MFM #169: How One Man Has Built 5, Billion Dollar Companies

Andrew Wilkinson

It's pretty crazy! I got a chance to talk to Warren Buffett on the phone. Some guy I was talking to said, "You know, I'm trying to figure out philanthropy and how to give money away." Literally, he goes, "Oh, you should talk to Warren Buffett." I was like, "What do you mean?" Then he just CC'd me to Warren Buffett. It was one of the weirdest things that's ever happened to me, and it was amazing. I was kind of nervous; Warren Buffett's like my hero, you know? I was not expecting this. It was just a random Friday, and Warren Buffett's secretary emailed me back and said, "Oh yeah, you know, call him whenever. He'll pick up." So I called, and I got put right through. It's just Warren freaking Buffett on the phone! Basically, he said, "Oh yeah, I'm not doing anything. I can talk for as long as you want." I just got to pick his brain for an hour, and it was insanely inspiring.

Sam Parr

Alright, Sean is out with his new baby. I asked Andrew to come on and do this, and I wanted to do a special segment today called "Billy of the Week." We actually used to do these at the end of some episodes, but people liked it, and I want to do them more often. I asked Andrew to come on. We have two people who are ready to discuss, and Andrew doesn't know the format. Here's what I wanted to do: I'll go first because I think I did more research than you, but it looks like you actually did a fair bit as well. I'll go first. I'm going to tell you who I'm talking about and explain to you why they're interesting. I picked this person on purpose. Maybe you can tell me who or what other opportunities are in this space. I kind of picked someone similar to you, but the guy is probably twice your age, so he's further along in his journey. I think it's interesting to you, but we can also talk about anything else we want to discuss as we go.

Andrew Wilkinson

yeah sounds awesome

Sam Parr

Also, what's going on? How are you? Are you enjoying being the CEO or the founder of a publicly traded company?

Andrew Wilkinson

Yeah, it's interesting. It's kind of like, you know, when you start your company. It's really exhilarating. You have your first employees, you start dealing with problems, and you've never done it before. So your stress level is like 10 out of 10 when you're first doing it. You're like, "I don't know what matters. I don't know what best practices are. If I have a problem with an employee, how do I deal with it?" All that kind of stuff. It's that same learning curve. So it's incredibly exhilarating and exciting. Having a public company is like a huge milestone, but at the same time, I'm like a new entrepreneur. I don't know what actually matters, who to listen to, or where to focus sometimes. And that's just, you know, you do anything new and it's stressful. So it's been stressful for sure. But now I feel like we're on the other side of it. We're starting to figure it out, and it's been really good.

Sam Parr

Because your stock... I check your stuff once a week. Is it up this week or down, or do you not even look?

Andrew Wilkinson

I think it's kind of coasting. I try not to look at it. Yeah, it's kind of jumping between about **$650,000,000** and **$1,000,000,000** depending on the week.

Sam Parr

Wow! Our podcast has been growing a ton, and people have criticized me for not doing introductions. First of all, I'm Sam Parr. I co-host this with Sean Purry, who is now way more famous than I am because he's crushing it on content. I started this thing called The Hustle and just sold it for mid-eight figures to HubSpot. Now, Andrew is a friend of Sean and mine. Andrew, I'll do a quick introduction for you, and then you can say a bit about yourself. Andrew started this thing called Metalab, which is an agency that makes all types of amazing stuff. Using the profits from his agency, he went and bought a ton of companies and invested in a lot of things. Now, his whole enterprise does about $100 million in revenue and is very profitable. He just did a SPAC and took one of his companies, Pixel Union, which makes Shopify plugins, public. It's now at a $650 million to $700 million market cap. Did I miss anything there?

Andrew Wilkinson

Yeah, I mean, I kind of always think like I'm a designer who ended up becoming an investor, just like how Sam's a writer who ended up becoming an entrepreneur. It's been a process of just kind of stumbling into stuff. A lot of why we've gotten as big as we have is because I just don't like doing things that I don't enjoy. So, I kept delegating the stuff I didn't enjoy. When you do that a lot, in its final form, that's just investing—where you're hiring CEOs to run your companies and incentivizing them. Yeah, it's crazy! I never would have thought we would get to the size we're at now, and it's been a cool ride.

Sam Parr

And the reason I'm asking this next question is because it's related to the first story I want to get to. How many companies do you guys own or partly own? And how many have you invested in, owning like a smallest check size?

Andrew Wilkinson

So we control, as in like we have over 50-51% in, I think, 35 businesses. And then we have another probably 40 to 50 minority investments. Those would be anything from little $100,000 venture bets to minority preferred equity where we might own 10 or 15% of a business.

Sam Parr

so in the 100 range ish total deals

Andrew Wilkinson

right something like that

Sam Parr

So, the guy I'm going to talk about today is named **Brad Jacobs**—or **Bradley Jacobs**, as he might go by. We're going to call him **Brad Jacobs**. This person is super interesting because he has started five companies that have either gone public or are worth over **$1 billion**. He started at age 23, and he's 64 now. Google him: **Brad Jacobs**. He's worth somewhere in the range of **$3 to $5 billion**. He doesn't invest passively like a venture capitalist; he actively buys companies. He's bought something like **600 to 700 companies** across a variety of industries. He has used the same strategy over and over again in different sectors, which is incredibly interesting. This guy is very fascinating to me for a variety of reasons that I'm going to explain. But, Andrew, have you heard of this guy **Brad Jacobs**? Do you know anything about him?

Andrew Wilkinson

this guy I don't know anything

Sam Parr

that's kinda why he's cool he's kind of on the under the radar if you Google him he's he's got like a bald head and he looks like a finance guy because he wears a tie and he's like pretty well spoken and you think that he's just like a private equity person and I guess maybe he is but he's really an entrepreneur he's very entrepreneurial and he's far more interesting than just a lot of the typical new york hedge fund y type of folks and so I'm gonna give you a quick story about his background so he started 5 things that have been quite meaningfully sized so the first was it was called amarex oil associates he started it when he was 23 and it was an oil biz it was basically like an oil brokerage firm which I'm not entirely sure what that entails but I imagine it just means connecting folks who created the oil to large businesses who are buying the oil and within a very short amount of time only about 4 years remember he started this when he was 23 so by the age of 27 amarex his oil business was doing $4,700,000,000 in gross gross oil bookings meaning he would that's how much oil they're buying and and selling now I imagine his company kept a tiny% of that like 1 or 2 or 3% but incredibly impressive for a young guy and after a few years he sells that business for a $1,000,000,000 then only a couple months after that he starts this thing called hamilton resource hamilton resource he starts it out of england he convinces a french bank to give him a $1,000,000,000 line of credit which he was quite successful already even though he was crazy young but he made it happen and he went and secured a a line of credit and here's what he said he goes we moved physical cargoes of oil from one place to another the eighties turned out to be a great time in the oil business and I built hamilton up to about $1,000,000,000 in revenues and did business in dozens of country dozens of countries before I moved back to the states in 1989 so between 83 89 he started this business and it also was huge I believe he ended up selling it for a $1,000,000,000 north of a $1,000,000,000 so that's business number 2 business number 3 a little bit of a of an odd one was waste management I don't think there's anyone out there doing waste management stuff now that's brand new but there's a ton of companies that at the time started in the seventies eighties nineties like waste management the company waste management and what they did was they would go out and find tons of mom and pop waste management companies because back then that's how it was and probably is a little bit to this day but he started this thing called united waste management which eventually became the 5th largest solid waste business in america and it had a very very very simple business plan which was buy landfills in small markets buy many of the local trucking companies that were serving those markets optimize the truck routes maximize the pricings get margins up achieve size so that they have the capability to scale and they did that and the strategy worked really well and in just 5 years our earnings compounded annually by 55% and the and he took the company public something like 8 months after starting it and the stock price went up as well 50% every single year for like 5 years eventually that company grew to $3,900,000,000 in revenue and $1,200,000,000 in ebitda with 750 locations and 13,000 employees is this freaking crazy oh sorry that I just gave you the numbers I gave you the numbers for his next business but the waste management grew to $2,500,000,000 in revenue oh sorry $2,500,000,000 in in exit to waste management nuts right

