Finding the Window — Boulder Ventures Ltd.

Founders face a high probability of failure in their startup journey. Even for the most experienced and talented teams, the chances of success are low. Startups fail for a myriad of reasons: adverse conditions, team dynamics, bad timing, or all three. The same challenges face alpinists who embark on an uncertain and demanding mountain objective.

The two startups that I co-founded, HotelNet and BroadHop, provide a relevant case study. Both were important projects led by experienced people. Hotel Net powered broadband services in hotels and airports, while BroadHop’s mission was to enable mobile subscriber connectivity.

HotelNet was hitting its stride in 2001, providing internet service to 120,000 Marriott, Sheraton and Hilton hotel rooms with no signs of slowing down. Then the telecom bubble burst, the company was not cashflow positive, and investors ran for the door. We sold HotelNet under duress and produced a poor outcome for shareholders. Our competitor, Wayport, survived the telecom bust and was sold several years later to AT&T for a venture-like multiple. Luck and timing matter.

In the case of BroadHop, we built a lasting business based on our original mistakes at HotelNet: make a good product, keep your customers and employees happy, and manage your cashflow. This formula works in all market conditions.

With this philosophy, the BroadHop team navigated market pivots, product reboots and a round of venture capital from Boulder Ventures and Peninsula Ventures. When the iPhone came to market, mobile data exploded and BroadHop had the right product at the right time. Cisco acquired BroadHop in 2013, providing a venture-like multiple, and BroadHop’s technology became the core of Cisco’s 5G strategy for the next decade.

*Kishen delivering a keynote at Cisco’s 2019 sales kickoff. Photo: Noa Gil-Bar*

This history is relevant to my recent ascent of the Cassin Ridge on Denali. Established in 1960 by legendary alpinist, Ricardo Cassin when he was 52 years old (the same age as me!), the Cassin Ridge was considered the most elegant unclimbed line on North America’s highest mountain. Bradford Washburn, the first ascensionist of Denali’s standard route, the West Buttress, described the Cassin Ridge as the "last and probably the most difficult and dramatic of all potential routes" on the mountain.

I attempted the Cassin Ridge in 2023 with my climbing partner and BV LP, John Thomson, and wrote about our experiences in Markers and Margins. Though Cassin-worthy conditions were never present, we managed to climb the West Buttress and honed our framework for a future Cassin ascent: alpine fitness, team chemistry and a reliable weather window.

When BV LP Chris Warner, invited me in 2026 for the same mission, I jumped at the opportunity for another attempt of the Cassin, joining Chris and Smile Mountain Guides founder, Jeff Mascaro.

*BV LP Chris Warner, the second American to climb all fourteen 8000m peaks, manning the “Life Boat” cook tent at 14,000 feet on Denali. Photo: Kishen Mangat*

Chris, Jeff and I spent severeal days waiting in Talkeetna for a flight onto the glacier, then hauling sleds, establishing camp, carrying loads, acclimatizing, and watching weather forecasts. Most of the work was in preparation for an opportunity that might never materialize. After fourteen days on the glacier, the window arrived. Unfortunately, Jeff and Chris had run out of time and had to depart.

I elected to extend my trip to take advantage of the forecast and teamed up with two alpinists from Chamonix that I had met in Talkeetna: IFMGA guide Tom Grant and IFMGA aspirant, Freja Shannon.

*Tom and Freja enjoying the splitter weather at the hanging glacier bivy, ~14,000 feet on the Cassin Ridge. Photo: Kishen Mangat*

Spending two nights and three days climbing on the South Face of Denali, we encountered good weather and excellent climbing conditions. Despite being a newly formed team, our climbing styles shaped by Boulder’s and Chamonix’s respective ethos created great team chemistry. We mostly simul-climbed in good style through the Japanese Couloir, Cowboy Arete, Rock Bands and other classic features of the Cassin Ridge and summited Denali on June 5, 2026.

*Simul-climbing the Cowboy Arete. Photo: Kishen Mangat*

Like BroadHop, our ascent of the Cassin Ridge required years of preparation, patience, and favorable conditions. We couldn't control the weather, who we would meet in Talkeetna, or when the route would come into condition. But we could control whether we were ready when those variables finally aligned.

At Boulder Ventures, we spend years helping our serial entrepreneurs build products, recruit teams, win customers, and navigate changing markets. Like hauling loads on Denali's Kahiltna Glacier, our hardest work happens long before any successful outcome.

Our best realizations emerge when company performance, buyer interest, competitive dynamics, and market conditions align simultaneously—when the window finally opens. Like a Denali weather window, these opportunities cannot be forced. We can only anticipate them and prepare for them.

Preparation doesn't create the window, but it determines whether you're capable of stepping through it. Our teams that succeed are the ones that have already done the hard work. In both venture capital and alpinism, success belongs to those who prepare relentlessly, wait patiently, and move decisively when the moment finally arrives.