WEBVTT 1 00:00:00.140 --> 00:00:08.440 [upbeat music] Welcome to the Rebooting show, where each week I have a conversation with someone building a sustainable media business. I'm Brian Morrissey. 2 00:00:08.780 --> 00:00:19.940 This week I'm joined by Patrick Truesdell, the founder of the Daily Upside, a newsletter publisher whose flagship email now reaches eight hundred and fifty thousand people with a mix of business, finance, and economics news. 3 00:00:20.440 --> 00:00:30.880 The Daily Upside is in expansion mode, having recently acquired a patent newsletter and with plans to roll out a new newsletter focused on the intersection of Wall Street and Washington. 4 00:00:31.340 --> 00:00:44.280 I wanted to have Patrick on to discuss how the Daily Upside has grown so quickly since Patrick began it in two thousand and nineteen, and how he thinks about expansion and not trying to do too much too soon as basically a bootstrapped organization. 5 00:00:44.740 --> 00:00:55.720 As always, I'd love to hear your feedback and even your guest suggestions. I'm bmorrissey@therebooting.com, and here's my conversation with Patrick. [upbeat music] Patrick, welcome to the podcast. 6 00:00:55.920 --> 00:01:05.760 Appreciate you joining me. Brian, it's awesome to be here. Thanks so much for having me. All right, so the Daily Upside, you started this in, in two thousand nineteen. Now, you-- 7 00:01:06.740 --> 00:01:12.720 your background, you were at, like, Guggenheim, right? So, like, what did you see exactly that was the opportunity back then? 8 00:01:12.780 --> 00:01:26.140 Because, I mean, honestly, Morning Brew and The Hustle were successful, but what was the opening that you saw for, like, a business finance start your day, figure out what's going on in the economy newsletter? Yeah. 9 00:01:26.260 --> 00:01:39.470 So yeah, I started The Daily Upside in September twenty-nineteen, and I'd, you know, definitely seen the Hustle, Morning Brew grow up into, you know, really, you know, proper sizable media companies. 10 00:01:40.380 --> 00:01:55.640 I think I was really looking for the next level of, of color and commentary, something that would more cater towards someone in finance specifically. So basically, I, I had worked at B of A in industrials as an analyst. 11 00:01:55.860 --> 00:02:04.500 I had worked at Guggenheim covering healthcare and covering media and tech. So I'd basically seen a bunch of different industries from an investment banking perspective 12 00:02:05.400 --> 00:02:18.010 and, you know, thought that in, you know, as you said, the morning, uh, roundup landscape, there could be something that covers a broad swath of different industries and goes a layer deeper with longer stories, 13 00:02:18.980 --> 00:02:29.940 you know, with, with a little bit of a Wall Street angle in terms of the depth of, of the stories. So that was the, the, the initial thought. But, like, who did, who did you think it was for? 14 00:02:29.980 --> 00:02:36.800 Like, who did you think was not being... didn't have, like, an option in the market? Was it for people, like, who... 15 00:02:36.940 --> 00:02:48.220 And 'cause I think that, that feeds into the business model, what I'm getting at, like, is it's for people who, who are gonna use this for their jobs or just, like, curious about, like, the world around them and, and because it affects them, and we all see this. 16 00:02:48.280 --> 00:02:55.000 Like, we're all, like, inflation experts now, even if we're not in the finance world. Yeah. No, I don't think it's a pure... 17 00:02:55.320 --> 00:03:06.700 it's definitely not a pure B2B publication, but in the early days, Brian, I, I really was writing it for myself almost literally and figuratively. There was, you know, a hundred people that saw the first newsletter. 18 00:03:07.620 --> 00:03:17.640 So I really was trying to cater towards people who w- w-would enjoy and, and did enjoy a morning roundup, but wanted a little bit more depth of, of information. 19 00:03:17.740 --> 00:03:29.609 So I think that meant in the early days it was, it was definitely people on, on Wall Street, uh, reading the newsletter, and then more aspirational retail folks who wanted to go deeper on investing in finance. 20 00:03:30.520 --> 00:03:43.300 You know, and those companies you mentioned earlier, they're, they're great, and they still are great, but I think the, The Daily Upside, our, our intention is to strictly focus on business and finance and peel out more 21 00:03:44.480 --> 00:03:54.710 thematic trends and, and insights that, that could be useful for someone perhaps looking at their portfolio or, or thinking about their business. So yeah, that was the intention. Yeah. 22 00:03:54.740 --> 00:04:02.590 But it wasn't, like, a generational play, right? Because I feel like the Morning, Morning Brew and Hustle, like, had that generational angle too, and I think it's good. 23 00:04:02.660 --> 00:04:11.400 Like, you can overlay different, like, lenses, and that's important. And, and a generational lens is, is one. I mean, the problem is it goes away. Like, we all get older. It's the fate. 24 00:04:11.560 --> 00:04:20.899 I mean, that's the, that's honestly the best, best case scenario is you get older. Otherwise, not good. But what... It, it seems like you didn't have the generational angle to it. 25 00:04:21.740 --> 00:04:29.940 No, we were never gonna try to go out and be the next, you know, business news for young people. I mean, that was already being done very, very well. 26 00:04:29.980 --> 00:04:44.520 To be honest, we kind of stumbled upon, I'd say, some white space in the market for older folks who perhaps had never really seen the conversational style of a newsletter like the one we were trying to put out. 27 00:04:45.200 --> 00:04:57.340 In the early days, we did a partnership with The Motley Fool, and their audience definitely skews older in terms of, of demo, and those are folks who weren't reading the newsletters, uh, you just mentioned. 