How I Built and Sold a $31m Financial Media HoldCo | James Camp Interview

My guest today is Jameson Camp. Jameson is the founder of TMO Holdings, a holding company that owned financial media assets and consumer packaged goods. He exited TMO Holdings for $30 million. After that, he bought Blue Angels Hearing, a direct-to-consumer hearing aid company that they sold to Open Store 11 months later. A true buy-and-build specialist, if I may say so. Thanks a lot for coming to the Holdco Builders Show, James.

Thanks so much for having me. It's funny, it's sometimes when you're just in it yourself, you don't realize that you're doing these things. And I have like a little deal toy shelf in front of me and I do it to remind myself I've actually done some of these things that just, I'm like, oh, whoa, I did sell that business. So we did buy that business. You know, it feels kind of weird when it's in the past. So cool to hear you say it.

So we get all, we will talk about this, but you've started from somewhere. Give us an overview of your background and what led you to this career today.

Yeah, I mean, I think part of it, it's only recently been on purpose, I guess, right? I think that sort of, you know, I was just like an internet kid. I'm 36. I loved, you know, wanted to make money as a kid. And, you know, I come from the era when AOL came on a CD-ROM, and you had CompuServe and Juno and 56K modems. And I just started blogging when I was like 15. You know, started like, I don't know, AngelFire, GeoCities, these like platforms I don't think exist at all anymore. And I built a blog. I was just writing about random stuff I liked and I went pretty viral on StumbleUpon and Digg. Those don't exist anymore either. And I made like $36 on AdSense. I was like 15 or 16. I was like, oh my God, like this is in a day. And I was like, this is the craziest thing ever. Long story short, that turned into me like really doing a deep dive into display advertising and then to affiliate marketing. I became a pretty big publisher in that space and then sort of used that as leverage to build an affiliate network, a CPA network, a lead gen business. Business that called Liquid Offers. And the first thing I bought was uploadforever.com. It had been like, it was like this dormant domain that had been a file hosting website. This is before Spotify and stuff when people just host songs and movies on the internet. And we bought that. And then I turned that into a file hosting website where you basically had to fill out CPA offers to access the content. And then we sold all that a little bit later, a year and a half later. And it was a very small exit, but it was like my first I was like 20 and I was like, whoa, like this is possible. And then flash forward a long time later, I, you know, started building out this financial news website, Holdco. And that's the adult life. I'm going to skip 15 years of my life essentially for you. But that was the introductory to it, just messing around on the internet as a kid.

So being an internet kid, I think this is already a big lesson you shared being in this one industry or one world for as long as possible. But what have been the different businesses you maybe started and bought in this internet space?

I mean, I started— I mean, I used to say, you know, 2 exits, 1,000 failures. I mean, like, I generally have started so many things. I think that that's sort of where part of the thesis of buying came about, was that, like, you're just— a lot of what you're paying for in smaller acquisitions are product-market fit, essentially, right? Just proof of concept that this works. Obviously, at a larger size, you start paying for cash flow or for, you know, forward multiples of earnings. But in general, like, at a tiny, tiny stuff, you're really just buying like, does this work? Is there proof that this works? So I started everything from like a private concierge to little blogs to tons of e-commerce brands, lead gen brands that sort of failed buying-wise. I think the things, I mean, I bought a couple of random small things here or there, but the things that were significant for me were that first purchase, which was uploadforever.com. That was a file hosting website that we turned into an incent CPA network. Bought, I mean, obviously bought blocks of equity in some things. Tried to buy a shell on the public markets years ago. That was an interesting one to put a bunch of assets into. Ended up getting conned for like $100,000. That's a whole different story. Bought a direct-to-consumer hearing aid brand that we were the, like you mentioned, we sold to Open Store. We were their first acquisition. It's Keith Rabois' little aggregator PE shop out of Miami. Let's see, recently bought a small software business called Off Market. Sort of fits into my ecosystem very well. Basically, the software for finding off-market deal flow for searchers and small PE firms. I don't know, I could rant. I'm trying to think about what some of the others are that I could keep ranting on. But I think those are like significant ones for me of now. I think it didn't really click for me until like, I mean, we'd already been buying things, but like sort of the, I mean, some of the deals I did in DMO Holdings, which was like 2015 to 2020, were actually equity-based comp and like very weird structures that like, Candidly, there's a bunch of gurus on the internet talking about buying businesses for no money. And that's sort of how it could be done, you know what I mean? Like, but I didn't realize that was what was happening. We were just like taking equity in lieu of cash and doing weird, interesting deal structures. It didn't really happen for me, the clearness of this thesis until I sold DMO in 2020. And I sort of had enough money, didn't make me like super rich. But you know, I had partners and we had raised equity. You know what I mean? Like, everyone sees $31 million exit and thinks I got $31 million in cash. And I love I think that's like one of the farces of exits is that it's just not really how it works 90% of the time. But I did have enough money to like go buy a house and start looking at like, what do I want to go buy a business? What do I want to do? And it became super clear to me as I just started writing about it. Ironically, I started writing about it on Twitter and I had like 800 followers at the time. And I started writing about things I was looking at doing and, uh, business I was looking at buying and ended up obviously buying some, but it became just through that sort of like. Very modern-day version of journaling, I think, that it became like very clear that this thesis made total sense. And then the win that we had at Blue Angels hearing was just sort of undeniable that like, you know, we took it. It was a small deal, but, you know, we took it from like $50K a month to $300K a month and sold it 11 months later. You know, it was like, which was like just sort of weird. And I think candidly, when I tell that story, I want to make it abundantly clear that's like an outlier, that, you know, you don't normally 6x a business and sell it in less than a year. And especially since we did some pretty creative financing for the purchase of it. But yeah, I think 2020, after I sold something, after I sold something and started looking at buying things, it became like, oh, I've bought stuff before. I'm going to buy something again. Like, oh, what a clear and obvious thesis this was, you know what I mean, for me. So yeah.

I want to talk a little bit about TMO and the timeline. You mentioned you started in 2015. What was the first company there? Did you start it? Did you buy into it? And what was the structure? Because you had many different businesses there.

