Sam and Shaan open with Sam’s NFL combine fitness challenge and a business idea for a traveling youth sports combine. They break down the New York Times’ fawning “Liz Holmes” rebrand piece on Elizabeth Holmes and compare her situation to Ross Ulbricht’s life sentence. Shaan then runs his Baller of the Week on Jesse Itzler — his Marquis Jets sale to Berkshire, Zico coconut water, David Goggins, Sara Blakely, and his new pickle venture. They close with Rakuten’s office cleaning ritual, the “way you do one thing” principle applied to Hampton, a breakdown of parallel vs. serial entrepreneurship, and Shaan’s regrets from Monkey Inferno.
Speakers: Sam Parr (host), Shaan Puri (host)
Cold Open [00:00:00]
Sam: There’s like dudes in prison for like two decades for selling a little bit of weed, and she’s just walking out of here. She basically took maternity leave from prison. Like, what’s happening? I don’t understand.
Intro — Sam’s Shirt and Weekend [00:00:15]
Shaan: All right, what up. We’re here. Sam, incredible shirt. I mean, enough said — not just one man to another, I’d like to issue a quick compliment and I’d like to move on. Someone in the comments said, “Oh wow, Sam’s dressed like a grown-up.”
Sam: All I was wearing was a coat. I’m sitting here on top of this shirt, so I had to bring it back down. I had to let people know — you know, I could play both sides here.
Shaan: Yeah. Austin 3:16, baby. “Still got that dog in you.” I think that’s going to be the next shirt we make — “still got that dog in him.”
Sam: Okay, where do you want to start? First of all, did you do anything crazy this weekend? Because I feel like your weekends are a lot more interesting than mine.
Shaan: This weekend I watched Cops on Sunday. Because that’s what I do. It’s a solid session of Cops. But then — so I did this combine thing. I set a new fitness goal every quarter, and this quarter I wanted to score average for a wide receiver in the NFL combine. If you Google “NFL combine averages” you can find them. And this Sunday I had to do my bench press test, which is 225 pounds — I had to do it about 15 times. I just about hit 15. So my results for my combine tests: I almost scored average. I just missed it a little bit, but mostly I was there.
Sam: Wow. Yeah.
Shaan: The big discrepancy is when they do the combine they use an electrical timer for the 40, and I did it by hand. My hand time was the same as the electric time, but typically electric is slower — meaning you have to add a little bit on the hand times. But I kind of did it. I kind of did it.
Business Idea: Traveling Youth Sports Combine [00:02:30]
Sam: This was one of my favorite business ideas that I’m not aware of anyone having done. It’s not my favorite in that I don’t think this is going to be the best business — I just wish this product existed. Which is a traveling combine for your town.
The way I was thinking about it was for youth sports. The market of 33-year-old guys who really want to test themselves before they leave their athletic prime — that’s you, and that’s a small market. But a big market is parents who really think their kid is a special snowflake. Why don’t they have a version of the combine where you get measured on height, weight, wingspan, speed, agility, strength, vertical leap, all that — for all kids who are in competitive sports? Because for travel soccer or travel baseball, parents spend thousands of dollars and uproot their whole life just to pursue the kid’s athletic dream, which is maybe actually the parent’s athletic dream.
Shaan: And just being able to say, “Yeah, he’s really good — he’s playing with kids two years older than him right now.” They love saying that.
Sam: Yeah, there’s 14-year-olds in that league. So I think that product is great because it’s basically the Tough Mudder for little kids. You’d be able to charge, I don’t know, $150 per kid to get tested, plus another $20 a year to keep it all on file, another $20 to get the photo or the video montage that you’re going to post to social media. And then every year you come back and get retested — are you getting better or worse? What are your gains? I think this could be a viable business, and I would love if this existed. I’d love to get my kids tested, my niece tested — even myself.
Shaan: I’m taking this a step further. First of all, I knew I was going to marry my wife because when I met her father, he had ideal calves — you know, the ball in the calf.
Sam: Well — I think I got a bulk calf.
Shaan: Usually people who are explosive have like a little tennis ball in their calf. I saw his skinny ankle with the ball in the calf and I was like, all right. Skinny ankle has to go with it — that’s a thing, right?
Sam: Oh yeah, pretty sure. Skinny ankles. You need a skinny ankle.
Shaan: I remember I dated a girl and she did not have a skinny ankle and I was like, I don’t know if I can do this.
Sam: It’s not you, it’s me judging you. That’s a great way to put it.
Shaan: And then I remember Malcolm Gladwell had a book — he says if you’re born the eldest in your class, you’re more likely to succeed. You’ve got to be born in September so you miss the August cutoff, you get a full year to go dominate. So I was thinking about family planning — where are we going to live, what’s the school year cutoff, can we fit it in right before that?
And then this weekend I got out a piece of paper and basically mapped out my life plan. I don’t want to buy a home until it’s the home I want to live in forever, because moving sucks. The house I bought now was like “good enough,” and now I’m like — I don’t want good enough, I want perfect. So I’m plotting.
And I realize the right home has to have a five-to-ten-thousand-square-foot warehouse. Whatever sport they’re in, we’re going to build it. Hockey, gymnastics, doesn’t matter — we’re building that. They’re going to get awesome at it.
Sam: There’s not a lot of houses with a five-to-ten-thousand-square-foot warehouse attached. Just going to let you know.
