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The Business of Content

Apr 6, 2022

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When Patrick Trousdale launched his newsletter The Daily Upside in 2019, he didn’t have much of a personal brand to build from. In fact, even today, his personal Twitter account has fewer than 300 followers.


What he did have was several years of experience in finance and the willingness to grind out the newsletter each day, even when it didn’t have much of a following. That kind of persistence netted him his first few hundred followers, and it also helped him get his foot in the door so he could pitch The Motley Fool, a popular finance website, on a content partnership.


That partnership paid off in a big way, and The Daily Upside quickly grew by tens of thousands of signups. Today, the newsletter has over 300,000 subscribers and has sold out its ad inventory for months in advance.


In our interview, Patrick walked me through his initial launch strategy, his business model, and how he convinced editors at The Motley Fool to take a chance on a partnership with an unknown entity.