How the Daily Upside Soared to over 700K Subscribers In Less Than 3 Years

Simone: Hi everyone. I'm here with Patrick Trousdale from The Daily Upside, and he's here to tell us about his journey. He's here to tell us about the product and so we're going to jump right into it. Patrick, hi. Welcome. Can you tell us a little bit about your role at The Daily Upside?

Patrick: Sure. So I am the founder and the CEO of The Daily Upside. I launched the company in fall 2019. And in the early days, perhaps like a lot of newsletter operators, I was the writer, the accountant, the bookkeeper, the marketing department.

Simone: That's impressive.

Patrick: So yeah, it was a bootstrapped venture that I started uptown here in my studio apartment on the Upper East Side. And my role has evolved over the last two years, but in the early days, I was writing the newsletter, doing everything I could, call it in the evening hours, to grow the newsletter, and setting the stage for what would come.

Simone: Multiple hats for success. Wow. Can you provide us a little bit more in depth on the product?

Patrick: Definitely. So my background before launching The Daily Upside was working on Wall Street as an investment banker, mostly doing M& A. And the vision for the product, really from the early days was to create a product that filled the vacuum between what Wall Street was consuming and what call it retail, sophisticated retail was consuming. In my mind, there's been kind of a large vacuum between not only the substance and content, but also just the voice. There are kind of precious few brands who can talk about, talk about wheaty and complex issues like interest rates, unwinding a pandemic stimulus at the Fed, while also keeping people engaged in a way that's perhaps not so dry. So I think part of our success has been, there's been a lot of appetite for a brand that can kind of keep professionals engaged, make them feel like they're reading from an insider's perspective, but also kind of keep it fun. Keep it interesting.

Simone: Yeah. Following along on that, I think it's really good you're informing the readers of what The Daily Upside it is all about. Can you tell us a little bit more about your audience and the content that you bring to that audience and how does that play into your distribution model?

Patrick: Yeah, definitely. So I guess for a little bit of context, my background is I worked in investment banking for my first 10 years of my career. So I'd say that kind of basically informed the product that I wanted to read and then thus built myself. So I'd say we straddle the line between basically Wall Street coverage for kind of financial professionals, whether it's investment bankers, traders, wealth managers, other types of asset managers, and the retail public. So we're not writing in a way that's in, call it the most high- falutin way. We're trying to break down concepts in a way that really anyone can understand, but is still kind of smart and insightful enough for the professional crowd. So I'd say roughly 30% of our audience are financial professionals who are probably working within a couple square blocks. And then around 70% retail investors or business people who are just generally looking to become smarter.

Simone: Got it. What's been your acquisition strategy?

Patrick: I think we've done a little bit of everything and a lot of a couple things that I've worked well. I think probably over the last two years some of the most successful strategies have been partnering with real people who also have audience, whether it's another newsletter audience, whether it's a large creator on YouTube, whether it's a creator on TikTok. Basically reaching out to them and forming a real relationship such that if we kind of co- market with them or have them market The Daily Upside, they have a bonafide view of The Daily Upside as a real product that they enjoy. And then they basically will recommend The Daily Upside to their audience. And we found that creator oriented partnership to be really successful across channels.

Simone: Can you provide some insights into how Campaign Monitor is helping you do that?

Patrick: To us, the biggest, I'd say the two biggest levers of the business on top of content are being just very analytical about how we're growing. So as we partner with creators, as we partner with other platforms to grow our list, we are just very analytical about the economics of how much can we afford to pay to quote unquote acquire a new subscriber and bring them on The Daily Upside. And basically it's a very low bar to have someone sign up to a free newsletter. So we're able to acquire large numbers, large numbers of people at scale, but that's really where the journey begins for someone on The Daily Upside. So at that moment, they will get both a welcome email, but then they'll be introduced to our brand and our content starting on day one. So we use Campaign Monitor every day to analyze the performance of these acquisition channels. We segment the audience, so every, call it, every individual ad actually results in kind of a different tag, so to speak. And in CM where we're analyzing how that cohort of people is then engaging with a newsletter, how frequently are they opening it? How frequently are they engaging with our partners on the newsletter? And then that kind of in turn informs how we'll continue to grow the newsletter. If something works we'll double down, if something doesn't kind of quickly be able to change paths.