Andrew Wilkinson

That's crazy! So, I always think there are four different types of entrepreneurs. First, there's the **innovator**. Let's take Chipotle as an example. There's the guy who rolled the first burrito and was like, "Oh shit, this tastes really good." Then, there's the **remixer**. This is the person who creates Chipotle. They take the burrito, package it up, and create a brand around it. Next, we have the **scalers**. This is the person who scales Chipotle to 100 locations. Finally, there's the **optimizer**. This person just sits on top, makes sure it doesn't blow up, and gets as much juice out of the lemon as they can. This guy is a great example of a scaler. He takes something that already works, something that's already proven, and just does a much better job of it. He rolls it out, makes it scalable, and builds something massive. It's super interesting because I'd say I kind of fall into this camp. At the same time, I feel like what's sexy about this guy is actually how boring the businesses are. They're so basic; these are things that are like **undisruptible**. When you build them, it's like a 100-year business or something, which I think is really cool. Whereas what we do is think in 5-year chunks.

Sam Parr

I completely agree. If you scroll up to this document that we have open and click "source," you'll see the source that I'm using for a lot of this. This is so interesting. We're on business number 3. I'll get to 45 in a second, but what this guy does—and then when I wrap up all 5, I'll explain to you what my lessons learned from this guy are. I'll say one of them right now: what this guy does is he raises money like a madman. It's not like a ridiculous amount. I mean, saying you're raising tens of millions of dollars, I guess for the average Joe, yeah, that is a ridiculous amount. But he's got a track record and he turns them into multibillion-dollar ventures. So, tens of millions of dollars is not that much money. But if you click that source thing, what does that take you to?

Andrew Wilkinson

to the sec

Sam Parr

Okay, I found this file on the SEC, and I don't really know what this is. I don't even remember how I came across it, but this is what interested me. It's a Q&A session of him having written it out, and he basically lays out the strategy of his fourth or fifth business. So, what this appears to be is a Q&A that he prepared, and they showed this to a ton of potential investors— a ton of potential banks. They decided to invest in him, and I think this was before the company even started. Is that what that is?

Andrew Wilkinson

So you're saying this is what he raised on? Like, there's no deck, there's nothing. It's just this is the thing. He goes out and he says, "Read this document and you can invest."

Sam Parr

I'm not entirely sure, but I think that is part of it. This is called the Schedule 14A, which I’m not an expert in regarding the SEC. I believe that is something you have to answer before a board of directors at a publicly traded company when it raises money. But it's interesting, though, because he writes in wonderful, straightforward, simple English. You could read his entire strategy, which I'm going to go through in a second. But skim that while I summarize the next two businesses that he did. So, he started— I told you he started two oil businesses, but those were oil brokerage businesses. Then he started a waste management business. Now, his fourth one is called United Rentals. Now, I don't know if you see this in Canada, but if you pay attention to this now, and if you're listening to this and you live in America, go on a drive in downtown wherever you live. Look at the big box trucks and look at the rental equipment. So, look at things like the Caterpillars, the Bobcats, or the construction equipment, as well as the portable potties and anything involving construction or trucking. Go and look at those things, and I guarantee you, on a lot of them, you're going to see United Rentals. Well, that is the fourth company that he started, and he started it with the idea of the same thing as waste management. He wanted to find a massive industry that was highly segmented by small businesses that were profitable and great, but they didn't have enough capital to grow, and they were kind of bad at sales. And that's what he did. He founded it, and in just five years, it grew to $4 billion in revenue and $1.2 billion in EBITDA.

Andrew Wilkinson

Is he growing via acquisition, or is he just rolling this out and crushing competition across the country?

Sam Parr

We're going to talk about that, but what he said was, "We got there partly through acquisitions and partly through organic growth developed by developing greenfield locations." He goes on to say, "We grew by using the same strategy at United Way." So, we bought about two-thirds of the branch locations and cold-started another third from scratch. I actually prefer cold starts, is what he said. The business plan for United Rentals was to become the largest equipment rental company in the world and leverage our purchasing power, branding, and other advantages of size. Within 13 months, we became number one, leapfrogging Hertz, which had become the number one equipment rental business in 1965. Another thing we did was we went fast. We went public fast. We formed the company on Labor Day weekend, and we were trading on the New York Stock Exchange by December. Labor Day weekend is in May, I think, right?

Andrew Wilkinson

mhmm

Sam Parr

So, they started the company in May, and five months... is that six? Seven months? That's seven months later they were public. Merrill Lynch said it was the fastest growing, or the fastest IPO they have ever seen. I stepped down, and he stepped down from United Rentals in 2007. This is only five years after starting to start the next company. But when he stepped down from United Rentals, if you look it up now, I believe their market cap is $25,000,000,000. So, he spent five years on this company, and it's worth $25,000,000,000. It's crazy! So, listen to what he did after this. After I stepped down, I began looking for my next big thing. I studied tons of industries, and I ended up concentrating on transportation and logistics. It's larger and more fragmented than the industries I've previously been involved in. It's a $13,000,000,000,000 industry. And here's what this guy says. This guy, at the time, is already a multibillionaire. But let me see if I have... he wrote out what he does, which was basically he spends three months reading tons of reports. Then, he calls 100 experts in each industry, and he just goes and sits down with them and asks them questions. It might as well be a podcast. That's exactly how he learned. So, he's this multibillionaire, he's this big shot, he's done all this amazing stuff, and he calls these people and just sits down and listens. That's all he does. It's pretty amazing. And he did this, and then he's in this with his new thing. It's called XPO Logistics. Have you heard of this?

Andrew Wilkinson

I have heard of this. I think it's a delivery and logistics company, like a competitor to FedEx. At least, that's my understanding.

Sam Parr

Well, we'll put this in the show notes, but in that document up top, that is the document from where he was raising money for XPO Logistics. In plain English, it...

Andrew Wilkinson

Looks like it's about the supply chain. It's about getting people the things they need that are critical, on time.

