March 7, 2023

The Story of Sam Zemurray is Bananas

The Story of Sam Zemurray is Bananas

Episode 29: In this episode, Alex Lieberman (@businessbarista) and Jesse Pujji (@jspujji) catch up to talk about Jesse’s tips on unplugging when going on vacation. Then, the guys get into the incredible story of Sam Zemurray, the billionaire who built his fortunes in the banana business. Lastly, Alex and Jesse analyze Doola, a startup that aims to streamline the legal formation of companies. 




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Jesse Pujji: Do you know how long my beard is?

Alex Lieberman: You literally say this every time we get on camera.

Jesse Pujji: Nobody knows, dude.

Alex Lieberman: I know. At some point I want to see the full length.

Jesse Pujji: There's a lot of hair. I was thinking there is not like a DTC hairspray I've heard of and I have used the same hairspray for 10 years.

Alex Lieberman: You use it on your head hair, or beard hair, or both?

Jesse Pujji: No, my beard hair.

Alex Lieberman: Got it.

Jesse Pujji: Because dude, my beard hair otherwise looks...

Alex Lieberman: It's like puffy?

Jesse Pujji: Yeah. I'll send you a funny picture. Out of the shower, it's like....

Alex Lieberman: That's wild.

Jesse Pujji: Like Kimbo Slice.

Alex Lieberman: I love that. I got my mini Kimbo going right now. Since now I'm in the plunger business, I have to look like a plumber. By the way, I'm seeing...

Jesse Pujji: Are you in the plunger business, or are you still shaking in your boots? Are you getting back in the game?

Alex Lieberman: No, I have confidence and swagger right now.

Jesse Pujji: All right. There we go.

Alex Lieberman: What's up, everyone? I'm Alex Lieberman.

Jesse Pujji: Yo, this is Jesse Pujji.

Alex Lieberman: And this is The Crazy Ones. Episode 29 of The Crazy Ones. We are back. Jesse, welcome back from vacation.

Jesse Pujji: Thank you. It's good to be here.

Alex Lieberman: How was it?

Jesse Pujji: Oh, man. Have you been to Turks and Caicos?

Alex Lieberman: Yeah, I was there two and a half months ago. It was my first time in the Caribbean ever.

Jesse Pujji: What? That's crazy.

Alex Lieberman: I'd never been to the Caribbean before. Well, I guess, do you consider the Bahamas the Caribbean?

Jesse Pujji: Yeah, definitely.

Alex Lieberman: Well, I was there when I was like eight, so then that was the last time I was in the Caribbean.

Jesse Pujji: Wow. One of the best parts about moving back from California to the Midwest is the Caribbean, because Cancun is a couple hours away, the islands. It's actually funny, one funny thing about California is there's really not that many places to vacation. You can go to Cabo, which is nice, but the beaches are nothing compared to the Caribbean. Then you can go to Hawaii, which is far...

Alex Lieberman: It's five hours, right?

Jesse Pujji: It's five hours, and there's a three-hour time difference. So the second you have son wakes up at 6:00am, so he starts waking up at 3:00am there.

Alex Lieberman: It's insane.

Jesse Pujji: Just doesn't really work. It was amazing. I mean, the kids loved it. They had never been, my wife and I had been a few times, but it was incredible.

Alex Lieberman: Yeah, low-key the craziest thing when I went to Turks was, it took two and a half hours to get there, and it was literally the same flight time as going from New York to Miami. Yet it didn't make sense to me because when I looked at a map and I drew a little triangle, that triangle was not equilateral. Yeah, I was surprised more people don't live in Turks because it's so close.

Jesse Pujji: It seems so underdeveloped for how amazing it is.

Alex Lieberman: Yeah, and there's no taxes.

Jesse Pujji: Yeah, it's crazy.

Alex Lieberman: It's wild. I'm gonna want to ask you questions about your vacation, because I think there's so much stuff we can wrap into business and how do you set things up in the right way where you can actually unplug, and how do you unplug? I decided a cheesy fun game that I do with Carly sometimes that I decided to now do with you. It's called Rose, Bud, Thorn. Have you ever done this?

Jesse Pujji: Yeah. We do it every night at dinner. We call it High Low Buffalo.

Alex Lieberman: Actually?

Jesse Pujji: Yeah. With the kids. We call it High Low Buffalo.

Alex Lieberman: What does Buffalo mean?

Jesse Pujji: Buffalo is like a crazy weird thing that happened.

Alex Lieberman: Okay. So Rose, Bud, Thorn is similar. It's, Rose is a good thing, Bud is something that hasn't yet fully manifested, but it's on the upswing. And then Thorn is kind of the low of the week. So you want to go first?

Jesse Pujji: For the whole week or for my trip?

Alex Lieberman: Do it for the week. We'll do it for the past week.

Jesse Pujji: I was 190 pounds.

Alex Lieberman: And you're down?

Jesse Pujji: Probably eight months ago or six months ago I was 210.

Alex Lieberman: Oh, holy shit. That's awesome.

Jesse Pujji: So I've lost 20 pounds and I'm at the lightest I've been since...

Alex Lieberman: How? A lot of exercise, diet?

Jesse Pujji: Mostly diet. I mean, diet. I was exercising a fair bit already. Then it's really just diet. All these things like Keto, none of that stuff's ever worked for me. There's one thing that works for me every time, and it's counting my calories. It's just super simple.

Alex Lieberman: Yeah, the same exact thing has happened for me in the last three months. I think I told you, started using a nutritionist, and I've lost nine pounds and I'm someone who have been at the same weight for the last six years and I've worked out the same way the whole time. It's like the first time...and I've been counting calories, and that's the only difference that has led me to lose weight.

