Sam opens with the story of entrepreneur Mark Jenny, who as a teenager sold novelty dollar bills on eBay for $15 each and scaled to $10,000/day in sales. That story launches a broader discussion of mass customization business ideas — from celebrity-face dollar bills to Etsy jewelry to pet-face socks — before the conversation shifts to Shaan’s list of unpopular truths he’s learned from the podcast (overnight success is real, where you live matters, luck is real, college prestige, skills vs. generalism, assume people don’t change, take risks before you have a family). The episode closes with Sam’s gifting business idea — a 1-800-Flowers competitor built on DoorDash as a cloud kitchen — and a deep dive into the gifting industry including Harry & David, 1-800-Flowers, and Omaha Steaks.
Speakers: Sam Parr (host, co-founder of The Hustle), Shaan Puri (host, founder of Milk Road)
Cold Open: The Dollar Bill Story [00:00:00]
Sam: Here’s the headline — great headline: “Guy sells one-dollar bills for fifteen dollars. Here’s how.”
So here’s what he did. He’s 15 years old and he sees a dollar bill on eBay. Instead of George Washington on it, it’s Michael Jordan’s face in the middle. He orders it because he’s like, “I love Michael Jordan, this is funny.” And he gets it — it’s basically a normal dollar bill but with a sticker paper over the George Washington. You could just do that. You could just go to Office Max and do this.
So that’s exactly what he did. He goes to Office Max, he’s like, “I need to be able to create these — because what better business is there than selling dollar bills for $15?” So he goes there, and then he puts them up on eBay.
Introducing Mark Jenny and His Luxury Airbnb Empire [00:01:10]
Shaan: What’s up. Let’s jump in — what you got?
Sam: You tell me. I think I’ve been driving the last handful of sessions. I’m gonna ask you to drive right now.
Shaan: Let’s switch gears. I want to do a topic about — do you know Mark Jenny?
Sam: Mark Jenny’s a great friend of mine. He’s an amazing entrepreneur, awesome guy. I’m going to meet him next week — we’re going down to stay at one of his places. He has this luxury Airbnb portfolio. You should follow him on Twitter. Do you want to give his background? Do you know his background?
Shaan: I know a little bit of it, but go ahead — give the story.
Sam: So if I remember correctly, he was raised in a tough situation — single household, something was a little wonky with his childhood. He wasn’t raised in a very privileged place. At one point I think he was even homeless, living out of a storage unit or something.
He started a bunch of different companies — info marketing stuff — and things did kind of okay. Then he started RV Share, which was like Airbnb for RVs. He eventually sold a large portion of it to KKR, a large PE company, and he probably made many tens of millions of dollars — a lifetime of money.
Now he has a new thing he’s been doing for the last maybe five years or so, where he buys high-end luxury homes. I think he owns 20 of them now. These are high-end properties that sleep like 20 people — a two-acre plot with a fancy four-, five-, six-thousand-square-foot home, basketball courts, tennis courts, mini putt-putt. He’s built a really good business making millions of dollars renting Airbnbs. He’s got a small team and it’s a proper company, not like a side project.
Shaan: I think it’s like a $50 million luxury Airbnb portfolio at this point, right?
Sam: I mean, I’m friends with Mark so he tells me a lot of stuff. I’m trying not to say any of the numbers because I forget what’s public and what’s private. Let you actually say the numbers — you’re probably getting it from his tweets anyway.
Shaan: Yeah, that’s just what he tweets out. You should follow him on Twitter, he’s a good follow. It’s cool to see — he’ll post like a before-and-after photo of these properties. Here’s what it was, and then we added a McDonald’s play place in the backyard. Like, he does dope stuff. And he’s totally under the radar — maybe two or three thousand followers on Twitter. Not a big-name person.
The Dollar Bill Side Hustle: Mark Jenny’s Origin Story [00:03:30]
Sam: So he tweeted this out the other day and I thought it was great. We haven’t done a blue-collar side hustle in a while. He said one of his very first side hustles — or early hustles — was selling dollar bills for fifteen dollars. Did you see this?
Shaan: Yes, yeah. Go, tell us the story.
Sam: So he tweeted it out — here’s the headline: “Guy sells one-dollar bills for fifteen dollars. Here’s how.”
He sees a dollar bill on eBay with Michael Jordan’s face instead of George Washington. He orders it, loves it, and he realizes — it’s just a sticker on top of a real dollar bill. You could go to Office Max and make these yourself.
