John Lee Dumas On How He Saved $1,000,000 In Taxes By Moving To Puerto Rico, How He Makes His Money, and More
All right. Today we are hanging out with John Lee Dumas. He's a, he's a podcaster. Um, he's got, you know, pretty, pretty popular podcast. He does something cool, which is he publishes all of his income online. So the guy's generated like $22 million in the last 10 years. He says, here's how much I've made. Here's how much I kept after expenses. He then moved to Puerto Rico and pays like 0% tax, a 4% tax basically. So we talk about his business, how he makes his money, why he moved to Puerto Rico and the pros and cons of that. And, uh, what else did we talk about?
We talked about fasting. He did a 10-day water fast recently, so he told us all about that. We asked him if he knows of any marketers that are making just stupid amounts of money, um, because that's what I was curious about. And we asked him a ton of good— a ton of good stuff. What did you think? He, uh, he's got some, um— he's got big energy. He's got BDE, man. He's—
he was fun. I didn't realize he would be fun. And I think there was some good, good good comedy in this. I would give this one— I'm not even ask— I'm gonna even ask Producer Ben what he thinks. I think this is an A episode. A or A+. Either one. I'm gonna save A+ for when some real special shit happens, but this was a solid A. Like, I would want to listen to this conversation because I think I would hear some things that I don't otherwise get to hear. You don't really get to hear how people make their money, earn their money, you know, what, what the actual numbers are. People are very cagey about that. And, um, also this guy was very opinionated. He was like, Y'all are fucking stupid for living in California and paying those taxes. And here's why. Here, you know, here's how my life works, you know, you schmuck. And so I liked his opinionated nature. I thought that was, that made for a good episode.
Also, how about him just making fun of me constantly?
Like, that's why I was like, oh, you must be boys. Cause you must be super close.
I don't know about, I mean, I like him, but no, he just kept making fun of me. He was like, dude, you don't even travel. You don't even, you've never even been anywhere. I'm like, what are you talking about? Like, you're just making fun of me, you bully.
Yeah. You're like, I'm in Portugal right now.
Yeah, he just, he just bullied me on my own pod. He just alpha'd me hard.
Yeah, actually, I think that should be the title of this, like, Sam Gets Out-Alpha'd, and we talk about Puerto Rico and a bunch of other stuff. All right, enjoy the episode.
I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back.
So hang on, do you guys know each other well?
No, done a fireside chat together and you know, he said, he said a couple insinuating things on stage and I've really never forgiven him since.
Oh great. What did he say?
It's actually not even like, like it shouldn't be repeated to be honest with you. Sam's like trying to think if he actually said something, which he didn't. It was amazing.
So why don't you do an intro then since you guys are buddies.
So. John Lee Dumas. He's had this, uh, well, I think it, no, it started, it was always a podcast. I couldn't remember if it was a blog also, but blog, podcast. And, um, he's had it for like 10+ years. Uh, I've listened to him forever and he interviews entrepreneurs for a long time. It still is. It's every single day. It's only 30 minutes. And one thing that he did early on that he still does, I, in fact, I think you're one of the few people that still does is he releases his income every single month. And so like, I think in January he made like $200,000-ish from podcasts and another like $15,000 selling notebooks and another tens of thousands of dollars selling his podcasters paradise. So anyway, he's a— well, how would you describe yourself, John? You're a podcaster.
I'm a podcaster, entrepreneur, wannabe influencer. Wannabe Sam, you know, all of those things fit.
But he's been doing this for years. And when I told him this on our— on his show, and I'm not bullshitting, when I started The Hustle, I basically went and watched a ton of his interviews. I did it with him and MixerG, and I tried to figure out how newsletters worked, and I figured it based off of his interviews. And he would interview like Ben Lear, founder of Thrillist, like right when they were starting. And like once they— and then also again when they were getting successful and I could like figure out how to grow it based off of those interviews.
So it's— well, you obviously figured it out.
Yeah, we figured it out. And he's got this amazing database of, of like interviews and it's just kind of like gold for research.
Have you interviewed Andrew Warner? Speaking of Mixergy? No. Get him on the show, man. That guy is a character. Like, he's great. I love Andrew.
Yeah, he's my buddy. He's, he's a wild man. Um, get him on the show. Uh, so by the way, I gotta tell you this, Sean, did you see the email that I sent you?
Uh, one about the podcast charts?
Yeah. So John, I don't know if you believe this, but Sean, what did it say?
Subject line: HubSpot has 8 podcasts in Chartable's top 200. And then it's like us at number 9, Gold Digger at 32.
Um, oh, I believe it. Listen, HubSpot's only going after the players. Like, I recruited Jenna Kutcher, I got Amy Poorfield in the house. Sam, you know, and My First Million is obviously blowing it up. I mean, HubSpot's going big here, bro.
Dude, I built a product that was called Blab a long time ago. I don't know if you ever ended up using it, but it was used by a ton of like podcasters and internet marketers. They like were one of the groups that flocked to it really early because they're like, oh, a stage I can stand on.
And I was actually on a Blab and like Tony Robbins jumped in and like the whole thing just like exploded.
Yeah, it was crazy. But you were like, everybody referenced you. And so I didn't, I didn't know who you were, but they were like, you know, John Lee Dumas, blah, blah, blah. They just kept saying your name. And so I have this perception in my head that was like, you were like some either, I didn't even know which one it was. I was like, is it marketing or is it podcasting? I didn't know which one it was. Yeah. But you had a ton of respect in, in, in those communities.
And so, yeah, I did. And I still do. Yeah.
You, Gary Vee, you know, there was like a couple people that—
Yeah, just stop there. Just me and Gary Vee basically. We're the two people.
All right. So Sam, where do you want to start?
Um, here's the first thing. So I've actually said, John, that I love that people like you and, um, Buffer does this, ConvertKit does this. They reveal their revenue, but I personally would never do that. And I think it's, I think it's crazy. So like a lot of these YouTubers do it. So this guy, Graham Stephan, did it. And then what's the other guy? Meet Kevin. I think is his handle. His name's Kevin. He was like, here's my $50 million portfolio. I think that's crazy. But you, every single month for like 8 or 9 years, however long it's been, you've revealed your revenue, your profit, where the revenue has come from every single month. Do you think that that has been a net positive? Of course it's been a net positive, but will there be a time where you're like, all right, this isn't worth it for me anymore?
I don't know. I mean, you know, it's really important for me that people know that I'm really rich. So that's kind of a big deal and I want to keep publishing my income reports because of that. But to give you like the real answer is back in 2011, I, I thought all internet stuff was scammy. Like I had an Army background. I was an officer in the US Army for 8 years. I had been in corporate finance. I just didn't think that you could go on the internet and do something good and positive and be a, an honorable person and actually make money. I thought it was for scammers and slimy people, which of course it is and it always will be for some sector of the population. But I stumbled across this one, um, podcast slash blog called Smart Passive Income and Pat Flynn, this guy that I didn't know from Adam, I found out about him literally that day, was publishing income reports every single month. I went back over his like last 10 income reports and I was like seeing how he was making money and that he was a family guy and that, you know, he was working hard writing really valuable articles for affiliate income and I was like, wait a second. So you, you can be like a standup person and make money giving people real value that aren't gonna like, you know, call you slimy and scammy for them giving you money. Like they're actually gonna be happy about it. And that kind of gave me faith in the internet as a place to grow a business. And I remember saying to myself that day, Sam, I said, hey, if I ever make money in this business, which was a huge question mark at that time, but I said, if I ever make money in this business, in this online internet marketing world, whatever I end up doing, I want to be the same type of inspiration for others that Pat was for me. And so a year into Entrepreneurs on Fire, I had made almost no money, but then it clicked. And at month 13, I made $100,000. And ever since then, it's actually been 101 months exactly, because we do an income report every month. So 101 months now. We've published a monthly income report, bringing on our lawyer to give a legal tip, our accountant to share our tax tip. And we just try to share what's working for us, what's not working for us. We've made some huge mistakes over the years and we share those in the income reports as well, which is why some months are lower than others and some months are higher than others. And it's just part of the transparency that I wanted to bring to the space.
So you're always going to do that.
I don't foresee a time stopping that anytime soon. There'd have to be like a real world event where, you know, I, I had, I stopped for a reason that's not for a reason that's currently existing.