Jesse Pujji: It's the only thing that ever works for me. Anyway, during Covid I got my weight down and then I kind of came back up as I was getting all this Gateway X stuff off the ground. I took a few years off. So that's a Rose.

Alex Lieberman: That's a good Rose.

Jesse Pujji: Thorn…I'm not good at the Thorn. It's Type 7. We avoid the negatives. I haven't been sleeping well this week. That's a good one. Last night I did not sleep well.

Alex Lieberman: Any reason?

Jesse Pujji: I played tennis until 10:30 and I used to stay up late when I did that, but I've been trying to sleep earlier and then I just was...when you've been competing for 90 minutes, I burned 1,100 calories.

Alex Lieberman: That's wild.

Jesse Pujji: In 90 minutes. I showered, chilled. I watched an episode of Bel Air, the new remake of Fresh Prince. Then I still...

Alex Lieberman: Is it good?

Jesse Pujji: It's good. Eh, it's fine. I mean, it's like Gossip Girl meets Fresh Prince. It's cool if you're a fan of the show, it's cool. Then Bud...Bud is something new that's happening?

Alex Lieberman: Bud is something that either you're excited about, something you're excited that is going to happen in the next week or few weeks, or something that you're seeing early rumblings of things are looking good, or there's momentum building in something in your life.

Jesse Pujji: I'm working on a new venture, so that's a good one. Gateway X.

Alex Lieberman: Because three in two years wasn't enough?

Jesse Pujji: There's a person I've been wanting to work with for awhile, and it seems like she...we're going to end up doing something together. I think that's probably the Bud. I will say it was my wife's birthday this week, so happy birthday, Deepika.

Alex Lieberman: Oh, love that.

Jesse Pujji: So that's...I don't know what that is. That's somewhere...Rose, Bud, Thorn, Petal.

Alex Lieberman: Yeah, that's a hybrid rosebud.

Jesse Pujji: She's the petal. That's the petal of my week.

Alex Lieberman: I love that. Well, also when you start this new venture, to me a perfect episode to do is, how you kind of thought about her being a good person to partner with. What about her as an operator got you excited? Then also, how you guys landed on an idea that you were both excited about.

Jesse Pujji: Yeah, I can actually answer both of those briefly. I mean, I think, one, you get to know people over time, and so I've gotten to know her and see her in a lot of different contexts. The other thing I do is at any given time, I'm probably working with three or four people on different ideas. One thing I've found that's just really effective is like, "Hey, here's an idea. Why don't you go and let's go do this and let's see what happens. See what we can learn from it." And I'd tell you, having done this with six people in the last year or so, 80% just like, oh, they're busy. They actually just want to go take a job. One of my's a really soft way of experimenting, and she sent me a list of people we need to talk to. It was just clear when someone's got that energy to go build something. That's been one of the ways I've kind of vetted her and several other people over time.

Alex Lieberman: How long have you known her, out of curiosity?

Jesse Pujji: Three years. Three or four years. The other thing is, the way I did the idea is actually very simple. I have 15 ideas I'm very excited about and I just walked her through all of them and I was like, "Which one gets you excited?" She was like, "This one sounds really great." I'm like, "Great, let's go do it."

Alex Lieberman: I love it. Those were good Rose, Bud, Thorns or High Low Buffalos. I'll run through mine quickly, and then let's talk about your vacation and if you actually got to enjoy vacation.

My Rose was, yesterday was a New York City day, which I don't do that much anymore. And I started the day getting a tux for my wedding. Then I went to Times Square and we captured Plunge content and it was incredible. You see so many walks of life, and I think the highlight was, you know how there are a lot of these people that dress up in costume in Times Square? There was Mario there, Batman, Spider-Man. All these people, like dozens of characters swarm The Plunge and were playing The Plunge for half an hour. So there's a picture. We can put it in the show notes, the tweet I put out of me literally with the board in front of a dozen childhood characters, all giving a thumbs up. 

Jesse Pujji: That's amazing.

Alex Lieberman: That was the Rose. Bud is, I already mentioned it, but I'm super excited to see Jay Shetty perform tonight. I've found it remarkable to watch this guy's ascent and how just the combination of having just really basic but valuable principles, and having amazing content strategy that's allowed him to scale. This guy's done an incredible job. So I'm seeing him perform tonight. I'm excited about that.

Then the Thorn...I was between two, so I'm gonna say both of them. I got a parking ticket last night and I have to dispute it. It really fricking sucks. $65.

Jesse Pujji: How much is it?

Alex Lieberman: $65. But the worst part about it is you used to have to pay at the meters in New York City. Now they have an app that you pay with. I paid with the app. The ticket said I didn't show proper display of the physical ticket on my dashboard. But how do I get a physical ticket if you're using an app? So I'm pissed off about that and I will be disputing it and I will be getting my money back. The second...

Jesse Pujji: So young, so vigorous. I just pay them and move on with my life.

Alex Lieberman: Honestly, most things I am like that, but for whatever reason, I have a fire about this. I'm not just giving up that money. It's like my grandpa who still will drive gas station to gas station to look for which place has a 5 cent lower cost per gallon.

Then the other Thorn is, it's actually why I did, a few episodes back, the Founder's Journal-style episode on imposter syndrome, is I was feeling, this past week, imposter syndrome in the different things that I do in my life right now. I was feeling it with The Plunge because I had the thought in my head, "Shit, if this Kickstarter doesn't go well, I will have proven to myself that I am a one-hit wonder." And I kind of talked back to it to say, "All I can do is control what I can control and put my best foot forward with this." And by the way, if the Kickstarter doesn't end up hitting its goal, I'm gonna find the next thing to work on. I'm not just going to stop and put up the white flag.

