When You’re in a Hole: Tony Stubblebine on the Strategy, Psychology, and Lessons of a Business Turnaround

In this episode, I’m digging into the messy reality of business turnarounds, the kind where survival isn’t guaranteed and leadership is more about doing the hard, boring things than dazzling with big ideas.

My guest is Tony Stubblebine, CEO of Medium, whose recent post “Fell Into a Hole and Got Out” made the rounds for being one of the most honest and actionable stories about company rescue I’ve ever read. Tony’s background runs deep: founder of Coach.me, architect of the Better Humans publication.

This is what it’s really like to take over a company bleeding millions, shrinking fast, and staring down insolvency. But it’s also a story about staying steady, balancing the financial reality with the need to restore quality, purpose, and confidence to a battered team. There’s no sugar-coating here, just real talk about layoffs, difficult investor negotiations, and why the business model has to come before your “next big thing.”

Tony walks us through the psychological and strategic ladder he and his team built, one rung at a time, to claw Medium back from the brink. He shares candid lessons for founders, hard truths about startup mythologies, and the personal practices that kept him sane when the stakes were highest.

Here’s what we cover:

• The “hole” no one talks about: what it’s really like to inherit a company in crisis
• Brutal financial realities, cutting costs, and restoring a culture’s sense of purpose
• Why the business model now comes before the product
• The Goldilocks problem of innovation and finding the “just right” middle ground
• How to negotiate with investors when a prior deal is dead and nobody wants to say it out loud
• Lessons on hiring, layoffs, and having the hard conversations with a team that’s seen too many pivots
• The psychological “ladder” out, how to focus everyone on small wins
• The power of slow, steady self-improvement (meditation, journaling, therapy) for surviving big challenges
• Why Tony thinks each of us, just by living our lives, accumulate wisdom that can help others
• This is more than a highlight reel, it's a toolkit for anyone who’s had to make the tough calls or wondered if they could.

Enjoy the show.