Shaan: I’m building it. I’ve already looked it up. I’m building this thing. Also, I have a theory that because my wife and I are from very different ethnic backgrounds — don’t get canceled — I think if you mix all these genes into one child, they’re going to be a super baby. Won’t get sick, will have strong calves. We’ll see.
Sam: What’s funny is when you say it like that it’s strange but acceptable. If you’d said the opposite — “we have the same background, we’re pure” — all of a sudden you stepped out of bounds.
Shaan: No, I want a diverse kid. They’re going to be a super baby. My wife is mixed race and she doesn’t get sick. There are all these things about her that I notice — like whenever she takes medication, she never has the side effects. She’s a super baby. So we’ll see what’s going to happen. I will keep everyone updated — we’re waiting eagerly.
Elizabeth Holmes’ “Liz Holmes” Rebrand [00:09:00]
Sam: I’ve got a few interesting topics. You want to talk about this Elizabeth Holmes thing first?
Shaan: Really really quickly — so funny. Explain what you saw. I don’t have a New York Times subscription, by the way. I only saw the headline and the photo. Can you tell me what was in the story?
Sam: I will. So basically, yesterday — today’s Monday — Elizabeth Holmes from Theranos, you know, fraudster — the story is: she was convicted of defrauding investors upwards of hundreds of millions of dollars, got sentenced to 12 years in prison. She pulled a wild move where she had a baby. Baby one is two or three years old, baby two is now like six months old. And she’s making her plea to the government saying, “Actually, I have a newborn, you can’t put me in prison.” And they bought it. They delayed her prison sentence.
The New York Times did a big exposé on her — or like, positive feature? It seemed like a positive feature.
Shaan: Does “exposé” mean negative? Because this was not negative — this was incredibly positive.
Sam: Yeah, “exposed” — it’s like a guy with an accent saying “exposed.” They exposed her as being a wonderful human, is what they did. Because they make her sound heavenly. The headline: “Liz Holmes wants you to forget about Elizabeth.” The whole story is about how Elizabeth was this persona, and her new persona is Liz. She’s a normal mom. She speaks like a normal woman. Elizabeth Holmes was known for talking like this [deep voice impression] and wearing a black turtleneck. And she admits: “I did that because I was a woman and I’m blonde and I wanted to be taken seriously.” But now she’s got long hair, wearing blue jeans, she looks like a mom. She looks like me, honestly.
Shaan: She looks just like you.
Sam: It says: “Liz Holmes wants you to forget about Elizabeth. The black turtlenecks are gone, so is the deep voice. She wants you to meet her new persona — a mom.” And this is embarrassing for the New York Times to do this.
Shaan: People get mad at us for bringing people on the podcast to do interviews with — no, no, no. The New York Times posting this photo and doing this rebrand from Elizabeth Holmes to Liz Holmes? Liz Holmes, are you kidding me? A new persona. This is absurd.
Sam: Listen to this story. So here’s an excerpt — so Mr. Evans is her husband, I think. “In the waning days of Theranos, Miss Holmes got a dog, a Siberian Husky named Balto. Last year, when a mountain lion carried Balto away from the front porch, Miss Holmes spent 16 hours searching the woods, digging through the brambles and poison oak, hoping to find him alive. Everyone knew that he was dead, but Miss Holmes kept searching. She was relentless. The certainty, the fanaticism — it’s the same way Miss Holmes kept hanging on throughout Theranos. Miss Holmes eventually found her beloved husky Balto in the woods, but by then the dog had been torn apart by a mountain lion.”
And it’s this whole story about how her searching for her dog is a metaphor for her getting carried up in fanaticism. She was well-intentioned but just got caught up in it. Pretty wild.
And I have to remind people — I wrote an article, I actually posted it on here. I wrote it in 2016, read it in 2015. The headline was “The coverage of Theranos is utter —” and the first sentence is: “Elizabeth Holmes has been thrust into the spotlight as a scapegoat for all things wrong with Silicon Valley, but I find the media coverage around the Theranos drama to be utter —” and I explained why I think she wasn’t doing anything wrong and how she’s being hated on. I left the article up because you can’t take down a mistake, you’ve got to leave it up.
But I fell for this. And when I read this New York Times article, I realized I just fall for all this stuff. I read it and I’m like, oh, you’re right — she’s just like you and me. Let’s not send her to prison. I fall for all this stuff.
Shaan: Look at this picture. She and this guy and their two babies sitting on a bunch of rocks by the beach, barefoot. Why does this look so fake? First of all, it looks like you’re using Midjourney. And secondly, you can’t just get a new haircut and drop half your name. If I got a buzz cut and came on here and said “I’m Shop” — you can’t be like, “Oh, Shaw’s a great dude. He doesn’t care about money. Shaw tweets controversial things. He’s a different kind now — he’s a dad.” And then I take my kid to a place with some rocks, take a photo — that doesn’t work.
Sam: You know it is working, though. It is working.
Shaan: This is the greatest — do you know who James Todd Smith III is?
Sam: No, who’s that?
Shaan: LL Cool J, baby.
Sam: Oh my God.
Shaan: At least James Todd Smith had the decency to fully change it up and try to get a whole new persona. This is crazy that they’re just trying to make this happen. I don’t understand what’s going on.