Then the second thing I had imposter syndrome about was actually being the host of this show. Because I follow so many people who are just successful content creators online, and I constantly see these stories of people on YouTube or TikTok who in 18 months got to 2 million subscribers or followers. I look at a guy like Alex Hormozi, right? Alex Hormozi got to 500,000 YouTube subscribers. He has a massive audience and he's done it in the course of a year. I see these people and I'm like, "Am I just not that good at hosting content? What's going on?"

That was the Thorn this week, but it led to just kind of valuable, I would say, self-talk after that.

Jesse Pujji: Damn, I really felt that one. That's super interesting. I've never really had the...I guess what I've thought of as imposter syndrome. I've never doubted my value or ability to bring in that way, which is kind of interesting. It hasn't shown up for me that way. I think...

Alex Lieberman: It's amazing. So where do you feel self-doubt?

Jesse Pujji: I'll do the thing where I'll look at other people and go, "Oh, why aren't I that?" I'll do versions of that, but like I've never questioned my impact on a given situation, a situation I'm involved in, necessarily. That's not how it shows up. I think the other thing that I learned at some point from my coach, he calls it creative tension. And it's actually a paradigm where I was talking about for business planning and stuff I use it. I also use it for personal growth stuff, which is just desired future state versus current reality. The whole concept of it is almost definitionally, whatever you're getting today is real and what's reality, and whatever you're not getting yet that you want is of some future state you desire. One of the most common human thing is to collapse that future state in today and be mad that you don't have it. It's just like, "Well, why don't I know how to lift bench press 300 pounds yet?" It's like, "Well, you just, you're at 150. You haven't done the work to get to 300."

And so I find that paradigm generally pretty valuable, or even noticing when I'm collapsing something I want in the future into today. Because by definition, if it's not there today, it's almost like the world's way of telling you or the business's way of telling you, you're not there yet. You haven't achieved that thing yet.

Alex Lieberman: I think when I hear what you say, what it makes me realize is your self-doubting thoughts either are self-doubting based on comparison, or because you aren't at your desired future state yet and you have to bring perspective in. I think...and this is probably why you feel like you haven't had imposter syndrome, and I know for me I have, is it sounds like you don't doubt your abilities. You don't have doubt about your abilities. You just have doubt about have you achieved enough, are you moving fast enough? But you don't question, do you have the skills to do it? It seems like. Whereas for me, I would say I do at times question, "Do I actually have the ability and skills to do this? Is there this self-belief that I could pull this off?" And I actually think, by the way, so much of this, I would say 90% of this is based on a few key experiences earlier in life. I know these experiences that have just shaped me feeling defeated about my own abilities.

Jesse Pujji: Another thing that comes up for me, my coach has said this to me is, we talked about this when I was getting...he's like, "You haven't really failed all that much, Jesse." And so one version it shows up for me is it's kind of, in a sense it's more self-limiting than it is imposter. Even the bootstrapping and all that stuff. I talk about it, but I haven't actually gone for it. This guy Brett Adcock, do you know Brett? I mean, he's building computers...

Alex Lieberman: Yeah, he's gone for it.

Jesse Pujji: Humanoid computers. Sometimes I look at that and I go "Damn, I'm underachieving." Underachieving in the sense that I actually think I'm capable of that, but I won't put myself out there that much 'cause I don't want to fail.

Alex Lieberman: Yeah, you're like, "Am I taking big enough bets?"

Jesse Pujji: Yeah. There's a version of that where I'm like, wait, maybe I don't have the imposter syndrome 'cause I'm like, I choose to work on things that I know I can have a high impact. I feel confident in my abilities, versus stretching myself to the point where then I'm like, what the hell am I doing starting...

Alex Lieberman: I've had similar thoughts along those lines, and the way I've tried to talk through it is, it's not this binary thing. I would say what I'm doing with The Plunge right now, I'd call that a single or a double. Have I had thoughts about why am I spending my time on The Plunge right now, a backyard game? Yeah, I have had those thoughts, but also I've had the thoughts, I'm at this point in my life right now where I want to make sure I'm having fun with something new and some new challenge. And I know I'm not gonna work on it forever. That's why I look to put operators into the business who really will love it. But yeah, I for sure had the thought.

Jesse Pujji: The whole conversation, dude, we haven't talked much about my journey with conscious leadership, but this whole conversation is one...I mean, just for anyone listening, is it driven by ego?

Alex Lieberman: Yeah, totally.

Jesse Pujji: "Oh, am's a stupid idea."

Alex Lieberman: What does it even mean to go for the the home run swing. Who is the home run swing for?

Jesse Pujji: It's the whole conversation of whether the idea's big enough or not too big. It's all ego-oriented versus just waking up in the morning and going, "What will energize me today? What will be something I'm excited to do?" I think the more I've practiced, it's a very active practice to relate to what I'm doing from that lens as opposed to the lens of questioning the worthiness of the businesses I'm taking on, or my ability to...all of it comes from a place of fear, or in the conscious leadership paradigm, it's called below the line, right?

Alex Lieberman: Totally. Yeah. Honestly, we should do either an episode on conscious leadership or we could even, we talked about doing a book club, end up at some point rereading the, what's it called, The 14 Commitments of Conscious Leadership?

Jesse Pujji: 15. We can get my coach on. Let's interview him.

Alex Lieberman: Yeah. We should do that at some point. I want to push it forward because we have like seven things to talk about today. We've gotten through number one.

Number two is, we talked about your vacation and it sounds like you had a very lovely time in Turks and Caicos with the family. I will say, one of the highlights for me was your son and daughter talking about 60-Second Startup and my use of bad language in 60-Second Startup. That was a highlight for me.

