Shaan announces the sale of his crypto newsletter Milk Road and brings on the buyers — Mike Whitmire and Kendall Seville — two self-made entrepreneurs who built multi-million-dollar SEO affiliate businesses in online gambling and precious metals. The three cover how the deal happened, why Shaan sold, and the buyers’ origin stories: from poker affiliate misspelling hacks to building JM Bullion from a basement into a nine-figure company. The second half is a wide-ranging conversation about Bitcoin conviction, self-funded vs. VC paths, and unconventional lifestyle choices.
Speakers: Shaan Puri (host, founder of Milk Road), Mike Whitmire (buyer, co-founder JM Bullion), Kendall Seville (buyer, co-founder gambling affiliate empire)
Introduction: Shaan Sells the Milk Road [00:00:00]
Shaan: What’s up, y’all. Shaan here. This is a special episode. My company the Milk Road just got acquired, so the news is out and I can finally talk about it. I’ve been kind of hinting at it on the podcast for those who are listening.
Shaan: This episode is me and the dudes who bought it, so you’re going to meet these guys. You’re going to ask: why would I sell? We started this thing, it grew like crazy, it was profitable, the thing was working — so why? I talked a little bit about that, but the biggest reason honestly was these guys. These are people I wanted to be able to work with and get to know better. I thought, if I give them this company — and I still own a minority stake — that minority stake in five years is going to be worth a lot because I believe in these guys. They’ve done it before. They’ve built and sold companies worth hundreds of millions of dollars, and I think they’re going to do it again here.
Shaan: The episode is a little funny. It starts off a little slow, but around fifteen minutes in we’re done talking about the acquisition and I let these guys shine. They tell stories about their early projects — some that failed spectacularly, some that succeeded. Their philosophy around business and negotiations. It gets really good after that, so definitely stick through.
Shaan: If you like this podcast, you will like these guys. Let me build the characters. You’ve got Mike, who is this workhorse. Anybody who likes a grinder, somebody who’s scrappy, somebody who can bounce back from defeat — he tells a ton of stories about basically getting his ass kicked and then somehow pulling it off. Mike lives in the details and in the weeds. It’s amazing.
Shaan: And then Kendall is the opposite. He’s like, how can I work smarter, not harder? He’s Mr. Shortcut. He’s the guy who hacked the Tesla referral program and ended up getting multiple Tesla Roadsters. He’s the guy who did the same thing with Uber and Lyft and has Uber credits for life — he just finds the clever way to get it done.
Shaan: So these two guys are awesome. I think you guys are really going to like them. Enjoy.
Setting the Scene and Meeting the Buyers [00:02:30]
Shaan: All right. So we should do this. Welcome to the show. I’ve been telling you guys you’ve got to come on for a couple months now and I’m glad we’re doing this.
Shaan: I think we should frame this a couple of ways. We got together because you guys just bought my company — you bought the Milk Road — so we’re going to talk about that, how that happened, how that went down, why you guys decided to do it, good stuff like that. Then we’re going to talk a little bit about what’s the plan. But really the thing I thought would be the best out of this conversation — my sort of secret plan — was: when we were getting to know you guys to decide, do we want to do this, do we want to actually partner with you guys and do a deal together, we would ask you a bunch of questions at dinners or at the bar or whatever, and your stories and answers were so entertaining that I was like, dude, these guys need to come on the podcast. I was like, if I had just recorded this dinner, this would have been one of the best podcast episodes we’ve ever done. Probably the best laughs.
Shaan: So my job here is to somehow recreate that dinner. There’s actually a lot of pressure. I know how good this episode could be if I do my job. You guys are going to tell your stories, and I think at the end of this people will know a little bit about what happened with the Milk Road but also a lot about you guys, because I became a fan of you during the process of doing the deal. I think a lot of other people are going to become fans too.
Shaan: You guys are pretty low-key. Why is that? Why are you guys so under the radar? I ask this as a guy who’s constantly on the stage being like, look at me. And then I meet people who are really, really great and they’re not trying to do that. Is it that you don’t have time? Is it shyness? What’s the reason?
Kendall: I think it’s probably shy, and it’s just something I never thought I needed to do. And then when I met you I was like, I’m doing everything all wrong. But we had this hilarious day in San Francisco — I usually don’t leave my house, but when I do leave my house once in a while I get bumped into. For some reason that day something was going my way, and like six or seven people stopped us in a row.
Shaan: Your reaction to that — I was like, did you plan this? I could not believe how many people were coming up to you. One guy was like, I’m a big fan of the Pod, I made an MFM search engine. It was insane.
Kendall: Yeah, that was pretty crazy.
Shaan: The guy from the hospital. He said, “I just came from the hospital looking for Shaan.” That was a little — I don’t know what that means. He had like a you know, a patient-has-escaped sticker on his shirt basically.
Kendall: Yeah, we had no explanation.
How the Milk Road Deal Happened [00:07:00]
Shaan: All right, so let’s start with the Milk Road. People want to know — the news just came out, this pod will come out right after that — we sold it, and people want to know how that went down. I could tell it from my perspective, but let’s do it from your perspective. How did this all happen?
Kendall: Yeah, for sure. Carter, who is our finance guy, was a big fan and he shared it with Mike and me. We subscribed to it, and every time we’d open it we were like, they’re doing it so well. This was maybe six months ago. Every time we read it we talked about it — we talked about the memes, how funny it was, but also how informative it was. That’s kind of what we were trying to do with bitfo: make the best content and actually have people read it. You can have ten thousand words, but that doesn’t mean much. It’s like, how do we get the seven hundred fifty words that really punch? I feel like that’s what you guys have done.
Kendall: It came to a point where I was like, we should talk to these guys.
Mike: And I think we reached out to you guys. I remember having a conversation with Ben about growth, and I was like, what if we go on one of those sites — you know, what’s the price of Bitcoin, what’s the price of Ethereum — and just offer them a dollar for every email subscriber? Let’s just see if they’ll put our ad up. I think that’s how we reached out.
Shaan: Ben reached out to somebody, got back to one of you guys. And it turns out you weren’t a kid.
Mike: Yeah, you weren’t seventeen. But we just wanted to meet you guys, so we’re like, let’s take the meeting. About ten minutes in, we were messaging each other on the side: we’ve got to buy this thing.
Shaan: The funny thing is — I don’t know if I told you this — but that same day I hit Ben with a curveball in Slack. We’d been working on the Milk Road full force. I’m a big pat-on-the-back self-congratulations kind of guy. Every day I’d basically tell Ben: this is amazing, we’ve launched this thing, we’ve already grown this fast. And then one day I just hit him with a curveball. I go, “How much would you sell this for right now?” And he’s like, “What? Do you want to sell it?” I was like, that’s not what I said. I said how much would you sell it for. He gave me a number, I said my number’s like that plus one, and he was like, okay.