Sam: It’s working, though. She’s not in jail. She was supposed to report to prison like three weeks ago. There’s like dudes in prison for two decades for selling a little bit of weed, and she’s just walking out of here. She basically took maternity leave from prison. What’s happening? I don’t understand.
Shaan: That’s exactly what happened. That’s exactly what happened.
Ross Ulbricht and Silk Road [00:17:30]
Shaan: And you know what’s another thing that’s kind of crazy — do you ever follow Ross Ulbricht on Twitter? Ross Ulbricht is the guy who ran Silk Road. Silk Road was like a drug marketplace, and in about three years it did like two billion dollars in sales. He’s also accused of doing murder for hire on three or four people — none of the people died, but the police took pictures of people pretending to be dead and sent them to Ross, and he hired the fake killer, which was the police. He hired them again and again. So anyway, he got life in prison, and he tweets about it.
I’m one of those guys who thinks he should go to prison, but dude — life is a long-ass time. For all of that. And he’s tweeting in prison, and I feel so sorry for these guys. I fall for all this stuff. I’m just soft.
Sam: Yeah, yeah, it sounds like it. So you think Ross deserves — isn’t a life sentence actually only like 22 years or something?
Shaan: No, he got life without parole. He’s in there forever. And he probably has multiple life sentences. It went all the way up to the Supreme Court. Basically the only way he’s ever getting out is if a president gives him clemency — that’s the word. That’s like the only way.
Sam: My nephew Ross — a telemarketer needs to call Biden, pretend to be someone from Indio, act like they work at Apple or the IRS.
Baller of the Week: Jesse Itzler [00:20:30]
Shaan: I have a few more topics.
Sam: What do you got that’s interesting?
Shaan: I have a feature here. I got a Baller of the Week for you.
[Theme music sting]
Shaan: A million dollars isn’t cool. You know what’s cool? A billion dollars. It’s been a little while since I had a good Baller of the Week. I kind of felt one bubbling up, and sure enough, I got one. I’m going to tell you some things about this person’s career and you can try to figure out who it is.
So — they’ve had a very successful business career. Sold a company to Berkshire Hathaway. A company that had done five billion dollars in a ten-year span of sales.
Sam: Wow. Impressive. I got one eyebrow up.
Shaan: They’ve won an Emmy. They were a manager of Run DMC, and 50 Cent was their intern at the time.
Sam: Music dominated, business dominated. What’s an Emmy?
Shaan: It’s actually TV. So this person wrote jingles for TV, that’s one way they made their bones. But they also managed Run DMC, which was the hottest rap group in the world at the time.
Sam: I think I know who you’re talking about.
Shaan: They also — you’re a fit guy, I see a cutter in those arms — this guy has run over 50 marathons, run a hundred miles in 24 hours, and had David Goggins live with him for 30 days and ended up writing a book about it.
Sam: Sounds pretty interesting. Is he a part owner of an NBA team?
Shaan: Yes. Does he have a successful wife?
Sam: That’s the best part. In his marriage, he’s not even the most successful one. Married who?
Shaan: Someone who I think is the youngest self-made female billionaire in the world. Incredible pull on his part. Also — the company that did five billion in sales wasn’t just any company. It was a private jet company. Fractional ownership of private jets.
Sam: Oh, there are a few of those.
Shaan: They were also a key partner in a CPG brand — everybody wants to start a CPG brand and see it on store shelves one day. Did that. Zico coconut water. Ever heard of that one? Sold to Coca-Cola.
Sam: Yeah, got it everywhere.
Shaan: They also wrote the official jingle for the New York Knicks. And in addition to that, sells online courses. He’s like one of us — just like us, these billionaires. Would you like to guess who I’m talking about?
Sam: Jesse Itzler.
Shaan: Jesse Itzler is the Baller of the Week. This guy’s got a fascinating career. I am — everybody’s got a different thing they admire, and the thing I admire most is people who play the game their way, on their own terms. And one of the ways you see that is people who have multiple chapters in their career where they’re able to turn the page and do something completely different.
From jingle writing to managing a famous rap squad to starting a private jet company to living in a monastery with monks to becoming an endurance athlete to becoming an NBA owner to doing coconut water — I love people who have done multiple chapters. I want to run you through his timeline.
Sam: Yeah, and I read the book. It’s called Living with SEAL. It was basically the book that got David Goggins famous. It was awesome.
Shaan: Was that before Goggins was super well known?
Sam: Yeah. In the book he doesn’t even mention David’s name, and then it came out who the person was. Jesse was at a marathon and he saw this guy — David Goggins, six-foot-six Black dude, ripped — and that’s not typically what an ultra-marathon runner looks like. He became friends with him and hired him.
Shaan: So here’s the timeline. Back in 1995 he started something called Alphabet City Sports Records — basically music, sports marketing, music production. They do it for three years, sell it for four million dollars. That’s how he got his first million.
Then he starts Marquis Jets. Marquis Jets was basically: how do you buy hours on a private jet without buying the private jet? How can you get more people access to private jets? You’d buy 25 hours of flight time on a private jet — like a debit card. Get to just go use it. Get a whole bunch of people doing that, and you might be able to use those jets a lot more efficiently than when just one person owns one that’s sitting on a runway 90% of the time.
Sam: Was that a big business?
