From a college kid running the SportsCenter teleprompter to the newsletter that reaches over a million inboxes every morning, Kendall Baker has lived the entire boom-bust-boom cycle of email media — and he's not holding back.

He breaks down why he sent 50 different newsletter formats in his first three months, how he negotiated an acquisition without ever naming a price, and what it actually took to convince 100,000 subscribers to follow him from one company to the next. Along the way: the "secret weapon" RSS feed that powers his daily grind, why AI can aggregate news but can't replicate taste, and an honest look at why newsletter advertising is still years behind podcasts. If you've ever wondered what it takes to build (and keep) an audience that opens your work every single day, this one's a masterclass.

⏱️ Timestamps

00:00 — Intro

00:45 — The roundabout path into sports media

01:47 — Bleacher Report, ESPN, and finding his voice

03:31 — Trading TV glamour for newsletters

03:45 — The Skimm and the lightbulb moment

06:24 — Advice for starting a newsletter from scratch

08:59 — Newsletters vs. social media: the data problem

10:55 — Selling Sports Internet to Axios

13:56 — The power of a daily habit

16:22 — Kendall's process and his RSS "secret weapon"

19:45 — Standing out from AI aggregation

22:28 — Why newsletters are booming again

25:56 — What Yahoo actually is today

29:23 — Giving away ideas for free on Twitter

39:45 — Sharing competitors' work and building trust

42:11 — Why newsletter advertising is still so immature

46:50 — The newsletters Kendall actually reads

48:54 — Outro