluride.  Mountain Guides embody the culture of their valley.  They are responsible for curating it for clients and for maintaining it for the next generation of Guides.

Culture in these valleys evolves over time, the result of the people, cuisine, and mountain topography that combine to give each its distinctive flavor, a lifestyle unique to that place.  Some are born there, but every Guide finds his Valley and becomes a part of its culture over the course of his career.

Venture Capitalists help create the culture of their valleys as well, whether it’s a place like San Francisco, or a market like biotechnology.  Over time, a few VC Firms dominate their valley by investing in the most successful companies and gathering the most assets to invest, but because the goal of these professional relationships is money and status, it’s harder to define the culture of a VC Valley and how it differs from one place to another.

Over the past thirty years at Boulder Ventures, we’ve developed a culture in the Boulder Valley that’s modeled more on Mountain Guiding than on Venture Capital.  As a result, we’ve formed authentic relationships with entrepreneurs and investors that have endured for decades.  We point to that culture in working with aspirant entrepreneurs and VCs. In turn, they embrace our lessons and our best practices around risk management in the mountains and in business.

We believe that Culture is the only sustainable advantage in the venture capital business. The Culture of Boulder Ventures is what makes guiding so enjoyable for us all.

Ken and Patti Ferrin taught me to heliski.

I was already an aspirant ski guide and a decent powder skier when I first met them on the way to the Adamants in 1992, but I’d only been on five or six CMH trips and I didn’t yet understand the nuance of the lodge culture. Ken and Patti embodied the ethos of people that shaped their lives around heliskiing in the Columbia Mountains of Canada, and I had a lot to learn from them.

Ken Ferrin graduated from UCLA with a Ph.D. in Math too early to get drafted for Vietnam.  Instead, he went to Wall Street and programmed the first computers in the 1960s to arbitrage bond prices. It sounded like science fiction to people back then, but Ken did it successfully and sold his company to JPMorgan for a lot of money. At that point, he was a conventional Wall Street guy: wealthy, married, couple of kids, living in the burbs.

After he sold his business, Ken was rich but unhappy, a bad combination for someone with a strong sense of adventure. He left his wife, went to Capri to have fun, met Patti there playing tennis and fell in love. Ken and Patti wanted to learn to ski together, and moved to Aspen, where they became experts over a couple of seasons. Then Ken and Patti went on a heliski trip with CMH and decided that’s what they wanted to do together for the rest of their lives.

I was confused when I met Ken and Patti in 1992.

I wanted to be a venture capitalist, but I also wanted to be a mountain guide. Ken told me that money is like gasoline on a road trip: you don’t want to run out, but the point of life isn’t to go on a tour of gas stations. He convinced me I could do both.

Ken and Patti invited me on their CMH team and taught me how to act like a good guide and a good client on a heliski tour. I skied with them a couple times a year, but always at Christmas at Galena with an incredible group, all of whom became our lifelong friends.

I don’t have much time left in the mountains.  I’ve skied and climbed more than 150 days each year since I moved to Colorado in 1985.  After forty years here, there’s another 1,000 days for me if I’m lucky, hundreds if I’m not.

Each time I touch rock now is a gift, each powder day a blessing.  You’d think after all this time I’d get bored and tired of this stuff.  Instead, I’m filled with the same burning desire to climb each morning the sun shines in Boulder.  I wake up vibrating in Vail on a powder day.  The joy of movement in my terrain, my connection to these places, my confidence in guiding clients – there’s no turning down the volume of this music and I’ll keep dancing as long as I can.

Peter once told me that he wanted to become a venture capitalist because it’s a job he could do his whole life.  There was a beginning – we both started out as VCs as soon as we graduated business school – but there’s no end to our careers.  We’re as motivated and focused now as we’ve ever been.  What we know about investing in startups is priceless and cannot be duplicated.  The wheels of ambition won’t stop grinding and there’s always a crop of youngsters willing to try their hand at the game, but few of them will succeed and they will all learn the same expensive lessons we did.

Skiers live for bluebird powder days with our family and friends. But not every day is perfect and what makes us true skiers is not how we perform when conditions are favorable, but when things kinda suck.

No one understood this better than the Mountain Guide and Icon of extreme skiing, Doug Coombs. Doug grew up in New England learning to ski in rugged conditions at Vermont and New Hampshire resorts before migrating west to Jackson Hole. In the early 1980’s, he skied and guided most of the big lines in the Tetons, before Patrol famously kicked him off the hill for ignoring their ropes.  Coombs then moved to Valdez, Alaska, where he pioneered heliskiing in the Chugach Mountains through the 90s.   Until his death in La Grave, France in 2006, Coombs was the premier steep skier of his generation.

According to Coombs "there are no bad ski conditions, only bad skiers."

In teaching our children how to ski, "Coombs Law" became a family mantra. Learning to accept and excel at skiing hard pack, wind crust, exposed rocks, icy slopes, breakable crust, shallow base and all the other sub-optimal conditions is something we all strive for. We learn to focus on the things we can control (effort, attitude, toughness, practice, ability, fitness and preparation), rather than worrying about things we cannot.

Venture capitalists must be comfortable in all conditions as well. We don't control interest rates, regulatory environments, politics, valuation excesses, and other macro effects. But we get to choose the serial entrepreneurs we back, the markets we invest in, and the problems we elect to solve for. If we are right about the market and right about the people, we usually make money even in choppy conditions.

At Boulder Ventures, we have a thirty-year track record of generating distributions to our investors in all kinds of markets. This distinguishes us from many of our peers.

Coombs’ Law.

“In the first half of the 20th century, despite pervasive and continuing social discrimination against Jews throughout the Western world, despite the retraction of legal rights, and despite the Holocaust, Jews won 14 percent of Nobel Prizes in literature, chemistry, physics, and medicine/physiology.  In the second half of the 20th century, when Nobel Prizes began to be awarded to people from all over the world, that figure rose to 29 percent. So far, in the 21st century, it has been 32 percent. Jews constitute about two-tenths of one percent of the world’s population. You do the math”.  - Charles Murray

Throughout modern history, Educated Jews have exerted a pervasive, positive influence on our civilization.  Wherever we are, our economic and cultural success elevates the societies we live in . Jews are a litmus test for democracy.  In contrast and in every case, places that murder and drive away their Jews are neither free nor successful.

The underlying cause of Jewish exceptionalism is our culture of learning – all Jews are obsessed with the education of their children, especially Ashkenazim.  At my oldest son’s Bar Mitzvah, here was my benediction to him :

  Our God, the God of Abraham and Sarah, did not give us a Cross, or a Sword, or a Statue to worship.

 God gave us a book.

 Both of your parents went to college and to graduate school – we are Educated Jews.

Your Mother’s Father went to Medical School and became a renowned heart surgeon.

My Father went to Law School and ran his own law firm for more than forty years.

My Mother got her Doctorate in Political Science and has helped whole nations heal their conflicts.

Your Mother’s Mother got her master’s degree in special education, and my Stepmother went to college and worked for Planned Parenthood in Atlanta– they are ALL Educated Jews.

 This gift from God, the Torah, has been given to generations before you so that they too can be Educated Jews. And now this gift has been given to you. 

There’s a raging debate among academic geneticists over whether the exceptional intelligence of Ashkenazi Jews is primarily inherited or a result of the Jewish culture of learning .  I find this debate tedious:  my children enjoy both.  They benefit from the genetic legacy of generations of Educated Jews marrying each other, and from the intellectual challenge of growing up in a household where learning is the focus. 

My sons are privileged, but that privilege doesn’t come from the money I’ve made in business or our social status in Boulder.  It comes from having two loving Jewish parents who read to them every night of their lives until they could read to us. It comes from an unrelenting focus on their intellectual development.  It comes from growing up in a house and in a community filled with Educated Jews.

I grew up in Atlanta in the 60’s and 70’s surrounded by antisemitism – it was the background noise of my childhood.  My father was a corporate lawyer by trade, but he and his law partners had a penchant for social justice in the racist South and devoted their pro bono efforts to the cause of civil rights for Black people.  Joe Lefkoff bailed Rev. Martin Luther King out of Fulton County Jail on one occasion, and on another, argued Grey v. Sanders before the US Supreme Court, ending the County Unit System in Georgia and insuring that one man, one vote was the law.  Our redneck Atlanta neighbors hated him for this activism, hated us for being Jews, and let us know it every chance they could.

When I came to climb at age 16, Boulder was the first place I’d ever been where no one gave a shit about any of this.  The only thing people here cared about was whether you could get a rope to the top of the cliff, make a decent powder turn, or ride your bike down the singletrack.  It was an epiphany for me, and I’ve loved Boulder for it ever since.  We’ve raised our sons in this bubble, teaching them to climb and ski with all the benefits of Jewish nature and nurture. 

Like my wife and me, my boys went East to college for their education, my older son in computer science and engineering and my youngest in biomedical sciences.  While both my boys have experienced antisemitism in their lives, it reached a crescendo for them in 2024.

This year, they’ve seen angry mobs of fellow students chanting antisemitic slogans on campus, calling for the death of Jews.  My father, who died last summer, would have been appalled to witness the progressive children of his liberal colleagues spewing Jew Hate from the lawns of the elite universities to which they were admitted.

In contrast, I’m happy to watch my sons experience real antisemitism firsthand.  Jew Hate is now and always has been a direct consequence of our success, a reminder that the influence Jews wield in a free society can never be taken for granted.  In this season of antisemitic campus vitriol, I’m grateful that my sons have connected to their Jewish roots with renewed passion and committed themselves to advance our American society as Educated Jews.

Mazel Tov to Jonah Lefkoff, Northeastern University Class of 2026, and to Asher Lefkoff, Tufts University Class of 2028!

In the spring of 1966, the three greatest American climbers of their generation approached the final pitch of the Eiger Direct North Face.  John Harlin , Layton Kor and Royal Robbins knew that their bold ascent of Europe’s most famous face would echo across the Continent with a new message:  the Americans were among the best alpinists in the world.

Standing on the summit of the Eiger in the gathering storm, Harlin, Kor and Robbins embraced, then descended the West Ridge to catch the train in the Jungfraujoch, satisfied in their performance.  The party on the deck of the Kleine Scheidegg that night was epic.

Harlin had started an English-speaking guiding service in Leysin, Switzerland, the summer before called the International School of Mountaineering (ISM) and invited Robbins and Kor to join him as guides there.  Over the next three seasons, the Americans became renowned for guiding the hardest routes in the Alps.

Harlin joined his peers from Austria, France, Switzerland, and Italy to establish the International Federation of Mountain Guides Associations (IFMGA), the standard setting body for all the world’s Mountain Guides.  Robbins teamed up with American guides Doug Robinson, Michael Covington, and Gary Hemmings to establish the American Mountain Guides Association (AMGA), which adopted the IFMGA standard and began training US Guides in the international System alongside its European peers.

The professionalism of the international guiding standard influenced Federal land managers in the US, and a system of high mountain huts was established in the Sierras, Rockies and the Alaska Range.  Today, several thousand AMGA Mountain Guides operate from these huts, a testament to the vision of Harlin, Kor and Robbins.  Their ascent of the Eiger Direct was the start of it all…

Unfortunately, that’s not how it happened.

Instead, Harlin snubbed Robbins on the Eiger climb in favor of Stevie’s uncle, legendary British alpinist Dougal Haston .  During one of the multiple attempts at the face, a rope broke as Harlin was ascending to the high point, and he plunged 1000 meters to his death.  Haston carried on to the summit of the Eiger with a competing group of German climbers.  Kor quit the route in sadness and disgust and never seriously climbed in the mountains again. 

