Lawrence Hester

I started my career on the trading desk at Credit Suisse. Three years of spreadsheets and Bloomberg terminals taught me one thing: I needed to build something of my own. So in 2009, I started a company selling croutons. Yes, croutons. It didn't make me rich, but it made me an entrepreneur.

In 2013, I co-founded FareHarborwith a conviction that the tours and activities industry deserved better software. We built it into the dominant booking platform in the space — from a handful of people to 500+ employees, from zero to tens of thousands of operators worldwide. In 2018, Booking Holdings acquired FareHarbor.

After the acquisition, I spent years as an advisor and investor, learning what I wanted to do next. The answer came in 2025: I came back as CEO of Expedition Software, the parent company of Rezdy, Checkfront, Regiondo, and Manifest — four brands, three continents, one turnaround mission. The goal is simple: build the largest software platform in tours & activities. Again.

The Mountains

Somewhere along the way, I started running. Not the “5k on Sunday” kind — the kind where you run through the night in the Alps and question every decision you've ever made.

My first ultra was the Bear Chase 100km in 2017. I dropped at 50 miles after atrial fibrillation during training forced me to recalibrate. I came back for Adamello Ultra Trail 100K in 2024, then Lavaredo Ultra Trail 120K in 2025, and finally UTMBlater that summer — 171km around Mont Blanc, finished in 38 hours and 22 minutes. I'm training for UTMB 2026 now.

Running ultras and running companies are the same discipline. The mountain doesn't care about your plan. Neither does the market. You adapt, you endure, you keep moving forward. That's the whole game.

DWIFT

Do Whatever It Fucking Takes.It's the motto for everything — the company, the mountains, the life. Not recklessness. Not grinding yourself into dust. It means showing up fully, staying honest about what's not working, and doing the hard thing when the hard thing is the right thing.

What I Write About

This blog sits at the intersection of endurance and leadership. Lessons from the boardroom and the mountain. Race reports that double as business strategy. Honest reflections on building, failing, rebuilding, and running really far.

The Personal Stuff

I live in Milan, Italy with my wife Marina and our three kids — Paloma, Lolo, and Viola. We moved from Hawaii to Denver to Amsterdam to Italy, which is either a great adventure or a sign that I can't sit still. Probably both.

Work With Me

I advise tour & activity companies on growth, product, and operations. I also speak on leadership, the endurance mindset, and building companies that last. If any of that resonates, reach out — lawrence.hester@checkfront.com.