Every Business I Tried Before Making My First Million

Transcript from https://podmenti.com/t/62964a4b17f04468

All right, everyone on this podcast we talk a lot about the successes, but I want to talk about the failures. So here's about ten different companies that I started before I made my first million. Almost all of them they sucked. It didn't work. But I'm gonna explain how much I made for each idea and the lesson that I learned.
I feel like I can root
Well I know I can be what I want to
I put my all in it like my day song. On the road, let's travel now look. What's up, Sam?
What's going on?
Let's set this up. Name of this podcast, My First Million. When did you make your first million?
So cash, like cash million, I made it when my wife worked at Airbnb and it went public.
And that that's when we made our first and then about three months later, I think it went later in December, my company sold in February, and then we made a lot. Leading up to that, we were doing pretty good too, but I don't think we had crossed one million.
Okay. So you made your first million, let's call it thirty one years old.
Here's all the businesses you tried.
Before that, before making your first million, which I think is pretty fascinating. I wanna go down this list. Does it start in high school? Yeah.
All right, go go for it. Give me number one. In high school I made twenty five hundred dollars one summer by buying graduating seniors old sports equipment and selling it on eBay. And so what I used to do is I would just buy like people's like
track spikes or uh, you know, whatever, and I would sell it on eBay and uh most of the time that I didn't buy it. They would just give it to me. They would hand it to me. And I on eBay I made twenty five hundred dollars. That was my first business where I actually started making online money.
And this is flipping, basically. This is flipping assets that other people
Not only undervalue
They might
To the not value it to the point where they're just happy you took it off their hands.
Yeah, and frankly I did this in college too, which I didn't list here is when uh uh at the end of the college year I would I would stay a few weeks after the end of the school year and when people were moving out, I said, I have a storage unit, you can come and put it here and just give it to me, you're gonna throw it away, just give it to me, and then I'm and I would resell it.
Exact. I saw people doing this in college with textbooks. They would just say, Oh, at the end of the year, you don't want to take all these heavy textbooks home. You're done with that class.
Well, guess what? The next semester, there's a bunch of people that are gonna need that exact textbook that were happy to buy it used.
And so they would just go buy up people's text they would just take people's textbooks and they each book was like, you know, a forty or fifty dollar
Uh, you know, future sale that they were able to pick up for free.
Okay. And then at twenty I started a hot dog stand, which everyone makes fun of me for talking about. You I have a hot dog stand and you have a sushi restaurant. There's sick of us talking about it. But I had one called Southern Sam's A Wiener's As Big as a Baby's Arm. Basically I knew a guy named Doc who had a hot dog stand. He let me rent it from him with very little money up front. I had to I was able to pay him on the thirtieth as opposed to the first of the month, so he hooked me up.
And with five hundred dollars, I went to a restaurant depot and I bought a bunch of Vienna sausages to get my supply.
And I was in business, baby, within a week of having this idea. And I used to live in a bad neighborhood. Rydell was my next door neighbor and he became my best friend. He had served twenty years in prison for attempted murder, and somehow we became best friends. He had the he had the spare key to my house. This was my guy and Rydell ended up
working with me at Southern's and we spent all day outside and it was a pain in the butt. Some days I would make fifty bucks, other days I would go to um a concert or like an outdoor place that was popping and I would make a thousand dollars. And I did that when I was about twenty or twenty one.
This is your summer in college or wh what were you doing?
I was in college, I was in class, and so I would work until three PM. I would go to classes from three PM into eight PM, and then I had a night session where I was out by all the bars and that would be like a nine PM to like one AM.
That's amazing. How did you have the idea to do the hot dog stand? You just saw somebody else doing it?
I met a guy who had a cart and I wanted to do something. Yeah. Did he tell you like I'm making three hundred bucks a night or something? I saw the video online of a guy saying how much money the Home Depot hot dog guys make. They make one hundred thousand dollars a year, the ad said. And you were like in.
I was a man, I was I was broke. I I had my PhD, poor, hard working and driven.
I was Would you do this again, this one? No, man. It was so hard. It was so hard. Not now, but like if you're 1920 again, you needed to. I learned how to sell so well, man. This is what inspired me to get the copyright. I realized that you had to like uh wheel and deal a little bit. You had a schmooth, you had a flirt, you had to do this, and then I realized
What if I could do this on the internet where I could write something one time and have an infinite amount of people come and read it and I didn't have to sell constantly. Didn't have to stand there in the heat. It didn't have to stand in the heat. I'll we'll post a photo here. I had these horrible, I mean, look at me. I'm like the whitest guy ever. I had these horrible sunburns that when I took my tank top off, it still looked like I was wearing a shirt, just a white like beater.
There there's this uh there's this tweet tweet that's been going viral that's um
So so they said flirt with everyone.
Flirt with flirt with women, flirt with men, flirt with old people, flirt with kids, just flirt with everybody. It's non sexual, but literally just be the most playful.
C charming person you could be at all times, like practice this muscle.