Sam Parr

well in there he in that document that I sent to you he I didn't I I I couldn't study the whole thing but in plain english he explains kinda what they did and his reasoning for getting into it and he just says well I just studied loads of industries this one seemed industry interesting I went and interviewed a 100 people who are experts on it I hired really good people and we're gonna do x y and z and that x y and z is exactly what he's done in his last businesses and now I wanna wrap up by by giving you guys incredibly detailed stats or incredibly detailed strategy on what he does so his first thing that he does he looks for huge industries with lots of fragmentation that are small and profitable but don't have the capital to to scale so here's what he says he goes in a nutshell this is how you ramp up a business you buy a brokerage or some type of small business with $30,000,000 in revenue and you add 30 to 40 bodies to it and you double revenue in time I've looked into companies that have executed this plan but most of them don't have the capital to sustain it I try to find those businesses and I bring all the capital to do it the second thing that he does is he hires salespeople so he says I like to hire hungry talented salespeople at a low base but big upside for incentives I fund their training for a few months and it's not that hard for the winners to build a $1,000,000 book after a year or so it's a business where you have to make 99 calls a day and do 1 or 2 deals so you have to hire people who are psycho I I actually don't know this word what's this we have to hire people who are psychochromatically test high on the need to win scale and low on the need to be liked scale a salesperson will have a base of 25,000 or 35,000 but can make many times that amount through an incentivize a really good incentive program once you get the right people in the system and integrate them on the right it it can be really powerful and finally speaking of it when someone asked him what was the best acquisition of all time they ever made he said they made a powerful software acquisition with a politically incorrect name called rental man and we used that to integrate all of our rental businesses we rolled up into that company we couldn't have made the hundreds of acquisitions we did without rental man and that was his best acquisition all the time and that my friend is brad jacobs and I can go on

Andrew Wilkinson

So he sounds... I both love and find these guys kind of mysterious. I kind of wonder like, what's the thing that's missing in all this? Like, what keeps him going? What's his purpose? How does he use his money? And why does he do this? What's the driving force?

Sam Parr

I researched him, and the guy looks like a Wall Street stiff. Did you look up what he looks like?

Andrew Wilkinson

Yeah, he looks kind of like... there's a character actor that he resembles. I'll try and find a photo of him. I know the type: nerdy, bald, Steve Ballmer-looking kind of guy.

Sam Parr

Yeah, he looks like he would be in Biden or Trump's cabinet. But I've actually seen interviews with him. He's very endearing, and I think that he's not just a stiff Wall Street type who just milks all the numbers out. I actually think that this is his build; this is his urge. He just loves to build. He constantly talks about integrity. He says, "The common denominator of everything we buy is the people we buy from. They have to have high integrity." Also, one of our modes is that we take care of the people in the businesses we work for, the businesses that we're inheriting. In fact, the biggest risk of our plan is that the people we buy companies from leave. So, we treat them all really, really well. I don't think this is actually bullshit because when I got his energy from interviews, I actually believed that he was a good dude and that this was just his art.

Andrew Wilkinson

What do you think, though? What do you think he does with his money? Is that kind of public? Does he do any philanthropy or anything? Because I always find it so interesting. I mean, there are two ways to look at doing good in the world. It's like, okay, you do capitalism, right? You employ a whole bunch of people, you make an industry more efficient, you contribute to global GDP... good things happen because he does this, right? But on the flip side, what's driving him? Is it just to make more money? Maybe it is just continually, maniacally going industry by industry and improving them, optimizing them. That's his gift or whatever. But the guy I'm going to talk about next is really interesting because he basically uses all his money to do crazy good things, right? Which is really fascinating. I'll talk about him in a minute. But do you have any sense of what this guy does with his money? Like, does he buy a bunch of jets?

Sam Parr

I don't know. I cannot figure it out, but I will. I can wrap this up by saying there are a few things that I've learned from this person. The first is like taking the red pill. Have you heard? I don't know, someone just used that phrase with me today, and I'm picking it up.

Andrew Wilkinson

You should be careful. It's associated with all sorts of not-so-positive connotations.

Sam Parr

Oh, well, I didn't know that. What I mean is, like, yeah, I guess when you look at what this person is capable of doing, you think... or when you read what he's done, if you didn't know it was true, you would say, "Oh, that's impossible. No one can do that." But the person has done it repeatedly, over and over and over again, and he seems pretty nonchalant about that. So, what I'm learning from him is that you can create these amazing things. It's hard, but maybe it could be kind of simple.

Andrew Wilkinson

Well, it's so inspiring, right? You basically go find an industry that has... Let's look at the restaurant industry in general. Restaurants are disorganized. They're very difficult businesses with very low margins. People have done this essentially in restaurants by building fast food chains. So, you go in, you build systems, you do training, you incentivize people the right way, and you can make a lot of money doing that. But you can't usually make a lot of money in an individual restaurant. What he has done is gone out and found these fragmented, disorganized industries, like waste management or logistics, and he says, "Okay, I'm going to do the fast food chain, except for that industry."

Sam Parr

Yeah, and it's really, really cool. The second thing that I learned is he actually does the same thing as you. Well, I actually don't know your numbers, but I bet they're similar. He likes to buy companies between 5 and 10 times earnings, and that's like his number. That's what he wants to do.

Andrew Wilkinson

Yeah, I'd say I love to buy businesses for that valuation or whatever, but the problem with buying a business at that valuation is... you're often buying kind of a crappy business if it's going to be that low.

Sam Parr

well these are trash companies

Andrew Wilkinson

What he's doing, yeah, exactly. What he's doing is kind of building a platform where he's like, "I just need one so I can build the systems, and then I can go and acquire a whole bunch more."

Sam Parr

And the final thing, and then we can move on, is that the guy loves debt. Oftentimes, that ends badly. But I personally have zero debt in my life, and I've never really had debt. I actually think, though, that not having debt or not having some type of leverage is silly. I've read articles about him, and he talks about it very unemotionally. He seems like a really charismatic, emotional guy, but he's like, "Yeah, look, this makes total sense because I can grow this business at 30%. Therefore, if I look at the cost of capital, I should allocate capital to this, and it just makes sense." I hear that, and I'm like, "Yeah, everything you're saying makes total sense." I'm just so fearful, and it's really cool that you don't seem to have that fear. I think that's interesting.

Andrew Wilkinson

Yeah, and I think that goes back to not having fatal potential blow-ups in your life. I've heard everything from, you know, I was talking to a guy, and he was saying he's a super rich guy. He goes, "I've paid off my house in full and never have a mortgage or whatever," and it just gives him that sense of security. Maybe this guy is so rich; he's already made a whole bunch of money on other stuff that he can take a little more risk, or he knows how to structure debt or whatever it is. You hear both things, and the problem is you only hear the stories about the guys who leveraged up and did really well. There may be a whole bunch of other Brad Jacob types who went out, leveraged up, and it totally messed them up. They hit a speed bump.

Sam Parr

oh yeah

Abreu Andrade

lost all

Andrew Wilkinson

Their money. So, the interesting thing about this, though, and the difference between what we do and this guy is: this guy's essentially starting a new business. What we like to do is find a business that's already working where we can actually just leave it and make it... you know, maybe we'll help plug in a new CEO or something like that, but we're actually not messing with it. We're not changing the DNA. This guy's like modifying the DNA. He's doing like CRISPR on these businesses and...

Sam Parr

he's working

Andrew Wilkinson

...and warping them as hard... warping them and turning... He's working, yeah, *really* hard. So, I don't like to work hard. I get really excited when I hear about people like this. I'm so glad they exist, but I'm like, "Oh my God, this is a big lift."

Sam Parr

I don't want to do this big lift, but it does seem cool. It's cool. This is like cornrows or sleeve tattoos. I think they're cool; I just don't want it.

Andrew Wilkinson

They're cool for certain people, and it works great for them. Exactly. Face tattoos? Not for me, but great for some people.

Sam Parr

tattoo it's pretty sick that someone else has it but I

Andrew Wilkinson

I don't know if I want it. Totally, totally. Yeah, and I think, again, going back to like this guy, he does make the world better because he employs a lot of people in industries where, you know, people aren't getting laid off because of this guy. Right? Because he's managed this business better, he can probably pay people better and give them more opportunity. He's not going to lay them off because he's got this global business. So it's very, very positive. But what I would want to understand is, what does the guy do with the money? What's driving him? Is he like a sad, empty hole where he's like, "I have to keep doing this all the time," or is he, you know, donating it all to charity or views this as super philanthropic in and of itself? I'm super curious about that.