So that’s exactly what he did. He creates an eBay account, starts selling them, and he starts averaging a hundred bills sold per day at $15 — which includes the shipping cost. His general profit was about $1,500 a day. He’s basically profiting around a thousand dollars a day doing this. Then he ramped it up and got to about $10,000 a day in sales. He became the largest seller of custom novelty collectible dollar bills on eBay.
Shaan: But it was a real dollar?
Sam: It was a real dollar. And you just add the sticker on top.
Shaan: Can you do that legally?
Sam: I guess so — why not?
Shaan: I don’t know, I just thought there’d be some weird rules around money.
Sam: No, I think you can do it. Like, people sell coins and whatever. It seems legit.
So then what he would do — he’s like, “How do I beat these other eBay guys?” He would run an auction, and then he would direct message everybody who didn’t win the auction, offering them the bill at whatever their highest bid was. Like, “Eight dollars was your top price — I’ll do it for eight.” So he started just racking up as many sales as he could.
That made him the top-ranked seller, which helped him in organic search. And I love this for a couple of reasons. One, it’s just another example of these little nuggets that shows you there are a trillion ways to win, a trillion ways to get rich. He was doing basically $365,000 a year in sales. He was a hundred-a-day guy. How old was he?
Shaan: You said he was in his teens?
Sam: Fifteen, sixteen years old. Amazing.
Modern Remixes of the Dollar Bill Idea [00:06:45]
Sam: These are the little arbitrage opportunities that come up, and I started thinking — what would somebody do if they were doing this now? Here are three ideas.
First, you could probably just do the same thing. What’s old is new. Try it on eBay or Etsy, pick a different celebrity face — Trump dollar bills is the obvious one, but maybe there’s other ones you could do.
Second idea: remix it. Keep 80% of the idea, change 20%. I would try to piggyback off whatever’s trending in movies or music. Remember when Superbad came out and there was the McLovin ID — the Hawaiian ID with the rainbow? I think you could just do McLovin IDs. Or take a prop from a movie — in Pulp Fiction they had the “Bad Mother” wallet. You could jump on that trend: “Upload your photo, I’ll send you yourself as a McLovin ID.” Use some AI things to create the avatar where it looks the same. You can print and laminate those very cheaply because they’re so thin.
Shaan: I wanted one of those.
Sam: Exactly. And then I saw some other ones on TikTok. For example — the second biggest Etsy store, maybe the first now, is this thing called Caitlin Minimalist.
Shaan: I’ve never heard of this. What is it?
Sam: I’ve got a whole thing coming on the pod — a full Etsy deep dive — but I’ll give you a sneak peek. One of the top-selling stores is Caitlin Minimalist. How she got her break: she was making jewelry for herself. Her friends were like, “Oh that’s cool.” Then a friend had a special request — her mom or dad had passed away, and she said, “The last thing they wrote me was this note. Is it possible to get their signature in their handwriting as a bracelet?”
She was like, “Yeah, I could do that for you” — and she just gave it to her for free. The friend was overwhelmed. Like, “This is the most meaningful thing in the world.” So she realized: people just want their name, their parent’s name, their kid’s name — ideally in their own handwriting — done in jewelry.
Shaan: How do you do that? You send her a picture?
Sam: Yeah, you send a picture of a piece of paper with the writing on it. There’s some tech that etches it so it matches the handwriting. It’s a metal piece — like a dog tag — but it’s cut so the name is actually cut out of it.
Shaan: How big is it?
Sam: Huge. She’s done like $80–90 million in sales. Probably two million transactions with an average around $40–50. She’s just this woman out of LA.
Mass Customization: Hoodies, Pet Socks, and the Trend [00:10:00]
Sam: I was on TikTok yesterday thinking about this idea, and I saw another one — a hoodie. Here’s a perfect gift for the holidays or Valentine’s Day: take a picture of you and your boyfriend, girlfriend, spouse, whatever, and it stitches a silhouette of that into the hoodie. So it’s a meaningful gift.
This is what they call mass customization. If you can figure out a manufacturing process to do this, there’s a lot of opportunity to sell these gimmick gifts that can and will work.
Do you remember Teespring?
Shaan: Yeah, the print-on-demand t-shirt company.
Sam: Really cool company started by Walker Williams. They were like one of the fastest companies ever to get to $100 million in revenue. The way they got popular was on-demand t-shirt printing with this hack on Facebook — you could target people by last name. “The one thing we all know about Smiths is that they love to party.” Or by location: “The one thing we know about people from Boston is they love blank.” Engagement on those ads was crazy. Their CAC was stupid low.
It’s the Dale Carnegie thing — the most beautiful word in any language is the person’s own name. Name, location, where you went to school, your friend’s name. If you can figure out how to incorporate those into ads, your click-through rate is insane.