Did you actually unplug when you were in Turks and Caicos?

Jesse Pujji: Yeah, and this is one of my unique strengths, and I've been doing it, I think, pretty much since I got married. Actually, on my honeymoon was I think the first time I did it. There's a couple of just tactical things. One is, I will generally take my laptop and I will do email or whatever on the plane ride there and the plane ride back. Kind of these really nice bookends to wind it down, respond to everything, close it all out. Then when I come back, I obviously have a bunch of stuff there to also just catch up quickly. I think that helps me sort of manage what I do in between. What I do in between is I will delete Slack, delete email...

Alex Lieberman: Delete as in you remove the apps?

Jesse Pujji: They're gone from my phone. I've also been trying to look at my phone less. I've been trying to start the day, even at home, first 30 minutes not looking at my phone. There it's even more extreme. I'm gonna go to the beach, I'm not gonna take my phone. I find that if I delete email and Slack, 95% of distractions go away. I generally will give one person on the team my hotel's contact information and I'm like, "Hey, if you need me, there is a way to get in touch with me. Call my hotel. Don't call my phone, don't talk to me." Then I'm gone. It's pretty effective.

One thing I'll say for myself is, a lot of this is for me, because I'm the kind of person that if I check email in the morning, even if I just said, "Oh, I'll just work an hour a day." For me, and everyone's different, my brain will have turned on and my thoughts will have been consumed by all these things going on. Not in a negative way, because I like it and it's exciting and it's exhilarating. But if I do it on vacation, then my day is not going to be about vacation.

Alex Lieberman: You're just not present, you're not present to your family.

Jesse Pujji: It won't be vacation. That's my way. I fully unplug and it works pretty well. Obviously I'll do a transition kind of thing when I'm back in the office. I don't put an Out of Office responder on it. I hate Out of Office responders.

Alex Lieberman: Why?

Jesse Pujji: I don't know why. I have no idea.

Alex Lieberman: I don't understand, especially you're customer-facing with Kahani. You have people you're trying to make customers. If they reach out to you, why do you make them wait for five days?

Jesse Pujji: I have no idea. I've never liked them. I just think they're annoying and stupid. I don't know why.

Alex Lieberman: Interesting. I may challenge that idea, just because I feel like you have people who think you're slow to respond, and it's just you're on vacation.

Jesse Pujji: Well, I think if someone's emailing me as a customer...I mean, my EA is in my inbox, so that's one thing that's solves for it.

Alex Lieberman: Will they answer emails throughout the week?

Jesse Pujji: She won't answer but she would route them, probably. She'll route them to somebody else on the team. Someone else on the team to handle it.

Alex Lieberman: Okay. You told me about this book that you read while you were on vacation. You were great at leaving me with a cliffhanger. I think your texts were, it was like, "Dude, this book is crazy. Chiquita just took over the government. Dude, this book is absurd. They have taken over the..." So what's the story of the book you read?

Jesse Pujji: So I tweeted out, I said, "Hey, what's a good entrepreneur bio? Somebody write one?" And someone wrote one called The Fish that Ate the Whale. It's the story of Sam Zemurray. He was a turn-of-the-century immigrant from Russia, Jewish immigrant from Russia, ends up in New Orleans. He was a poor hustler. He lived with his uncle in Alabama in the south of America, which is kind of a strange setting for a Russian Jewish immigrant. He was enterprising. He was a tall guy. They have this whole story about him. One day he's just kind of walking around and he's at the docks in New Orleans and he starts describing, he's standing at these docks and he's seeing a banana truck be offloaded. They have these huge stems and all the bananas are green, but if a banana is yellow, it's almost too ripe. It's called a "ripe" or it's called a "yellow." It's just immediately thrown away, thrown in the trash.

Alex Lieberman: That's crazy.

Jesse Pujji: Now he's a hustler. You and me, we'd look at that, and he goes, "What? You're throwing, those" He goes, "Just give them to me." This is a true story. The guy gets all the yellows off the train for free. He jumps on a different train and within three days he starts selling them as cheap as he can to local peddlers, who then sell them in the same day basically at a huge discount to the bananas.

That's how he starts his business, is literally free yellow bananas. This is like in 1910 or something like that. The guy's 20 years old. By the way, it gives you the whole backdrop, which I didn't know and appreciate at all about the banana business. Bananas are not native to North America. They're completely a business capitalism invention. Nobody ate them in 1890. Some entrepreneurs were like, "Ooh, this fruit ships well, it seems tasty. I'm gonna bring it in. I'm gonna sell it." Next thing you know, they're handing them out at Ellis Island to every immigrant, saying, "Welcome to America, here's a banana." Today bananas are the largest item sold in the United States, by the way, by volume.

Alex Lieberman: Of any grocery item?

Jesse Pujji: Of any item. The most volume of units is bananas. Look up Walmart. That's what they sell the most. They're completely an invention of American entrepreneurship and capitalism.

The big company he bought it off of was United Fruit. It kind of gives the history of United Fruit, which was just some guys who went into the jungle in Guatemala, planted some bananas. They learned about this fruit. They're like, "We should bring this to America." The entire bringing of the banana was an entrepreneurial exploit. They give that history, which was super fascinating. This guy becomes a hustler. He becomes a guy optimizing everything. He starts, he goes, "You know what? Let me buy some land and grow my own bananas." He's like, "I want to move upmarket but I'm faster. I'm better. I'm smarter." He starts growing his own stuff in Honduras. He's timing how long it takes you to pull the stock to how long it puts you...they'd send time and reports. They would send reports back, just like analysis...

Alex Lieberman: He's like an operational junkie.

