In this episode, I sat down with Henry Winslow, the founder of Tricycle Day, to break down how he grew a twice-weekly newsletter to 65,000 subscribers in about two years—without pretending it was some magic growth hack. Henry’s early strategy was “total brute force”: write a first issue in private, get a handful of friends to subscribe, ride the early network effects, then manually invite people until he hit 1,000 subs. From there, he started running paid ads as his primary acquisition channel, even before the business was fully monetized—because he had savings, believed in the mission, and wanted to reach critical mass faster. We also got into format decisions (a Wednesday roundup vs. a Sunday Q&A interview), what qualitative KPIs he actually cares about (replies, polls, community growth, and real-world brand recognition), and why “mission” is the anchor that answers most strategic questions. We also talked about the less glamorous parts: revenue sustainability, diversifying beyond sponsorships, and even deliverability/censorship risk—his email infrastructure provider drew a hard line when he promoted courses, which forced him to adapt. The big takeaway: if you want to build a durable newsletter business, you need distribution discipline, a clear thesis, and a monetization plan that isn’t dependent on one fragile channel.