Joel Spolsky's Post-CEO Life: A Sabbatical of Chairmanships and New Ventures

Joel Spolsky, former CEO of Stack Overflow, has entered a phase he calls a sabbatical rather than retirement. He now chairs three companies: Stack Overflow, Glitch (formerly Fog Creek Software), and HASH. He also adopted a dog named Cooper. Here are answers to common questions about his current activities.

What is Joel Spolsky doing after stepping down as Stack Overflow CEO?

Joel is spending his time as chairman of three companies. He still participates in customer calls and has a weekly meeting with the new CEO, Prashanth Chandrasekar, but has significantly freed up his schedule. He now enjoys observing how Prashanth reorganizes the company, admitting he didn't realize how little he knew about running medium-sized businesses. Joel considers this a sabbatical rather than retirement, emphasizing that he's extremely busy with his chairman roles and exploring new interests. He also recently got a two-year-old dog named Cooper, who serves as an unofficial mascot.

Why does Joel call this a sabbatical instead of retirement?

Joel clarifies that despite living in Manhattan's Naturally Occurring Retirement Community (NORC), he doesn't see himself as retired. He finds himself genuinely busy with his duties as chairman of Stack Overflow, Glitch, and HASH. He also enjoys the freedom to explore new projects and reflect on his past tenure without the day-to-day pressure of being a CEO. This period allows him to learn from his successors and appreciate the evolution of the companies he founded. He describes it as a time of discovery and growth, far from the sedentary image of retirement.

How is Stack Overflow performing under new CEO Prashanth Chandrasekar?

Joel reports that Stack Overflow is thriving under Prashanth Chandrasekar's leadership. He admits that watching Prashanth 'rearrange everything—for the better' has been eye-opening. Joel enjoys realizing that the best possible outcome for him is if Prashanth proves to have been a better CEO by running the company more effectively. This perspective allows Joel to take satisfaction in the company's progress without ego. He still maintains a light advisory role, joining customer calls and weekly meetings, but largely steps back to let the new leadership shine.

What is Glitch and who uses it?

Glitch, formerly Fog Creek Software, is now rebranded as the friendly community for building the web. Under CEO Anil Dash, it has grown to millions of apps and secured significant funding. Joel believes that every era needs a simplified programming environment for developers who don't require complex features like git branches or multistep deployments. Glitch serves this quiet majority—developers who just want to write code and see it run. It's a community-driven platform that lowers the barrier to web development, making it accessible for beginners and efficient for experienced coders looking to quickly prototype ideas.

What is HASH and how does its simulation platform work?

HASH is building an open platform for agent-based simulations. It allows users to model situations where you know how individual agents behave but not the collective outcome. For example, a city planner can simulate traffic by modeling each commuter's decision to take a bus based on time and cost savings. HASH runs millions of potential bus routes to find which ones actually reduce congestion. This approach works even without a closed-form formula, as it simulates the behavior of every agent in the model, akin to games like Cities: Skylines. The platform is computationally intensive but highly effective for complex problems where traditional equations fall short.

Why is agent-based modeling useful for real-world problems?

Agent-based modeling, as implemented by HASH, excels in scenarios with unpredictable interactions. Unlike top-down equations, it simulates autonomous agents (people, vehicles, etc.) and their decisions based on rules. This captures emergent behavior—like traffic jams or financial market crashes—that can't be predicted by simple averages. For instance, a new bus line's impact on traffic depends on thousands of individual commute choices. By running simulations, planners can test numerous scenarios and find optimal solutions. HASH's open nature encourages collaboration, making this powerful tool accessible for urban planning, epidemiology, economics, and more. It represents a shift toward data-driven, bottom-up analysis.