Jesse Pujji: Operational junkie. He's like living in Honduras. How do we cut the plants? He changed the way fertilization worked. Like every lever you could imagine to optimize. He just starts buying he ends up owning 40% of the land in Honduras, the non-private land, through this business called Cuyamel.

And this is what I was texting you about. There was some crazy trade agreement between England, the United States, and Honduras that would require Honduras to start taxing exports, which would basically destroy his margins if he had to be taxed. He had a "concession," read bribe, with the government in place of the localities to not have to pay that because he was investing so much in whatever he was doing.

Alex Lieberman: The tariff already existed, or he...?

Jesse Pujji: It didn't exist. The United States government went in and the State Department of the United States said, "You know what? We're gonna make you pay a tariff." Because they owed money to England. Whatever, some crazy situation. He goes to the Department of State or US Secretary of State and goes, "You guys can't do this. It's gonna ruin my business." Secretary of State's like, "You dumb banana guy, get outta here."

Literally, he goes, "I don't care about your banana business. This is government stuff. It's really important that we resolve this issue between Honduras and the United Kingdom."

The reason they want to resolve it, by the way, was they didn't want the United Kingdom to actually come and collect their debt with soldiers because the US wanted to maintain full control of our hemisphere. They didn't want a European power getting in. That's why the United States was getting itself involved in this. So he goes, "Well, if that's the deal, sure, whatever you say, Mr. Secretary of State." He raises a private army and he finds a guy who used to be the president of Honduras. He says, "I'm gonna back you." And he overthrows the Honduran government.

Alex Lieberman: That is absurd. But how did that help him?

Jesse Pujji: He literally invades...well, because then his guy was in there and then basically his guy's like, "I'm not doing this deal with US and the UK."

Alex Lieberman: So he successfully overthrew the government with a private army?

Jesse Pujji: He completely successfully ran a coup on the government of Honduras, okay? This is the third ending of the book, by the way. The book goes on. So then eventually there's all this beef between him and the...he's beating the pants off of United Fruit, which is the big guys. They start having literally local skirmishes of their own armies inside of Guatemala and other countries. The US government, the State Department and the Justice Department get together. Justice Department wants to regulate them from not becoming a monopoly, but the State Department's like, "This is causing too many issues." So they get together and they go, "You guys have to merge." So he merges; he sells all of his shares. He becomes effectively a billionaire in today's money from selling his banana business to the big business. That business proceeds to get run into the ground.

Alex Lieberman: Is he still involved at this point, or no?

Jesse Pujji: He's a huge shareholder. He's like the largest shareholder, but he's going to do philanthropy, blah, blah, blah, whatever. They run the business into the ground. He goes, "Guys, what are you doing?" He starts writing them letters. He goes and visits the board. The board is like, you're just a fruit peddler. You don't know anything. He goes, "I'll show you." He goes around and gets proxies for all the other shareholders. He walks into the room in Boston and he fires the entire board and C suite, and he goes, "I'm in charge of the business now."

Alex Lieberman: The banana guy is a baller.

Jesse Pujji: Dude, he is. And then he grows the whole business back up successfully. He makes it into this huge thing. It ends up owning 70% of the land in Guatemala, 40% of the land. It's such an amazing story. He then...

Alex Lieberman: By the way, is it Chiquita? Is that the company?

Jesse Pujji: It eventually becomes Chiquita. There's a whole thing of how it kind of gets too big for its own good. He basically builds it. The two other things I'll say, and then I'll stop. It's just such a cool story. One is, he was critical in forming the state of Israel. He's like a Zionist.

Alex Lieberman: Why? How?

Jesse Pujji: Because Israel was...the whole book is told in this angle. I don't know how much of this is the angle versus reality according to the book. There was a United Nations vote. Obviously terrible things had happened, the Holocaust had happened, American Jews were super concerned. The way the book frames it, which I believe is, Jews basically realized they weren't safe anywhere. It didn't matter. Like if a state turns on you, you're done. So they had to have their own state. They go to United Nations, England. Everyone's a little on the fence about it. They go, we need a vote and two-thirds majority. The first vote takes place. It's 50/50. It's not enough to create the new state. Well, guess what? He's one of the most powerful men in South America, in Central America. He calls these heads of state and he goes, "You want to keep your job? You need to vote for Israel." He literally gets these guys, he gets 10 presidents to vote in the United Nations.

Alex Lieberman: That is wild.

Jesse Pujji: To support Israel. So that's...

Alex Lieberman: Is it crazy how these people exist and no one has heard of him?

Jesse Pujji: Dude, it blew my mind. The last thing I'll tell you is, the last part of this story, well, there's other parts, but I'll stop. Communism starts taking place after World War II. United States government is super freaked out about communism and the company he's now running, which is the 70% monopoly of bananas, this is all bananas, by the way, still. It owns 70% of the land in Guatemala. Some guy comes in to run Guatemala. There's regime change there. This guy is at worst, a terrible communist and at best, very sympathetic to communists. They own 70% of the land; they start taking his land away. They start taking the company's land away because they're communists. They're like, "No, no, you can't have that land. We don't want you capitalists here." So he goes to the US government and he goes, "There's communists there." He hires this famous PR guy who goes around and scares the Senate and the Congress to basically say, "We need to overthrow the Guatemalan government." So then again, he does the same play he did in Honduras, except this time the CIA is involved and the United States government with his votes and they go and they overthrow...

Alex Lieberman: That's absurd. How is this not a movie? This is crazy.

Jesse Pujji: It should be, dude. They overthrow the Guatemalan government. Officially, the CIA did it. But basically they said the meeting would be two people from the CIA, one person from United Fruit.