Do you think that you're a target?
And that could be the reason, honestly, is that because I could become a target, 'cause now people see how much money I'm making, where the money's coming in from, where it's going to. Can definitely make you a target. I mean, it's, you know, it's, it's, it's a crazy world out there. There's hackers or scammers. If anybody's involved in the NFT and crypto space, you see every single day people are getting hacked and scammed and all this stuff. And, you know, you've got to remain vigilant and nobody's going to be perfect. I'm not going to be perfect, so I can make a mistake. And then boom, boom goes the dynamite.
And it says since 2012, so 10 years, gross income $22 million. Net income, $16.7 million. Yeah. And that's in a 10-year period.
That's post-tax, by the way, 'cause I live in Puerto Rico, so I get to keep the money I make, unlike almost everybody else in the world.
So when did you move to Puerto Rico?
6 years ago. Thank God.
And explain what led to that. So you met somebody who was doing this and you're like, that's not a bad idea.
You started looking into it. No, nothing like that actually. But that was a good guess. Yeah. What happened was multiple years in a row, I was paying 7 figures a year in taxes, which I'm sure you guys are very familiar with. Like literally writing 6-figure checks every couple months for estimated taxes, like multiple, and just being like, blah. Like, it's like 2 steps forward, 1.5 steps back. And I just realized, I had this really kind of big realization that, you know, except for the minute percentage in the world, you can make money anywhere in the world, but you can't build wealth. You can't build true wealth paying 40, 50, 50-plus percent tax and taxes every single year. You just can't do it. So I started exploring the different options like moving to Texas, blah, Florida. Like, am I going to move to Florida to save, you know, like 10% on state taxes? Like, it's not worth it. Like, it's the federal tax, 37-plus percent. That's the killer. So found out about this unbelievable incentive of Puerto Rico. They launched it back in 2012, actually, which was called Act 20 and Act 22. And it was fantastic. It literally said if you move your business to Puerto Rico, which is an American territory, you retain, of course, your US citizenship and you pay a flat 4% tax rate on all your corporate earnings. You pay no federal, no state. And the best part— this is where my real wealth has extrapolated to like the moon. Is you pay 0% capital gains. So any money you made on stocks, real estate, crypto, 0%. It's amazing.
To play the devil's avocado, to play devil's avocado here, I think that I don't— it's probably true also that you love it there, or maybe I think it is, but you didn't You didn't say that you loved it.
And it sounds like— love it here. Love it here.
I think, I think if you are moving somewhere just for tax reasons, though, I think that's, that's ridiculous. Because isn't that the point of being rich, that you can like live where you want to live and you could do what you want to do? And I mean, how much of— was the tax the number one reason?
The number one reason. And I think it's ridiculous not to move with the situation because it is unbelievable what you can do when you start keeping the money you make with the investments that you make with the compounding. I mean, think of the millions and millions of dollars that I've saved over the years that I now have been investing in all these companies, money that I wouldn't even have had, the government would've had and, and thrown it down some empty pothole. And now those companies are returning to me 5, 10, some of them 100x shots that I never would've even been able to take without that. So I'm going from like this person that would've been like doing my best to like squirrel away like a couple hundred thousand dollars a year investing in, you know, conservatively. 'Cause I don't have much of a cushion in the stock market making like 4 to 6% a year. And then, oh no, 7% inflation comes and all my gains are gone anyways. And it's like, what am I even doing in this little rat race? Moved to Puerto Rico, freed everything, and I will never leave. And oh, by the way, I lived in San Diego, so I was in this little two— it was beautiful, but it was a little two-person apartment. On a beach, like, you know, $5,000 a month, you know, great view, all this stuff. If I wanted to buy a house, it would've been way like, like $7, $10, $12 million in La Jolla to like, to maintain the kind of location that I wanted to maintain. I moved to Puerto Rico, $2 million bought me a 6,000 square foot mansion on the Caribbean. In 17 months, I had saved more in taxes than the house cost. Period. So now I have this property in the Caribbean in an amazing community. I can still travel 6 months of the year doing whatever I want. I can still live in California if I want 4, 5, 6 months of the year or wherever else I want to be. And I get to actually keep the money I make. And something that we don't even talk— we haven't even talked about yet, but the 6-figure philanthropy checks that I've written to causes that I believe in, like Pencils of Promise. I send a Puerto Rican to my alumni, Providence College, every single year that I sponsor to my, to my college. So I have a freshman, sophomore, junior, senior year, and every year I add another one to the queue. I mean, these are things that I'm able to do because of the incredible disposable income that I have that wouldn't even have been a sniff if I had stayed in California.
And a bunch of other people move to Puerto Rico, so you probably have a community of people who believe what you believe and you've met there. I would assume you've met a bunch of other kind of Americans who have relocated into Puerto Rico and—
Well, to that point, Sean, like I actually call it the Puerto Rico funnel, and this is actually where Sam doesn't fit into the funnel, and I'll explain it to you right now. The funnel is number one, you've gotta be financially successful 'cause otherwise you're not looking to move. So of course Sam checks that block. He's financially successful. The next step down there though is you've also gotta be location independent. You've gotta be able to work wherever you want 'cause you're down here in Puerto Rico, so You know, check that block. Sam checks that block, I'm sure too. The block that Sam doesn't check, that, that, you know, is the final part of the funnel that to me makes the coolest people move here is you've gotta be adventurous. You know, you can't be like Sam, like, I'm gonna stay in the exact same place that I've been forever because I don't wanna move. That's ridiculous. No, you've gotta be somebody that's like, you know what?
You just moved.
I'm, I'm going to get out there on a limb and I'm gonna go try a place out in the Caribbean. And guess what, Sean, if it didn't work, if Kate and I didn't love it, we would've gone back in a heartbeat. 'Cause it's not worth it if you're not loving it. Yeah, of course. We came out here, we were adventurous, that one block that Sam can't check in this funnel, and we fell in love with the place. And so all the people that do fit all of those checks and they move here, they're amazing flipping people and we could have the best time with them. It's amazing.
All right, Sam, I will let you rebuttal. You have 20 seconds for a rebuttal.
For the record, just take it from Missouri. Yeah, I'm from Missouri. I lived in California, in San Francisco for 10 years. Now I live in Texas and New York, and I'm doing this podcast from Europe. I've been, I've been a few places. I've lived in Australia. Come on, give me a break. Just, but my whole thing is like, the point of being wealthy is I want to live around my family and I want to have power. Most of the year.
And see, that's actually another thing I don't want to live away from my family. So that's another thing that we, we differed with. So you, uh, we'll let, we'll let the listeners decide.
When the, when the hurricane hit, did you have power?
Not for 4 months.
4 months. Okay. Yeah. Strong rebuttal there. Strong rebuttal at the end.
So, um, so a week before the hurricane came in, I booked a one-way flight to London, England, and Kate and I spent 3 and a half months traipsing around Europe at one Airbnb to the next Airbnb while my full-time handyman that, by the way, I can afford because I live in a place where I don't pay any taxes except 4% and 0% capital gains, is living in my house, fixed up a few of the windows that broke. I came back to a perfect place. My life didn't even miss a beat.
And so, uh, have you met any other interesting characters there? So tell us like kind of some other archetypes, you're like, okay, podcaster, blogger guy, you—
Logan Paul moved here 'cause he's a smart dude. Jake Paul lives here. Brennan Bouchard lives here. Tai Lopez lives here. I mean, listen, everybody that I just mentioned, they're just smart people and that's why they moved here and that's why they're living here and that's why they're not like moving to some, you know, podunk place in Texas because the barbecue's great here. No, they are living in a Caribbean paradise.
I mean, it wasn't exactly Murderer's Row you just mentioned, but I'll let that pass. That wasn't, you know, so true. So, so you, okay, let's shift gears a little bit. You make a bunch of money and you don't have to pay taxes on it. Fantastic. You get to do other things. Philanthropy. Fantastic. What do you invest in? So we like to, to kind of break down people's portfolios. Where do you kind of allocate capital to?
So give us a kind of pie chart. Yeah. So I do a lot of stock investing.
I see that on your website. Is that—
I do a lot of— no, I don't, I don't put personal investments on my website. That's just an income report, money that I make income-wise for the, from the business. But I do a lot of like angel investing in companies. I'm part of a couple groups. I think you might know, you know, Josh Benzoni, right, Sam?
