The Contrarian Approach to a $100M Newsletter

This week on Letterland LIVE, we welcome 1440 founder and CEO Tim Huelskamp. Tim built 1440 into one of the biggest daily newsletters in the world. We'll get into the playbook behind scaling a daily news digest to millions of readers, the economics of the aggregation model, and where he sees opportunity in the newsletter space heading into the second half of 2026. We'll also get into: :iphone: A new player enters the newsletter arena :sleeping: Inbox fatigue and the new newsletter survival rules :office: When does your newsletter become a "media company"? :mortar_board: The newsletter course gold rush hits mainstream :closed_lock_with_key: Why media authentication genuinely sucks :poultry_leg: Food giveaways as a newsletter growth engine ... and everything else you need to know about the newsletter world. Subscribe to never miss a Letterland LIVE:    / @letterlandlive   Join the Letterland Brief daily newsletter to keep on top of all the headlines and thought leadership: letterlandlive.com Follow the 'land on socials: LinkedIn:   / letterlandlive   X/Twitter: https://x.com/LetterlandLIVE About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.