Shaan: They never fully released any numbers. The one thing he said is they did $5 billion in sales in a ten-year period. And here’s what he said in an interview: “I’ll put it this way — we were extremely profitable. We did cumulative five billion in sales over ten years.” We’ll take that. And I also think when you sell to Berkshire Hathaway, they’re not in the habit of buying unprofitable businesses. They sold to NetJets, one of Berkshire’s companies.
Then Zico coconut water. These guys had been around for four years. He partners with them, says “let me invest, let me help you guys grow this thing” — it was pretty small at the time. And in the same year he invests, he gets Coca-Cola to invest $15 million, and eventually they sell the whole thing to Coke. In a four-to-five-year period, he helps Zico go from kind of unknown to pretty well known. Sold in 2013 to Coke.
He’s done similar things — invested in Kind Bars. He’s got this brand investor group called 100 Mile Group. They also invested in something called Sheets Energy Strips with LeBron and Serena Williams and a bunch of famous people — caffeine strip you put on your tongue, it melts, gives you energy. That one didn’t work out. Pitbull was also an angel investor.
He was part of the group that bought a piece of the Atlanta Hawks. He lives in Atlanta, I think — and also has a townhouse in New York. I follow him on Instagram, he’s always on an RV like a huge tour bus thing. Six kids too. The guy does it all.
Sam: Quadruple threat, dare I say.
Shaan: He also started this thing called 29029 Everesting. They rent a mountain, bring together food, music, and it’s an endurance event where you walk, run, climb, crawl — whatever you want — up this mountain, take the gondola back down, and keep going up and down until you’ve done 29,029 feet, which is the height of Everest. So it’s like hiking Everest without going to Everest, without the extreme risk of surviving Everest. He’s got an all-day running club — paid membership, $400 for the year. Wrote two books. And back in 1991 he was a rapper called Jesse James. Also wrote the New York Knicks theme song, “Go Go NY Go.”
I mean, just done it all. Really incredible variety in his career.
Sam: Prolific.
Shaan: Prolific. Good word. And his wife is Sara Blakely, who sold Spanx. I think it was just acquired for like two or three billion.
Sam: Do you know the final number? I think it was Blackstone that bought it.
Shaan: Yeah. And if I remember correctly, that company was entirely bootstrapped.
Sam: 1.2 billion. I think she owned most of it.
Shaan: So they’re killing it. Imagine being Jesse and not being the most successful one financially in the relationship.
Sam: What’s like the best thing about — I wanted to make a joke about like, he does the dishes at this point, or something like that.
Shaan: He manages the people who do the dishes at this point.
Sam: I’ve been following Jesse for a while. He kind of became the self-help guru and I was turned off by him, and then I actually started following him more and was like, “Oh no, you’re actually pretty awesome.” He’s been on the forefront of a lot of popular health trends. He was really into saunas for a long time, now hot and cold exposure is quite popular — he’s been doing it for years. He’s also been doing fasting. I would follow him like years ago and he would go five days without eating, trying all these weird health things, and now a lot of these things are popular. He was doing it for a while.
And in the book — Living with SEAL — he basically found David Goggins, Goggins lived with them for 30 days. It’s an awesome book. He tells all these crazy stories about this guy. I’m a big fan of Jesse.
Shaan: I had the same reaction — I saw him in a bunch of public speaking slash ads being like, “You gotta take my course,” and I was like, usually people who are that self-promotional, their main business is the selling, not the having-been-successful. That’s a general rule of thumb. So I was really surprised when I looked into it — this guy is pretty prolific, he’s pretty legit.
Sam: I think I just bucketed him mentally as online business guru guy. But once you see all the stuff he’s done, that’s a total mischaracterization.
Jesse Itzler’s Pickle Business [00:34:00]
Shaan: One more really interesting thing — have you heard about his pickles thing?
Sam: No, what’s that?
Shaan: He posted this on Instagram last month. He goes — all caps — “WHY I’M EXCITED ABOUT PICKLES.” He says: “Last week I said I wanted to buy or partner with a pickle company. Boxes of pickles have been showing up at my house all week. Exciting. I’m doing a live taste test this week. They’re all so different. Lots of people asking me why pickles. Here’s why.”
He goes: first, can you name five pickle companies?
Sam: I hate pickles. I don’t know. Can you name any pickle companies? There’s probably only two or three I can think of.
Shaan: Exactly. It’s a crowded market but not many dominant players. Second, pickles are underrated — Americans eat 20 billion pickles a year and there is no buzz in the category. Not much fun, not much creativity. All the packaging is the same. Third, the average American eats nine pounds of pickles per year. Fourth, the average American household buys a new jar every 53 days. Fifth — purely pickles are a big deal. Entrepreneurs look to make things better, and often those new ideas come in the form of products they use daily. They get excited when they see a new lane. I see a new lane here.
And so he created this pickle company called Hoya Yaya Pickles.
Sam: Is that like a Yiddish thing?
Shaan: I have no idea. Pickles are popular among Jewish people, he’s Jewish — so maybe it’s like a Yiddish name? I don’t know. Funny name. It says if you go to their bio they only have 2,000 followers, but he’s crowdsourcing their brand while they find the best pickle company to partner with: “DM if you have a clean ingredient pickle company.” And there’s a picture of Adam Sandler casually eating a jar of pickles.
He’s basically trying to do the coconut water thing again, for pickles this time. And I think he could probably pull it off.