28 00:04:57.400 --> 00:05:07.880 So kind of inadvertently stumbled upon, you know, uh, great white space for, for folks who didn't have their newsletter of choice yet. Yeah. 29 00:05:08.000 --> 00:05:16.320 So I wanna talk about The Motley Fool with the, you know, growing this 'cause, I mean, I think you're at, like, eight hundred and fifty thousand now. I don't know. The number keeps going up. 30 00:05:16.360 --> 00:05:22.580 Every time I was doing my research, I was like, "How the [laughs] how the... How you got to, like, three hundred thousand? How you get to seven hundred thousand?" 31 00:05:22.660 --> 00:05:28.520 Then you're, like, looking for, like, a web developer, you're like eight hundred and fifty thousand. I mean, so we're gonna get into that. 32 00:05:28.660 --> 00:05:37.860 But, like, let's start with the product itself because you, you didn't, you don't have, like, a quote-unquote, "content background." I guess you sort of do, like, you know, in investment banking. 33 00:05:38.000 --> 00:05:48.820 But, like, it's interesting to me, like, you d- you, you made the product and you continue to, like, to a degree. I'm sure you're not as much anymore. But which I always, like, I respect that, right? 34 00:05:48.850 --> 00:05:52.540 [laughs] People making the product themselves, because I think you get, like, sort of... 35 00:05:53.000 --> 00:06:00.060 When you get your hands dirty rather than just, like, you know, hire someone to it, you start to recognize, like, first of all, you're just closer to the product itself. 36 00:06:00.080 --> 00:06:15.140 But one of the things that you said that really stood out was conversational, um, and I think that's what-That's what's different with, with newsletters and, and podcasts, honestly, and, and even live events, and that's why I was drawn to this area, 'cause I think that's pretty powerful right now. 37 00:06:15.600 --> 00:06:30.920 But explain how you thought about, like, integrating a conversational and what that means, like a conversational tone to, to, you know, what oftentimes is, is, is fairly dry and factual reported news. Yeah. So 38 00:06:32.080 --> 00:06:35.240 again, I started in September 2019. 39 00:06:35.880 --> 00:06:46.780 I spent the first three or four months trying to figure out what exactly the product was going to be, who the audience was going to be, what the publishing schedule was gonna look like. 40 00:06:46.920 --> 00:06:58.320 And a couple months after that, the pandemic hit, and suddenly there was an incredible amount of economic and financial chaos happening, obviously, 41 00:06:59.320 --> 00:07:07.980 and frankly, a tremendous amount to unpack, try to figure out what was happening with the economy, what was happening with the stock market, what was happening with businesses. 42 00:07:08.940 --> 00:07:17.560 And, you know, there was obviously a tremendous amount of reporting happening, and I think I, you know, I, I was definitely... 43 00:07:17.600 --> 00:07:24.850 I was writing the newsletter for the first two years and settled into a groove where the primary value add to the audience was 44 00:07:25.800 --> 00:07:35.179 dissecting and unpacking all of this craziness happening in the markets, but doing so in 450 words. 45 00:07:35.820 --> 00:07:43.500 Whereas you might need to read, you know, half of the Wall Street Journal to really understand what was happening with, with Hertz or Carnival. 46 00:07:44.260 --> 00:08:05.370 I think the value add of what I wa- what I was trying to do was unpack all that in as few of words as possible where, where someone could really feel like they understood what, what was happening, and even perhaps in an enjoyable way, as, as crazy as that sounds, giving what, what was happening, but bring some levity to what was a pretty dark time. 47 00:08:06.280 --> 00:08:18.830 I think that's kinda what made The Daily Upside work in, in the early days, was ability to synthesize and have almost like an ex- an explanatory tint to the content without being too, too formal. 48 00:08:19.720 --> 00:08:31.950 Yeah, that proved to be the winning formula during the pandemic. Mm-hmm. Do you... I-I found it, 'cause I remember talking, it's funny, probably at a similar stage, I did a podcast with Austin Rief at- Mm... 49 00:08:31.950 --> 00:08:40.260 at Morning Brew a, a few years ago. And I remember him, like, saying, 'cause I was like, particularly at the time, I was like, "Well, when are you gonna do... You're, you're aggregating a lot of content. 50 00:08:40.300 --> 00:08:49.460 You're not, you're not, you're not, you're not reporting." He's like, "Ah, we, we don't wanna do that, right?" And they sort of changed as, as they matured. Like, how do you think of that line? 'Cause I, I don't... 51 00:08:49.810 --> 00:09:06.680 I, I think a lot of times the, the, the capital J journalist people, like, they, like, sort of dismiss, like, aggregation, 'cause, I mean, we went through these periods of aggregation in which I think a lot of what was being done, you know, back then was kind of, kinda cheap because it was about algorithms and stuff like this. 52 00:09:06.760 --> 00:09:18.040 But, like, you know, packaging stuff for people to be able to easily digest, I mean, the reality is, you know, I read the FT and The Wall Street Journal, like, every day and, and it's a lot. It's a lot. 53 00:09:18.120 --> 00:09:25.860 [laughs] How do you end up thinking about that? 'Cause I, I always think about it's like you gotta, you gotta start from what the audience needs and then work your way backwards. 54 00:09:25.940 --> 00:09:29.440 It's like this is not, like, some kind of religion or something like that. 55 00:09:29.469 --> 00:09:38.980 [laughs] Like, you're just trying to, like, help people, you know, either understand the world better or explore some topic or do their jobs, uh, better and make more money. 56 00:09:39.220 --> 00:09:44.320 But how do you end up thinking about, about that, particularly as the company grows? Yeah. 57 00:09:44.400 --> 00:09:54.560 I think, I guess I'll start off by saying in the early days, there really is no other choice but to do some form of curation and analysis. 58 00:09:55.440 --> 00:10:06.220 Unless you go out and raise a, you know, a boatload of venture capital money, you know, you're not gonna be able to go out and, and hire 10 great reporters on day one who can do original reporting. 