Shaan: And that’s kind of what happened. I’m very impulsive like that. That’s how I got my dog. I just woke up one day: hey, get in the car, we’re going to go find a dog. We Craigslist-searched in the car and we got a dog that day.
Shaan: So literally Ben calls me later that afternoon and he’s like, “Dude, so weird — I just talked to these guys and they mentioned if you’d ever be interested…” I was like, who are they? He said one of them built the largest precious metals e-commerce site. I knew that name — JM Bullion — because my brother-in-law buys from there. He’s stashing away coins in his safe. So I was like, oh, these guys are actually super legit. Scratch the whole nineteen-year-old kid offer-them-a-dollar thing. Let’s see what these guys will offer.
Shaan: Then making the deal — somebody said this the other day: the rule of five. In any deal that’s going to get done, it’s going to fall apart five times. I think we did that. Three or four times at least.
Grading the Negotiation [00:14:00]
Shaan: I do have a question I’ve been wanting to ask. How could we have negotiated better? I asked Ben, “What can we ask these guys on the pod?” He said, “Ask them about the deal negotiation.” Could we have gotten more? Because that was the first question I asked after my first acquisition and the CEO was like, “You couldn’t have gotten a dollar more.” That feels good but it feels like a lie. So from your guys’ perspective: how did we negotiate? Give us a grade.
Mike: I would say it was an A minus.
Kendall: I was going to say a B.
Mike: I mean, I would give everyone almost a B around the table. I feel like each one of us at one point was like, ah, this isn’t gonna work. Every deal I’ve done — every time I’m like, it’s not gonna work, for one reason or another, you get to the point where they’re here and I’m here and we’re not getting anywhere close. Then you figure it out or you walk away. We had those walk-aways with you. Twice.
Kendall: I think you guys did it once and we did it another time.
Mike: I said A minus because at the end, when we made that final last chunk — that was it for us. We said we’re walking if this doesn’t work. One thing that would have helped: he has a non-compete on gambling. One of the times it fell apart was we got into diligence after we’d already agreed on a number, and there was found out a little more gambling-related sponsor revenue there than we thought. If that had come out earlier, you guys probably could have guided us better.
Shaan: Yeah, we didn’t know that was a problem because we don’t have a non-compete. So yeah — that’s all right, that’s good.
Why They Bought: The Strategic Rationale [00:18:00]
Shaan: All right. So let’s talk about why you buy a business like this — what’s the thinking, what’s the rationale. You guys have been on the seller side too. What’s the difference in mentality?
Mike: So the reason we bought: we felt like everything we were doing was just going to work a lot better on their brand. The SEO play is our thing. We build content-driven sites that we want to rank in Google for money terms in crypto — buy Bitcoin, blend Bitcoin, all those things.
Shaan: We should explain your superpower. Your superpower is: somebody goes to Google and says “buy gold online” or “best place to bet on whatever,” and your whole career basically has been ranking number one for those terms. You did it with sports betting, you did it with gold, before that with poker. That’s your guys’ secret sauce. So I was like, why do they need a newsletter? The newsletter doesn’t do that. But there is some synergy there.
Mike: Yeah. Google has really moved toward rewarding brands that users are actually searching for. Milk Road is being searched hundreds of times a day, and that’s such an indicator to Google of like, humans are interested in this brand. Same with JM Bullion — getting thousands of searches a day. When we were building our sites like defyrate.com, which was what we merged into Milk Road, no one was really looking for that site. We were just trying to figure out how to get it up in Google. So for us it was like, we get to jump forward a year in this journey by buying this newsletter and website, roll it in, and then reap these benefits.
Mike: You’re going to continue to get really amazing backlinks because you do all these awesome interviews. The newsletter content could go on the website. We’d be able to be in the inbox of our users — and there’s a different segment of users that are going to go to the website. Those ways to reach people are really exciting.
Mike: And it was working during the bear market. Our business was still growing and generating revenue and profit during the crypto winter, which is hard. If Bitcoin’s price goes down, there’s a lot less people searching “how do I buy Bitcoin right now.”
Kendall: You had diversified advertisers. They’re not all crypto companies.
Mike: Yeah, like, this can work even if crypto’s dead for a while.
Why Shaan Sold [00:22:30]
Shaan: So the question on our side was: do we want to sell? Why sell? I think there’s a three-pronged answer. First, a lot of decisions just get made through your nature and personality. I’ve gotten to know my nature over the last few years. I’m good at starting things, good at finding the something from nothing. But taking that something and just fine-tuning it day after day — which is where most of the value is created in business — that’s not something I get super excited about. I could create something, get it off the ground, get it to work, and then as it worked, my interest would fade.
Shaan: So I said: if I’m getting a good deal now, but I know it’d be better if I held it for four years — great. But am I really going to have this same energy four years from now? I can’t know that. That’s true for me as an operator.
Shaan: Whereas about you guys — and I’ll get into why I thought you’d be much better owners — Mike is an absolute animal workhorse. I’ve seen your level of attention to detail. You are looking at this email in the morning, in the afternoon, in the evening, giving feedback, doing it again the next day. I was like, wow, this guy is an animal. And I thought, okay, maybe he’s just doing this at the beginning. But no — that’s just kind of who you are.
Mike: Yeah. With JM it was the same thing. Myself and my other partner were probably the biggest readers of the gold and silver Reddit stuff on the planet because we just wanted to ingest all of it. What are the people thinking? We got so many wins just by observing and implementing those things.
Mike’s Personality: Going Uphill [00:25:30]
Shaan: I asked you guys some questions before the pod. I made a Google doc — like, what do you do for fun? And one of your things was uphill skiing.
Mike: Yeah. I’ve got a buddy who’s gotten into backcountry skiing — instead of going to the resort and riding the lift, you’re in nature. He convinced me to do one of these trips a few years ago in Yellowstone Park. We didn’t see another human the entire day.
Shaan: You’re basically hiking up a mountain?
Mike: It’s fairly tame, actually. I use what’s called a splitboard. It looks like a snowboard but breaks down the middle and the bindings rotate, so it basically turns into skis. Then you put these things on the bottom called skins — originally made from seal skin, now just fancy fabric — and they’ll only slide one way. So you can slide up the hill and it won’t slide backwards. You fight your way up, it takes several hours, and then it’s a five-minute ride down.
Shaan: Not a huge payoff. Little children coming down as you’re brutally climbing.
Mike: You do get a lot of respect from people on the lift, though. When you’re trudging up the hill, it’s a good feeling.
Shaan: Not from me. I don’t even get off the lift. But that checked out completely. The way you exercise, or the way you vacation, is basically the way you work — just grind. And if you do that in any business you’re going to increase the outcomes. We still own a good-sized chunk of the business, so I needed to know that was going to be worth something someday. That would be the only way this deal was worth it — the upfront cash is great, but your boy’s gonna spend that. I need to know that what could have been will actually get played out by guys who are super focused.