Sam: Pickles are awesome. I’m a big pickle guy. I like Jesse. We should get him on — hey, Jesse, if this makes it to you, come on anytime.
Shaan: Remember when I went to HustleCon — your conference — and there was the guy who created Method soap, Ollie vitamins, Welly Band-Aids? Three hit consumer CPG goods. Eric Ryan, I think?
Sam: Yeah, yeah. He’s like a flamboyant-looking guy, wears bright glasses, hair combed exotically.
Shaan: Yeah, exactly. He looks like he was born inside of a Warby Parker. He was on stage and gave a great talk. They asked, “How do you come up with ideas? You did Band-Aids, vitamins, soap — how do you see the open space?” And he basically said the same thing Jesse just said. He goes, “I walk down the aisles of a grocery store and I just wait till I see a sea of sameness.” So a sea of sameness is a shelf where you see a ton of products with no differentiation. For soap, go look at the soap aisle — it was just green bottles of the same product in the same shape. So they came out with a different bottle, it was blue, had clean ingredients. That was Method.
Same thing with Band-Aids. The whole Band-Aid section was trying to be this nude color that was supposed to match your skin — but nobody’s skin is actually that color. So it’s just like you’re hiding something. He said, “We believe every cut is a badge of honor, a great story to tell — so we want to put a badge on that wound that stands out.”
And the vitamin aisle was just a bunch of labels that all said “Vitamin D3, B12, C” — he came in with Ollie and they have a different looking jar that says “better sleep” or “better hair and nails.” The benefit of the vitamin, not the vitamin itself. And I think if you go down the pickle aisle, it’s probably a sea of sameness. Jesse’s going to work well.
”The Way You Do One Thing” — Rakuten and Hampton [00:40:00]
Sam: All right, I have another interesting person. Have you ever heard the phrase “the way you do one thing is the way you do everything”?
Shaan: Hate that phrase.
Sam: Why do you hate it?
Shaan: Because I do a bunch of things terribly. Does that mean I’m going to do everything terribly? If it’s true, I’m in trouble.
Sam: I believe that phrase to be true, and I believe it because I’m a little bit like you — I like to free-ball it, I try to figure things out as I go. My lack of discipline and lack of process sometimes really hurts me. So I’ve been obsessed with this phrase for the past couple years. You’re late for this pod — you’re also late for your kids’ Home Depot class.
Shaan: That’s right.
Sam: The way you do that one thing is the way you do everything. That’s one of the reasons the military makes you make your bed in the morning. They say if you start making your bed in the morning, that means you’re going to eat breakfast the correct way, which means you’re going to run the right way, which inevitably means you’re going to fight the right way. I believe in that.
So I was looking for examples of it, and have you ever heard of this company called Rakuten? It’s basically like Amazon in Japan, started by this guy named Hiroshi Mikitani — goes by Mickey. Similar to Jeff Bezos in Japan, a hardcore titan of industry but lovable. Rakuten has 32,000 employees, $14 billion in revenue, huge thing.
I love reading about Japanese entrepreneurs because there’s something about their culture that fascinates me. He has a handbook he gives every employee. I got a hold of that handbook a few years ago and read it. One thing that stuck out: in Chapter Zero, the very first thing outlined is called “The Basic Principles.” And Chapter Zero is about the fact that at their offices, they don’t have any janitors. The reason why is that every Tuesday at four o’clock they have an hour of “clean time.” Every week at the same time, everyone at Rakuten — from the CEO to the lowest-level staff — cleans their workspace. They take out rags and spray bottles, clean off their surfaces, pick up trash, get on their hands and knees and polish the legs of the chairs. It’s part of the culture since the company began.
The purpose is to foster a sense of ownership. He says: “We do this activity to remind ourselves that everything the company does is relevant to each and every one of us, to keep a sense of direct involvement top of mind. It’s also an opportunity to reaffirm that the entire company is a team, by having everyone regardless of position work together on the same task.”
I read this when I was leading The Hustle and I tried to make that a thing.
Shaan: And it didn’t work.
Sam: No one got into it. No one got it.
Shaan: I’m so glad you said that last part, because I’ve done this so many times. I’ve just Michael Scott-ed it so many times. I’ll read something or hear some cool person did some cool thing and I’ll try it in the office and I just get these looks, and within four days the thing is gone. I’m like, I needed a different force of will, a leather jacket, something I was missing to make this happen.
Sam: And once I failed at that, I realized I need to do this stuff even more. So with Hampton, I’m trying to figure out what that thing is. And right now it’s our Zoom setups. I’ve got this document called “How to Look Good on Camera.” Because when people apply to Hampton, we interview everyone, and me or Joe or someone watches the interview to see if that person should be approved. I saw one of our guys, his name’s Alex Pattis, and his camera setup was horrible. I was like, “Dude, this looks like a ransom video filmed on a Nokia.” So we’re going to fix this. I created a guide on how to make your Zoom camera look good and gave everyone a budget to buy the proper lighting. That’s my one thing I’m trying to implement now — I won’t talk to you unless your Zoom camera looks great. You can make it look pretty good for like $500.
Shaan: First of all, this doc is hilarious, and the picture of the guy who looks like a ransom video guy is hilarious. But I think you’re close and I don’t think you quite got it. I hate to do that to you, as a friend, popping the bubble — but I think you got half of it right.