59 00:10:07.080 --> 00:10:16.920 So, you know, in some ways, startups like, like Austin's and, and mine really have no choice but in the early days to bring value some other way. And curation is... 60 00:10:17.700 --> 00:10:28.400 I mean, there is, I think, value in high-quality curation, choosing stories that people are in- interested in, that can cater to a large, you know, swath of, of the audience. 61 00:10:29.240 --> 00:10:43.620 That's definitely an art that I still care deeply about. I'm still involved in story selection and, and guiding what we're covering. But for us, I think it, it will be an evolution. I do think there is probably a... 62 00:10:44.440 --> 00:10:49.060 I don't know if it's a cap, 'cause clearly newsletters have gotten very big just doing curation. 63 00:10:49.090 --> 00:11:00.280 But some element of creating a durable and sustainable media business to me will involve, you know, more enterprise original reporting over time. 64 00:11:00.540 --> 00:11:18.680 Because if you do just strictly focus on a, a voice or a specific persona, I do think there, those probably have waves, and I think we've seen waves where a specific per- persona you're writing to is interesting for a while, and then it, you know, perhaps fatigues. 65 00:11:19.510 --> 00:11:27.540 I don't necessarily think that's true with a, a, a company that's doing original reporting. [gentle music] So that's definitely the direction I'm, I'm looking to head in. Yeah. 66 00:11:47.240 --> 00:11:58.540 You are looking to eventually get into more original reporting. Definitely, and I think, you know, started to do it on, on The Daily Upside. We, you know, we're, we're talking to sources. 67 00:11:58.620 --> 00:12:09.760 We're, we're starting to build that type of work on the core newsletter. And then for the additional verticals, which I'd love to talk about, I think we're gonna be doing it from day one, and are doing it. 68 00:12:10.040 --> 00:12:13.184 So yeah, I think it's gonna be important.All right. 69 00:12:13.224 --> 00:12:21.924 So I wanna get to new verticals, but first, like the growth, 'cause you're at, like, you know, a lot of these newsletter growth stories, I mean, some of them are, like, pretty tremendous. Like, right? 70 00:12:22.064 --> 00:12:31.484 [laughs] Like, I'm reminded, I'm getting a little bit of flashbacks, you know, to some, some previous years. But I think I, I'm learning more about, like, how, uh, the dynamics of this. 71 00:12:31.544 --> 00:12:42.524 So talk to me about how you go from zero to, like, 850,000 in a couple of years. Few years, I guess. Motley Fool was, was critical, right? It's definitely critical. 72 00:12:42.584 --> 00:12:52.384 I mean, there's no way me with, you know, my computer and my keyboard w- was gonna be able to get it off the ground without, without either raising money or doing a partnership. 73 00:12:52.464 --> 00:13:02.124 I, I chose to do the partnership, and they were amazingly helpful. It... Their business was, was doing very well in the early days of the pandemic, right? It was meme stocks. 74 00:13:02.184 --> 00:13:15.244 It was, uh, GameStop, and people could- Yeah... not get enough of content that, that they were putting out. And I think Daily Upside benefited from, from that flow and, and that traffic. So yeah, a, a significant- So-... 75 00:13:15.304 --> 00:13:24.134 portion. Sorry, go ahead. So how did it work? I- I'm sorry. How did the partnership work? How did you end up... And, like, what were the numbers? I, I saw Simon Owens. It, it was a great podcast. 76 00:13:24.184 --> 00:13:30.644 You should check it out, uh, Business of Content. He did one with you, and you guys talked about this a little bit. But, like, I think, like, you went from, like 3,000 to 10,000. 77 00:13:30.664 --> 00:13:41.164 But explain the partnership itself and how, how that gave you a leg up. Yeah. So it was a fairly structured partnership. There were a couple different elements to it. But essentially, 78 00:13:42.084 --> 00:13:54.174 they, after kind of testing The Daily Upside and sussing out whether or not we had a viable product, you know, I was ultimately able to convince them of that in mid-2020. 79 00:13:54.644 --> 00:14:05.644 And from there, they, you know, had an economic interest in The Daily Upside after we struck, struck a partnership, and basically distributed our content on their website. 80 00:14:05.924 --> 00:14:19.044 They offered The Daily Upside to folks on, you know, both their, their core customer list, on their marketing list, and, you know, basically said, "We've got a new partnership with a company called The Daily Upside. 81 00:14:19.724 --> 00:14:30.704 We think it's great. You should check it out." And again, it was a crazy time for the markets. People couldn't get enough of this type of content, and ended up being massive growth driver. 82 00:14:30.744 --> 00:14:42.524 I mean, our predominant growth driver in, in 2021. Okay. So how, how big did that get you? I mean, you were doing other things. I'm sure you were doing newsletter swaps, maybe buying some ads, and stuff like this. 83 00:14:43.224 --> 00:14:52.844 I don't know the exact numbers off the t- top of my head, but I, I always say roughly 80% of our first 80,000 subscribers were from that partnership. Oh, damn. 84 00:14:53.433 --> 00:15:02.724 And that w- I mean, I could be wrong, but, like, the dynamics of growth I find are, like, really interesting 'cause it really compounds. Like, it's like you get more subscribers, you get more subscribers. 85 00:15:02.864 --> 00:15:11.664 And, like, you have to get over that, like, hump, and that's why I find it really interesting, this, uh, this approach with, like, the partnership with, with, with someone who already has distribution. 86 00:15:11.734 --> 00:15:20.364 'Cause, like, in media, like, you can make something and, and I think a lot of, you know, journalists think it's like, oh, if you just... You know, if you just make it, like, people will find it and it's really good. 87 00:15:20.404 --> 00:15:30.904 It's like, maybe. [laughs] You know, distribution has always been the, you know, an incredibly important part of media, and y- you gotta get distribution. 