Alex Lieberman: So just to summarize everything, this guy who started his business by grabbing already-ripe bananas that were being thrown out. He then ended up owning 70% of the land in Honduras, and he successfully created the state of Israel and successfully was behind two successful coups of governments?

Jesse Pujji: Yes.

Alex Lieberman: That is fucking ridiculous.

Jesse Pujji: I think the other sides of it, I think people say this is the "ugly Americans" concept. This is why people hate America outside of it, because of things like this. It was very abusive and exploitative, whatever, according to various reports. In some ways capitalism at its best and's entrepreneurialism, but it was very, very aggressive capitalism at a different time, which wasn't cool. The other thing they do reflect on is his family, not entirely, but parts of his family were kind of a shitshow because he was never around. He was in Honduras all the time.

It does tell the entire arc of his story, but to your point, I'd never heard it. It's very entrepreneurial and there's real examples of how they would time each part of the process and cut down the seconds, how that would play into margins, and just all the innovation and smart things that he did around the trade. It's a very entrepreneurial story in addition to just a wild tale.

Alex Lieberman: Yeah, and I think based on that last piece you just said, at the end of the day, not to say that every uber-successful entrepreneur that we look up to in society, whether it's the Elons of the world or Steve Jobs of the world, Bill Gates of the world. Not all of them have it to this extent, but where you basically said, he had issues with his family. With any of these stories, there are parts you can admire of this story...

Jesse Pujji: Totally.

Alex Lieberman: ...without admiring the entire person or every part of their life. I think the part of this guy just having...

Jesse Pujji: Yeah. I watched Super Pumped on Showtime, and I had the same feeling of, on the one hand, I was like, this guy is relentless. Then the other part was like, man, this is a very troubled person.

Alex Lieberman: That is a crazy story. So would you recommend it to listeners?

Jesse Pujji: Absolutely. It was also the perfect length. It was like a five-ish-hour read on the beach.

Alex Lieberman: Oh, that's amazing.

Jesse Pujji: Yeah, it was great.

Alex Lieberman: Okay, we are going to hop to the break so you can hear a message from the folks that pay the bills. Then when we come back, we are going to talk about a founder I met the other day, and we're gonna analyze his business and then finish with a Startup AMA. Be right back.

Okay, we are back from the episode. We just had a wild conversation around the banana billionaire who overthrew two governments and started the country that is Israel. Now I want to talk about a founder I met yesterday.

Jesse, I want to break down his business for you. Then I want us to just riff about what we like about this business, what we'd be wondering if we had to analyze this business as if we were investors or we're analyzing a stock.

I mentioned at the top of the episode, my Rose for the week was I spent three hours in Times Square yesterday shooting content for The Plunge. I shot that content with this guy named Arjun who is building an interesting business. The business is called Doola. And the way they describe themselves is it's a business in a box. They do everything from formation, starting your business, to taxes. They're doing banking now. They create virtual mail, so a virtual address if you don't want your home address to be online, et cetera. 

And so when I was starting The Plunge, I hadn't started a company in eight years. Most of these tools that are around now, whether it's like Mercury Bank or Ramp, these weren't around when I was starting the Brew. I decided to use Doola because I saw this this guy Arjun's content online and thought it was interesting. Their whole goal is to create the operating system for entrepreneurs. Basically you have one place for running your business. I used the product, I created my LLC with it. I thought it was very smooth. It was done within a day. I hit like five buttons. Their wedge product was LLC formation specifically for non-US residents. Their key insight was that starting a company as a non-US resident is particularly difficult and there's not one place to do it, and everyone does it with a lawyer or tax advisor that you find from a friend.

So that's what they started with. By the way, I think the reason they did that is they'd gotten into Y Combinator with a product originally that was like TikTok meets email. So it was like asynchronous communication, but done in intimate video form. It was a non-US company. When they pivoted into Doola, they had to switch from a non-US entity to a US entity. They ended up having to pay lawyers like $30,000. They were like, "There's no way this is how it should work."

So they came out with this formation product, then they introduced taxes, where their tax product will do your business taxes every year, and then they have banking. Just to give you the numbers on the business, if you want formation done, you pay 200 bucks. When I had my LCC made, I paid 200 bucks, and then they try to upsell people on taxes, which is $2,200 a year. The business 8xed in ARR in 2022. They're doing, let's just say, mid-seven figures of ARR. Their kind of big vision is they want to basically be the Intuit of startups. You know, Intuit now owns Mailchimp, Credit Karma, TurboTax, Mint. They want to be the suite of products that people go to for formation banking, taxes, mail, insurance, and more.

What's your initial reaction to this, or questions you have?

Jesse Pujji: I met this guy and I think I had a chance to invest, and maybe I'm an idiot if I didn't.

Alex Lieberman: Oh, you met him?

Jesse Pujji: I met him awhile ago. I'm like, looking at my email right now.

Alex Lieberman: He has great hair. That was my first reaction when I met him. 

Jesse Pujji: January of last year.

Alex Lieberman: That's so funny.

Jesse Pujji: I think they were just getting off the ground. He was asking me a bunch of questions about growth and customer acquisition, of course. Well, audiences told me this, they want us to be more critical and more dickish. So I'll mix in a little bit.

Alex Lieberman: Let's hear it.

Jesse Pujji: I love the trend. I'm a big believer...

Alex Lieberman: The trend of what?

Jesse Pujji: The big mega trend, the "So what?" or the "Why now?" Being the amount of new businesses, especially what I think of as solopreneurs, creators. It's exploding and going to continue to explode. I love that sort of the market trend behind it that there's a rising tide. I think it's critical to grow the business. I think the problem they're solving, A), it's not a new problem. I mean, LegalZoom was a multi-nine-figure exit or something in the first internet era or whatever. I use LegalZoom for...