Your solution is great, but you picked the wrong area. This is too logical, too quantifiable. You said, “First impressions matter” — everybody agrees with that. “You’re doing sales essentially for the company, so you need to show up the right way.” You can almost calculate the ROI.
The beauty of polishing the chair legs at Rakuten — or making your bed in the morning, or waking up at 4:30 just to harden yourself, or taking a cold shower — is that it’s unnecessary. It’s got to be something you kind of don’t want to do, or seems unnecessary to do. That’s the point.
Sam: So what’s an example?
Shaan: It’s almost like you’ve got to do something that doesn’t make logical sense. Like at Hampton, make everybody —
Sam: I’ve got to figure out what that thing is. But I definitely want it. I want a stick.
Shaan: I love a good stick. I’m a big fan of sticks. They add a lot.
Sam: Right now my current stick is the Zoom camera. It’s gotta look great.
Shaan: What about — everybody has a small tattoo on their ankle of a date five years in the future, which is when Hampton will be worth a billion dollars?
Sam: You gotta go pledge, baby. You gotta go get that. But I love that stuff. And that’s another thing we’re thinking about with Hampton — what rituals do our members need to have to get them bought in? I’m trying to research fraternities and sororities.
Shaan: I love this — in the same way that Tony Robbins’ shtick is the firewalk. Walking on coals. Have you done it?
Sam: Yeah, I did it. Twice, at his events.
Shaan: Was it like a pretty sanitary thing? Like there’s no real risk?
Sam: Yeah, basically — they make you stand on something that’s wet before, so you get moisture on the bottom of your foot, and then you can walk across the coals. Unless you stood there and stayed, it won’t burn through that layer of water. It’s just science.
Shaan: It’s a great actor with a great set. I’m reading this book about JP Morgan — this guy in the Gilded Age, incredibly rich. He once was trying to settle an agreement with five different union heads of different steel companies. He goes, “Come out to my boat and we’re going to go for a boat ride and discuss this.” They get on the boat. He goes back to the pilot and the pilot goes off in a rowboat. He comes back and says, “We don’t have a captain. We’re stranded out here until we settle a deal. We are not leaving until the deal is done.” That’s the pizzazz. Every great actor needs a good set. He set up that set wonderfully.
I’m constantly looking for what our ritual is going to be. I studied a bunch of different kinds of communities — everything from actual cults, to European soccer clubs where the fans are just insane. I went to Duke and we used to live in a tent for three months in a line just to get into the big game. Everybody behaves a certain way. People who don’t even like basketball live in a tent for three months just because they get swept up in the rituals, the movement.
I’ve also talked to people about Burning Man — when you get to Burning Man, you wait in line in your car for hours to get to the entrance, and when you get there they give you a name, your burner name, and you roll around in the sand. That’s like your entrance thing.
Sam: Yeah, like Firefox Lion Boy.
Shaan: I did something at my last company kind of like that. After six months of working, I called a team meeting and gave a presentation about each person. I gave everyone a superpower. I was like, “This is Derek — Derek’s the mailman. He delivers every day of the week except Sundays. You give him something at 9 AM, he’ll have it to you by 5 PM every single day without fail. Except Sundays, you message Derek, he’s not going to get back to you.”
And it was mostly true — everyone’s thing was believably true. But it’s amazing that everybody started living up to it. Everybody started referring to him as “the mailman” and he would always deliver because he had to live up to it. Give people a reputation to live up to.
With someone else I was like, “He’s a melter — you can’t bring around him. He’s radioactive, he’ll just melt through your BS right away.” And I think some people were intimidated by him, they felt like he was criticizing them when he would say something. But then it reframed it: he’s not criticizing you, that’s just his superpower — he identifies and melts it down.
So I tried to do that for everybody. That was one of the few random management experiments that actually worked. People really liked that they had a name, and they started using it in the office — whereas most things were just me trying to make fetch happen and they were like, it’s not gonna happen.
Sam: I remember early in my career, the only job I ever had — this guy had a shtick. He would try to get everyone to slow clap before, like — yeah. And I remember thinking, “This is so stupid.” But then after a couple weeks I was like, “All right, yeah.” Now I’m a little bit older and I’m like, performing stuff — I thought I was too cool for it. And then you realize, no, humans are not logical. We need this emotional stuff. The difference between a highly motivated person using their emotions effectively and someone who’s not is massive. You look at different battles in history, who’s fired up the right way versus who’s not — it really has a massive difference.
Shaan: Leadership, if you want to be a leader: three things are true. First, you have a higher standard for yourself than anybody else has for you. Doesn’t matter what your job title is — if you hold yourself to a higher standard than your manager holds you to, you are a leader. That’s the first definition of a leader.
Second, somebody who understands what the emotional state is and what it needs to be, and can transfer it. Basically, anyone who can understand that morale is low and needs to be high — they can shift the mood, they can shift the energy. Or if everybody’s a little too comfortable, they create a sense of urgency. They understand the emotional state of the room and know how to shift it. That’s two.
And third, they see things how they actually are — not worse than they are, not better than they are. How they actually are. And then they paint a picture of how it’s going to be better than it currently is.
To me, those are the things.
Sam: Are you reading this off something?
Shaan: No, that’s just straight off the dome.
Sam: Wow. That’s a good little thing. Next tweet right there.
Shaan: If I wasn’t a retired Twitter artist, I would have tweeted that one.