88 00:15:31.024 --> 00:15:44.384 And, and once you do get to a certain level, you know, whether it's referral programs or just, like, growth just becomes easier, right? Yeah, definitely. I mean, I definitely have the opposite view. 89 00:15:44.444 --> 00:15:54.204 I, I think you could write the most beautiful story in the world- Yeah... and unless there's a proper, you know, strategy to get it distributed, no one will see it. 90 00:15:55.084 --> 00:16:01.054 So yeah, I, I, I think it's, it is, it's critical to have these, have these strategies and these partnerships. 91 00:16:01.124 --> 00:16:07.864 And ra- raising money can be a, a big part of it, 'cause you can go deploy ads on, on Facebook and Twitter to get your, your message out there. 92 00:16:07.884 --> 00:16:15.444 But there definitely is a, is a tipping point where enough people have, have heard of you, where organic traffic starts to build. 93 00:16:16.304 --> 00:16:26.604 And once you get, you know, past a certain point for, for a business like, like ours, can start generating ad revenue and then deploying that ad revenue into additional growth, and- Yeah... 94 00:16:26.644 --> 00:16:40.364 that becomes the, you know, the strategy. Yeah. So, so this was, like, self-funded. Like, you didn't take outside capital. Essentially. There's a very small financial component to the Mo- Motley Fool deal. But it... 95 00:16:40.404 --> 00:16:51.303 Yeah, I'd consider us a, you know, pretty much a, a bootstrap business. Right. So talk to me about the, the, the distribution strategy. Like, what did you deploy to... 96 00:16:51.684 --> 00:17:00.284 I mean, it seems like Motley Fool was a great, like, you know, and continues probably to, you know, generate a lot of, like, new subscribers. 97 00:17:00.304 --> 00:17:11.484 But, you know, to get it to 850,000 [laughs] newsletter subscribers is, like, pretty impressive. So, like, what, what, what were the biggest levers that you found in the growth story? 98 00:17:12.484 --> 00:17:21.844 Uh, as you said, I mean, basic things like newsletter swaps in the early days, newsletter... Buying ads on other newsletters are great. 99 00:17:21.984 --> 00:17:27.984 I think that's where we have gotten our most engaged subscribers are from people already consuming the medium. 100 00:17:29.044 --> 00:17:36.784 Definitely, uh, probably impossible to get 850,000 subscribers from just buying ads on newsletters or doing swaps. 101 00:17:37.924 --> 00:17:49.424 So ultimately, you kinda have to turn to the scalable channels like Facebook, like TikTok, like YouTube to, you know, d- drive massive volume of, of subscribers. 102 00:17:50.304 --> 00:18:01.034 Organic at this point is, is I think our, our largest channel of, of where we're getting new subscribers, people who just- Mm... hear about us somehow or maybe see one of our stories and then sign up. 103 00:18:01.944 --> 00:18:15.284 But certainly from a paid acquisition perspective, yeah, the large scalable channels are, are, are... Y- you kinda need to figure out how to make those work in order to get to those large numbers.Yeah. 104 00:18:15.324 --> 00:18:26.684 So I mean, once you get, like, a big enough base, you can start selling ads. And were you doing that mostly directly? I'm sure you used some of the marketplaces and outsourced ad sales outfits that are out there. Yeah. 105 00:18:26.744 --> 00:18:40.254 I mean, we did a lot direct, and um, when I say, I say we a lot, even referring to 2021 when it was really just me. But those were, were great days. I mean, it, it... the ads would pretty much sell themselves. 106 00:18:40.284 --> 00:18:51.984 We had a lot of inbounds of people who, you know, were advertising on similar newsletters who wanted to find more. So those were, you know, look back at those as very pleasant ad selling, ad selling [chuckles] days. 107 00:18:52.984 --> 00:19:06.004 Yeah, inbounds. Those were crazy times, though. Yeah. I think I'll, I'll, I'll look back with fond memories, uh, despite how tough of a time it was for, for the world. It, it was great for financial media. Yeah. 108 00:19:07.004 --> 00:19:21.244 Okay, so but, like, you, you were selling yourselves, like, one placement per, per email? One placement per email. Eventually we rolled out a secondary slot. But yeah, and it was, I'd say, mo- mostly direct. 109 00:19:21.284 --> 00:19:32.524 We definitely worked with some outside sellers, some, some platforms. But yeah, we just had enough brands that we either tactically re- reached out to or came to us via inbound. 110 00:19:33.424 --> 00:19:44.184 And luckily or, or, or thankfully, enough performance that they saw on the newsletter where we had mostly repeat business. Yeah. So what, what, what is the, like... 111 00:19:44.204 --> 00:19:52.524 What's, like, the endemic advertising category for The Daily Upside? Like, investment products? Or wh- where do you find, like, most of the demand? 112 00:19:53.284 --> 00:20:02.744 I'd say, yeah, financial platforms tend to do really well on, on The Daily Upside. You've got a lot of other... We've got business owners and business operators who also read The Daily Upside, of course. 113 00:20:02.784 --> 00:20:16.924 So we have B2B SaaS products that can do really well. And then, yeah, consumer products also do well on The Daily Upside, and we try to have a mix of sponsors so it's not financial advertisers 24/7. 114 00:20:17.004 --> 00:20:29.764 I think that would get old. So we definitely intentionally have a mix of different types of sponsors. Okay, cool. So how do you end up thinking, 'cause this is when, I mean, you're, you're expanding now. 115 00:20:29.833 --> 00:20:38.664 'Cause I think at, at some point, particularly with email newsletters, you get to the point, it's like, okay, we have distribution, we got... What, like, how do you judge engagement, like, for your... 116 00:20:38.804 --> 00:20:44.284 I mean, open rates are open rates, but, like, I don't know. How do you- Yeah, open rates is- How do you measure it? 117 00:20:44.384 --> 00:20:55.384 Yeah, open rate's a little less reliable now with, uh, iOS changes, but we still look at open rates, and we have different ways where we can kind of tease out if a open is a real open. 118 00:20:55.454 --> 00:21:02.004 So we, we definitely use some modified version of open rates as an engagement, uh, metric. 