Shaan shares two investments he passed on — Jenny AI (an essay-writing tool for college students) and Flo (the women’s period tracking app) — and breaks down why he missed them and how each company found product-market fit. Sam riffs on the Hostage Tape founder who proved him wrong, then both hosts wind down with a wide-ranging conversation about authenticity, Jason Kelce, and Tracy Chapman.
Speakers: Sam Parr (host), Shaan Puri (host)
Introduction: Two Investments Shaan Passed On [00:00:00]
Shaan: All right, what’s up everybody. Back to the greatest podcast of all time — My First Million — where we talk about business ideas, businesses that are under the radar and crushing it that you haven’t heard of. Hopefully when you listen to this podcast you get a little inspiration, a little wind in your sails, so that you go out and kick a little more ass today.
Shaan: Sam, I have an ass-kicking story for you. You want to hear it?
Sam: I love ass-kicking stories.
Shaan: In fact, this is two of them. It’s stories of other people who are kicking ass, and it’s a story of me getting my ass kicked as an investor. Here are two investments that I passed on for two totally different reasons. I’m going to tell you the reason why I missed each one and the really cool story of what these companies did.
Jenny AI: The Essay-Writing Tool for College Students [00:00:45]
Shaan: All right. So the first one — two or three years ago, two years ago I think it was — there’s this guy David, and he’s pitching me a startup called Jenny AI. It was at peak AI time, so this is 2021. GPT-3 was out, everybody was excited about AI, and this guy had yet another AI startup idea. I didn’t really know what to make of it. It was small — it was only doing $2,000 a month in revenue. So he’s like, “Hey, we’ve got great traction, I’m at 2K MRR.” And I’m like, “That’s cute, son. The pool guys make 2K MRR. Come on, we’ve got to do better than that.” But really nice guy — we get on a call.
Shaan: I don’t remember what I said, but he told me afterwards he was like, “Yeah, you were one of the nicer people in terms of giving feedback.” At the time they had a pretty undifferentiated product. What they were doing was a product called Jenny AI, and what it did was it was a writing tool — basically just like Jasper. You’d say “I need a blog post” and it writes you a blog post. You need SEO content, email content, blog content. It was just writing blogs for you. There were a bunch of startups doing this at the same time, Jasper was taking off, so it was a hot space. But I was like, “Dude, I think you’re late to that party.” And he’s like, “No, no, no, we’re gonna make it.”
Shaan: I liked the guy. He’d told me that at age sixteen he’d basically started being an entrepreneur — tried to build a t-shirt company, failed. But you know, that’s a right of passage: start your first terrible idea, get that out of the way. And now he was on to this.
Sam: How old are they when they start working on this?
Shaan: About 24, I think. He’s got no money. He’s living in his mom’s house. He’s literally like, “I have to ask my mom, ‘Hey, can I get the credit card? I want to get Chipotle.’” And she didn’t make him feel bad, which I respect. I know she probably felt bad because, you know, Asian parents — all their kids’ friends are at Stanford, getting promotions. He’s still in the bedroom. And 24 is the threshold where it’s like… cute transitions to concern.
Sam: Yeah, exactly. Endearing to concern.
Shaan: Exactly. She’s like, “I don’t know, he just keeps saying ‘thanks for hopping on the call’ but nothing seems to happen.” He’s pitching people all day in his bedroom and it’s not working.
The Zoom-In Pivot: Niching Down to Essay Writing [00:03:30]
Shaan: But he makes a pivot — and it made a lot of sense. I call it a niche-down zoom-in pivot. A zoom-in pivot is when you basically say, “I have this thing today that’s kind of meh for everybody, but maybe for one set of people it’s awesome.”
Shaan: This is actually the same way Twitch started. Justin.tv was a grand vision — broadcast anything. Broadcast your life, your backyard, a sports game, a video game. Only 2% of it was people broadcasting video games. Twitch was a zoom-in. Justin.tv was failing and they said, “What if we just did the video games thing?” It sounds counterintuitive — well then we’ll be too small, it’s only 2% of our current traffic. But it had the potential to be quite big once you specialized the product.
Shaan: These guys did the same thing. They did it around college students who need help writing essays. Specifically not like “it’s one minute before the deadline, just give me a full essay so I can trick my teacher” — it’s actually more like a writing assistant. So you’re writing your essay, and you don’t just say “give me an essay about the Industrial Revolution.” You start writing your essay and it kind of autocompletes — like autocorrect — it suggests what the next couple sentences could be. It helps you cite stuff too.
Shaan: So you’re writing something about, say, the effects of the ketogenic diet on human longevity, and it’s like, “Hey, by the way, do you want to cite this paper that’s already mentioned this?” And it auto-generates the well-formatted citation at the end. Or it’ll run a plagiarism check for you — it’ll be like, “Hey, let’s just make sure this isn’t copying what’s already out there, because your teacher’s not going to like that.” So it has a couple of specific tools. It’s not like ChatGPT where it’s just a chat interface — you click buttons and select how you want it to help you.
Sam: You know how Microsoft used to have Clippy?
Shaan: They just need a little picture of Bill Ackman that says like, “Ah, ah, ah — that’s plagiarism.”
Sam: Exactly! Billy Ackman would be perfect.
Shaan: He told me that at the end of the essay, less than 30% has been written by AI — so 70% is written by the student and 30% ends up being filled in by the AI.