Harlin did start ISM the summer before his death and was a highly respected and influential American climber and guide in Switzerland at the time of the IFMGA’s inception. Had his rope held strong, it’s not a stretch to imagine that American guides might have joined the IFMGA in the late 60s.

As it turned out, the AMGA didn’t get its start until 1979 and the organization didn’t join the ranks of IFMGA member countries until 1997, more than thirty years after Harlin’s death on the Eiger Direct.  It’s possible that Harlin’s death caused two entire generations of Americans to lose the chance to become career Mountain Guides at the international standard, including mine.

 It could have been different.

My mentor in the venture business and the Founder of Boulder Ventures, Merc Mercure , prized brevity over all other qualities in our business relationship.  Merc believed that clear, focused communication among partners enabled better decision-making under conditions of uncertainty, and reduced ambiguity amidst the chaos of our startup investments. 

As an aspirant VC, Merc enforced brevity in our daily interactions.  Here’s what that sounded like in a typical conversation:

Kyle:  Merc, I’d like to lead the Series A round for Hauser Chemical Research .

Merc:  What do they do?

Kyle:  They use ethanol column extraction to make active pharmaceutical ingredients from plant substances at scale.

Merc:  Too wordy.  What do they do?

Kyle:  They make Taxol for Bristol Myers Squibb.

Merc:  Is that a good business?

Kyle:  $720,000 per kilo.  BMS ordered 200 kilos.

Merc:  Approved.

Merc was the founder and CEO of Ball Aerospace and believed that every great technology business could be described in two words (Satellite Manufacturing).

Here’s a Merc List of the biggest technology companies today with their two-word descriptions:

Tesla                Electric Cars

nVidia              AI Chips

Apple              Electronic Gadgets

Microsoft         Computer Software

Facebook         Social Networks

Amazon           Online Shopping

Google            Internet Search

Here’s a Merc List of our 10 most successful investments at Boulder Ventures :

Array BioPharma                    Cancer Drugs

ArcherDX                               Cancer Tests

Black Bear Energy                  Commercial Solar

BroadHop                               4G Software

Clarabridge                              Callcenter software

Datavail                                   Database Services

Lefthand Networks                 Ethernet Storage

LineRate                                  Proxy Services

Rally Software                        Developer Tools

Xifin                                        Billing Software

We strive to enforce brevity every day at Boulder Ventures.  Brevity promotes intellectual rigor in our investments and allows for precise communication among the BV partners and our serial entrepreneurs.  It also saves time for more climbing and skiing. 

Merc would approve.

Strategy #1 – Western Zone and BlueSky Basin.

Run #1: Warm-up on Dealer’s Choice - from the top of Gondo One at 8:50am, lift Chair #3 and ski across the top of Game Creek Bowl to the Western ski area boundary. Dealer’s Choice and Lost Boy get groomed almost every night. Dealer’s is a great warm up and you can suss out your group’s skill set on this run. If they can’t ski it top to bottom, leave them there. Lift Chair #7.

Run #2: Game Creek West Aspect – turn left off Chair #7 and traverse around to the East entrance to Game Creek Bowl. This west-facing aspect, called Faro or Faro Glades, is only good with a lot of snow and no sun crust from the previous afternoon, but on a powder day, is one of the best pitches at Vail. Lift Chair #7 again.

Run #3: Sun Down Bowl - enter Sun Down Bowl through the gate to your right and traverse around into your first Bowl Shot of the day. Consider whether South or East aspects will provide better and fresher snow conditions. The drainage in front of you is Widges gully and everything drains down there.

Run #4: Sun Down Bowl - there’s a new lift as of the winter of 2023, Chair #17, Sun Down Bowl Lift, that will take you back up Ricky’s Ridge to the top of Chair #7. Take another lap down Sun Down Bowl to the bottom of Chair #5. Chair #17 adds an extra run to the Western Zone on a powder day. Lift Chair #5.

Run #5: Teacup Bowl - it’s now 10am, and the crowds are starting to make it up the hill. You’re on top after four untracked runs, so it’s time to head to Blue Sky for the opening. Take the Sleepytime Road all the way across Sun Up Bowl to the Teacup Bowl entrance and ski the East Aspect of Teacup down to the Skyline Express Lift, Chair #37.

Run #6: Big Rock - Blue Sky opens at 10am on a powder day after Patrol is done with their bombing runs. Getting there any earlier means you’re standing in line instead of skiing. Lift Chair #37, turn left and head East down the traverse road to the top of Big Rock. Ski a fresh run in the fantastic north facing trees that get groomed every night. Take Chair #39, Pete’s Express Lift, on your right at the bottom.

Run #7: Grand Review – if it’s groomed, this is one of the best, most consistent pitches in Vail and not to be missed on a powder day. First tracks on Grand Review is a memorable run. Ski back to the base of Blue Sky and lift Chair #37 again.

Run #8: Montane Glade – the west aspect of Earl’s Bowl is a classic piece of Vail real estate. The farther out the ridge you go, the tighter the trees get and the more northerly the aspect, but it’s all good – just find a fresh line and mind the little cliff band at the top. Ski to the bottom and lift Teacup Express, Chair #36. 

Run #9: Lunch Run: it’s now 11:30am and you’ve skied eight untracked powder runs at Vail, roughly 12,000 vertical feet – Mazel Tov.  As you lift Teacup Express #36, note that the West Wall below you and the rest of China Bowl is completely tracked out. You’re tired and dehydrated, but happy. Time to head down the front side for your Noon table at Pepi’s or Alpenrose .

I met Billy Coburn on the flight from SFO to Beijing in April, 1986. We had both signed on to carry loads for the first American expedition to the north side of K2, and we liked each other from the first handshake. 

Billy’s family lived in Colorado for generations and settled the valleys near Crested Butte. He grew up in Boulder climbing and skiing 14ers with his Dad, and by the time we met he was an accomplished alpinist.

We spent a month together trekking from western Xinjiang province, over the Aghil Pass and onto the K2 Glacier to put our team of superstars in position to climb the North Face of K2. Our Chinese tour guides were worse than useless on the trek, but Billy and I loved the tribe of Kyrgyz camel-drivers that towed all our stuff to the base of the hill.

While we were skillful climbers, neither of us had been to the Himalayas before. Billy and I were soldiers, not generals on this trip and did what we were told. Mostly that involved humping 70-pound loads of food, gear and oxygen up steep, dangerous terrain in appalling conditions .

Every time we dropped a load at the high camp, we’d take the opportunity to go climbing on the peaks to either side of the K2 glacier, a collection of 7,000 meter bumps on the map with no name and no ascent history.  The weather sucked on most of our carries, but after weeks of hard work we dropped the last big load up high, returned to Advanced Base, and spent a comfortable night together in a tent at 6,000 meters.

The next morning dawned clear and crisp with no wind, the only day we’d seen like it after more than two months on K2. It was Billy’s birthday and over breakfast, he opened a card that an old friend had sent with him on the trip. Inside was a goofy message and two hits of purple microdot.

Under these circumstances, Billy and I did what any experienced alpinist would do in those days:  we dropped acid and went climbing. In a shared lifetime of peak experiences, it was one of the best days either of us has had.

After the K2 trip, Billy and I returned to Boulder to start our careers – mine in venture capital and his in real estate development. Billy and his wife Ann, a phenomenal alpinist and skier in her own right, raised their four kids in Boulder and Crested Butte to be kind people and exceptional athletes. Their daughter Emma won an Olympic Medal; Willie and Gracie have each produced beautiful Coburn grandchildren; Joe came a little later and appears promising.

Billy changed the face of Boulder in the 1990s and 2000s with his thoughtful developments , which combined new urbanist concepts in mixed use areas with historic design elements taken from Boulder’s Victorian architectural roots. You can’t drive down Pearl Street without seeing the profound impact that Billy’s aesthetic has had on our lives here. He did the same thing in Crested Butte too. Billy and I happily shared some successful projects, including our Boulder Ventures headquarters building on Pearl Street.

We’ve also done a lot of climbing and skiing together over the years, in a friendship formed forever on the slopes of K2.

Mountain Guides and their Clients are never Tourists. When you travel together to a new place to climb or ski, your job as a Guide is to ensure your Client has the trip of a lifetime. If you’re a Client, you’re there to have fun, focus on the objective, learn some new skills, do your best, and be a good partner.

Tourists go to places to see things and experience the local culture. Being there is its own point for Tourists. While local cultures are a part of guiding, it comes with the objective. Meeting the locals, eating their food, and drinking their wine is great fun for Guides and Clients, but it’s not the point. Guides and their Clients are there to get to the top.

In summer, everywhere I like to go in Canada is filled with Tourists. They’re easy to avoid – just get going early in the morning for your climb or fly a helicopter to the remote hut. But it’s still a shock when you get back to the parking lot after a day of climbing at Lake Louise and see busloads of Tourists all standing in the same place, taking the same photos every day.

It's exactly the same thing in the venture capital business. When a new technology market catches fire with investors, experienced VCs have already been there for a while navigating the risks and investing with the best teams. Then busloads of less experienced investors show up, hoping to catch the wave and pile mountains of fresh capital into these hot startups.

We call these investors Tourists.

In every new technology market, a couple of deals will turn into great public companies and dominate their space over the next decade. Everyone makes money but you can usually count these enduring names on one hand. A few more will get bought or go public at high prices and the VCs will get a good result playing musical chairs. The vast majority of deals will have their moment in the sun and then crash, leaving Tourists holding their worthless stock, wondering what they did wrong, and blaming the VCs for this bad outcome.  Then the Tourists go home and the whole thing starts over again.  

At Boulder Ventures, we’re Guides and Venture Capitalists. 

Our Serial Entrepreneurs are our Clients. 

We’re never Tourists.

On a recent expedition to Denali, the highest mountain in North America and one of the most extreme environments on the planet, BV Limited Partner, John Thomson and I set out to climb the Cassin Ridge on the South Face. The Cassin is among the world's classic glaciated alpine routes and involves a committing approach. On the Cassin Ridge, a successful summit is the best option – a retreat can be difficult and dangerous.  

Johnny and I established several markers during our expedition preparation and on the climb to ensure a suitable risk margin. For example, we completed ten training climbs together from January through May in Rocky Mountain National Park in Colorado, all in winter conditions.  

Once on the mountain, we planned five days to ascend from the 7,200 Kahiltna Glacier landing strip to the 14,200 upper base camp on Denali, a measured pace that would aid our acclimatization.  We also completed three climbs from 14,200 to 17,000 to establish confidence in our fitness and physiological readiness before committing to the Cassin Ridge.  

Our final marker was a three-day weather window. The approach to the Cassin Ridge takes one day and the total vertical rise of the route is 9,000 - nearly two miles. Our training told us that 5,000 vertical feet of climbing per day was a reasonable expectation. We planned to spend one day on approach from 14,200, sleep at the base of the Ridge, bivy one night, then push to the summit and descend back to the 14k base camp on the third day.  

Unfortunately, we never got a weather window that would give us sufficient margin for an attempt of the Cassin.  It was a stormy 2023 season, and on this trip luck and timing were not in our favor. We discussed the possibility of a two-day push but decided against reducing our margin and instead opted to climb the West Buttress route to the top of Denali. 

On June 9th, we completed the ascent from 14,200 to the 20,320 Summit in a single 11-hour roundtrip push. In addition, by maintaining an adequate margin, we had enough in the tank to support the rescue of two frost bitten climbers who needed assistance getting down the mountain. 

Mountain Guides are best in their own terrain.  Experienced Guides can and do take their clients around the world to climb and ski but landing up high in unfamiliar surroundings and expecting to guide clients safely is a tall order, even for IFMGA Guides.

Most Guides prefer to take clients to their home terrain on routes they’ve done for years.  Ski Guides who have seen their snowpack develop each season over decades have an uncanny eye for safety and quality. The best Ski Guides are locals and can serve up soft powder turns under almost any conditions. 