Kendall’s Superpower: Mr. Shortcut [00:30:00]
Shaan: And then there’s Kendall — Mr. Shortcut. We were talking and I was like, all right, tell me the story of the Tesla hack. Because when he told me this story I was like, oh, this guy is super clever, he’s gonna find the shortcuts we need to make this thing super successful.
Kendall: So I had a Tesla, and at the time they had the Tesla referral program. Every owner got a unique code, and to get five thousand supercharger miles you had to use it. People were searching for it. I was like, perfect — that’s what I do for a living, I rank in Google. When you searched “Tesla referral code,” my site was number one.
Shaan: What was the site called?
Kendall: It was fairestimate.com. I made it as a fun side project — an Uber vs. Lyft comparison where you could put in where you’re going and see the difference. And by the way, that itself was another one of your shortcuts — you didn’t want to pay for Uber or Lyft anymore, so you just got referral credits.
Shaan: Right, you would just get referral credits from that too. Unlimited Uber and Lyft for literal years.
Kendall: Exactly. I shared the codes with friends — they’d be like, I want some, can you put my code up for a little bit? I’d do it for a month, they’d be done, and then the next friend. But eventually these programs catch on that something weird is happening with certain codes and they cut you off.
Shaan: So you had the Uber-Lyft shortcut getting you free rides, then you made a slash-Tesla extension on your site and you were ranking for when people were looking for Tesla referral codes.
Kendall: Exactly. I sent hundreds of people to buy cars. You needed to send fifty-six to get a Tesla Roadster as the top prize.
Shaan: The Roadster is like two hundred fifty grand?
Kendall: Yeah, around two-fifty. They still haven’t released it — they were like, hey, when we release it in 2019 we’re gonna give everyone theirs. I earned 1.75 Roadsters. Tesla was like, we’ll give you 1.75 — so then I put my dad’s code in and did it with my brother-in-law. So we have a lot of Roadsters that might be coming.
Shaan: It’s like the Oprah thing. “You get a car! You get a car!”
Origin Stories: How They Discovered the SEO Affiliate Game [00:36:00]
Shaan: So how did you even learn that there’s this SEO affiliate game? SEO is people are searching for stuff on Google, if you can get to the top you get a lot of free customer traffic. And affiliate is, well, what do you do with that traffic — you pass that qualified, high-intent customer to the website and they have affiliate programs so you get the kickback. That’s how you got the Roadster, that’s how you got the Uber credits.
Shaan: But how did you even figure out this was a thing? I want to hear that for both of you, because this is y’all’s game and I didn’t know about it until much later in life.
Kendall: So this was during the moneymaker era — World Series of Poker was a big thing, all my friends and I were playing poker at the house and online. I saw that one of the poker sites had a poker chip set they’d give away for free. I was like, nothing in life is free — figured out they were giving it away because they were getting two hundred fifty dollars per person you sent. So I was like, perfect. I’ve got a lot of friends. I’ll give them fifty bucks to deposit and I’ll make the two hundred from the poker sites. I did that with like six friends and ran out of them.
Kendall: And then it was like, I need to figure out how to do this with strangers. That’s kind of how I got into making websites. You’re a teenager at this time?
Shaan: You’re in college at this point?
Kendall: Yeah, I’m in college. Mike was actually a teenager at that time.
Mike: Yeah, just how to figure it out. My first big break was actually misspelling Paradise Poker.
Shaan: What do you mean?
Mike: At the time, Google didn’t have autocorrect. So if you misspelled “Paradise Poker” you’d get misspelled websites. I was like, perfect — I’m not a very good speller, so I can come up with a lot of variations. I couldn’t tell you how to spell “paradise poker” right now, honestly. I came up with a lot of variations, got them to rank in Google for every misspelling, and all of a sudden I just started seeing traffic. I was sending them to the real Paradise Poker and making a cut. My last year of college it basically paid for room, board, and education because I was making free money online.
Shaan: Did your parents know about this?
Mike: I had to kind of tell them. They were a little worried — poker, gambling, is my son okay? But my dad actually looked at me and was kind of proud. He said, “You’re kind of like the picks and shovels of it. You’re not actually doing it, you’re enabling people to do it.”
Shaan: And you said something quick before — you got to the top of Google. Did you have to do anything interesting to get there, or was it just that it was your domain name and there was no competition?
Mike: The beauty of it was there was just no competition. Nobody else was trying to misspell Paradise Poker on purpose. Maybe they’d misspell it once, but I’d have it eight times. I was the best misspeller of Paradise Poker and was literally number one.
The Kia/KN Car Opportunity [00:42:00]
Shaan: This is essentially what’s going on right now with the Kia car — Kia rebranded their logo and it looks like “KN” instead of “Kia,” so Google search for “KN car” is suddenly spiking because people see it on the road and they’re like, what is the KN car? I was thinking this feels like a Kendall thing. Kendall, what would you do with this?
Kendall: I had a buddy in fleet sales — that’s where they sell a ton of cars online — and I would make a deal with someone like that at the dealership. I’d say, look, I can get you a lot of traffic. I’d create websites that go for all the newest cars, obviously spelling it with the KN. Make a deal like, I’m going to send you these leads, I want twenty percent. And the website would just explain it: hey, it says KN but it’s actually Kia, here’s why this car is really cool, here’s a form to buy it. Send that lead over, everybody’s happy.
Shaan: How much do you think somebody could make if they did this really well?
Kendall: The problem now is Google autocorrect. Even when I did the searches myself it goes right to the actual Kia. So you’d have to find where Google doesn’t autocorrect — the app store, maybe some other platform. But when you find a really good misspelling of high-priced items with a decent margin, you could make hundreds of thousands of dollars.
Mike’s Origin: Poker Affiliate Grinder [00:44:30]
Shaan: Mike, you had a similar origin story — playing poker and then discovering the poker affiliate game?
Mike: Yeah. I was basically a degenerate gambler when I was fifteen or sixteen. My friends and I would play poker in home games. This is when poker was on TV all the time, like 2005. I just kept losing all my money, so I’d go to the local grocery store, to the Western Union, give them a hundred bucks cash, they’d send it to wherever it was going, and then I’d just lose that.
Mike: So I was like, I need to find some other way to reload my poker account.
Shaan: Not: I need to stop. Where am I getting reloaded faster?
Mike: Exactly. Then I saw they had a refer-a-friend thing on the website — they’d pay you seventy-five bucks or whatever to get your buddies to sign up. I had all my friends sign up. Same as Kendall — when I ran out of friends I was like, I’ve got to figure out a way to get strangers to do this. Ended up coming across a forum called Poker Affiliate World. A lot of people doing this, sharing what was working and what wasn’t. Very friendly community — which surprised me because we were all competitors.