So Deemo was a really interesting deal. I got to give like a major shout out to my old business partner who's like just one of the most financially creative person people I've ever met my entire life. Like, I sort of— name is Jake. Um, he just has no audience. He hates being on the internet, so I don't talk about him very much. He's just like one of those much more quiet people. But, um, he had been a commodities trader. He was trading, uh, oil derivatives for a living. And I at the time was mentoring at Google Launchpad, this tech accelerator that Google runs. And I was like running social for a bunch of brands and had run off to Southeast Asia to sort of reinvent myself and eat, pray, love myself into a different version of me that I wanted to be. And came back to visit some friends in the States. I was in London at the time with Google and came back to visit some friends in the States and ran into Jake. And he was like, dude, you've been like, we knew each other as teens or early 20s. And he was like, since I saw you, like, You've been working with like McKinsey and Google, right? And I was like, yeah. He was like, okay, bro, I have the best idea. I started a blog about pot stocks. He'd started a Wix blog about cannabis equities, which in 2015 was obscenely, obscenely new, really nascent, really weird. There were like no US listings, maybe some ADRs on OTC markets, but like really Canadian entities, mostly up on the CSC and the TSX and TSXV. And we like sat down in a WeWork in what was, I think, 85 Broad, which was the old Goldman building, which is now has a WeWork in it or did have a WeWork at the time. And like took a conference room and he whiteboarded out for me like market cap and like the fungibility of shares and how this all worked and basically convinced me that cannabis was going to be the next big commodity and to sort of hop on board this little Wix blog that he had built and sunset everything I was doing, leave everything I was doing to go do this. And we wanted to initially— our plan, it's interesting how things pivot, but initially our plan was really to sort of want to build like the Cushing, Oklahoma of hemp and cannabis. So for context, right, like Cushing, Oklahoma is really where oil happens, right? Sort of they set the price of oil futures. And we thought that we could do this in Colorado and sort of like figure out like the really the price for CBD grams and THC grams, and we could then license it to the CMOE, CBOE, and CME. And we were going to get $0.10 a futures contract until the end of all time. This is sort of my— our big, big, big plan. Long story short, we end up building what became the largest financial news website in the cannabis sector, which was pretty niche, you know, doing 2 million uniques a month and you know, when we get to that size, and you're an industry that size, and no real bankers will touch it, you sort of become a really sort of large authority in that space. And so through that structure, we ended up building this weird holdco that I would not be able to design ever again, because we ended up doing lots of deals with public companies and these private companies raising capital. And we all of a sudden were like the home base for people raising capital and like doing roadshows with Cowen, you know, for CBD deals and doing these weird structures. And so I was very, very lucky. And I know I'm ranting now, but I was very lucky. Um, I went to 5 high schools and dropped out of college, so, you know, education was not my forte. But through, um, some of my parents' hard work, they sent me to some of the right schools in high school. And I went to school with a very nice guy, a friend of mine named Alex Gelband. And then I got a phone call when Jake and I started this company, which was, you know, DMO Holdings. I got a phone call from a gentleman named Tom Bell at Gellband and Company, an M&A-focused investment bank in Midtown Manhattan. And it was Alex's dad wanted to speak to me. Alex's dad owned an investment bank and he was like, hey, I'm really interested in what you guys are doing. I want to give you some money. Let's figure out how this works. And so I was very lucky from very, very early. I mean, he did a pretty great deal for himself. I took a bunch of venture debt, took a bunch of personal debt and gave up 30% of my company to this investment bank. But from very early, I had bunch of investment bankers in my ear on my, you know, meetings every week about like how we were taking equity from brands that we thought were going to blow up and how we were for ad dollars in lieu of ad dollars on our websites and our newsletter, et cetera, et cetera. And sort of got involved in some reverse mergers and sort of it just became this weird, again, like very, very non-traditional holdco, very non-traditional structure of growth. But what ended up happening was because of timing of public markets, you know, I'm not that smart, we sold this business in 2020. And anyone— July 2nd, 2020, that transaction closed. And anyone who knows anything about cannabis equities knows that we top ticked that really well. We timed the top of that and it was not on purpose, but we ended up with blocks of stock in a bunch of companies pre-going public that then we sort of helped make introductions for them to go public and ending up sort of having a treasury, so to speak, you know, these blocks of equity in these different companies and little SPVs that were larger than what we were doing in revenue. It was very weird. So anyway, it's a weird story and I sort of digress, but that's, I think we'll tell you a little bit about it. Hopefully it makes some sense. Yeah. So we, I mean, my background had always been like, it was like a hot term at the time. I would call myself a growth hacker. I think at my core now I'm really a strategist, but really what I was really good at acquiring customers through sort of organic means at a low cost. Right. That's really what I would say. So like we were just grinding, like we were just being hundreds of Facebook groups. We would create, we were making AI content before AI content really existed by using like Google Sheets and Google Finance API. We'd be pulling in, we may build these indices. So we built all these indices to then license to ETF providers. And sort of, we were building these indices, and then using the data inside those indices. So like, we would like go pull, we'd go put about, you know, together a basket of equities, a basket of stocks, and we'd say like, let's track what happens to them today. Right. And so then we would, it would reweight itself at the end of the day with Zapier to say like, oh, at the top, we're gonna put all the stocks that are green, that are above 5%, we'll pull all that information on them using Sheets and Zapier into a WordPress post. And then we would at the end just clean it up. So we would end up having hundreds of posts is my point, um, that were super hyper-focused on each stock. So Canopy Growth up 5% today, you know, on lower than average volume. This is a bullish indicator because blank, right? So my point is we would just do that at mass scale. And share that with like hundreds of very specific Facebook groups that are all interested in very specific equities. We'd be sharing them in StockTwits and subreddits. And so that was sort of our daily growth strategy. We became literally an aggregator. And then we built, you know, our newsletter, which was like 40,000+ people, was all super, super hyper-segmented out. So if you were interested in Canopy Growth specifically, or you wanted biotech cannabis-focused equity specifically, we just had you segmented out into all those completely different sections. So you would get a newsletter from us every single day that was hyper-focused on what you were actually interested in. Now, it's interesting because in 2024, this would be so much easier to do. At the time, it was like really clunky and weird and a lot of me and Jake showing up at the office at 5 AM and pulling press releases ourselves manually and making sure automations are working and doing all that. And then we just, you know, we ended up because a big thing was, you know, there weren't a bunch of players in the space. We became Google News approved. And so we were just in Google News. We would write an article about Aurora or Canopy, any of these sort of NYSE or NASDAQ listed ADRs eventually that existed from Canada. And we would just be on the top of Google for, you know, for if you search Canopy for 3 days straight. So we crushed SEO, we really crushed email, and we really crushed organic social in a weird way. And what you find about financial news is that bulls want to be bulls. So investors want to be bulls. So if I get 12,000 of you on a list about pot stocks and you're invested in pot stocks, you are hyper interested in sharing that news around as much as you can, right? There's like an inherent virality component, a K-factor I'd call it, that comes from being a shareholder and getting news that's good about your stock, right? You just— because you think the more that you share it around and show people, the, the more buyers will come into your stock. And the better you will do, right? And it actually is true, right? So it just becomes like this weird IR component into it. But that was really the crux of it at its core, you know. And then we built some other— we'd piggyback off that, right? So we'd have like— we ended up building some other financial news sites that were like predicated off of that, because if you're an investor in this, you're probably an investor in that. Crypto wasn't big at the time, but my lord, we probably at the time, if I'd had the same thing today, I would just go email all 40,000 people and say, are you interested in our main site? Was MJObserver.com, right? I'd say, you guys want to read CryptoObserver.com? Click here. And we'd probably have another 20,000 subs on that list again, and then be able to just crank the exact same business model. But yes, that's probably— took a few years to get to that size. You know, we capped out on traffic, I think, because we were the largest player in the industry. But also, you know, I wasn't really great at that time. I learned a lot about delegation and management and sort of structure through that process. And later on that, you know, we were just two kids, you know what I I mean, like just trying to figure it out. So I'm 36 in 2024, 2015, you know, 9 years ago. So I was 27. Jake was like 23, 22. So we were just sort of figuring it out.

So how was it team-wise? You mentioned delegation management. How quickly did you grow when it comes to employees? How quickly had to, you had to hire people? And because this is a very—

No, please, please go ahead. Sorry, continue.

Because this is a very niche industry? How did you find the right people from your blogs, newsletters, or how did it work?