Likewise, local Rock Guides have their terrain thoroughly sussed, with the belay stances, gear choices, and sun angle on their trade routes optimized for client experience.  Local Guides also have access to the best resources for their clients to enjoy and are happy to make a lunch reservation at the classic Hut or a spa appointment for the down day.  There is simply no substitute for this level of knowledge and experience, and clients that hire local Guides for their adventures can have high confidence in a successful outcome.

The same is true for Venture Capitalists.  It takes years of investing in dozens of startups across multiple market cycles to find out if you’re any good at this business.  Local knowledge comes dear and the original mistakes we make along the way add to our confidence in our thesis and our value to entrepreneurs. 

Cheap money and bull markets make everyone look like an expert, especially the noobs who trumpet their illiquid successes as if they matter.  They don’t – what matters is the ratio of Distributed to Paid in Capital (DPI), the only long-term measure of a fund’s success.  

Experienced VCs become determined sellers and cautious buyers in these environments, aggressively returning capital to their investors in advance of the inevitable reckoning.  When the market avalanche comes roaring at them, the best VCs are ready with fresh capital to invest in the best serial entrepreneurs in the best local companies at reasonable prices. 

My partners and I closed Boulder Ventures VIII on November 21, 2022 at $58 million. We are ready to guide the next cycle.

The most important decision that Mountain Guides and Venture Capitalists make in their professional careers is with whom to partner.  Choosing the right partner in guiding and in business is the key ingredient in a great fund or a great guiding company. 

Because they involve risk and uncertainty, partnerships in the mountains are special. In our role as Mountain Guides, we’re responsible for a Client’s experience and safety. Clients rely on our skill to deliver the best outcome possible given the route, the weather, and the fitness of the participants. While we’re often good friends with our Clients, our professional duties as Guides are paramount in this relationship.

When we choose to climb as partners, we give up our guiding responsibilities and entrust ourselves to each other as equals in pursuit of the objective. That’s a hard thing for experienced Mountain Guides to do. We’re used to making difficult decisions under conditions of uncertainty, we like being in charge, and we’re loath to give up that authority to anyone else. But success on a big objective in the mountains requires a strong partnership.

VCs also hate giving up control over their investment choices, but it’s the rare investor who can build an enduring venture fund without partners.  Instead, the best VC funds maintain an equal partnership of successful GPs over multiple fund cycles, and demonstrate their longevity by passing along their talent, credibility, process, and insights to the next generation of partners. 

Peter Roshko and I have been equal partners in Boulder Ventures since 1999.  Jonathan Perl joined us in 2002. Together, the three of us raised, invested, and realized four venture capital funds over the past twenty years. Our success together in Boulder Ventures has resulted in an enduring venture capital partnership, and so much more.

Peter backed Kishen Mangat in his second startup, BroadHop, in 2009. Kishen’s ambitious vision then was to create a software product that would manage the complex needs of 4G carriers, a task only possible in hardware products at that time. That vision was rewarded when Cisco bought BroadHop in 2013, and Kishen took on an operating role as the head of its new software division.

Over ten years, Kishen grew his Cisco division to $500 million in annual revenues and 2000 employees around the world. Through his technical leadership and management skill, Kishen positioned Cisco to be the leader in the emerging market for 5G carrier software, and himself as a leading expert in the field.

Kishen is also a gifted alpinist and has devoted himself to the highest standard as a traditional rock climber and skier. Equally at home leading Eldo 5.11, long routes on El Cap, and steep powder turns in the Canadian Rockies, Kishen possesses the full quiver of skills we admire in a climbing partner.

Kishen’s last day as a Cisco executive was February 14, 2022.  The next day he joined Peter, Jonathan and me as an equal partner in Boulder Ventures.

Governance is key to the role venture capitalists play, and most serve on the boards of the companies they invest in.  Boards are important to a startup’s success and the best VCs aid in this corporate development effort through credibility, strategy, connections and good judgment.  Experienced entrepreneurs value these contributions alongside help with finance and rely on their VC Board members to guide them through important decisions.

Whether a public or private firm, in the boardroom Directors understand that they must come to each meeting asking two important questions: who runs the company and who owns the company?  In answering these questions each meeting, Board members put the interests of all shareholders ahead of their own, a fiduciary duty that experienced VCs embrace. 

Over the past decade, the role of governance in VC-backed startups has been diminished by Venture Capitalists eager to portray themselves as “founder-friendly”.  In exchange for an early equity option in a promising startup, many VCs have given up their governance duties and enabled corporate control among inexperienced entrepreneurs despite their minority ownership.  Big public success stories that lack good governance like Facebook and Airbnb dominate the narrative, but this strategy almost always ends badly for both entrepreneurs and investors.

Tone comes from the top and at Boulder Ventures, we take our Board roles seriously.  

Our portfolio companies embrace good Board governance as a standard of behavior and a known best practice.  Our serial entrepreneurs appreciate the governance duties that their Directors perform, and highlight these examples for their own management teams.  Employees who are shareholders are grateful for a strong and transparent Board that looks out for the interests of all the shareholders of the firm.

Boards Matter.

Faulkner’s novel about the decline and dissolution of a once-great Southern family was an epiphany to Rich and me growing up in Atlanta.  All the bad choices and bad luck piled up on the Compsons through the generations until their shared, brutal end.  As teenagers, Rich and I were surrounded by the same gentry, the same mind-set, the same culture as Faulkner described so vividly fifty years before us.  We recognized it for what it was, and we determined not to endure it.

Rich Gottlieb is one of America’s greatest rock climbers, and we’ve been partners since we were children.  Rich’s father, William Gottlieb was renowned for his photographic portraits of jazz-era greats, and Rich grew up with the soul of an artist.  He was creating sculptures in Atlanta when we first met.  I was 14.  Rich had a truck and rack, and he wasn’t afraid to use either in scouting out new climbs and new cliffs in Georgia and Alabama. 

In the 1970s, these places were remote and scary.  Tallulah Gorge, Sandrock, and Jamestown are all well-established crags now, but when we first went there, they were a blank canvas.  Rich put up all the best lines first, on sight, on lead, with a collection of partners holding the rope.  I had read about climbers of his skill and boldness in books and magazines, but never had I seen one in action.  New routing in the South with Gottlieb in the 70s was among the most terrifying and exhilarating experiences of my young life.

When we’re not climbing and skiing with our clients, Mountain Guides like to eat and drink. Food and Wine is a critical part of the guest experience and our most memorable tours include eating and drinking at familiar places we love to share with our clients.

Experienced Mountain Guides focus attention on favorite restaurants and huts in their terrain, and form lifelong relationships with the proprietors of these classic spots. This Guide/Hutkeeper relationship adds immeasurably to the quality of our client care in the field.

Restaurants are a critical piece of our Venture Capital infrastructure as well. We do a lot of lunches and Board dinners in the VC business, and our authentic relationship with entrepreneurs and investors is enhanced by our ability to serve up a fantastic meal at a place where we’re known, liked, and welcomed.

As a result, we’ve worked hard over the past thirty years to support our local restaurant scene in Boulder, one of the foodiest towns in the US . The quality, variety and competence of our favorite Boulder restaurants is startling.

That a midwestern college town of 100,000 souls can consistently serve up the best food and wine for 1,000 miles in any direction is surprising to sophisticated newcomers, but not to the local Mountain Guides.

Here are our favorites:

Boulder Wine Merchant - while a casual storefront, master sommelier Brett Zimmerman’s wine shop is a marvel of world class inventory and expertise.

Cured - pro cyclist Will Friskhorn and his adorable wife Coral (whose Dad was my childhood climbing hero) own Boulder’s best cheese shop on Pearl Street. It’s a favorite for sandwiches, roses and party plates. Boxcar coffee is co-located, with one of the best pours among Boulder’s many excellent local coffee stores.

Frasca - Bobby Stuckey’s destination gourmet Italian restaurant, which has won awards and stars for years, is world famous. Bobby’s excellent pizza joint, Pizzeria Locale , is next door.

Jax - legendary restauranteur Dave Query’s signature raw bar and fish place is always crowded and delicious. His Cuban restaurant down the street, Centro , is high on our list as well.

Mateo’s - heir to Tony Laudisio’s Boulder fine dining legacy, Matthew Jansen serves up delicious Provencal lunch and dinner on Boulder’s best Pearl Street patio.

The Kitchen - chef Hugo Matheson’s original Pearl Street location has expanded up, down, and across the country, but his original store is an homage to the cuisine of Alice Waters of Chez Panisse. Hugo’s devotion to healthy American cuisine from local organic producers makes for an exceptional dining experience.

There are only a few thousand IFGMA Guides in the world, spread across 27 member countries. It’s a small community bonded to the mountains and to each other through their shared passion and proficiency. As a guide and as a client, I’ve skied and climbed with many of the best Mountain Guides around the world.

People often ask me who is my favorite Mountain Guide, and the answer is always the same: Diny Harrison .

There was never a Guide like Diny before her - she was the first woman to become a full IFMGA Guide in North America. Diny did it in Canada, where she grew up skiing, climbing and kayaking, and demonstrated a high-level skillset in all three disciplines as a teenager. She then applied herself to snow study as a patrolman at Lake Louise ski area, and worked her way up the alpine competence hierarchy across British Columbia.

Diny began heliski guiding for CMH when she passed her ski exam in 1988, and spent more than fifteen years as a Lead Guide, mostly in the Monashees and in Revelstoke , where she ran the Lodge after Buck Corrigan. She became a full IFGMA Guide in 1992, when we first met and starting climbing together. Now she’s the Lead Guide at Mustang Powder , a classic Cat skiing operation west of Revelstoke.

Knowing Diny as well as I do, it’s not surprising that she became a Guide. Her skiing and climbing skills are world-class. Knowing her peers in the ACMG as well as I do, it’s astonishing that she put up with that bunch of old-school knuckleheads long enough to earn a Pin.

But there’s something more to her than a demonstrated competence in the mountains: Diny Harrison is a truly entertaining person to be around. She is hilarious and completely unintimidated by anyone. She has an endless supply of dirty jokes . She looks you in the eye and tells you what she thinks - there isn’t a single strand of passive-aggressive DNA in her genome. She speaks four languages fluently and is funny in all of them. These are all important qualities in a Mountain Guide, and they are all abundant with Diny.

Occasionally, we encounter VCs who consistently produce a great result in the funds they manage, but it’s hard to identify their secret sauce - at some point you have to admit that it’s talent. Same is true of Diny - she’s just really good at Mountain Guiding.

At Boulder Ventures, we love the Grateful Dead and listen to them all the time. Jerry Garcia was a great entrepreneur who understood the economics of the music business in the digital age long before anyone else.

Like most great entrepreneurs we’ve known, Jerry didn’t give a shit about money and status. He cared about his band and their music, and he was motivated by the creative process. Jerry didn’t care about being a Rock Star either, but more than any other group of his era, the Grateful Dead made its audience part of the act.

As a result, Jerry created a strong following among his fans, who then organized themselves into a community, which then enabled the Grateful Dead to play dozens of shows a year to sold-out audiences largely comprised of the same people. As the CEO of the Dead, Jerry recognized that this recurring revenue model was more fun and far more profitable than selling a single studio album a single time to a single fan.

Impressively, Jerry Garcia also understood how to conduct himself in a transaction once he had a seat at the table:

Since it cost a lot to win

And even more to lose

You and me bound to spend some time

Wondering what to choose

It goes to show you don't ever know

Watch each card you play

And play it slow

Wait until your deal come round

Don't you let that deal go down

I been gambling hereabouts

For ten good solid years

If I told you all that went down

It would burn off both your ears

A seat at the venture capital table is expensive, but it’s nothing compared to the cost of getting schooled in a high-flying, capital intensive startup. The streets of Boulder are littered with guys that thought they had a winner, only to get crushed by luck, timing, bad management, or all three.

