Guiding New Leaders and Building Platforms: Life After the CEO Role

From CEO to Chairman: A Transition of Growth

After stepping down as CEO of Stack Overflow, Prashanth Chandrasekar has taken the helm, and I've embraced a new chapter. I still join customer calls and maintain a weekly meeting with Prashanth, but the reduction in day-to-day responsibilities has opened up my schedule significantly. Watching him restructure the company—for the better—has been a revelation. It's genuinely rewarding to realize that the best outcome for me is that my successor outperforms my own tenure. This period, which I consider a sabbatical rather than retirement, has proven to be remarkably busy and fulfilling.

I live in Manhattan's premier Naturally Occurring Retirement Community (NORC), but don't let the acronym fool you—I'm far from idle. To address the many inquiries about my current activities, here's an update on what fills my days.

Stack Overflow: Handing Over the Reins

As chairman of Stack Overflow, I remain deeply involved in an advisory capacity. The company continues to be the leading Q&A platform for developers, and under Prashanth's leadership, it's evolving in exciting directions. My role now focuses on strategic guidance and supporting the new CEO. This transition has taught me just how much I didn't know about running medium-sized companies—and that's a humbling and valuable lesson.

Glitch (Formerly Fog Creek Software): A Platform for Everyday Developers

Fog Creek Software has transformed into Glitch, described as "the friendly community for building the web." Under CEO Anil Dash, Glitch has grown to host millions of apps and raised significant funding to accelerate that growth. My belief is that every era needs a simplified programming environment for the quiet majority of developers—those who don't require complex features like git branches or multi-step deployment. They just want to write code and see it run. Glitch serves precisely that audience, lowering the barrier to web development.

HASH: Simulating Complex Systems

The third company I chair is HASH, which remains somewhat under the radar. Recently, they published substantial content on their website, so here's a preview. HASH is building an open source platform for simulations. It excels at modeling problems where you understand individual agent behaviors but can’t anticipate collective outcomes.

Example: Traffic Modeling for a New Bus Line

Consider a city planner who wants to justify a new bus line. Traditional methods might assume each bus removes 50 cars from the road, but that simplification fails because it ignores commuter decision-making. Will people switch to the bus if it saves time and money? HASH enables agent-based simulation, akin to games like Cities: Skylines, where each agent’s behavior is modeled individually. The planner can then test thousands or millions of potential bus routes and identify which ones actually reduce traffic.

This type of modeling is computationally intensive, but it's powerful when closed-form formulas are unavailable—for traffic, epidemiology, or any system with interacting agents. HASH makes this accessible.

A Busy Sabbatical

Between chairing these three companies and mentoring their CEOs, my days are full. I'm also enjoying the company of my dog Cooper (age two—if your web app needs a mascot, let me know). This period feels more like a second act than an ending. I'm learning, building, and watching others succeed—and that's a pretty great way to spend a sabbatical.