My First Million: 3 Unconventional Books Every Entrepreneur Should Read

All right. What's happening? A lot of people have been asking me about what I've been reading

lately because I've read a lot of amazing books and I want to do a quick pod, a quick

episode that explains what I'm reading and how it relates to business. Most of these

books, we're only going to go through three or four of them. Most of these books are not

business related, but there's a lot of learnings for business people. I actually don't read

business books. I haven't read a business book in like five years. They bore me. And

lately I've been reading a ton of like adventure stuff. So things about like, oh, when Americans

expanded west or about people discovering North America or ship stories and pirates.

I love that type of stuff. The reason I love that type of stuff is because it basically

makes my daily life, it turns the volume down. It's kind of like, I like to box and I like

to like get into adventures and things like that because it makes my day to day, which

is mostly work and business stuff. It makes it way easier because I'm like, damn, I just

read the story about Shackleton and how I got deserted on Antarctica for two years.

This business stuff is easy. So I like things like that. And so here are three or four books

that I've read lately that have had huge impacts on my day to day with business. And I'm going

to explain how and why they did that.

So the first one is called Undaunted Courage. It's the story of Lewis and Clark. If you're

an American, if you're not American, I actually don't know what you know about Lewis and Clark.

If you're an American, you've heard that term Lewis and Clark and you know that they were

people, two guys that kind of like were sent to discover the West. Well, this story kind

of dives deep on it. And it's the story about in like, I believe, 1804. So there's this guy

named Maryweather Lewis and William Clark. They were tasked by Thomas Jefferson to start

in St. Louis and to discover the West of the country. At this point, Jefferson had just

bought a bunch of what is now the Western part of America from Napoleon. And of course

Indians and Native Americans, they knew all about it, but no American had actually been

really too far west of the Mississippi. And so what's interesting is that Lewis, who is

the main guy, Lewis was kind of the captain of the ship, he took 30 folks. So him and William

Clark took 30 folks and they went to California and back. But no one had ever done that at

time. And what's amazing is that Maryweather Lewis was only 31 years old. And I thought that

that was incredibly impressive. And they took two years to do it. So imagine going off on

like a two year hiking trip and a place you've never been, not knowing what you're going to find

and hoping that you come back. And I found that to be such a good book. The first big thing that

I learned is punishment is necessary. And so in today's kind of like tech culture, I think I used

to joke about HubSpot, the company that bought mine. I was like, you guys are too nice, man. You

guys are like way too friendly. And I think that that's like a common theme with like most tech

companies is they're way too friendly. They're way too nice. And I can't stand that. And I think I

fall victim to that as well. The reason being is when I read this book, there's like a bunch of

different stories. So imagine just a 31 year old Lewis and only 30 guys, it's easy to get like

chummy with them. But he was really, really strict. And so there's a story about how they had to set

up a fort during the winter time. And they set it up along with these Native Americans who they

got to know. And they set up this fort and they built this wall. And one of Lewis's men at night

time hopped over the fence after he had just gotten done hang out with the Indians. And an Indian

saw him and also hopped the fence. And they're like, Hey, man, you can't be here. This is just our

space, whatever. And the next morning, Lewis heard about it. And they whipped their guy 500

times. It's called flashing. So they basically tied him to a tree and with them 500 times, which is

like a horrible punishment. And that's like an extreme punishment. But the reason he did it was

because he's like, look, you just, A, you broke the rule, we said, you can't climb this fence. And B,

now they know that they're allowed to do that too. And so he had really, really strict rules. But

that sounds like crazy. Like, why would you do something like that, that bad? But basically, his

point was, look, discipline breeds excellence. And I have to have strict rules and I have to punish

people in front of others when they've done something wrong. So everyone knows here's the line,

don't cross it. But also, by enforcing these strict rules, it's going to make people know that like

what our standards are. And so there's another TV show I've just started watching. It's called Bear,

the bear. It's about this guy who's got this diner in Chicago. And he basically it's kind of like a

crappy diner. And he's trying to like step it up. And so he sends his cousin to work at this fancy