Shaan: Pet’s face. There’s another one — pet face on socks.
Sam: I think I have a pair. Jungle Creations — if I remember correctly, at one point they did a million dollars in a week. You’d go on the website, upload a photo of your pet’s face, and they’d print it on socks and drop-ship it to you. In 2018 they did $17 million in revenue. Pet face on socks — same as celebrity face on dollar bill. Right?
We have a buddy who’s doing pet portraits — a painting of your pet, mass-produced. There are a ton of these little opportunities. And the click-through rates on ads for these things absolutely kill it.
Sam: Let’s see if anyone actually follows through on any of this. Mark Jenny is amazing, by the way. All right, let me switch gears.
Courses, Self-Consciousness, and “Me O’Clock” [00:13:30]
Shaan: So this guy made fun of me the other day for having a course, and it hurt my feelings. A friend — well, an internet stranger. A little bit of both. And it really hurt.
I’ve built a few businesses before. I’ve gotten to seven figures, gotten to eight figures, sold things. I should feel confident about this. And you and I both have courses. I’m going to actually launch another course that I think can be a million-dollar-plus-a-year income stream for me and my family —
Sam: It’s never good when you have to say “for me and my family.” If you have to justify feeding your family, that means the insecurity is poking out.
Shaan: Well, it gives context. The question I’m asking is: is it worth it? Because part of me thinks, “If I’m such a big shot I shouldn’t be talking about it — I should just have results and not teach.” But I like doing it, and it pays for my whole life. So…
Sam: Do you like it?
Shaan: Yeah, I like it.
Sam: All right, that’s enough. Do you feel like a fraud sometimes? You said something like that when we were interviewing someone — not a fraud, but…
Shaan: Self-conscious. Yeah, yeah. I make fun of myself about the course thing. Same thing — self-conscious.
I would say somebody who is really locked in — and I use the phrase “locked in” because it’s not just about how much money you have — somebody who’s truly locked in and obsessed with one thing probably would not do a paid course. Not someone who’s super wealthy necessarily, but someone who’s truly in it.
Sam: I think that’s wrong though. Warren Buffett had a course at Columbia. There are wonderful investors who’ve gone and taught. But I don’t think Warren Buffett was pocketing a bunch of money from a direct-sales type course. If I went and guest lectured at Stanford, drove 45 minutes, I’d be doing it for totally different reasons and it would feel completely different than saying, “Hey, I have my power writing course, go sign up and pay for it.” It just is different.
Shaan: My opinion about myself: I would say as long as I’m still doing courses, it’s part of my wandering-around phase — trying to figure out what I really want to do, what I want to do with my time.
When I was building my startup, I had no podcast, no angel investing, no courses. I didn’t tweet. I didn’t do anything, for seven years. Because I was fully locked in. It’s only after we sold that I started doing a bunch of other things.
That said, I think you should totally keep doing it. You said you like it, so keep doing it.
Sam: Let me share a little thing from my writing course. Students will ask questions like, “How much content is too much?” or “Should I wait until my product launches to start posting?” They ask all these questions that are kind of self-promotey, self-conscious. And I always say the same thing.
I go: “Before I answer that — hey, what time is it? I want to make sure we don’t go over.” They say something like, “9:34.” I go, “No, no — it’s me o’clock. You forgot: it’s always me o’clock.”
You’re thinking about what everybody else might think, what they might say, how they might feel. You forgot the main thing. It’s always me o’clock. You just have to ask yourself: do I like this? Do I want to do this? How do I feel about doing this? I’m going to do things based on that.
Shaan: Dude, there’s this funny picture of Fidel Castro wearing two Rolexes on the same wrist at the same time, just because he wants to flex that hard.
Sam: You need to get two watches on each wrist that just say “me o’clock.” Just to make sure this other one’s not broken.
Shaan: Exactly. So your question to me — I don’t even need to answer it. It’s me o’clock. You know what the hell you want.
Shaan’s List of Unpopular Truths from the Pod [00:19:00]
Sam: All right, you have another thing on here — the list.
Shaan: I’m gonna read the title and you go from there. It just says: “A few non-popular things I’ve learned from this pod.” Pretty good headline.
Sam: Eight out of ten.
Shaan: Thank you. I’ll say each one, you give me your reaction, and I’ll add more context.
Actually — can you give context on the whole thing? Where did this come from?
Shaan: I see a lot of things online where people try to explain rules — you have to work this much, or you don’t have to work this much — and the reality is there’s a million ways to get the same things done. For every example of one person succeeding one way, there are lots of examples of succeeding a totally different way. So I think it’s silly to have rules. I’ll see posts like, “It’s always a ten-year overnight success.” But I know people who had overnight successes where literally in three months their life changed. I think it’s silly to not acknowledge that. So that’s how I came up with this list.
