Shaan recaps a San Diego founder weekend where he rented a luxury Airbnb from RV Share founder Mark Jenney and invited a diverse group of entrepreneurs including NFT founders, a former CIA operative, the Gel Blaster toy founder, and mini Katana’s Isaac. The episode covers the lessons from each encounter, the fascinating differences between entrepreneurs at different life phases (teens through 70s), and Shaan’s reflections on what he’s learned watching HubSpot run The Hustle versus building it himself.
Speakers: Sam Parr (host), Shaan Puri (host)
The San Diego Weekend [00:00:00]
Shaan: Amazing weekend. I want to tell you about it.
Sam: Go for it. I want to hear about it.
Shaan: So we’ve done these before, but I’ll explain how they work. About once or twice a year we go somewhere, rent an Airbnb, and have four to five founder friends hang out for the weekend. By the way — sorry you should have been there. I don’t know why the invite got lost in the mail.
Sam: Don’t worry about it. I’m worried about it. You’re lucky I couldn’t have made it — but I’m worried about it.
Shaan: I was actually going to text you while we were doing it. I was like, “Wait, why isn’t Sam here?” I asked Ben, “Did Sam say no, or did we just not tell Sam?” He was like, “I don’t know, the whole thing got screwed up.” We’d bumped it back twice, so who knows. Basically: new year, let’s get together.
Shaan: We went to San Diego and rented an Airbnb from Mark Jenney — you’ve mentioned him on the pod. He founded RV Share, which is like Airbnb for renting RVs. Grew it and sold it — I think to KKR — for around a hundred million dollars. He’s actually sold it twice in pieces. He’s got a crazy story — I think he was homeless at one point and made the whole thing happen. Very inspirational person.
Shaan: Mark now has a luxury Airbnb portfolio worth about $50 million. About 20 properties, all aimed at over-the-top destination experiences — bachelor parties, golf trips, family getaways. This one was in San Diego, and the backyard was insane. Basketball court, pickleball court, wiffle ball field with a full fence like a baseball diamond, golf, pool, sauna — full boy paradise. Inside there’s a poker table, pool table, everything.
The Guest List [00:08:00]
Shaan: The first day was just sweaty male bonding — playing every sport available. Second day, I tweeted out “who’s in San Diego” and a bunch of people replied. Ben curated it and we invited 15 people over. Let me set the scene.
Shaan: First: two guys who own NFT projects that have done $200 million-plus in sales. Both under 23 years old. One of them didn’t even have a public identity until a month ago. People know Frank from D Gods — that’s the number one project on Solana, basically the Bored Apes of Solana. He basically said, “Here’s my real identity,” so he can now show up to parties and say what he does.
Shaan: Then there was the DTC crew. One guy created something called Gel Blasters — think a Nerf gun but with gel pellets. Went from zero to tens of millions in revenue in a year. Has this crazy story where a big toy company pretended to buy his company for like $100 million, did due diligence, he shows them all the CAD files, the design specs, everything — they walk away, and three months later launch an identical product to compete with him, basically stealing his whole influencer marketing plan.
Shaan: The Mini Katana guy, Isaac, was there — we’ve talked about him before. He does eight figures in revenue without a single dollar in ads, not out of pride but because Facebook literally won’t let him advertise. “This is a weapon, you can’t advertise swords on Facebook.” So he had to get creative with organic content. He said he was listening to the podcast while driving and heard us talking about a katana store and almost drove off the road. Super nice guy.
Shaan: Then there was a former CIA operative — this is someone you actually interviewed for the pod, but we couldn’t release it.
Sam: Yeah, we don’t even need to say more. That already sounds juicy. We couldn’t release it because he said a bunch of classified stuff.
Shaan: Right. Without revealing too much: it’s almost as if they convince people in other countries to become treasonous spies. If you’ve watched Jack Ryan, this was the real-life Jack Ryan. And then he left the government and created a business, so there was great overlap.
Shaan: I asked him, “How do you convince somebody to work for the US government against their own country?” He said, “Two years of rapport building, then it’s manipulation.” Then he goes, “Remember earlier when we were getting a drink? You said you really wanted X.” And I was like… no? He’s like, “In passing, you mentioned something.” He said, “For about a year I build a file on this person — every want, every need, every problem. I keep that file for years before I flip them.”
Shaan: Needless to say, I didn’t want to talk to that person anymore. He’s very charming. When he tells a story, you’re captivated. I called four people over. He told another one. I called three more. He had this thing where I said, “Look — if the next story is bad, no problem, you already won. This is just a bonus lap.” He gave us one more and it was a banger.
Shaan: My friend Jason Hitchcock has this thing he says: “You say one interesting thing, I say ‘interesting.’ Two interesting things, I say ‘those are interesting.’ Three interesting things, I say ‘you are interesting.’” That’s what happened by the third story.
Ramon’s Electrician Story [00:20:00]
Shaan: And our buddy Ramon was there — with his son. Ramon recently became a US citizen, which was the big thing. Before he arrived we went and got him a cake from Safeway and had them write a message. The guy misspelled “welcome,” so it said “Welcom to America.” Sounds like the most non-American thing ever. Ramon thought it was perfect.
