Reflecting on my failure to build a billion-dollar company

Reflecting on my failure to build a billion-dollar company
16 minutes by Sahil Lavingia

Gumroad started as a weekend project that quickly attracted millions in venture funding, but growth stalled and led to laying off 75% of the team. Rather than shut down, the founder chose to keep the business running for the creators who depended on it. Over time, the company became lean and profitable. Sahil now measures success by the value created for others, not by chasing a billion-dollar valuation.

Learn how leading teams are building and scaling AI agents in production
sponsored by LangChain

Agents can write and run code seconds before execution, often without human review.  Local environments and standard containers weren’t designed for that level of autonomy. LangChain’s latest guide explains what safe agent execution requires, including isolation, permissions, observability, fast provisioning, and persistent state. Read the guide to learn when a managed sandbox makes sense, what capabilities to look for, and how to give agents the tools they need without handing them your infrastructure.

Two-way doors sometimes lock behind you
5 minutes by Jeff

Technical decisions that seem reversible can become difficult to undo over time. As teams build more systems, processes, and dependencies around a technology, the cost of replacing it increases. Jeff explains that optionality must be actively maintained, not simply assumed. He suggests documenting assumptions, estimating migration costs, testing exit plans, and accepting when some decisions are worth making permanent.

Finding calm in life and work
8 minutes by Yew Jin Lim

Anxiety measurably hurts performance, dropping the average anxious person to the bottom third of their peers. Modern work culture makes this worse by rewarding busyness over real output, pushing people toward low value activity that triggers constant dopamine seeking and low grade stress. Yew suggests simple habits that help: set clear work boundaries, move your body, spend time with people, and focus on work that actually matters to you. Calm is not a reward for finishing. It is available now.

A practical guide to fast onboarding
15 minutes by Steve Huynh

Getting up to speed in a new role feels overwhelming because people treat all information the same. A better approach is to sort incoming knowledge into three buckets: facts, processes, and concepts. Facts you either memorize or know where to find. Processes are best learned by doing. Concepts, the ideas behind how things connect, are the most powerful because they transfer across roles and domains, letting you contribute faster wherever you go.

How to measure engineering
16 minutes by Jade Rubick

ValueSum is a metric for engineering teams that tracks value delivered over time. You list everything shipped, score each item by business value, and sum it up. Higher scores mean faster delivery of more valuable work. It works across product, engineering, and design, can be applied retroactively, and helps teams learn by rescoring features months later to see how predictions compared to reality.

And the most popular article from the last issue was:

• Framework for managers starting a new role