Breakthroughs

It’s a special moment in entrepreneurship and in climbing when setbacks and persistence finally yield to progress. Breakthroughs require careful preparation, learning, and the willingness to show up until the conditions, the team, and the strategy align.

The Moment of Decision. BV LP John Thomson on El Capitan in 2017, just before bailing off the Shield in a rainstorm. Photo by the author.

I’ve experienced this in two worlds that have shaped my life: startups and climbing. As a founder of WebMessenger, HotelNet, Amigo Sytems and BroadHop, each company brought lessons, modest wins, and setbacks, but BroadHop in particular taught me the value of persistence and pivoting.

The Business page in the Denver Post in late 2000, days after the author laid off dozens of employees to save HotelNet during the dot-com bust.

Despite a solid technology platform, BroadHop struggled for years to find its footing. Our breakthrough came when we made a decisive move into the mobility market just as the iPhone transformed how people connected to the internet. That pivot aligned our capabilities with a rising tide, and in 2013, Cisco Systems acquired BroadHop. The acquisition wasn’t just the result of one good idea. It was the culmination of years of trial, error, and adjustment that ultimately prepared us to seize the opportunity and enabled our breakthrough.

It’s the same for me in climbing. In August 2025, I completed The Shield on El Capitan in Yosemite, a climb that had defeated me on three prior attempts. Each failure had its own cause—rainstorms, insufficient preparation, even injury. On my fourth attempt, the weather once again turned against our team, this time bringing blistering heat.

Dr. Joe Forrester committing to the Shield Roof, August 2025. Photo by the author.

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.