So, great question. I'll say the one thing that's really interesting is that you will have, if you have a big audience, you just put out, I mean, we would get writers from our readers, right? People want to write, you know. We were paying, I mean, I was paying CFAs from Vanguard to write for us, you know, because they weren't writing about it at Vanguard. But, you know, they will happily take $100 an hour on the side to go write about a cannabis equity with some institutional-level research, you know what I mean? Like, um, and you'll see, you know, like, uh, so we end up having these really, really fantastic, fantastic writers. Also, Jake was just— I mean, he's just— I mean, I was the marketer, right? I mean, I wrote some stuff, but like, Jake was— had a big, um, following on Seeking Alpha already, which was a pretty big deal. Seeking Alpha is this sort of financial news financial analyst website. We did pretty well on Seeking Alpha as well, actually, when I think about it. That was where some of our traffic was coming from. And StockTwits, we were just crushing StockTwits, just hyper-focused content in StockTwits, which is like the Twitter for equities markets. I'll never forget this story I tell, and kudos to McKenna, who was like one of the first people that worked for us. She's amazing. And she literally just, she works in PR now for a firm, and she just won like best, like, conference PR of the year campaign. She did it for MAPS, which is like the psilocybin conference that was in Colorado, which is like very big now, which is obviously the next big wave is gonna be psilocybin. THC was a big one. But we had no idea we were doing— I didn't know what we were doing. The first day McKenna walked into that office, I'll never forget, we were at 90 Broad. We got a small little office across from WeWork you used to be in. First day McKenna walked in, and she worked in PR, and we figured we're gonna try and do some IR stuff. We need someone that knows how to use Meltwater, which is this tool, and knows how to like speak the PR pitch to people. Jake could speak to finance, I spoke to marketing, McKenna would speak the PR kind of stuff. And then we brought in this guy Mike who worked in sales. We had Rachel who was an analyst at a bank prior. But point is, is McKenna walked in, she's like, "Okay, what should I do?" And Jake and I looked at her and we were like, "I don't know. We figure it out every day. You can too." And it was like just a couple 26-year-olds that had no idea how to run a business or to hire people. This poor girl, she like stepped into this office and thinks, you know, she got a new job and we didn't tell her at all what to do. Through that process, we figured out sort of what to do and stuff. But it was like really, I never would want to run that business again because, you know, it had so many ups and downs. It was so much like, you know, one point we ran out of money essentially before we figured out really how to make money correctly and sort of had to let a bunch of people go and then bring people back. And I was, you know, living off $2,000 a month. In New York City, which is like just not possible, you know what I mean? Shout out to my ex-girlfriend who like worked in real estate private equity at the time, and I was like living in her studio with her. And like, so anyway, the, the high— I learned a lot about hiring and sort of setting up delegation and process to do that because I'd never really done that before, you know. I'd been plugged into some teams, you know, doing consulting work. I did some strategy work for Lionsgate and McKinsey and stuff, and would just be plugged into teams, but never sort of like, how do I hire from zero and teach someone something that I'm doing every day? So you learn a lot about like just documenting like everything step by step that you're doing. And it's still a process for me. My biggest, I'd say my biggest weakness these days is hiring and management. So it's really something I work on a ton, a ton these days.

And now still a little bit about the timeline. What about year 4 and 5? And when was the moment you decided or someone came to you and showed the interest of actually acquiring the whole group and how? How was the year 4, year 5?

So first of all, that transaction took like 6 months, which I think is like also an important thing for anyone who's not bought or sold a business is you think you just like sign a piece of paper and like, no, like 142 pages of merger docs and a couple hundred grand to lawyers later, you know what I mean? Like it was, and 6 months later we closed on that transaction. And it's one of those things like every moment you think it's going to be done, it's not done. Like every time you think that the docs are done, there's another lawyer has a different turn on the docs they need, right? Anyway, so actually really interesting story. We had turned down an acquisition earlier on, when we were in a really rough point, we had, we were about to do a round to raise some money. And we approached this large sort of cannabis publication that was very well known at the time, we approached the owner and said, hey, we'd love to have you be our lead and give us $500 grand. And he was like, What if I just bought your whole business from you? And we were like, well, maybe. What do you want to buy it for? And we negotiated to a lot more. We negotiated something that was a ridiculous amount more money than we should have gotten. Candidly, the idea was 90% of it in stock as well. So whatever, you know, with like weird clawbacks and covenants and earnouts and all this stuff. So, but I remember going home to my ex's house that night and thinking that I was going to walk, have like $3 million the next day.. And I said to her, I was like, this is it, baby. Like, I'm 28, like you're working, but don't worry. This is our first nest egg. You know, 2 years into this, we're good. You know? And I walked into the office the next day and there was a term sheet in my email for $2 million all in stock in a private company. I was like, oh my God, this is so not what we agreed to. But we, but we like really, we tore our hair out for like 2 days about it. You know what I mean? Because it was a huge deal. You know what I mean? It was a huge deal whether, you know, and we, and we turned it down and said no, and then ended up selling it for a lot more, obviously, years later. But, you know, I think it's interesting because when I take— I haven't thought about this until this moment— when I think about almost every transaction that I've done from an M&A standpoint, it's been with people that we were already working with, right? So it's been with people that I already had like a super strong rapport with. Actually, basically the company that bought us was a group that owned a company that was a client of ours, right? So they already knew what we were doing for them. And to be honest, we— they bought us for a higher multiple than anyone else would have because they just saw us as like an engine to do what we were already doing, you know what I mean, for, for their business, but at a lower cost internally and be able to do it in perpetuity. So yeah, we— that, that was probably like— the conversations probably started like a year out, I would guess. I don't know, but it really took 6 months. July 2nd is when it closed. I know that transaction closed because it was just the most meaningful thing that happened in my life. July 2nd, 2020. But that— it definitely took like— it was pre-pandemic, you know, before we were talking about it, because that was the year the pandemic— it was actually a really weird year for me because everyone felt the world was on fire and I just had the biggest financial windfall of my entire life, um, you know, in, uh, and I was like the middle of that summer was like in New York City in my backyard grilling up steaks, smoking cigars, you know what I mean? Um, and everyone thought the world was going to end. It was like the best financial year of my life.

How was, uh, the next 6 months or a year post-acquisition? Did you have like golden handcuffs, or how did this work?

It was weird. That's a great question. Bought a house, um, for— that was the first thing I did was I bought it that July. I bought an investment property. I thought I made some money, right? I made some, but not this sort of like what I would call FU money. It was not to do whatever you want for the rest of your life kind of money, right? You know, candidly, like I said, we got a, we actually, it's a much longer, I could do an hour on it fully because it's just, it was such a weird transaction, but like we actually got about $15 million with a bonus if we had hit certain KPIs in, in more stock in the parent that bought us. Right. So we've got some cash and a lot of stock. But some of it was actually— sorry, not to really overcomplicate it, we actually got all of it up front with 50% of it with a clawback they could take on it because we wanted— there's something called seasoning restrictions. And basically, this is where having the investment bank that owned a third of my company became really, really, really important to me. Because when you want to go sell public stock, you have the SEC makes you wait a certain amount of time. From issuance on those securities to sell them. So we wanted to be issued all of those securities up front, and if we didn't hit certain goals, then they could rip them back from us. But they would be starting seasoning all at the exact same time, right? So that we could start selling them at the same time. So, um, but it was really crazy. It was really interesting. I— because they owned a bunch of stuff, the guys that bought us, like, immediately I became an SVP of digital for a telemedicine company. Like I immediately had me doing something completely different. And telemedicine at the time in 2020 was like the hottest thing on the planet. Like you couldn't leave the house and you wanted to see the doctor, you know, that was the hottest thing on the planet. So I was like immediately started working on these asynchronous telemedicine funnels where basically you could be prescribed medicine through just a questionnaire and then a doctor would sign off on a script for you and this and that. But, you know, I tied up all my— I mean, without getting super into it, I tied up all my liquid cash in this house I bought, which was like the biggest mistake ever. God, that was like— and it became just a crazy nightmare. I basically thought I was going to buy this house and all of a sudden everything was going to come unrestricted and then I was going to refi the house. I'd convinced myself this was the path and actually helped me, really helped, I think, structure how I think a lot about buying businesses today because I bought this house and gut-rented the whole thing and I can't build IKEA furniture. You know, so like I ended up sort of what I thought was me 3 months of reno took almost a year and put me like an extra $160 grand in cash over budget. And just like I just locked up all my money. I all of a sudden went from having the biggest windfall in my life to being what I think a lot of entrepreneurs experience, which is like the biggest lesson was I was a paper millionaire with no cash, which is like a real trip because, and I don't even mean like in a liquid paper millionaire. I mean like liquid paper with restrictions on said securities. You know what I mean? Like, you know, Like, how was I getting loans for stuff? Because I had marketable securities, you know, that everyone knew that could be sold. But anyway, so it was really weird. Yeah, I mean, I spent like a year running, basically a year running digital for this telemedicine company and bought this house. I thought it was going to be the first of 100 rental properties I was going to buy and renovate, BRRRR as they call it, and refi. And Needless to say, a year later I sold that house and said, I never want to buy real estate again unless I'm an LP in a fund or unless I'm like, you know, buying 100-unit things. I actually had a friend say to me, it was like, listen, you've had to win now. You could just be an LP in a fund. You want to go put a few hundred grand in something, go put it in someone's funds that you trust more than you. Do not go buy single-family homes that need full construction on them. And I made $2,000 on that house in total. Took me almost a year and risked, you know, near half a million dollars. So it was like, you know, and, and I— and everyone's like, well, you made money in your first deal. And I was like, yeah. And they were like, that's, that's great. I was like, excuse my language, fuck this, you know what I mean? Like, you know, for everyone's hyped, I made $2,000 on a year of my time and, and hundreds of thousands of dollars in, in risk capital. And so I decided when it came to the businesses I want to look at buying, I wanted them to be things that I really understood buying and really understood that needed like that clear levers for growth. You know, I'm not the guy here looking at buying super distressed assets out of bankruptcy. You know, that's not, that's not what I'm interested in doing. I want to buy good homes that look ugly, that are on great blocks, right? They need new doors, new paint, you know, that like you can change the cap rate of if we're talking real estate. And so I think for me, What I've realized is that's my investment thesis is like, how do we buy things I have a competitive advantage with and that like don't need an obscene amount of, you know, that you can buy on light leverage and you just pay down cash flow. I mean, I think for me, the way I see doing $100 million, I'm 36, I want to, you know, the way I see doing $100 million by 46, $200 million by 46, just buying good businesses that have on very manageable leverage, you know, 40%, 30%, things like that, right? That I know that I have a competitive advantage because of my audience and my skill sets that we can sort of just increase, you know, I'm talking about 5% year-over-year growth, 3% year-over-year growth, right? Like, I'm not— I don't want to be the dude doing turnarounds. That's just not my— it's just not my bag, I don't think. Um, anyway, sorry, that was a bit of a rant, but hopefully that gives a bit of context.