Simone: Amazing. So in doing our homework and having a relationship, also, with The Daily Upside, we know that you have an audience list of over 700, 000 people. Amazing, amazing, amazing. How... in the journey of relationship marketing, how did you turn the unknown to the known? Right? To get them into this subscription mode where you can provide them that relevant content. And then I can ask you, future state, given that in your market it's a little bit different, how do you plan to keep that list growing and keep your audience engaged?

Patrick: Yeah. So for us, it really comes down to why are people getting our emails? They're getting our emails to stay engaged and on top of what's happening in the global economy and corporate America. So for us, it really all does come down to content. We're in a world where there's constantly an overflow of information. So if we can act as a trusted source where you're going to get a curated view on what's happening, angles on stories that you haven't seen elsewhere, and basically just a funnel to see the world in a more sane view than you'll get on social media, for instance, folks are going to open the newsletter every day if they continue to trust the content. So for us, a lot of our investment has been in our content team, our writers, our journalists. And our view is that if we produce must read content every day, people are going to continue opening our emails, which is definitely the goal.

Simone: Got it. Specific to campaign monitoring in Campaign Monitor, in that journey, where do you see them being the biggest plus for you and your team in being able to continue to grow that list and build that base?

Patrick: In terms of using Campaign Monitor?

Simone: In terms of using Campaign Monitor.

Patrick: Yeah, I'd say so we recently transitioned from a different email service provider in the last six months. And I'd say the biggest uplift by far has been just the consistency of performance. I'd say in Gmail, a lot of folks in the newsletter world are familiar with the different tabs your newsletters can end up in. And for us it was a constant battle of, are you can end up in the updates tab in Gmail or the promotions tab? And when we transitioned to Campaign Monitor and I'm not sure anyone can really definitively say why, but just uplifting overall reputation with the important inbox providers, and just consistency of deliverability has really been significant. In a way where for our partners, we can know with much more certainty how many emails are going to be opened every day, what engagement rates are going to look like when there's predictability of performance. So we're super happy so far.

Simone: Got it. In the industry, right, as part of relationship marketing, we have two other steps. We have the personalization and then you know, you build that retention, that loyalty base. Can you provide some insights since this may be a little bit different within your industry? Where do you see this working for you? Will it work? What is your perspective on the last two legs of relationship marketing?

Patrick: Yeah, I'd say it really does come down to how those two pieces interface with how we grow the audience. So for us, once we welcome a new reader to The Daily Upside, which we love doing, it is about using, I'm not sure if it's personalization, but using the tools that CM provides to be able to analyze the different cohorts of readers who are really true TDU believers versus people who are just engaging occasionally. Making sure we're focusing on those high value subscribers. And I think for us, it'll come down to learning more about who those people are. We survey the audience and give different surveys to, depending on how engaged someone is, figure out why they like The Daily Upside, and then we'll use that to inform how we grow the business in the future, what new products we introduce and things like that.

Simone: Patrick, 50% open rate is extraordinary, especially for newsletters. Can you provide some insights onto the origin around that, your tools, the partnerships that you're using to achieve? Right. Such open rates?

Patrick: Definitely. Yeah. I think over the last five, six years, the newsletter space has definitely, I wouldn't say it's overly crowded, but there's definitely more players than there were seven or eight years ago. But I think what we were able to do in the early days is actually find white space in the market by way of partnership. So in the early days we did a marketing and syndication partnership with The Motley Fool, which is a brand which has been around for two decades, three decades, perhaps. And a lot of the readers that we acquired from that relationship were folks who were not reading, call it some of the other financial newsletters out there. They were older in their careers and generally just didn't fit a demo that some other newsletters were specifically targeting. So we found a large amount of white space that we were able to take on. And a lot of those folks had not really perhaps seen a newsletter like ours written in the way it was written. So it ended up coming down to finding pockets of new audience. And at the end of the day, it still does come down to content and creating a valuable product for folks. So...

Simone: Yeah. How are you in collaboration with Campaign Monitor? How are you using this data to continue to drive subscription and continue to retain your audience?

Patrick: Yep. So every morning when we send out our newsletter on Campaign Monitor, we're sending from different segments. So our core segments that are broken up by channel, so we can gather data and assess where the most value we're getting from our marketing activities. So if we learn for instance, that one particular piece of a specific marketing initiative that we're perhaps is driving tens of thousands of new subscribers, that's great. And every newsletter wants to have a lot of subscribers, but ultimately it's the segmentation tool of saying, " Okay, we have all these new people, but are they actually opening the email? Are they clicking on the links in the email where we can continue to underwrite spend in those channels?" So I'd say for CM specifically, it's the segmentation tools that allow us to peel in to the next level of data.