Mike: Just learned through doing, started a website. I convinced my parents to lend me a couple hundred bucks to buy a domain and set up hosting. The first site I sold was probably nine or twelve months later for thirty-two hundred dollars, which was like a billion dollars to me. I got a check, cashed it, took all the cash home, spread it out. Repaid my parents. That was a very sentimental moment.
Never Having a Real Job [00:48:00]
Shaan: Did you have any actual jobs? Any kind of like “here’s your first day at the new company” experiences?
Mike: I basically had a summer temp job — they placed me different places. One was Dell warranties. And I realized then I was like, I cannot work for someone else. This is just not me. I want to work for myself, set my own hours, and make a lot of money. My mom always said when I was younger, all you said was “I want to be a millionaire.” And she was like, all right, sure, let’s see what happens.
Mike: And something like, I don’t like the idea of working really hard and someone else making money off that. I’m going to make the money off that. That’s what being an employee is — you’re making the owner’s money. I just couldn’t get around that. I was like, I need to be the owner.
Shaan: Dude, I find it hard sometimes to recruit people because I’m like, I fundamentally don’t want to do this trade where you get some security and certainty and I get the upside of your work. I philosophically don’t love this path. But then I also need to hire employees all the time.
Mike: Oh totally. And I feel like one of the most rewarding things of my company has been watching the people grow. We’d hire them, I’d say, I just need you to write a couple pages of content. They do a really good job — oh, do you want to be an editor of this website? Do you want to manage other people? The businesses I sold, I made sure the people working with me got really great jobs, because sure, I made a lot of the money, but I want to make sure their career is set and they’re in the best position possible to crush it.
Kendall’s Retirement Party [00:51:30]
Shaan: What did you do after your first sale? You did a retirement party?
Kendall: Yeah. So I had this idea — I did it, I’m done.
Shaan: And you were, what, thirty-something?
Kendall: It was like thirty-three. And I was telling all my friends: I’m going to rent out a restaurant and we’re just going to celebrate my retirement. I’ll be like thirty-three, not sixty-five, and it’ll be great. So we rented out Lazy Bear in San Francisco, had all my friends and family — it was awesome. Party bus, the whole thing.
Shaan: They didn’t even really know about your business, right?
Kendall: No. I’ve always been not one to brag. What I do is kind of just what I do. There’s no reason to be boastful. The first year after I sold the business I didn’t tell anyone. I just wanted to live with it and be comfortable with it myself. I had a three-year earn-out, so after the three years is when I did my retirement party.
Shaan: You sat on that news for a long time.
Kendall: I did. Sat on it for a year, told people, but then I had two more years left with them. Once I was done I was like, it’s retirement time. Let’s do it.
Mike: I can’t remember why I didn’t come to the party, but I do remember when he did sell that one — I had left the gambling space and I was in Dallas for something. I went over to their hotel room and him and his wife Tess had a bottle of champagne — they’re like, we’re going to open this and celebrate. I was like, oh congrats, that’s awesome man. Then I went home, Googled it, and I was like, oh. And I texted him: I really mean it now.
Selling Twice: The Containing Media Deal [00:55:00]
Kendall: That one sold for — I think it was forty-five million.
Shaan: It was actually fifty million total. You kind of sold it twice?
Kendall: Yeah, which was kind of weird. The first time I sold it for like fifteen million plus a bunch of equity. At that time New Jersey was big — it was like the first legal state with casino and poker. We focused on that, did really well.
Shaan: Let me explain the context for people who won’t know. You go from online poker, then online poker collapses because the US shuts it down. Most people went offshore or international. You did something different — a non-obvious pivot. The whole United States, and one state was going to legalize gambling. That didn’t sound big. Most people didn’t do that. What was the search term you wanted to rank for?
Kendall: “New Jersey online casino” was the big one. And you’re right — all my competitors were like, we still have forty-nine other states. But the regulators at that time said, if you choose to promote in New Jersey, you cannot do anything else. They didn’t want offshore mixing with the legal regulated market. I was like, that’s perfect. I want to be a big fish in a small pond.
Kendall: The business was going well, but there was one competitor — Chris Grove — and he was really good at content. I was more into the revenue side. We both talked for a while and realized: we’re the only people in this market. If we combine, we basically own this market. So it was an easy decision. Then you have pricing power — otherwise you’re an affiliate at the whim of your affiliate partners. They can change the price on you. But if you become almost indispensable, you’re like, I’m the only acquisition source for customers, so this is the price I’m comfortable at.
Shaan: How much were you getting per player?
Kendall: A thousand dollars per player we sent through New Jersey online casinos. The first month we partnered together, we both made way more than we did apart. Within two years, Containing Media came knocking — they said they’d heard we were the biggest and they had to buy us.
Kendall: They buy it once, it’s just New Jersey. I told them, we’re not gonna sell unless — we have forty-nine other states that will eventually legalize. So I came up with the idea: sell you New Jersey, and for any future state we’ll be fifty-fifty partners. They said sure. They weren’t really thinking about sports betting being legalized yet.
Kendall: We started running it. Three years in, sports betting actually got legalized, and the business started booming. Ten states coming online. The company came back and said, we cannot give you fifty percent of this — this is too much. So we negotiated, and it was part stock, part cash — in total around fifty million.
Shaan: And that company is publicly listed?
Kendall: Yeah, on the Swedish Stock Exchange.
Mike’s Big Win: Building JM Bullion from a Basement [01:03:00]
Shaan: So that’s Kendall’s big win story. Let’s do Mike’s. How does one go from losing money in poker to owning a company that does billions in gold sales every year?
Mike: Basically, I was in the gambling industry like Kendall was. When everything fell apart I sold — I was further into it at that point. I sold for five hundred sixty-five thousand. I was nineteen.
Shaan: Nineteen. You dropped out of college?
Mike: I mean, I’m going for it. I figured out life. So I was like, I can do this affiliate thing in any space. I tried a bunch of different plays. Dating space. Selling business cards online — that was a complete failure.
Shaan: Was that around the time of the brosicingbros.com thing?
Mike: Around that time. So there was this trend of icing people — presenting someone with a Smirnoff Ice and they’d have to get on one knee and chug it. Me and my buddies thought it was hilarious. I somehow ended up reaching out to the guy who ran brosicingbros.com and made a deal to buy it — gave him twenty-five thousand dollars. There was no monetization at all. I just thought it was cool, it had a lot of traffic, I could figure something out.
Mike: I tell my buddies, we’re psyched. And literally the next day I got an email from Smirnoff — we were infringing their trademarks. Take all the pictures off the site. The point of the site was the pictures. So I basically shut it down after twenty-four hours.
Shaan: Didn’t you try to blur the Smirnoff labels?
Mike: I talked to the prior owner and he was like, well, you could try blurring it. Doesn’t seem a little coincidental that this happened right after you bought it, like maybe he called them?
