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.
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.
The perfect partnership
In early 2021, Trousdale decided that he needed to find a partner, preferably one with an already-existing audience. He started reaching out to executives at finance publications to see if any were interested. “I talked to three or four major media companies and had varying degrees of interest,” he said. “Some liked the product and wanted to bring The Daily Upside in-house, and have me basically become a writer full-time at an established publication.” But he wasn’t interested in becoming someone’s employee; he wanted to steer the business and then benefit from its success.
Luckily, he struck gold when he cold emailed John Keeling, a SVP of business development at The Motley Fool. Founded in 1993, The Motley Fool is a well-established financial news publisher, and Keeling heads up its investment arm, Motley Fool Ventures. Trousdale’s introductory email talked about his background in finance and gave an overview of his progress thus far with The Daily Upside. “I'm sure he subscribed and read it for a couple days, and then reached back out. We started a conversation about the newsletter and where I saw it going, and we ended up meeting right before the pandemic in New York and started discussing what a partnership could look like.”
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By that point, both The Hustle and Morning Brew had sold for millions of dollars, and Keeling no doubt saw an opportunity to invest early in a company that could end up having a similar exit. But first he needed to see if there really was a mass-market audience for The Daily Upside — that it could become something other than a niche product. So the two came to an agreement whereby The Motley Fool would expose the newsletter to a subset of its audience and then assess the impact of that exposure.
Here’s how it worked: The Motley Fool segmented out a portion of its marketing list and sent a dedicated email encouraging readers to sign up for The Daily Upside. It repeated this for about five months. “From there we evaluated open rates, click through rates, and just the overall feedback on the newsletter from folks in their organization,” said Trousdale. It was fortunate timing, as the pandemic had sent the economy into a tailspin, which then triggered a surge in interest in how the markets were reacting to breaking news events that ranged from government stimulus to federal reserve policy to virus outbreaks. “The engagement was off the charts from day one. We saw 40% to 50% unique open rates.” Over that five-month trial period, The Daily Upside grew from 3,000 subscribers to 40,000.
By all measures, the partnership had been a success, and Keeling had seen enough to convince his colleagues that there was clear synergy between The Motley Fool and Daily Upside. About six months after the partnership began, the former made a “modest” investment in the latter. “We now have a kind of economic relationship where we're both incentivized to see the newsletter do well,” said Trousdale.
Growth on steroids
The Motley Fool partnership generated crucial momentum for The Daily Upside, but Trousdale knew it would only take him so far before he had to find new marketing channels. He started by negotiating recommendation swaps with other newsletters, and when that proved highly effective he allocated a budget for advertising in newsletters. He also invested heavily in social media advertising — not just through the platforms themselves, but also by paying creators directly. “We're kind of a scrappy media upstart, and that resonates with a lot of creators on TikTok and Instagram. So when we reach out to creators, it's not as some big stodgy brand, it's kind of like we’re fellow creators.”
Some of this creator outreach resulted in collaborations. “Sometimes we'll almost license out some of our content or story ideas. A TikTok creator will make a video about it as if they came up with the content, but then give us a shout out at the end of the video, because it was our legwork that they used to make the script.”
When I was conducting research for this article, I came across a video created by TikTok user irisayalaa, who has around 96,000 followers. Here’s her script:
I’m going to show you where you can get the latest financial news for free. You need to go to The Daily Upside. It’s a completely free financial newsletter. You’ll get the latest news on what’s happening in the market right to your email. And it gets better, because these guys are actually legit. I want news from people who know what they’re talking about. The founder was an investment banking VP, and now he’s helping people like you and I stay more informed on what’s going on in the markets, for free. So you have no excuse not to be informed. So go sign up . It’s in my beacon’s page.
Trousdale also employed other newsletter growth hacks, like introducing a referral program that would send readers rewards if they convinced their friends and colleagues to sign up. “To be honest, it hasn't represented a massive portion of our growth. On balance, our readers are slightly older than [readers for Morning Brew and The Hustle,] so I don't think there's that same inherent level of excitement around sharing a newsletter just so they can get a free t-shirt.”
Whenever I profile a curatorial publication like The Daily Upside, I always wonder if it has ambitions to go beyond mere curation. Could the newsletter serve as a foundation to start hiring out seasoned journalists who conduct actual original reporting?
Trousdale didn’t seem too interested in going that route. “I think our differentiation will likely not be in breaking news. I think where we'll thrive is by providing insights and color and analysis on the breaking news stories that matter. We're never going to be first to get a story out, but I think we need to build a brand that people can trust after the dust is settled and they need a comprehensive analysis of what happened.”
That’s not to say that The Daily Upside has remained a one-man operation. It’s hired at least one full-time writer and also works with several contributing writers. “We have a growth marketing manager and an ad operations specialist who helps coordinate relationships with our sponsors.”
Trousdale held off on monetization until 2021, but he immediately saw strong demand once he opened up sponsorships. When I spoke to him in October, he had already sold out all of his advertising slots for the rest of the year. “We're selling roughly 75% of our ads ourselves, and we work with a number of agents and talented professionals throughout the space who have spooled up their own operations to sell the other chunk of ads.” Most of the brands they work with operate in the finance space.
So what’s next for The Daily Upside? Other newsletters like it either expanded into new niches or launched into completely different mediums like podcasts or video. Did Trousdale already have his eyes on new frontiers? “I think we're laser focused on our daily newsletter at the moment,” he said. “I think it's very easy to look at different avenues we could pursue — from podcasts to paid products to building out programmatic advertising and trying to scale the web presence — but I think the strength of our business is just being uber-focused on one product. We want to be a must-read day in and day out, and what drives a lot of success for newsletter brands is not losing focus. So I think that's where our head is at for at least the next 12 months.”
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