Sam Parr

I don't know. The only thing that I saw was that he has a good Glassdoor rating, which I actually think is huge. Everyone dismisses Glassdoor, but I'm like, yeah, it’s not like facts, but there is a signal that you can learn a little bit from. I got made fun of from the Michael Saylor podcast that I brought that up.

Andrew Wilkinson

It's the Glassdoor people only go on Glassdoor when they really hate you. So, it's like the voices of the people who hate you most. If the people who hate you most are saying good things, or at least okay things, that's a really good sign.

Sam Parr

Right, so anyway, it's interesting. But let's move on to your guy because I actually know who this guy is, or I know of him.

Andrew Wilkinson

so yeah my guy is dan gilbert and the reason I thought he was super interesting I've talked about him a little bit in the past but this guy has had a freaking massive year so you know 2 years ago or something he was worth like 6 7 $8,000,000,000 baby billionaire now he's worth 57,000,000,000 wait 5 7 57 57 he's number 21 one of the wealthiest people in the united states and this is he's had a crazy couple years so I think it was about 2 years ago he had a massive stroke so he was on the golf course with a friend and the the friend just happened to be a doctor and he said oh that's weird I'm having these symptoms so his doctor got him to the hospital and they he had a stroke in the hospital and in the hospital they were able to do this special procedure that if he hadn't been in the hospital he might have died or it might have been way worse right so he got super lucky and you know as lucky as one can be having a stroke horrible thing and now he's been basically rehabilitating himself and getting back on his feet for the last 2 years and so he's had this horrible personal tragedy but at the same time he's become worth you know 6 x you know as much and I bet he would give it all away to not have had the stroke or whatever so it's super fascinating this guy he described it really well when they ipo ed they just ipo ed his mortgage business he said this is a 30 year or sorry an overnight success 30 years in the making so this guy's been at it for a really long time I think he's super interesting because he started with nothing his dad owned a struggling detroit bar he worked in pizza delivery he just kind of stumbled into hustling and was a good salesperson and he started a business and that business was a company called rock financial which became quicken loans which I'll talk about in a second one of the reasons I think he's really interested interesting is that he's invested into revitalizing his home city so his mission is to revitalize detroit and get it back on its feet because it's struggled a lot he's like a capitalist batman in detroit and I'll talk about some of the cool stuff he's done and one of the things I like about him as well is that he he does a lot of stuff that might not work he takes big swings takes big risks that he think can make the world better and he invests in all sorts of crazy ideas he also has 5 kids which I think is pretty freaking cool I love to see that with these you know billionaires they're not just like miserable by themselves and they care about kids and stuff and seems pretty family focused and then you know he's been through these personal challenges the stroke and then also his eldest son was born with this disease called neurofibromatosis which is like super rare and he's poured a bunch of money his own money into funding research around that disease so it's been fascinating so he said there's a quote he said when I when we grew up all I wanted to do was do 2 things own a sports team and a casino and now he owns both so this is kinda like a childhood dream and his companies are quicken loans which is the largest home mortgage lender in the united states they're bigger than wells fargo which is freaking crazy he owns the cleveland cavaliers the basketball team and a few other sports franchises until recently he owned a casino I think it was called jac which owned a whole bunch of casinos but I think he sold it and then he also owns rock ventures and rock ventures is where all the big swings happen and all the philanthropic stuff happens so they own a ton of real estate almost all in detroit and then they do venture capital and they've invested in everything from restaurants to you know real estate businesses hotels crazy tech companies and all sorts of other stuff he owns rob report which is can I tell you one more thing that he owns

Abreu Andrade

can I

Sam Parr

He owns a few more interesting things. So, he owns, I think, Fathead. Do you know Fathead? Yeah, yeah, I believe.

Andrew Wilkinson

sports it's like those like big hands and stuff and like you got weird gloves to your face

Sam Parr

Kid, you want to put like the face of Michael Jordan on your wall. It's like a decal that you put on your wall. I think he owns the whole thing. He just bought Dictionary.com and Thesaurus.com.

Andrew Wilkinson

Totally random. We were actually... we helped him. I know him; I'll talk about that a little bit. But we helped him with that acquisition a little bit.

Sam Parr

Oh, no way! So you know about it? It was like a... it's like a $20 million revenue thing, or more maybe. It's been doing that for like 10 years. I mean, I don't have any insider information; these are guesses. Am I right?

Andrew Wilkinson

Yeah, he owns Dictionary.com and TheStoreUs.com. When you talk to him about why he bought it, he's just like, "You know, I think this is cool." He had all these ideas of things he could do with it. He's not like, "Oh, I bought it for X times EBITDA and I'm gonna make a 20% return." What I find so cool about this guy is he'll just say yes. He owns Robb Report, which is like a magazine for rich people, and Dictionary.com. He also has a very large stake in Shinola. Shinola has this insane hotel in Detroit, and they make watches. He owns StockX, which is basically like a stock market for sneakers and watches, which is awesome. I'm a large investor.

Sam Parr

because like he he co founded it

Andrew Wilkinson

he's the co founder

Sam Parr

like in his how old is he in the seventies yet

Andrew Wilkinson

he's like 50 50 something 56 I think

Sam Parr

he's that young wow okay he's still a little bit older than like a sneakerhead

Andrew Wilkinson

and he totally

Sam Parr

I he's a cofounder I know that so he was a he he

Andrew Wilkinson

He’s got investments in esports, like just all sorts of stuff. He’s also a large limited partner (LP) in a lot of venture funds. Kinda quietly, he’s the largest LP in Ludlow Ventures. He’s got his own venture fund as well. So, you look at it and he’s got this barbell. He has a really kind of dull, boring mortgage business, which is innovative in and of itself. What he’s done is kinda like Brad. He’s basically taken this fragmented, crappy industry run by banks and small lenders and built out this massive structure. He’s been very innovative around culture and other stuff. Let me just give the history of what happened, though. Basically, in 1985, he and his little brother started Rock Financial, which is basically an independent mortgage lender. So when someone needs a house or whatever it is, they go to them. They figure out what they can offer to lend them the money, and then I think they go sell the risk. They would lend them the money and then sell it off to a bank. Over time, in the late 1990s, the company grew into a huge business, one of the largest independents in the United States. With the dot-com boom, they launched an internet strategy where they made Rock Financial— I think it was rockfinancial.com or digitalmortgage.com or something like that. In 2000, what was it? No, 1997 or something, Intuit acquired their business because they were like, “Oh my god, this is like, you know, this huge disruptive digital finance thing.” What ended up happening is the dot-com boom blew up, and in 2002, he came back and bought his business back. So, he sold it for a ton of money, I think...