And um I actually think this is a hundred percent true. I know a couple of people in my life that are like this. I'm not really like that, but I've been starting to do it just for fun, just as a little
Mini game. You know when you're just
Living a pretty routine life. You're just going to the grocery store. It's either gonna be a forgettable experience or you try something to make it a little more fun.
I've been doing this and it's kind of amazing. You know what I call it? You know how I'll be able to say nonchalant.
Fish line.
Be chalant. Don't be nonchalant. Be chalant.
It's chilling as hell.
Yeah. Try hard.
I emailed my wealth manager at Morgan Stanley.
And I was like, Hey, I made this trade and it
Like there's like a commission of like a hundred something bucks at the end of every like the trade. I was like
Is there like a magic button you got over there, man? Like do you got a magic button you can push that makes all those fees go away?
And that was what I sent the you know the private wealth manager.
And he goes, He just replied
Magic button pushed.
Trades uh commissions reversed, enjoy your trading. And I was like, just flirt with everybody. Like I could have been an annoying Karen. I could have just I could have just took it and d done nothing. I could have been a Karen complaining.
Just flirt a little bit. Everybody likes to be flirted with.
So my next business after that, I started this thing basically in Tennessee at the time.
white whiskey, which mo it's called moonshine. Moonshine technically means illegal whiskey, but there is these companies making whiskey that was in a mason jar and
Yeah.
They called it moonshine.
And I started selling that online.
And I thought I was doing it the right way because I kinda like Googled it and I talked to like a lawyer where I was like selling it as a novelty because it was kind of like a gift item.
I did that for about two or three months and then I went to my university's uh like entrepreneurship program where they had free legal advice and I was like, Hey, I've made ten grand in like the last like, you know,
thirty days or something selling this whiskey online.
I think I'm following the right rules, but is there anything else I need to be doing? And they're like
Yeah, brother.
You gotta you better shut that down tonight. Uh and so that was like my second internet business, which
inspired me to get into the game of the internet. And my lesson learned on that one was if you're gonna do something
Like this, you better really do it right. And you better pick something that aligns with your values. Around this time I was still drinking and I didn't even like alcohol, but I mean I I you know, I had a love hate relationship and I was like, Why am I gonna start selling this? I I don't wanna do this. This is stupid anyway. But
You're gonna see there's a pattern. It was definitely like a quick money, which I think everyone who becomes a good entrepreneur, they they do the gray hat gray hat area.
Phase. And this was my gray hat phase.
Okay, I like it.
You started it online. Did you learn about online marketing through this? Like were you
Well I mean how'd you how'd you get the ten K? Where'd you where'd you get your customers from?
I posted on forums, like motorcycle forums. Like so basically like this whiskey that I was selling, people were already searching for it because the guy Dr. Of course.
That should have been the name. Uh the people were already searching for this whiskey, but it was very early and so I was able to rank super easily on Google and I post it on message board forms of people who wanting who people who wanted it and that's how I made money.
Nice.
All right. So a lot of people watch it, listen to the show because they want to hear us just tell them exactly what to do when it comes to starting or growing a business. And really a lot of people who are listening, they have a full time job and they want to start something on the side, a side hustle. Now a lot of people message Sean and I and they say, All right, I want to start something on the side.
Is this a good idea? Is that a good idea?
And
Again, what they're really just saying is just give me the ideas.
Well, my friends.

So my old company, The Hustle, they put together a hundred different side hustle ideas.
And they have appropriately called it.
The side hustle idea.
It's a list of a hundred
Pretty good ideas, frankly. I went through'em. They're awesome.
And it gives you
How to start them, how to grow'em, things like that. Gives you a little bit of inspiration. So check it out. It's called the Side Hustle Idea Database. It's in the description below. You'll see the link. Click it. Check it out. Let me know in the comments what you think.
Okay, so now you move to San Francisco. I think you you don't you just do like a cross country motorcycle ride to get to San Francisco as well? Uh I do it l at a later date, but this time I flew out there because I had a job offer at Airbnb, which got rescinded when I got there because I'd lied on my resume about getting a DUI.
And so I was out there, I'm like, What the hell am I gonna do? I gotta meet people. And so I start a thing called the anti MBA book club.
And I tried monetizing it.
But I couldn't really at first. And so what I did was I posted ads on Craigslist and on uh Reddit.
And I think I posted on Facebook.
And I got two thousand people to sign up. But here was the premise. It was called the anti-MBA because I was very envious of Stanford students and Berkeley students. I was very envious that they had this network and said.
I'm gonna read it one book per month. We're gonna break it up into a quarter, so a week, a week, a week, a week. And I'm gonna find an expert on that book's topic and we're gonna come and discuss it with that expert. I'll organize and get the expert. You come, it's free.
And I got twenty one hundred people to sign up to my emailing list, and I had about twenty people show up every single week.
Some of those people include Cieva, who's now one of my best friends, is one of your uh close buddies, Neville Medora, who's now who was the best man my wedding, uh came from that. And so some of my best friends came to the anti MBA book club.
