7 Things to Know About My Post-CEO Life

After stepping down as CEO of Stack Overflow, I've entered a new chapter that's part sabbatical, part discovery. This list explores the key aspects of my life now—from watching a new leader take the helm to diving into fascinating projects. Here are seven insights into what happens when you step back from the corner office.

1. Watching a New CEO Succeed Is Surprisingly Satisfying

Prashanth Chandrasekar has been in the role for a couple of months, and I'm still joining customer calls weekly. But the real joy? Realizing how little I knew about running medium-sized companies. He's rearranging everything for the better, and the best outcome for me is if he proves what a bad CEO I was by doing a much better job. It's a humbling, rewarding experience—and it frees up my time for other pursuits.

2. It's a Sabbatical, Not Retirement

I live in Manhattan's premiere NORC (Naturally Occurring Retirement Community), but don't call it retirement. I'm busier than ever, just with different things. To deflect the endless questions, I'm sharing what I'm up to. This isn't about golf or leisure—it's about diving into new challenges and projects that excite me.

3. Meet Cooper, My Two-Year-Old Mascot

This adorable little fella is Cooper, age two. If your web app needs a mascot, apply within. He's a constant source of joy and a reminder that life beyond work has its own rewards. But he's also a distraction—in the best possible way.

4. Stack Overflow: Still My Baby, but Under New Management

I'm chairman of three companies, starting with Stack Overflow. You know the story—it's the Q&A platform for developers. With Prashanth at the helm, I can focus on guiding strategy without daily operations. The company continues to grow, and I'm proud to see it thrive under new leadership.

5. Glitch: A New Name, Same Mission

Fog Creek Software has been renamed Glitch, billed as "the friendly community for building the web." Under CEO Anil Dash, they've grown to millions of apps and raised significant funding. I believe every era needs a simplified programming environment for the majority of developers who just want to write code and run it—no fancy git branches or multi-step deployment. Glitch serves that quiet majority beautifully.

6. HASH: Open Source Simulation Platform

The third company, HASH, is still under radar, though they recently published more details. HASH is building an open source platform for simulations—modeling problems where you know each agent's behavior but not the collective outcome. Think city planning: you want to model traffic to justify a new bus line. You can simulate every driver's decision, testing millions of routes to find the best one. This is agent-based modeling at scale.

7. The Power of Agent-Based Modeling

Traditional formulas can't capture how individuals react to a new bus route. But with HASH, you simulate each "agent"—like in Cities: Skylines—and see emergent patterns. It's computationally intensive, but it works when closed-form math doesn't. This approach can revolutionize everything from traffic to epidemiology to economics. I'm excited to see where it leads.

So, that's my life now: chairman of three innovative companies, a sabbatical that's anything but lazy, and a dog who might just end up as your mascot. It's not retirement—it's a chance to explore what comes next, and to learn from the people I once led. And honestly, it's the best job I've ever had.