Sam Parr

the first sale was 90,000,000

Andrew Wilkinson

okay

Sam Parr

is that right

Andrew Wilkinson

he he basically I I don't know I don't have the exact number here but something like that so you know the guy made a lot of money especially for the nineties but he wasn't like a crazy billionaire yet then he raised money from investors so himself and some friends went back to intuit bought it back I don't know what the number was and what's interesting is they kept the quicken loans name so intuit owns quicken the financial personal finance software and they branded it quicken and so now there's this weird other business they own called quicken loans even though that's an intuit brand so it's kind of a funny thing and it just kept he basically took it took it back got rid of all the crap that intuit had added and started growing it again and this whole time he's living in detroit and watching his own city totally fall apart so in the financial crisis you know detroit I think went bankrupt and he meanwhile is like super rich and living out in the suburbs and he says fuck it we're moving back into detroit and he moves his entire team into detroit so he had 4,000 or so employees they literally bought if you actually go to detroit there's this it's called campus martius or something and it's right in the center of downtown this huge building and he moved everyone there and he basically said for my own employees and for the city we're just gonna fix it and so he built casinos he built like a private security firm so if you walk around there's like there's like normal police and then there's like dan's police he bought 1,000,000,000 of dollars of derelict buildings you know literally like you go there and there's like skyscrapers and he's just it's like going to chicago and he's like oh yeah I own the sears tower and this and this and like basically all of downtown detroit he owns like 20 30% of and he also just announced that he's gonna pay off $300,000,000 of property taxes for detroit residences so this guy that's wild really cares about detroit and since since he started it it's now become the largest independent mortgage business in in the united states you know they've gone public they had this huge ipo and it's been it's been a crazy story he but what I what I I I think about this guy is just he's got such a crazy collection of businesses

Sam Parr

I think, if I remember correctly... I'm probably right, but I believe he sold it for $90 million. He bought it back for like $20 million, and I think he took it public. Did he take it public either recently or right away?

Andrew Wilkinson

quite recently like it was like like 6 months ago

Sam Parr

and he owned most of it when it went public

Andrew Wilkinson

he owned like 85 or 90% of it and it went public crazy

Sam Parr

what's the market cap now

Andrew Wilkinson

The market cap is, let's see here, **$46,000,000,000**. Wow!

Sam Parr

So, yeah, where's the other $10,000,000,000 come from? Just other stuff. Just other stuff.

Andrew Wilkinson

Well, he owns a lot... yeah, a lot of real estate. You think the Cavaliers are probably worth, you know, $500,000,000 to $1,000,000,000. We forgot about that whole part—real estate, casinos, you know, all these stocks. I think he's worth a couple billion dollars now. So, he's just got this crazy collection of stuff. Chris and I got to meet him. The other cool thing about this guy is that he's just a wild card. I read about him in the *New York Times*; they did this profile on him. I have this habit of just cold emailing people I think are interesting. Like, 95% of the time, I just don't hear back. But I wrote him an email at like 1 in the morning and said, "Hey, I'd love to meet you." I got an email back like 5 minutes later, and he was just like, "Yeah, sure." Then I got a follow-up from his assistant, and we ended up flying to Detroit. You know, sometimes when you go and meet these billionaires, they're like, "Whatever." You walk in, you get 20 minutes with them, and that's that. But he was incredible. They planned this whole tour of Detroit; it was like this 2-day thing. They set us up in their hotel, and then Dan spent like 2 hours with us. He's just this super nice guy. He's deeply interested in what we're doing and super engaged. Like, every business I mentioned to him, he'd be like, "How does that work? How can we get involved? What can we do? How can we do it?" He wants to say yes to ideas, which I always find really inspiring. I think some of these people have gotten really rich by being hyper-disciplined and just saying no to everything, but he says yes before no.

Sam Parr

That's really interesting. That's what Sean acts like. I usually say no to everything, while Sean says yes to everything. My joke is that my success is probably going to be quite predictable and it will be really good. Sean's success, on the other hand, is that he's either going to go completely broke and die young, or he's going to become a billionaire. You know, it's a high-risk, high-reward type of thing. That's not the reality, but that's my joke. Can you actually tell the story of how you met someone recently who's a big deal? They said, "Oh, just call whenever; I'm free."

Andrew Wilkinson

Day. Yeah, so I recently got an option to give you a name.

Sam Parr

if you don't want to

Andrew Wilkinson

Yeah, well, I got a chance to talk to Warren Buffett on the phone. Some guy I was talking to said, "You know, I'm trying to figure out philanthropy and how to give money away." Literally, he goes, "Oh, you should talk to Warren Buffett." I was like, "What do you mean?" Then he just CC'd me into an introduction with Warren Buffett. It was one of the weirdest things that's ever happened to me, and it was amazing. I was kind of nervous; Warren Buffett's like my hero, you know? I was not expecting this. It was just a random Friday, and Warren Buffett's secretary emailed me back and said, "Oh yeah, you know, call him whenever. He'll pick up." So I called, and I got put right through. It's just Warren freaking Buffett on the phone! Basically, he said, "Oh yeah, I'm not doing anything. I can talk for as long as you want." I just got to pick his brain for an hour, and it was insanely inspiring. This guy was exactly who you'd expect him to be. I find with a lot of these guys, it's like, "Don't meet your heroes," because they're not who they appear to be on TV.

Sam Parr

all day

Andrew Wilkinson

He's available all day. He talked to me for an hour and a half, and he was just the nicest guy. He's exactly like he was on his CNBC interviews. He showed a ton of interest in what I was doing, and I literally just grilled him for like 30 minutes. "Was he on a landline?" "Yeah, he's definitely on a landline." It was just... it's always really nice when someone is what you hope they'd be.

Sam Parr

That's great! So, we'll bring it back to Gilbert. But just so you know, I have a feeling that clip you just mentioned about Buffett is going to go viral. Hopefully, you're okay with that, and if you're not, you can tell us. Alright, you have something here about his strategy and his culture because I actually want to know what motivates this guy. Do you think that he was... So, I actually sent this to you. I think I used newspapers.com, and I like to read old articles. I read a ton of old articles about Rock Financial, even before it got bought by Quicken. Dan was like a Detroit guy. It seemed like he was very confident—not arrogant—but he just had the "it" factor at a young age, it seems like. Then I read his... what's it called? The 10-K or S-1 when they go public. He was like 30, and everyone in his company was in their forties. So, he was like a young guy, and the business was booming. Very interesting! He seemed like a very confident person at a young age. What do you think motivated him?

Andrew Wilkinson

I think he's been super rich for a long time well yeah I was gonna say like he says there's this great quote he says one of our things is that money follows it does not lead so we want people that are fired up and passionate about their mission and people that aren't so married to spreadsheets and thinking that kind that kind of voodoo controls the future because it doesn't so this theme of doing things because it's cool or because it makes sense or because you're driven to do it versus based on financial analysis and that's the feeling I get about this guy is like he says yes and he wings it and he takes risks and he takes big bets and I think it goes back to this thing of what's the? Of making a bunch of money if you're not gonna try and do cool stuff with it and so he's just very very inspiring in that way and one of the ways that he wins is that he focuses massively on culture so when we visited him you know he probably had 5 or 6000 employees at the time and he said I still personally onboard every single employee so once a month I go into like a conference center and there's a you know a 100 or 200 new employees coming in and I will spend all day with them talking to them about our culture and what you know what we represent and he gave me this book and he he calls it isms these are the like the ideals that that they live by or whatever and usually you get these stupid corporate bse things like you know we value integrity or whatever but it's this series of of kind of like words to live by so you know some of them yes before no money doesn't follow it leads we'll figure it out every second counts a penny saved is a penny you know don't obsess over saving just do the right thing anyway I I just love how he does that and then I also love again this barbell strategy where he's got a conservative cash flowing business and that funds crazy shit and big bets and interesting stuff and you know he also said anyone who dies with money in the bank is a failure right so this is not a guy who's gonna go hoard it or whatever he's gonna give it all back to society which I think is super cool

Sam Parr

That's great! Do you think... does he have... so none of this would have been possible without Quicken working out? Yeah. Was he always hands-on, or did he delegate right away, you think?