And if and I posted a photo, if you zoom in on the top left of the photo, you're gonna see a ski ball machine. I found an arcade that let me host the book clubs for free in that place, as long as we play ski ball.
And w you were uh reading books. Now what kind of books were you reading in this? Is this like
Were the books actually useful for you in business or was selling
White whiskey the right way to learn business.
I don't remember everything we read, but it was like it was like Tim Ferris's book, The Four Hour Work Week.
So you know how like you wanna like if I was a techie, I would have built like Clubhouse or something actually cool, but I didn't have like anyone discuss these books that I wanted to read. But it was kind of a forcing function because I was like, like, I need to get good at business, I better like get educated.
Uh what I could do is I can get these people to come to this book club and I'll just read one week in advance and take really good notes and I'll sort of teach it. Because when you do a book club, by the way, no one reads a book, just the one guy who is organizing it. And so I was just going to organize it. Um organize and talk about it.
Okay, what came next? Okay. And then around that same time when I moved to uh San Francisco, I met a guy who had an idea for a roommate matching app, and I was like,
Hey, I don't have anything to do. May I please join you?
And so I previously had a pickup truck in Nashville where I live. I sold it. I had roughly five thousand dollars. He had a little bit of money. We put it together and we started with this idea called uh bunk.
And the idea with Bunk was it was a roommate matching party website. And so we went to landlords who had two, three, four, five bedrooms, and we would say, We're gonna post an ad on Craigslist and we're gonna advertise this three bedroom as a one bedroom apartment, meaning instead of a three thousand dollars three bedroom, we're gonna advertise it as a one thousand dollar one bedroom and we're gonna get a hundred people who are interested.
And we're gonna host parties to help them team up and move into this apartment and potentially other apartments.
Mm.
Sounded interesting, and it was somewhat interesting.
Couldn't figure out how to monetize it.
Roommate matching apps are one of like four businesses that every just
graduated college kid tries to start, that's one of'em. It doesn't really work.
So we got aqua hired roughly nine months later, which basically meant we got a job and we got some bonus money if we like accomplished a couple of things. But what we did do that was interesting.
And I was not able to do this. I was definitely like the marketing guy.
But we turned that idea into Tinder for roommates.
And that was really dumb because most people when we launched, when we got we actually got tens of thousands of people to sign up for it via these infographics that I linked to that we made, but most people or many people who were using it were just meeting it to date. We shouldn't have just done Tinder for d Tinder. It would have been way smarter.
Um and so that didn't really work out.
Okay, so
I think that to win in business you gotta have
Essentially three components.
The first component is you need to have a money making skill, meaning you have to have something that drives value. This is either gonna be learning to sell.
learning to make things, learning to f hunt down interesting deals, right? Y you know you need a money making skill.
What was your money making skill you were developing during all these across all these different little projects?
Copywriting and also just like tenacity, but like getting after it, but copywriting was the the one and marketing.
Marketing, right. Learning to sell.
Um
Yeah in your case, learning through sell learning to sell through
Getting website traffic and getting the web visitor to do what I wanted them to do.
Cool. The second thing is
You gotta learn to be sort of tenacious and scrappy.
Which comes not as a thing you want to do, but as a thing you are forced to do because you really have no other choice. But once you find that gear.
You now know you have it.
That's how I would describe it is that
Accurate. It sounds like it's what happened in your case, too. Nobody wants to be scrappy, to be clear, right? Like if you had the option to not have to tough it out, you would probably have taken that.
But when you're forced to do it, you learn, okay, I have this sort of animal inside. I can do this. And now I'm gonna use this in every single thing I do. Whereas somebody who doesn't know if they could do that.
They're hesitant to go for it.
Yeah.
And what's funny about that tenacity or sorry, being scrappy is
There's this chart where basically like you
You start that way and you don't like it.
And then you like kinda get some a little bit of fancy.
But then once you already are fancy or successful, you realize
You should always be scrappy.
You know what I mean? There's like a reason that like Amazon has like the pizza roll where it's like you'd only have a team of people that are like four people because small scrappy teams do significantly better uh in in many cases than bigger teams. And so yeah, when we when we met
It's actually hilarious. If you had just taken a picture of both of our offices
And you had said
Which of these two guys is a successful entrepreneur?
Your office was just like a museum. You had a dude, if you walked up to Sean's office, I'm not exaggerating you.
In San Francisco, we led by Yosemite and the redwood uh trees, they're huge. You could drive it, you could cut a hole in it and drive a car through it. Sean's office as it's as if they made a like a
Coffee coaster for your cup.
out of a redwood tree and it was the size of like eighteen feet long. It was like a eighteen foot in diameter circle. That was like a probably a half a million dollar table.
Yeah, it was. We had four stories. We had an entire apartment built in with heated bathroom floors.
Uh so if you needed to stay the night, you could sleep there. Every every wall was made of one way g one way mirrors. So you could like see out, but they couldn't see in type of shit.
We had a chef there every single day. We had a Masseuse on Fridays. We had open bar uh so every Friday we had so all these things. It's a full it's a tw thirty thousand square foot office.
decorated by Ken Folk, one of the fanciest designers in the world.
