A CEO's Sabbatical: Steering Three Companies Beyond the Corner Office

Introduction

When a founder steps aside from the day-to-day leadership of their company, the natural question is: what next? For Joel Spolsky, co-founder of Stack Overflow and Fog Creek Software, the answer is a mix of hands-on board work, nurturing new ventures, and enjoying a well-earned sabbatical. Since passing the CEO baton at Stack Overflow to Prashanth Chandrasekar, Spolsky has discovered that stepping back doesn't mean stepping away—it means seeing his companies thrive under fresh leadership while he explores new passions.

A New Era at Stack Overflow

Prashanth Chandrasekar took the helm as CEO of Stack Overflow a few months ago, and Spolsky has been delighted to watch the company evolve. He still joins customer calls and maintains a weekly meeting with Chandrasekar, but the reduced operational load has opened up significant time. Rather than hovering, Spolsky finds deep satisfaction in observing how little he knew about running medium-sized companies, as Chandrasekar reworks processes for the better. “The best possible outcome for me is if he proves what a bad CEO I was by doing a much better job,” Spolsky reflects. It's a sentiment of genuine support, seeing the company accelerate under new direction.

Chairman of Three: Glitch and HASH

Beyond Stack Overflow, Spolsky serves as chairman for Glitch and HASH—two companies tackling very different corners of the software world. Each is carving out its own niche, and Spolsky stays closely involved from the board level.

Glitch: The Friendly Community for Building the Web

Formerly known as Fog Creek Software, Glitch has been rebranded as “the friendly community for building the web.” Under CEO Anil Dash, the platform has grown to host millions of apps, fueled by a recent funding round. Glitch aims to serve the “quiet majority” of developers—those who don't need advanced features like git branches or multi-step deployments. Instead, they simply want to write code and see it run instantly. Spolsky believes that every computing era needs a simplified environment for this audience, and Glitch is positioning itself as that go-to sandbox for creative, low-friction development.

HASH: Simulating Complex Systems

HASH remains somewhat under the radar, but it recently published detailed information on its website, giving a clearer picture of its mission. HASH is building an open-source platform for agent-based simulations—a tool to model problems where you know how individual agents behave but can't easily predict the emergent outcome. For example, consider city planners trying to justify a new bus line. Traditional approaches might assume each bus removes 50 cars, but that overlooks the decision process of commuters: they'll only take the bus if it saves them time and money compared to driving. HASH allows planners to simulate every agent's behavior, much like the game Cities: Skylines does, and then test millions of possible bus routes to see which actually reduce traffic. This kind of modeling is computationally intensive, but it works where closed-form formulas fail, making it valuable for fields from urban planning to epidemiology.

Life After the CEO Desk

Spolsky lives in Manhattan's premier NORC (Naturally Occurring Retirement Community), but he's quick to clarify that this period is a sabbatical, not retirement. In fact, he's remarkably busy. To defuse the constant queries about his current activities, he offers a snapshot of his days. Among the personal highlights is Cooper, a two-year-old dog who might just become a web app mascot—if any startup is looking for an adorable ambassador.

From advising Stack Overflow's leadership to guiding the growth of Glitch and HASH, Spolsky's sabbatical is a masterclass in constructive disengagement. He's not just stepping away; he's stepping into a new role as a seasoned mentor, letting the next generation of leaders prove their mettle while he explores the boundaries of simulation and community-driven development.