restaurant that's known for their strict discipline. And the cousin gets to the restaurant. That's

really strict. And he's like, dude, this is bullshit. I'm not following all these rules. They have all

these rules about like, you can't talk to you can't talk to your coworkers in front of the guests,

you have to be you only can pay attention to them. Or I don't want you, or you have to like

polish the forks your first week of work. And you got to spend three hours polishing the forks

because the forks can't have any watermarks on them. And eventually, at the end of the week, he's

like, man, I love this, I wish I crave this discipline. Because what this does is it lets me

know where the rules are, what the boundaries are. And it gives me a straightforward path that I can

go on and it creates this, this, this culture of discipline and excellence. And I love that. And

so a big takeaway from this book is you have to have punishment in order to create discipline. I

think that in our culture right now with tech, we are way too forgiving about certain things. And it

just reminded me that like firing people and things like that, I actually think it's necessary. The

second thing is finding your personal product market fit. So Lewis was an outdoorsman his whole

life. And then he eventually had somewhat like an office job. So he worked with Thomas Jefferson,

where he like was like his, I don't remember what his title is, but he would just be inside the

house all day with Jefferson, like helping him create new laws and how to be diplomatic and

things like that. And he has this great line in this book, he says, the author says, on his 31st

birthday, Lewis wrote in a famous passage, the day I completed my 31st year, I reflected that I had

yet as done but little, very little indeed to further the happiness of the human race. I viewed

with regret the hours that I've spent in idleness and now sorely feel that the want of that

information, which those hours would have given me has been judicious, judiciously expended,

meaning he's like, I've wasted my time, I have to act. And I really appreciate that that he like

said, look, I've been a total waste up until now, now I'm going to get after it. And this is my

mission. And so finding your personal product market fit, we talk about finding your product

market fit with your company, I think you have to find your personal product market fit. And so I

found that to be incredibly inspiring. And the last thing from this book, he understood that the

people that you're leading, each of them have individual traits and you have to figure out those

traits and use that to motivate people. When I was first starting in business, I did a really bad

job of understanding that every person is unique. And I used to think that I could just tell them

what to do. That's not the case. And so in this book, there's this great line where he says, Lewis

had a sense of feel for how his family was doing. He knew exactly when to take a break, when to

issue a gill, when to push for more, when to encourage, when to inspire, when to tell a joke,

when to be tough. He knew how to keep a distance from himself and the men and just how big it

should be. And he did a really good job of figuring out what motivated each person. And that has

taught me that I should probably do the same. Before I was like, you're kind of all just a

bunch of robots to me. It's just human capital. Instead, in order to be a great leader, particularly

like Lewis, you have to do a good job of figuring out what motivates people in creating rewards,

creating punishment in order to fit each person and hopefully making your whole crew better. The

second book that I recommend, it's called The Operator and it's by Robert O'Neill. And it's

about the time when SEAL Team Six was deployed to go and kill Bin Laden. And I love reading these

like army and military books, but there's this great line. So basically, Robert O'Neill and his

SEAL Team Six, they were deployed on this helicopter and they were on their way to Bin

Laden's compound. And he said, once we get on this mission, we knew that we weren't going to see our

kids again or kiss our wives. We'll never eat another steak or smoke another cigar. And there's

this like thing about like, he's going on this helicopter and he knows or he thinks that he's

never going to come back and survive or see his family again. And I found that like so encouraging

because sometimes I'm afraid to tweet something or I'm afraid to like start a business or I'm

afraid to make a phone call when these guys are like going to like, it's a suicide mission. They

think that they're getting dropped off at Bin Laden's compound and they're going to kill them, but

then they're going to die. And I was like, man, if these guys can do this, I can do this other

stuff. That's no big deal. And so I find like a lot of inspiration from little stories like that.

