How investment newsletter The Daily Upside reached 300,000 subscribers

Founder Patrick Trousdale explained his growth and monetization strategies.

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Patrick Trousdale had a fairly unique view of media businesses before he decided to launch his own: he was the guy you called when you wanted to sell one. 

As a vice president at Guggenheim Partners, a New York investment and advisory firm, he counseled media clients on mergers and acquisitions. While he enjoyed the challenge of the work, he eventually grew frustrated that he only got to collaborate with media businesses from a distance. “At the end of the day, I wanted to focus more on the other side of the table — working on actually growing a business from the ground up,” he told me. “It was something that I wanted to do pretty much for the entire duration of my career in investment banking. It took about a decade to build up the courage, but I finally got there.”

That’s how Trousdale ended up quitting his job and launching The Daily Upside, a finance-focused newsletter. Though the publication struggled to find its footing at first, Trousdale eventually found a format that worked, and over the next two and a half years he grew it from an audience of friends and family to over 300,000 subscribers.

How? Well, he experimented with several growth channels, but his biggest break came when he established a partnership with a much larger and more established media outlet. That move supercharged his growth and opened the door to sponsorship opportunities. In a recent interview, he walked me through his journey from advising media companies to operating one himself.

Let’s jump into my findings…

Finding his voice

Like many aspiring newsletter entrepreneurs, Trousdale drew a lot of his inspiration from business publications like Morning Brew and The Hustle. When planning the launch of The Daily Upside, he envisioned a more niched-down version of those newsletters. “I personally wanted to build a product for investors specifically,” he said. “[Morning Brew and The Hustle] do a great job with their product, but my idea was to try to go a layer deeper on the stories we cover and draw out insights that, in theory, could help investors frame their point of view about the world.”