In this episode of Personal IPO, Nathan sits down with Tim Huelskamp, co-founder and CEO of 1440, the daily newsletter read by over 4 million people. Tim shares how he left private equity to build a $20M+ media business from scratch — breaking down the math, mindset, and management behind 1440’s success. You’ll learn how he mastered unit economics, built a lean and profitable team, and created one of the most trusted newsletters in the world.

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Tim Huelskamp

• LinkedIn

Nathan May⁠

• LinkedIn⁠ ⁠
• X/Twitter⁠

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Timestamps

00:00 Introducing Tim Huelskamp

03:08 What Tim learnt working in private equity

11:37 Why start a newsletter?

20:39 The unit economics of a newsletter business

28:35 The history and evolution of 1440

35:10 When you should raise equity

38:30 How to get your first $10k/mo

44:50 The difficulties of running a media business

51:43 The importance of building a strong culture

59:42 1440's future plans to scale