Shaan: Okay, so he gets this idea. But even still, how do you know if this is gonna be successful? He pitched me two years ago at $2,000 MRR. It’s currently doing $300,000 MRR — $3.6 million a year. In fact, last year he had an offer to sell the company for three million bucks. He thought about it — “Oh my God, I could be a millionaire, I could have $3 million, I’m young, I’m in my early twenties.” He turned it down. And now the company’s probably worth $10 to $15 million. So in six to twelve months he basically tripled the value of the company.
How David Park Got His First 100 Customers [00:07:15]
Sam: How did he make this big? The startup survival mode — he was probably just floundering, but he didn’t have any expenses, so he was kind of default dead. Not even in startup mode, just his life.
Shaan: Well, actually, Jason Calacanis’s incubator, Launch, gave them $100K, just like over email — “Here’s $100K.” So then they moved to Malaysia. Like, “Cool, this will last forever here.” He’s like, “Let’s just make this $100K last as long as we need to survive.” They did end up raising more money — another $800K later — but how did they make this big?
Shaan: So I wanted to share a couple things. He’s like, “We do the obvious things, we post about it, whatever — it’s not really going anywhere.” But then there are three interesting inflections for this business.
Shaan: Inflection one: he does the stuff that doesn’t scale. He goes and fights for that first 100 customers with hand-to-hand combat. The overall strategy I’d call “influence the influencers.” He starts joining Facebook groups. He wrote a long Twitter post about this — you can check it out. So he joins a group of like 10,000 people, and he’s like: what you cannot do is join the group and then immediately post about your thing. It just gets taken down or flagged as promotion.
Shaan: So he thinks: in what situation would this be well received? It would be well received if the moderators and admins liked me — if they were rooting for me, if they’d already used my product, if I was a familiar face in the community, if I was adding value, and even when I did post it was for feedback and not “buy my thing.” So he works backwards from there.
Shaan: He joins the group and starts posting helpful content. In a Facebook group, the bar is pretty low, right? Nobody’s professionally trying. People are casual — most people don’t do anything at all. This would be a Facebook group for researchers, for college students, for grad students, for anything he had a hypothesis about. So he’s like, “I think this works really well for grad students.” He joins a school’s grad student group with like 6,000 people.
Shaan: He starts making helpful posts. He’s visible, he’s helpful, people start to see him as a regular. He’s a regular at the bar. Okay. Then he hits up the admin. The admin’s like, “Oh, you’re one of the regulars — yeah, sure, what’s up?” He’s like, “Hey, I wanted to get your feedback on something. Would you be down to do a 15-minute call? I know you talked about this in a previous post. I think I actually have something that can help you.” And the guy would be like, “All right, sure, I’ll do it.”
Shaan: So he gets on the call, he shows him the product, and he’s like: “I’m not gonna promote this until I see the eyes light up. If the core power users don’t like it, the casual guys aren’t going to like it. So I’m going to keep iterating until those guys are like, ‘Yeah, this is actually awesome,’ and I see that they’re using it after the call on their own.”
Shaan: He told me, “I read the Mom Test, like you guys said — these guys are fans of the pod — so I learned how to do customer calls. I’m doing the calls, I’m finding out their pain points, I’m building a product that solves them, and then I’m seeing: do they use it organically afterward?” Once they did, he’s like, “I got him.”
Shaan: So then he’d let them use it for a couple weeks. And then a week later he’d circle back: “Hey, I took all your feedback and I made the product better.” That’s a key part of winning users over — making them feel heard, making them feel like you actually acted on what they said. Finally he’d be like, “Hey, do you think I could post it in the group? Do you think other people would like this?” And they’d say, “Yeah, for sure — actually I’ll post it for you.”
Shaan: So now you get the cosign from the group admin — the person everybody knows — saying, “Hey, this is awesome, I’ve been using it, the founder’s in the group, if you have any questions check this out.” And you start getting a bunch of traction. So you get the first 100 customers through this very manual process, which was really not as much about getting customers as it was about getting the product right by winning over the customers.
Sam: This is very similar to you doing the first hundred calls with Hampton members, right? I called it the zebra calendar — just stripes, just 20-minute calls all day.
Shaan: I did that with Reddit too, by the way. When The Hustle first got popular — I posted on Reddit and I did the same thing. I wasn’t as eloquent as he was, but I basically did 10% self-promotion, 90% add value. You start getting a reputation.
David Park’s Lucky Breaks [00:13:30]
Shaan: Did you see that there’s a movie about the roaring Kitty guy? The real person is like a really good-looking, charismatic guy — he looks like he could be an actor. I’m looking at David Park doing this video and I’m seeing how he dresses, and I’m like, this guy looks like an actor playing himself. This guy’s got the it factor. I can’t even hear him talk but I can just tell by his body language, how he dresses — this guy’s got charisma.
Sam: J-haircut guy?
Shaan: Yeah, yeah, yeah. This guy looks like the actor playing him. He’s one of those people where if they wear clothes that don’t fit, it looks good. But if you wear clothes that don’t fit, you look like an idiot.
Shaan: Now let me tell you about phase two: get lucky. We’ve done the four levels of luck before. The first is dumb luck — lightning strikes you. The second, fortune favors the bold — he’s taking a bunch of action and putting himself in a position to get lucky.
Shaan: Two lucky breaks happen. The first is this guy Zain, who runs an AI newsletter — I think it’s called Superhuman or Superpowered, something like that. He does this Twitter thread called “10 websites so useful it feels almost illegal to use them” — that kind of thing. And this thread goes so viral. Guess how many likes it has.
Sam: 10,000?