No, no, all good, all good. We, uh, I want to ask, you can now pretty much repeat this success, hopefully, of what you learned from this 5-year journey. And if you show me a person and I'll share them a story on how you did it, everyone would like to go from 0 to 30, 31 million. So one lesson from this period is probably the importance of distribution.

Well, oh yeah.

Another is surfing on the right wave or being in the right boat. And, but what else? What are some lessons from this period of the real estate lesson we already learned, but when it comes to businesses and actually growing this?

Yeah, I think that like I, two things is that you really just touched them, but I'm going to sort of expand on them a little bit. One is that distribution is king. Like truly, truly, truly distribution is king. For example, I just bought a small business called OffMarket, like offmarket.so. It literally aggregates off-market deal flow and gives, you know, all the access for you to pitch the business owners on buying them. Well, I happen to run a newsletter for 16,000 people that are looking to buy businesses. I happen to have 120,000 followers that listen to me talk about buying businesses, right? So I clearly have obscene distribution for that business, right? It's not very hard for me to add $5,000, $10,000, $15,000 in MRR to that business. But I think from the DMO side is really what you touched on that I really like is sort of the nascent industry stuff, right? Is like the gray. I like playing in the gray. Like, I don't want to go do illegal stuff, but I'm definitely down to play in the places that the, well, I mean, I'm now, I'm full of gray hair, but the gray hair won't touch, so to speak, right? Like, and cannabis was that world for me, right? It really was. It was that, like, it was clear as day to me. I mean, I used to, I remember getting arguments because my girlfriend at the time worked at— for a company called Related, which is a huge, huge, huge real estate company in the States. They built Hudson Yards. It's $30 billion, the largest real estate project in the US, the largest low-income housing owner in New York. It's, um, uh, it's, uh, just a big, big company. The owner owns like a football team and all this different stuff. And she worked very close with the owners. And, um, so anyway, all our friends worked in banking and PE at the time. I remember talking to a bunch of kids who worked at BlackRock and they were talking about TAM of cannabis, right? How big cannabis was. And I was like, I think cannabis is as big as beer or bigger. And they were like, are you kidding me? No way. I was like, oh, like you don't even realize that cannabis already is as big as beer. It's just illegal. It's just in a black market, right? It's just no one knows it's there, right? So for me, the writing was on the wall. It wasn't like I— to go along with that, what you're both— those touch into it is like this idea of selling into latent demand. I really do not want to build demand for anything. I want to sell into latent demand. And so distribution, you have just the question is then what do they want to buy? So it's just about asking that audience what— sorry, I don't know, the thumbs up there, get, you know, um, giving them what they want to buy. And then from, for me, sort of playing on the edge in the, you know, you called it surfing the right wave, you know, I, I say all ships rise on high tide, right? It's just like we just want to be playing in spaces that are clearly growing and on the edge of it, right? And it's just like, can you time it correctly? That's what becomes tough with something like cannabis. It's still not federally legal. I mean, listen, I own, I own equities in cannabis that are down 80%, you know, right now. I just also believe in the long run that cannabis— I mean, I probably should sell them, but I also believe in the long run that cannabis will become federally legal in the United States. And then, then the game you'll be playing is like the commoditized pricing pressure game, because it's just going to be this commodity, you know. But nascent, gray— like, people early in crypto crushed it, people early in cannabis crushed it. If you ask me now, should I start a a weed investing website? I would say absolutely not. It'd be— what a terrible moment, you know. At 2015, it was the most perfect time to do it, you know. Um, obviously people are early on AI, right? But I think you don't have to be doing these like super cutting-edge risky things like that because they also get pretty saturated immediately with a bunch of weird bad actors. But in general, it's like selling into latent demand, right? Where is there already a market? What are people going to want to buy? And then for me, the big lesson I think going from that is like, I'm not a disruptor, I'm not a game changer, I'm not Mark Zuckerberg, I'm not Elon Musk, I'm not Jeff Bezos. I will never be those people. And that is totally okay. And if that is you, kudos, good luck. You know, you want to go build the $100 billion business, go for it. I think that my takeaway from— I wouldn't say getting lucky, but getting lucky in timing with some of these things. Was that from here on out, I'm just trying to hit base hits, right? It's like I've had a win or two that sort of gave me a little nest egg that proved to people that I'm worth giving their money to. I'm worth trusting as a steward of capital. And now I just want to hit, you know, singles, doubles, triples in a very American baseball analogy, right? You know, I'm not worried about hitting a grand slam. If you're 22, you can go for a grand slam. At 36, that's not the way I see building another $100 million.

Before talking about off-market That is so. What about the Blue Angels? What's the story behind this? And I mean, growing a business from $50K a month to $300K and then selling it again, if you could do that again and again and again.

