Tyler Denk is the Co-founder and CEO of beehiiv, the newsletter platform built for growth. We go inside beehiiv’s early days, including joining MorningBrew as the second employee, lessons scaling to 3.5 million subscribers, the $75 million sale to Business Insider, and why I didn’t invest in beehiiv despite being an early customer. Tyler takes us inside the playbook that grew to $1.5m in monthly revenue in less than three years, including how they first positioned the product in a crowded market, how beehiiv ships so fast, when a co-founder passing away less than one year into building the business, and the day GoDaddy took the entire beehiiv platform offline for 8 hours. Timestamps (00:00) Intro (01:36) Why Turner didn’t invest in beehiiv (twice) (03:04) Joining MorningBrew as the first employee (15:28) Why newsletters are so powerful (19:40) Scaling MorningBrew to 3.5 million subscribers and exiting to Business Insider (23:14) Difference between startups and big companies (26:26) Why beehiiv has two days of no meetings (27:53) The initial insight to start beehiiv (35:39) Building a programmatic newsletter ad marketplace (39:52) Dissecting beehiiv’s nearly $20m rev run rate business model (45:21) Inside beehiiv’s first funding round (46:58) Where Turner’s reference check went wrong (50:45) Litquidity and beehiiv’s initial product positioning (52:59) How beehiiv builds in public (57:41) Banning meetings two days per week (01:00:13) Why the best remote teams always beat in-person (01:06:19) The impact of a co-founder dying one year into the business (01:11:50) Raising a Series A despite operating at breakeven (01:16:14) Why Tyler writes public investor updates (01:21:04) Moving fast, and “why perfect kills all momentum” (01:26:03) When GoDaddy took beehiiv down for 8 hours (01:29:57) Why Tyler writes a newsletter (01:32:21) His Big Desk Energy Spotify playlist (01:36:08) Why you never regret firing bad hires (01:39:53) Looking up to Elon and Brian Chesky (01:41:34) Monk mode in Columbia Referenced The Power of Investor Updates: https://mail.bigdeskenergy.com/p/power-investor-updates beehiiv’s old investor updates: https://mail.bigdeskenergy.com/c/beehiiv-investor-journey The BDE Spotify Playlist: https://open.spotify.com/playlist/5s8443tfYUq3LLARJwGeYP Where to find Tyler Twitter: https://twitter.com/denk_tweets LinkedIn: https://www.linkedin.com/in/tyler-denk Newsletter: https://mail.bigdeskenergy.com Where to find Turner Twitter: https://twitter.com/TurnerNovak LinkedIn: https://www.linkedin.com/in/turnernovak Newsletter: https://www.thespl.it