Shaan: 365,000. Dude, I could post a sex tape and not get 365,000 likes.
Sam: I think I probably wouldn’t get any either.
Shaan: You could release a sex tape and no one wants it — that’s the worst-case scenario.
Sam: How many users did he get from that?
Shaan: He’s like, “Dude, every minute I’d get 10 customers. It was just insane.” So he gets this huge boost — 10x or more. He was at $2,000 before that, now he’s in the tens of thousands of monthly recurring revenue.
Shaan: Then — Jennifer Lopez does a commercial about AI with Virgin Air or something, and in the commercial she’s like, “Oh, I’m not Jennifer, this is Jen AI.” So Jenny gets a bunch of searches, and he’s the number one search result for “Jenny AI.” He’s like, “I got a bunch of free traffic from that.” But he’s still like, “I don’t know what to do to really blow the top off this thing.”
Breaking Down the Jenny AI TikTok Ad [00:17:00]
Shaan: So then they start posting TikToks. This is what I want to ask you, Sam. You did a great job early on with The Hustle. You basically were like — instead of just saying “here’s my newsletter, please read it” — you were like, “My boss thinks I’m so smart, but what he doesn’t know is I just read The Hustle every day.” It had that value-based hook: what is the happy ending for this customer? It’s not that your newsletter’s great. It’s that your boss thinks you’re smart.
Sam: Yeah. “My boss thinks I’m smart. I’m not. My secret weapon is The Hustle, which I get every morning.” That was the ad. And I stole that from somebody —
Shaan: I wouldn’t say stole.
Sam: I would say I was heavily influenced by a random ad I saw from The Skimm, and I changed it — and now everyone else has since stolen it.
Shaan: A jury of our peers would say that. So if you had to do an ad right now — a short video, a TikTok — to promote Jenny AI. Let’s brainstorm live. How would you design it?
Sam: Okay. I think I would steal that same premise — “my teachers think I’m brilliant, but I’m really just using Jenny AI.” But video is harder. All my ads were text and a photo on Facebook. To do this on video, that’s what young people are great at and I’m really bad at. What would you do for the video?
Shaan: I would do that same premise but — watch this. This TikTok has four million views.
Shaan: The ad basically takes a different format, which I’ll call the “relatable struggle.” It starts: a girl at Starbucks — it doesn’t look like an ad, that’s the first thing you need to know. Nowadays, if you want ads to work, don’t make them look like ads. As soon as I see an ad I’m instaswiping away. So this needs to be relatable. It looks like a college girl at Starbucks and it says: “doing an essay last minute, my goal is to submit before 12:00 a.m.” It’s done two things: relatable problem, and established stakes. Will she make it or won’t she?
Sam: It’s a door-closing, Mission Impossible thing — you gotta slide under the door.
Shaan: I’ve got about $15 million in ad spend under my belt. I’m going to say something that might sound horrible, but here’s the truth: women who look approachable — not model-beautiful, not too fancy — get higher click-through rates across all demographics. I’ve always had a higher CTR with women. They have to look like someone you could actually approach, like you could have a conversation with them — but aspirational. If they’re too polished or too fancy-looking, it doesn’t work. It has to be an approachable young woman. They did that wonderfully here.
Sam: I love the level of nervousness in your voice as you’re trying to say this without getting canceled.
Shaan: I’m gonna call it “next-door hot.” Next-door hot always outperformed like beautiful or model or runway hot. So that’s frame one: relatable struggle. And it says: current time, 10:20 p.m. “Last-minute research.” Then it says: 10:50 p.m. “Mental breakdown” — and she’s crying. So now you’re like — is this going to be funny? Is this going to be serious? You don’t know. We’re ten seconds in with no hint this is an ad for anything.
Shaan: Then: “coffee and TikTok break” — relatable. Then: back to it, hair gets clipped up. Another relatable humorous moment. We’re now 30 seconds in and there’s been zero mention of the product. This does two things: the TikTok algorithm loves it because you’re watching the full video instead of swiping away, and you’re invested — you have sunk cost. You need to see the ending. One of the top comments is, “For a second when you showed Jenny AI I was like, I got bamboozled by an ad” — all caps — because you didn’t realize it was an ad until you were basically 35 seconds in.
Shaan: And even then, it’s not some polished demo. It’s a phone recording a laptop of someone typing “Jenny AI” into Google search. Then finally it tells you what the product does: “write 2x faster.” And the happy ending is she submits it on time.
Sam: Okay, four million views. Is this how my doctor and lawyer and accountant are — sitting at Starbucks at 11:50 trying to plagiarize a paper due at midnight?
Shaan: Well, that was eight years ago. You went to college with people who are now doctors. You’re like, “I know that guy. That guy only drinks Jägermeister. This guy should not be a doctor.”
Jenny AI’s Results and Shaan’s Take on It as an Investment [00:22:45]
Shaan: So right now these guys are at $300,000 to $350,000 a month — $3.6 million a year — and doing really well. Congrats to the Jenny guys.
Shaan: Oh — and by the way, he gets cancer. He says this in the Starter Story video. He goes, “I felt like my dreams and my nightmares both came true at the same time.” He got cancer during that stretch, last year or whatever, had surgery, got out, and he’s good now. Crazy story. Congrats to him.
Sam: I don’t think I’d say this is going to be a smart investment. I think it’s going to be great for them — they make $6 to $8 million bucks, maybe, before 30. That’s amazing, you’re set. But this is a company I would love to own. This is not a company I would love to invest in. It’s going to make him very very rich at a very young age and make him mildly famous in our little startup community.
