Thoughts & Reflections
Writing
Essays on engineering leadership, startups, and building teams.
This post argues that building successful software for value-based care (VBC) requires a shift in mindset: create a Customer Relationship Management (CRM) tool, not just a better Electronic Health Record (EHR). VBC realigns healthcare incentives around long-term patient outcomes, succeeding through proactive, relationship-based care rather than transactional services. Technology's role is to support this relationship by helping care teams orchestrate interventions effectively. The most valuable tools are often simple and pragmatic, focusing on the unique, core needs of the care model and enabling proactive management of patient health.
Reflections on pausing the contextual recommendation tool, Kelp, concluding that its goal—getting people the right information at the right time—is nearly impossible for a third-party app to achieve. The core problem is technical: without deep, OS-level access to user data and behavioral signals, recommendations remain mediocre. True contextual help must be built into the operating system itself. The key business takeaway was the need to solve a highly specific, paying use case for a narrow audience before attempting a broad, cross-platform solution.
This reflection on leadership in a hyper-growth startup argues that self-management is the most crucial skill. Management in such a chaotic environment is inherently reactive and emotionally draining, not strategic and proactive. The key to effectiveness is to abandon "ruinous empathy"—the futile attempt to please everyone—and instead fiercely conserve personal energy for high-impact moments. This is achieved by accepting failure and tradeoffs as constant, communicating them transparently, and focusing on maximizing success in key areas rather than fighting every fire.
Brooklyn homeownership is not "worth it" as a financial investment. After accounting for renovation costs, high transaction fees, and the opportunity cost of not investing in the stock market, my profitable-on-paper sale was actually a financial loss. The true costs were the non-financial headaches: months of living in construction dust, battling city bureaucracy over permits, and fixing bank errors over property liens. I conclude that you buy a home not for the return, but for the control and satisfaction of making a space your own.
This post argues that as startups grow, the initial high-trust environment often collapses into chaos. The common leadership mistake is to push for more speed; the real solution is to slow down and rebuild trust through predictability. The author outlines a four-stage journey where a team matures by making and keeping progressively more abstract promises: evolving from committing to specific tasks (via ticketing systems), to achieving monthly goals, and ultimately, to delivering business impact measured by KPIs. This entire process is driven by retrospectives, which help a team understand its current level of trust and take the next step.
An engineer at a successful startup sold $x million in shares to diversify my wealth, only to discover afterward that they were just two months shy of qualifying for the QSBS tax exemption. This "hidden rule" would have eliminated their entire federal tax bill. The post serves as a cautionary tale about the immense financial cost of navigating the complex and often obscure tax laws surrounding startup equity without specialized knowledge.
Creating a successful engineering ladder isn't about perfect documentation—it's about building trust and psychological safety. The best ladders are actively used by teams and trusted across the organization because they're built on a foundation of "trust but verify" principles and open communication. Treat your ladder like a business relationship with SLAs, acknowledge potential failure modes, and remember that its success hinges on whether both engineers and management share a common understanding of its terms.
Finding smart, motivated people who work well together is virtually impossible. If Artsy has a secret sauce, it is how it hires. All else falls from the assumption that they have hired the best people who want to work together to achieve Artsy’s mission.
We all have stories, as engineers, of fixing some crazy thing at the last minute right before the demo goes up. We have all encountered situations where we needed to fix something that was our fault and we needed to fix it now.
