Ron Schneidermann knows what the grind to success can cost. Over more than two decades of startup leadership, he scaled his first company, the ski-resort marketplace Liftopia, into a business generating more than $60 million in annual revenue, went on to serve as CEO of the popular hiking app AllTrails, and today leads the test-prep startup Acely. But looking back across his career, he says he had to learn the hard way what real work-life balance costs—and what it is worth.

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

The tradeoffs 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 only a single week for the birth of his son—and considered that 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 is 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. His retrospective also underscores a pattern his own story illustrates: the costs of early-stage sacrifice tend to surface only years later, often after the milestones that sacrifice was meant to secure have already come and gone.

"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 shift in thinking was already underway. He eventually became CEO in 2019 and instituted a company-wide ritual: on the first Friday of every month, AllTrails shut down and employees were encouraged to go outside.

In August 2025, Schneidermann took on a new challenge as CEO of Acely. This time, he is applying those hard-won lessons from the start. In place of monthly trail days, the company now runs a monthly "hackathon," during which its fewer than a dozen employees pause routine work for the entire day to experiment with AI tools and new ideas—no meetings, no KPIs, no deliverables. With Acely still running on a team of fewer than a dozen, how those rituals hold up as the company grows will offer an early read on whether the lessons he carried over from AllTrails prove durable.

Schneidermann says he will never take a job for the salary again

Even before Schneidermann set his sights 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. He ended up being fired three separate times because he "never liked it" enough to muster the proper decorum.

After graduating in 2000, he landed a job at Accenture as a business process consultant. Once again, the role did not align with the life he wanted to have, and despite the lucrative salary that came with working at a Fortune 500 consulting firm, he quit.

"It was a great experience. I'm grateful for it, but I hated it," he said. "I hated it, and I told myself, I am never going to take a job for money again. Life is too short."

That realization eventually pushed him toward startups. Through a friend of a friend, he landed a role at Hotwire, then a travel startup that was later acquired by Expedia, and it became his entry point into the tech world.

Looking back, Schneidermann said that early career path offers a lesson he wishes more young workers would take seriously: relationships matter as much as résumés, especially in a job market where traditional entry-level pipelines are narrowing.

"Really invest in your network," he said. "There's a small pond at the end of the day. If you stay in it long enough, you are going to know everyone, and everyone you know are going to be leaders somewhere."

Building real relationships in the digital age

Schneidermann's advice may resonate with Gen Z at a time when employers report that early-career workers are struggling with basic professional norms. A 2024 survey found that six in 10 bosses admitted they had already fired Gen Z employees hired straight out of college, citing poor communication, lack of professionalism, and disorganization.

For Schneidermann, the issue is not just skills—it is mindset. Too many young workers treat networking as transactional, when in reality it is built on consistency, reputation, and how you show up over time. That starts with small, often overlooked behaviors.

"There's a human on the other end. Don't ghost people and just show up," he said.

The same principle applies more broadly to career growth. Rather than chasing the perfect role or obsessing over credentials, Schneidermann emphasized curiosity as the real differentiator.

"Just approach everything with a curious mindset," he added. "Just constantly try to be learning and exploring."

That philosophy has carried him through multiple career pivots, including his most recent move to Acely, a startup with no obvious connection to his background. After being approached by an executive search firm, he took the job in part because his high school–aged daughter had recently used the product to prepare for the SAT. She was one of its more than 50,000 active users.

From his perspective, he did not need to be an expert in the industry—he simply needed to be willing to learn it. For Schneidermann, the challenge was one he was eager to take on.

A version of this story was published on Fortune.com on April 25, 2026.