Shaan: If I was David, I would love to sell this thing for anything above a million dollars. AI moves too fast. I’m not trying to be in the middle of the hurricane of AI and hope I’m not made obsolete by one-click ChatGPT or some big company adding this feature. I think it’s actually fairly protected — it’s Niche enough that I don’t think too many people are going to go for it — but I just wouldn’t want to mess with it. Also, the college student essay-writing TAM isn’t the biggest either.
Sam: And also Sam Altman raised the equivalent of America’s GDP — like $5 trillion for whatever — whenever I see those numbers I’m like, that means nothing to me. If you told me the OpenAI headquarters is underwater, would you believe that?
Shaan: I would believe anything about Sam Altman at this point. Yeah, should we scuba up and go visit him or what?
Hostage Tape: Sam Was Wrong [00:25:30]
Sam: All right. I’ve got a big one and a short one. I’m gonna give you the short one first. And I want to say upfront — last time I gave an update on this guy, he took that update, clipped our YouTube video, and turned it into an ad. And I got super pissed. So I just want to say: do not turn this into an ad. You do not have permission. It looked like I endorsed this product — I don’t.
Sam: A few years ago — I think it was three years ago — this guy started DMing me, telling me he has this idea for Hostage Tape. Do you remember I told you about this? It’s basically tape that you put over your mouth because mouth breathing at night makes you a bad sleeper. There are some health benefits, I guess. He got in right when the Hubermans and the Brian Johnsons of the world were taking off, so he timed it perfectly.
Sam: He told me he was launching this and I was like, “This is really dumb. This is the stupidest thing I’ve seen in a long time.” And he kept DMing me, kept sending me updates. I think in year one he did $2 million in revenue. He just told me he ended 2023 with $14 million in revenue. And now he’s saying that in 2024 he thinks he can get $40 million. He’s like, “We’re buying ads on Joe Rogan, we’re going to be sponsoring the UFC.” All this crazy stuff.
Shaan: Has this guy been sending you updates?
Sam: Not really — I’ve talked to him a couple times. But I’m going to file this under “I cannot believe this worked.” I still can’t believe it’s worked. He’s totally proven me wrong.
Shaan: May 25th, 2023, subject line: “He said it was a bad business idea…” — emailed out to his whole list. He’s like, “Hey folks, Alex here. Telling people you run a mouth-taping business isn’t all sunshine and rainbows. I recently got called out on a very popular business podcast called My First Million. I reached out to one of the hosts, Sam, to tell him my idea. He said it was a bad idea” — bold. “That was over a year ago. 1,400 reviews, hundreds of success stories later, I couldn’t help but message him again.”
Sam: So then he says, “I thought it’d be really funny if the Hostage Tape Army” — and none of these words should be in the same sentence, by the way. The Hostage Tape Army. “If you’re a customer, show up in the comments and say, ‘Hey Sam, hashtag shut your mouth.’”
Shaan: I like that part. “Hostage Tape, shut your mouth” — that’s good.
Sam: He goes, “I don’t want to start a war, but these guys appreciate a good prank.” We do, we really do.
Shaan: I don’t see one hashtag shut-your-mouth Sam in the comments, though. The cavalry did not appear for this one.
Sam: It’s funny that he’s doing this, and great that he’s winning. I still think it’s stupid, but God bless him. I got so angry when I saw my face on those ads. I started getting these ads and it said something like “I” — and I was like, “What the —” He totally jiu-jitsued me. Now I’m promoting him.
Shaan: You shared an L. How do you feel about that?
Flo App: The Investment Shaan Should Have Made [00:29:30]
Sam: Tell me about an L you took.
Shaan: It’s 2020. I’m getting dinner with a friend. We’re only like 40 minutes into the dinner and he’s like, “I got to go.” And I’m like, was it me? Something I said? What’s going on? Why do you have to leave? He’s like, “No, no, no — I hate to leave, but I gotta go meet with this founder.” It was just the two of us at dinner and he just bounces. He says the company’s from Belarus. And I’m like, all right — I don’t know if that’s an elaborate excuse or what.
Shaan: I finish up dinner, go home, and I see an email from my friend. He says, “Sorry I had to jet so early, but this company’s really interesting.” He tells me about this company called Flo and he’s like, “If you want in, I can get you in.”
Shaan: I remember this because yesterday I’m scrolling on Twitter and I see Flo is one of the biggest success stories in consumer startups today — $192 million in ARR with 60 million active users. It’s been the fastest-growing health app for like four years. And I’m like, $192 million ARR — why does this app sound familiar? I go back and look at my email, and I see that I could have invested in this thing years ago, had I just replied to that email from my friend.
Sam: What valuation was it back then?
Shaan: I don’t know, because I didn’t even reply to ask. But whatever it was, I should have done it. The thing has been growing so fast that it’s clearly become a billion-dollar company and it’s done really, really well.
Sam: Last pod you talked about — I forgot what it was — some Eastern European app builder factory? Yeah, they make a variety of apps — one is muscle building for men, another is working out for women while they’re on their period.
Shaan: Well, I see your Eastern European women’s period app and I raise you — because that’s what Flo is.
The Flo Founders: Twin Brothers from Belarus [00:32:00]
Shaan: Flo was started by these guys out of Belarus or Lithuania — two twin brothers. They’re raised by a single mother who’s a librarian. He’s like, “Yo, we’ve got to make money.” They’re fifteen years old. He’s like, “I would go to school for eight hours, then go work a full-time job after school for eight hours. That’s what I did every day as a teenager.” And he’s like, “I just said, we have to figure something out.”