No one ever lost their VC job because of the deal they didn’t do - it pays to take your time, ask a lot of questions, and work hard on your authentic relationships before committing capital. Even then, the big winners leave you shaking your head - you don’t ever know for sure what’s going to work.

It takes a minimum of a decade of effort before you find out if you’re any good, as a founder or as a VC. Jerry was good, and went for thirty five years with the Grateful Dead before he died of too much fun in 1995.

I’ve been gambling hereabouts for thirty five years also, working on The Deal. I’m not even close to done…

Mountain Guides are larger-than-life characters.  Among the skills Guides acquire over a lifetime in their terrain is to project confidence and competence to clients, and then to demonstrate both in the daily conduct of their jobs.  Venture Capitalists are called on to do the same thing by their investors and entrepreneurs. In addition to a track record of returning capital at a multiple, the great VCs I’ve known are equally comfortable in front of the conference crowd, at the head of the Boardroom table, or on the factory floor.

No matter how gifted you are at climbing and skiing, no matter how much experience you’ve gained before and during Business School, no one starts out that way.  Instead, we create our persona over years of guiding and investing.  Only with persistence and durability do we emerge and succeed as VCs and Mountain Guides.

Once we’ve acquired fundamental skills through training and experience, some of our progression is accomplished through modeling our mentors.  There is no better teacher of how to act as a VC or a Mountain Guide than our role models. I was fortunate early in my career to have Merc Mercure as my mentor. A Physics PhD from CU, Merc was the founder and CEO of Ball Aerospace, the biggest company in Boulder, along with a number of successful local startups. Merc gave me my start at his fund, Colorado Venture Management in 1986, and I’ve modeled my VC persona on his combination of technical chops, business acumen, and leadership style.

Some of our progression is accomplished through peer interactions over the course of our career. Earlier in my career, finding a tribe of young VCs with whom I connected personally and professionally was a critical element in the development of my business persona. Today, I’m actively supporting a cohort of local aspirant investors in their journey. Where matters: they all live here and can ski and climb, which makes the job of sponsoring a cohesive Young Venture Mafia in Boulder much easier.

Some of our progression is accomplished through introspection.  By challenging our decision-making under conditions of uncertainty, we learn to avoid heuristic traps that could lead to fatal outcomes in the mountains or on our balance sheet. Each winter in Vail, I try and take two or three days to go touring by myself to scope out new terrain and to think about how to improve on the decisions I’ve made that season. The best VCs constantly question their assumptions, not themselves.

One of my favorite movie stars is Cary Grant, who projected an incredible screen persona especially in his Alfred Hitchcock movies.  But he was born Archibald Leach in Bristol, England and only came by his debonair presence through a lifetime of devotion to the craft of acting.

Here’s how Cary Grant described his progression: “I pretended to be somebody I wanted to be until, finally, I became that person. Or he became me. Or we met at some point along the way.”

Like VCs and Mountain Guides, he became himself.

It’s hard to learn to Do the Right Thing when you’re a venture capitalist. There are a lot of constituencies that demand your attention:

Your duty is to your entrepreneurs, because all your success as an investor derives from them.

Your duty is to your Limited Partners, because you have a fiduciary responsibility to manage their money, at all times putting their interests ahead of your own.

Your duty is to your Partners, because without a cohesive team making investments together, your Fund’s effort falls apart.

Your duty is to your portfolio company employees, whose careers and livelihoods are in your hands as the lead investor in the startup where they’ve committed their human capital.

Your duty is to yourself, to your family and to the happiness of the people who care about you the most.

Your duty is to your community, because the companies you finance create unintended consequences that can be harmful to those around you.

It is common in our experience as VCs that sometimes these duties are in conflict. What might be best for our companies may not be best for our Fund’s economics. What might maximize my return might not be best for my investors. The hard work and dedication that an investment requires of me might interfere with my family’s happiness. The successful product my company makes might pose an unforeseen risk to my community.

How we balance these duties defines us in our careers. One of my intellectual heroes, Nassim Taleb, says "Weak men act to satisfy their needs, stronger men their duties."

Sam Dryden was a great Venture Capitalist and Philanthropist who pioneered the genetically-modified seed business with his partner, Mark Wong . I officed with Sam and Mark from the start of Boulder Ventures, and we were climbing partners, co-investors and friends for more than thirty years until Sam’s death in 2017.

Sam’s world was complicated. There’s no free lunch in the ag business, and the competing interests of seed companies, trait owners, distributors, farmers and the public over issues of economics and food safety affect us all. Sam and Mark created this ecosystem at Agrigenetics, Monsanto, and Emergent Genetics, and they successfully managed these conflicts throughout their careers together.

Because of his experience with the issues and consequences around agriculture and technology, Sam was also an influential advisor to the Rockefeller Foundation and ran the global food initiative at the Bill and Melinda Gates Foundation . But the most impressive thing about Sam was the way he interacted with the people he met: with humility, compassion, and a sophisticated understanding of the complex ways his decisions affected them.

Throughout my progression as a VC, I’d spend time with Sam and ask him what to do when a conflict arose. We’d talk for hours about all of the possible outcomes from our actions, how to balance the risks, whose interests were at stake and why. Sam was especially good at finding ways to align the interests of different parties, so that the choices we made benefitted everyone.

But when the discussion was over and we had to make a decision, Sam always gave me the same advice: Do the Right Thing.

Primates who live in groups create hierarchies.  These hierarchies form the structure of our societies and are genetically embedded in our behavior as a species. Historically, human hierarchies have used physical, emotional, or ancestral means to exert dominance over their peers.  Only recently have we witnessed the emergence of hierarchies based on competence.

Mountain Guiding is an excellent example of a modern competence hierarchy.  Among alpinists, IFMGA Guides represent the pinnacle of success.  No amount of political, financial or religious influence can earn someone an international certification.  Instead, certified Mountain Guides must demonstrate competence in skiing, rock climbing and mountaineering through years of rigorous training and testing by their credentialed peers. 

While an upbringing in a mountainous region and an abundance of local mentors can be helpful to a Guide early in her career, ancestry alone cannot create a successful Mountain Guide.  Likewise, every Guide I know has experienced their fair share of near misses, any one of which could have ended their career or their life. But luck and timing can’t make you a Guide.  Even those with the physical skills to be great skiers and climbers will never earn a Pin without the education, experience and desire to be an IFMGA Guide – they must achieve competence to stand atop this hierarchy.

To thrive and endure, successful competence hierarchies embrace diversity and inclusion.  It’s not a moral imperative but a practical one:  competence hierarchies must find and support the largest pool of candidates possible to ensure that the very best individuals rise to become their leaders. 

Among member countries of the IFGMA, the AMGA has done an excellent job of cultivating and expanding its pool of candidate guides.  Of the 138 internationally certified AMGA guides so far in the US, 11 are women, a larger percentage than any other Guides organization in the world. 

My friend Angela Hawse , the AMGA’s President, is a world-class Mountain Guide who exemplifies the spirit and skills of this competence hierarchy.  Angela has led the AMGA’s efforts to expand its candidate pool through an increased emphasis on diversity and inclusion, and all of us in the AMGA are proud of this continuing effort and its results.

Venture Capital is also a competence hierarchy, although a less perfect example than mountain guiding because the stakes are so low.  In guiding, incompetence can cost you or your clients their lives; the worst thing that happens in venture capital is that you lose someone else’s money.

Most VCs were born on third base , and many have achieved success through family connections or luck rather than competence.  While real investment talent wins over a long period of time, the venture capital industry so far has been successful without a set of transparent standards or metrics that select for competence among its members. 

As a result, the VC business has been slow to broaden its candidate pool.  However, there’s been a welcome change over the last few years as more brand-name funds have put real resources behind inclusion and diversity among their aspirant venture capitalists.  That’s a good thing if we hope for the venture capital industry to persist as a competence hierarchy. Otherwise, VC investors will be automated out of existence in the future by an AI that can make better investment decisions.

Mountain Guides are in no such danger.

At the core of our friendship is a shared climbing history.  Climbing in our generation was a deadly serious business, and Stevie and I are surrounded by the ghosts of partners who did not survive it.  Whether through luck or skill, we did and now get to enjoy our climbing together at a more relaxed pace.

Stevie met me in Sicily a couple years ago, a place neither of us had been and where no one knew who we were.  There was an international Guides meeting that I was asked to attend for AIARE, and it’s an easy flight from Zurich where I was on business.  Stevie lives in Malta now where his Mother grew up, and it was a short hop for him to Sicily as well.  The rock climbing is rough by the buffed-out standards of the European crags we frequent, but the food and wine in Sicily are exceptional and the hospitality of the locals can’t be beat.

One day, we did a climbing tour around Mt. Etna with the AMGA’s able Executive Director, Alex Kossef , sampling the crags on the volcano’s west and north sides.  After climbing, we ended up at a new winery established by my friend Carlo Franchetti , one of Italy’s greatest winemakers.  Carlo and his brother Andrea have resurrected some ancient narello mascalese vines on the slopes of Etna and now make a series of outstanding single-vineyard crus called Passopisciaro .  We were welcomed warmly to the property and Stevie, Alex and I got to sample all of Carlo’s best vintages in an epic tasting.

On our penultimate day, Stevie and I drove down from our villa to the ancient town of Siracusa.  We parked ourselves at a classy beach resort, climbed a mile-long sea level traverse of the limestone cliffs that ring the coastline, and followed that up with an awesome lunch at their one-star restaurant.  After espressos and a swim, we decamped for a steep crag south of town.  Stevie floated the overhanging limestone routes and was gracious enough to hold the rope for me as I flailed away at them.  We cleaned up, toured ourselves around the ancient city and found an excellent plate of Sicilian pasta there for dinner. 

On the drive home, I realized that I was happy in Sicily with Haston.

Malcolm Gladwell says the qualities of satisfying work are autonomy, complexity, and a connection between effort and reward.  Mountain Guiding and Venture Capital are rich in all three.

Mountain Guides have a lot of autonomy – with an IFMGA pin, you can work anywhere in the world.  Building a list of competent clients takes a long time but creating authentic relationships with them is a rewarding way to earn a living.  Mastering your terrain as a Guide is infinitely complex, but the changing mountain environment keeps you engaged in a way that’s hard to duplicate in the real world down below.  The connection between effort and reward in Mountain Guiding is direct:  your Clients pay you for your effort and tip you based on the outcome. Mountain Guiding is satisfying work.

VCs have a lot of autonomy too – we get to decide how to spend our time and on what to focus.  The best VCs learn that time is their most valuable currency and spend it wisely on the most important projects.  Whether your focus is on a vertical market or on a specific geography, the early-stage investment business is complex.  The connection between effort and reward for VCs is direct: we make a lot of money investing in successful companies whose market value rewards investors with a big multiple of invested capital. Venture Capital is satisfying work.

In 2013, I formed the Board of Directors of the American Institute for Avalanche Research and Education (AIARE), and have served as its Chairman for the past ten years.

AIARE’s mission is to save lives through avalanche education, and its courses are the certification standard for snow professionals and recreationalists throughout the USA.  Every time someone dies in an avalanche, their death echoes through the valley, affecting their families and friends.  AIARE’s network of course providers, most of whom are Mountain Guides, teach avalanche safety and awareness to more than 15,000 skiers and snowmobilers each year.

As Chairman of AIARE, I have the autonomy to travel across avalanche zones throughout the winter, skiing with AIARE’s course providers and experiencing their complex terrain.  There’s no economic return for me, but the reward for our success at AIARE is profound.