Sam: All right, hit me. I’m excited.
#1: Overnight Success Is Real [00:20:30]
Shaan: First one — an overnight success, meaning one to six months — it’s absolutely possible and those exist and they’re real. Agree or disagree?
Sam: Give us an example.
Shaan: We covered a company called Brumate. In year one they got to like $8 million, in year two $20 million. I know a few people whose companies just took off in the first six months and it worked.
Sam: Your current stealth company — that hasn’t been mentioned yet — took off pretty quickly, right?
Shaan: Yeah, it succeeded pretty quickly. And how do you count that — overnight success? Or do you say, “I’ve been preparing my whole life for this”? That’s the counterargument. Like, I built up a reputation and I’m trading on that reputation.
Sam: But there are times you and I have talked to people — I had this guy on named Val. You know Val? He had a company that in year one made $10 million in profit selling ringtones on the internet. Some people just have the it factor. And luck is real. Sometimes you just nail it and it works. Not always, most of the time it doesn’t, but every once in a while it happens. For people to say overnight success isn’t real — that’s nonsense. I know a handful of 19, 20-year-old kids who within a few months had something making many tens or sometimes hundreds of thousands of dollars a month. It just works.
Shaan: I agree.
#2: Where You Live Matters [00:22:30]
Shaan: Here’s another one. At least early in your career, where you live really, really matters. It’s incredibly important. People who don’t move somewhere, I think they’re at a disadvantage.
Sam: A hundred percent agree. I did this.
Shaan: I was sitting in Australia, I wanted to do startups, and I went to a local startup event. I looked around — everybody’s being super nice, it’s Australia, everyone gets along great — and I thought, “Who’s the most successful entrepreneur in this room?” And it was this one older guy who had built something in the ’90s and just stuck around. Nobody else, pretty much.
The organizer comes up to me and goes, “Dude, you should give a talk next month at the meetup — this is great, we’d love to have you teach.” And I thought, wait — I’m 23, I’ve done nothing. If anything, that just means I’m in the wrong pond. I do not want to be the smart guy in the room. They should be like, “Dude, you should shut up, you don’t know anything.” That’s the type of room I want to be in.
So I literally went home, activated a T-Mobile phone plan with a 650 area code — Silicon Valley — because I was like, I need to mentally commit before I even move. Then I booked a ticket. My mom was like, “Where are you gonna stay? Do you have a job?” I was like, “I don’t know, I’ll figure it out. But I have a better shot of figuring it out there than I do from here.” That was my whole mindset.
Tony Robbins has a thing he says: “Proximity is power.” I’m a huge believer. I have taken jobs that looked like the worst offer on paper because I knew it would put me sitting next to somebody awesome. Six months next to that person does more for me than a higher-paying job would have.
It goes beyond business. If you want to make it in the movie industry, you have a higher likelihood if you spend at least a handful of years early on in Hollywood, putting in the time. There are funny stories about Bill Murray living in North Carolina, totally out of the loop — yeah, that can work, there are examples of that — but it increases your odds.
#3: Luck Is Incredibly Real [00:26:00]
Shaan: The third one — luck is incredibly real.
Sam: I know. Early in my career I was like, there’s no such thing as luck, it’s just hard work. Luck is real. I’ve told this story before — when we were selling our company, Brian Halligan, the CEO of HubSpot, got into a life-threatening accident two weeks after we closed. If it had happened two weeks before, it could have ruined the whole deal. I think you’ve had a couple examples where if one or two things happened a month earlier or later, it could have completely changed things. Luck is totally real and we dismiss it too often.
Shaan: I agree. I’d also say a big part of luck is in your control, and a small part is outside your control. Most of the luck you experience in life — a whole bunch at the beginning is outside your control: where you were born, your health, your parents. But a lot of what happens after that is in your control. We’ve done a podcast episode called “Four Levels of Luck” where we talk about actually manipulating luck to go toward your advantage — more practical, tangible stuff.
The last thing I’ll say on that — when I had moved to San Francisco and I was working with Michael Birch, I was trying to figure out: did this guy just get lucky? Because a lot of people would look at him and say that. He sold his company for $850 million. Two years later AOL wrote it off as a giant tax write-off and nobody uses Bebo anymore — Facebook won. So some people say, “Oh, he got lucky.”