Shaan: But you’re Teflon — you’re not really getting humbled here, are you?
Mike: It was kind of a two-year period where nothing was working. I had left school and my parents were very much against that decision. So it was a dark time. Is this going to work? Am I going to get egg on my face and have to go back to college?
Mike: So one of the guys I knew from the poker affiliate world was doing some affiliate websites in the gold and silver space. There was this company that had just spun up an affiliate program. He was like, you guys should look at this. I decided to invest in this guy’s business — his name was Jonathan — and I was going to help him build these sites. Over six or nine months we built up some traffic. It was making like five grand a month — a side thing for me.
Mike: And then out of nowhere, the company we were sending everybody to just killed their whole affiliate program. We went from making five thousand a month to zero.
Shaan: Mike gets iced again.
Mike: Yeah. My partner and I had actually gone to that company and offered to sell them the website — hey, this thing was sending you two hundred buyers a month, just give us forty grand for it. They never replied. So we had no path to monetizing, and I was writing it off.
Mike: Then my partner said, “We should just sell this stuff ourselves.” And you can imagine how much of a nightmare that sounds like if you’re an affiliate. You never talk to customers, there’s no employees really, it’s a very simple business — you’re a middleman. There’s no product. But he said, “I’ll do all the inventory, shipping, customer phone calls, all that stuff. You just help with traffic and put some more money in.”
Shaan: Beautiful.
Mike: So I was like, all right, let’s give this a try. Credit to him — it wouldn’t have happened if he hadn’t pushed so hard.
JM Bullion: From Basement to $100M+ [01:10:00]
Shaan: So this is Jonathan. And JM is Jonathan and Mike. But a funny thing — you named it with your initials and had no idea that one of the largest refiners of gold and silver in the world is Johnson Matthey, so you accidentally got a boost because people thought you were their retail arm.
Mike: We didn’t get any cease and desist, so that’s nice.
Mike: We spin this thing up. It went live October 2011. The idea was just to point all our old traffic at the new e-commerce site. And it was crickets. I don’t think we got an order for three weeks. I honestly think it was my mom’s friend who went and did it.
Shaan: What’s that conversation like three or four weeks in?
Mike: There was no office — my partner had all the gold in a little dresser drawer in his basement. So you’re in the basement and the gold’s not leaving the drawer right now. But I wasn’t really worried at that point. You know, it takes time. You’re doing the right thing.
Mike: Kind of a funny story on this — we eventually out of nowhere start getting big orders, and we didn’t change anything. Confused as to what’s going on. Big credit card orders, repeat customers over and over. We’re like, we’ve hit it, this is going to work. Two months of this, we’re probably doing thirty to fifty grand in revenue a month.
Mike: And literally on Christmas morning my partner texts me: “Kind of weird, have you seen the checking account?” I go pull it up on my phone. Both checking accounts were negative forty thousand dollars. All of it was fraud — every single order was credit card chargeback fraud. We just didn’t know anything about any of this stuff. So we had so many of those moments along the way. Two kids figuring out how to run a gold business.
The Honest Look in the Mirror [01:14:30]
Mike: So I recover from that. Put more money in. I was pretty much on the ropes. That was it — this was going to work or I was stressing.
Mike: The really turning point was: I just took an honest look in the mirror. Here’s JM. Here are the five biggest companies. If I look at their websites, their pricing, product selection, shipping speed, customer service — I basically did a little scorecard for everybody and I was like, there’s no reason anyone would ever buy from us. We’re worse at everything. We had less selection, we were so small we couldn’t get a wholesale account, so we were just buying from the cheapest retailer and marking it up. Me and Jonathan were answering the cell phone — that was our 800 number. Why would someone buy from us?
Mike: So what I landed on: the only lever we can really pull is price. This is a commodity. It’s like buying gasoline — if there’s a store here and a store there and that one’s a penny cheaper, you’re going to pull in. Let’s just undercut everyone. If we can get volume I know we’re going to be able to figure out margin as we go.
Mike: We did that and it worked. Through 2012 we were doing a million-plus a month in sales. The problem was it was super capital-intensive because you had to stay ahead of inventory. So I put in my last hundred grand and then we outgrew that. No bank was going to give us any money. We put a deck together, sent it to like sixty different angels or VCs — zero responses.
Shaan: So you called Kendall.
Mike: Yep. We were competitors in the space, went to all the conferences together, went out for dinners. We were friends. He’d told me after I sold my gambling business: whatever you do next, let me know, I’d like to invest.
Kendall: I was excited about being able to be a part of it. I was like, if anyone’s gonna figure it out it’s going to be Mike. So I invested, and it was maybe a twenty-four hour negotiation.
Mike: He had all the leverage — we were either going to go under or he was going to write the check. He did a great deal.
Kendall: It was affiliate speed. We had a handshake agreement and then he just wired the money.
Mike: It was a hundred thousand. And then Kendall did another great A-plus move — he negotiated a rider that said he gets to do another fifty thousand at that same valuation at his option. Which he then did a few months later.
Shaan: So you put in a hundred fifty thousand total. And what’s your return on that?
Mike: It sold at around twenty million from what I recall for his piece.
Kendall: Around there.
Shaan: So you turned a hundred fifty into maybe twenty million?
Mike: Yeah.
Shaan: That’s amazing. Do you want to do another business together? I’ll actually help this time.
Growing JM Bullion: Capital Crunch and Credit Card Fraud [01:20:00]
Mike: So we get his investment. Three months later we have the same problem again. We were up to about four million a month in revenue and it was starting to hockey stick. The SEO was really starting to kick in. Initially it was just pricing cheaper to make us more appealing, and then the return customers came, we got the backlinks, the site was growing.
Shaan: What do you call that exercise you did — I took an honest look in the mirror and said, why would a ten want to date me?
Mike: Yeah, that’s basically it. Why would they be choosing us? I feel like more companies should do that exercise. The mirror doesn’t lie, you know. The world isn’t wrong and dumb. That exercise forces clarity on where are you going to be great. We decided: price first, then everything else later.
Mike: So the business grows, grows, grows. We do this for eight years. We sell. The problem was it was super capital-intensive — and then our credit card processor throws us out. That was like half our revenue. It was a Visa thing — we were growing too fast, they needed a big cash reserve to work with us. They asked for our financials, a P&L and a balance sheet. We didn’t even know what a balance sheet was. So unsurprisingly they threw us out.
Mike: I had to go back to Kendall, hat in hand. “So this happened. Are we still going to do this?” And he was just totally calm, like, we’ll figure this out. Still cut the check. There were probably ten more of those moments along the way that he just helped me think about things in the longer increments.
Shaan: Because with crypto right now — people would have said it’s impossible to sell the Milk Road during this time. With a good deal you can sell anything. But it’s impossible to get a good deal right now. That’s conventional wisdom. And I hate anything that’s like conventional wisdom because I’m in the outlier business. Creating a successful startup is an outlier. So I don’t really need advice about what general outcomes are. I need advice on how to create outlier outcomes.