And uh that was my office. I remember Sam came over one time and he picked up the ashtray, which nobody smokes inside. I don't know why we have an ashtray. It's like illegal to do that.
And he picked up the ashtray, flipped it over, and he goes, This is a seven hundred dollar ashtray'cause the sticker was still on it.
And I was like, I don't know what to tell you. I I don't know what I don't know what I'm doing here. And I stole it. It's like the the Titanic got built and then they just plucked like a twenty three year old idiot and they're like, You drive and I was just driving that that company into the ground.
And you had this um
Like half an office. It was literally like somebody's apartment. It was uh an apartment.
apartment but it was seven hundred dollars. Me and Sava shared it.
Yeah, like the bathroom didn't have a door. Like you just had to be like, hey, I'm taking a shit. Yeah, like the craziest scenario. Sieva was just sitting over there. He isn't even a part of your company. Just like another guy was just there.
And um like the the the the wall like the there was everything was so strange. Like nothing made any sense.
You like didn't have Wi Fi and you're building this internet company.
And yeah, you actually were the one who was building something successful in w at that period of our lives. Like you were actually onto something and I was sitting here just like, you know.
Making things that nobody wanted.
And so uh, you know, your scrappiness was well deserved at that time and and and earned you some good things. I had to go through my scrappy period at a different time. So
The third thing I would say. So one was uh the tenacious side, uh developing that scrappy mentality and being willing to be at the bottom.
And like survive at the bottom.
Two is the money making skill and three is project selection.
So starting to figure out like almost through process of elimination, what are all the bad businesses that you should not be in? I was in the elimination phase for sure. Yeah. You eliminated like, hey, I probably don't want one where I'm standing outside in the heat selling hot dogs because I'm gonna be capped at like how long I can stand outside in the heat. That's probably not a good idea.
Right. So manual labor, it's not scalable.
Um, you know, another one that you did was like illegal business. Like, oh great. A lot of people want this moonshine, but like
It's only gonna go the bigger it gets, the more likely I am to to go to prison. Fail and go to prison. So that's probably not a good project to select. So you were going through process of elimination on project selection. And so you go through this remote matching app. You're making apps now. That's already better.
If I say like what's the sam par criteria now after the after doing all ten of these things.
What is a good project to be in for you?
Well I believe an e key guy.
Which is like what's the world want? What's the world wanna pay for? What am I good at and what I'm passionate at? And I try to find that in the middle, but
I uh my goal and then okay, so that's like the woo woo stuff that I totally believe in. But then the other side is can I get something, can I bootstrap it to a hundred million in revenue in ten years?
Okay, but
Can I bootstrap it? So there has to be some something you're answering underneath that.
That's like saying, You know what, my strategy in chess is checkmate.
Right, like okay, yeah, I get it. But how do you get there exactly? So
What do you look for that's gonna be a thing you can bootstrap? So are you looking for
I can see that somebody has done a similar thing in another space.
Then I can
recreate or apply over here. Seemed like though the hustle was very much that way. Yeah. Um the newsletter, right? You looked at the scam, you looked at a couple of others, you were like, Oh, I get what they're doing and I could do that just in my way.
Yeah, so I I like to s I w I call it like a forgotten business. So there's a lot of these businesses that I haven't even talked about on MFM.
But basically like there's a bunch of
businesses like Hampton that are doing hundreds and hundreds of millions of dollars a year in profit.
And what I tend to do when I look
for ham I mean Hampton's my only company that's what I'm doing for a very long time. But before I started it, I w researched and I go and talk to the owners and I do diligence. And I thought of it this way, but then when AI started coming in play, it really solidified it, which is like something that can't be disrupted easily.
I also like looking at things that serious operators don't take serious because I think that um
There's less competition. So like with the hustle, people laughed at me when we started it.
But I was like, well, if you do the math, it definitely can get to a hundred million in revenue. And I sold before it got there. But Austin Reef, who founded Morning Brew, he only sold part of the business and still kept running it. And they're in the eighty or ninety million I uh revenue, I think, range now. So like the math was right. And so I look for things that
Uh.
Can be real opportunities, but the ballers aren't taking it serious.
Yeah.
The secret to success is weak competition.
If I was to say from afar, I've known you for
I don't how long have I known you? Twelve years maybe, yeah. Long time.
Um
Three Obamas. And what I would say is I've noticed that what one thing you do really well
Is
You're very good at sniffing out.
Interesting things in spaces where other people are not.
Not even looking.
Which is you mostly just following your curiosity and taste.
Uh but you go and you do a lot of research. You do you come across
Nonchalant, but you're pretty fucking challant about the research. Very like you go you go really detailed, you go meet them, you like talk to the bankers, you talk to a lot of people in a space.
to get a real like a a real idea of like what those companies look like.
And because I want to eliminate
the uncertain like okay, so entrepreneurship, I've been thinking about this. The reason I I've I think entrepreneurship is almost philosophical to me and a lot of people is because entrepreneurship is sort of like how much uncertainty and fear can you take.