But I don’t think that’s true — he’s built multiple successful companies. What I figured out was: it’s not lucky that he won, but it is lucky how much he won. He was going to be successful either way. But whether that number was $20 million, $80 million, or $800 million — there was a large degree of luck and timing outside his control. He could just as easily have been an $80 million guy versus an $800 million guy. The magnitude of success is a lot more based on luck, not the existence of success. He was going to be successful no matter what.
#4: Ivy League Schools Are Worth It (Maybe) [00:30:30]
Shaan: Next one — Ivy League-ish school, so let’s say top-20 university, is totally worth it. Even if you have to go into a lot of debt.
I think state schools where you get in-state tuition and still get a college experience are also totally worth it. But most everything in between — if you have to go into debt for it — I think it’s absolutely not worth it.
I went to Belmont University. I was fortunate to get a little scholarship and my parents paid. But it was $30 or $40 grand a year, and it’s a no-name university. Not worth it.
But I know people who went to Ivy Leagues. My wife went to an Ivy League school. You went to Duke. You have a handful of connections. If you go to Stanford, you have all these connections. That seems worth it. If you have Stanford on your resume, you’re going to get the interview. When people recruit, they scroll through a spreadsheet — it just says where you graduated. Bellarmine in Kentucky versus Stanford. Automatically higher likelihood of the interview.
But even more important than that — you’re going to meet people who have been around the world, who have rich parents. Those connections and that influence on your life? They actually matter. It’s worth going into debt for that.
Sam: I kind of disagree. I went to Duke — not technically Ivy League but considered up there — and it wasn’t worth it for me because I was not ready to figure out how to make it worth it. It is what you make of it. It’s not going to be handed to you just by showing up.
I had the totally wrong mindset. I thought: get good grades, eventually graduate, go to med school, do whatever I’m supposed to do. There was a track. But there are some people who made it worth it — the people who were like, “I’ve got these resources for free. I’m going to meet these two professors. I’m going to use my time here to socialize and spin up side hustles. There’s no better time to find co-founders and build a startup than when you’re in college.”
Some people had the right mindset. I did not.
Sam: I did have one phone call that was really important, and I’ll say it out loud because if there’s somebody who needs to hear this — maybe your dad doesn’t have the same sort of wisdom that mine did, so I’ll say it.
I called my dad my second year of college. He’s like, “How’s it going?” I was like, “I don’t know, it’s okay.” He goes, “What do you mean?” I said, “Grades aren’t great.” He goes, “What happened?” I was like, “They’re not terrible, I’m not failing, I’m just a B-minus student here. I was getting A’s in high school, so B-minus feels bad.”
He’s like, “Are you trying?” I said, “Yeah, I’m trying. But man — everybody here is smart. Everybody is just as smart as me, if not smarter. And they all work harder than me. This guy who lives next door to me is a genius. He just gets the physics right away. And outside of class, in the summers he drives an ambulance on the Palestinian war front — just for fun. And like, I don’t even know what to do in the summer.”
So I told my dad: “You’re paying a lot of money for me to go here. I could go to UT — state school, maybe five or ten times cheaper. If you want me to try, I’m willing to transfer. I don’t think I’m going to do that well here, so I don’t think it’s worth it for you to pay this much.”
And he goes: “Yeah. That’s the point.” He said, “You’re not there for the classes. You’re there because when everybody around you is like that, it raises your standards. You won’t even know what mediocre looks like. You think you’re mediocre — but that’s because you’re hanging out with exceptional people. If I take you and put you in a state school, you won’t have as many exceptional people around you. You’re not going to graduate at the top of the class — that’s not the point. The point is that becomes your network and becomes your normal.”
Shaan: You’ve proven my point by the way.
Sam: I know, I know. That’s the saving grace of it. Once that light bulb went on for me halfway through, I started to focus on getting to know those people instead of staying away from them. I realized: the point is to be hanging out with these people and become more like them, not feel like I’m competing with or intimidated by them.
#5: You Need a Technical Skill [00:37:30]
Shaan: Another one — and I’m going to merge a couple here. Having a technical skill — if we’re talking internet companies, that mostly means being able to code or design. In my case it was writing, which I think counts but is a little less critical. Having a skill is a massive advantage. Being a generalist is a excuse. You should be good at at least one thing. Coding or design would be better, but copywriting counts, and sales counts. You need to be great at something. Train for years to acquire it.
Sam: You know what’s the funniest version of a generalist? People who call themselves a polymath.
Shaan: That’s just — that’s done. If you gotta label it, you’re probably not it. You can’t be the one who calls yourself a polymath or a contrarian. It’s other people who have to point it out. You can’t nickname yourself “Brain” — that’s not how that works.
Sam: Same with humble — other people can call you humble, you don’t get to call yourself that.