119 00:21:02.064 --> 00:21:14.484 Click rates continue to be really important, and we kind of use the two in tandem to see, all right, if someone has opened, you know, the last 200 newsletters but haven't clicked a single time, 120 00:21:15.384 --> 00:21:27.944 maybe that's a function of some technology artifact or an iOS change, not an actual person. So we're still using the basic KPIs, but I think a little more strategically to judge engagement. 121 00:21:28.064 --> 00:21:50.224 [gentle music] So what is good, like, what is good now? 122 00:21:50.273 --> 00:21:59.634 'Cause I mean, with open rates, for those that don't know, like, you know, A- Apple basically is doing all sorts of things to screw up, like, anything with digital media at this point [chuckles]. 123 00:21:59.684 --> 00:22:01.464 But everyone loves Apple, so they can do whatever they want. 124 00:22:01.604 --> 00:22:14.844 But they're, they're protecting people from the evils of, of newsletters, uh, knowing who's actually opening their [chuckles], their emails, which I had never really understood why that was, like, a major privacy invasion, but apparently it is. 125 00:22:15.064 --> 00:22:25.264 And so they're basically just, like, auto-opening, basically, emails. So, like, your open rates are, most people's open rates are inflated, right? Definitely. 126 00:22:25.333 --> 00:22:35.204 It's in my sales kit, but it's still, I still say I've got 50% open rates, 'cause I do, but I just don't know exactly how accurate it is. [chuckles] What is a, what is a good, like, click rate for, like, any... 127 00:22:35.243 --> 00:22:47.884 Like, what do you aim to, to have as a click rate? I think when we have a sponsor that, that really connects, we can have above a 1% unique click-through rate based on unique opens. 128 00:22:47.944 --> 00:22:55.884 So let's say we have, just throwing out round numbers, 300,000 unique opens on any given day. There were 3,000 unique clicks. 129 00:22:56.444 --> 00:23:03.884 We'd consider that a pretty successful sponsor where there's deep, uh, it's deeply resonating with the audience, I'd say. Yeah. 130 00:23:04.084 --> 00:23:10.264 And most of your sponsors are judging the success of their campaigns based on how many clicks they get to their site? 131 00:23:10.804 --> 00:23:16.404 Yeah, I'd say we, we still have a lot of performance sponsors we're trying to, to round out for different types of sponsors. 132 00:23:16.664 --> 00:23:26.044 Yeah, click-through rates is always going to be important, and for us, and, and frankly, this is something that's helped us do well, specifically with the financial partners, is 133 00:23:26.964 --> 00:23:40.184 how much asset volume is kind of moving on a down funnel activity if we're partnering with a financial platform. Are Daily Upside readers actually investing, has been important for our, for our sponsors. Yeah. 134 00:23:40.664 --> 00:23:46.844 So let's talk about expansion, because, I mean, you get to a point, you know, you've got great distribution, you've got an engaged audience, and you got insight. 135 00:23:46.864 --> 00:23:57.744 You can either go deeper, you can try, like, a, like, a premium version. I mean, obviously The Motley Fool knows this. They have g- great distribution. They, they have a, like, a very big paid component. 136 00:23:57.784 --> 00:24:10.384 You can go that route. You could have more specialized products, or you can expand, like, and, and maybe this becomes the flagship product and more specialized products can, can be monetized in a different way. 137 00:24:10.804 --> 00:24:17.504 E- explain how you ended up thinking through and mapping through the different expansion pathways, 'cause there are a lot. 138 00:24:17.604 --> 00:24:26.008 Once you get-To some kind of version of product market fit, and, you know, it's going, like, you have to make a decision. Yeah. I think 139 00:24:27.148 --> 00:24:40.388 for us, the goal was always gonna be to create one, you know, large and, and substantial, and hopefully top of mind product for, for folks for, you know, the core, core newsletter. And then from there, 140 00:24:41.348 --> 00:24:52.018 my thought process was, you know, there's definitely verticals that we think we could expand into and, and do well. You know, tech was always going to be one of them. 141 00:24:52.048 --> 00:24:56.698 Some version of a deeper Wall Street newsletter was always gonna be one of them. To me, the, 142 00:24:57.848 --> 00:25:13.188 the goal was always to think through, like, what's a really unique product that doesn't already exist in, in the marketplace where people will not just sign up for this because it's the Daily Upside's tech newsletter or Wall Street newsletter. 143 00:25:13.788 --> 00:25:26.748 But how can we make it really special, really unique? So PatentDrop is... was our, our second product. We actually acquired a newsletter, a Substack newsletter, call it two months ago. 144 00:25:26.888 --> 00:25:40.208 And I can give you some, some background on the newsletter. What it does, it, it basically has some scraping technology that goes into the US and patent and trademark database, pulls most... 145 00:25:40.248 --> 00:25:53.328 pulls really any type of patents you want based on what companies you're interested in. And from there, you can see, all right, what is Meta filing? And they file a million patents, as do most tech companies. 146 00:25:53.758 --> 00:26:08.688 But we can kinda easily sift through what the most interesting ones are, what strategically seem the most, uh, important, and write kind of a future of tech newsletter based on that information. So I basically... 147 00:26:08.998 --> 00:26:19.228 We, we had bought ads on PatentDrop in 2021, or sorry, 2022, and, you know, had a very engaged audience, was very unique, we thought. 148 00:26:19.528 --> 00:26:30.787 And basically, the opportunity to acquire it came about, and to me, s- s- struck me as an obvious next step for The Daily Upside for a unique product in a vertical we, we care about. 149 00:26:31.568 --> 00:26:41.308 So that's kinda how I, I thought about it. And how do you, how do you... How are you thinking about monetization long term? I mean, 'cause it would seem like, you know, if you're... 150 00:26:41.348 --> 00:26:50.918 I mean, maybe I'm unique in that, like, I'm not sure if I'd need, like, a daily patent. Like [laughs] maybe it's weekly. I wouldn't... I don't need that much patent stuff. 