And still continue moving forward.
Because entrepreneurship is basically like you work on the same thing for six, twelve, eighteen, sometimes twenty four months, and you're like, I still see barely any progress. Is this going to work? And
the price that you're paying for potentially a big outcome or potentially for building a business or potentially being free, it could take five or ten years. And the ones who win are the ones who can handle that uncertainty for a long period of time. That is what entrepreneurship is ultimately, in my opinion, it's dealing with uncertainty and dealing with fear. You have fear over
hiring someone when you only have thirty thousand dollars in your bank account. You have I remember when my first employee had a kid and I was like, it feels like I had a kid. I felt so much fear. Now that this really has to sustain itself. You have fear over finding your first customer
And thinking I am promised them one thing, now I really have to work my butt off to like make it work out for them. You have fear over getting hate.
Uh, and people making fun of him. And so the name of the game of entrepreneurship is just can you handle the fear and can you handle what's worse is the uncertainty over
Potentially five or ten years.
Well beautifully said. Monish Paray had a good uh addition to this, which he said
Understand the difference between risk and uncertainty.
So he was talking about it with the stock market. He goes
Basically the stock market stock market investors hate uncertainty.
Like if they don't know whether your earnings are gonna be good or bad, they will just sort of assume bad, right? Like you guys they get a huge discount.
For uncertainty, but it's not the same thing as actual risk.
Um and you know, risk is like you know, what do you have to lose? Uncertainty is just not knowing what's going to happen. And so
People think that entrepreneurs take a lot of risk.
But I yeah, I actually think that you are a good example of
Well, most entrepreneurs really do, which is they're actual risk minimizers.
It's like how do I
When
While taking the least amount of risk necessary to win.
I'm not trying to take risks. I'm not trying to take unnecessary. I'm trying to vaporize risk everywhere I can.
And whatever's left over, fine. I'm willing to live with what's left over.
And he he tells the story of Richard Branson. So he says Branson is seen as this like freewheeling gunslinger Mr. Risk type of guy, partly because of his look, his brand, et cetera.
He goes when Branson started his airline, which is a very what people would think is a very risky business to be in, most airlines fail.
Even today most airlines don't even make any money, though even the airlines that it that exist are very razor thin margins.
And when he started Virgin
He called up I think it was British Airways and he was trying to get one plane.
So he was like hey
Do you have like whatever, a seven forty seven?
And they were
They were telling him no.
We don't just give out we're not gonna sell you random guy on the phone like he called the customer support. We we don't sell you a seven forty seven.
Can you just connect me to the person who does sell seven forty seven? Like, we don't sell seven forty seven. He's like, All right, do you guys have
extra capacity of seven forty seven, so you're not currently in in use in your fleet. They're like, Yeah, we do.
He goes, Okay, well would you lease one to me?
And basically he started Virgin.
By leasing
The plane, not buy the plane.
Which reduced stress.
He released it and he was only on the hook for the payments like af like if sixty or ninety days later, but he was already gonna pre-sell the tickets.
for the flights. Like the airline business works where you sell the tickets before you end up paying for the f for the plane and the fuel and all the the actual cost of operating it.
And so he realized like actually, well, what's the worst case that ha that happens? I just give them the plane back.
Like that's all I'm on the hook to do is give them the plane back if I can't follow through on my commitment.
But if I can get it to work, I'll know ahead of time'cause I sell the tickets up front. So it's actually a
uh very like risk reduction approach to doing what other people see as taking massive risk. And I would say you're the same way where
When I've seen you go into a business, you're looking to reduce risk everywhere possible.
So you're like
Do uh does another business like this already exist and work?
So I know that there's demand and I know the business model works.
Can I apply it into this space where there's not a lot of competition or there's weak competition. There's not a lot of other s really smart super geniuses running around San Francisco trying to do what I'm doing.
Cool, that's a way of reducing risk.
A third way of reducing risk is you try to bootstrap it. You don't take on external investment. You try to do it where I can start this with pretty much no money. So what do I have to lose? Just my time.
I'm not actually gonna be in the hole if I if the if this goes wrong. That's another way that you reduce risk.
And the fourth one is
Can I use basically my copywriting skills to attract demand before I have to fulfill the service?
I would sell sponsorships before. Yeah, I sold sponsorships. I wouldn't sell but yes, I I would I would pre sell as much as possible.
Right. And so you know, and you would do a bunch of research to reduce risk. You would talk to the bankers to figure out, you know, what works in these businesses. You talk to the ex CEOs, the ex employees to understand what works, what doesn't work in this business.
And so I think you're a master risk reducer.
And so when somebody sees the businesses that you do, they all sound kind of random, but I would say like where you've come to, I think at the end is
You've figured out your money making scale.
You figured out how to be tenacious and scrappy.
And then lastly
You've gotten better at project selection, uh, and and ultimately we'll we'll use s sort of a risk reduction method to pick a project that you think is is like kind of a
I wouldn't say slam dunk, but like
You're not
Hoping for this sort of one in one in a hundred outcome.