Alex Lieberman: Which, by the way, is a crazy story. We should tell the LegalZoom story another episode. It's crazy.

Jesse Pujji: Robert Kardashian is the first...

Alex Lieberman: Yeah, exactly.

Jesse Pujji: One of the first Kardashians. So I think that's not a new business by any means, in the sense of the idea. I think if you could solve the problem...when I talked to him, and I mean, he's changed this and you experienced it, is like, if you can solve the problem to truly make it, "takes me five minutes and you do 10 hours of work for me," that's amazing. I think it's much harder than it sounds to do that, just given the legal parts of it and whatever. The dream of the Stripe-type version of this, which is literally just a little piece of code you can insert and immediately get your thing up and running, I think would be amazing. I mean, Stripe is trying to do it too, with Atlas. They have this other product. I think I'm like, the product difficulty feels hard to me.

Then of course, what he talked to me about, which is always a lot of things like this, is like can you make the economics work from a customer acquisition standpoint? Which is really, it's an execution problem. It's an execution problem. Can you run ad campaigns so that you guys did it at the can acquire whatever the customers are in a way that the LTV is better than the CAC by multiple...and I don't think that's impossible. I don't think it's easy, either. I think it's somewhere in between.

Alex Lieberman: Very interesting thing he told me, which I'm sure you won't be surprised with, given how well your threads on Kahani did for user acquisition for Kahani, is a very significant percentage of their user acquisition every month comes from his content he creates on Twitter.

Jesse Pujji: Yeah. I mean, GrowthAssistant. Yeah, exactly. So there you go. Maybe I'll take credit, maybe I told him to do that. I think that was a time when GrowthAssistant, it was crushing it. I mean if you can find a cheap source of customers like that on Twitter, I think it's definitely a massive head start to get you up and running. There's a whole servicing question I'd have for him around how do you actually, is it programmatic? Do you actually have people in the background, like taxes...taxes are...

Alex Lieberman: To that point also, I think that's a big thing they're trying to figure out, because they talk about LegalZoom a lot. The issue with LegalZoom is it's so human capital-intensive because of the servicing. Their whole thing is how do they do this, but with a quarter of the head count?

Jesse Pujji: Right. I think part of that is you have to get probably more narrow on the specific services. If you were doing a two by two or matrix of their business, you'd say, what service is critical, expensive that you can make cheaper, is time-consuming if you do it yourself, but there's a way to actually cut that time on the back end. If I were in their shoes, I'd say find...maybe that's LLC creation, I don't know, whatever it is, it's one of those functions. Then stop trying to do a bunch of things. Just go do that. I don't know how many, there's 3 million corporations incorporated every year or something insane like that.

Alex Lieberman: At least.

Jesse Pujji: Go get 10,000 of them or a hundred thousand of them. I think that's another entrepreneurial mistake that a lot of people make, I've made, I'm sure you've made, is we immediately start going wide, and every well is way deeper than you think it is. There's way more water at the bottom of it. I think part of it is, that's the other fear I would have for them is like you said three things just now. I'm like, dude, those three things sound like a lot, and sound hard to scale.

Alex Lieberman: I think their view on that is they think formation, helping you create an LLC, is commoditized. Their fear is a lot of other people can come out with an LLC formation product. And also, it's a one-time fee. You pay the 180 bucks. I'm sure what's in the back of their...I'm sure two things in the back of their mind are, "Okay, we have these 10,000 businesses that formed LLCs. Are we not going to extend the value of these people at all?" Slash, they're going down the venture treadmill. I think for them, they're also saying, "How are we raising at a 10x on revenue, not at a 3x, and it's going to be a 3x if you're just doing one-time formation payments."

Jesse Pujji: That's another thing I would say, like the venture track. This is a great example where the venture track can let the tail wag the dog. Look, by all means, if you want to go build the Intuit of startups, god bless you. If that's truly what you want to build, then you should go raise money. You have to build all these techy things. There's a company called Collective that's doing a version of this too, started by an experienced entrepreneur. But I'll just say this, if $200 or $300, if you're acquiring customers at zero and they're incorporating your LLCs through you, there ain't nothing wrong with that. Dude, I mean go do 10,000 of those. 

By the way, part of it is, the fear of commoditization of business is totally driven by venture. It's not driven by entrepreneurs. Because every business, you can build a mode around over time and you can build some resilience. By the way, part of it I would tell them is, first get 10,000 a year of those LLCs being created through you profitably. Guess what? Now you have a balance sheet, you have cash coming in the door, you can go and figure out how to get taxes to be done well. You can still raise venture if you want, but I think what ends up happening again with venture is the well gets dug very shallow for the story's benefit. You go tell the story, then you don't actually have a deep value prop. Then a storm comes, and guess what? The hole gets filled, as opposed to dig...if you became the best in the world at LLC incorporation, I don't know if it's a huge business, but there's a meaningful business that would generate cash and open up a bunch of additional doors.

Alex Lieberman: And by the way, you could probably end up raising money, because you now have hundreds of thousands of people who have formed a business with you that you have relationships with. And by the way, you have probably a lot more leverage because you're actually cash flowing a ton.

Jesse Pujji: Let's do the math. At 300 bucks a pop, 10,000 things, a thousand would be $300,000...

Alex Lieberman: $3 million.

Jesse Pujji: Yeah, $3 million. So you're talking about at least a million in EBITDA coming out of that business, maybe more. There's nothing wrong with that.

Alex Lieberman: It's not recurring revenue per se, but going back to the trend you're talking about of 3 million businesses formed a year. If you can have some level of predictability or confidence that you can convert x percent of all businesses that are formed in a given year...