No, I don't.
And Josh. Okay, well, there's, there's a couple of them that, you know, they have these like Ma— well, it's called $100 Million Masterminds, and they essentially get together Dan Fleischman, Josh Benzoni, and there's one other person, I can't remember his name off the top of my head. And they essentially are vetting these potential angel investment deals, and then they take the entire round as part of people that are in this mastermind.
Yeah.
And that's been really enjoyable to see, 'cause you know, they're doing like all the legwork with the legal and the financial, and they bring the people to kind of pitch to us to the deal. And then, you know, there's hundreds of people in this mastermind, so only a percentage of people are jumping in on each deal. So angel investing's one thing that I do. Another thing that I've been getting really big into is both cryptocurrencies and NFTs, going deep in there, you know, guts, a bunch of blue chips like the Bored Apes and the World of Women's and the Cool Cats and all those jazzes. And you know, just seeing where that's going, just kind of having fun with that. And then on the investment side of things, I stay away from physical, like investments as far as like, not interested in owning actual real estate. To me, like anything that might cause me real work in the real world, I'm not as interested in. But I do also hold a decent stake in both silver and gold as part of a kind of an inflation hedge strategy.
No stocks.
Earlier you said that no stocks, zero. I used to own a lot of stocks. I used to be in corporate finance. I owned zero stocks.
And what's your reason why?
'Cause all my money that would otherwise have gone into stocks is all into something that I consider equal to stocks except a lot more high risk, high growth, which is the cryptocurrency, the tokens, the coins that I invest in. And you know, I'm, I'm investing in mostly the quote unquote blue chip cryptocurrencies, like the top 25 coins for the most part. I have a couple maybe in the 25 to 100 range and then maybe like 3 that are, you know, just complete degenerates, but, you know, could 1 million X if everything falls into place.
You said earlier that you've had these, I think you said 5, 10, even 100 X. When you were referring to 100 X, was that some, angel investments and which one has been the biggest?
So my biggest current investment, and this may or may not work out, and again, when I said 100x, it was like, that's the reason why I'm investing in these, because that's the overall hope. Although the one I'm about to explain to you is, you know, currently a fantastic— is looking fantastic right now. And it actually happened because down here in the community, I invested in a SPAC a special purpose acquisition, and it's basically a blank check company. And they ended up merging with, um, Trump Media. And so I actually have a lot of money that I invested in the SPAC at $4 a share. That's the price of the SPAC. And as this is today, the, um, actual merger is, which I am locked into, by the way, for at least the next 6 to 8 months. So who knows if it's gonna turn out to be anything. It could go way up from here, it could, could go way down from here. But those share prices are currently sitting at like $88 per, and my cost basis is 6 figures at a $4 cost basis. So that would be, you know, a massive multi, multi, you know, 8-figure return.
Sam, have you seen that one? That, that SPAC, it's called, I think it's—
DWAC. It's called DWAC. Digital World Acquisition Corporation.
It's pumping right now because they just launched Truth Social yesterday.
Yeah. Yeah. His new app, Truth Social.
So are you on Truth Social to support your SPAC?
Support your local SPAC? I'm a little nervous. I don't wanna, I don't wanna spread FUD, but I mean, like, I literally went on the Apple Store, downloaded the app, entered in my email, my phone number, and it said, we'll send you a code. Never got the code, went back to the app and I like forgot password error, something else error, something else error. And I, I can't even open the app now. And I'm like, yeah, yikes. This, this could end up being a, a 5% return, but right now it's about a 500% return.
That's funny.
How hard, Sean, can you— you're in the space. Why can't he figure this out? Like, 'cause he's, I mean, he's obviously not Trump. He's not the one running this obviously, but like, This is like the, the second or third time that it, the app, I think it's blog too. They both like screwed up. How, how can they not figure this out? How hard can this be to like get a team, a 20-person team to just get, make this happen?
So a couple things. One is I think that initially the, the first kind of false start they had, I think it got leaked before it was ready. Like the site was not ready. Somebody came and squatted on Donald Trump's like name because they're like, oh look, I found the, I found their website. Like, you know, I just made an account. I took his name. Like, and so, so they weren't ready. Weren't ready at that time for it. So when people first saw it, they're like, what is this janky? This is their big thing? But it was like, no, that was like, you know, not meant to, it seemed like it was not meant to be released. It was that bad that it seemed like it was not meant to be released. Then when they do stuff, like when you put, when Trump puts something in the store, it gets like a crazy amount of traffic and it's very hard. Even when you think you've prepared for scale, you, uh, the problem with preparing for scale is you plan for a lot of users. So it's not like you didn't anticipate it, but you just don't know where your system's going to break. So it's like, um, the example that, that I've heard before is like, imagine you have a bunch of pipes and you, you're worried about a leak. And so you could either spend like, you know, 12 days just walking down each inch of the pipe looking for, is it okay? But it's like a huge pipe system. So you don't, you're not really ever going to be able to see it. Or the only real, real way to know is you turn the water on and you see where the, where the leak is. And so like the problem with launching something when you're high profile is you turn the water on, but you turn it on at very high pressure, at very high volume, and you'll find wherever your leak is. So for example, Coinbase, which is like a thousand-plus-person engineering, uh, Silicon Valley blue-chip company, did their, um, Super Bowl commercial and it was the QR code bouncing around on the screen. And so many people scanned it and went to the site, their site crashed. Now you, Again, you'd be like, dude, Coinbase, you've been, you have 1,000+ engineers, you've been going, you know, this is the Super Bowl. Why did this break? And it's, it's not because they, they underestimated it. It's almost always because some part of it that you didn't expect to fall over falls over, but you can't really test it without massive scale. So that's my long-winded answer for you. Yeah.
And I've seen that happen, by the way, like in the NFT space. I mean, these people are, are, aren't at that big of a scale, but you know, they have Discords of like 250,000+ people, so they know there's gonna be massive traffic when the mint happens, but it never ever not crashes. It crashes every single time. Bots happen every single time. DDoS attacks happen every single time. I mean, it's not like, oh, half, no, it's 100%. It's crazy.
Did you guys, did you guys see what happened with the Coinbase commercial? So basically, what's the, what's the founder's name?
The guy with the—
So Brian Armstrong does this like 10-tweet tweetstorm where he said like, you know, we bought the Super Bowl ad spot for X millions of dollars and we weren't really sure what we were going to do with it, but we knew we'd figure it out. And we were sitting in a room, sitting around a whiteboard, coming up with ideas. And you know what? They all just seemed gimmicky. None of them were really true to us.
And I thought that— not sitting around a whiteboard, not sitting around a whiteboard. It was we got pitched a bunch of ideas, but they all seemed like basically others came and pitched us their ideas and they all sucked.
And they all sucked. And we were just sitting around and they're like, guys, this isn't us. These are all gimmicky. We gotta do something unique, something original. And that's when someone came up with this brilliant idea just to do a QR code. It was just a small thing that we were kicking around at first and we said, you know what? That's brilliant. Let's do it. And this one woman replies, who's the CEO of the app agency.
You, you, you missed the key part, which he, he says something in his, So he's doing a victory lap basically. He's like, ah, it started with the best thing. It's like the, uh, people always ask me about my skincare routine, so I'm gonna do a breakdown. It's like, people been wondering about the backstory behind the Super Bowl commercial that was super successful. So let me just go ahead and tell you. And it, which is fine. Take your victory lap. That's cool. I like that. And, uh, but he, you know, he was doing the thing and then he was like, you know, um, this wasn't gonna win awards at Adweek. It's not something some fancy ad agency would do, but it was like, it was just scrappy, creative, and it was just us basically. That was his message. So he specifically was like, no agency would've ever like, you know, come up with this like stupidly simple thing. It's like black screen with a bouncing QR code with flashing music. And he's like, you know, that wasn't gonna win any fancy, you know, like aristocrat awards, but it worked and that's all that matters. Right? So that was the con— that was the key setup where he kind of built his own, you know, trap.
And then the woman who is the CEO of the marketing firm, she goes, actually, Brian, we came up with this idea. You could see it in paragraph 3, page 14 of the plan that we pitched to you, along with page, you know, 49, paragraph 5. It says— and she like highlighted like where you could see that she came up with the idea. And it was a— I like this guy, Brian. It was a wonderful dunk on him, though. He that, that was not a good look.