We’ll never know the true impact, but the numbers are unassailable: as backcountry use among snowmobilers and skiers has skyrocketed over the past decade across the Intermountain West, avalanche deaths per year have remained stable because of AIARE.

That’s satisfying work.

At Boulder Ventures, we’re only interested in important projects, where successful outcomes can move the dial financially for our investors and for the society we live in. 

We only go on trips like this with people we know and trust, who we’ve been doing this with for decades.  Everyone knows what they’re getting into, everyone has a lifetime of experience doing it, and everyone knows what to do once we’re there – that experience base allows us all to focus on the objective, instead of on a bunch of stuff that doesn’t matter.  The same is true of our relationship with each other as General Partners, and with our serial entrepreneurs at Boulder Ventures.

Our projects are risky. We could die climbing in the Selkirks or lose all our money investing in startups, so we work hard to manage those risks to achieve the best outcome we can.

We know the Guide that owns the Hut, what to bring, who to call for the helicopter and what time of year to go for the best weather.  You can’t find this information anywhere – you have to know the people, have access to the tools, and know how to put them together for success.  The same is true in venture capital – you have to know what to do and how to do it. Despite what you read on the internet, there’s no instruction manual in our business.

All of us at the Moloch Hut in the summer of 2018 were proud to be there and proud to climb together – it was a worthy objective for a world class group of experienced Guides and climbers.  We feel the same way about Boulder Ventures – we’re proud of our portfolio companies and the teams that run them, we’re proud to manage our investors’ capital, and we’re proud to be in business together.

Venture Capitalists and Mountain Guides live in the future.  To be good at what we do, we have to.  Planning for the next adventure is a constant in guiding and requires both a near term and a long-term view to dial in the best experience for our Clients.  Whether it’s an 8000 meter peak, a fast ascent of El Cap , or a Ski Tour across the Columbia Icefields, an ambitious future objective requires commitment, planning and progression on the part of Guides and Clients.

VCs do the same thing.  While we’re in constant contact with our serial entrepreneurs, assessing our people and results against quarterly objectives, we’re also looking out three to five years across the investment horizon to test if our thesis is intact.  History informs our worldview, but to be good at the venture capital business, we have to live in the future and visualize the risks and opportunities that will impact our portfolio companies. 

One of our best examples of living in the future is Black Bear Energy .  Drew Torbin helped pioneer the rooftop solar business at Prologis, and now he and his team have built an even bigger business serving the solar needs of all the other industrial and commercial REITs.

The future of the built environment is turning the flat rooftop of every industrial and commercial building in the US into a solar plant and combining it with on-site battery storage and LED lighting.  In the future, our cars, houses and businesses will all run off this type of distributed generation.

The future won’t happen because of our increased awareness of climate change, our desire to promote sustainability, or a big tax break. 

It will happen because the cost of solar, storage and LEDs has been declining 30% per year for a decade and will continue to do so in the future. It will happen because institutional property owners and their tenants don’t want to rely on an antiquated grid to power their operations. It will happen because the tenant’s employees want to plug their cars in at work.

Most importantly, it will happen because Drew and Black Bear have proven to the REITs that they can increase cash flows from rooftop solar without increasing capital costs.

Naval Ravikant says that if you want to live in the future, live in the freest place around because eventually, all of the innovators and creators will show up there. That’s the future where Drew and Black Bear live.

Mountain guides and venture capitalists love to share success with our partners. After struggling together for many years, it is a special moment when a VC and her entrepreneur celebrate the exit of their company. Within the context of their  authentic relationship , this moment is both joyous and bittersweet.

Joyous, because the only peaks worth climbing together are demanding ones, and the effort brings out the best in both of them.

Bittersweet, because their shared success might not be repeated for a long time, if ever.

Experienced guides learn to savor these moments, and work hard to make them special for clients. In recognition of the importance of the customer care skill set, the AMGA recently adopted a fourth discipline,  Apres , to the Alpine, Ski, and Rock standard for the certification of full guides.

Since I introduced this discipline to the American guides and have practiced it for decades, the AMGA has hired me as their new Apres Discipline Coordinator, a role for which I’m highly qualified.

A local guide might attain the summits of his home range a dozen times each season, but even the most determined client might only experience a few of those heights in a lifetime.

A skilled venture capitalist might make as many as fifty investments over her long career, but a seasoned serial entrepreneur will have a chance to start only five companies in his.

When one of these companies or peaks is a success they share, there is a cause for professional celebration.

While the great entrepreneurs I’ve worked with always credit their teams for the prosperity of the effort, they also take time for a memorable glass of wine with their venture sponsor.

Of the traits shared by the venture capitalists and mountain guides that I’ve known in my career, opening an excellent bottle without provocation has been a consistent theme.

Mountain guides owe their first duty to client safety: no matter what the outcome, everyone must return home in one piece. But once the climb is behind us, mountain guides and venture capitalists all practice the Apres discipline with the same motto:

Safety first, then drinking!

Stacked blocks are an alpinist’s worst nightmare. You’ve come to a place where the only path forward is through a loose, vertical pile of giant boulders, held together by an unknown combination of ice, grit, and gravity.

It is not obvious that a good outcome even exists:

If you climb up through the stacked blocks, you might bring down the whole pile, killing yourself and your partners below.

If you climb around the stacked blocks, your route might end there, with no path forward.

If you retreat from the stacked blocks, you’ll never forgive yourself for backing off the line of ascent.

Every entrepreneur knows the helpless feeling facing stacked blocks in her startup. The way forward could be fatal, but there are no clear alternatives. Retreat feels lame, but unavoidable.

It is here that the great venture capitalists find a path to success with their entrepreneurs. The key to surmounting stacked blocks is not luck, but experience. Looking carefully at the pile, understanding how they weigh against each other, judging the angles, and comparing these against the prior configurations we’ve encountered — all of these inputs lead us to the solution.

Steve Chambers  and I were determined to claim the first ascent of the white face on the East flank of Boulder Mountain in the Adamants. You could see it from the deck of the lodge lit up in the afternoon, a plumb line from the summit. Best of all, Unterberger had tried and failed to climb it.

But 200 feet up the steep wall, we realized that the entire upper half of the face we were climbing were stacked blocks, balanced against each other and frozen to the ice behind them. It was the most precarious place I’d ever encountered in the mountains, and utterly terrifying. Steve took a deep breath, and led out on the boulders, testing each one carefully, making choices based on his experience, insight and intuition.

Hours later, we stood together atop the first ascent of the Chambers/Lefkoff, satisfied that we’d done our best together.

There is always a path up through the stacked blocks, but it requires patience and attention to detail, and it is rarely simple. In the middle of a difficult climb, with all the turmoil that surrounds us, it’s hard to relax and focus on what is in front of us and then piece together the solution. But that is precisely what is required of a competent mountain guide, and of a successful venture capitalist.

All climbers like to boulder and most lifers would rather get a workout touching actual rock than climbing in a gym. Bouldering in my generation was an extension of being a rock climber; having a repertoire of hard local problems in your quiver was a requirement if you wanted to burn off the visitors.

When I was young, my friends and I idolized  John Gill , the father of modern bouldering. Gill was the first guy to focus all his energy on bouldering instead of treating it like practice for rock climbing. He was so much better at it than everyone else in the world that his bouldering problems weren’t repeated for decades after his first ascents.

Gill was a gymnast and a climber. He bouldered in a dynamic, fluid style born of his gymnastics training unlike the climbers that came before him. I spent a lot of time in the 80’s trying to repeat Gill’s boulder problems in Colorado, an effort that required days of strenuous, often pointless effort. When I finally got one of them, I worked it relentlessly so that I could do the Gill problem every time, with timing and grace.

My Gill quiver brought visiting hardmen to tears.

Mastering a business model is the entrepreneurial equivalent to bouldering. We make money in our companies by doing the same thing well, over and over again. It takes an enormous effort to master a new business model, but this expertise then forms a moat around your businesses that keeps the copycats away.

Apart from the joy in relentlessly flogging the competition with our competent execution, there is reward in delivering our products and services at scale with a consistency and style that delights customers. In addition to the satisfaction of creating a successful enterprise, that reward is usually a big multiple of invested capital.

The best example of bouldering in our life sciences portfolio is  ArcherDX , which sells kits to researchers that enable them to repeatedly and accurately identify cancer genes in tumors. Jason Myers, ArcherDX’s founder and CEO, has been focused on this problem for years. Through multiple iterations of their product, Jason and his colleagues have developed the best NGS tests out there for cancer researchers and drug companies, because ArcherDX works every time, consistently and at scale.

The strongest and most stylish boulderer today is my friend Paul Robinson. He is the modern heir to Gill and his dynamic style. Paul devotes himself to new problems that often involve years of effort, but his bouldering has achieved a level of difficulty unimaginable to Gill in his day, or to me in mine. Paul is a talented filmmaker as well and has his own YouTube Channel. It’s worth checking out:  https://www.youtube.com/user/akahnprob/videos

People who hire professional mountain guides to take them skiing in the mountains spend a lot of time and money getting there. When they arrive at their destination, they expect to find good snow.

No one knows their terrain better than a local ski guide and no one can find better snow at any time of the winter season. For both safety and quality, hiring a local ski guide is the best investment you can make on an expensive ski holiday.

Ben Bartosz is a talented ski guide and an expert on the Vail Pass terrain, between Vail and Copper Mountain in the Central Mountains of Colorado. Ben and his wife, Jenna, have operated the  Vail Powder Guides  Snowcat for more than a decade. We do a lot of skiing with Ben and Jenna, and the VPG Cat is a favorite among Boulder Ventures investors, entrepreneurs and fellow VCs.

While I’m impressed with Ben’s ability to find the best conditions amidst his vast tenure, once he gets to the right aspect and elevation of any given tour, Ben is excellent at keeping the groups skiing on that ideal piece of real estate.

“Never leave snow to find snow,” he says.

Successful venture capitalists do the same thing. It takes a long time and a lot of laps to find the right terrain and the right clients but, once we do, good returns owe more to execution than chance.

Some VCs intensively mine their geography for great entrepreneurs and then spend all of their time cultivating an  authentic relationship  with these deal magnets. Others focus on a vertical technology market, accumulating wisdom and investing in the best ideas across the hype cycle.

With consistent devotion to the craft through time, the odds favor the likelihood of a big winner. Once an experienced VC has found her market or geographic sweet spot, and demonstrated an exceptional outcome or two, limited partners flock to them.

When you’ve found the soft turns, don’t leave. Ben and Jenna have taught us that it’s better to keep skiing right there.

Venture capitalists and mountain guides are perfectionists. We plan, and scheme, and study, and try to map out all the nuances to achieve the ideal result. Some of these we share with our entrepreneurs and clients because we need and value their input. Some we do not because the sausage-making would freak them out.

Our goal in every deal, on every climb, is to obtain a good outcome.

Good is achievable. Great is sometimes in reach. Flawless is possible. Perfect is not.

Nothing is perfect.

This fact irritates VCs and mountain guides to no end. As perfectionists, we’re constantly revisiting our past mistakes even in successful outcomes, in hopes of making original mistakes in the future. This constant pursuit of perfection in our professional lives is fine, so long as it doesn’t interfere with our goal: to obtain a good outcome.

We are awash in mediocrity. It surrounds us so much that guides and VCs forget that just by consistently performing at a good standard, we’ve distinguished ourselves from everyone else.

Throughout my career I’ve been impressed with the quality of the imperfect people who call themselves venture capitalists. The best ones are lucky and smart and display a rare, intuitive understanding of the context of their role in early stage companies. But these talented individuals are frequently frustrated by the limitations of our craft.

A blown IPO, an entrepreneur’s hanky panky, a key regulatory change, a rare but deadly computer virus — all the ways that great startup companies deal with unexpected setbacks — define them and their eventual success. But these same imperfections drive their VC investors insane.