Shaan: His son Victor was in the car afterward and every time someone called he’d answer: “Hello, fellow Americans.”
Sam: Amazing.
Shaan: So at the dinner party we did an icebreaker: “What’s the weirdest way you’ve ever tried to make a buck?” Because otherwise in a room full of successful people everyone just goes into their script and it becomes this weird one-upmanship thing. The neg-the-whole-group icebreaker.
Shaan: Ramon had ten of these stories. He’s very quiet but once you get him going it’s like an endless vending machine of stories you’ve never heard, even if you’ve known him for ten years.
Shaan: He says: “Back in the day I was 18 years old, I wanted to start a painting business. Needed money. I put up a thing that said ‘I’ll paint walls.’ But then, being the hustler that I am, I thought — how can I widen the top of the funnel? So I just said ‘general contractor, I’ll fix anything.’ And I put it on the Dutch Craigslist.”
Shaan: He gets an inquiry: “Hey, I need an electrician for some electrical work.” He thinks: “Great, I’ll be there tomorrow morning.” Goes to the Home Depot equivalent and looks at vests: “Which one makes me look most like an electrician?” Like Halloween — he’s trying to find the costume.
Shaan: Shows up. The guy says, “Cool, so we need 40 amps here, we’re going to run a line under the circuit over here…” And Ramon’s like, “He’s saying words. I don’t understand the words he’s saying.” He’s writing everything down. Vest on. Clipboard in hand. The guy explains this incredibly complicated job. Ramon goes home, reviews his notes. He doesn’t know what any of it means.
Shaan: Goes back the next day and says, “Listen, man. I’ve never done electrical. I just needed money. I thought I could figure it out. Slept on it. Turns out I can’t.”
Shaan: And the guy goes — “What the…?” Then: “You know what, kid? I respect the hustle. I also respect that you were honest. And here’s what you should actually do: you don’t need to know how to do electrical work. You got the job. Now you just need to find somebody who does know and subcontract it out. Keep a margin.”
Shaan: Ramon started an actual general contracting business doing exactly that. He made close to a million dollars running that business. Then he immigrated to America, created a Brazilian music festival, lost it all, created more internet businesses, made it all back, lost it all again, made it all back again. He’s done that cycle several times.
Shaan: Even his current business — Alpha Paw, dog ramps and dog products — has been that same ride. When COVID hit, shipping container costs went from $3,000 to $20,000. His unit cost blew up. His response: pivot to cats. He made a kitty litter product called Genius Litter, and he just got into PetSmart nationwide. He’s back.
Life Phases: What Each Decade Cares About [00:32:00]
Shaan: One big takeaway: there was this fascinating spectrum of life phases at this event. We had pre-teens, guys in their 20s, guys like us in our 30s, guys in their 40s, and then I went and met a couple in their 70s. And the differences were stark.
Sam: Let me guess. The 22-year-olds are like, “Let’s do everything.” The 30-year-olds are wiser. The 40-year-olds are like, “Pick and choose.” The 70-year-olds are like, “None of it matters.”
Shaan: That’s exactly right. The pre-teens — totally into play. They’d be on the pickleball court and in between points they’re running to kick a soccer ball. Right afterwards: “You want to play Monopoly? You want to do this?” Till the last minute of the last second of the day — “You wanna play?” That energy was amazing to be around. They were also doing Khan Academy just for fun. Blew my mind.
Shaan: The 20s were the “I’ve got it all figured out” guys. And they do have a lot of life figured out — they’re ahead of the curve. But the problem is they think they’re at the end of the curve. I listened to them and thought, “Four out of ten things you just said were totally wrong — but you know what? The fact that you believe all ten is going to work.” They’d only known winning. As you get older you take Ls — health Ls, you see friends take Ls, you make expensive mistakes. That humbles you. I loved their energy. I was like — pass the delusion please, I’d like a sip.
Shaan: The 30s — weird middle state. A lot of self-belief, but now I know how expensive it is to go down the wrong path. The 20-year-olds who created the NFT project were just able to do something stupid and it paid off. The Gel Blaster guy made a gel Nerf gun because it looked fun — that was enough justification. Where the 30s guys would be like, “That looks fun — let me spreadsheet this out real quick.” When you have something to lose it changes things.
Shaan: The 40s were: “I know what I’m doing. When I hear about what everyone else is doing, I’m half amused and half exhausted. I don’t need to be in NFTs or learn TikTok sword sales. I just want to go relax.” And one guy had just found out he had high blood pressure, so he had a blood pressure monitor and was taking readings four times a day. They understood compounding. They knew their lane. They weren’t seeking the next hit — they had a hit and they were enjoying it. Their own mortality was more on their minds than proving themselves.
Shaan: The 70s: combination of “I want to contribute” — philanthropic projects — and just happy we came over. When we were leaving I thought: once we leave it’s going to be really quiet here. The things that mattered to them were their grandkids, their kids marrying the right person, figuring out how to contribute, and not having their house be too quiet. Our being there was a cool, fun change of pace. I was like — yeah, when I’m 70 I’m probably going to want that too.