Jesse Pujji: Yeah. The real business I would do is SaaS Pass. Remember we talked about SaaS Pass?

Alex Lieberman: Yeah, totally.

Jesse Pujji: I would get these guys to incorporate through me and I'd go, "By the way, now I'll sell you this thing for a thousand dollars and you'll get a discounted Dropbox and QuickBooks." That's how my thinking goes.

Alex Lieberman: Okay, so I'll just share a few final thoughts on Doola, and then we have a Startup AMA and you're the perfect person to answer this question; I'm not even going to try to answer it. On Doola, the things that I like about the business is I generally believe...and you've seen this firsthand now, so you could make the decision on if you think I'm right. I generally believe that it's easier to build a B2B business than a B2C business. I generally believe that getting businesses to pay for things is easier than consumers.

I like that Arjun, one of the founders, is very public-facing and is creating a ton of content and he's trying to become Mr. LLC. Like that is what his bio says. He's kind of pulling the Andrew Gazdecki card, of being like Andrew Gazdecki has turned MicroAcquire into a verb. He's trying to do this for LLC.

I think this business could have amazing channel partnerships, because there are a ton of huge businesses out there that require you to be an LLC in order to use them, whether it's Shopify, whether it's Stripe. So what if they partner with these companies where you go to Shopify, you go to create your store, you don't have an LLC yet, and you can just click a button in order to set it up in Doola.

Rambo, chill. One second. Rambo, go. One second. Car, can you take him? Just take him, please. Please. I know, but please just take him. Please, just take him. Thank you.

We can keep all of that on the final recording.

So in terms of channel partnerships, I think, like a Shopify, it's in their best interest to get someone to set up an LLC so that they can start a store. Like you said, I think entrepreneurship is on the upswing, and I think they can monetize in a bunch of different ways. If they bundle, I think they can partner with companies on different parts of their bundle they don't have yet. Say, partner with Ramp for like CFO software and they could get paid affiliate money to send traffic to them. And if it's a big enough channel, they just create that themselves.

I think my biggest skepticism is, I don't know if the venture route was right for them. It's not a winner-takes-all market. I just think, to your point, I think for the business they're in, it could cause them to go super wide too soon. I wonder how well they're converting transactional clients into subscription clients if that's what they really care about. And I just don't know how much...people talk about how bundles really create a moat and I see how that works for certain businesses. For Apple, I'm never leaving Apple because everything they add, I'm locked into their ecosystem, because everything talks to everything. Or Salesforce, I get it. But for this, I just feel like there's actually a perverse incentive, where as you become big as a company, your needs become more bespoke. So you have taxes, you bring an in-house accountant in, or you go up upmarket with banking to JPMorgan. So that's my biggest question, is how strong the bundle actually is for them.

Jesse Pujji: Makes sense. I think one thing he could do, and I've thought a lot about this category for us, even at Gateway X, is build the product specifically to a type of business. So for example, like influencer LLCs. That's it. And then you actually really think about that customer and solve their the way, they don't have the issue of getting too big. Most of them don't, and by the way, they have a lot of other things do they do workman's comp insurance? There's all these other issues that pop up for them as individuals slash business owners who are running kind of their own little small business. To me, that's like how I would probably try to build moats, is make the best solution for a specific customer segment.

Alex Lieberman: Totally. Okay, 60 seconds on Startup AMA. The question from our listener is, "The most pressing challenge I'm having in my business is generating my first few B2B SaaS sales. I don't come from a formal sales background, and I'd love to hear what stories you guys have or what tips you have for doing it before you have a personal brand like you have. So if you don't have a network or a brand, you have a B2B SaaS business, how are you trying to get your first sale?"

Jesse Pujji: Well, I think you said "if you don't have a network." I think everybody has a network. Let's start there. It doesn't matter how big or how small it is; you have an uncle, you have a cousin, you have a teacher. In the early days of ambush, I was 25, I had worked at a few companies and stuff and I just started going to my targets. Who do I want to meet with? Just figuring out the chain.

I used to do this with girls when I was a teenager. "I like her. Okay, my friend knows her and my friend knows...what class is she in?" So the same exact thing with B2B prospects. Figure out 10 conversations you want to have, and you beg, borrow, and steal to get in the room with those people. Obviously that means, build out your LinkedIn and connect with all your former colleagues from wherever and your family. It kind of means you gotta ask around when you're in random things and random conversations. There's nothing wrong with cold emailing. Cold emailing, if you're very earnest, especially if you're a student or you're young, most people will take the phone call if you're just honest. "Hey, I don't know what's going on with my business, but I'd love to talk to you for 15 minutes." That's the other one I'd do, is cold email.

I think the best thing is just work introductions through whatever network you have, as small as it might be, to try to land those five to 10 conversations. The other thing is, early on when I do this, always framing it as a...when we launched GrowthAssistant, the first 30 calls—by the way, half of which resulted in sales—were not...and we weren't being disingenuous. I was like, "Hey, we're gonna start something new. Would love your take on this concept. Is it interesting?" We were genuinely trying to learn and get advice. We were like, "Can you introduce me to someone else?" "Oh yeah, oh yeah, you should talk to Bob about your business." If you're earnestly trying to do that, I think you'll end up opening a lot of doors, as you try and get more sales.

Alex Lieberman: People just feel a sense of ownership when something's early and new and exciting. They feel like they're almost co-creating the business, and it makes them want to tell other people about it.

Jesse Pujji: Totally.

Alex Lieberman: I love it. Awesome.

Well, this was packed with a potpourri of different stuff today, from the banana king of the world to how Jesse truly unplugs on vacation, and Doola, which is a business in a box.

Thanks, everyone, for listening, and we'll catch you next episode of The Crazy Ones.