Justin Mares on Startup Momentum [00:52:00]
Sam: I’ve got one other quick one for you.
Shaan: Yeah, I’ve been eager.
Sam: I want to read you something. You’re on that Justin Mares tip — we talked about him last pod. He’s a fantastic entrepreneur.
Shaan: You’ve clearly been reading his blog. You’ve been obsessing.
Sam: Actually, somebody sent this to me afterwards. I haven’t — I’ve only read this screenshot they sent. Somebody sent this to me and said, “I feel like every time you reference something you said you’re reading a book and you’re actually five pages in.”
Shaan: Yeah, you love at first sight. You know it’s awesome before you even read the thing.
Sam: All right. Here’s a quote from his blog:
“I give the same advice to friends who want to start a company. Startups are momentum plays. That’s the key thing — startups are momentum plays. You choose the idea you are most excited about, you put a date on the calendar for three to six months. At that date you’re allowed to reflect on your commitment level. Until then, you do not spend any time questioning it. Should I be chasing X instead? Should I be doing this over here? No — you put blinders on for a period of time. You allow yourself to dig into the problem space and spend your early time actually working on the thing versus intellectualizing whether this is the exact perfect right and obviously huge thing I should be working on.”
That’s what I’ve struggled with when working on something new. Startups are momentum plays and you have to put blinders on to actually do the thing versus constantly questioning it, paralysis by analysis.
Shaan: Yeah. I’ve told you about this — I have this thing called “worry time,” where I say: today of the week I can worry about these things, and once that hour is up, no more worry time. It’s only do time. I can go back and reflect and figure out my worries at a later date. Sometimes I’ll do it six months out. Like when I was searching for kind of where you are now — searching for which company to start — I said, “For the next six months, it’s plan mode. All I’m gonna do is read and consume. I’m not going to decide a thing. I’m just going to consume and read, and at the end of six months I’ll make a decision.”
I love setting clear dates where you can’t do anything. I also love momentum. When someone talks to me about starting a business, I say try to get a sale in the next 24 hours. What’s the smallest thing you could do to get a sale in 24 hours? Because the second you make one dollar, everything feels like it changes. It’s like if you had poor eyesight and now you have glasses on — that little bit of clarity gives you a boosted energy to get the second dollar, which makes getting to a hundred, then a thousand easier. And at a thousand, you can see to a million.
And you have this cool line: A-B-Z. You worry about step A and how to get to B, and you can think about Z occasionally — your big motivating factor — but don’t think about all the letters in between.
Sam: Yeah. This reminds me of something I’ve seen a bunch — I have a sensitivity toward it because I did this. A lot of people want to do a startup studio, an idea lab, parallel entrepreneurship — doing multiple things at once. I ran an idea lab for five or six years and I loved it. It was the most fun thing you could possibly do. I had a blank check and an awesome team and I could pursue not just one idea, many ideas at the same time. Meeting to meeting, all this variety of adventures and challenges, ups and downs. I felt like I got 20 years of experience in four.
But notice I said experience instead of success, because it was a lot of lessons learned and a lot of skill sharpening. It wasn’t a lot of winning.
Sam: If you had stuck to one idea, do you think that would have been better?
Shaan: One idea would have been far better. So let me give you the three options. There’s what I was doing — parallel entrepreneurship: take multiple ideas and pursue them in parallel. This is the easy trap once you already have a win under your belt. That’s why you’ve seen Mark Pincus with Zynga create an idea lab, Kevin Rose create an idea lab, the guy from Uber, the guy from whatever — there’s like ten of these examples. Successful founder wants to do startups but has too many interests, too many ideas, more ideas than time, so they create a lab that’s going to create multiple hits. And almost none of them have any hits whatsoever. Zero is the average and the median for these studios. It doesn’t work, for a bunch of reasons.
Then there’s serial entrepreneurship — the Jesse Itzler thing. I’m gonna do this for this period of time, then do a different thing for the next period. Or I’ll take this one thing and if it doesn’t work I’ll pivot it into something else. I give each chapter several years of effort, focus, full intensity on one thing. But I’m willing to switch what the one thing is. I’m not trying to run the same company for a decade.
And then there’s repeat entrepreneurship — the person who does the same thing. I created one D2C brand, I’m going to create another D2C brand. Or I ran one company and I’m just going to run it for 15, 20 years. Or I did a newsletter business, I’m going to do another newsletter business.
In terms of likelihood of success: repeat is number one, serial is number two, parallel is number three. In terms of fun: parallel is number one, serial is number two, repeat is number three. I’ve tried parallel, I’ve tried serial, I haven’t tried repeat. I think the correct decision for me is serial — it has enough fun and enough winning.
Shaan’s Monkey Inferno Regrets [01:01:00]
Sam: Which idea do you think you should have stuck with at Monkey Inferno?
Shaan: For the most part, the ideas we should have done: we tried to create hit social apps, because before that the main person who ran it and the main investor had built a social network called Bebo, and they’d competed with Facebook and Myspace back in the heyday. They sold it for $850 million. Facebook went on to be worth $850 billion. There was always this shoulda-woulda-coulda, and at the time people were pretty down on Facebook. It felt like there was going to be something new — and sure enough, Instagram, Snapchat, TikTok eventually. New things did come out. That part was right. But the wrong part was trying to re-chase that dream, because the chances of success were so low.