Definitely would do that again and again and again if we could, right? I think, okay, so I'll tell you that story. But I think what's really interesting about that is that like, When I tell you my thesis now, it's not that I wouldn't take— like, off-market is one of those distressed deals. It's tiny, but I would take a distressed deal that's very clear to me I have an obscene advantage in. But in general, we're deploying capital, it's much more deploying sort of safer bets. So Blue Angels. Blue Angels was a really interesting deal in, I guess, '21, a year after I sold DMO. I was like looking— I wanted to start an aggregator. I was like going to roll up you know, I skipped some of this DMO story, but some of it ended up owning equity in some consumer packaged goods brands that were in the CBD space that I ended up running digital for, basically like as a fractional CMO. Um, and that my world is marketing, right? And so, um, especially during COVID the world was shut down, direct-to-consumer was really flying, right? Like everyone on the planet wanted to allocate capital to online businesses and only D2C. And so I was doing some consulting for a guy named Peter, again, also a better entrepreneur than I. It's crazy, there's some of the people I've worked with and that have hired me are just like better than me, and I don't— I'm always blown away that they want to hire me, and it works out for all of us, but it's very interesting. Peter was a better bootstrapped entrepreneur than I was for sure, and he had taken— he had built a couple things before. Um, uh, he sold another thing called Blue Tees Golf, which was actually doing really well now, and then I tried to buy a couple years ago. But he started this direct-to-consumer hearing aid company and I was helping them. He couldn't break past like 30, 40 grand a month. And he hired me just as a consultant to like help them look at their funnels and their pricing and figure it all out. And I at the time had this thesis of having a holdco. It was really an aggregator trying to aggregate brands. Thrashio had just started. They'd raised a bunch of money. They were buying FBA brands. Now they're bankrupt. There was other aggre— everyone in the world that played in my space wanted to have an aggregator buying DTC brands. So I went and I, and I started a company called Common Commerce, and I went and I got some friends to join the board who were better operators than me. One of them was at the time, you know, I had a CFO and the COO of a big apparel brand like that was doing $2 billion a year on my board. And so that lended a lot of credibility to us. And I just figured, you know, we're just going to go around and you want to take debt, you know, go tell everyone that your board is runs a $2 billion a year P&L, and all of a sudden they're much more interested in giving you money. You know, everyone's much more interested in trusting you. So they knew me and trusted me. So I got them to join our board and they had a little bit of fiduciary obligation, et cetera, et cetera. And I saw an opportunity with Blue Angels Hearing. It just seemed like I saw this business. I was helping them grow a little bit here and there. And I thought this could be the linchpin. This could be like the centerpiece for us. This could be the first acquisition that we made. At the time I was due diligence in a bunch of different other businesses. One was a company called Cloudy. It was a melatonin vaporizer. It won, you know, $9 million for essentially $8.2 if they're going to go to market at $9 through a broker and they were going to sell to me for $8.2. I was talking to all these mezz debt lenders about me taking $6 million in PG debt on a 36-month note at the time, which was like 11.9% with warrants. And I was just like, not ready. I was like, I am not about to go PG $6 million. On, you know, something that I think is— I, on a 10-year term, yeah, I'll pay it down, but in 36, just seems— 36 months seems scary. And, you know, I had my friend who was working— had worked in PE at the time, who was on the board, who was like, dude, just take the debt, we'll refinance the debt. Debt is a refinance game, that's literally how this works. Freaked me out. Anyway, so I convinced Peter, who is amazing, who the owner of Blue Angels Hearing, to come on board and basically sell us 10% of the business upfront and roll in the other 90% in equity into the parent. And obviously, as you know, as many listeners know, there's plenty of ways you can structure this. You know, he had an outsized, in the moment, majority of commons in the parent because that's how the rolling of his equity in worked into that deal. I had different share classes, et cetera, et cetera. And what we did really interestingly was give him clawback provisions or unwind provisions, sorry, that if we didn't hit certain KPIs, since he was the first one to do it, that he could undo the whole deal. And he would still— I would still own our 10%, but he would not be part of our parent company doing this roll-up. And the first thing we did was just change the pricing of the products. And it— we all of a sudden, all the ad campaigns became super profitable. Yeah, we just grew and grew and grew. And Peter actually stayed on board as CEO, which is really exciting and interesting for me. Because I got to, first time in my life, I really got to work on a business as opposed to fully in the business. And that really opened my eyes to something. I mean, I was still working on it a few hours a week. I was still in Slack running meetings and stuff, you know, but like Peter really ran that business as a CEO and used me and the board sort of as advisors. And then, yeah, a few months later, we got reached out to by Open Store, which was, is Keith Raboi, you know, PayPal Mafia, his aggregator out of Miami. And we were there and, you know, they promised a 30-day close. They were awesome, but clearly it was not a 30-day close. It's almost impossible to really close in 30 days on a real acquisition, but they were fast and they grinded and they worked really hard. And yeah, we were their first acquisition. After that, it was like, whoa, this is such an easy win. I started looking for the next acquisition, but decided, sort of saw the writing on the wall. I got lucky again to just watch the writing on the wall with some of these other aggregators where it didn't, the crushing of OpEx was not going to work in the way that we wanted it to at that size. And that was the real problem most aggregators in this space, right, was that we were all playing in this like sub-million-dollar EBITDA businesses, right? Well, the problem is so much OpEx has to get eaten up by an operator at that size. And to have a really good op— you know, you do $300K in EBITDA— forget EBITDA, it's not really what you— SDE, seller discretionary earnings, right? Like $30K. Well, anyone who's really good at running that business should probably own the whole business at $300K, or we're going to take $0 off of it. Because they're going to pay them all $300 grand, right? And so, and they're— and once you start taking— once you remove a really good operator from that business, they're pretty fickle, right? They're not— you know, it's not— ironically, the larger— either you buy something— from what I've seen, what really works well is people buying these tiny little side hustles. You want to buy a blog for $50 grand and work a couple hours a week blogging, that's not rocket science. I can help anyone do that. Or you want to buy something big enough that, like, you can actually put a great operator in place and really, really run it. So I, this year, yeah, was talking to an independent sponsor, basically. I won't mention them, but who they were, but they're well known in my world. And the idea was I was going to put up $100,000 or $200,000 and they were going to put up, you know, $2 to $4 million and we were going to go buy a business. 2 months into me doing this, I was just like, this is not going to make sense at $2 million again for what I want to do. I'm just going to buy a job essentially. And I realized that I wanted to go buy bigger things and be able to work on the businesses as opposed to in the businesses. And buy big enough things that you could actually take some leverage on them. It didn't have to just be this, like, you know, an SBA loan or something. But anyway, I'm digressing now away from the question. I don't even know if I answered your question. Sorry, I'm just terrible at that. No, no, hopefully I give you some context.

It's all good. So what about your view now? I mean, I'm a big believer that we have 5, 6 shots in life when it comes to building a business or— Interesting. Being an entrepreneur, each bullet could be 3 years, 5 years. So your one bullet was DMO, it was 5 years. Another one was the one you just sold to Open Store, it was 11 months.

Yep.

Yeah.

That's a great way to think of it. A couple of bullets. Yeah. That's crazy. What am I going to do with the rest of the bullets?

Yes. And what is your thought of finding a good business, growing it, and as, for example, it produces great cash flow, not selling it, because then you're again back on step one of trying to find this business. How are your thoughts around this?

