Not Another CEO Podcast | Bootstrapping to Success - Sean Griffey - Industry Dive

Bootstrapping to Success - Sean Griffey - Industry Dive - Episode #39

April 15, 2025 / 59:33/E39

What happens when you combine relentless focus with long-term trust and bootstrapped grit? In this episode of Not Another CEO Podcast, David Politis chats with Sean Griffey, the co-founder and former CEO of Industry Dive, a digital media company that went from humble beginnings to a $500M+ acquisition.

Sean dives into how simplicity became his core operating principle, the creative strategies behind building a strong team, and why bootstrapping gave him the ultimate freedom. He also opens up about co-founder dynamics, the emotional challenges of scaling leadership, and finding clarity after stepping down.

Takeaways:

Start with Simplicity, Scale with Clarity: Sean shares how simplicity became a guiding principle across operations, sales, and product. By constantly asking “How can we make this easier?”, Industry Dive streamlined execution and scaled effectively across 30 different markets.
The Coffee Challenge That Built Culture: To foster cross-team collaboration, new hires were given a $50 coffee stipend and a list of quirky and strategic questions to ask people outside their department. This initiative not only built early camaraderie but also helped break down silos before they could form.
Bootstrapping with Intent (and $400K): While Industry Dive raised a small angel round, Sean considered the business bootstrapped and didn’t pay himself for 18 months. He talks about resisting early VC offers in favor of building profitably and why media businesses need time, not acceleration.
Strategic Exit Through Private Equity: Sean shares how the PE partnership offered strategic guidance, operating support, and true alignment on growth goals.
The Leadership Challenges No One Talks About: Sean reflects on the difficulty of maintaining culture and connection at scale, especially through the pandemic. He emphasizes the importance of transparency, weekly all-hands, and honest company-wide Q&As—even when the questions were tough.
Letting Go and What Comes Next: After stepping down as CEO, Sean is still adjusting. He shares how he's staying engaged and how he’s giving himself space to figure out what’s next with no pressure.

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