Yeah, I think the commercial was great. Coinbase is great. He's great. But that's all right. You get, sometimes you get smacked down. I've been, I've been slapped around my, you know, many times.
What do you think I've been doing to Sam the whole episode?
Yeah.
Sam's been getting slapped. Every now and then he needs to get slapped down a little bit.
Come on. And then he tried to walk it back, but he like, you kind of, he barely walked it back. He was like, he said, this is where I was like, ah, you, you know, you messed up. Like, I totally like the victory lap. No problem. I, I believe that he didn't know and didn't realize that it was an agency that had given them the idea. Um, so, you know, cause otherwise why would he say that? It's pretty stupid to say it if he knew. So I, I give him the sort of pass on all that, but in his like apology, he was sort of like, he gave only like a centimeter of an apology. He was like, uh, I don't know, we could pull up the, the exact thing, but he said something along the lines of, You know, I didn't realize it was an external— like, he's like, he first, he said it wasn't an ad agency, it was a creative marketing firm that helped us. And is that like splitting hairs? Like, as if that mattered. And then the second thing was like, the teams worked so well together, I didn't even realize it was another company. It's like the synergy was so strong.
Yeah, strike two.
Uh, John, I've got a question for you. So you mentioned guys like, uh, Tai Lopez and I, because you've been in the game for a bit, you're not necessarily in this world, but I think that, you know, a lot of these guys who are in this world who are like the Tai Lopez, what's the, what's the other guy? Grant Cardone. And then there's like Abraham. What's his, what's Abraham's? He writes good books. Jay Abraham. Jay Abraham. Yeah. He's right. Writes some really good books that I've read and I dig him. Of those folks that I mentioned and other people who are in that world, One thing that I've always thought about these guys is I'm like, well, they definitely crush it as like, quote, internet marketers. So I'm kind of like negatively stereotyping them as these like other group. But there's no way that they're like worth hundreds of millions or billions of dollars like the real, you know, startup guys who could sell a company for half a billion or billion dollars. Is that— of those folks, do some of them actually truly just knock it out the park and crush it in terms of building really big profitable companies?
I literally have no idea. I have no idea. I do wonder why some of them stay so high profile and keep working so hard if they have. That's kind of a question that I've always had. I'm just like, well, you know, there's a million things you could do, but you keep doing this thing. So, you know, I— but I just don't know.
I see. So one thing that Grant— like, I don't know who Grant— I don't know Grant Cardone, but Sean, you know who he is, right?
Yeah, yeah, I'm very familiar, I would say.
So he— I think he has like over $1 billion in assets under management in terms of multifamily. And for years I was like, this guy's full of it. But if you look closely, he rides— he has this jet, this fancy jet. And if you look really closely, the name, the seats of the headrest, the headrests on the seats are embedded, like embroidered with his name, you know, GC. And I was like, oh, this, this has to be legit. How I'm like, this guy, I mean, it, it, it, I don't think he's lying. He's got like a $50 million jet with his name embroidered on the headrest. That's, this isn't a rental.
Yeah. And I, and I actually have a question for you then, because you know this world better than I do, the one I'm about to inquire you about, which, you know, you said you have a guy that can sell a company for half a billion dollars in the Silicon startup world. In my impression, I'm just like, that person's probably sold like 99% of their equity to venture Vultures years and years and years ago. So when they're getting out, I mean, are they really sitting on half a billion dollars? I mean, or a percentage of that?
No, I would imagine in most cases— Sean would know even better than I would imagine in most cases that you see these massive close to a billion exit. I would imagine the founder owns between 10 and 20%, maybe.
The, like, still a lot of money.
Famously, the low number like is like 4%. Obviously there's outliers, but like I remember when Box.com went public, it was like, wait, The CEO only owned, it was either Dropbox or Box. I don't remember which one. I think it's Box. And he owned 4% of his company at that point. Um, but you know, there's other, you know, cases where they own 20, 25%. Um, you know, I know several people that own 70% at the, at the billion dollar sale. So, you know, obviously there's a range. I would say your estimate of like sort of 15 to 20%, 10 to 20% is, is probably the correct range. Uh, like I think you can go look at like when Twitter went public. 'Cause you have to think first multiple co-founders. So you take 100%, you divide it by either 50, now you own 50 or 30, and then you're gonna take multiple rounds of dilution. And so you, you can basically as a rule of thumb, assume like 50% dilution is like a pretty standard number by the time you get to an exit. Um, so if you owned 33% 'cause you had two, two co-founders, well now you're down to half of that, right? And so, so you end up in that range that we talked about.
Well, and then 10 or 20%. Well, and then you have to, you, Typically you have an employee pool that's 10 to 15% as well.
Well, yeah, I'm saying all in, all, all in your dilution ends up at that. But then, you know, the, the, the crazy thing is usually the story doesn't end there. So you either get acquired by like Facebook and then guess what? Facebook stock runs up over the next 10 years also. Or you, you go public and it's like, yeah, what Box went public at is, you know, not the same, but what Box is today. So you still own those shares free and clear. You've vested them. And so you can go do whatever you want with your life.
And, uh, you know, you can still appreciate like, Hopefully you move to Puerto Rico so all those capital gains can be free.
Very few do, which is kind of surprising. Like when I hear about the Puerto Rico thing, I'm honestly like, what am I doing? Yeah. And not just 'cause you were—
I think the same thing.
You were very convincing. But really like, it's very—
Did you exit Blab?
What's that?
The next— Did you exit Blab?
Okay. How much did you own of that pivot when you sold it?
I owned 20%, but we sold it not for stock in the company. So we basically sold the assets and like the code, the team, all that stuff as like a bundled deal, but they didn't buy the actual shell and shares. And so we negotiated a like custom deal basically upon sale. So I ended up with a different number than the 20% that I owned. And same thing for my team. Like if, like I just made sure everybody got a win, the investor got a win, everybody got enough of a win. So we tried to divvy it up that way.
But now when you look at a company like Riverside that like we're on here today, like, are you looking at this company saying, oh, I know what's going on behind the scenes 'cause I did a similar type company? Or do you consider like Blab completely different than, than Riverside?
Blab was different because Riverside did what we refused to do. They were like, we're gonna just be a tool. We're gonna charge $9.99 or $19.99 a month and we're gonna be a niche tool for podcasters. Whereas with Blab, like you remember there was an audience when you were live talking like this. So there was like, yeah, the goal was to be more like what Clubhouse became or what like, you know, a lot of the live streaming products became where it's like a, we were trying to build like the next Twitter and it was like go big or go home was like the, the kind of mentality for that. We had a bunch of like, like Cisco and Oracle were using it and they were like, hey, you should just make this for enterprise because this is way better than Citrix. And we were like, yeah, but the problem with that is then I'll want to kill myself. So what do you, what solution do you have for that? And they were like, ah, what do you, why did you say those words? And I'm like, ah, because I don't, I don't, I don't wanna talk to you anymore. Uh, so, so, you know, they, Riverside did a different thing. So even though the grid looks the same and it's kind of a similar technology, they went down a path that said, can we get a few million dollars a year of recurring revenue through our subscription? And so, you know, it's just a different game.
And John, I think, I don't know, maybe Sean, what do you, I, I, I think that in order to get like your first substantial win, Um, I think it is far— the likelihood is better that you're gonna make more money bootstrapping a company and selling for 10%, 20%, 30% of what these huge startups, uh, sell for and try to own 50, 60, 70, 80, 90, 100% of the company.
Yeah, definitely. The probability's higher. I mean, it's like a risk-reward thing, right? So, you know, it's less risky, but the reward is lower.
Overall, but unlike— here's the shitty part, John, is like for me, and I bet you too, Sean, I was paying myself. I wasn't— we— our company would make 7 figures in profit, really good profit. I paid myself $20,000, $20,000, $80,000, and then the highest was like mid-6 figures, but lower. I don't remember, $300,000, $400,000. And that was like the last year. But whereas you were paying yourself a lot more.
And a lot of, a lot of startup folks like me and Sean, I, the only income we have, like, I have a friend that raised $35 million and the startup went south after 8 fucking years, which is crazy. Because that sucks that he just wasted 8 years and the only wealth that he made was basically his $150,000 to $200,000 salary. Like, that was his only—
that's all he was left with himself for 8 years on that.
