This CEO lived on canned soup and took just two days off for his daughter’s birth. Now, he admits he lost sight of proper work-life balance

The grind to success can be long, punishing, and it can quietly take more than it gives.

After scaling his first company, Liftopia, into a business with more than $60 million in annual revenue, he went on to become CEO of AllTrails, the popular hiking map app. Today, he leads test-prep startup Acely . But looking back across his career, he says he had to learn the hard way what real work-life balance actually costs—and what it’s worth.

While building Liftopia, a digital marketplace for ski resorts, that mindset came at a personal price. Schneidermann worked out of a cramped San Francisco apartment, turned spending less than $15 a day into a kind of endurance test, and went two years without taking a salary, surviving largely on canned soup.

The tradeoffs even extended into his family life. When his first daughter was born four years into Liftopia, he took just two days off work. Three years later, he allowed himself just a week for his son’s birth—and thought that was progress.

“I look back, I was just able to justify it as ‘that’s just part of the grind’… but you never get that time back,” Schneidermann told Fortune . “That was a mistake.”

It’s not an easy admission in startup culture, where sacrifice is often worn as a badge of honor and overwork is normalized as the price of ambition. But Schneidermann, now in his late 40s, has since reframed the experience entirely.

“For everything that was frustrating, that went wrong, that I regretted about Liftopia, I was able to take the inverse and turn it into a strength,” he said.

By the time he joined AllTrails in 2015, that mindset shift was already underway. He eventually became CEO in 2019 and instituted a company-wide ritual: the first Friday of every month, AllTrails shut down and employees were encouraged to go outside.

In August 2025, he took on the new challenge of becoming CEO of Acely. This time, he’s bringing those hard-won lessons with him from the start. Instead of monthly trail days, the company now runs a monthly “hackathon,” where its less than a dozen employees pause routine work for the whole day and experiment with AI tools and new ideas—no meetings, no KPIs, no deliverables.

Even before Schneidermann had his eyes on entrepreneurship, he was learning career lessons the hard way.

In the late 1990s, he was a student at UCLA studying mass communication and business while also working at Abercrombie & Fitch to help pay for his studies. However, he ended up getting fired three separate times because he “never liked it” enough to muster the proper decorum.