151 00:26:51.388 --> 00:26:58.368 But if I was like, you know, i- if this was my job, yeah, I mean, I need to, like, you know, know who... Like, you know, that's... 152 00:26:58.408 --> 00:27:08.008 It's a signal, and everyone's looking for signals, whether you're investor, whether you're a hedge fund or whether you're, you're in, you know, a competitor. You're always like, you need that kind of... 153 00:27:08.108 --> 00:27:20.208 That's closer to intelligence, really. How are you thinking about that? Is it... Do you see a pathway to that being your first, like, paid product? We don't have any definitive plans to make PatentDrop a paid product. 154 00:27:20.268 --> 00:27:34.288 I think my, uh, our, as a team, our strategic goal is to perhaps widen the scope a little bit a- as you said. Patents, it's, it's certainly not an everyday newsletter, but even twice a week wi- will be a lot of patents. 155 00:27:34.368 --> 00:27:43.428 I think we'll work as a team to figure out exactly how we broaden slightly while still main- maintaining the integrity of the original idea. And it... 156 00:27:43.748 --> 00:27:59.548 You're right, it is very much a market intelligence product, and I think something people would pay for. My philosophy will be, let's see how large we can make this and then assess the best monetization- Mm-hmm... 157 00:27:59.568 --> 00:28:01.728 path that'll serve the audience the best. Yeah. 158 00:28:01.788 --> 00:28:13.127 I mean, if it is going deeper on these topics, and something we could only do with four or five other journalists working on it, maybe it is a paid model that, you know, we roll out to support that. 159 00:28:13.988 --> 00:28:23.268 But in bringing them in, like, you feel like, like, do you have, like, a playbook at this point [laughs] I mean, that, that you can take, like, PatentDrop and, like, scale it? 160 00:28:24.108 --> 00:28:30.228 You know, 'cause I mean, I think that's the key. It's like when, when you have, like... When you have distribution, everything, but more importantly... 161 00:28:30.728 --> 00:28:41.268 Not more importantly, but just as importantly, when you have a playbook to be able to take in another asset and be able to, like, scale it because, like, you've learned a lot over the last few years about what works. 162 00:28:41.308 --> 00:28:52.108 Like, you know, you don't just go from zero to eight hundred and fifty thousand, like, by accident [laughs]. Yeah. Well, that's... I think the beautiful part is we do have the playbook. We know how to scale newsletters. 163 00:28:52.248 --> 00:29:03.208 We have a lot of people on the Daily Upside who are interested in the future of tech, so we can simply tell our audience that we have this new product, and thousands, uh, of, of folks sign up. 164 00:29:03.588 --> 00:29:17.508 So it, it definitely is the case that the playbook helps and, you know, we'll have to alter it slightly based on the new nature of the content. Yeah. But the same basic strategies will, will definitely work. Yeah. 165 00:29:17.528 --> 00:29:23.008 But you wanna attract new audiences, right? Or is this a... Is, is it, like, the initial thing just more surface area? 166 00:29:23.058 --> 00:29:32.748 'Cause one of the things that nobody really talks about with, with newsletters, maybe they do talk about it, I just don't listen, is, you know, there's limited surface area, as they say. 167 00:29:32.988 --> 00:29:35.208 Like, you can only put so many ads in a newsletter. 168 00:29:35.268 --> 00:29:49.828 Like, you're, you're capping your business compared to other types of, of publishing because, you know, look, newsletters are amazing and everything like this, but you can't have five ad slots in a newsletter. No, I... 169 00:29:50.478 --> 00:29:57.428 Y- you definitely can. To answer your question, we'll, we'll definitely wanna attract new audiences for PatentDrop. Uh, and I think we will. 170 00:29:57.488 --> 00:30:04.048 I mean, right now there is very little overlap between PatentDrop and, and The Daily Upside, 'cause they were, they were built independently. 171 00:30:04.888 --> 00:30:18.088 So yeah, it's, it's, it's the same playbook in terms of being able to go out and, and find the audiences and figure out what, you know, what influencers to partner with to promote PatentDrop on, on YouTube, on Instagram, on Twitter. 172 00:30:19.068 --> 00:30:32.724 So new audiences, but, but same playbook.Okay, cool. So what other verticals are you targeting? Yeah. So last week, we, we announced that Leah McGrath Goodman is, is joining the Daily Upside, which 173 00:30:33.724 --> 00:30:42.524 frankly is, is, is, is quite humbling. She's prolific journalist with many years of, of breaking stories and, and covering really important topics. 174 00:30:43.544 --> 00:30:58.704 She will be leading Power Corridor, which is our new newsletter focused on Wall Street and DC, and we're planning on launching that in the middle of March. Okay. So give me the idea behind that or what, what... 175 00:30:58.724 --> 00:31:10.064 Is this like opportunistic shit you just... Or was this like we need to find someone to lead, like, this area? Like, th- this is a great area for it. Yeah. I mean- To me, it seems like a mix. 176 00:31:10.124 --> 00:31:19.924 Like, it was like, well, this is like, yeah, this thing is, is working and, like, you know, maybe the person who's doing it is like, you know, trying to figure out what to do, but I don't know. 177 00:31:19.984 --> 00:31:26.444 Explain to me, 'cause things are always, like, a little bit messier [chuckles] than they probably seem on the outside. Yeah. 178 00:31:27.024 --> 00:31:37.384 Power Corridor is definitely a more natural extension of, of w- what we are doing on the Daily Upside, focused on, you know, bringing new light to stories on, on Wall Street and, and business. 