Shaan: So I was like, okay. Crypto industry gets shook. Big companies have to freeze. They can’t make a flashy acquisition right now. That’s one filter. Then: who’s going to say, bad news in crypto, maybe I shouldn’t do this? I need somebody who’s got long-term conviction, who thinks in five-to-ten-year increments, who believes in the fundamentals, and understands that during the downturns is when you make acquisitions. This is the time to play offense.
Shaan: And that’s how we ended up finding basically the perfect partners at that time.
The Ripoff Report Scam and Other JM War Stories [01:28:00]
Mike: All right, here’s a story that was a mix of good and bad. That first year before Kendall was in, we got an order for twenty thousand dollars — which was a big order for us back then. The guy pays, we ship it, it’s delivered, everything’s fine. Then we hear from him a week later: “I was out of town, there’s no gold here, I don’t know what happened.”
Mike: We were so naive we didn’t even have shipping insurance. So we dug in firm — UPS has the GPS coordinates on your doorstep, the driver signed an affidavit that he delivered it. But this guy just kept digging in harder. And then he went on ripoffreport.com — anybody can file that hey, this company screwed me. He did that, and we were so early that when people searched “JM Bullion” that was the number one result. Our sales fell off maybe thirty percent because everyone in the gold space checks reviews — they’re always worried about getting scammed.
Mike: Then he went into this sob story: that was my kid’s college fund, my kid’s not going to be able to go to college, you’re going to ruin his life unless you make this right. I was really starting to stress. I drafted the email where I was going to personally write him a check for twenty thousand — which would have wiped out my checking account. But I decided to sleep on it one more night.
Mike: That morning, I woke up and UPS had gone with the police to his house. As soon as the police were there, he found it in his closet.
Shaan: Happy ending.
Mike: Happy ending. But another warning moment — obviously we need to figure out delivery and insurance.
Domain Hacks: Facebook.com and the Switc Story [01:33:00]
Mike: I had another one — facebook.com. So at the time it was thefacebook.com and I knew right away when they dropped the “the”: I’m going to domain-squat on things people are going to type wrong. Same as Paradise Poker. So facebook with a “k” — the k is by the m on the keyboard, so you type “faceboom” or whatever.
Mike: The crazy thing was I got to see basically Facebook’s hockey-stick growth through traffic. At the time you’d just have PPC text link ads, you’d make like ten cents per click but there was enough traffic where it was worthwhile. I sold faceboom.com for like twenty thousand.
Mike: Then I tried to sell facebook.com — with the k — but a big packet of papers came from Facebook. “Hey, that’s our trademark. Do you want to fight this or hand it over?” Very easy choice.
Shaan: At least you got to sell one of them.
Kendall: And I had one too — I almost went blind. Not twitch.com but I twitched it — switc.com or something like that. Anyway. My first big company, you know the regulator said you can’t do offshore if you’re gonna do regulated. And one of my competitors, I think, told on me. So I’m at an industry conference and one of the regulators was like, “Hey, I’d like to meet you for coffee.” I was like, is this something I should be worried about? He’s like, “No, no, just come.”
Kendall: It’s like when Chris Hansen says the pizza’s inside and invites you in. You don’t go for the pizza.
Kendall: So I walk up, we sit down, and he says, “So we can do this the hard way or the easy way.” I’m stunned. He tells me they’ve had reports I’m doing offshore stuff. At that time I’m like, I’m not going to say anything, I’m not going to incriminate myself. But it was wrong — there were pages algorithmically updated with offshore ads that I had no control over. He didn’t know about domain parking pages and all that.
Kendall: “I need to talk to my lawyer.” Then I get an email from them: “We need you to come to New Jersey.” I was like, oh no, they want to arrest me. They want to get me in their jurisdiction.
Kendall: At the same time I was telling my wife Tess, I’m seeing spots. She’s like, oh, it’ll be fine. But it got worse and worse. I couldn’t read a menu. I went to a specialist and he thought I had a detached retina. He looked harder and said, “Actually, have you been stressed lately?” Very stressed. He’s like, yeah, this is a stress thing, you’ll be fine.
Kendall: To end the story: I had to go to New Jersey to talk to the regulators. I wanted to bring a lawyer and they told me — do not bring a lawyer because we’ll make it hard on you.
Shaan: Oh they told you that? Man, I wouldn’t know what to do. Is this a good-cop ploy? Are they pushing me around? Or is this real?
Kendall: Had no idea. But I listened this time. And when I sat down it was actually this super cordial conversation. They wanted to learn more about affiliates because they were the first regulators in the United States and had never really talked to a large affiliate. So they just wanted to do a fact-finding mission. It all worked out. I didn’t go blind and I didn’t go to jail.
Shaan: You were either going to be blind or in jail, and you ended up neither. Did you pack a jail bag?
Kendall: I did not, but my wife was in a hotel room with enough clothes in case.
Lifestyle Design: Twins, Chefs, and Optimization [01:43:00]
Shaan: You guys are also kind of like life-hack experimenters. You find the clever angles in business, and you do the same thing with life. You don’t just do things the way others do — you’re like, well, why don’t I just do this? Tell us about some of those. What are some things you guys do in your day-to-day life that isn’t standard?
Kendall: I think the first one for me was: we were having twins. I was telling my wife, we need to get some help, we need experts. I talked to an agency and cast my net wide. I was like, I want to find someone who has done this before and can make our lives easier. I found this twin expert — she actually lived in New Jersey — and we hired her for four months.
Kendall: She worked with them night and day, eighteen hours a day, and part of it was training us. You know how with a dog they say you don’t train the dog, you train the person? Same thing with us. She put them on an insane schedule — if one was sleeping the other was sleeping, if one was eating the other was eating. After four months they slept through the night and were totally schedule-oriented. We’d look at the time — two o’clock, they need to eat right now — and they were just ready. Both of them at the exact same time, always. That made life so much easier.
Shaan: Basically one kid that ends up being two.
Kendall: Exactly.
Mike: After he sold, one of his splurges was he hired a chef. I cooked for him and when I heard that I was like, that sounds really bougie, I don’t know. But then he was open about it and I was like, yeah, this makes a lot of sense. I can eat healthier. I don’t have to think about it, I don’t have to think about what I’m going to eat. So I ended up finding somebody as well.
Mike: And I’ve come out to see him a few times over the last few months. When we’ll be eating I can see him looking at me because he’s so competitive — I know he wants to know: is this better than what I’m eating at home? Sadly the answer is yes. But I’m never given that satisfaction.
Kendall: That’s messed up.