Storytelling Wins [00:45:00]
Shaan: Another big takeaway: storytelling wins. There were a lot of equally impressive people at this event, but the ones who understood how to tell a story stood out, made connections, got help and introductions. The people who didn’t understand how to tell their story — just told facts. “I’m Steve. Everything’s been great.” Alright thanks Steve, see ya.
Shaan: And there were nuances. Some storytellers — every story was about how awesome they were. You could see it repelling people. But the CIA guy had a great rule: “I only tell CIA stories where I look like an idiot. I never tell the ones where I beat the bad guys and everyone clapped.” Great rule in general.
What Shaan Learned Watching HubSpot Run The Hustle [00:52:00]
Sam: It’s been about two months since the Milk Road acquisition and your HubSpot tenure is wrapping up. What have you learned from watching the buyers’ perspective?
Shaan: A few frame-breaking things.
Shaan: First: building something from scratch is a very rare skill. One or two focused entrepreneurs with almost no money can probably do more in six months than a 50-person team with millions of dollars in 12 months inside a large organization. The creative types bold enough to go build something either aren’t working at that company — they’re out doing their own thing — or they’re stuck in this political game where they want to impress their boss. They don’t have the upside to see the win. They don’t get the dopamine rush of the sale. So it’s actually really hard to build something from scratch inside a large company, which is why it’s worth it for them to just buy something that’s already working.
Shaan: When an acquisition happens, the velocity of progress slows down like molasses. Other things get better — stability, redundancy — but the velocity and the pace and the aggression go down.
Shaan: Second: I used to dismiss big companies as idiots. That’s not true. Operating well is genuinely hard. A lot of what we make fun of — bureaucracy, meetings — creates redundancy. Redundancy creates predictability. Predictability creates value. That’s why your anxiety goes way down as an entrepreneur when you join a big company. Frustration goes way up, but anxiety way down.
Sam: I agree, though the main value I saw inside a big company was distribution. When you’re big, you either give something more distribution or you can just follow other people’s innovation — you don’t need speed when you have size. A sumo wrestler doesn’t need to sprint. And you trade that size for speed. At a startup, mistakes aren’t expensive — no customers to lose, reputation to burn, press not watching you. When you’re big, every move matters and every mistake is expensive. So they’re not slow because they’re stupid; they’re slow because they’re smart.
Shaan: Third: a lot of the best things start completely illogical. This podcast — “My First Million” is kind of a terrible name. The Hustle was kind of a bad name. A newsletter? When I was pitching bigger companies on it they said, “This will never be big.” But when you’re two guys beholden to no one, you just say, “Screw it, we’re doing an anti-Black Friday sale where we charge more.” Completely illogical — and illogical stuff works sometimes.
Shaan: And there’s something the 70-year-old guy said: “Picking is hard. The problem with picking is that today she might look like a pimply awkward person, but 12 months from now as you develop the idea, change one thing, get a new wardrobe — all of a sudden she’s got her PhD and she’s inheriting $72 million.” The best ideas don’t always look like the best things up front. That’s a Peter Thiel line: the best ideas are things that sound like bad ideas but are actually good ideas. The least competition, the most green field.
Sam: The Hustle is about to cross three million subscribers.
Shaan: That brings me to the last point: planning. When people talked about OKRs I was like, “How about a weekly one? Every day is a new adventure.” That’s important for starting out. But at some point — maybe at $10 million or $100 million in revenue — planning becomes necessary. What the people running Milk Road now do is they put more money into growth, hired more people, and they don’t panic. Those are the three differences. Their approach has some bad things and some great things. We’ll see how it plays out.
How to Hire a Researcher [01:08:00]
Sam: While I have you — I have 400 applicants for a researcher role, narrowed it down to 200, and I don’t know what to do with these people. How do I figure out who to hire?
Shaan: Don’t interview 400 people. Give them all the same assignment: every week, here’s what we do — I want you to surface interesting nuggets that I might find interesting. Do it for two weeks, pay them a small amount, like $250. Then cut the bottom half right away. The rest you have do it two or three more weeks, because a lot of people could do a great MFM episode once. I don’t know how many could do it 100 times a year. You need a researcher who has a steady inflow of information they’re curating.
Shaan: The second thing is give them a research format. Here’s what I give mine: first, the frame — how would I just bring this topic up on MFM out of nowhere? The frame is the hook. Second: four or five interesting bullet points I could say about this thing that would make you go, “Oh, that’s interesting.” Third: the take — what should people be doing with this?
Shaan: Example: the nugget was “I bought a car from an anonymous account on Twitter.” Cool. But we changed the frame to “the Guy Mafia” — there are all these anonymous accounts that are specialists in one niche, and maybe there’s a bigger topic there. The take became: you should be doing this with a girl anonymous account, and monetize not with a newsletter or paid community but by actually selling the thing — selling me the car.
Sam: I need you to send me that format.
Shaan: I will. Most people are bad at the frame-take structure, but them doing it poorly is still helpful because you’re like, “No, that’s a bad frame — the frame’s this.” Better than a blank page.
Sam: All right. Let’s get out of here.