The mountains are the same. Every day on the hill, crazy stuff happens that threatens to derail an otherwise perfect tour plan. The best guides accept these random events as part of the experience, adjust the plan, and with a big smile and a small shrug, lead through to the summit.

Great venture capitalists and mountain guides share the same quality: they refuse to let the Perfect be the Enemy of the Good.

My favorite movie of all time is  The Eiger Sanction , a classic Clint Eastwood thriller of the ’70s, shot in Moab and in the Alps by real climbers. At the end of the film, rappelling off the North Face with the body of their dead partner, Clint looks at the Austrian guy and says: “Don’t worry, we’ll make it.”

“I don’t think so,” says the Austrian with a smile, “but we will continue in good style.”

Style means something specific to mountain guides and venture capitalists. And to the good ones, it matters a lot.

Roy McClenahan was among the best rock guides of my generation and taught me a lot about guiding style. Roy was a master of his terrain in  Tuolumne Meadows , high above Yosemite Valley, and guided clients there in good style for a decade. He developed a reputation for excellence on the rock and off that made him a favorite of the best clients, and a model for the aspirant rock guides of the  Yosemite Mountaineering School .

Good style to a mountain guide means picking the right route for the client, moving at a comfortable pace together, reaching the summit ahead of the crowd, and returning to a sunny spot on the deck of the hut for a cold beer and a plate of rosti.

Guiding in good style also means you look like a mountain guide: top quality outerwear and the proper gear packed in good order so that there’s everything you’ll need for the ascent. There’s a reason that IFGMA guides all look the same the world over; they know what they’re doing and they do it in style.

Good style in venture capital investing means a friendly but complete negotiation; a detailed, signed term sheet; an appropriately defined due diligence period; a clean set of Series A Preferred documents; and a final closing that precisely matches the original terms…followed by a cold beer and a plate of rosti.

Investing in good style depends more heavily on the skill of the VC than on the skill of the entrepreneur. It’s our job to know what are the likely deal points that could cause conflict and to get those out on the table early. It’s our job to make sure that the founding team all share the same vision and values, and to convince them that their CEO has picked the right investors to drive success, not just the firm that agreed to pay the most. It’s our job to craft a plan expectation that tempers enthusiasm and enables sandbag excellence.

In venture capital and in mountain guiding, it is insufficient to achieve the summit through luck and timing. Like Cowboy Roy, we must strive to do so in good style.

I was headed to the San Juan’s for a ski tour in April 1989 when Charlie told me to meet him in Rifle. There was a new crag under development in a canyon just out of town and he wanted to check it out. Although we had climbed on the impeccable, freshly-bolted limestone in France the summer before, these routes in Rifle were steep, slippery and sequency. We both got spanked.

It was not a new experience for me, but it was for Charlie.

Charlie Fowler was the best mountain guide of my generation of Coloradans. Like me, he grew up in the South where he started climbing, and like me, he headed to Colorado after college. Also like me, he got his ass kicked on K2 but that didn’t keep him off the summit of at least three other 8000 meter peaks, including Everest.

Charlie was good at everything he did:

a talented traditional rock climber, he tallied first ascents and bold solos of classic routes throughout the West;

a premier alpinist, he was at the cutting edge on steep water ice;

a natural mountain guide, he was an early member of the AMGA and helped establish the instructor team that taught the IFMGA standard to a new generation;

a popular teacher in his hometown of Telluride, he started a high school climbing program that thrives today; and

Charlie guided movie stars and billionaires. He was smart and handsome with a dry wit that women adored.

But Charlie was always way ahead of his time and never got credit for his talent.

When Charlie soloed the Direct North Buttress of Middle Cathedral in 1977, we all thought he’d completely lost his marbles. When  Alex Honnold soloed El Cap  in 2017, it was a major media event.

In 1992, when Charlie and John Catto lugged their film cameras up the first ascent of Cerro Cathedral in Patagonia, the resulting movie “ La Escoba de Dios ” was seen by about 30 people, all of whom I know (it’s a classic, by the way). Today, the latest Conrad Anker epic premiers to millions around the globe on HBO.

When Charlie and his wife Christine disappeared on a climbing trip to China in 2006, I had to look at a map to find the Ge’nyen Massif of the Shaluli Mountains in the Sichuan province, an obscure range of unclimbed 6000 meter peaks. Charlie died there, but 30 years from now, it will probably be the Chinese version of Chamonix.

These days, if you go to Rifle on any nice fall weekend, the place is packed wall-to-wall with climbers, most of whom have the place ruthlessly dialed. 5.14 is no big deal at Rifle now and the 5.12s are warm-ups.

In climbing, just like in venture capital, being early is the same as being wrong.

When I first moved to Colorado full-time, I got into a lot of trouble with Chip Wilson. We skied and climbed together all over the place in the early ’80s, and had just enough skill and more than enough drive to put ourselves where we never should have been.

In those days, I didn’t mind if someone climbed better than me and I didn’t mind if they skied better than me, but it pissed me off if they climbed and skied better than me.

Chip really pissed me off.

One day on  Berthoud Pass , we made it up late on a spring powder day and went way out the ridge to South Chutes on Hidden Knoll, where Chip skied the year before. All the red flags were waving: a crappy snowpack, warming conditions, cracking and settlement everywhere. Chip pointed it down the line and made perfect turns to the bottom to wait for me.

I made my first turn off the top and the whole layer cut loose, sending me in a pile to the bottom, buried up to my waist. If the slide had stepped down, I might have been killed. Instead, I walked away and resolved to pay more attention the next time.

Chip and I stuck our necks out together on rock and on skis, learning the terrain and testing our limits. We came down the curve pretty fast, but in retrospect we’re both lucky to have survived.

The same is true of my experiences as a venture capitalist.

When Peter Roshko and I started out in our funds in the mid-’80s, there were about a dozen guys in the U.S. who knew what they were doing in the venture capital business:  Frank Bonsal , Paul Ferri, and  Tony Evnin  on the East Coast; Tom Perkins, Don Valentine and  Bill Davidow  on the West, to name a few. Carl Carmen was the only guy in Boulder who got it in those days. Peter and I spent all of our time as young associates trying to learn how these successful VCs did their jobs.

What we discovered was that everyone was making it up as they went along. There was no rule book, no success model, no established regime that made being a journeyman VC a slam dunk.

Instead, we did our best to find experienced entrepreneurs with good ideas about how to build stuff for fast-growing tech markets, and pointed our hose full of other people’s money at them to help them grow. We stuck our necks out, backed some good companies, and surprisingly, didn’t get killed. The fact we both succeeded is a testament to luck as much as talent.

Peter and I have been partners for 22 years, a long time in the venture business. We’ve made more money together than we’ve lost, and we’ve learned a lot along the way about what to do and how to do it. Every once in a while, we’ll uncork a big one.

Chip has lived in Telluride for decades now and pours concrete at a profit. He still climbs a little, especially if it’s a  desert tower with Crusher , and mostly rides around on his one wheel.

But when it snows, Chip Wilson will point his snowboard down the steepest line in  Bear Creek  and carve flawless turns in high-hazard terrain to the astonishment of the assembled youngsters.

Good judgment comes from experience.

To mountain guides and venture capitalists,  where  matters. There are only a few great ranges in the world suitable for guiding and even fewer that are outstanding day in and day out. In places like Revelstoke, Chamonix or Telluride, there’s a lifetime of guiding to be had. The guides that live there become masters of their complex terrain, attracting clients from over the world, all year long.

Likewise, there are only two great venture capital centers in the USA: the Bay Area for technology and Boston for life sciences. Venture capital funds are concentrated in these two zones and their investments comprise more than 80% of the venture capital market each year. The best entrepreneurs naturally flock to these places where talent and the money is concentrated.

Atlanta, where I was born, will never be a great place for either climbing or venture capital. Atlanta’s business landscape is dominated by Fortune 500 companies and real estate developers, not startups. The local universities, Georgia Tech and Emory, are good schools but have no history of successful technology transfer.

Growing up in Atlanta, my local climbing crag was  Stone Mountain , a 600-foot granite dome with a steep north face. I came of age climbing there and my last route was a crack line just right of the giant carving of Civil War heroes chiseled into it; I named it “The Three Losers.” Soon after the carving was completed in 1974, Stone Mountain was permanently closed to climbing and has been ever since.

I moved to Boulder, Colorado, where everyone is a climber and the only symbols on the crag are an occasional banner unfurled to protest fracking. The business landscape here is sculpted by generations of indigenous startups in technology, medicine and natural foods. The  University of Colorado  has been spinning off successful Boulder companies based on faculty discoveries for 30 years. Real Estate developers in Boulder are generally despised and marijuana is commercially available.

Most importantly, rock climbing has a long and rich history in Boulder. Along with the headquarters of the  American Mountain Guides Association , Boulder boasts more mountain guides in residence than any other place in America.  Eldorado Canyon , my local crag now, is among the finest traditional climbing spots in the world, and you can see professional mountain guides taking clients up its colorful sandstone walls every day.

Rob Slater  was one of the strongest and most versatile climbers of my generation. An expert at big wall, aid climbing, his first ascent in 1984 of El Capitan’s Wyoming Sheep Ranch remains one of the neckiest leads ever on the Big Stone. Rob also loved  BASE jumping , successfully hucking himself off many of the formations he climbed.

Rob and I were at the University of Chicago at the same time and began climbing together in the late ’80s. He was busy then trading money funds for Goldman Sachs and I was busy building a venture capital business, but each year we found time to take a climbing trip to a place neither of us had been.

One fall weekend, we went to the Colorado National Monument to climb a couple of its beautiful desert towers. Rob was big on desert tower aid climbing in those days, and I was not, so we agreed to pick objectives that could be free climbed. One of those was a classic Layton Kor Route called  Fast Draw : three pitches of hard crack climbing to the summit of the Sentinel Spire.

Rob and I climbed Fast Draw together in good style, and on the summit, I offered my hand to him in congratulations. He refused. “Wait till we get down,” he said.

We made two rappels back to the base of Sentinel Spire, and at the end of the last one, I again offered Rob a handshake. Again, he refused.

“The Tower’s not over until the ropes are on the ground,” he declared.

Ever since that trip, I’ve thought of this as Slater’s Law and I see entrepreneurs and venture capitalists publicly violate it every day. Blog posts humble-bragging about a round of financing that values a startup at a billion dollars or more, press releases touting a company’s filing of an IPO, young VCs raising a new fund on the strength of their awesome but entirely unrealized first portfolio — all of these violate Slater’s Law.

A venture-backed company is not a success until the return is fully realized by its shareholders through a sale or public offering.

An IPO is not a success until the underwriters sell shares to the public, the proceeds are in the bank, the investor lockups have ended, and there is a liquid market for these public shares at a price in excess of their offering value.

A venture fund is not a success until limited partners have received the realized proceeds from their fund managers at a multiple of their original investment, and the fund managers have cashed their carried interest checks.

The Tower’s not over until the ropes are on the ground.

It is remarkable that everywhere you go climbing or skiing in the world, you can find an IFMGA-certified mountain guide to take you there. It’s also a testament to the power and consistency of the IFMGA standard that certified mountain guides around the world have the same set of skills and competencies.

Arc’teryx  is a leading outerwear brand from Canada that has supported mountain guides in many countries over the years. They made a  video highlighting my friend,  Marc Piche , the technical director of the Associate of Canadian Mountain Guides (ACMG), guiding his clients in the Bugaboos in British Columbia, and  Andy Perkins , a storied British Mountain Guide (BMG), guiding his clients in Chamonix. Note the consistency in their approaches and the professionalism among these guides in two distant mountain zones.