Shaan: So he did two things. He taught himself to code — using textbooks. And then he started actually writing books to make some money. He’s like, “Whatever I learned, I would package up into a book and write it. I’ve written a bunch of books. Then I became a book publisher — I’ve published like a thousand books now.”
Sam: Okay, random.
Shaan: The other thing that happened: 2008, the iPhone App Store comes out. He’s like, “I think this is going to be big — like the internet was big, there were a bunch of winners, I think there’ll be some here.” So he says, forget the book publishing, let’s start making apps.
Shaan: They start a health app — kind of fails. Start a second app — kind of fails. People ask him: was Flo your first app? He’s like, “No, no — I started two things before that, similar space, but it just didn’t fully hit. But I believe that success is the sum of your attempts. Those first two attempts — that is the success of Flo.” And I just love that quote: success is the sum of your attempts.
Shaan: So he starts Flo. And they’re like — so you’re a dude building a women’s period tracking app, the number one period tracking app in the world. How does that happen? How does a dude in Belarus do that?
Shaan: He goes, “It’s not my job to build the product. It’s my job to build the company of people that are able to build the product.” That’s exactly it. I love that. As a job, as a CEO, as a founder, your job is not to build the product — it’s to build the company that will build these products.
Flo’s Growth and the Holdco Strategy [00:35:15]
Shaan: They actually built a holdco, and the holdco owns four apps that are all super successful. They own Flo, which itself does about $200 million a year in revenue. It started as just a simple period tracker — a monthly kind of calendar tracker — but then they build off of that. They created what they call a women’s health super app.
Shaan: This was the pitch I saw at the time when my friend went and got dinner with them. They were like: “We built the number one period tracking app, and at the time we had 30 million users. In the US, 10% of adult women were using our tracker.” So they built the best tracker. But a tracker alone isn’t going to be the most monetizable thing. Why do people track? They track because of health reasons, because they’re trying to get pregnant, because they’re entering menopause — there’s all these other things. Maybe they need health coaching. Maybe they need these other things.
Shaan: And they turned out to be right. They’re making more money than any of these other health apps. This is a bigger app than Calm or any of the meditation apps in that health-and-wellness space. It’s run by these guys in Eastern Europe who’ve basically dominated the world in one category.
Shaan: They also own a couple of other companies — another app called Zing, and another app called Prisma, which is a photo editor. Do you remember when Prisma went viral a little while back with cool-looking filters?
Sam: Yeah.
Shaan: The holdco has raised a hundred million in a Series B, and it’s called Palta. They’re based in Lithuania. They have hundreds of employees.
Shaan: The pitch deck was basically like: “We can hire 10 super-talented European coders for the cost of one mediocre engineer in San Francisco.” They didn’t say it like that — I added the mediocre part — but the implication is: we have this talent advantage. We’re the big fish in the small pond, but the small pond is highly talented, with really good programmers, and we’re super cost-efficient.
Sam: You could have invested in this.
Shaan: Yeah. That one sucks.
Shaan: The first one — Jenny — I don’t think even now that would’ve been a great investment. Great business to own, not a great business to invest in. But Flo would have been a great business to invest in. It just didn’t hit any of my patterns. Eastern European company vs. Silicon Valley company, it’s in period tracking — I didn’t know how big that space could be. I underestimated it. I think a lot of people underestimated it.
Why These Founders Didn’t Fake Their Origin Story [00:39:00]
Shaan: What I love about these guys is they didn’t do the thing that all Silicon Valley startups do — making up their origin story. Like, Jack Dorsey with Square: “I was trying to buy a vase from a guy who was blowing glass, and he couldn’t take a credit card. I thought, wow, the small businesses of America are really underserved.” I think part of that story is actually true, but most startups invent their origin story.
Sam: Like Native Deodorant: “My sister was pregnant, I just didn’t want her to have aluminum in her armpits, so I created a pregnancy-safe formula.” Right, dude. The shipping cost of deodorant is just way cheaper than mattresses. That’s why you did it.
Shaan: Or like, “I went to Etsy and hunted for the most highly-sold product that didn’t have competition, was under one pound to ship, and had 80% gross margins.” Not as good of a PR story.
Shaan: But these guys — they didn’t do that. They were like, “Why did you do this?” He’s like: “We just wanted to find the most underserved market. We knew that no talented builders were building in this space, and we thought — half the world’s population has this problem, they’re completely underserved, and we can build a simple product that might have legs to grow from there.” And that’s what they did.
Sam: This guy’s amazing. We’ve got to get him on the pod.
Shaan: His name is Yuri Gurski — I’m probably pronouncing that a little bit incorrectly. He’s from Belarus, but I think they kind of live in Poland, Cyprus — they’re all over the place. He’s really successful. He’s had multiple companies he sold — one to Facebook, one to Mail.ru, one to Google. These guys are hardcore. These guys are awesome.
Sam: Yeah, these guys are ballers.
Market Selection: The Peter Thiel Venn Diagram [00:42:00]
Shaan: He basically said this — and I love that he said it: “Most people, you need three things: the right target market, the right timing, and the right people to execute. Most people don’t get the first two right. But that’s your rising tide.” If you can pick the right market and the right timing, he’s like: “We picked this underserved women’s health market and we started in 2008, right when the apps came out. We were early, we went to the underserved market with demand. From there, all we had to do was hire good people and it would work out.”