Yeah, killing himself. It's really— it's not sad because like, it's cool that we get to take these chances, but it's just, man, it's a miss. It's a really big miss.
So Sam, have you seen his income report? So he— so you're making $180,000, I think, on podcast sponsorships.
Yeah, per month. First spot for the win.
What are we doing? What the hell is wrong with us, Sam?
John, listen, here's the numbers. So this podcast, I'll give you December's numbers because that's what I remember. We are at, I think, these are ballpark numbers, 500,000 in YouTube visits or like YouTube video views a month and then roughly 1.3 to 1.4 million 4 in, uh, podcast downloads. According to Chartable, that puts us as number 9. I don't know if that's true, but whatever. Are we— what, what, what could this podcast make independent?
Independently?
Independently.
Because your number is an independent number, right? Or your number's now the hot— now you, do you put your like HubSpot deal right here in public?
Well, my HubSpot quote unquote deal is that they're sponsoring 50% of my episodes. So you can pretty much deduce from whatever I make sponsorship-wise that half of that's come from HubSpot.
Right. Okay, great. Perfect. I need to go renegotiate. Actually, I don't even know. Maybe that, maybe that is about the same. Well, it depends how many downloads you get, right? As we started the pod, you're not on those charts. So what's going on? What are your monthly downloads?
Yeah, so I'll pull up my downloads from last month and this will be podcast downloads only because we don't aggregate everything else because they're a fraction of what you're talking about anyways. But so for the month of January, we did 2.968 million. So just under 3 million listens for just the podcast.
And you do, how many episodes do you do like in a week?
We do 30 episodes a month.
Oh, okay. So you do way more, way more episode volume than we do. We do, we do 8, 8 a month. Yeah. All right, Sam, we should strap it up, baby. Every day.
V and U Crowd here.
We talk about, you know, hair and workouts.
And that, by the way, is kind of one of the secret sauces for my sponsorship revenue. All these years is like when they came to me back in 2013, there was a company called The Midroll and they said, hey, we're coming to you to, uh, first to sponsor, uh, for business podcasts. 'Cause they were only doing comedy podcasts before that. They go, and then we're coming to you because you do 30 episodes a month. That is 60 potential sponsorship slots. 'Cause you can have 2 pre-rolls, 2 mid-rolls, and 2 post-rolls. And even now I actually, add a third mid-roll. So now I have two pre-rolls. Some episodes I have three mid-rolls and then two post-rolls. So they're like, you're giving us like 60 to 75, um, sponsorship slots per month. Whereas a weekly show, we're only getting 8. And so, you know, we can bring you an episode, we can bring you a sponsor for $200 a month. $800 may not be exciting for, you know, somebody, but $200 an episode, $800 might not be interesting for somebody doing a weekly show, but you know, $200 times 30, all of a sudden that starts becoming a little more exciting money, especially for me who was just starting out. So I think I made $12,000 the first month I was, I did sponsorships and all of that was because it was 30 episodes. So the quantity was huge.
So what, what, what could, what, what could this podcast earn? My MFN. So let's just say, uh, so let's just round down, let's say a million. So a million would be what?
The easy way is just what do you charge? You charge a CPM, like, like a fixed CPM across all those. What's your CPM?
We charge between a $25 on the low if it's a longer-term sponsorship.
Yep.
To, for the short, for the short sponsors, people like, oh, we want to test a month.
Right.
That's gonna be $35 CPM.
Right.
All right, Sean, I think we're, I think we're in, we're, we're all in the, in the range.
He just does way more volume. 'Cause he's, you know, in Puerto Rico, he just goes, he's sitting at the pool, comes back inside, dude, records.
Most important thing to remember, I'm keeping all this money. I mean, believe me, because I remember, guys, I remember when I would make— I would do these webinars all the time in San Diego when I was pushing Podcasters Paradise, and we'd make $30,000, $40,000 on a webinar, and I'd be like excited, but at the same time I'd be like, oh, that's, that's $20,000 in taxes right there. Like, it was literally like quenching my entrepreneurial soul and I knew I had to leave, man. I knew I had to start keeping all the money that I made.
Is there—
are you gonna have kids?
Yeah, we're actually getting married April 23rd right here in Palmas del Mar, Puerto Rico, my community, because it's that awesome. Thank you. And then, uh, goalie's getting yanked, so, uh, we'll see. I mean, I'm 42 years old, man. I'm no spring chicken. I may not— I may not have been able to have kids for 10 years now. Who knows? I mean, that would explain a lot, to be honest with you.
And you want to raise your kids there?
100%. Oh my God, I wouldn't want it anywhere else. The families that move here, like, it's unbelievable to see what happens with their kids. They just like transform. Now they're all like cruising around in the community on golf carts. It's a huge community, by the way. There's 3,500 homes in my gated community.
So there's—
wow— 17 restaurants, 2 18-hole golf courses, 20 tennis courts, 10 pickleball courts, a beach club, a fitness club. And a K through 12 academy called Palmas Academy right here in the community. And it's just like this one all-inclusive. It's kind of like The Truman Show, you know, remember he was stuck in that bubble. I'm stuck in a bubble.
Is this where Peter Schiff lives? What? Is this where Peter Schiff lives?
No, he lives in Dorado. That's where all the rich snobs live that don't want to view the ocean. 'Cause Dorado's flat as a pancake. Yeah. So nobody except the people that live right on the ocean, which is just a condo complex, has a view of the ocean. Whereas in Palmas del Mar, as you can see here, which is where I live, we live up on these hills and everybody's got these epic, epic panoramic mountain Caribbean island view that's just to die for.
And like, if you get sick, you know what, you have to like go to the local butcher for like surgery or there's like a hospital there. I'm not gonna lie.
You wanna start talking cons? There's cons to everything in life.
So yeah, give us the cons.
There's not great hospitals in Puerto Rico. I will give an asterisk where, um, Peter Schiff lives, which is Dorado. They just opened up a state-of-the-art Johns Hopkins Hospital, which is epic. But unfortunately for us, it's like an hour and a half away. I'm actually a military veteran. I did 8 years as an officer in the Army. So, um, there's actually a lot of amazing veterans hospitals in Puerto Rico, because there are 3.5 million people here and a lot of them are veterans because it's like one of the best ways to like get off the island if you're in poverty. So a lot of people do that. So we have a really state-of-the-art veterans hospital which covers me. But for your average person coming down here, it's not the most ideal thing in the world by a long shot. Like what most families do is you get— there's a lot of doctors that live in our community and they offer their services for a monthly rate. And so like Kate, she pays $1,000 a year. No, wait, uh, $1,100 a year. And she has full-time access 24/7 to a doctor who will, um, you know, like write her prescriptions or if anything happens to her physically, he'll actually like take her to which he thinks is the best hospital for that injury or that illness and like do all the translations and get her to the right place. 'Cause he has all the connections and all that jazz. 'Cause again, another con is there's a language barrier. Most Puerto Ricans do not speak English. Where we live in our community, everybody speaks English here. So it's, that's, which is good and bad. It's bad because it doesn't force us to learn Spanish. So I lived here for 6 years. I don't speak a word of Spanish. It's just the reality. But you go outside of our community and you're like amongst, you know, the Boricuas, which is the name for a native Puerto Rican, they don't speak English like no habla inglés.
Has there, has there been any businesses mentioned on your podcasts where you start this right now? Or maybe not. You don't, you don't want to, but you're like, oh man, blank should go start this right now. This is an interesting opportunity. Is there anything in your head right now that, that sticks out as, as a brilliant opportunity that you've discovered on your podcast?