Great question. I think that for people listening, I don't believe that you can become an entrepreneur. This is going to sound weird and cheesy. I don't believe that you can become an entrepreneur. I think it's a mindset and a frame that you have in your brain. What I think though is you can unlock being an entrepreneur if you're not already one, right? So I think there's tons of of hypothetically fantastic entrepreneurs that should be doing an independent sponsor or search fund model or be using their own cash or buying small deals, and they're just like stuck in their job that they hate. That I think exists all the time. I think there are better entrepreneurs than me that are just sitting at a VP level of a bank right now and will do that forever because they don't see the path to how to get there. But I find that it's very tough for me to convince people that don't already— their brain doesn't work a certain way— to fully rewire how their brain works. So in terms of shots, I think that right now I'm 36, I'm single. I mean, I have a girlfriend, but like we're not married and there's no like sort of lifestyle creep is real. What I'll say is that, so what I mean is like I used to be able to live off 2 or 3 grand a month. You know, I drive a nice car and live in a nice apartment now in LA and often try and be bicoastal. My lifestyle costs have gone up immensely. So what I mean is that my next shot out of the gun, so to speak, I think I've got my one last full risk shot in me. Right. What I mean by that is like, I'm happy to cut my lifestyle down a little bit. I'm not going to go sleep on an air mattress again like I have before. That's— I'm not— no interest in that. But I know that like the next— this stage of my life, like the next 5 years, probably includes marriage and a child. And so that like some of that swing taking has to change a little bit because you're worried about people other than yourself. So I think that's probably my next shot is probably a bit more on capital allocation. So to speak, because I just think that's probably the next thing in my career that makes sense. Probably I'll syndicate some deals next year in 2025. I don't have a PE background, so no one's going to write me a $100 million blank check and let me manage a fund on a 2 and 20. But I think if I bring people the right deal, they're happy to give me 20, um, if that makes sense. So that's my next shot. And then I think on selling or not selling, this is a great question because the newsletter I run is called Nano Flips, and it was all the idea was about flipping businesses. What I think is that every business has its exit, whether you like it or not. Always. Dutch East India Company doesn't exist anymore. You know what I mean? Like, one day Apple will not exist. I'm 100% sure of that. How you get that exit is totally dependent on you. I have found, along your line of 5 shots, that my— I'm not sure I want to do anything more than 10 years straight. So that's just how my brain works. So for me, a holdco GP vehicle works for that thesis because either way, it's— I'm constantly every couple years probably getting something new and exciting in the, in the pipeline anyway. So that fits for me. But I think I love— I know some guys like Sieva, I know some guys that run permanent equity sort of holdcos, so to speak. And I think it's really interesting, the idea of holding something forever. I mean, here's the real answer for that. When I talk to entrepreneurs, my girlfriend has a business, for example, they're doing good money this year, they'll be their first 7-figure year. And everyone, when you do that, all of a sudden you have your, your eyes open up to $100 million exit. Everyone thinks they want to sell their business for $100 million. Well, I, the lesson I learned last year really was that not every business scales. So what I mean by that is there, it's not rocket science to get to a million, $2 million bucks, $3 million bucks a year. I think even $5 to $10 can be done in most models, right? An agency, a laundromat, anything. You can get to $5 to $10 million bucks a year. Once you start making real cash flow, And I don't mean just like owner-operator, I make $300,000 or $400,000 a year and it pays my bills and I have a nice life. I mean, like, you're taking home $2 million in distributions a year. You start to enter a zone in which, why would I sell this business? Right? I think you really, you know, everyone thinks they want an exit. But the thing is, when you have enough money, liquidity events are just a function of trying to reallocate capital into something new. Right? If I have enough money, why do I need liquidity except unless I see a better opportunity? So if I own a business that hypothetically you've taken to, either you love running, it makes you a million, two buck, or $2 million a year, or you're very removed from and makes you a million or $2 million a year. Let's say I make a million dollars a year from a business. Would I take $5 million? I start to really— and, and it's something I love doing, like I enjoy, I'm good at, Or I'm fully removed from and I just get a million in distributions and dividends every year. I don't know. It means I got to go find something else that I believe in more that's going to return me more than 20% year over year. You know what I mean? Like, because it's— I'm getting 20% on a $5 million valuation if I'm taking a million out every year, right? So, um, and that's not including growth of the business. That's just like dividends of business distributions from it. So I think my point to answer your question is if you like what you're doing, run it, keep doing it. Because this, for me, like, that's what this is all about, right? I just think, uh, that often— and this is a lot of PE thesis— often people look at a business and think somebody else can take it further. And sometimes there are inefficiencies in businesses that I cannot fix. You know, we talk about real EBITDA. Everyone throws around the term EBITDA. So much of those letters are not used really. But like You know, I don't happen to be— I'm not re-domiciling businesses for tax purposes, right? I'm not, you know, amortizing. My point is, there are people above my pay grade that look at how to do this in ways that I don't currently. And so I think the same thing for searchers and smaller funds and family offices is that, like, you know, owner-operators often don't know how to do things that you might be able to do. So I think holding things forever is amazing if you can. I just, I do believe that every business has its exit. At some point it's going to go out of business or someone's going to buy it or something, who knows. So if you see an opportunity, like, I'm— the big lesson I learned in the past couple years is the macro affects the micro. And so like, I, I now LARP as a macroeconomist, as everyone does on Twitter at least, you know. But like, I really pay attention to things like rate cuts and cycles, right? Because I think if you can time— if you can be a little more patient, then like, and you can time cycles and you can really think about when are risk-on versus risk-off environments that there's probably a good multiple arbitrage to play in buying and selling this exact same business without any change in profitability, just between the timing of rate cuts. You know what I mean? Like in a low rate environment, you're probably going to get a higher multiple on it than in a high rate environment. So anyway, that's, that's, again, I digress as always, but hopefully they answer some of it.

So you now own this website offmarket.so. You get a lot of deal flow from there. Have you started looking at those larger businesses? You mentioned $20 million, for example. Compared to the smaller ones, $5 million and smaller, where you oftentimes buy yourself a job compared to larger ones where there is a management in place. So have you seen those larger deals or how has it been so far? What type of deals this off-market website brings to you?

So off-market, really the way it works is basically we just aggregate and organize all these internet businesses across like Shopify apps to Shopify stores to FBA brand, all these, right? And then we aggregate it all together and we make it in an organized way. So you could say like, I'm looking to buy a Shopify app that is, has over 5 stars, that's in the conversion rate optimization niche that is growing 60% year over year, right? And so we'll pull that for you. And then we, we then take all the data to pull the contact information and enrich it so you can reach out, right? And so then obviously the next thing that we do is if you want us to reach out for you, if you're a searcher, you probably want to reach out yourself. You're a PE shop, you know, you are very happy to pay us a few thousand dollars a month to sort of book calls on your calendar with business sellers, right? People that want to sell their business. So what I will tell you is that a lot of the advisory that I've done over the past couple of years, and it's really what I've done for the past year or two, it's just like helping people buy businesses and is mostly been on-market deals, right? So things that are for sale through brokers and marketplaces. The best deals I've ever gotten are all off-market. Almost every transaction I do these days is completely through something that is like word of mouth or a friend. I don't work in real estate, but I have friends who work in commercial real estate who will tell you that if by the time it gets to LoopNet, they've all looked at that deal and they don't want it. I mean, so the time it gets to a place where everyone can see it, they've already looked at that deal. So to answer your question about how do you find a $20 million deal, I really believe that I'm lucky enough to have a competitive advantage, and that competitive advantage is my audience. And that people get their competitive advantage from different places, right? Some people do it by door knocking in real estate, whatever it is. You know, for me, it's audience. For me, it's that I have— I am a— I wouldn't call myself an influencer, but I would say that I'm a a well-known person in this space, right? I have 82,000 followers on Twitter, 6,000 IG, 6,000 on LinkedIn, 25,000 on TikTok, and I just talk about growing, uh, and marketing internet-based businesses and buying and selling them. And so I get deal flow. I get people that DM me, hey, I kind of want to sell this business. I get people that are saying, hey, I need help with this business. So sadly, I wish I could package that up for everyone, and I cannot, you know. So the best thing I can do is be like, Hey, you know, here's this, you know, for $100 a month, for less than $100 a month, I'm going to give you access to the organized data of these businesses, and you can reach out to them and you can pitch 100 of them and you'll get 10 of them on a call and you'll close on one, right? Um, but so for me, what I can tell you is that everyone I know that works in this space, and that's the reason that, you know, not to sound lewd, but the thing that gets PE shops hard is proprietary deal flow, right? Is everyone wants proprietary deal flow. Everyone wants deals that no one else has access to. Because it opens up your negotiation abilities and opens up sort of everything. And so for me, my proprietary deal flow comes from my audience. And so the other part that comes from proprietary deal flow and comes from finding these deals is that you'll realize that if someone owns a good business— if someone owns a shitty business, they'll sell to anyone and they just want as much money as possible. If somebody owns a good business and you talk about rolling in equity, you talk about earnouts, you talk about any of these levers that you can pull to close valuation gaps, They are infinitely more likely to do that with someone that they feel like they know and they trust, right? And so because of the audience, I happen to have relationships with people where they feel like they know and they trust me. Now, before we started recording this podcast, you literally said, I've been listening, I listened to some podcasts you were on and I feel like I know you already, right? So you and I are just more likely to go through a deal together than someone that you've never spoken to before, right? Or you've never had that opportunity to interface with. So what I'll say, and I say this to everyone, is I wish I could quantify it more. When you start looking at deals, the best thing, if you want to buy a business, the first thing you need to be doing is letting people know that you want to buy a business and just talking to other business owners and sort of seeing what's out there.

So do you still believe, or how has been the reality when it comes to those larger businesses? Are those large? I mean, there's obviously a lot of people following who want to be entrepreneurs, maybe doing their first deal. Then there are some bigger so-called whales who do very big things. How has it been for you when it comes to those $20 million type businesses?

