Three friends. One closet. A company now valued at $10 billion, serving over 400,000 small businesses. Josh Reeves is the co-founder and CEO of Gusto, the payroll, benefits, and HR platform now valued at roughly $10 billion. But he didn't grow up dreaming of building HR software — nobody does. The son of two teachers who were the first in their families to go to college, Josh studied electrical engineering at Stanford during the dot-com collapse, when the conventional wisdom was that the internet was finished. He ignored it. After a stint as a product manager at Zazzle and a first startup he now describes as "stealth mode" — his polite way of saying he had no idea what he was doing — Josh walked away with the most important lesson of his career: never start a company just because your friends are. In 2011, he and two co-founders started Gusto to fix something genuinely broken. Payroll, benefits, and the systems that quietly reduce people to ID numbers and acronyms — especially in small businesses, where two-thirds of U.S. employers have fewer than five people and every hire is a real human being, not a line item. They set one rule: they wouldn't pay themselves until they could do it through their own product. They launched in December 2012 with 100 small businesses. One co-founder spent four months sleeping on an air mattress in a roommate's closet — it had a skylight, for the record, and the roommate's clothes were still hanging inside. Fourteen years later, Gusto has grown from three people in a Palo Alto house to over 3,000 employees ("Gusties") across Denver, San Francisco, New York, and Scottsdale — with no headquarters, by design. In this episode, Josh sits down with Jessica to unpack how he protected culture at scale, why he deliberately left revenue on the table to launch in all 50 states the right way, and the framework he uses to resist Silicon Valley's growth-at-all-costs gospel. You'll learn: - Why second-time founders have an edge — and why Josh had role, responsibility, and ownership conversations on day one - The weekly feedback walks the three founders started when they were just three people, and still do 14 years in: three things working, three things to improve - Why most systems treat people like transactions — and what changes when you build for the human moments instead - The values-and-motivation interview Gusto uses to hire for what makes someone tick, not just what's on their résumé - Why interviewing is a skill every leader should practice obsessively — and how the best interviewers dig past the first and second answer to what's really underneath - How to scale culture without freezing it: "we're not a museum" — what should persist, and what should always be allowed to change - The "no headquarters" home-base model, and why Josh personally interviewed Denver's first 10-15 hires to make it as important as San Francisco - Why "doing things that don't scale" early can build the momentum that scales later - Why he deliberately left revenue on the table to cover all 50 states comprehensively, instead of launching half-built - The three checks-and-balances Josh runs against growth: product quality and compliance accuracy, unit economics, and team retention - Why there are over 10,000 payroll rules in the U.S. — and why the business owner should never have to become the expert - How AI is a tailwind, not a threat — making Gusto more of a teammate and partner to the small business owner - Why work should be more than a paycheck: purpose, community, and impact, when the alignment is there - The thought experiment every founder should run before committing: the 10,000th time you describe your idea, will you still be excited? Whether you're starting a company, scaling one, or just trying to do work that means something, Josh's philosophy is the throughline — the one he repeats to his four kids and to every founder who'll listen: In our family, we do hard things. Truth Works is hosted by Jessica Neal, former Chief Talent Officer at Netflix, now in the business of telling the truth about how work really works.
