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.”
It was harder to execute on this vision than he imagined. Early versions of The Daily Upside would pick a single company and examine its strengths and weaknesses — the idea being that a reader could leverage the information when deciding whether to invest in the company. The format didn’t really catch on. “In the first two months, I quickly realized that, while I enjoy doing this, if someone's going to open up this newsletter every day, there has to be some connection to current events or there's going to be some level of fatigue.”
So a few months in, Trousdale pivoted. While the finance focus remained, he started pegging the newsletter to current events. “That's really the product that still exists today,” he said.
To get a sense of what he was talking about, I signed up for The Daily Upside. Each edition starts with a brief intro paragraph that touches upon a big story in the news. It then launches into around three sections, each a few hundred words long. Here’s a sampling:
An intro paragraph about a billionaire investor who sold all of his Netflix shares
A section about how Goldman Sachs is restructuring its executive pay
A section about an aviation startup raising $375 million
A sponsored section about what to do with capital gains of $50k or more
A section about how rising interest rates are affecting junk loans
A short roundup of additional news links
An intro paragraph about a bevy of billionaires launching their own music festival
A section about Netflix losing subscribers
A section on Blackstone investing $13 billion in student housing
A sponsored section about a marketplace for rare sports collectibles
A section about a new Chipotle-run venture fund
A small roundup of news links
This change in strategy seemed to click with Trousdale’s audience, and he saw a noticeable uptick in both open rates and new subscribers. The Daily Upside benefited from some early word-of-mouth in which readers would forward it to their friends and colleagues, and he also experimented with some paid acquisition by advertising on social media and other newsletters.
After about a year, the newsletter had around 3,000 subscribers, which is pretty impressive when you consider that Trousdale had no pre-existing personal brand when he launched it. But remember, he was trying to emulate publishers like Morning Brew and The Hustle, both of which didn’t start generating substantial advertising revenue until they reached massive scale. If he wanted to attract serious advertisers — the kind that would plop down five figures for sponsorships — he needed to grow the newsletter’s audience by a factor of at least 100, which meant that word-of-mouth marketing alone wasn’t going to cut it.
Paywall incoming…
The rest of this case study is behind a paywall, but if you aren’t ready to subscribe, you can also download it as an ebook over here:
THE NEXT MEDIA MOGULS: 97 of the most successful media entrepreneurs reveal their secrets
Ok, back to the article…