Yeah. Um, I really did just interview an interesting couple the other day and they had a, you know, one of those very romantic stories where, um, she stood him up for a date, but she felt bad. And so she ended up baking him cookies and then delivering him cookies. This is like 20 years ago. And the guy was like, well, you can get pizza delivered, but why can't you get cookies delivered? And they literally started up. This homemade chocolate chip cookie delivery service company that's now like a billion dollar company. They're sending me a bunch, by the way, right now, which I'm kind of excited about. And I was like, that's just kind of the cool ideas that I love to hear about is like these ideas, you're just like, they happened because of a reason. You're like, light bulb. I would never want to go do any of those things because I, I personally believe for me, I have the perfect business where I work 6 days per month. Um, I do 30 interviews with amazing people, Sam included, and then I get to release these episodes to the world. I make plenty of money and, you know, life is good. I get to chillax by the pool 20, 25 days a month. I'm literally leaving Sunday for 8 days in Chamonix, France. That's my bachelor party. So I'm skiing up in Chamonix. Which is up in the French Alps. And then I'm spending 3 days in Geneva by myself. Then I'm flying to Rome. I'm taking a train up to this town called Orvieto, and I'm doing a 10-day self-guided walking tour, about 15 to 20 miles any given day, walking back into Rome from middle of Italy, um, along the Canterbury Pilgrimage Trail. Then I'm flying to Istanbul. I'm going to be in Istanbul for 10 days. By myself, just doing my thing there. And then I fly back to Puerto Rico, which is like vacation away from vacation. And that's my life.
And didn't you just— listen to this, Sean— didn't you, Jen, just like do like a 5 or 7 day fast or something crazy?
So in 2021, I decided I was going to get into the healthiest state, optimal health and wellness of my life.. And you know, like most of us, we've kind of kept it together over the years, but I was like, I can't get like below this, this floor of like 100. For me, I'm like, I'm 5'10", so it was like 170 pounds. I just couldn't get quite below that. So I read this book, which was a game changer for me called The Pleasure Trap. Game changer. Changed my entire wiring in my mind around food and health and wellness in general. Went to this guy's clinic in Santa Rosa, California for 17 days, did a 10-day water-only fast with a 7-day refeeding cycle afterwards. Came back, was from a 1— from 170, went down, got down to 150, dropped 22 pounds actually, cuz I was 172 weighed in. Got down to 150 when I got back. And then, you know, put, put myself back up to where I actually wanted to be, which is like 160. And I had such a good experience with that, that over the course of this, the remainder of 2021, I did 2 more 5-day water fasts, which, you know, I had a good experience with as well. I just did it here at my house in Puerto Rico.
Sam, have you ever done a water fast or a juice cleanse or anything like that?
Just for like 24 hours. I've never done— I, I'll do, I'll do 24 hours every 10 days or so, just, just, just because it feels nice sometimes. Um, but I've never done like that long? Did— what does it feel like to go that long?
It's tough. It's day 2 and day 3, your body runs out of glycogen and glucose completely. So you go from sugar burning and you flip into ketosis. So now you're, um, really keto-adapted and you're just burning fat. And that like metamorphosis is a tough transition. So you, you feel like crap. You have like low energy, you're hungry, you're cranky. Um, but then once you kind of wake up on day 4, after getting through days 2 and 3, which are tough, You kind of have this like clarity moment of like, la. And then days 4 through 10 for me, which was interesting, no hunger, zero hunger, hunger was gone. And then I just kind of went like up and down energy, no energy, energy. Like I'd go for a walk and I'd be like, I'm much more tired than I would normally be on this walk. I, you know, no lifting, no heavy exercises. Um, but I worked the whole time and was fine the whole time. You know, got a lot of— one thing you realize, by the way, during a water fast, how much time food takes. Thinking about it, getting it, preparing it, cooking it, cleaning up after yourself. Like, it's necessary, by the way, because you almost— you're like, I have way too much time right now. And you just like, you're like, what do I do with all this time?
That's what I was gonna say. Like, It'd be kind of bore. I feel like most of my life is just preparing for the next meal. Yes.
Um, and by the way, when you do a long-term fast, you realize that that's exactly what your life is. Yeah. It's not even, it's not even a joke. Like that's exactly what your life is and the life of everybody around you. They're planning whether consciously, subconsciously, what they're doing for breakfast tomorrow. Okay. I gotta run to the store because we're having these people over or this or that, or like it's movie night, we need popcorn. It's like all people think about. And you realize every advertisement in the world seems to just lead back to some kind of food consumption. And you're just like, wow, this is a crazy world.
Which, which is great. I think like, it's great. Eating is like, we had a guy, we had a guy who lived on Soylent for 30 days and we wrote about it and he was like, I feel fine. He goes, I'm just so lonely because the most fun I have is when I'm eating with friends and like I'm traveling. You're going to travel soon, John. Like the most fun that you can have is like just going to a bar, going to a restaurant and meeting people, talking to the waitress and experiencing the culture via the food. So when I'm down, I'll— after this, I want you to send me the place that you did the 10-day thing at. Yeah, I totally would. I want to do it, but I think the thing for me—
I took 3 classes a day, like morning, afternoon, lunch. You take classes, they have chiropractors there, massage people there. Like you're learning everything. There's all, there's tons of food there by the way too, cuz people are always refeeding. So you're always seeing people eating as well. It's a very social place. But, um, it is, man. It, it can be, if not done right, it can be very lonely.
Is it like a hot— was it like a hotel? Yeah. And, and what was the cost?
So cheap. $200 a night. And it's, you like, you have your, yeah, it's so cheap. So reasonable. Um, but for us with taxes, it was like $400, Sam. So, right.
That's true.
You guys, you guys have to make $400 to spend $200. So I get that for sure. But one other thing I'll mention about this, and then actually I gotta jump to my next interview, but, um, it's the, the, it, it was the mental bandwidth that a lot of people don't think about too, cuz unfortunately your brain knows it needs to eat to survive. And so it's just like you have this little record in your head that like it just says, go get food. You're like, well, no, I'm fasting. But then 20 seconds later, go get food. You're like, but no, I'm fasting. Go get— and you just can't stop it. And so I remember after I first took like my— had my first meal, I was just like, oh my God, the voice stopped because it was like no longer just telling me to go get food. So that was The weird thing about that, that I was not expecting was the mental drain.
Damn, dude. Sean, do you wanna do this?
This, uh, you guys should do it.
I got kids, so I'm like, I'm gonna have to do it at home. You know, like I'm not gonna be able to listen.
All I can say is, listen, after it happens, after it happens, I went to a conference in, um, Orlando, Florida. And no, wait, it was, was it Orlando? Yeah. 'Cause we went to like a, I thought I was with you.
I thought I was with you.
Yeah, it was that. So that event, by the way, you saw me. I went out with a couple buddies that night to like the down to Planet Hollywood place. So it's like a real deal, you know, bars. So they were actually carding people to get in. My 3 buddies who were 35, 32, and 27. I'm 42. They all just walked in. The bartender literally was like, dude, come on. Like laughing at me that I was going to try to go into the bar without giving him my ID. Again, like right now I've got a, you know, gray beard and all this stuff, but I was clean shaven. I was super fit. Like my, I was like no inflammation in my face, like thin. And, and that guy literally did not think I was 21 years old. And I was just like, wow, that's a testament to fasting because I'm definitely over 21 years old. But anyways, guys, I got to get going. Anything else you want to talk about?
Cool, man. Thanks for coming on.
I enjoy chatting with both you.
All right, would you do the 10-day fast?
I'd probably start with something lighter. I've never fasted at all or done a juice cleanse or a detox or anything, so I'd start with something smaller. But yeah, like, if that felt good, I would go on to the next That's a good one.
Would you move to Puerto Rico just for taxes?
Dude, I sure as hell want to after listening to that. I'm like, wait a minute. I'm sort of thinking, how do I time this with the sale of a company that I own? So I'm like, okay, when would I move such that I pay no capital gains for that company's exit? I think that makes a lot of sense versus moving there like perpetually, but I would definitely just go visit and just see what's life like. I know I lived in like Indonesia. And China and a bunch of different places. And I saw like, yeah, your quality of life can go way, way up when you have like— we had a chef and a live-in maid and a driver and a mansion and like all these things for less than I have my like, you know, San Francisco 2-bedroom apartment. So like, I get it. Um, but I also saw the cons, which were like, you know, you're away from American culture. You don't— you know, your friends are like kind of just like this select group of other people who made this, this leap. Your healthcare's not very good and there was other, other issues with it. But, um, I'm kind of down, you know, I think it's—
But your wife do it?
She would not wanna do it. That's the main, that's the main reason I wouldn't do it. She, you know, we have our family here, so it's like at the end of my life, am I gonna be like, thank God I saved that money on taxes? Or like, thank God, you know, I was with my, you know, I was hanging out with my family all those random weekends that we were doing. So, um, and for me that matters. But I think I could sort of convince my family to go too at some point. So I think there's a, we would move as a tribe. Either we all move or nobody moves is kind of like our, our, our mentality. Ben knows.
