Building a Financial Advisory Newsletter: Lessons From The Daily Upside’s FA Upside Launch
By: Haniya Rae
When Patrick Trousdale, CEO of The Daily Upside, started his flagship newsletter in December 2019, and through most of the early part of the decade, money was easy.
“In late 2022, I sold out our flagship newsletter with 20% of my time,” says Trousdale. “I had zero talent doing it.” But, within the last year and a half, nearly 80 to 90% of those sponsors pulled back, forcing a reckoning about The Daily Upside’s offerings and its audience. He estimates The Daily Upside flagship will reach about $3 million in revenue in 2024, growing slightly from $2.3 million in 2022.
Trousdale knew he needed to get serious about the data and audience lifecycle. The Daily Upside’s other products, Power Corridor, a newsletter focused on political and financial figures who shape the U.S. economy, and Patent Drop, a newsletter about tech advancements for tech builders and investors, had unique value propositions for the flagship audience, but the commercial and audience strategy wasn’t there. “Had the market not changed, we wouldn’t have needed to learn these lessons. You really need a fully buttoned plan.”
Enter FA Upside, a new product launched in late June 2024 meant for financial advisors. Although there are multiple publications that serve the financial advisor community, there was nearly no competition from a newsletter-first approach.
But despite that unique opportunity offering less competition, there remained a primary challenge: potential sponsors aren’t bullish on new things. “A lot of the companies and financial services are conservative by nature,” says Trousdale. It applies to investment strategies but also to marketing.” That means for new publishers in the financial space — or any space conservative with its money — you need names that potential sponsors know and feel comfortable with.
Building the right team
The biggest part of Trousdale’s strategy for FA Upside was finding talent that the industry knew well to compete and grow a newsletter. By his measure, it’s easier to grow the audience from an editorial perspective than to get financial space marketers to try something new.
To address the first part of that dilemma, The Daily Upside hired Sean Allocca, the former editor-in-chief of ETF.com, as a wedge that could speak to the audience well and be a name that drives sales.
“Everyone knows each other,” says Trousdale. “All the sellers know each other. So when hiring Sean, we feel like we have a star. From a business perspective, all the managers and marketers know Sean. It’s a huge asset when you hire a star journalist.”
The second piece of the dilemma was hiring the right sales talent. Allocca may be a big enough name, but without the right sellers, it’s hard to reach the right buyers. For this, Trousdale improved The Daily Upside’s outbound recruiting strategy, locating and messaging industry-specific salespeople who could bring the right relationships to sell FA Upside. “The right person may or may not apply for your job,” says Trousdale. “You need an outbound strategy. We think LinkedIn is an awesome resource for that.”
Getting Serious About Data
One of the points AMO made about Daily Upside roughly a year ago was the need for The Daily Upside to get serious about newsletter data, specifically digging into the audience and capturing a ton of first-party data. It’s a path that Trousdale ended up committing to instead of launching other types of media products, like short-form videos, and spreading The Daily Upside thin.
“I’d say three years ago, newsletter subscribers were created equally,” Trousdale elaborates on his thinking. “Now we collect 20 or more different data points about who is reading.” The new collection strategy is helping to guide editorial decisions because of the clarity of the audience. Trousdale is also hoping that eventually, they can concentrate on very specific stories and content based on who you are. He’s also using the data to recommend readers to other newsletters, like Patent Drop, depending on where the reader works, such as a hedge fund.
The new funneling has helped grow FA Upside. The new newsletter launched June 21st with 4,300 subscribers gleaned from the flagship Daily Upside newsletter; in two-and-a-half months this number is now 27,000. This is three-quarters of the financial advisors (some 40,000) who read the flagship newsletter, but less than a tenth of the potential audience of about 300,000 financial advisors working in the U.S.
Room for FA Upside to Grow
FA Upside’s growth is somewhat capped out of the gate (you may not reach millions of subscribers when the audience peaks at only a few hundred thousand), but there’s still a decent number that can be reached with the right marketing and PR campaigns. Trousdale stresses that having star talent is key to getting the word out. A recent example: Josh Brown, a big name within the advisor space and host of The Compound and Friends podcast, had Allocca on to talk about wealth management, further boosting FA Upside to the audience.
From what Trousdale can gather, about 40% of the growth (roughly 10,000 of the 27,000 FA Upside subscribers) has been from the flagship, with 20% from paid acquisition efforts with Google search. He’s also seen success on LinkedIn, Meta, and even Quora for niche questions that advisors ask within the platform.
Since FA Upside is only a few months old, it needs additional fine-tuning. Since its launch, it has made Trousdale reconsider his other products and how he wants to redo them with the knowledge he has now from the FA Upside while still learning about the new product itself. “I definitely spend all my time thinking about FA Upside since deciding we were going to launch. It hasn’t been that long, so we’re going to learn a lot more.”
For all this effort, Trousdale admits that FA Upside isn’t profitable yet. So far, they’ve secured a few partners and are working with others for yearly sponsorships. “But I can confidently say in Q1 2025, we’ll have had the biggest pipeline we’ve ever had for a product.”