Shaan: Polymath — you’ve fallen over the fence, Humpty Dumpty, and now you’re fully in a different land.
Sam: I think you’re a hundred percent right. You’ve gotta have some attributes. I hired a guy I thought was gonna be great — he was hustling, saying all the right things. Within a month I realized: this guy’s got no attributes. What are you good at? What can you do? “Oh, I can help with anything.” Okay, what problem can you go solve? What are you great at? If I hand you this thing, can you nail this part of it?
Shaan: A real generalist — the good version — is someone who is great at one thing, but decided not to just specialize as that one tool for the rest of their life. They’ve got one or two core skills they’re amazing at — paid marketing, copywriting, coding, sales — they could do that as their job, be in the top 10% if they specialized. They’re not in the top 1% because they’re not honing that craft every single day. But they’re top 10% at that and top 30% at four or five other things. That’s a real generalist. Not somebody who’s average at everything and great at nothing.
Sam: What did Ronda Rousey call it? A DNB?
Shaan: She was talking about this when she was on top in the UFC. She goes, “All these other girls are just DNBs — they just Do Nothing, you know.” And I was like, wow. That is an incredible phrase. So in my head when I hear “generalist,” I’m checking: is this person actually not just a DNB?
Sam: Leadership is a skill set. Getting things started, being the initial match that lights a fire — that’s a skill. But you’ve gotta actually be great at something.
#6: Assume People Don’t Change [00:42:00]
Shaan: Assume that people don’t change. That’s a safe rule. We have this attitude — maybe it’s an American thing — that people can change. And I do believe that’s possible. I’ve had demons in the past that I’ve overcome. I know other people who’ve overcome things. But it’s fairly rare. And if you are a person who talks the talk and doesn’t walk the walk, you will never change. If I meet someone like that I just assume: oh, they’re always going to be like that.
I used to have a different attitude when I started my company. “I’ll get these people and teach them how to be great.” As I’ve grown with this pod and talked to more people — the people who act a certain way have always acted that way.
Sam: My sister says people change for the worse — they Decay more often than they turn it around. I think you’re right. Same till proven different. You’ve gotta show something is changing. I don’t want to be the one who wants to fix them. I’d rather recruit people who are great and just let them do their thing versus somebody I’m going to train and turn around. No bonus points for making it harder.
#7: Time and Effort Don’t Always Dictate the Outcome [00:44:00]
Shaan: Last couple. I actually don’t think the time and effort put into a project necessarily dictates the outcome.
To build a company that makes you potentially worth hundreds of millions of dollars — in some cases, you don’t have to sacrifice balance. But to build these massive, world-changing companies — a Tesla, a Stripe, something creating tens of billions in value in 10 or 15 years — I think working 80 hours a week and having zero balance is needed.
That said, I think you can still achieve a huge amount of success compared to the average person and do it working 40 hours a week, or less after a while. That’s an interesting dichotomy, but I think it’s true.
Sam: I’ll go with that.
#8: Take Risks Before You Have a Family [00:45:00]
Shaan: Last one — this is one of the very few irreversible decisions. Having some type of success and taking a meaningful amount of risk before you have a family — before you have less time and less responsibility — is a massive advantage.
Getting an early win early in your career is huge. You’re at a disadvantage if you have a young family and haven’t yet achieved something and are now trying to go achieve it. It’s not impossible, but taking those risks early — people should be encouraged to do that more.
Sam: Paul Graham has an essay on this — I don’t remember the name but I read it in my early 20s and it stood out. He said something like: assume you start out with seven points as an entrepreneur. These are your capacity to take risks and achieve what you want. And then for each of these things — minus one for a mortgage, minus one for whatever, minus two for kids — your margin of error and the difficulty you’re going to have pulling this off gets tighter. He basically said you’re sapping your life Mana, your ammunition, by each one of these factors.
It’s an uncomfortable truth. Politically, the correct thing to say is “you can do it, you can do anything.” And if you’re 40, you shouldn’t be listening to this part — you should be saying, “Screw that, I’ve got wisdom, purpose, experience that a 20-year-old will never have.” Yes, you have different advantages. But objectively speaking, it is much easier to take risks when you have less to lose, less pressure, less stress, less financial obligation. It’s just a more game-theory-optimal way to play. You don’t have to play it that way, but I think it’s objectively a preferred path.
Shaan: And all of those rules I just described can be completely broken, and there are tons of examples of all of them being not true. But that’s what I believe to be true. That’s my list.
Sam: I like it.
The Gifting Business Opportunity [00:48:00]
Sam: Let me give you another idea. Do you do like company gifts for the holidays — send out gifts?