There's this other thing in the book where this other story in the book where basically they

figured out where they thought Bin Laden was. And it was like this compound, imagine like an eight

house, an eight room mansion surrounded by a big fence. And so they did this thing where they built

a model of this house and they spent weeks running through the house and like saying,

all right, at this point, you're going to run this many steps, then that's when the room is going

to open here, you're likely going to find these people in the room, but then you're going to do

this. And they like did it so much that they knew how many steps they were going to take, they knew

how many seconds each thing was going to take. And they planned like crazy. But here's the thing,

when they landed the helicopter into the compound, it crashed. So from the second the mission started,

the whole plan got thrown out the door and everything got screwed up. But there's this thing

called commander's intent. The commander's intent is when the intent of the outcome is clear. So

you have to verbalize it, you have to write it down, you have to say, I'm going to, or the desired

outcome is X, Y and Z. And the reason you plan, even though you know the plan is going to go to

shit, the reason you plan is because A, when something does go to shit, you have something to

fall back on and B, it gives your men or your employees, it gives them confidence that like,

look, it's going to be okay. We've, we've swapped the details, but when it doesn't go okay, you know

what the commander's intent is. And I think that for me, with my first business, I remember starting

it and I said, by the age of 30, I want to have this much money. Great, that's my commander's intent.

The reason I wanted this much money was I wanted like financial freedom and not to stress out.

And then once I had my commander's intent, I created a plan and I created the rules that

I was going to follow when I created what input I needed to get to my commander's intent. And

as expected, a lot of things changed. So I said like, I want this much revenue by year two,

this much revenue by year five, which means I could probably sell. I missed revenue on sometimes. I

exceeded revenue other times. I had to fire people. I changed my value sometimes like things

happened along the way. But because I had my own commander's intent, I said no to everything that

didn't get me to my desired outcome. And I had something to fall back on when I was making new

decisions. So I thought to myself, is this going to get me closer to that particular goal? If yes,

do it. If no, don't do it and avoid it. And so with the operator, I learned about commander's intent

and planning. In the last book, I lied and said it, I didn't read a lot of business books. This

one's kind of business-y. It's called Titan. And it's about the biography of John Rockefeller.

John Rockefeller was a businessman in the late 1800s, all the way to like 1930 or so. He created

Standard Oil. So Standard Oil, it's hard to compare to what it is nowadays because it was so big,

but the offshoots of Standard Oil. So Standard Oil was eventually broken up. And so in the 1930s,

Teddy Roosevelt made monopolies illegal. And they did it because of Standard Oil, the offshoots of

Standard Oil, which they broke up. It's like, I believe it's BP. It's Exxon. It's Conoco. It's

Mobile. All those companies came from Standard Oil. It was as if Amazon, Facebook, and Google were

one company basically accounted for a huge percentage of the economy. And John Rockefeller,

though, you think of this guy, or you think of a business person nowadays as being this like

really vicious person. And he was kind of vicious, but he was very interesting in that he broke a

lot of stereotypes in my head. A few interesting lines from that book. One, he said, I would rather

earn 1% off 100 people's efforts than 100% of my own efforts. And so right now on Twitter and in my

world, we're seeing lots of things about solo businesses. And so a lot of people take pride

in solo businesses. And I think many times they're great, but I have one big issue with them, which

is if you're a solo business, that means you're the only one doing all of the work. And John

Rockefeller in that line where he talks about 1% of other people versus 100% of his, that kind of

changed my thinking where it's significantly better. Even if someone isn't as good as you,

it's better to have a handful of those people doing a lot of the work versus only you doing the work.

That kind of changed my thinking on what it means to be a solo business because I'm like,

I would way rather have a bunch of people doing a little bit of work. And then he has this other

line that says, the ability to deal with people is as purchasable a commodity as sugar and coffee.

And I pay more for that ability than any other under the sun. And I thought that was interesting

because I'm not the best manager, but I can hire good managers. And so that kind of like got rid

of the blocker ahead of my head of like, well, if he says that hiring people is good, but I'm not

great at managing them. Oh, cool. I can hire people to manage them. So that was like really

useful for me. He also has this great learning about gaining a skill. So I'm a huge fan of telling

people, look, before you start a company or before you go and try and do your own thing,

you need to learn a skill. In my case, it was copywriting. I'm a big fan of copywriting,

but he's got this great line where he talks about his time as an accountant. So from the ages of 16

to like 19 or 20, he was an accountant for a small firm. That's where he learned about

operations and where he learned about like, where does money come from? How should it be

accounted for? How do great operations look like? He's got this great line where he goes,

oh, how blessed the young men are who have struggled for a foundation in the beginning of life.

