We’re bringing you a rerun of one of our most well-received episodes, featuring the incredible insights from serial entrepreneur Hiten Shah.

What happens when the ultimate startup veteran joins a 3,000-person company after 20 years of founding his own?

In this candid conversation, Mercury CEO Immad Akhund and serial founder Raj Suri sit down with Hiten Shah (Crazy Egg, KISSmetrics, Nira—acquired by Dropbox) for an honest exploration of founder identity, business fundamentals, and the reality of life after exit.

Hiten brings a unique perspective as someone who's built both venture-backed and self-funded companies, including Crazy Egg, which has been running profitably for over 20 years. The discussion covers his contrarian takes on fundraising strategy, why he believes "there's no better hack to product market fit than someone else's product market fit," and the surprising challenges of transitioning from founder to employee.

The conversation explores practical frameworks for choosing customers, the hidden truths about venture-backed versus bootstrapped companies, and why Hiten's official title at Dropbox is "Chief Troublemaker." Whether you're building your first startup or considering an exit, you'll gain insights from three founders who challenge conventional wisdom while sharing hard-won lessons from decades of company building.

This episode offers essential lessons for entrepreneurs at any stage, covering everything from the psychology of startup building to the practical realities of product-market fit, customer development, and maintaining founder DNA within larger organizations.