Simone: Fast forward into the future, where would you see The Daily Upside in terms of the relationship that you'll continue to have with your audience?

Patrick: I think for us, we'll definitely look to eclipse a million subscribers hopefully in early 2023. We did, I guess six x'ed the audience size in 2022. I don't know if we'll end up with 6 million subscribers at the end of 2023, probably not. But we have high ambition to grow the audience. And think there's a large adjustable market for our product, but I think we'll continue to roll out new products over the next year, introduce another newsletter that's perhaps more focused on what were our core strengths, business finance, and specifically Wall Street. So I'd expect product roll- outs in the next six months or so.

Simone: For entrepreneurs who want to get into your space. Any advice? Not your secret sauce, but any advice?

Patrick: I'd say looking back at the journey of The Daily Upside, we're a fairly mass market product in the sense that anyone can really sign up and understand what we're doing and perhaps even be interested in it. And that's great because our ceiling is very high, but it is a competitive way to go about starting a new business to have an addressable market of Infinity. And I'd say so I'm not saying I would do anything differently, but I think there is value in having a specific target, perhaps a more narrow target, for launching a new product in media. You've seen a lot of companies actually get very large by focusing on specific niches. And a lot of M& A activities has come from folks in that, call it more narrow, niche oriented publications. So the other thing I'd say is just to kind of stick with it. If you are kind of an entrepreneur for us, we saw, or when it was just me working at The Daily Upside in early 2020, I saw other entrepreneurs and media start things, quit things, start another thing, and quit the next thing, before I had even really gotten halfway through The Daily Upside journey. And it's not like we had overnight success. It takes a long time to build an audience, it takes a long time to build trust with an audience. So I'd say yeah, just stick with it.

Simone: Yeah. The commitment and the hard work gets you to where you are today and we want to be continuing being part of that journey. Right? So you're sitting here, you're representing an outstanding seven member team, right? And I know that we have Campaign Monitor to actually match that. So tell us what's the suite about Campaign Monitor that you use, any specific features that you and your team really and truly hone into that makes your day much easier day every day?

Patrick: Just in terms of what news, what I'm focused on, and what other newsletter operators are focused on, I'd say as we were talking about before, it does come down to the predictability of performance. So when the team is sending the newsletter every morning, we know it's going to be delivered in two, three minutes at the most. On some other platforms, when you're sending to 700,000 folks, it can take 10, 20, 30 minutes. Where for a news product, that's actually a material impact to your readers. So the predictability of being able to send newsletters at scale. The predictability of knowing how inbox providers are going to treat the email. Where the email's going to be delivered, has been night and day for The Daily Upside. Yeah, I'd say another thing that we use is just the metrics that Campaign Monitor provides on a campaign level, the speed, efficiency at which we can gather data from each campaign flight. And use that to inform really every aspect of our business has been paramount.

Simone: All right. Last question for you. Are there any trends, hurdles that you can see those in the media space will face as we go in, when we look two, three years into the future?

Patrick: Yeah, great question. I'd say over the last two, three years, there's been a wave of newsletters that have started, perhaps folks that wanted a different type of role during the pandemic, where you saw a lot of creators even leave large established media companies to start their own thing. I think over the next... and it's already happening, but over the next six months I think you'll see a lot of folks realize that there are benefits to being on a platform, in terms of distribution. And also in terms of running a business. It's not easy to be a writer, but also run the business. So I think of the hundreds, perhaps thousands of newsletters, definitely thousands of started. I think you'll see some consolidation happen, folks kind of joining together, and basically kind of a little bit of an unwinding of the creator economy that made a lot of sense during the pandemic, where the whole point was to keep people apart and have everyone do their own thing for a little bit. I think as the world has opened back up, I think you'll see a lot of people kind of reconsolidate. And the leaders of the space, I don't want to say take advantage, but reabsorb some of the talent that was spread out. So almost a re- bundling so to speak. I think will come in the newsletter, but also more general creator economy.

Simone: Thanks for sharing your perspective with us. So thank you. Audience, we want to say major thank you to Patrick Trousdale and The Daily Upside for providing us insights and sharing his journey and sharing his team's journey with us. Thank you so much and much speed ahead.

Patrick: Thank you so much and thanks so much for having me.

Simone: Don't forget to sign up everybody. The Daily Upside.