179 00:31:38.204 --> 00:31:51.884 With someone like Leah, it's, you know, w- we got to know Leah through our, uh, editor- editorial advisor, Jim Impoco, who's actually the former editor-in-chief of, of Newsweek. He knew Leah, used to work with Leah. 180 00:31:51.964 --> 00:32:07.804 And yeah, w- w- we basically got, got to talking, got to figuring out what she was interested in, in covering and how that would overlap with what we were already doing, and yeah, it, it's, it's very much an extension of 181 00:32:08.744 --> 00:32:16.824 my goal, which is to bring more enterprise reporting to, to the Daily Upside, and Leah's got a, a long track record of doing that. 182 00:32:17.694 --> 00:32:35.364 [gentle music] So yeah, w- we, we couldn't be more excited for this, this product and, and what it'll mean for us. Is it gonna have a different approach? 183 00:32:35.444 --> 00:32:44.994 Like, 'cause I, I wonder about playbooks, 'cause like there's editorial playbooks too, right? And like, so sometimes, like, running the same editorial playbook for like a new publication is not... 184 00:32:45.024 --> 00:32:56.004 Like, or you need to tweak it to some degree, but are you thinking that this is gonna be a, a, a different, like, approach from the one taken in the Daily Upside? Totally. Yeah. I think 185 00:32:56.904 --> 00:33:03.004 really from everything from how the newsletter looks, how often it comes out, it's gonna be at the outset a twice-a-week newsletter. 186 00:33:03.844 --> 00:33:17.504 We're not really gonna follow the same playbook of, of taking three stories and adding our, our angle to them. Leah's already out talking to sources and, you know, building more enterprise-oriented stories. 187 00:33:18.444 --> 00:33:28.444 I think the actual newsletter will look different. The sty- uh, of the newsletter, the style of the writing will, will be different. I think she'll... Leah will obviously naturally comes with a lot of gravitas. 188 00:33:29.334 --> 00:33:40.293 So it's not as if we're, we're trying to say, "All right, this is the voice of the Daily Upside. It's working really well for this audience. Let's go superimpose that on a different vertical." Mm-hmm. 189 00:33:40.324 --> 00:33:43.964 I think we're, we're very much gonna treat it as, as a new product. 190 00:33:44.453 --> 00:33:55.724 And there will be, you know, some co-branding elements where it's a Daily Upside powered newsletter, but it, it'll very, very much have its own look and feel and, and, and style. 191 00:33:56.624 --> 00:34:07.584 So are you thinking of this as like a, I don't wanna say a network. It's, it's like a network of like newsletters in that, like, it's not like it's the Daily Upside and then you have... Like, how are you... 192 00:34:07.684 --> 00:34:17.144 And I don't even know if you are thinking this yet, [chuckles] but like how are you thinking about, you know, as you expand into like new areas and stuff like this, are, are... 193 00:34:17.184 --> 00:34:29.384 Like, how do they all connect to each other in some ways or do they not? Are they all, like, distinct? I think, [chuckles] I mean, to be honest with you, Brian, it's something we're, we're kinda solving as we go. 194 00:34:30.204 --> 00:34:32.164 I'd say- Appreciate the honesty. Yeah. 195 00:34:32.384 --> 00:34:45.944 [chuckles] There will definitely be connective tissue that, that ties the ecosystem together, but just the way these products have materialized, it will definitely be, you know, an, an, an evolving reality. 196 00:34:46.464 --> 00:34:48.764 But no, I'm, I'm not thinking about it as a- Yeah, 'cause it's, like, so hard. 197 00:34:49.744 --> 00:34:56.454 Yeah, I've always thought it's, like, so hard because, like, you want, like, you want things to have their, like, distinct identity in something like this- Mm... 198 00:34:56.464 --> 00:35:07.594 but, like, you also have to be realistic in that getting anyone to know and to, you know, like, to give a shit about, like, a brand is, like, really hard, right? [chuckles] It's, like, super hard. 199 00:35:08.284 --> 00:35:16.744 To do it, like, repeatedly, like, [chuckles] you know, like one... another time, another time, another time, another time, another time, it's like, oh my God. 200 00:35:17.244 --> 00:35:26.224 You start to, like, wanna just go back to, like, the Yahoo approach and you be like, "Yahoo this, Yahoo that, [chuckles] Yahoo that." So I don't know, it's, it's always a big challenge I think. 201 00:35:26.444 --> 00:35:39.744 And I see sometimes with, like, newsletter sub-branding that, like, it gets, like, super chaotic. Like, Puck has, like, a lot of, like, sub-brands and I'm like, "These are too many sub-brands." Yeah, I don't wanna... 202 00:35:40.544 --> 00:35:52.184 You know, I'd, I'd say for us, I think it, it's never gonna be a network of, of newsletters where it's, you know, creators operating independently and we're really just facilitating the sends. 203 00:35:52.224 --> 00:36:03.624 That's by no means what I'm envisioning. Yeah. But defining the connective tissue I think will, will, will be perhaps a little bit looser than it is for, you know, the brand you just mentioned. Yeah. 204 00:36:04.224 --> 00:36:13.824 No, I mean, I think that's the, that's the, like, the connective tissue, 'cause there has to be... There, there should be, like, some connective tissue, 'cause otherwise you're an ad network or something. 205 00:36:13.884 --> 00:36:15.484 Like, you know what I mean? Like, I think in some... 206 00:36:15.884 --> 00:36:28.014 I've seen some, like, newsletter companies where I'm like, I don't understand, like, particularly when there's, like, a quote unquote "creator focus," I'm like, I don't really see how these things are even, like, related to each other. 207 00:36:28.064 --> 00:36:39.088 I mean, just because you change, like, all your, like, Twitter backgroundTo the same color, does that make like the, this, uh, a coherent brand? There's no connective tissue other than that. 208 00:36:39.368 --> 00:36:49.668 So, and I think it's, like, difficult because it was done in a very heavy-handed way, I think, in, in media up into this point, where it's like everyone need- everything needs to be the same style. 