How to Stay Customer-Obsessed and Never Investor-Obsessed in Running Your Business with Rand Fishkin

Rand Fishkin built Moz from a struggling web-design agency into a $60 million software company and watched venture capital quietly turn it from a business that served customers into one that served investors. His verdict, over pineapple empanadas: raising VC was the second-biggest mistake of his career. The biggest? Stepping down as CEO. Rand co-founded SparkToro after Moz and now builds "customer-shaped" companies funded by friends, not funds, including a brand-monitoring tool with no AI in its marketing and a 1960s-Italy video game. He's candid about founder depression, the gap between promised and delivered equity, and why he once wrote $700,000 in personal checks to his former employees. This is a founder-to-founder conversation about doing it differently and why that might be the only honest way left. What you'll take away: • Why Rand calls stepping down as CEO his single biggest career mistake and what he'd do instead • How VC funding shifted 80% of his energy from product to pitching • The "true lifetime value" math VCs ignore (and how it warps what you build) • Why he wrote $700K in personal checks when Moz finally sold • The SparkToro clickstream data showing search still outgrowing AI • His low-risk, friends-as-investors funding model that repaid backers in 5 years • The belief 99% of founders would disagree with and how it changes how he runs companies Subscribe to Founders & Empanadas for candid, founder-to-founder stories. Watch on YouTube, listen on Spotify and Apple Podcasts.