Between Two Founders #6: Gusto Co-founder & CEO Joshua Reeves
Gusto Co-Founder and CEO Joshua Reeves sits down with Jeff Seibert, Co-Founder and CEO of Digits, to share behind-the-scenes challenges, pivotal moments, and valuable lessons learned towards building a category defining company.
Josh didn’t just build an HR, payroll, and benefits company—he reimagined how small businesses support their teams. From driving across the U.S. in an RV to meet customers face-to-face to championing a no-shoes culture at Gusto HQ, his approach to leadership has been anything but conventional.
Under Josh’s leadership, Gusto has grown to serve over 400,000 businesses nationwide, processing tens of billions in payroll while helping companies create thriving workplaces. But success didn’t come overnight. In this exclusive conversation, Josh will reveal the early struggles, bold bets, and defining choices that shaped Gusto’s rise.
What to Expect:
The story behind Gusto’s launch and its mission to simplify payroll and HR
Lessons from scaling a startup into an industry leader
The power of customer obsession—and why Josh took to the road to meet them
How company culture fuels innovation (yes, even down to the no-shoes policy!)
Insights for founders building in competitive, entrenched markets
Join us for an inspiring, unfiltered discussion about building with purpose, embracing unconventional tactics, and what it really takes to redefine an industry. 🚀
By invitation only—apply today to attend!
Be sure to follow, like, and subscribe wherever you listen to podcasts:
Please note that the event will be recorded for later broadcast. By RSVP'ing, attendees accept that they may be captured on camera.