Shaan: No, that wasn’t a me thing.
Sam: Are you the warm, tender person — gifts are your love language?
Shaan: Words of affirmation.
Sam: A pat on the back is the greatest gift. The greatest gift is the lack of criticism I provided you today.
So I was thinking about this. At a previous company, the office manager would get everybody’s address and send these Harry and David gift baskets. Have you ever had one?
Shaan: No, what’s that?
Sam: Imagine somebody’s at the door. You go to the door. “Hey, we have this amazing huge gift basket for you.” You take it into your kitchen and you’re like, “Wow — what’s in this?”
Shaan: Chocolate?
Sam: Could be chocolate. It’s not chocolate though. What else?
Shaan: Like local foods? Bricks of salami and cheese?
Sam: There’s a little of that. There’s a little cheese, there’s some chocolate — but the thing that blew my mind was pears. These jumbo pears. Pears are the most underrated fruit. They are the official fruit of My First Million, as far as I’m concerned. Giant, delicious pears were in there. And I was like, “What the hell?”
It was the greatest gift I ever received. When you came over to my house, I don’t care if you were the cleaner or just some guy walking by — I was slinging pears to you because I had the juiciest pears that were going to go bad. They were massive and I needed to offload them. And everybody asked, “Oh wow, where’d you get this?” And I said, “My company sent it to me because they love me.” And that’s exactly how I felt.
So I started digging — what’s up with this Harry and David thing?
They sold to 1-800-Flowers for $142 million back in 2014. They have a couple of main brands — Harry and David with the gift baskets, Wolferman’s which is gourmet English muffins, Stockyards which is prime meats.
And Harry and David got me thinking about 1-800-Flowers. I did a little deep dive.
Deep Dive: 1-800-Flowers and the Gifting Industry [00:51:00]
Sam: 1-800-Flowers starts off as a phone number 42 years ago. Just 1-800-Flowers. And it goes on to build basically a $600 million-plus business. For a long time it’s just a phone number, then 1985 they start e-commerce. They have thousands of locations and fulfillment centers — not all owned by them, but fulfillment partners who can send flowers to you.
They’re publicly traded. What’s their revenue?
Shaan: What is it?
Sam: They did $485 million in Revenue last quarter. So they’re probably a billion and a half a year at a safe estimate. The gift baskets section — Harry and David — they did $148 million last quarter, so that’s probably a $500 million-a-year business. Florals were $300 million. Then they’ve got Cheryl’s Cookies — bought for $40 million — they’ve got Sherry’s Berries, the Popcorn Factory — bought that for $30 million back in the day, personalized gifts for $250 million. They own all these brands.
So I’ve also been doing this food gifting thing lately because I’m trying to get better at gifting. Inspired by our buddy Ramon, who is a prolific gifter — the best. He highlighted my gifting deficiencies. I said, all right, I’m going to start sending gifts. But I’m not a big plan-ahead guy. Day of — where do you get a last-minute gift that can get to someone’s house same day, same hour?
Shaan: DoorDash and Uber Eats.
Sam: That’s what I’ve been doing. I’ll just DoorDash you food. Food is the universal love language. I’ll send you a pizza and wings. I’ll send you four slushies, boba tea, a Cinnabon. I’ve got a whole menu of gifting foods. I gotta know what you like — I know you’ve got that sweet tooth. I might hit you with 16 pints of ice cream. You’ll be like, “Sam, this is simply too much ice cream.” I’ll be like, “I know, because I love you that much.”
The Business Idea: Birthday Eats Cloud Kitchen [00:54:30]
Sam: Somebody should build a 1-800-Flowers type of brand, but the things I’m gifting aren’t made for this. The Cinnabon is not made to be sent to a friend for their birthday. I think somebody should build something like “Birthday Eats” — last-minute gifts on DoorDash — as a cloud kitchen. Nationwide, optimized for gifts. Baskets that are nicely put together with a bow. Handwritten notes that are part of it. A little trinket. Something that shows this is for the occasion. And help me help you help someone else.
Shaan: I completely agree. And not just a cloud kitchen — a clout kitchen. Where you partner with a celebrity to be the face of this last-minute gifts brand. Gourmet gifts, launches nationwide across Uber Eats. Who’s our celebrity partner?
Sam: I thought of Ryan Seacrest. I don’t even know why.
Shaan: Hardest working man in Hollywood. I haven’t seen his face in that app. I think he would like to be in that app. White women like him, universally not hated, recognizable face. But who else? Who could be the guy or the gal?
Sam: Mariah Carey — she’s seasonal.
Shaan: Maybe Mariah needs to get out of the song game and get into the gift game.