I'm say like the dream is if you can pull it off with a compound.
Yeah.
You get like, like, like 15 families or whatever, your, your, your closest friends and family and all get 'em to move with you.
And then nobody has to wear clothes and everybody could just like be nude all the time. It's, that's the dream.
That's the Mormon way.
A small colony.
Yeah. You Mormons know about that. You, you, you, you have big dating circles. I don't, I don't know where the nudist angle came from with, uh, with Mormons, but, uh, the rest, I guess, applies.
Yeah. I'm just mixing two different groups together there.
Best of both. I think, um, I don't, I'm not sure if I would do it. I'll go check it out. But what I will commit right now is I'll, before the end of the year, I'll, I'll, I'll do a 5-day. At least a 5-day. I'll go to his, I'm gonna go to his place. I think that'd be fun. I think, remember I told you if I was gonna start like a, I joke, I said I'm gonna start this thing called hostage where we just steal you for 10 days and you just lose weight. Just, we just don't feed you. You just don't lose.
Results are guaranteed.
Yeah. Results guaranteed. It's just math. I think, I think, I think that's, I'll, I'll, I'll put myself through hostage. I think I'll do it. You consider going to a fasting like retreat? I know someone who did that. Yeah, I think that's the only way I could do it. I think that's the only way I could do it. You couldn't do it like just at home. You'd have to go to a retreat, you think? I think so. What I love, one of the reasons why I like, um, I like spending, uh, half the year in New York, half the year in Austin, I like to travel a lot, is when you travel and break your frame, you get out, or when you, when you, when you move to a different, when you're in physically a different location, you you also become, uh, a different— in a different frame, mental frame. And I— so I think that it's really important to do that. So like, it's called— and this is like, for example, let's just say that I took you to, uh, a Costco aisle 7, and I go, Ben, sit down. You see this Picasso? Isn't this lovely? You should buy this for $10 million. You're not in like the right frame to buy this like expensive thing. But let's say I took you to this like museum and I sat you down on this red velvet seat, beautiful lights. Did you say Costco? You're like in the first one. Yeah, I'm saying like you had like a different, a different physical location puts you in the right frame to do something. And like, you're not gonna like, if I'm in Costco, I'm not gonna buy something for tens of thousands of dollars. But if I'm in like this beautiful place, then I'm more likely to go do something. It's the same way with different fitness stuff or, uh, you know, like, like someone says they're gonna meditate for like an hour a day, I'm like, dude, I can't do that at my house. Like, it just— I'm just not in that— I'd rather go on my phone. But if I'm in like a physically a different place, I think I'm more likely to do it. So I'd rather just sacrifice and do it.
You just said a couple things that are so true. One, just changing your location will just break your pattern of thinking, which is super important. I'm— I just realized when you said that how true that is and how guilty I am of that right now, because I have this like great rhythm going, but I'm in the same place all the time. Like when I went to the farming conference, that was my pattern break. And guess what? That's where we like conceived and launched the Milk Road and now it's doing great. And it's like, uh, like, dude, would I have done that? Would I have really mustered up the energy, been able to pitch it properly, been able to like formulate the exact idea had I not just like changed my frame? It's like that conference was really nothing about, you know, it was a different kind of milk that I was thinking about basically at the farming conference. So, so that, that just shifting your, your mentality, breaking your mental pattern is so true. Uh, that's, that's what's true. Then the other thing is like, if you think about the fasting, what are you really doing? Are you really doing it because you're gonna lose weight for 10 days? Well, you're just gonna put it back on most likely, right? It's like you're doing it for the experience. Like if, if I was gonna do it, I would do it because I want a unique experience and I like questioning the things that are not questioned in my life. Like the, the things that society has just conditioned me to do and believe are necessary. I like having that red pill moment where it's like, oh, do you really think you need to eat 3 meals a day? Why 3? Why not 4? Why not 5? Why, why at these times? Maybe you don't need to eat at all. Have you ever tried that? It's like, no, I just followed, you know, the instructions in the manual of life and I just did it. So it's like, I like the questioning of life exercises and want that experience. So like, I'm, I would do it at home just because I wouldn't wanna leave my kids for like 17 days. Um, you know, just to do something kind of just for myself right now. Cause they're really little. But, um, but that's what I would want out of it is the unique experience of being in that place, changing your mental frame and then doing it intensely rather than with low intensity. Like at home I could do it with sort of like low intensity. Whereas if I'm there, I'm committed at a different level of intensity.
How's the Milk Road going? What are you at?
It's amazing. I don't wanna say, you know, uh, what I always say, I always talk about it when, when it's a, when I want your help to make it work. Like when I want the audience to help me make it work, and then once it starts working, I shut the fuck up. It's at the shut the fuck up stage. Uh, so I will Slack you, I will Slack you privately and tell you how it's going.
But, but you're getting energy from it.
Yeah. It's, it's a lot of fun and it's like the business just like, the business just worked straight off the bat, which is wonderful cuz we didn't have to like wander around and search and who knows, maybe like we'll add some things later, but like the core of it. Is working. People like it. I like it. And it's creating— the reasons I had for doing it are all happening. So I'm like, okay, well, that's exactly what I would want.
Can you see yourself producing, uh, or writing for, uh, 350 days for the next 2 years?
Ben takes the load on the writing, so he writes the draft every day, and then I edit the draft every night at like, you know, once— like, my kids sleep super late, so they fall asleep eventually, like 10 or 11:00 PM and then I'll edit it for 30 minutes to an hour, uh, at night. And so, so far that's working. Now, Ben, I'm sure at some point, you know, wants a vacation or catches the flu or whatever. And you know, like we haven't like accounted, there's like no redundancy. It's like, it's like we do it tonight or else. And so, uh, like, let me ask you this for the hustle. Did you ever miss an edition?
No, never. I don't, I don't think, I, I think, um, There was a couple times where there was like a terrorist event or something like that. Like, remember when the cops— well, remember when the Dallas cops got shot? Like, or like, you did something where like, because it was like a bad—
in bad taste or something.
Well, we had to like delete— like, I think that there was like when there was fires in Napa, or I forget exactly what happened, but there's been like these like crazy events, like when Trump won, like where it was like everyone's focused on that, we had to like scrap our plans and kind of throw something half-assed together. But we almost always— I don't think not once did we ever miss anything, but sometimes it felt like we phoned it in.
Yeah, yeah, yeah. But you didn't, you know, the button, it's like the button. No, it lost. It's like you have to hit the button every whatever. What is it like every 8 minutes or 1 hour and 6 minutes or something? They had to hit that button. That's how it feels running the Milk Road business. It's like the email has to go out every morning and for the life of this company, it cannot miss a day.
Um, and I, I mean, it's stressful, dude.
That has a lot of intensity you had with it. I know me, I skip all the time. Like I have Five Tweet Tuesday, it's been sent on Wednesday, I think like 5 times this year already. So it's like, or like 5 times the last year. And so, you know, I'm the type that like, I don't really do good with like adhering to schedules and, uh, stuff like that. But it seems very necessary for this business as a like standard to hold.
Yes, the only thing that we would do, and I think you should do, is we would be really liberal with the holidays. So for example, if there's like a holiday of like, should we celebrate this? Should we not celebrate it? We typically defaulted to celebrate it. Um, and we'll run like, we, we would have backups that we would run, but that particular day would be different. So for example, on President's Day, that would just be like a redo of like something old that we've done. Um, and so we would take advantage of holidays. Um, but that's pretty much it. But also we, we sent on Sunday too, so it was 6 days a week.
Yeah. So we do, we do 5. Um, and then the other thing, so the business is working and the feedback, like I was reading, I read the feedback every morning on like everybody who responds to the thing.
It's addicting, right?