Shaan: You’re a foodie and that makes sense. Mike, you’re more of an efficiency guy — you don’t really realize how much mental and physical energy goes into feeding yourself three times a day. Or in my case, kids also. We have a chef as well. If I just don’t have to make decisions, eat healthier, it tastes better because I’m not good at cooking and this person is — any money I could spend on a nice car I would way rather do this. I’d rather have one less employee at work and do it myself than sacrifice on this.
Mike: For sure. And I think we’ve both gotten a lot better at: if you have a problem, you can think about how to fix it tactically, or you can think about who can fix this for me. That path is so much more efficient. You can focus on your superpower.
Self-Funded vs. VC: Their Philosophy [01:49:00]
Shaan: You guys are different from most people I hang out with here in San Francisco. Tech is not what you guys do — you make WordPress sites with referral links, basically. It’s not a software startup in the same vein. And you don’t go raise money from VCs. You don’t do a lot of the Silicon Valley stuff. What do you like about your way? And what parts do you look at VC and think, maybe I should do some of that?
Mike: For sure. I grew up in Buffalo, New York, and was never exposed to any of that stuff. I didn’t know what I didn’t know. But meeting you and spending more time out here has opened my eyes a lot to that world.
Mike: The benefits of finding it ourselves are obvious: we control it. No one else is asking, where’s this revenue target? We can think really long term about the business. We’re the decision makers and we move fast. Decision needs to be made — hey, what do you think, here’s what I think, all right, let’s go.
Mike: The one thing you probably lose is it’s harder to have the really big outcome. It’s hard to be a ten-billion-dollar company going that route. With VC it’s still very rare, but it does happen. And you lose time — we always wanted to operate efficiently and profitably, so things would take time. You’d watch a competitor raise a bunch of money and do exciting things and you’re like, that’s really cool, that’s not me right now.
Mike: But I’ve always been a control freak. I don’t want to work for someone else. With VC it’s kind of the same thing. With this acquisition I feel like you’re on our team. You’re going to be on the board and we’re going to be able to make really big decisions together rather than, hey, I invested in you, are we ten times yet?
Shaan: Yeah, totally.
Business Philosophies and Operating Principles [01:54:00]
Shaan: I’ve heard some of your isms — Kendalisms, Mikeisms — as we’ve been talking. Nobody goes through years and years of building businesses without coming up with some operating philosophy. Do you guys have any that stand out? Pillar ones you can tell a story around?
Kendall: For me: you’re going to be right a couple of times in your life, and if you think you’re going to be right, swing big. For example, with Bitcoin — I saw it in 2013. I was like, this could be really cool, or it could go to zero. But I had this inclination that it could be way bigger. It brought me back to my dad in the nineties. He was a computer programmer and was telling our family that domain names were going to be big — every person or company is likely going to want one. He bought our last name, seville.com, but didn’t really buy anything else. He could have bought poker.com. He was right but didn’t swing hard.
Kendall: So when I was looking at Bitcoin I was like, this is my domain names moment. I just started buying and said I’m going to hold it no matter what. What price was it at?
Shaan: Around eighty to ninety dollars per Bitcoin.
Kendall: I put in a couple hundred thousand dollars at that point. I was like, I’ll just wait it out.
Shaan: Did you feel tempted to sell? Either because you had a bunch of profit, or bad news was hitting and you thought maybe you should get out?
Kendall: Not really. When it was really high you think about taxes. And when it’s low I’m still like, it’s got a long ways to go. I’m just on a long hold.
Shaan: I discovered Bitcoin around the same time. My average buy price was around four hundred. Bitcoin runs up to three thousand, I go to my cousin’s wedding, and my Indian auntie — not someone I would ever expect to say the word “Ethereum” — says, “Oh yeah, Bitcoin’s very good.” I’m like, what? And I immediately knew: if she’s on the trend, it’s over. So I went to Coinbase and tried to sell everything. But Coinbase had a limit on how much you could sell at a time, so I maxed it out one week, did it again the next week, and then the fear just kind of dissipated. Bitcoin runs to twenty thousand. I’m the biggest idiot. Then it crashes back down and I’m like, I really need a plan. Am I holding this forever? What is driving my actual belief in this?
The Bitcoin Thesis and Crypto’s Hard Case [02:02:00]
Shaan: We’re at a point right now where sentiment about crypto is probably at the lowest it’s been in a while. For a lot of people this is their first real crash. What is your belief in crypto based on?
Kendall: I feel like digital money needs to be a thing. We were literally trying to wire money into this company and it wouldn’t work.
Mike: I had the real issue there. We use the same bank — Citi — and sent the same wiring instructions. The next day Mike’s wire hits and mine never does. I answer all the questions, do the DocuSign, respond to all the text auth stuff, and it never comes in. So I reach out and they come back and say the wire instructions are wrong. Meanwhile Mike sent the same PDF from the same bank.
Mike: On crypto that would have been a ten-second transaction.
Kendall: I agree with him. I’m probably even more into it on the don’t-love-government-control-over-fiat-currency side. We’re starting to see the ramifications of that — debt, inflation, those kinds of things. Having another option is nice. In the same way: if you don’t like the way your government manages the money system, you can opt into a different monetary system controlled by source code. Anybody from anywhere in the world can say, I don’t like my country’s monetary system, I’m going to opt into this one.
Shaan: What would you say is the steel man of the case against crypto? The best argument someone could make against it?
Mike: I think a big one is: there are a lot of scammers in the industry, and they’re able to do that because they don’t have the checks and balances of the current system. You can’t really argue against the fact that crypto looks really bad a lot of the time. But then at other times it looks really good. It wasn’t Bitcoin that did something bad. If somebody runs a real estate scheme and scams investors, it’s not real estate that was the scam — it was the scammer. Crypto just has such a playing field, and it’s a money business, so so many people can scam. It almost associates Bitcoin itself — which is like a rock, it’s not doing anything — with the scam. Even though it was the human being who decided to trick people. That’s the hard thing to disentangle.
Shaan: What was your reaction to FTX?
Mike: I was stunned. I, like a lot of people, viewed them as almost a blue chip — rock solid. If you didn’t feel good putting your money on Coinbase, I would have recommended FTX to anyone. Really shocked. Same with Genesis. I actually have money on Genesis that I don’t know what’s going to happen to.
Mike: But it’s been interesting for the Milk Road businesses. This has actually been good for growth. We cover the news and there’s been a lot of news. We’re seeing record subscribers, reader scores are really good, people are very interested in following this even though it’s been so negative. That’s another piece of why we liked your business — it’s less correlated in our minds directly to crypto prices.
Wrapping Up and Where to Find Them [02:12:00]
Shaan: Amazing. Do we leave anything out? Any good stories we should have covered?
Mike: I don’t think so.
Kendall: Nothing.
Shaan: All right. Where should people find you guys? Mike, congratulations — did you tweet for the first time today?
Mike: I had my first tweet today. First tweet ever. About the Milk Road acquisition.