In contrast, there is no international certification standard for venture capitalists. Anyone with a committed pool of capital and business card can call themselves one. Perhaps this is appropriate since the worst thing that can happen is that you lose all the money. In mountain guiding, someone could die.

In a small town like Boulder, it’s pretty easy for entrepreneurs to differentiate among VCs: the bad ones disappear quickly and the good ones last a long time. But in Silicon Valley, there’s just too much volume to decide who is likely to be a good guide for a new company. So after observing VC behavior as a practitioner for many years, here’s my cheat sheet:

Good Venture Capitalist

Forms authentic relationships

Is happy to lead an investment

Introduces you to new customers

Closes on the signed term sheet

Four to six board meetings a year

Pings you once a week with an email

Introduces you to your new CFO

Invites you to lunch for a reason, and pays for it

Wants to hear all the news, good and bad

Carefully makes commitments, and sticks by them

Finds new deals through a large network of authentic relationships and a deep understanding of technology markets

Talks about your company at every opportunity

Doesn’t seem that busy

Bad Venture Capitalist

Forms transactional relationships

Waits around for other VCs to lead an investment

Calls your customer references

Begins negotiating once a term sheet is signed

Twelve board meetings a year

Emails, texts and calls you every day

Orders a full audit of your startup from a big four

Invites you to lunch for no reason, you pay

Hates bad news and lets you know it

Never does what he says he’s going to do

Finds new deals by chasing after what other VCs are investing in

Talks about himself at every opportunity

Too busy to do anything

The mountains are a dangerous place. Clients deserve a guide that the IFMGA standard represents. Experienced entrepreneurs deserve no less.

As mountain guides and venture capitalists, it is our job to form authentic relationships with our clients and entrepreneurs. All of the value in our business comes from the effort.

The nature of these relationships can be hard to describe, and the experience can vary among participants, but they share certain common elements.

Authentic relationships are durable: guides and clients who experience success and failure together learn to rely on each other with an unshakeable trust. A first summit is a good start, but authenticity is formed over a career together, not in a single deal.

Authentic relationships have integrity: guides and clients depend upon each other to state the obvious and to understand each other’s strengths and limitations. Being the CEO of a startup is a lonely, dangerous place, but having confidence in your VC’s skill and judgment makes a difference in the outcome.

Authentic relationships involve risk: guides and clients are careful in choosing an objective because they understand that failure is a possibility and that the consequences can be fatal. Experienced entrepreneurs and VCs know when they’ve missed the mark and live to climb another day together.

Authentic relationships are complex: guides and clients know each other professionally, and while they’re sometimes good friends, their relationship is mediated by the mountains. When the climb is over they often return to their respective lives. I don’t have to endorse the lifestyle choices of an experienced entrepreneur if we share a common mission and vision of the company we’re building together.

Authentic relationships are formed through progression: it’s difficult to start out with a client on the hardest objective, let alone achieve it. Progression is an important feature of a guide and a client’s history together, and forms the basis of their shared trust. The best VCs cultivate their relationships with entrepreneurs through progressive, successful ventures. It takes years to build a great company and the best outcomes for VCs and entrepreneurs involve the long game.

Authentic relationships are rewarding: few people seek out high mountain adventures as a part of their daily lives, and even fewer devote themselves to developing the skills required for a certified mountain guide. Those that do share a love of the sport and a joy in the experience that is magnified by their partnership. While building a successful technology company is hard work, and the payday can be satisfying, enjoying the ride is a key part of what makes life together fulfilling for entrepreneurs and VCs.

Effective communication between a guide and client is fundamental to their relationship and to their shared success on the objective. The more challenging the terrain, the more important this communication becomes.

Experienced guides exhibit two characteristics that ensure clear communication in risky situations. First, they speak to clients directly and calmly with a voice and demeanor that conveys the seriousness of the situation, but also instills confidence in the client that we’ve been here before and know what to do.

Second, experienced guides state the obvious. What is obvious to a mountain guide might also be obvious to a client (e.g. “the weather is good today”), but it might not be (e.g. “don’t step there, it’s loose”).

Marko Prezelj  is the greatest Slovenian alpinist of my generation and has been awarded the  Piolet D’Or  three separate times for his cutting-edge first ascents around the world. Marko is a great mountain guide and a truly entertaining guy to hang with, but when the rope comes out it’s all business.

If the conversation strays off topic or becomes distracting, if the language isn’t clear and direct, or if the parties won’t say what they mean for fear of insult, Marko shuts it down:

“No tasty talk,” he says.

Marko’s command is especially relevant in the boardroom. Peter, Jonathan and I have spent our careers listening to insecure entrepreneurs fumble to explain the big plan miss, and to their wordy, self-absorbed investors who cannot shut up.

One of our heroes,  Dick Kramlich , the founder of NEA, once told Peter that he thinks about what he says in the boardroom with a single standard in mind: will my comment or suggestion make a material impact on the company’s trajectory? If not, keep quiet.

Experienced VCs state the obvious and, no matter how uncomfortable the subject, put it in front of everyone at the table in clear, precise language. Great entrepreneurs embrace this approach and speak to their teams in the same professional manner, even when the message is painful to hear.

The result is a healthy culture in which guides and clients understand each other with fidelity and trust each other to state the obvious.

One of the characteristics of great entrepreneurs is that, to a person, they are ruthless sandbaggers. Great entrepreneurs consistently under-promise and over-perform, and through their example, inspire this behavior throughout their organizations.

The same is true of great climbers, none more so than one of the greatest American rock climbers,  Henry Barber .

From 1975 to 1980, Henry was the best rock climber in the world. He was excellent on his home crags of  Cathedral Ledge  in New Hampshire and the Shawangunks of New York, where he established and repeated the hardest climbs of the day. More importantly, Henry was the first rock climber of his generation to travel in search of the hardest routes in the world.

Everywhere Henry went in those days he met up with the best local climbers and established a first ascent with them in impeccable style, which then became the hardest climb of their crag. Afterward, Henry and the locals would decamp to the nearest pub to celebrate their achievement, and Henry would drink them under the table. The next day, bright as a daisy, off he’d go to the crag to set another new standard.

After a few seasons of this, Henry had a reputation and everyone knew what to expect when he showed up. People began pointing Henry toward climbs they knew were dangerous or impossible, encouraging Henry to give it a try. Given his intelligence and talent for self-preservation, Henry frequently demurred.

But just as often, Henry knew what others didn’t: he was so good at rock climbing and he had experienced the same scenario in so many different places around the world that he could see what others could not. Henry would then climb the new route on sight and blow the locals away.

Henry Barber exemplified the ideal of sandbag excellence.

We are constantly teaching this lesson to less experienced entrepreneurs, who are optimists by nature and inclined to over-represent the promise of their venture to the detriment of their cash position and to their longevity as a CEO.

Instead, our great serial entrepreneurs have embraced this lesson and practice it every day.

If she thinks the likely outcome is a 10, she tells the Board it’s a 6, and surprises everyone on the upside, even if the results fall short of her estimate. She leaves a couple of things in her pocket every quarter because she never knows when she’ll need them. She does this for all the goals of her team and for her company, and in doing so, creates a culture of sandbag excellence.

A classic clip from 1976 : Henry ruthlessly sandbagging Pete Livesey, the best British rock climber of the time, on his own route, Dream/Liberator in Cornwall, England.

“The true value of things resides in their soul. The physical object itself doesn’t have much importance. It’s the use we make of this object that is its true value.”  Peter Stelzner, Chamonix Ski Artisan

At the dawn of mountain guiding, late 1800s through the start of WWII, it wasn’t hard to identify the mountain guides — they were the guys that led the way to the top of the peak, often dragging an English client behind them. But with the rise of professional guiding in the Alps and Canada following WWII, many national guide organizations made beautiful pins for their members. Mountain guides could display these pins while climbing with their clients, thus distinguishing themselves from the amateur enthusiasts that began to crowd the peaks in the post-War era.

The Swiss were early and prolific producers of guide pins, representing the guiding cantons of Berne, Uri, Valais and Grabunden. These pins, along with the pin of the Swiss National Guides Organization ( SBV ), adorned professional Swiss Guides as early as 1960. Adjacent alpine guides observed their Swiss colleagues with envy and quickly travelled back to their own valleys in Italy, France and Austria to produce pins of their respective collectives. Since these pins were worn only by unions whose members had passed the rigorous standards of mountain guide training first initiated by the Swiss, they became cult items throughout the late 1960s and early 1970s. A French pin in Chamonix or an Austrian pin in St. Anton virtually guaranteed a guide the attention of the most beautiful woman present a  Le Bar National  or  Mooserwirt .

As early participants in professional guiding, the Canadians ( ACMG ) were quick to produce their own pin in the 1970s, mostly because the burgeoning heliski industry in British Columbia recruited dozens of Swiss, Austrian and French pin-flouting foreigners to the remote heliski lodges.

Guide pins flourished in Europe throughout the 1970s and into the late 1980s as new countries were added to the International standard, and as their members eagerly sought to display their status to others. Germany, Sweden and Norway all produced pins of this era. Even communist Slovenia felt compelled to produce a pin, albeit a dour Stalinist version. Soon, visiting guides with homeland pins chased after the same groupies in Zermatt as the landed Valais guides who called the valley home for generations, often with noteworthy success.

The Swiss did not like this.

So beginning in the 1990s, Swiss guides of every canton began sporting the  IFGMA  pin as an indication of their lofty certification as the international standard. Once again, their fellow guides from Tyrol and Haute Savoie quickly followed suit, and by the summer of 1992 one could not tell the French from the Swedes, the Germans from the Canadians. The rapid adoption of the IFMGA pin by member country guides in the 1990s once again leveled the playing field for the Swiss in their amorous pursuits, and there was soon peace among the lucky members of this elite, international society of guides.

All of this guide pin stuff had sorted itself out long before the application of the  American Mountain Guides Association  to the international standard in 1997. When we were finally accepted to the IFMGA as a full member in 2001, the AMGA had produced a series of lame pins for each discipline for several years. All of these became obsolete the minute the U.S. joined the IFMGA.

You see, prior to the advent of the IFMGA pin, a local mountain guide would rather give you his pinkie than his guide pin, a badge he paid for literally in sweat and blood. This was no tourist souvenir, and could not be bought anywhere, for any amount of money. It was a heritage, a tradition, a way of life for generations of alpinists whose families pioneered the great routes of their valleys, and who earned a living taking visitors to the summit of their home peaks.

When I joined the Board of the AMGA in 2001 at the invitation of  Phil Powers  and  Dick Jackson , I insisted on a new pin classification, Lifetime Member, which recognized individuals (like me) who were fully certified to host a Board dinner, but little else. While it gave me no status to speak of, my Lifetime pin enabled me to barter with visiting mountain guides for their cantonal or country pin. I found this exchange was most effective during international guides meetings, about the time the third bottle of vintage Burgundy was opened.

By this time, the IFMGA pin was well established, and the local guide pins were relegated to the cigar box. Mind you, no one was anxious to dispose of them, and no full guide would ever give one to a client under any circumstances. But these beautiful reminders of our provincial roots could be shared with another guide under the right circumstances.

I began collecting guide pins in earnest when I joined the AMGA board, and now possess the finest collection in the world. Each was given to me by a fellow mountain guide after a memorable climb on my terrain or theirs, and many were from the Head Guide of the representative region. Some are antiques; others were produced by IFMGA member countries at my request. In each pin there is an adventure that I treasure and a mountain guide that I admire.

Venture capitalists and mountain guides are risk managers. They use their experience and talent to bring order and success to an otherwise chaotic and dangerous endeavor. They do not, as a rule, manage people and to be truthful, they tend not to be very good at it. Instead, they embark on a plan with input from others, manage the situation as it evolves, and strive to deliver the best possible outcome available to the participants under the circumstances.