I mean, you find in my, like for Twitter, for example, there's, I know tons of people are doing, you know, that are doing $3 or $4 million in EBITDA, you know, that are, that have a $10 to $20 million business for sure. And it's just about, do you have a rapport with them? You know, I have a friend, I'm not going to say his company, But we wanted to— they do like $90 million a year and they did about $8.5 million in EBITDA last year. They're down a little bit. We did some overpurchasing post-COVID, as many people did in the direct-to-consumer space because they thought they were going to keep growing at that rate. Anyway, it doesn't matter. He really only owns about 30% of the business. He's the CEO and owns about 30%. A holdco owns the other 70%. They own a bunch of stuff. We wanted to buy his business. He came to me and was like, dude, I want to buy out my partners. Now, part of the conversation later on was him telling me, oh, by the way, when you do revenue like that, investment bankers call you all the time asking if you want to sell your business or raise capital. He's already got people taking him to Lakers games asking him if he wants to sell his business or try and buy out the partners. They came to me, right? Now, candidly, his partners did not want to roll in any equity and they wanted a 10x EBITDA multiple on this business. And so no one wants to write a $100 million check for a business doing $8.5 million in EBITDA that's not growing super, super fast. But it was a reminder to me that I do have access to things that other people do not. And that is proprietary deal flow. And even though he's getting taken to Lakers games by investment banks, he and I are the ones going to dinner. And he's like, how do we structure this? How do we make this happen so that I can get the most out of it? How do you know what I mean? So, and I think the other thing that really helps me with structuring deals and talking about deals with people is I'm not a banker, I'm an operator. Right? So it's very easy for me to look at someone and be like, listen, dude, this funnel does this. I would try this content. I would do that. A, just creates rapport. But also if we're talking about, again, creative deal structure, anyone rolling in equity into anything, you are much more likely to give me your business if you believe that I'm going to be a great steward of this business. And especially if you're going to retain some equity in it, then to some, because I've watched bankers run businesses to the ground or they rip them apart and sell them for parts, right? That's very classic PE model stuff. Right. So I think that's my sort of— again, do I think that works for me? Am I competing with Apollo? No. You know what I mean? Like, you know, that's just not the world for me. I think the world that the sweet spot for me is that sort of how do we get $2 to $5 million EBITDA businesses? There's enough cash flow on them for me to go hire an amazing operator that I trust, say, go leave your job. I'm going to pay you $300,000 a year, give you a little bit of, you know, bonus on certain things. And we're making enough money that we're going to crush these hurdles for investors and just do well there. And then you just look for, you know, businesses that don't— I'm not trying to 10x these businesses. We're talking about paying down the note and small growth, you know, like over, over the next 5 to 10 years. You do that with 5 companies over the next decade, and all of a sudden you have $100 million, right? And my holdco is retaining $25 or $30 million of it and taking on, you know, taking 10 million distributions off it every year.

You know, I have a few very important questions, topics I would like to discuss. Do you still have a few minutes?

Yeah, yeah, dude, this— yeah, we're good to go.

Let's chat. Again, coming back to distribution is everything. You, you talk so much about the audience. I want to cover short-form content, long-form content, and I would like to add there how ego is holding people back and how you As I know you said this on a previous podcast, that you don't care. You just do your stuff. You're creative. You're doing those catchy videos. And this is the secret because no one wants to do this because they have this big ego. What are your thoughts on this?

I love that you brought that up because I'm constantly— like I was telling my girlfriend's business partner the other day that she needs to be on video more, right? Like she's just like, oh, it's so cringy. Get cringy. Let's get cringy. Because here's the reality. And by the way, I do care. I just swallow my pride down and try and be cool about it, you know. Um, but this kind of goes back to the first— one of the first things we spoke about was the lesson about distribution and then riding the right wave. So I can tell you is that the right wave now is what other people— if it feels like it's cheesy, then get cheesy, right? Because what that means is 9 out of 10 of your competitors are not going to touch it. They're not. Dude, you and I play in a very similar world, almost the exact same world. And you and I are out here making podcasts and making content, and it probably opens up doors. But here's the reality. Most of the other guys I know with gray hair will not hop on this stuff, will not do it, because they think it's cringy. And that's okay. Let them not hop on it. I would love you to be afraid. I would love your ego to be so much of your enemy that it stops you from getting the same access to deals and the same distribution that I get. Please. Not you, but, you know, who my competition, right? And so I think that at 36, I'm blessed. Two of my best friends, Oren and Colin, have big audiences, and they do— you know, when I first met them, they were running a pubco doing about $100 million a year. You know, they both are just killers, like, amazing entrepreneurs, and they have much bigger audiences than me. They're always— I'm very blessed to be in a group chat with them where they bully me every day to try and make content. And You know, I think Colin's 37, Warren's 38, I'm 36. And I think we've all realized that we have this very beautiful sweet spot where like I can go speak to everyone who's 50 and 60 and they all take me very seriously. But I also recognize that like that the world is changing into a content-focused one. And what— where I'll go with that is that I think I had an epiphany. The only reason I've recently— I sort of stopped a lot of this content stuff for a while and I'd stopped doing my newsletter and stopped doing these workshops where we help people buy businesses. Decided to pick it up, back up again because I had an epiphany because I was in my own head every day saying, oh, do you know how many people will not give me capital anymore because they see me doing this and they think it's cheesy? Well, the other thing I realized was that for every person that says that's cheesy, I don't want to give James money or do deals with him, there's another person that's like, oh, this guy gets it. This guy really gets it. And I really want to give him my money. Right. And so, and in fact, there's two people You know, one is the guy who says like, whoa, he really gets it. And I love that he understands the future of distribution and the future of audience. And then someone else who just never knew about me until the distribution of the audience. You know what I mean? Like I have on Twitter, like 100-some-odd people, like in a private list that are just capital. I know of like, we touched on this before the call even, but like I can name without even like trying really hard, like $50 billion in AUM that follows me. It like reads stuff that I say. You know, and while everyone else is cold emailing VCs, I can just send a DM to someone that like already knows and trusts me and loves me. Right. And so I think that's like super powerful. And I think that like what's happened is that everyone thinks about audience as like people dancing on TikTok still. And so that really means that you just have this huge opportunity to go be a professional and be an adult and maybe a little cringy, fine. You know what I mean? Like, but in the short-form video world and written world as well, you know, I think, for example, I put a little tweet out yesterday or two days ago that I just wholeheartedly know is true. You know, my audience is not the audience that wants to make $10 grand a month. In fact, if you're looking to make $10,000 a month, you know, from nothing and you can't afford your bills, I'm not the guy to talk to, right? Like, you want to go buy a business, I'm the guy to talk to, but you should probably already have your 401 maxed out and be making good money and be stable. But I know anyone that wants to either grow a business they bought or start from scratch in services, I promise you, promise you, promise you, if you want to add $10,000 a month in MRR to this business, and let's say a company sells for, just to make the math easy, like a 3x on net profits, right? So 30— so for every dollar you add, you're adding $36 in enterprise value to this business. So $10,000, that's $360,000 in value to this business, hypothetically. Obviously there's margins you got to account for, but if you went— let's say you bought a services business, you're already a copywriter. I'm just making this up, Tom, and you're a copywriter and you bought a copywriting business. You wanted to add $10K a month to it. If you literally went and spent a week going through all the viral TikToks and Instagram Reels of people in another services industry that have gone viral, and you aggregated all of them, and then you took the top 90 of them, and then you just went through and changed the copy to be talking about your business and what you are an expert in, you already know, and what the services you offer is, and you posted one a day, on every single channel, LinkedIn, X, YouTube Shorts, all of it, I promise you that you could, you could gather an aggregate across all of them of 500 followers a month. I'm positive of it. You're talking about 4 or 5 channels. That's, you know, 15 followers a day across the 5. That's 2 or 3 followers a day across all channels on each one. Unequivocally be possible. In fact, I think if you really did it for 30 days, you'd crush those numbers. 500 followers a month if every single person that came in you DM them and said, hey, are you here for free content or are you interested in some services? And someone said, I'm here for free content. Boom, excellent. Send them a 5 or 10-minute YouTube video that you've made about your services. They teach them a free lesson. At the end of it, tell them, book a call if you want more. Oh, they're here for services? Excellent, let's hop on a call and chat. I'm just positive that you could add, you know, 5 or 10 grand in a month in MRR by just doing that. Now you could do that by either just a business you're starting on your own or to one you buy. I'm positive of it. And that's me being very conservative. So my point is, is that because everyone thinks about short-form content as people dancing on TikTok, there still is opportunity for you to do that in the professional business side because it's not just, there's no glut of it. The competition is so much lower. The moment that you see 100,000 different accountants making accounting content, and by the way, it doesn't matter. It would still work if there was 100,000 of them. But that's when the moment becomes harder. But now I'm trying to ride the right wave. And I think that everyone can. I think there's an opportunity for the next 5 or 10 years. As long as all the money is still held by people that are old enough that they think this is cringy and stupid, that wave will exist. Because the reality is, is that by the time Gen Z are boomers age, this will be the norm. It will be insane that the idea that a business does not do short-form content. So you got 10 or 20 years of this already. We're looking at the silver tsunami. You're going to watch all the boomers in America die and hand off businesses. And all of a sudden millennials are going to have more wealth than ever. Okay, well then the next 20 years you got this ability to still be that person creating content while the people that hold money, the people that really hold wealth still are afraid to do so. Beautiful.

