Bootstrapping to Success - Sean Griffey - Industry Dive

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.

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