Very addictive. Uh, but also very like, you know, um, feedback can hurt. Uh, you know, like you think you did good and people are like, you're a dumbass because you got this number wrong. This, word wrong, or I disagree with you. And so it's like such an awesome thing to feel every day is an actual feedback loop of your work. Like, if you think about it, like, you know, most people in most jobs get almost no feedback on a daily basis. And, um, even this podcast gets very little feedback, right? We record it, it comes out like, I don't know, 4 or 5 days later. I don't, I don't ever listen to it. If people like it or dislike it, like, you know, I'll get a few compliments, but I don't get the negative stuff. Typically, uh, you know, we don't really get feedback. We see a number and a number is very impersonal versus with this, it's like I get daily feedback every single day on something I created and tried to make good. And that's like a pretty awesome thing that's going on. Um, and the other thing that was cool was Chris Dixon, the partner at Andreessen Horowitz who runs their crypto thing, like their whatever billion dollar crypto fund or whatever, uh, he tweeted out something that was like, What's the coolest thing in Web3 that's going on right now? And we literally, I think, got like, I don't know, 50 to 100 mentions of people just organically just going to Chris and saying, uh, Milk Road, best thing I've— best thing I'm subscribed to for crypto. Milk Road has got to be the best, my favorite thing in crypto right now. So that's when I was like, look, Ben, that's working. Uh, like, that's what working feels like because we didn't ask them to go leave a review. Like, we didn't even know. We got started getting tagged in this, and if And so the example I'll give of that is my family was hanging out at the end of the year and we were kind of like, oh, what are you most grateful for this year? Kind of like, I don't know, you probably had a similar conversation. Like, oh, what was the best thing of the year? Worst thing of the year, whatever. Kind of had our own little over lunch, just conversation about that. And 4 of us all said that we started training with my trainer, JA. And, uh, so it's like, yeah, training with John was, uh, was the the best thing I did this year. It was the best part of my year. It was the best thing I did this year. I went back and told him, I go, dude, that's kind of crazy. Like on one hand it's like, I'm a personal trainer. There's plenty of those. Yeah, I make this amount of money. It's not like, oh, I'm this billionaire, blah, blah, blah. I was like, but 4 people, you know, that I know said that you were the best thing that happened to them in the year. Like that is the one of like the highest compliments you can get. And it just sort of changed my thinking of like, What does like high impact or what does winning even look like? Because I hadn't really considered that that could even be a part of it.
Dude, there's a, there's a reason why all these rich people buy media companies. You know, the, the one of the first Facebook employees bought, I think, The New Republic, which was a famous newspaper. Jeff Bezos, Washington Post. What did a Salesforce guy bought something? I think Time. An Indonesian billionaire, I think Indonesian, bought Fortune. A Chinese guy is buying Forbes. Wall Street Journal is— I mean, Rupert Murdoch, like, is obsessed with this shit, even though he doesn't have to do it anymore. Media, it sucks that— so media can be lucrative, but the likelihood that it will— like, the likelihood— Fox is the biggest probably media company in the world, and it's not It's probably— I actually don't want to know what its market cap is, but it's not bigger than like a Salesforce or something. Or I bet you like, like HubSpot will likely be bigger.
Right. And that sucks. And that, that's like at my heart, that, that kills me. I'm like, fuck, the thing that I love is not the most lucrative. And that can kind of suck sometimes because, uh, what did you say earlier? You said it's a 9 outta 10 hustle, but a 2 outta 10 opportunity. Media requires a 9 outta 10 hustle. I would say it's a 5 outta 10, maybe it's a 6 outta, I would say it's a 5, I would say it's a 5 outta 10 opportunity. Um, and, and that kind of blows.
Totally. If this wasn't basically, uh, my test was like, I think this is pretty much like a bad business opportunity just in general. Like of, of all the business opportunities in front of me right now, this is on the end of the worst ones. But I still want to do it, that means it's like a signal I should really go do that thing. Uh, because like if my, my emotion is actually even trumping the on-paper logic, that means it's actually what I want to go do and I'm not doing it. Yeah, obviously external outcome. But then in this one, the other thing that like bumped it was I think crypto has more opportu— higher opportunity score than if I had done media in like, let's say sports or some other thing I'm interested in. Obviously. Because it's, you know, it's the business of money, right? And it's like where a lot of the action is right now.
So You know, like, you know, The Motley Fool makes like $500 or $600, $700 million a year.
Uh, I'll give you an example of this. 'Cause we were just talking about it. Uh, we did e-commerce last year. I think e-commerce is also like level 10 hustle, level 5 or 6 opportunity, maybe level 6 opportunity, level 7 max. And, um, but I was, I was telling, uh, I was chatting with Ben yesterday and I was like, you know, what's the, one of the best startup investments in our portfolio right now is this company called Triple Whale. That is like an e-commerce, like, kind of like analytics company. And we were— I saw it, I was like, oh, I want this for our brand. And then we started using it. I was like, oh, this is a great product. I should try to invest in this. I was one of the first investors in it. So I got in at a very low valuation and it's raising now like a very high valuation. And so that investment alone is like a, you know, 30x+ multiple already. Um, and it's still pretty like early in its lifespan. That, if that keeps going like that, that could end up being a sort of like, you know, 100x, 200x return. I was like, we might make more money off that than the actual D2C business. We definitely are going to make more money off right now. That investment is going to make more in my pocket than my brand would spit off in, you know, owner, owner profits, uh, you know, last year or something like that. And you know, that decision to invest in that took 5 seconds. I wrote a check, never did any work.
Don't do any work.
Yeah.
I also wouldn't have ever invested in that had I not been doing this. And so, you know, the Steve Jobs quote of like, you can't connect the dots looking forward, you can only connect the dots looking back. I think that's very true. Early in my career, I made the mistake where I was doing something and my eyes were sort of like shut towards like the adjacent opportunities that were coming, like the halo effect, the other things that were in my world because I was in this space, right? Like, okay, like let's take Producer Ben for a second. So Producer Ben makes some money for producing this podcast. Fantastic. That's a good thing. He's sharpening up his skills. That's like the direct benefit of this job. But then there's the indirect benefits of the job. And like, what are the indirect benefits? Like, for example, Producer Ben, you've never said, hey Sean, could I, you know, maybe co-invest with you on some of these deals? Like, I would say yes to that. And you could put in whatever amount of money makes sense for you. $500, $1,000, whatever, whatever would work for you. You could be getting like the benefits of maybe the hard work I'm doing in one place because we have a good relationship. So that would be an example of indirect benefits. I looked back at my career early on and I realized how few of the indirect benefits I realized were around me. And I was like, damn, I bet if I had just asked, that would've been easy. Like for, for example, my co-founder at my last company, Furkan, he, he had shares in Applovin that I think Apple, when he left, was like worth like a few hundred million.
Now it's worth like 20, 20 or 30 billion.
It's 20 billion, 21 billion today. So it's like, it was 200 or 300 million, I think, when he left. And he told me about it. I was like, oh, that sounds like a great company. And then he kept telling me how great it was doing. I was like, oh, now we're doing this. It's worth $500 million. It's worth a billion dollars. And then it almost sold. And along the way, he like needed money. He was like, hey, can I like take some of my salary, like, you know, advance? I'm like trying to buy a wedding ring for my wife or whatever. Like I have a wedding to pay for. He's like, I'm gonna try to sell some of my AppLovin shares. We sold some back to the company. He's like, yeah, I want to hold on to these, but like, I just need cash to pay for like my wedding and shit. Like, that was the indirect opportunity right in front of my face. I could have been like, hey, best friend, well, I'll buy those shares off you, you know. And instead I was just like doing my favorite, like, you know, shuffling money around.
To go easy on you a little bit, it's not like we had a lot to—
I didn't have a lot of excess cash, but like, whatever I was putting in in the stock market, like, you know, just random ass, you know, like whatever companies they were. I basically, like, I could have got the money. So for example, we had a bunch of wealthy friends. I could have said, I could have done what I do now, which is say, hey guys, this is a great opportunity. I've found it. I vetted it. I can explain to you why it's good. And if you agree with me, you put up the cash and give me a carry for creating this opportunity.
This is my fear, by the way, of when we're talking about, um, moving to Puerto Rico. I, my fear is being, not being relevant anymore. Um, and missing on interesting things. It's not like money-making things necessarily, but not being in the thick of culture.
Right.
Yeah.
I feel that. Um, anyways, I don't know why I started ranting about all that shit. You were just trying to recap the episode, but whatever.
No, that's what I wanted. I didn't get to talk to you much because then I had a lot of stuff on my mind, but, but the, that was cool.
I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back.