Shaan: Most entrepreneurs, if you made a pie chart of where their brain is — number one is how cool is my idea, basically the product. Then they focus on the people. And last is the market — they kind of think about what market they’re in and try to brute force the best product into whatever market, even a meh market. But you’d rather go into an amazing market and build a “good enough” product.
Shaan: The best example of that: Coinbase. Their website early on sucked — it went down all the time. But they picked a market where people were begging for it and willing to put up with a crappy product.
Sam: Michael Acton Smith from Calm gave me this great sound bite one time. He was like, “I launched these other things and I kind of had to push the rock up the hill to make it work. But with Calm, it was as if I had just been surfing and I caught this massive tidal wave. My job was not to push the rock — it was just to hang on and hope I don’t crash, because it was doing all the work.” That’s the difference between something really working and something not working. He’d built all these amazing things as a really good entrepreneur, kind of brute-forced them into reality — but when you pick the right market and catch the right tidal wave, life is a thousand times easier.
Shaan: And the hard part is — what people get wrong is: okay, I want to pick the right market, so they go to the biggest, flashiest market. Right now: AI. Gotta go into AI. It is a hot market — there are going to be huge winners there. But the trick is, Peter Thiel once went to a meetup and they asked what the key to investing was. He drew two circles like a Venn diagram. One: “seems like a bad idea.” The other: “is a good idea.” He’s like — the problem is most people just do things that sound like a good idea. The problem is everybody else is also doing things that sound like a good idea. So you’re all competing in the same space, and you might be too late by the time it seems like a good idea.
Shaan: The secret is: can you find something that today seems like a bad idea but is actually a good idea? Coinbase started back when Bitcoin wasn’t considered an obvious play. Crypto wasn’t the wave — it was an underserved market that wasn’t already seen as the trendy thing to do. That’s what AI is today — everybody agrees it’s an incredible market, so they’re all going to go fight this battle over there. You really have to niche down and find some section that’s underserved, or go somewhere that’s not yet seen as the thing. Find the thing three years from now that is AI.
Sam: This sounds like the Hostage Tape guy giving his TED Talk. He’s going to be standing there like this, talking about the Venn diagram of bad ideas and good ideas, and his idea is going to be right in the middle of the bad-ideas circle.
Shaan: Yeah, you’ve got to be in the middle. I’m sorry, Hostage Tape guy — you’re right, I’m wrong. You’re the one winning.
Sam: These guys are amazing. I would love to get this guy on the podcast. He’s definitely an English speaker, right?
Shaan: He probably speaks better English than us. Is there anything this guy can’t do? If one guy had to save my life, they were like “how about this guy” — I’d be like, yeah, sure. And if you Google Yuri Gurski, he’s got the perfect balance — that next-door look, you know? Like you could chill with him, but he also looks like he could really mess you up physically.
Sam: I get so many messages of people making fun of me — they either think I’m gay or they’re like, “Dude, why are you always commenting on people’s cheekbones?” And I’m totally just giving into it.
Super Bowl Riff: Jason Kelce vs. Travis Kelce [00:48:30]
Sam: Did you watch the Super Bowl?
Shaan: Yeah. I’m not a sports guy, but I watched it because it was a big deal. Jason Kelce, Travis Kelce — Travis seemed pretty likable in his post-game interview. He seemed like a big goofy idiot in the best possible way.
Sam: Kind of, although during the game he basically got super angry at his coach and almost knocked him over. The reason it wasn’t cool is because his coach is old enough that you’re like — that’s like pushing an old guy. He kind of lost his balance for a second. Everyone felt bad for their own dad in that moment. But they hugged it out, they seemed fine.
Shaan: All the Taylor Swift fans had an emergency meeting. “I’m worried about Taylor. I don’t like what I saw out there.”
Sam: But did you see the brother? Jason Kelce dressed up like Zach Galifianakis from The Hangover — like Alan from The Hangover. He looked hilarious.
Shaan: I basically want to do a TED Talk — prepare slides — called “Here’s why you should be Jason Kelce and not Travis Kelce.” On paper you want to be Travis: he’s the tight end, he’s better-looking, more stylish, can dance, dating Taylor Swift. Jason is a center — the most unglamorous position there is. The other guy’s kind of awkward.
Shaan: But Jason Kelce’s wife is a badass. Great-looking, former athlete, super fun, joins this podcast all the time, great personality, seems super down-to-earth. She shows up to the box — they know they’re gonna cut to Taylor Swift like a hundred times during the game, and Taylor’s there with Blake Lively, both of them doing YouTube-thumbnail face, super exaggerated emotions because they know they’re performing — whereas Jason Kelce’s wife is in the background wearing like her college hoodie, no makeup, just super comfortable, having a great time, eating food, drinking, chilling out, not trying to get attention.
Sam: You’ve thought about this a lot.
Shaan: Last week — two weeks ago — they played in Buffalo and it was a crazy snow game, playoff football. Jason Kelce was watching his brother play and he decided: I don’t want to sit in the luxury suite. He takes his shirt off, jumps out of the luxury box into the crowd with the Buffalo fans, starts chugging beers, just having a great time. His wife was like, “Don’t do this, babe — Taylor Swift’s here, people are gonna see you.” He’s like, “I don’t care. This is what I grew up loving about football.” You could tell this guy is having a great time. He’s not in it for the show. He’s got the real relationship goals.
Shaan: And then he shows up to the Super Bowl dressed like Alan from The Hangover. I love Jason Kelce. Jason Kelce over Travis Kelce — that’s my case.
