10 Surprising Things I've Learned Since Stepping Down as Stack Overflow CEO

After years at the helm of Stack Overflow, I decided to pass the baton to a new CEO and embrace a different kind of chapter. Many of you have asked what I'm up to now, so here's a look into my current world—a mix of board roles, new ventures, and surprising discoveries. Here are ten things that have defined this transition.

1. The CEO Succession Experience

Handing over the reins to Prashanth Chandrasekar has been a humbling experience. I still join customer calls and have weekly check-ins, but the shift in workload is massive. Watching him reorganize the company—for the better—has taught me just how much I didn't know about running a midsize business. It's oddly satisfying to root for his success; if he proves to be a better CEO than I was, that's the best outcome for everyone, including me.

2. Rediscovering Free Time (But Still Busy)

You'd think retirement means endless leisure. In reality, I'm busier than ever—but now I choose my projects. This phase feels more like a sabbatical than a retirement. I'm diving into new challenges, from board meetings to mentoring startups. The freedom to allocate time to what truly excites me is a luxury I didn't fully appreciate until now.

3. Chairman of Three Companies

My chairman roles keep me engaged with three distinct organizations: Stack Overflow, Glitch (formerly Fog Creek Software), and HASH. Each offers a unique perspective on technology and community. Balancing these hats has sharpened my ability to switch contexts rapidly—something I missed when I was focused on a single company.

4. Stack Overflow's New Leadership

Stack Overflow is in great hands with its new CEO. Prashanth's approach to growth and culture is refreshing. I still love the company and its mission, but I'm learning to step back and let fresh eyes steer the ship. The transition has been smoother than I expected, thanks to a strong team and a clear vision for the future.

5. Glitch: A Platform for Everyone

Under CEO Anil Dash, Glitch has grown into a friendly community for building web apps. Millions of apps have been created on the platform, and recent funding will accelerate that. I believe every era needs a simplified coding environment—one where developers don't need complex Git branches or multistep deployments. Glitch targets that quiet majority who just want to write code and see it run.

6. HASH: Building the Future of Simulation

HASH is still flying under the radar, but we recently published a detailed website. The mission? An open-source platform for running simulations. Imagine modeling city traffic without needing a closed-form formula—just define how each agent behaves and let the simulation show you results. This approach is computationally heavy but incredibly powerful for problems like optimizing bus routes or predicting disease spread.

7. The Joy of a Sabbatical (Not Retirement)

I've decided to call this time a sabbatical rather than retirement. The word matters. A sabbatical implies growth, learning, and eventual return (even if that return is to new projects). I'm exploring ideas, writing code for fun, and even considering a few secret side projects. The label keeps me open to change rather than feeling like I've closed a chapter.

8. Life in Manhattan's NORC

I live in what's jokingly called a NORC (Naturally Occurring Retirement Community) in Manhattan. The neighborhood is full of retirees, but I fit right in with my active schedule. It's a quiet, walkable area that provides a nice contrast to the frenetic pace of startup life. Sometimes the best ideas come during a slow stroll past brownstones.

9. A New Office Mascot: Cooper the Dog

Meet Cooper, my two-year-old corgi mix. He's become an unofficial mascot for my new ventures. If any web app needs a friendly face, Cooper is available for hire (treats accepted). He reminds me that work doesn't have to be all seriousness—sometimes a wagging tail is the best productivity hack.

10. Reflections on Running Medium-Sized Companies

Stepping away has given me clarity about my own leadership. I now see that I was too involved in daily operations. Watching others take charge—whether at Stack Overflow, Glitch, or HASH—has been a masterclass in delegation. The art of letting go is hard, but it's essential for any founder who wants their company to outlive their own tenure.

This sabbatical-turned-adventure has been full of surprises. I'm grateful for the chance to learn again, to mentor, and to build from the sidelines. If you're contemplating a similar transition, my advice: embrace the unknown, find joy in watching others succeed, and always keep a dog nearby.