Episode 595 - Second interview with David Barrett

What happens when you refuse to build your company the "right" way?

Ron and Ed welcome back David Barrett, founder and CEO of Expensify, to discuss the unconventional thinking that transformed a simple expense reporting app into a publicly traded fintech platform. From bootstrapping product-led growth and rejecting traditional enterprise sales models to building a culture around engineering, experimentation, and long-term thinking, David shares why questioning accepted business wisdom has been central to Expensify's success. The conversation explores innovation, leadership, AI, remote work, company culture, and why sometimes the best strategy is to ignore conventional advice and solve the problem that's actually in front of you. Whether you're an entrepreneur, accountant, or business leader, this episode offers a fresh perspective on building companies that last.

Guest Bio

David Barrett is the founder and CEO of Expensify, the expense and financial management platform he launched in 2008. A lifelong programmer and computer engineer, David previously led engineering at Red Swoosh before its acquisition by Akamai. Under his leadership, Expensify has grown into a global fintech company serving millions of users and became a publicly traded company on Nasdaq in 2021. He is widely recognized for his unconventional approach to technology, leadership, and product innovation.