How the Daily Upside grew to over 1 million subscribers
Patrick Trousdale explains why he partnered with a traditional news brand and how he works with finance influencers.
In September 2019, Patrick Trousdale launched a finance newsletter with a simple but ambitious goal: help readers not just understand what happened in the markets, but why it matters over the long term. At the time, the newsletter ecosystem was still in its early innings, and the idea of building a large-scale media business around email alone was far from proven.
Six years later, that newsletter—The Daily Upside—has grown to over 1 million subscribers, built a 15-person editorial team, and carved out a lucrative niche serving senior business professionals. Its growth story offers a playbook for how independent media brands can scale without raising outside capital—by combining strategic partnerships, disciplined audience targeting, and a relentless focus on subscriber quality over raw reach.
As Trousdale puts it, the goal was never just to summarize the news: “Yes, we want our readers to understand what happened yesterday, but we also want them to understand why that matters in 3, 5, 10-year trends.”
In a recent interview, Trousdale walked through all his growth strategies, including how he convinced The Motley Fool to partner with him, how he works with finance influencers to drive signups, where he invests in paid acquisition, and how he collects first party data to measure the value of his audience.
Finding Product-Market Fit as a Solo Founder
Like many newsletter founders, Trousdale started alone. For the first several months, growth was slow and uncertain. By early 2020, the newsletter still hadn’t cracked 10,000 subscribers.
“I spent the first three months just trying to figure out what I was doing with the newsletter,” he says. “How the editorial process was going to work, how it was going to be different than what was already out there.”