On some days, that’s the summit; on others, it’s failure and a long walk home.

In every effort, luck and timing play a major role for both guides and VCs. The best entrepreneur, surrounded by seasoned management, financed by top-tier firms, and laser focused on a fast growing market with a best and first in class product can fail utterly — it happens to us all, with depressing regularity.

The most experienced guide, leading a longtime client into his terrain with perfect conditions and high stability, can trigger an avalanche with devastating consequences. There’s no rhyme or reason; it’s just bad luck and the results are deadly for the client and debilitating for the guide. Most of the great mountain guides I know have lost a client under these circumstances, and a few have lost their own lives as well.

With superior knowledge of the terrain and weather, a detailed history with the client, and years of experience, guides can reduce the risks of an ascent, but they cannot eliminate them. Risk looms over us every day in the field, influencing our choices, and reminding us of its brutal consequences.

I’ve heard young entrepreneurs criticize an experienced VC as “risk averse,” a job description I regard as fundamental to the exercise. Getting run over by the lucky truck early in one’s career is a great start for many young VCs, but durability depends on the prudent management of other people’s money, not on taking imprudent risks.

As a member of a portfolio company’s Audit Committee, I once approved the investment of our excess cash in Auction Rate Securities, rated AAA by Moody’s and advertised by underwriters as “the same as cash.” In 2007, the auctions froze, the underwriters (Lehman Brothers in this case) went bust, and it turned out these instruments were issued by offshore insurance companies with questionable finances.

By all rights, I should have been killed in that avalanche, buried under my “safe” investment in Auction Rate Securities. That the same avalanche cycle buried hundreds of my peers under the same pile of worthless securities did nothing for my shame then, and I’m now grateful for the lesson lived: the excess cash on the balance sheet of my portfolio companies is invested in securities with the explicit guarantee of the Federal Government of the United States, period.

There is no such thing as safe.

At Boulder Ventures, we’re proud of our long association with  Canadian Mountain Holidays  (CMH), the world’s premier heliski company. CMH operates 14 remote backcountry ski lodges in the Columbia Mountains of Canada, and is the largest employer of mountain guides in the world. CMH’s world headquarters were located in Boulder Ventures’ offices for a long time, and although we don’t have a financial interest in CMH, we’re good customers and good friends with their guides.

We’ve learned a lot from the CMH guides over our years together in the field, and one of them is to disseminate information about mistakes throughout our organization and portfolio companies. That way, when we do make mistakes, they are Original Mistakes, not the same ones other people have already made.

My favorite Original Mistake from CMH is the story of the Haggy:

Before he was head guide at CMH, Erich Unterberger ran the  Adamants Heliski Lodge  for two decades. Each week over the winter season, Erich and his staff moved 44 guests and all of their luggage from the parking lot on the Goldstream River to the Adamants Lodge, 30km away.

CMH guests have a lot of luggage.

Adamants guides did this for years using the 212 helicopter that takes us heliskiing, which is fine for moving guests around, but is an expensive way to move their luggage. Erich reckoned that moving the guests’ luggage up and down to the Adamants Lodge in a tracked vehicle would be way cheaper than flying the stuff around in helicopters. He found an articulated Swedish Army Vehicle called a  Haggy  on eBay, bought it, and began using it to ferry the luggage on transfer days.

This was an ingenious solution to a long-standing problem, and Erich got all the credit for saving CMH a bunch of money while improving the logistics and guest experience on an otherwise hectic transfer. The Haggy ran all season without incident, driven up and down the Goldstream logging road by one of the Adamants staff we called “Lawnboy.”

One day, Lawnboy was moving the guest luggage in the Haggy when a red light went on. All of the Haggy controls were in Swedish and, unfortunately, Lawnboy didn’t speak that language, so he just kept driving. Pretty soon, Lawnboy smelled smoke and stopped to look around. He found the back of the Haggy on fire and alertly offloaded all of the guest luggage before the whole thing burst into flames and burned to the ground.

Peter Roshko, my partner at Boulder Ventures, and I took a ski tour in Zermatt in 2011 with our Swiss partners,  Dominik Meyer  and  Uli Geilinger . Zermatt is the birthplace of mountain guiding, and we were privileged to have as our guide  Hermann Biner , the President of the IFMGA (International Federation of Mountain Guide Associations). In our hotel room in Zermatt the night we arrived, Peter and I noticed a framed summit photo. I took a picture of it since it seemed important.

When I showed it to Hermann on the first day of our tour from Zermatt into Italy, he recognized the older guy in the photo as  Uli Inderbinen , a famous Zermatti guide that climbed the Matterhorn more than 300 times. Hermann said the photo was a Matterhorn summit shot of Uli at age 90, the oldest guy to ever climb it.

When we returned from our tour, Peter and I had dinner in Zug with  Leo Caminada , another revered Swiss Guide. Leo also recognized Inderbinen, and remembered that he took this photo the day of the 125th Anniversary of the Matterhorn’s first ascent, a day that Leo guided the President of Switzerland to the summit as well. Peter loved that story.

Bergfurher Inderbinen possessed one of the most important qualities in a successful mountain guide: durability.

We guide our clients on good days and bad, sometimes to the top, sometimes not. We learn every time we succeed and every time we fail, but most importantly, we always return to climb again.

In mountain guiding and in venture capital, durability is the key to success.

It takes a long time to understand how to guide your range properly, to develop a deep repertoire of routes that you can offer clients, and to understand their strengths and weaknesses. It’s only in retrospect that we can bring perspective to these experiences, and to do that you have to survive long enough to develop those skills.

Great VCs know when to charge with their entrepreneurs when the conditions are right, and when to back off when they’re not. They guide their clients in good seasons and bad, and because of their reputation for consistently reducing risk and maximizing returns, they attract the best clients. After many years of guiding on their terrain, guides develop a combination of intuition, experience, pattern recognition and a deep client roster that proves unbeatable in the mountains.

They achieve durability.

One of the most experienced and durable mountain guides in the world is my friend and climbing partner Erich Unterberger. Erich ran the Adamants Heliski Lodge for CMH (Canadian Mountain Holidays) for many years, and is now the Head Guide for all of CMH’s heliski operations in Canada.

CMH made a  short video  of Erich guiding in the Adamants in the summer, in which he honors Inderbinen as his hero, and I now understand why.

I have been investing in startups since 1985, and guiding since 1976. After 60 portfolio company investments from 11 different venture funds that I’ve managed, and after guiding hundreds of clients in the mountains of Colorado, Canada, and Europe over the past 40 years on skis and on rock, I’ve come to this conclusion.

A mountain guide is faced with three factors that determine the success or failure of his objective: the Client, the Weather, and the Route.

The Client is always the most important factor. To know a client’s true abilities and limitations, a guide must spend time with her in the field. Over the years, through multiple, progressively harder routes, the client and guide form a relationship that drives the likelihood of their shared success on the next objective.

Clients choose their guides because of their extensive local knowledge of the terrain, and because the guide has climbed a route the client has never done many times. While achieving the summit depends on a successful partnership, that likelihood is higher with an experienced guide, and the possibility of injury or death is dramatically reduced. Experienced guides have seen all the failure modes that clients will encounter on the route, and they know how to avoid them.

The Weather in the mountains is constantly changing, but an experienced guide can accurately forecast his local weather and anticipate the best days. Some objectives are possible even in bad weather, and a good guide has these in his pocket when the client’s schedule can only work on specific dates.

The Route is the trade of the guide, and the place where his expertise is most apparent. Many guides spend their professional careers guiding one route: the Hornli Ridge of the Matterhorn; the West Buttress of Denali; the South Col of Everest; the Nose of El Cap. These guides have a narrow focus on a single objective, but their skill and judgment is unmatched.

Other guides devote themselves to ski guiding a range, or climbing all the routes in a single area. Their expertise is broader, and they are able to serve a wider array of clients. Some guides take their clients on adventures around the world, but whatever the approach, mountain guides must have the experience and durability to take their clients up the route, and safely down again.

In venture capital, the Client is the entrepreneur; the Weather is the market environment; and the Route is the portfolio company. The VC is the mountain guide.

People think that VCs spend all day picking entrepreneurs, but it’s not true. Great entrepreneurs choose the VCs they work with to build their startup, and these talented clients only pick guides with whom they have the highest chance of success.

Experienced mountain guides know that their climbing days are limited, and want to work with clients who demand the biggest routes. Likewise, experienced VCs will only devote their limited time to entrepreneurs with their sights set on game-changing companies.

A VC must be attuned to the market environment throughout the investment cycle of her entrepreneur’s startup. Faced with adverse conditions or unexpected client limitations, great guides know when to fold, and live to climb another day — so it is true among venture capitalists.

Whether VCs focus their expertise on specific industries or on a specific geography, they must attract the best entrepreneurs to enjoy success. In stormy seasons or bright sunshine, great VCs can avoid the hazards that could result in failure, and find a path to success with their entrepreneurs.

I’ve spent my career as a venture capitalist trying to figure out how to get a higher hit rate from the investments we make. You only get a dozen or so deals in a small fund like ours, and we’re actively involved in each one. With this strategy, a partner can only do one to two new deals a year before he gets overwhelmed, so you quickly learn in the VC business to make every investment count. When you focus on a small town like Boulder, you get to live with your mistakes for a long time; every day, you see the consequences of your failures in the faces of local investors, employees, contractors and customers.

Venture capitalists generally like their jobs, whether or not they’re any good at it, because we’re control freaks. Ironically, being a venture investor in a startup company gives you a limited amount of control compared to other investment professionals. When you run a mutual fund or a hedge fund, you see the results of your ideas every day on the balance sheet. Even though you have no influence on the outcome, each day you can buy or sell the stock of the company you’re betting on — the ultimate in control (occasionally, cheating is a successful strategy for these investors, too).

Buyout investors own the companies they invest in, so they can change management and influence the timing and location of their exits. Mostly, they invest in operating companies that are valued as a multiple of cash flow. Compared to startups, there’s a lot of certainty investing in stable cash-generating businesses, which enables the financial engineering that is the basis of success or failure for the buyout investors.

In contrast, venture capitalists partner with entrepreneurs to conceptualize and create a novel business. Nothing is certain in a startup and while there are examples of success and failure for every business model we fund, each startup company finds its own path. In addition, and in contrast to hedge funds and buyout funds, we syndicate our investments with other investors who share our worldview and conviction, further eroding our control over an already chaotic situation.

Within this context, the lesson we have taken from our experience investing in startups is to focus on serial entrepreneurs, and on the size and trajectory of the target market — these are the keys to a high investment hit rate.

Serial entrepreneurs are a special breed and it is hard to describe what makes any individual great. We sometimes know it when we see it, but after our first experience with her, we can spot it every time. Knowing how to support, encourage, and stand beside a successful entrepreneur is the most important skill we possess as venture capitalists. I often tell our investors that nurturing an authentic relationship with our serial entrepreneurs is our most important duty and the source of value in our partnership.

We invest in companies that can create and sustain fast revenue growth. On exit, these investments are valued by the public and by strategic buyers based on revenue trajectory, not profitability. While it’s possible to create a fast growing company in an old market by introducing a better product, it’s much easier to do so in a new, fast growing market. Especially when selling to the enterprise, we make bets on markets and entrepreneurs rather than on specific products.

If you’re wrong about the size and growth of the new market, great entrepreneurs can sometimes change course (or get lucky) and still make money.

If you’re wrong about your entrepreneur, experienced VCs can sometimes change jockeys (or get lucky) and find success.

If you’re wrong about both, you get to lose all the money.

But when you’re right about the entrepreneur and you’re right about the market, it’s a beautiful thing.