It's kinda like I have to fumble execution for this to fail.
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You should hold your breath still on saying I had good project selection because in two thousand fifteen I started a business called It's Juice.
A poison ivy treatment.
Scratch your own itch, as they say. So stupid. So there was this like type of lotion that mechanics used.
it was like a called a green scrub. I forget exactly what it's called, but it it turns out it was also had the same ingredients as poison ivy treatment. And I bought in bulk
Like
Um
Again, like a barrel that you you would have at a mechanics shop and it l was like
Twenty cents an ounce.
that as poison ivy treatment, it's sold for like twenty dollars an ounce.
And I realized I could rank high on Google and so I was got I got in the poison ivy treatment business and I learned the same thing there or that that I learned in the alcohol business, which was and this
This did this was starting to make money.
Which is like do these short little get rich quick schemes that you jump into without like doing the eyeguy uh preparation of like what am I actually passionate about? They're stupid.
So I learned that one.
I feel like I was a lawyer who just stood up and told the jury my client is innocent.
And then at the very end you were like, I did it, by the way.
Yeah. It's like oh I told you, just don't say anything.
Now I think I did good at selecting new things. So I got rid of that and then um I started working. I think that the I have the same story where it took ten years
For me to even figure out what a good business is.
Dude, I don't know how like I read about these prodigies um who do who like are so mature when they're like
Twenty six, twenty seven.
And I just I'm like, am I
Was I just like slow to develop? Like when I see some of these smart twenty six, twenty seven year olds, I think to myself, I
still don't behave that way. And I'm ten years older than that. So I don't like when I was twenty six and twenty seven, like
I I didn't know anything. I knew nothing.
And I actually thought this way about you and I was like
He's writes stuff on a whiteboard and he's got these like frameworks way of thinking. I don't think it's frameworks, I just like do.
Yeah. While I was sitting there being like, Why am I just on a whiteboard? This guy's out there just doing it. I gotta do what this guy's doing. It took it took me ten years to even figure out at at all what the hell was going on.
Ten years.
And ten years you could say that. Look, I said that in ten seconds. It took me ten years. Watch. That was so quick.
When you're in it.
Ten years is like an eternity, especially because you don't even know that if I knew, by the way.
It'll take me ten years, but I'll figure it out. It would have felt so much better.
At the time, it's like the tunnel is still dark, and I don't even know where if and when the tunnel ends, and and I don't know how much like time I've got left to get there.
So it feels much worse in the moment. So if for anybody is out there who's in their kind of tenure
Tenure doing dumb stuff. Arc, you know, I feel ya.
Uh it's it's it's normal. It still works. Just keep going. So uh Lewis and Clark is like one of my favorite stories ever. But they basically they were sent out f starting in Saint Louis. Thomas Jefferson was like, Hey Lewis, hey Clark, do me a favor.
Just walk in that direction and tell me.
Does it end?
And what's it look like? And what's on the end?
And they just go.
And back then obviously phones didn't exist. Mail's mail didn't exist. They were just walking around uh and they didn't know where they were going exactly.
And it took'em two years. So imagine that. Imagine sending someone off on a trip for two years and having no idea like what's going on, if they're ever going to come back.
And that's what entrepreneurship kind of feels like.
It could have taken two years, it could have taken five years, who knows? But we're just gonna go in that direction and I pray and I hope that we're gonna find something. That's like what the uncertainty feels like.
Exactly. And every year you're like now I know. Now.
And then you say that again the next like oh well last year we were so so dumb. But this year now we have it figured out.
And it takes a certain amount of self delusion.
To not
be like, Hey man, listen, you said that three times already. And now I really believe you this time? And so you need
You need delusion. I think actually that's also why you gotta move to San Francisco.
Is because you'll be surrounded by success stories and you'll see them. You'll be like, Okay, cool. That guy's not special. I could do it. If you could do it, I could do it. And also everybody around you is similarly deluded.
Which really helps.
Because um
You
sort of brainwash yourselves into this mode where you're gonna keep going, keep taking shots, and that that's a normal, rational thing to do, even though it's a completely abnormal, irrational thing to do. I think it's one of the biggest benefits of coming to Silicon Valley.
Can I rattle off uh just a a few tiny ones. So I did this thing called called the Frisco Disco taxi where we dressed up in disco outfits with uh afro's and we gave rides home for people on New Year's Eve. Was this like before lift? Yeah.
before it left. Or maybe like when I think it's a little bit more than literally had left figured out. Yeah. Yep.
I tendered too.
Uh or two.
Uh we made eight hundred dollars that night. I did a copywriting class with Neville. We actually hosted it at your office. I think we each made ten thousand dollars, or maybe we m made ten thousand dollars total.
And then another couple of failures, I uh bought out some real estate.
And I learned that basically the way you make real estate is through doing the most due diligence up front and looking at tons and tons and tons of property because you make your money when you buy.
And that is not my skill set.
And then of course I had the hustle. The hustle started as a conference
Then to a blog, then to a newsletter, which worked.