Andrew Wilkinson

Well, he's got this really smart CEO called Jay Farner. My understanding is that Jay now runs that business, and Dan floats above, doing all of his different stuff. But I don't know; I think Jay's been there for a really long time. I'm not sure, but I think he's the chairman or something. I think he's kind of taken that role where he starts up the business. He's super involved and still hands-on, but he kind of lets someone else operate it day to day.

Sam Parr

Damn, this is awesome! I've heard him talk, and I judged him incorrectly. I think because he's a nice dresser and he's kind of good looking. He literally slicks his hair back. I thought that he was frankly kind of a douche. Then I heard him talk a couple of times, and I'm like, "Oh wait, this guy is not how I thought he was going to be."

Andrew Wilkinson

Super humble. Yeah, he talks with a Michigan accent. He is super down to earth and super funny. When we were meeting him, we were like, "God, this guy's like... he owns casinos, he's got slicked back hair, he almost dresses like a gangster or something." He's got kind of a serious look to him. Yeah, you look at him and you know there's a story about him punching a guy in the face at a party. You're kind of like, "Who is this guy?" But when you meet him, he's just completely real, down to earth, and cool. I would say, we've met lots of very successful people, and I'd say he's one of the only ones that I would go, you know, there's a small list of people where I'd go, "I'd really want to be like this guy." Right? I'd love to trade lives with him.

Sam Parr

is he grinding still or does he relax a little

Andrew Wilkinson

Well, I don't know. I mean, I think with the stroke, there's a question of, you know, did he have the stroke because he was stressed or had high blood pressure? I don't know, but I'm not sure. I don't know what his approach to work is or whatever. I haven't worked super deeply with him. I mean, we looked at that Dictionary.com thing for him and gave him our feedback on what we would do with it. We've done, like, you know, MetaLab worked with Quicken Loans a little bit. Dan's lit me up before via text saying, "You know, this design sucks and you need to make it better." But again, like, that's what's cool about him. He's running this freaking $60 billion empire, and yet he's still texting me going, "Hey, this website sucks and that color is wrong. You know, tweak this." He's just a real person, right? So many of these guys are like reptilian, right? They're too slick. They're never out of place. They won't admit any of their flaws. It's neat when you meet people and they're just real. They're flawed human beings, and they're doing cool stuff.

Sam Parr

That's great! I've just become a Dan Gilbert fan. I prepared more than you, I think, and I believe you picked the right guy. You won! I think you've won. You've convinced me to become a Gilbert fan, a Dan Gilbert fan. He is also really into hip hop culture. For instance, I think he's the biggest investor in Rap Genius, which is not really relevant anymore, but...

Andrew Wilkinson

better or for worse

Sam Parr

Yeah, for better or for worse, correct? But it's whatever. I mean, you're going to lose sometimes if you say yes to everything. But that's cool that he said yes to that, and he's in. So he's kind of got like street cred, and he does actually seem like a pretty cool guy. Then that Dictionary.com deal... according to the news, it said that he bought it for $100,000,000, which is pretty sick. I bet you that company could do $10,000,000 or $15,000,000 a year in profit if it wanted to. But you would know more than I do. That's pretty sick. I'm a Dan Gilbert fan now.

Andrew Wilkinson

yeah me too

Sam Parr

**Abreu, what do you think of our first episode of "Billy's Billy of the Week"?**

Abreu Andrade

I liked it. I think there's a lot to take away from both those guys. I'm curious to see what people's reactions are going to be, but I think this could become a weekly thing.

Sam Parr

sick I think we're scheduled to do it for at least 1 more week right andrew

Andrew Wilkinson

are we doing we're gonna do the same format next time

Sam Parr

you wanna do a different one

Andrew Wilkinson

Well, I like doing this, but the research is annoying. It's so much fun when I can just wing it.

Sam Parr

I have something cool for you. So, okay, at HubSpot, we now have two full-time researchers. If you'd like, we can send a couple of people to them. I mean, I didn't do it this time, but you can. We'll hook it up. You mentioned a few people who you're interested in, and our researchers will take care of it.

Andrew Wilkinson

oh dude I love that it's awesome

Sam Parr

so if you're interested

Andrew Wilkinson

in mister mister corporate big shot

Sam Parr

I know it's trust me it's

Andrew Wilkinson

also where's your crazy camera setup are you on your like crazy dslr right now

Sam Parr

no but have you've seen it right it's real nice right

Andrew Wilkinson

yeah it looks amazing

Sam Parr

I'm driving to Saint Louis to meet a newborn baby, my niece. However, I am stopping in Oklahoma City to meet up with a bunch of listeners because that was like the middle ground. I just tweeted out that I'll be in Oklahoma City, and like 50 people signed up. So, I decided to stop, stay, and meet people. Then, I'm going to drive to Saint Louis tomorrow.

Andrew Wilkinson

Isn't it crazy when you think about it? I remember doing this with our invoicing software like 10 years ago or whatever. It was really small, but we had thousands of customers. You don't realize, like for you, you're just doing a podcast and you see these numbers. It's like, "Oh yeah, look, we got 20,000 listeners" or whatever. When you actually think, like, okay, there are actually 20,000 people all over the world listening to you who feel like they know you. And when you tweet out that, "Hey, I'm in Oklahoma City," some random city in the United States, and 50 people show up in person, that's freaking cool.

Sam Parr

It was even more. Yeah, I was shocked. More people tried to RSVP. Then I tweeted that I was going here, and someone was like, "Hey, I own this fancy hotel. Would you like to stay here?" I go, "Yep, do you guys have a restaurant?" He goes, "Yep." I go, "Alright, I'm going to have 50 people come." We just created an event on the Brightpage, and it's sold out, right? I mean, it's free.

Andrew Wilkinson

Are you vaccinated? Yeah... Ugh, dude, it's taking forever. In Canada, it's going to be like another 2 months.

Sam Parr

Yes, I'm vaccinated, and I still wear the mask to make people comfortable. But I'm vaccinated, so...

Abreu Andrade

I'm gonna go which one do you get

Sam Parr

I don't know I I'll I I don't even know

Andrew Wilkinson

you get 2 dose or one dose

Sam Parr

2 which one's that

Andrew Wilkinson

probably pfizer or moderna yeah

Sam Parr

yeah it was one of those

Andrew Wilkinson

dude I'm so jealous I'm so I'm so done I'm so me

Sam Parr

And my wife got it done, and so that's why I'm traveling.

Andrew Wilkinson

A little bit. Do you think that this will be like... you're gonna be happier as a result of this? It's kinda like you had 100 days of rain and then all of a sudden it's sunny, and you appreciate it way more than if you lived in Southern California. Like, did you just have a boring year and now it's super exciting? Does it feel like you've just been let out of prison or something?

Sam Parr

From a personal perspective, from a business perspective, from fitness... I don't want to sound callous because I know there's bad stuff. COVID was so good to me. I loved it. I mean, I kicked ass! My family and I, we crushed it. I enjoyed the downtime. I enjoyed getting fit. I enjoyed moving. Business-wise, business boomed. Are you in the same boat?

Andrew Wilkinson

No, I would say if anything, I have a tendency to be a workaholic. What I used to do is go work at a café, and then I'd run into my buddies who would also go to the same café, or someone I knew would come, and I'd have lunch with them or go for a walk. It would just force me to kind of get away from work, gain more perspective, and break up my day. Or I'd still be working, but I'd be going from meeting to meeting to meeting, getting eye contact and face time. Now, all I do is work. I'm basically at a house that we rent, and then I drive home, and that's it. This winter, it's been too cold up here in Canada to really go and sit on a patio, so it's a total bummer. I'm an extreme extrovert; I love spending 2 to 3 hours with other people every day. So, it's been grinding on me for sure.