Sam: I just Googled “Jason Kelce shirtless” and you do see him in the box wearing gray sweatpants, taking his shirt off, in full drunk-guy mode where he’s yelling. What’s hilarious: you see his face and you see some of the things he says and he just sounds like a goofy dummy, like he’s your fat friend joking around. But then they show him shirtless and there’s a can of beer in his hand — and it is so small. This guy is a giant. The beer looks like a 5-Hour Energy in his hand. This guy is a freak.
Shaan: He doesn’t look huge when you just see him from the neck up on the podcast. And he’s got gray hair, so he doesn’t look like an athlete. But you see him shirtless — this guy looks like a freak.
Tracy Chapman and the Authenticity Mount Rushmore [00:54:30]
Shaan: And I think there’s some life lesson there. Also — did you see the Grammys and the Tracy Chapman thing that went super viral?
Sam: Yeah. Her and Luke Combs — “Fast Car.”
Shaan: She looked awesome. Do you know her story? Do you know the backstory?
Sam: She basically was a normal person. Got discovered by a friend of a friend — the writer of Billions, his dad worked in the music industry. Brian went up to Tracy — they went to the same college — and was like, “Look, this is going to sound lame and I never like to ask my dad for favors, that’s kind of douchey. But you’ve got it — would you care if I made an introduction? I actually think he might help you. I’m not just blowing smoke up your ass.”
Shaan: And it became something. She kind of gets a contract, but she’s the anti-artist. She’s not going to do what the record label wants. They were like, “Tell us about your relationship.” She’s like, “I prefer to keep that private.” They’re like, “But who is this song about?” She’s like, “Well, it is about someone, but I prefer not to share. I don’t want them to feel bad about it.” They’re like, “It’s hard to promote this album if you’re not gonna say anything.” She’s like, “I just want my music to speak for itself.”
Shaan: I went down a rabbit hole after this, watched some interviews, and she is the beacon of authenticity. Her and Jason Kelce are like — you actually want to be them. You don’t want to be the pop answer.
Shaan: There’s something to just being totally authentic and not performing for everybody. She makes all the little TikTok stuff look like… little TikTok stuff. You know that subreddit “I Am the Main Character”? It’s full of people who like think they’re the main character of life — they put a camera on a flight, they stand up and do a TikTok dance, and everyone else is like “dude, can I get to my seat?” These annoying people trying to do stuff for attention.
Shaan: Do you know how old Tracy Chapman is?
Sam: In her 50s? Maybe?
Shaan: She’s 60. She looks awesome. She’s got no makeup on, just went gray. They’re like, “How do you promote your music?” She’s like, “I don’t know — I don’t have social media.” You don’t have social media? “No, I just hang out with my friends. Why would I need that?” They’re like, “But because — um — because…” and you sound like an idiot trying to explain why she needs social media. She’s like, “I just make my music and I hang out with my friends.”
Shaan: They asked what she does on her phone. She’s like, “I don’t have a smartphone either.”
Sam: Haven’t you heard the story of the Mexican fisherman and the banker? A rich banker’s on vacation in Mexico and he meets this fisherman who brings him fresh fish every day. The banker goes, “Hey, why don’t you just hire more fishermen, grow this into a thing, we’ll build it up, make so much money.” The Mexican guy says, “All right, but then what?” The banker says, “Well, you’ll be rich and you can do anything you want.” The Mexican guy says, “What would I do?” The banker says, “Well, you just fish all day and hang out.” And the Mexican guy says, “I do that now.”
Shaan: The whole parable of your great life is a lot simpler at the end.
Sam: I’m not sure what it’s all about. Be the banker — let’s go on vacation. Be a fisherman your whole life, yeah.
Shaan: I think you missed the ending. I think it’s about knowing what you want and knowing when you have enough. There is such a thing as enough. Tracy Chapman has enough. Jason Kelce has enough.
Tracy Chapman’s Lucky Break: Nelson Mandela’s 70th Birthday [00:59:30]
Sam: A couple other cool things about her story that I really like. One — be prepared to take the chance when luck presents itself. Do you know how she got her big break? What catapulted her to become a star?
Shaan: How did she do it, if she’s not doing the normal stuff?
Sam: There was this giant televised music thing for Nelson Mandela’s 70th birthday. And she’s on the prelims — the undercard of the undercard — before the TV cameras even turn on. She plays two or three songs early in the day. Then later in the day, the headliner is supposed to be Stevie Wonder. But Stevie Wonder — they messed up his backing tracks. He’s like, “I can’t go on, this isn’t going to work.” So they’re like, the audio is messed up, we need somebody to fill like six minutes of time. Who can go on with no backing tracks and just play acoustic and kill it? And they were like, “Tracy — will you go on and play a song?” She’s like, “Okay.”
Sam: Just you and your guitar. She goes out there. You can see this video on YouTube — her voice is quaking at the beginning. No autotune, no vocals, no backing track, so you can hear every imperfection. But then she kind of comes into her own, sings the song, and people go nuts for it. That’s how she got her break — by being prepared, being willing to take a risk, and having the talent to back it up.
Shaan: Her first album sells 10 million copies. That’s insane.
Sam: Then the record executives come to her with ideas for the second album. They pull the curtain off the easel — big pitch meeting — and they’re like, “Tracy Chapman singing these pop songs.” She’s like, “No, I don’t think I want to do that.” They’re like, “But Tracy, you did 10 million your first time, you could do 20 this time.” Like the banker to the fisherman. She’s like, “No, I don’t really want to do that.” They’re like, “Well, what do you want to do?” She’s like, “I’m not sure yet. I’m going to experiment and figure it out.”