We launched this thing called Trends, which uh was a fairly successful thing. And then we expanded our events business. Events businesses, horrible. The way that we did it, horrible. We had
hundreds or thousands of people coming to each event.
way better to go after smaller groups and charging a lot more. But back then I couldn't even imagine the idea of someone being willing to spend two or three or four or five thousand dollars per ticket to a trade show. And I wish I would have um
Figure that out. Yeah.
So me and Tyler, the CEO of Beehive, came up with a little challenge for you.
It's the newsletter challenge. Now, if you know me, you know that I'm a big fan of newsletters. I got my own newsletter. I also had a business that was a newsletter business that was amazing. I wrote this newsletter about crypto, we grew it to quarter million subscribers, and we ended up selling it after a year for millions of dollars. And I want you to be able to do the same thing in your business. So we're doing a challenge. 10 grand is on the line.
Plus, me and Tyler will actually be in your corner as growth advisors. You just need to go to bhy.com slash MFM and you either start a new newsletter or you move your current newsletter over there and five finalists will get picked to pitch me and Tyler sort of like Shark Tank and the winner gets 10 grand. So go to bhyive.com slash MFM. That's bhy.com slash mfm to enter the challenge today.
Uh and then this podcast turned out to be a business. We didn't really realize it. You know, I defin I I started alone. I didn't I definitely didn't think of it as a business.
Did you join? I still don't think we thought of it as as a business for
What, the first two or three years?
For the first nine months, I'm almost certain it made zero dollars.
Right?
No, I had a sponsor somewhere that I mean round down to zero, yes. Like you know, like tw ten, twenty grand or something. So I posted this photo. I want I want people to like understand this. So Sean came up with the podcast, I think, in July, and then I think I joined him in September. So we did a uh a a bunch alone and then I joined him later on.
I think sometime in December. So we're talking six months in.
Lance Armstrong.
Uh
For some reason read the hustle and I became friendly acquaintances with him.
He wanted to use my office where Sean and I were recording the podcast.
And so he uh came that day when John and I were recording because he messaged me saying, I need to use an office to for a meeting. Can I use this? And I said, Yeah.
We pull him into the podcast as we're recording and I posted this photo of me.
Lance and Sean standing there.
And we only have two microphones and two chairs. Two chairs. And Sean's two chairs. Sean's like sitting on like the arm of my chair. And during the
And during the episode when Sean wants us talk.
He has to like lead in.
to reach my microphone. And then another episode we had someone like
C we had a guest call it. It was like a digital guest. It was me and Sean in real life and not a guest.
For some reason one of us didn't have AirPods and so we just
Like shared an AirPod. Like we each had one in our ear and I think we were recording on an iPhone.
Like it was so janky even six months into it.
Yeah. Which was funny too,'cause it's not even like these were the early days of podcasting. It's like pretty late in the game of podcasting. Someone should go and look at those old chairs that we use. We picked these chairs because there is a podcast at the time called Fighter and the Kid, and they use
these bright red chairs, the brightest red chairs, and we figured they use it so it sticks out on a thumbnail. Which I don't even know if we did YouTube at the time, but uh we wanted those chairs and it is just a hilarious looking set.
Honestly, it got to be pretty cool. One w when we were in person together, it was pretty amazing. I can't I still wish we could be doing that. Oh, it was so good.
It would be the best. It would be the best. It was so much fun. And we had like a we ran to a Best Buy and bought like a video camera and then and then we had an intern uh record us.
And the shot is just you and I
Like it's dead on you and I talking. And the guys that we were copying was Theo Von and Brennan Schab, who obviously Theo Von is Theo Von now, but back then he was
Like a
Cameo, he came in as a cameo for this other podcast.
Yeah.
Good times. It feels nostalgic going through this stuff, doesn't it?'Cause you are with me for most of it or a lot of it. But doesn't this isn't this kind of fun to like look back and like
It's crazy this the stuff that we've done.
Yes, I mean when you're in it, you just can't want to get out of it so bad, right? God, I just want something to work. Anything. Is this gonna work?
I really hope this thing works.
And I just wanted to get out of it so bad. And then now you're right, you know, you look back.
And I've really never had as much fun since as I did on the come up. Like the come up was really
It was a lot more, I don't know, high variance or just like
unpredictable and like crazy stuff happened and it was fun things that I would never make the time to do now. Like you're never gonna go do Sam's Frisco Disco now. You're never gonna go do the hot dog stand now.
But actually those are pretty fun like kind of random projects. Great stories, great photos, great like
memories of trying to pull it off.
That you were at the time, you know, too dumb to know it was dumb.
And now unfortunately, you know, you sort of have the curse of knowledge the the the further you go.
Where
You're less likely to go try random dumb things.
That might actually have high you know, high high upside or high fun or high memories, you know, that that come at the end of it.
I we have a lot of like young guys listening to this who are in their twenties. Um
Enjoy it, man. It was it was such a blast. It doesn't feel that way.
But I would say with a high degree of certainty, if you do the same thing or you try really hard for ten years and t keep taking risks.