Sam Parr

why don't you come down to texas

Andrew Wilkinson

Because, well, my wife and I have been building a house for the last three years. We're moving into the new house at the end of this month. Otherwise, I've gone to my wife and said, "We just need to move to Hawaii for six months and just... f*** off, go get vaccinated, and then wait for the border to reopen." The reason I can't fly to Texas is that if I fly over the border, when I come back to Canada, there's a mandatory two-week government quarantine, even if you're vaccinated. So it means, with two kids, I have to be stuck in the house or by myself. My kids can't go to school. It's just like, that's not fun.

Sam Parr

Do you know the downside that I've had? I've met so many people digitally, and I hate that I have so many online friends. My phone texts are always full; I get so many messages. It's not like I'm necessarily popular, but I receive a lot of text messages and emails. I do phone calls all the time. So my problem is, I don't want people to contact me anymore, or I just ignore them.

Andrew Wilkinson

Back to like this problem that you'd be so stoked to have, like, five years ago. I have the same problem of like, I post on Twitter and then someone DMs me, "Hey, check out my business. Would you get on the phone with me and talk about it?" Five years ago, I would have been stoked. I'm like, "Oh my God, I can help all these entrepreneurs and make all these new friends." Now, it's like I get 20 of those a day, and I just want everyone to leave me alone. I'm trying to figure out how to even just deal with the amount of email and text I'm getting. This is the downside with scale, right? With 35 businesses, there's always something happening. There's always a problem to solve or a text to respond to or an email. So, it's pros and cons, right? I always make this kind of... I historically always kind of claim to be this guy where I'm like, "Oh, I have this great life. I have all this freedom. I don't run my businesses." But that worked when we were at 20 companies two years ago. Now, I'm hitting this threshold where I'm like, "Okay, I'm back to being busy again. How do I restructure this?"

Sam Parr

yeah you're gonna you're gonna have to hire a you did 2 1 you gotta hire someone to run that

Andrew Wilkinson

I need a chief of staff no I'm just kidding I hate that title

Sam Parr

I know right

Andrew Wilkinson

I was I find that so douchey

Sam Parr

no you need a ceo of tiny now maybe yeah I always love I always

Andrew Wilkinson

I love these Silicon Valley CEOs who are hiring an assistant. They're like, "I need a chief of staff, like I'm the president." That's so ridiculous.

Sam Parr

Yeah, they should just replace themselves. Then the second thing that you did, which might hurt you but you'll figure a way out, is you painted the picture of yourself as this guy who's like, "What are you guys talking about? It's so easy! Why are you working so hard?" Now that you're doing it, everyone's going to be like, "Told you! Told you!"

Andrew Wilkinson

Well, I think the way I describe it is this: when you look at other people's businesses and you've hired executives, or let's say you own a bakery. You're looking at a bakery owner who is staying up until 2 in the morning baking. They're sleeping for 4 hours, working the till, and covered in flour. You're looking at them and thinking, "Dude, it's so easy! Just go hire staff and build a manual. This is not rocket science." Then you do that, and now you're the CEO of the bakery. Now you have to deal with people problems and a different level of issues. To me, it's like I've done the right stuff and I've hired great CEOs. I have all that, but now there are just too many different things to keep tabs on in my brain. I think humans aren't designed to think about more than like two problems at once. So when I have 10 problems or 30 businesses, it's just hard to feel on top of everything. I think you can... I don't know.

Sam Parr

I think I learned this from you, actually. Then another person was like, "I was just going to let this burn." Oftentimes, it doesn't; it survives or gets stronger.

Andrew Wilkinson

Usually, they figure it out, right? If you don't respond to the text and you take 4 hours to respond instead of 10 minutes, usually it's like, "Oh, actually I figured this out." Or you train people that you don't respond quickly unless it's an emergency, and they go figure it out. But if you jump in and you solve their problem all the time, they're just going to keep asking you.

Sam Parr

yeah and I I kinda came to the conclusion of like I'm just gonna let it die and then

Andrew Wilkinson

Because it goes back to that thing of, you know, Tim Ferriss or any of these people who talk about these hacks. The hacks are real, but what's also real is human nature is to be miserable. You know, old people who are rich and retired can be angry about their neighbors, their grass, or their vacation getting canceled, or whatever the silly thing is. And you're looking at it like, "Dude, you have a nice life. Relax, enjoy yourself." I think humans just always need something to be upset about. For me, it's like, you know, I've got... I'm so happy with where I'm at, and I love all my businesses, but I manage to still make myself miserable.

Sam Parr

I would change it too we don't need something to be unhappy about but we need a war

Andrew Wilkinson

I need a fight really

Sam Parr

I totally agree. It's good for me to have a fight. I love having an enemy.

Andrew Wilkinson

Thing I'm not sure... Sword? I'm in the same way... My business partner always says, "You need an enemy." I get so fired up at that, or like being a wartime CEO. But then, like yesterday, I did this viral tweet. I got the biggest tweet ever, right? So how many...

Sam Parr

people did that reach

Andrew Wilkinson

30,000 likes. I haven't checked the number of people, but I think it was like tens of thousands or something in retweets, right?

Sam Parr

So, it's massive. Sean's clubhouse thing reached, I think, 6,000,000 people, but your thing looked like it was even bigger.

Andrew Wilkinson

where do I look does twitter analytics

Sam Parr

Yeah, on your phone, there's this thing called **Insights**. So, you go to the tweet, and then underneath the like button, like the heart button, you see something that says "View Insights."

Andrew Wilkinson

I got 7,200,000 impressions and a total engagement of 1,100,000.

Sam Parr

that is 7,200,000 is so good

Andrew Wilkinson

Yeah, so it's crazy. So anyway, I did that and, you know, it was like dopamine hits. I was talking about a failure, right? It was like I hadn't really talked about it. I publicly revealed I had lost $10,000,000 on this business I'd started, and it was just kind of like exercising a demon, right? "Hey, I'm just sharing this horrible story or whatever." The thing about Twitter is that 2 to 5% of your audience will always misinterpret what you say. They go, you know, "Oh, hey, technicality," or "This isn't right," or "You're trying to come across this way, and that's not true," or whatever it is.

Sam Parr

the classic

Andrew Wilkinson

and so

Sam Parr

how privileged of you

Andrew Wilkinson

totally oh how privileged you lost $10,000,000 or whatever it is

Sam Parr

the?

Andrew Wilkinson

And I had... it was hilarious. So, my story was basically that we started a productivity software called **Flow**. I decided to bootstrap it like **Basecamp**. We had a big competitor, **Asana**, which was run by a billionaire, the co-founder of Facebook. He raised a **shitload** of money. Originally, I was like, "Oh no, we've got a better product." But then they just made their product better and outspent us on marketing. We got killed, right? So, I do this, and you know, the co-founder of Asana, who I really like, and I thought I complimented him in the story, started taking issue. He said, "You know, in 2012, we didn't even have a marketing budget," and all this **shit**.

Sam Parr

dustin was fighting with you

Andrew Wilkinson

dustin was like fighting with me on twitter and I'm like dude I like you

Sam Parr

yeah you said

Andrew Wilkinson

I like you. I'm complimenting you. You're such a nice guy, and you said it really nicely and all this stuff in the tweet. You're attacking me.

Sam Parr

In the tweet, you said Dustin very nicely, "We're gonna crush you," and he did. But I love him a lot. That's like what you said; he didn't.