Sam: Normally what a musician does: they go write songs, go to a studio, hire a session musician to come play with them — no chemistry — record, then go on tour and perform. She did it in reverse. She’s like: what if I hired a set of musicians that I really like, took the risk of hiring them, and what if we tour for a year writing songs as we go? Through the tour, we’ll see what’s resonating with people, and at the end we’ll record the stuff they liked. Almost like a comedian going to small clubs and working out their material — she did that for music.
Shaan: And I’m on an authenticity kick right now. I love that approach. To me, her and Jason Kelce — they’re on the authenticity Mount Rushmore.
Shaan Schools Sam on Music and Culture [01:03:30]
Sam: You know, last year I said, “Shaan, I’m going to have a baby — tell me what are some of the highlights of having a kid.” This was in private. And you said, “It’s just great. My son and my daughter — I get so much joy out of seeing that they admire all these little things. They love staring at the fan, and it made me happier that the fan is actually cool. I’m interested now because they’re interested. I love seeing them grow.”
Sam: That’s how I feel right now. A few years ago I asked you about really simple things — like Dolly — and you were like, “Dolly who?” Now you’re teaching me about Tracy Chapman. Next you’re going to tell me who the Beatles are and give me this wonderful breakdown. You have grown so much. You are now like Tracy Chapman. I didn’t know everything about her, but I can tell you a lot of her songs, and now you’ve just discovered her and you’re bringing a fresh perspective. You’re actually teaching me about an artist that I love.
Shaan: Next we’ll talk about Paul McCartney, Eric Clapton. Tell me who Mick Jagger is.
Sam: I used to stop believing, but now I realize I shouldn’t stop believing.
Shaan: That’s a great song.
Sam: I am getting so much joy. I’m learning, now that you are new. You probably didn’t know much about her before this, did you?
Shaan: No. I mean, I just heard the song. I loved the song but I didn’t actually know — are you so… there are two types of people: people who listen to songs for the words, and people who listen to songs for the music. Which one are you? Because I could hear a song a thousand times and not tell you what it’s about. I don’t even think about it. I might know some of the words but I couldn’t tell you the meaning.
Sam: I care about the meaning. Like, particularly rock and roll by a lot of Black artists in the 70s and 80s — it’s civil rights stuff. I enjoy learning the story behind it. But I actually don’t know what “Fast Car” is about.
Shaan: You should go listen. Actually listen to the lyrics. It’s an amazing story that she’s telling in that song.
Poise as a Trait Nobody Talks About [01:06:15]
Shaan: Also — I think both of us appreciate poise as a trait. It’s something nobody ever talks about, but we all notice it when we see it. Nobody says “I’m practicing poise.” But when we see it, we all think it’s badass. “Tom Brady is so poised.” “That leader just carries himself so well.” It’s poise — under pressure.
Shaan: She did this Charlie Rose interview. Charlie Rose — she’s kind of the worst interview ever because she doesn’t say anything, she doesn’t play the game. He’s like, “Tell me, when you were a young kid, when did you first start playing music?” She’s like, “Oh, you know, I got a guitar and I started playing when I was about five. By eight I was writing songs.” He’s like, “And that’s when you knew you wanted to be a musician?” She goes — she didn’t say “I think” — she goes: “That’s when I knew I was a musician.”
Shaan: And I was like — what a statement. She wasn’t trying to say it for impact. What a poised way of saying something: “I realized I was a musician. That’s part of me. That’s how I am.” It wasn’t “I’m gonna try.” Trying is the least poised thing you can do. I am a musician. She’s a badass. I really respect her.
Shaan: And I think she lives in Ohio, which is — you know, like Dave Chappelle. These guys that are like — they could have it all, they could be in the middle and the thick of it all, but they’re in Ohio. Another one on the authenticity Mount Rushmore.
Sam: Right — walked away from $50 million because they were trying to control the show. And he’s like, “And then they called me crazy and said I was doing crack in Africa.” He’s like, “No, I’m not in Africa. What the hell are you talking about? I’m in Ohio. I’m not going to sell my image. I’m just gonna go live my life and be happy.”
Shaan: I actually, up until recently, thought he was in Africa — because that was the narrative. “Dave Chappelle went crazy, he’s doing crack, he went to Africa.” He came out years later like, “No — they were offering me a contract, I said no, and I just went home and did other things with my life.”
Sam: The poise thing — when Mandela got locked up for however many years, came out, did something great — he said something badass. They were like, “Aren’t you angry or resentful at the people who put you in jail for 20, 30 years?” And he was like, “No. I was preparing.” And I was like — that’s awesome. That’s a cool way of saying it.
Wrap-Up [01:09:30]
Shaan: Coming through big time. This is the Shaan Puri episode.
Sam: That was a good one. Am I cultured now?
Shaan: I think so. The second you get props to Tracy Chapman and Nelson Mandela, I think you’ve officially crossed the chasm, my friend. You know when you leave milk out for a while it becomes yogurt? That’s what happened to you. You just sat out for a while and it happened.
Sam: Took me a couple dozen years but I’ve crossed the threshold.
Shaan: Congratulations. Good job. Good pod.
Sam: If you’re a fan of this — you get to subscribe. If you want more Tracy Chapman stuff but also the occasional joke about Mexican fishermen that we totally skipped over and don’t understand the moral of — you’ve got to subscribe. That’s the pod. Thanks.