Sam: I do think this is brilliant. I’ve tried to order 1-800-Flowers the morning of Valentine’s Day and they don’t let you. They’re like, “It’s too late. If you really loved her you would have done this three days ago.” It’s super annoying. I’m totally on board.
Can you not do something like this now? If I open DoorDash right now — let’s see — I can get an Edible Arrangements. Also a great gift.
Shaan: Yeah, those are good. But I think we need a fresh brand. On my app there’s the “Flower and Gift Boutique” — and it’s flowers, basically. Roses, a cookie in a bag. A bath bomb. Come on. Mariah and Ryan Seacrest aren’t going to lose to a bath bomb.
Sam: I completely agree. I’ve studied 1-800-Flowers — they’re a really interesting company because they share all kinds of insights in their annual reports. One report said succulents are growing amongst millennials. I read that in 2018, told a couple of people, and they started succulent delivery businesses geared toward millennials and they killed it. There’s now The Sill and a couple others.
Another insight from 1-800-Flowers: they said they don’t make a lot of money from flowers, but they make a ton of money from vases. So I’m like — why aren’t you painting cool art on the vase and getting people to spend more on it? Like a Frida Kahlo painting on a sick vase — I’d pay $50 for that.
Their annual reports are worth reading because they have such interesting insight. They’ve been doing this since the ’70s.
I love the gifting business. But their market cap is kind of rough.
Shaan: Why is their market cap so bad?
Sam: $600 million. It’s horrible. Just plummeted over the past year — well, everything has plummeted. I think their name is Jim McCann — he founded it — and his son is now the CEO. Jim is a really interesting guy. I’ve talked to him on the phone a couple times. Fascinating person. It’s almost like a really weird family business.
Omaha Steaks and the Gifting Moat [00:59:00]
Sam: Another one that falls in this category — have you ever studied Omaha Steaks?
Shaan: No. But that just sounds like exactly what it is.
Sam: So Omaha Steaks is a mail-order business. They sell steaks. You want to buy someone $200 worth of prime rib, filet mignon, chicken, and bratwurst? You order from there and they send it. It’s an awesome gift. I believe it’s privately owned — I wouldn’t be surprised if it’s north of a billion in revenue.
They were one of the very first companies to take advantage of internet marketing. Right when the internet got popular you saw Omaha Steaks ads everywhere. They were very progressive about figuring out how to market online. And they’re still really fascinating.
Shaan: Are they mostly in stores?
Sam: No, no — it’s 100% online, and originally a catalog. The classic gift is a $90 package of steaks. That’s a great gift. My best friend Neville, who’s also my neighbor — his mom always sends Omaha Steaks. Whenever he gets an order, we all go over and grill them. It’s an awesome gift.
Shaan: I’m shocked you haven’t heard of them. But you also didn’t know who Dolly Parton was, so.
Sam: Yeah, exactly. Anyway — look up Omaha Steaks. I think they’re in the $600–$700 million-a-year revenue range. Founded around 1920. Been around forever. They are incredibly sophisticated, at least in terms of internet marketing.
Shaan: This seems like the type of thing that could be done with the right influencer partners. A slightly different version of this.
Sam: Their moat isn’t manufacturing. Their moat is that it’s been around so long that you grew up seeing your parents gift it to people, and then you do the same thing. Like See’s Candy — why does Warren Buffett like it? “I don’t know, it’s just the default gift that men give.” People have seen their parents do it for years and then they grow up doing it.
Shaan: The local See’s Candy near me — they opened a nursing home in the store because everybody there is so old. It’s incredible.
Sam: See’s Candy is pretty good, though. You get some truffles, or a turtle — chocolate turtles are great.
Shaan: Nothing to bat an eye about.
Sam: Yeah, look up Omaha Steaks, look up 1-800-Flowers. These are really interesting companies to study. You think “Omaha Steaks” and you kind of judge them — like, oh it’s just some Omaha company, they can’t be that sophisticated. They are incredibly sophisticated in terms of internet marketing.
Closing: What’s Coming to the Pod [01:03:00]
Shaan: All right, cool. Let’s cap it here.
Sam: By the way, there’s a bunch of fun stuff coming. I want to do the studio tour and breakdown — what we learned from the studio change, what it cost, all that good stuff. I want to do our annual awards, we’re going to drop the new intro music, we’re going to talk about where the pod’s going. The next two weeks I think we’re going to have some fire podcasts.
Shaan: We gotta do the Millie Awards. Let’s get Andrew Wilkinson booked again. And we have Austin Reef — I’m excited for that. It’s going to be a good couple of weeks.