Andrew Wilkinson

Really, he didn't even say, "I'm gonna crush you." It's more like, "Hey, here are all the challenges you guys are gonna have. You should really join us, and we'll do this together." Right? This is a very collaborative message because I think they wanted to bias. But then, you know, my other hero, David Heinemeier Hansson, who I've worshiped forever in terms of the business they've built, wrote this whole post about how I'm pro-venture and I'm, you know, misallocating success to all this stuff. He totally twisted what I was saying. So, it's like this downside of Twitter and being public—starting a fight, stirring the pot, and sharing.

Sam Parr

what's going on like your buddy

Andrew Wilkinson

Yeah, and I'm friends with them. We're texting about it, it's fine. But it goes back to the negative emotions of sharing and being out there and having, you know, having enemies. It comes with shitty emotions, right? I'm debating this right now: Is it worth it? Over the last 2 years, like... I love coming on here and stuff, but is it worth having a public profile? Is it worth the negative emotions?

Sam Parr

I think that this is like a rich person's problem. It's kind of not about being rich or whatever you want. It's like whatever you're trying to get, whatever you're trying to achieve, you get it and you're like, "Man, that's not as good as I thought." I've experienced this as well. So if you've noticed, like online, I've actually tried to be far more low-key than ever before because I find the pressure and the attention to actually be a net negative. Although that's like... that's a shitty thing to say because it's not really a net negative. I'm happy with the outcome and I wouldn't trade it, so it's not really a net negative. But I completely agree, I think that...

Andrew Wilkinson

but could

Sam Parr

I'd rather I could be anonymously right now

Andrew Wilkinson

Well, this is the question: could you be known? Could you still be outspoken in audio and stuff but just have your photo nowhere so no one knows you? Not reveal too much personally or whatever? Because the cool thing, as an extrovert, I light up when you're like, "Oh dude, I tweeted this out and 50 cool people showed up at this event!" Right? That is the power. By not being public, you actually aren't sharing your lessons, and you're not helping the next generation of entrepreneurs and stuff. But you're also not connecting with new people, and you're making all these friends as a result. Maybe you don't need new friends, but that's so cool.

Sam Parr

Yeah, so we have two options. 1. We just have thicker skin and stop being such a wussy about it, which is hard. It's really hard. 2. We build anonymously a little bit more. We're actually having, what's his name? Balaji, the crypto guy. Yeah, he's going to be on the podcast in a couple of weeks, I think, right? Abreu. His whole thing is that he has this big prediction that it's going to be the norm for your coworkers to actually be anonymous. I wanted to talk about that because I kind of agree. I think there's a world where that could happen.

Andrew Wilkinson

It's fascinating to think about... if you had a work persona and you're just like, you know, "Sam X," and then you're Sam Parr in your personal life. And Sam X has a reputation, and you talk about what you're doing and stuff. That's super... I mean, there's that guy, the samurai, whatever the [expletive] the guy [is called].

Sam Parr

financial samurai I'm a big fan of

Andrew Wilkinson

Financial Samurai... mhmm, you like that guy? No one knows who he is, right? Or what's the guy's name? Mister Money Mustache. Nobody knew who he was until that New York Times profile, right? And that's the ultimate.

Sam Parr

Totally! You and I both probably have friends who we feel are incredibly close, yet we've never met them in real life. We've actually never heard their voice or seen their face. I have a ton of friends like that. I only communicate with them through text, and I know what their profile picture is. I consider them to be great friends.

Andrew Wilkinson

But even, even look at Jack Smith, right? It's like his username is Jack Smith, but his photo is just some random cartoon thing. It's fake, and that is smart, right? Like, dude, I was texting with someone last night, and he was saying there's a Twitter user—I think he has like 200,000 followers or whatever. The guy gets death threats, right? I look at his Twitter, and I'm like, "This isn't... this is pretty innocuous." He's not like some controversial... I mean, I can't say, but not super controversial or anything like that. And the guy gets death threats. You just go like, "Wow, if that's what you're dealing with..." I remember I had this guy six years ago, a schizophrenic guy in my city, who thought that because we worked with Apple, we had the Apple Watch. This is before the Apple Watch came out. He thought we had the Apple Watch plans, and he showed up in our office in like a super manic state, quivering and like demanding with his fist bared that we give him the Apple Watch stuff. We were able to cool him down and get him out or whatever. I have like some schizophrenic people in my family who knew how to deal with it. But you think about it, like that's only gonna happen more as you have a bigger and bigger presence. And that kind of stuff's a little freaky, right? You don't want to get like John Lennon.

Sam Parr

I call it "love knifed." You know, they love you so much they're gonna stab you. Totally. It is fearful. I mean, I've not had death threats, but there have been times where Sarah and I have been on vacation. We'll take a picture of our guest or the vacation home, and we'll cover the address. But still, I'll get like 5 or 10 packages from people saying, "Oh, we just found the house on Street View," and they'll send stuff. Yeah, it happens all the time, so I'm not...

Andrew Wilkinson

I creepy

Sam Parr

they asked me not to take pictures of the of the house even if we cover the address

Andrew Wilkinson

dude that's super creepy

Sam Parr

And I'm a nobody. You guys, you and Sean, have two times as many followers. I mean, it's weird.

Andrew Wilkinson

It's so interesting... It's such a first world problem, right? Oh no, I've got this big audience, all these people listen to me or whatever. But yeah, it's a double-edged sword.

Sam Parr

yeah you know people always say that's

Abreu Andrade

a good problem to have that's a first world problem and my reply is

Sam Parr

like yeah you're you're right

Abreu Andrade

it's still a fucking problem though

Andrew Wilkinson

Totally, it's very real. I was on the phone with someone the other day, and he was saying, "Oh yeah, I want to be a billionaire." I responded, "Well, think about being a billionaire. Think about the pressure of having $1,000,000,000 and knowing that you can..." Here's an example: I read Bill Gates' new book about climate change, right? And I'm thinking, "It's okay, I don't have enough money to really do anything about this. I don't feel any personal responsibility. Let's let the crazy billionaire Bill Gates deal with this." But if I were a billionaire, I'd be going, "Oh shit! I need to call Bill, and I need to help. This is my problem now." If there's a shooting in town, I would need to fund the police to make it better and solve these problems. There's a lot of pressure that comes along with large amounts of money.

Sam Parr

did you see

Andrew Wilkinson

It's interesting to think about what's the right amount of money. The people I admire the most are often those who have enough money in the bank that they can do whatever they want, but not so much money that they can turn into wackos or stress themselves out.

Sam Parr

what's that threshold of they can do whatever they want like what does that mean

Andrew Wilkinson

I think really it's like... in my city, it's maybe like $5 to $20 million is enough to, you know, live a great, great, great life. Right? You could obviously do a lot less, but...

Sam Parr

I can pretty confidently say that I think **$20,000** is the threshold that you could live a great life in pretty much any city for the rest of your life. Yeah, I think I would say that now.

Andrew Wilkinson

That's like, you could get a crazy apartment in New York, live like a king, and you're good forever.

Sam Parr

forever

Andrew Wilkinson

But, I mean, with $2,000,000, even $3,000,000, you can live somewhere in the world amazingly well.

Sam Parr

Yeah, well, Andrew, thank you. We'll do it again next week and we'll get our research to do stuff. Abreu, what do you give this out of 10?

Abreu Andrade

9 out of 10

Sam Parr

oh I'll take that that's good

Andrew Wilkinson

would not have expected that