209 00:36:49.748 --> 00:36:52.968 Everything needs to, like, you know, look the same. Everything needs to... 210 00:36:53.008 --> 00:37:02.898 You know, and consistency is important in establishing a brand, but sometimes, like, it can, I don't know, it can be done brutally and, like, wring out any sort of individuality, and I think that's a, 211 00:37:03.948 --> 00:37:12.208 a major upside in, in, you know, like you said, the conversational aspect. Like, you need to have a bit of individuality to it. Yeah. 212 00:37:12.288 --> 00:37:23.578 Like, especially when you bring on someone of, of Leah's caliber, and just in terms of her journalism track record, there's really be no upside for us in, in imposing, 213 00:37:24.668 --> 00:37:35.188 you know, strictly what we've been doing at The Daily Upside on, on her process. People are gonna read- Yeah... Power Corridor 'cause they wanna hear from, from, from Leah, so. Yeah. Okay. 214 00:37:35.568 --> 00:37:47.078 Uh, so last thing is, is how do you think about... And yeah, I think the other thing when you think about growth is you become good at, like, newsletters. Like, you have a playbook for newsletters. 215 00:37:47.188 --> 00:37:48.488 You're good at newsletters, right? 216 00:37:48.928 --> 00:37:57.998 And then the question of the becoming, I, I'd written about this the other week about changing lanes a little bit because you have to change, you have to change lanes, but you don't wanna [chuckles] go, like, six lanes over. 217 00:37:57.998 --> 00:38:10.928 And we've seen this, like, a lot of times, particularly in the last era of media, where companies kept switching lanes into, into areas where it's like that does... Both topic areas, but also just format, like, right? 218 00:38:11.008 --> 00:38:23.148 Like, because you're good at, at newsletters, does that mean necessarily that that translates into making television shows, you know? Ozzie tried that. How do you think about, like, staying 219 00:38:24.228 --> 00:38:34.908 with what you're good at, right? But, you know, the reality is, like, newsletters has a, have a ton of upsides, but, you know, there's some limitations to it. How do you think about expanding the product set? 220 00:38:35.028 --> 00:38:45.158 Yes, it's a great question. I, I'd say I think about it hesitantly. You know, we're a bootstrap company. It's not as if we can go out and hire- Yeah... 221 00:38:45.158 --> 00:38:52.848 10 video producers to try to make awesome content for YouTube that may or may not, you know, see the light of day. 222 00:38:53.748 --> 00:39:02.308 I'd say, look, you know, we're, we're already biting off a, a couple new products with, with, uh, PatentDrop and Power Corridor this year. 223 00:39:03.148 --> 00:39:16.107 My focus for 2023 is definitely going to be scaling those two, creating the connective tissue as we talked about between, between the products. In the fullness of time, I absolutely think there are different mediums 224 00:39:17.008 --> 00:39:28.748 that we'll be able to roll out with our, our journalists that make sense and create more of an ecosystem beyond the newsletter. You know, w- we, we have folks on our team that make... 225 00:39:29.008 --> 00:39:40.108 you know, ha- have a lot of podcast appearances or television appearances in their past, where clearly there's the talent to, to build other types of products, and we're gonna continue to hire people like that. 226 00:39:41.068 --> 00:39:50.588 But I'd be lying if I said, "Yeah, in June, you're gonna see a Daily Upside [chuckles] podcast." I, I don't see that happening, so. It's a natural extension, I feel like. 227 00:39:51.008 --> 00:40:02.628 Uh, podcasting is one where I feel it, it's, it's a natural to newsletters to some degree because it's also, it's conversational. It's, and it depends on the newsletter product, obviously. 228 00:40:02.748 --> 00:40:09.468 But it's like I saw, I, I like... You know, like, I think Morning Brew, they just, like, came out with their daily podcast. 229 00:40:09.498 --> 00:40:19.408 And I thought what was good about it was that it fit the Morning Brew to me way better than Business Casual dude. It was just, it was more them. I mean, that's what they're good at. 230 00:40:19.448 --> 00:40:30.208 They're good at, like, you know, summarizing the news in a way that's, like, engaging and stuff like this. And, and I think sometimes people go a little bit too, a little bit too far afield, but whatever. 231 00:40:30.268 --> 00:40:35.268 Gotta try new things. Eventually we will. I, I don't wanna say we'll, we'll never have a podcast. I'm, I'm sure we will. 232 00:40:35.608 --> 00:40:46.648 But in terms of the im- immediate roadmap, I'd say we're just by virtue of where we are in, in the market cycle, and again, the reality that we are- Yeah... a, you know, self-funded company, it's a different roadmap. 233 00:40:47.448 --> 00:40:54.668 So are you, are you gonna focus on, on making these two work, or are you looking at other areas this year? Yeah, I'd say 234 00:40:55.568 --> 00:41:02.308 we're definitely gonna be laser focused for the next three to six months on these two new verticals. 235 00:41:02.328 --> 00:41:09.748 There's a lot of people we need to hire to make these two new products work, and call it the business ecosystem that, that lives behind it. 236 00:41:10.688 --> 00:41:20.568 So beyond that, we definitely have other verticals we're, we're gonna try to key, key into towards the, the, you know, the second half of the year and the, the back half of the year. 237 00:41:21.428 --> 00:41:33.268 But I think the thing that's benefited us the most in the past is, is just moving pretty deliberately and at, at the right speed for the type of company we are. Yeah. Couldn't agree more. Awesome. Great, Patrick. 238 00:41:33.288 --> 00:41:40.188 Well, it was great great chat. Appreciate you taking the time. Yeah, Brian, always great to talk. Thanks for having me. Thank you so much for listening. 239 00:41:40.288 --> 00:41:48.508 Again, please do send me your feedback, and my email is bmorrissey@therebooting.com. Thanks a lot to Chase Sparks, who is producing this podcast. 240 00:41:48.768 --> 00:41:57.428 If you're thinking about doing your own podcast, and again, they're hard to grow, but the depth of engagement is amazing, so don't let that scare you off, get in touch. Chase can help you out. 241 00:41:57.788 --> 00:42:13.378 He is at podhelpus, that is podhelp.us. [outro music]