So we built messaging apps and social networking apps and it was really, really hard to get it to work. What we should have done was build either tools for startups or tools for developers. We knew the pain points of an early-stage startup, we had a bunch of developers — like 18 developers. We could have built products for people like us.
Sam: What was the total budget? Like three, four million?
Shaan: I think we burned about three to four million a year. But it wasn’t all from outside — we also revamped one of his early businesses, Birthday Alarm, which was making millions in profit before I got there. It had been declining year over year for five straight years. We kind of revamped it, got it back to slightly growing. That covered a portion of the burn.
Sam: Was there a developer tool idea you had but didn’t do, and someone else came and took it?
Shaan: Three ideas that I think would have worked, that we literally discussed:
First was user testing. I used a very early pro version of UserTesting.com and I was like, “This is a pain point for a startup — I can pay a hundred dollars and get four people to go try our app and talk through it. They find bugs, tell us if they liked it, tell us what’s confusing.” These videos were amazing. Saving me so much time versus standing over someone’s shoulder in the wild. Super useful service.
I told Michael: “Hey, I think we should build this for startups. We’re in Silicon Valley, we understand the startup game, we’d be good at getting early-stage companies to use this.” And UserTesting.com is now a multi-hundred-million-dollar-a-year business. Went public at one point, went back private. They took it all the way to IPO. And he was like, “Yeah, could do. Seems kind of boring.” And I was like — I was 24 years old, he was my hero, and I was like, “Yeah, yeah, you’re right.” I backed off immediately.
Second — same thing happened with crypto, in 2013. Our sysadmin, the guy running our whole server setup, was like, “Guys, I’m mining Bitcoin on this server,” and tells us why Bitcoin is going to be the next big thing. All our engineers were like, “Yeah, this makes sense.” Our CTO — who normally never had product ideas, he was a builder, not an ideator — came to me and said, “I’ve got an idea. Bitcoin is going to be a thing. There’s only one exchange. Coinbase is just getting started. I think we could build either an exchange or financial services for the crypto industry. They don’t have credit card payment, you can’t do any of these things you’re going to want to do for a human being to use crypto. We should start building financial services — start with an exchange, then maybe debit cards, on-ramp, off-ramp.”
He was so motivated. He built a prototype overnight. He started coordinating with his designer, shoved the product manager into a corner like, “I got this.” That’s a great sign for a startup — when engineers intuitively know what needs to be built.
And then our in-house lawyer called our investor and was like, “Hey, the guys are talking about Bitcoin. I Googled it. I think it’s for drugs. I don’t know if this is the right idea.” So he came in and said, “Look, I don’t mind losing three or four million dollars in a year — that’s okay. But I’m not going to jail. I’m not trying to do money in serious ways in this gray area. Bitcoin sounds sketchy.” And I kind of convinced him to buy some Bitcoin as a hedge, but he was like, “I don’t think we should be in the Bitcoin business — you need licenses, you’re basically talking about building a bank, it’s super gray area. I can lose the $3 million, I can’t lose my billion.”
Sam: The message I got blocked.
Shaan: I don’t mean to blame him — the mistakes were all on me. I’m just recalling two examples where we had good ideas that we didn’t do.
The third was we had built Blab into a business that was like a really good video chat product. Four million users. Basically if you’ve seen Clubhouse or Zoom — you had four people on screen talking, with a live audience where anyone could request to join and start talking. You could do call-in shows. It got pretty popular — Tony Robbins was using it, famous bands were using it, the UFC was using it. Martin Shkreli was using it.
Sam: Yeah, exactly.
Shaan: We got to four million users, but it was pretty clear to me it was too leaky. People weren’t going to use this every day. The people who did use it every day were there to make friends — so they weren’t going to bring friends, they were there to meet people. So you had this problem where your sticky users don’t grow you, and your growth users don’t stick. That’s why, by the way, when I wrote that thread calling out why Clubhouse was not going to work, back when Clubhouse was at its peak — the reason I knew was because we had built a very similar product and run into all those same issues.
Sam: You didn’t get rich, but at least you got popular on Twitter. So there’s that.
Shaan: What’s it like — I just dropped $400 at Chuck E. Cheese and I got a little slinky laser pointer. Yeah. You guys have your little Twitter thing. That’s nice.
Sam: The move there would have been to shift toward B2B. Citrix had WebEx for video calls and meetings, and it was horrible. We had built a way better tool for webinars or large company all-hands meetings. We had a 5x better product than them at the time. I think we could have made it successful. We even had the idea — “Should we do B2B?” And I was like, “That means doing sales. Do we want to do that? Are we a B2B company now?” And I said, “Nah, we’ll just try again to build the next big social app.” Giant mistake.
Shaan: Hey, you’re not flying private and you don’t have a vacation home in Tahoe, but at least you learned.
Sam: If you’re not winning, you’re learning.
Shaan: I hate when people say “winning or learning.” I’d rather win. I don’t want to learn. I’d rather be a dumb winner than a smart loser, all day of the week. That’s easy. I’d rather be winning on my plane, barely knowing how to read.
Sam: This is why I love this pod — you get stories like that. Those are good stories.
Shaan: I think we should wrap it up there. But tell me one thing — what does your shirt say?
Sam: Awesome Baby.
Shaan: All right! We gotta start getting back into that stuff. I’ve been out of the game. Anyway, good pod. That’s the episode.