I just wanted to ask what would be your final advice for investors, LPs, GPs, family offices? I wouldn't say it's not to do short form. But how I think this is just putting yourself out there, sharing your thoughts, documenting your journey. That's what I've been trying to do.

Yeah. I mean, Twitter is what changed the world for me, by the way. You know, Twitter is the easiest. I mean, sadly, I think that the algorithm on Twitter has changed drastically. I used to do 5,000 followers a month like nothing. And I actually love Elon. I'm a pretty big fan of Elon. I know people aren't, but when he bought it, the algo changed and everything changed for that platform, right? But, you know, if video is not where you want to be, that's fine. There's written platforms, there's Medium, there's Twitter, there's LinkedIn, there's Substack. I think putting— I think, by the way, when you have— listen, I think that for me, for example, I want to go raise some money, right? It's a— and it's the first time I'm going to raise money in years, partially because I really feel a massive obligation. I think I'm very jealous of those who can raise money and just not even worry about it. When I raise money, it feels like the most pressure I've ever had in my life on my shoulders, right? And so for me though, I think because my audience, I'm not gonna have a particularly hard time raising capital. So I think for the first time, instead of me knocking on 20 doors and telling people, hey, I've got $10,000 allocated for you, will you please buy this, that, you know, I think all of a sudden if I put out an email, I put out a tweet, and I email some people, we're gonna have— I'm gonna have 100 calls lined up. And I don't think I have a hard time getting some capital. But I'm really interested, and I can actually say this for real, for the first time in life, in getting the right capital. Right? So if you're an LP, right, if you're an investor, I think it's worth having a good, you know, rapport with the people, because the right deals— you know this world, I know this world— there's no shortage of money out there. The shortage is good deals, right? So if you're an LP and you've got capital, when you get access to those good deals, you want to be able to be someone that someone wants to take your money. You know, if I were raising $100 million, I might have a hard time and be start asking everyone for money. You know, me raising a couple million bucks to seed this idea I have, You know, I want to be from the right people that I trust. I know they trust me and that they can also be follow-on for more capital and help me with distribution, right? So my point is, if you're an LP, if you're an investor, I would think it's really important to build rapports with people that have the distribution. If you don't have that distribution, go start building it with the people that do, because we do have a competitive advantage. And it's not just a competitive advantage for buying businesses, it's a competitive advantage for raising capital as well and the growth of those businesses. So Hopefully that's a useful little bit.

Perfect. Okay, James, let's wrap up with the famous 5. I already know. How old are you? What is your favorite book?

This is going to be like a cheesy one. I'm like looking around to double check in my office because there's like— I think probably The Alchemist was the most impactful book I've ever read. And I hate saying because everyone's— I mean, there's other great books I've read, but The Alchemist was the only book that made me bawl crying. And I was on a plane. I'll never forget. It's a short read. For anyone who's not read The Alchemist, I read it on a plane from front cover to back cover. And it was just a very serendipitous time in my life to read it. And it's going to sound so cheesy, but it was because I had made some money and I had made more money, not like that crazy do whatever you want money, but I had the first time was like, I don't have to work for a few years if I don't want to. And was dating the people I wanted. I just bought a new car. I got this duplex that I love living in in LA and was bicoastal. I had an apartment in New York, apartment in LA.. And I was one of the saddest I've ever been in my entire life. It sounds really cheesy, but I was one of the most depressed I'd ever been in my entire life. It's because I had no direction to run in. I had no goals. I had no nothing. And the idea of The Alchemist, without giving away the book, is everything this young man has been searching for his entire life was actually in his hometown. It was in him, right? Everything that he's been chasing the whole time was there the whole time while he was chasing it. And there's a lyric from a song I like that says, like, you know, we should be dancing with fire when we're really just chasing the sun. And that sort of touches on this idea as well, is that you should be able to find some of this happiness and joy within yourself because chasing it from external means is really not it, right? And so, it was just apropos of my life at that moment where I recognized like, "Whoa, all of a sudden I had the house I wanted, I had the car I wanted, I had the money I wanted and I wasn't happy." And so, that I should probably start trying to find some happiness and fulfillment from not these external things I've been chasing and now I had, but from what was in me. So the Alchemist. Sorry, that's a long answer.

Oh, all good. What's the best investment advice you've ever got?

If it looks too good to be true, it is too good to be true. It's just, it's so, so, so simple. But I think that if we're talking about business buying, and my world, which I do a lot of advisory on, is sub-$5 million, you're going to find a lot of people selling you hopes and dreams that are not real. And so the other one I would give that came from a friend/mentor of mine, it was really good investment advice. I started writing checks, venture checks into companies when I sold my company. I mean, you know, small checks, $25,000, $50,000 things here, there, and other deals. I took a friend of mine aside who had built a very big company and sold it. We were talking about it and he goes, you're not rich enough to be writing those checks, bro. I was like, what do you mean? $50,000? I got $50,000. He's like, no, no, you're just so— you're writing checks that are based on 1 in 1,000 theses, hoping that 1 in 5 hits. And that's just really not the way to do it. He's like, you're not at a place where you can be writing $25K, $50K checks. Now don't get me wrong, I think because the checks I wrote were in— because of my distribution moat and competitive advantage I have, I got into rounds of companies that on paper at least— there's no liquidity events for me yet, but on paper I'm up, you know, 3, 4x, and I think are going to be winners because I just plan this little circle of friends who know each other. I know they're raising, I know what they're doing. I find that everyone who's got a couple hundred grand wants to be an angel investor, and the truth is it's like, I mean, yeah, if you think it's fun and you want to write a $5K check so you can tell someone that you did, amazing. But in general, writing $50,000 checks, $100,000 checks, it should be a tiny blip of your net worth to write that kind of money into someone, or you should be heavily involved or know that you can make a massive difference into that business. So yeah, I think to sum it up was like writing angel checks or writing venture-style checks without having a venture-style war chest is a very dangerous game. And you're most likely going to lose all of your money that way.

And last one, I'm sure people would like to reach out. So where can they find you?

On Twitter, I'm Jameson Camp. On Instagram, I'm The James Camp. Hi@nanoflips.com. Nanoflips.com is my newsletter. It's sort of my personal newsletter. I write about deals and just random stuff in my life, I guess. But really, we— that's really the best way to do it. I actually still read— that's 16,000 subscribers. I read every email that comes into it still. So yeah, hi@nanoflips.com. And then Twitter is Jameson Camp. Instagram, The James Camp. And yeah, I don't know, I'm all over, you know. Hopefully, hopefully they find me somewhere.

Awesome. Thanks again for your time, and thanks a lot for doing this, Chip.

Yeah, thanks so much for having me, man. I could obviously talk about this for hours and hours on end, so I appreciate it.