I'll never cease to be grateful for the three and a half years I spent as an apprentice.

And so that's where he learns all about the ability to overcome, to adapt, to get a skill.

And so that kind of changed my life. There's this other great book called Mastery by Robert Green.

And the whole book is about on how you should develop a skill because in learning that skill,

it teaches you how to master something. And it also opens doors for you. And you could use that

skill in other unrelated fields. And that's how you become incredibly successful. I'm a big fan of

learning a skill. And John Rockefeller is one of the guys who taught me the importance of that.

I used to think being a generalist was good. Not anymore. I don't think that anymore. And

it's because of this book Titan. And the last thing I said previously that he was a really nice guy.

He was vicious in business. I mean, he would basically go out and buy all these small oil

refineries. And if they didn't sell, he goes, hey, look, I'm going to write you a fair deal.

If you don't take my offer, I'm going to crush you. I'll show you all my accounting and all my

revenues so you know I'm going to crush you. So I think you should take this deal so we can get

rich together. We can get rich together. Otherwise, you're dead. A lot of them took them up on that

and they did get rich. Some of them, they didn't. And so he was pretty vicious. But he was pretty

much nice along the way. There's this famous story about how once his company got big, Rockefeller

had this piece of exercise equipment. And he was like rolling the exercise equipment into the office.

And this accountant who hadn't recognized Rockefeller said, hey, you got to get that out of here.

You can't have that here. And so Rockefeller just looked at him and goes, oh, all right,

I'm sorry. And he politely took the exercise equipment out of that room and moved it to

another room. He didn't snap back. Like, do you know who I am? And I thought that that was really

interesting and a cool way of handling it and show that you can be a polite guy. You could be kind

and vicious in business. They're not opposites. Another thing is that he was famous for laying

down during meetings and closing his eyes because he just said, this is just easier for me to listen.

And they used to talk about him behind his back and they would say, man, this guy, Rockefeller,

it feels like he's sleeping. Like he doesn't even pay attention to what we're saying in the meetings.

And he would say, no, I'm listening. I might choose to let everyone talk. I want to sit back

and say nothing. And I'm just going to sit in silence. And at the end of the meeting, I'll say,

thank you, everyone. But he just would sit and listen. He would barely talk. And someone asked

him, why? And he recited this poem that he would say constantly. He said, a wise old owl lived in

an oak. The more he saw, the less he spoke. The less he spoke, the more he heard. Why aren't we all

like that old bird? And so he would just sit and listen. And then when he had to make a decision,

he had all types of information that he needed in order to make that decision. And so I used to

think that when you're this big successful businessman, you got to be the one doing all the

talking. No, it's the opposite. You got to be doing all the listening. And finally, he did a very

good job of complimenting people. So whenever he saw someone who was making a mistake, he was famous

for complimenting them first. So like, for example, there was this accountant who he had and Rockefeller

was an old former accountant. He saw a mistake and he goes, these books are very well kept,

very well indeed. However, I noticed one little small mistake right here. And it was like actually

a pretty big error. But he was really good at catching the mistake, complimenting them first,

and then getting them to correct it because he knew that the way that you motivate people is you

kind of got to make them respect you a little bit. You can't insult them in front of a bunch of people.

And he did a really good job of handling people. And I thought that that was a really fascinating

thing for him to do as opposed to being like this guy on TV shows, like,

you made this big error, you're fired in front of everyone to make an ordeal out of it.

So I thought that was interesting. So these are the three books, Titan, The Operator,

and Undaunted Courage. Go and check them out. I'm a big fan of them.

Machine-generated transcript that may contain inaccuracies.