Kendall: And last night it was like the news is going out, and Mike’s like, “Hey, can anyone help me figure out how to tweet? I’ve never tweeted, let alone a thread.”
Mike: Yeah, Ben helped me out, but it was kind of a show. He sends his out this morning and I misspelled Milk Road.
Kendall: He deleted the first tweet and didn’t realize it for like twenty minutes. Everyone’s like, what is wrong with your Twitter profile?
Shaan: You know what, I think you should keep the no-picture, no-tweets persona. Your bio should be: “I don’t tweet. I do actual work.” And everybody should follow that. That’s your whole persona.
Kendall: That actually came to mind when you asked earlier why we don’t do social. Do you remember back in the poker affiliate world, all the mid-tier to small affiliates had their personal blogs? Everybody was musing about what they were doing in business. And then we were at one of these conferences, and the biggest poker affiliate in the world — this very private guy we can’t name — never did any of that stuff. Every night we’re out at the clubs hoping he’ll give us his table drinks. And it was kind of eye-opening. I’m like, there’s probably a correlation here. Maybe I should do the work.
Shaan: Can you tell any of his stories without naming him?
Kendall: Sure. He grew up very poor, had to leave school in eighth grade to work at a hotel or something. First big thing he did was become a massive eBay power seller, selling CDs. Then he was smart about rolling up smaller affiliates — he had better deals with the operators, so he’d buy someone’s site for what they thought was four times earnings, but with his payment terms it was actually two times earnings the moment he signed. He could just buy these all day without having to come up with a genius idea to grow them.
Mike: He bought my poker affiliate business back then. And he was really helpful at JM too. One thing he helped me with a lot was: I would ride the wave of emotions hard — one day it’s a hundred-thousand-dollar day and I’m ready to IPO, the next day chargebacks hit and I’m on my deathbed. He used to joke with me, “If we were publicly traded and you set the stock price, it would swing like a thousand percent a day.”
Mike: He helped me zoom out and think in five-to-ten-year increments. Framed like that, nothing really ever seems like that big of a deal. There are very few things that happen to your business that are going to materially change your trajectory over five to ten years.
Mike: An example: before he put a million into JM, shortly after Kendall did his first angel investment — like a week before it was going to close, all documents ready to sign — our credit card processor threw us out. That was half our revenue, gone. It was a Visa network thing. They asked for our financials. We didn’t know what a balance sheet was. So unsurprisingly they threw us out. I had to go back to him hat in hand. And he just said, totally understand if you’re out, but if you’re still in, we’ll figure this out. He still cut the check. There were probably ten more moments like that where he just helped me think longer-term.
Milk Road Is Hiring and Final Thoughts [02:20:00]
Shaan: And one thing I should say — Milk Road is hiring. Looking for A-players who have done it before, because we want to scale this as quickly as we can.
Shaan: I actually want to say: when we were looking at this deal, we had a higher offer that we turned down. One of the reasons I told Ben was: I went to your Twitter feed and saw your tweets from way back that were like, “Crypto Punks are cool.” I looked at the date, looked at what the price was then, and you were ahead of the curve. And then you had another one about getting into a certain exchange early. I’d been trying to get into that exchange myself.
Shaan: I feel like if I just hang out with these guys more I’m going to get more value out of something completely unrelated to Milk Road. There’s going to be some random thing. I’m a big believer in that — if you find exceptional people, you don’t have to have a plan. Just hang with them. Find some routine or value exchange where you’re going to be in each other’s orbit, because something good is going to come out of that.
Shaan: Similarly, if somebody wants to work at Milk Road — the same reason I wanted to sell and work with these guys is the same reason anybody should want to do that. If you heard the stories on this podcast, you’re probably thinking, God, these guys are awesome. They went through a bunch of stuff but they figured it out and they play their own game. Those are the type of people you want to work with, even if you someday want to be more entrepreneurial. If you get a job in direct proximity with people like that, it’ll change the way your brain works.
Kendall: For sure. You want to get in shape? Hang out with fit people.
Closing: The Body Fat Challenge and Going Uphill [02:23:00]
Shaan: What was the body fat challenge? Did you win?
Kendall: So I’m in a group called Entrepreneurs Organization — a forum with seven other Dallas entrepreneurs. We meet monthly, do a retreat once a year. In advance of the retreat, everybody sets a fitness goal and puts in five hundred bucks. If you hit your goal you get it back. If you don’t, it goes toward funding the retreat.
Kendall: So maybe three months out, everybody sets goals. I thought I was fifteen percent body fat and said I’m going to get to ten. Slammed it down on the table: boys, I’m doing it. I work really hard the next two months. A month out I’m like, I’ve got to be at eleven, I’m almost there. I go get a DEXA scan. I was fifteen-point-seven. I was nowhere near where I thought.
Kendall: Then I really killed myself that next month. Got down to about twelve. But lucky for me some of the guys didn’t schedule DEXAs and were using those scale things instead. On the scale I was like eight-something. So I got my five hundred back.
Shaan: The reality is you did not hit your goal.
Kendall: Yeah, but technically… Next year I’m gonna get it.
Mike: What I would have done is figured out what I was at, set my goal one percent under that, and just make sure I win.
Shaan: Mike wants to make his life hard and go uphill.
Mike: Last year everybody at the table did a weight loss thing, so I thought that was what these were. I set a goal to get from one seventy-eight to one seventy-five. They’re like, well what are you now? I’m like, one seventy-eight. It was essentially no goal at all.
Shaan: You guys have been slacking. You need to write a book called Going Uphill. When you’re done working you can start tweeting. Your uphill book with a picture of you going uphill on the cover.
Mike: Actually, I do have one last uphill story. So in Whitefish this year I mentioned I was doing the splitboard thing at the resort. They would open it an hour before the lifts ran, only for people going uphill — safer, not a ton of people coming down. One morning it was negative ten wind chill. They never even opened the resort that day — too windy, just miserable. I was like, perfect. Optimal conditions. I suit up and get out there.
Mike: I’m the first one on the path at six AM. Going straight up. Feeling good. I knew there was one steep section from having done it a few times. The skins would start to slip on the steep parts. I’m going straight up, the wind is blasting, ice is just terrible. And I’m one step away from the top. I take the step, it slips, and the whole thing falls apart. I’m falling backwards downhill, doing a somersault, skis go flying.
Mike: I get up to gather my stuff and realize there are like twenty people behind me who just watched the whole thing. They’re helping me out. I look up the hill because they’re starting to go and all of them are zigzagging back and forth. It’s not so steep that way. I was just going straight up the hill. I was like, oh, that’s why.
Shaan: Wouldn’t have it any other way. Metaphor of life. Awesome.
Shaan: Well, thanks guys for doing this. I know it’s a little out of your comfort zone but I’m glad you guys did it.
Mike: Thanks for having us. We appreciate it.
Kendall: Thanks for having us.