You and I, Sean, have
Dozens of friends from that same era.
And we have seen dozens of them.
Like many, many, many of them succeed. Not always like
Total home runs, but we have many of those, but a lot of base hits, a lot of doubles, a lot of life changing
uh businesses have been built and it's so exciting to like look back and be like
It works. You just gotta give it.
It is uh I mean it's s it sounds corny, but the the truth is
At the time you think your success is about
How hard you're working and maybe your idea.
Or your team or your execution of the the individual thing.
And that's true like at the project level, but at a personal level.
The only thing that's gonna determine your success is basically your rate of learning. How quickly are you figuring things out? Are you adapting and learning and getting better at your next shot than you were at your last shot?
It's that rule of a hundred, right? Like
Do a hundred try it a hundred times and each time try to make one thing better.
If you do that, success is pretty much inevitable.
But at the time you don't think like that. At the time you don't really realize that.
But looking back, that's very much the case. I'm sure there's some people who have a a way to get there a lot faster.
You know, for both you and I took ten years because we sort of through process of elimination got rid of most of the dumb things.
You did f do one thing differently than I think most people did. You never made the mistake of building something nobody wanted.
Which is the m maybe the the main mistake I did. I had a bunch of things that
The business sounds great on paper. If it works, it's gonna be huge.
But nobody even wants the thing to begin with. So you d you don't you die on the launch pad.
Whereas you made the opposite. Everything you made, people wanted.
Whether it was hot dogs, whiskey, whether it was like, you know, a way to get rid of their itch, whatever it was, you know, you you had a way you you always made something that people wanted.
Sometimes the business model was broken or the scalability was broken, but I feel like you did the
You did one thing really well, which is you never made the cardinal sin, which I would say most entrepreneurs make, which is you do something that sounds good on paper, but nobody actually wants the thing you're making. And you're just you spend all your energy trying to convince them why they're wrong and why you're right. And actually no, they just don't want it. They don't need it. You know what's funny?
Why I looking back, I I like for example, the hustle, I think we are at a hundred thousand subscribers in year one, and then I think it was five hundred in year two, and then a million in three, something like that.
And that sounds lovely.
It didn't feel like it at the time. It still felt like I was pushing a rock up a hill.
And so you're saying I made things that people wanted.
Um
Looking back, I agree. But when you're going through it, like I remember Ryan Hoover launched Product Hunt and people were talking about his product way more than like my product, and I was like
That that's what product market looks like. Not mine. I've never experienced that. What the hell? And I look back at it and I did have it. And so some of these things, when you're in the thick of it.
You have to really work hard.
Two
try to come up with these lessons in the sp like at the time. And you have to like sit by yourself to come up with these lessons at in the time because
There has been
So many things looking back where I'm like, had I only done this, I would have had so much more. It would have worked so much better. But I didn't learn those lessons in the process.
So for example
I used to think that it w I was like, I wanna become a big company, so I have to act corporate.
Now I know you want to act small as as long as you can. Or if you have something that is growing at like fifty percent a year.
Don't mess with it. That's a great growth rate. Whereas if you see other people or I saw other people at the time growing significantly faster, but
But
But they ended up like dying and blew up. But I was like, I want to grow that fast. What the hell? And I'm looking back, I'm like, No, no, no, that was that was a rocket. That was fantastic. That was great. It was bootstrapped. It was it was beautiful. Um I think that um that I heard this line that basically says um
V C is like rocket fuel.
And you know who deserves rocket fuel?
Rockets, not fast cars, not cool cars, not cars that you love.
Rockets. And the thing about rockets is most of them blow up and don't go anywhere.
A cool car, a great car, a car you love, that could be an amazing life and it could actually get to the destination eventually, but it might go a little bit slower. And I thought that was an insult to me. I said
But I want a rocket and I want it to work. Nonsense. I wanted a car.
Um and
I wish I would have like had the the confidence back then and learned that lesson that that was the way.
Alright, so that's Sam's story.
Made his first million at thirty one, but
instead of focusing on how he did it, which we've talked about before, it's the tw you know, I don't know, 10, 15 things he tried.
before that, the stumbles and fumbles on the way to success. I'm gonna do mine, uh we'll do one next episode. I'll do my I'll do my version of that where I tell you all the
Uh terrible, terrible ideas that I had going up to finally making it. I feel like I could rule the world, I know I could be what I want to.
I'm putting my law in it like my days off On the road less travel never looking back
Hey, let's take a quick break. I want to tell you about a podcast that you could check out. It is called The Science of Scaling by Mark Roberts. He was the founding CRO of HubSpot, and he's a guest lecturer at Harvard Business School. The guy's smart. And he sits down every week with
Different sales leaders from cool companies like Clavio and Vanta and OpenAI. And he's asking about their strategies, their tactics, and how they're growing their companies as you know, head of sales or chief revenue officer. If you're looking to scale a company up, if you're a CRO or a head of sales, just looking to level up in your career,
I think a podcast like this could be great for you. Listen to the science of scaling wherever you get your podcast.