Sam just survived losing both his car key fobs somewhere on a Tennessee highway, which leads to a discussion about private jet haggling and road trip observations about American spending patterns. Then Sam and Shaan dig into the NCAA NIL rule changes, mapping the inflection point framework to business opportunities — cameo, Barstool Sports, athlete compliance software — and round out the episode with Zapier for sounds, a renter loyalty rewards startup, and the pattern of white-labeling enterprise tech for small businesses.
Speakers: Sam Parr (host), Shaan Puri (host)
Recap [00:00:00]
Sam: We had a good episode. We talked about the Zapier for sounds idea. We talked about the opportunity now that college athletes can make money — what are the business opportunities around that. And Shaan, you actually gave one of the better ideas in the last three months that we discussed, which is kind of interesting.
We also talked about a new company creating a search engine for company documents — sounds boring, but it could be quite a big business. And the last thing: this business model idea of taking the R&D that big companies do to build custom software — like the Starbucks mobile app or the Domino’s pizza ordering app — and making that available to all the mom-and-pop shops. We did a bunch of examples of where the opportunities might be.
Sam’s Tennessee Car Key Disaster [00:01:30]
Sam: All right, I’m in New York, and I had a hell of a week. Let me tell you this story.
I’m driving from Texas to New York. Got my dog, this nice car, loving it. I’m fifteen hours into the drive. I get out of the hotel room, I’ve got my two spare keys on the same ring — you can’t leave a spare key in the car because it won’t lock. When I get to the hotel I put them both on one ring, and when I get back in the car I separate them.
So I’m on the phone with my mom, first thing in the morning. I put both keys on the roof of the car for a second while I get in. Start the car, drive off.
Sixty minutes later I stop for gas. The car tells me it can’t start because the keys aren’t present. Where are the keys?
I left them on the roof sixty miles back.
Shaan: Oh no.
Sam: I go back. Many hours of searching. Someone ran over both key fobs. I find the destroyed pieces. Thankfully I also find my bike keys and the Thule rack — those were locked to the roof and I was worried I’d have to call a welder to cut them off.
But the fobs — $800 to $1,000 each — completely smashed to bits. I call Mercedes. They say we can’t get a new key until Thursday. This is on a Thursday. I’m stuck in Tennessee with my eighty-pound pit bull and can’t fly because of the dog.
Shaan: I got a text message in our group chat that said, “How much does a private jet cost? I need to get to New York. I’m stuck in Tennessee.”
Sam: So I googled “Nashville private airport” and emailed them: “Look, I want a private flight either right now or first thing in the morning. My budget is $7,000. Do you have any pilots that want some quick work?” They said it usually costs $15,000. I said, tell me if you have someone with availability — because like they’re just small businesses. Can I haggle? They got me another quote and it ended up falling through, but I realized you could totally negotiate with these people.
Shaan: The hotel thing is great — anyone can do that. If you have a little social media following, you’re good. I’ve never done it, I probably still won’t, but it’s a great tactic.
Sam: Here’s what I learned: I’ve flown private once or twice, never paid for it. I learned what to do when you’re stranded: what private jets cost, whether you can commission one on short notice, whether you can hop on someone else’s flight. Somebody from our listener community even offered to drive my car to New York if I’d hang out with them for 30 minutes.
Road Trip Observations: America’s Spending Boom [00:09:00]
Sam: A few things I noticed driving cross-country. Number one: the average American eats so poorly. I’m not the healthiest — I like Diet Coke, I’ll eat McDonald’s — but when you’re on the road and you go to a gas station or fast food place and just watch what people order… lines are packed for Ralley’s, Sonic, Hardee’s. This whole healthy eating thing is very popular among affluent people. It’s not popular everywhere.
Shaan: You didn’t see a lot of keto and intermittent fasting on this road trip.
Sam: No. Just processed food, sugar, caffeine. Gas, sugar, caffeine. Repeat.
I got pitched this company called Daily Blends — a healthy vending machine that dispenses ready-made meals in jars. Instead of a Twix or a Red Bull, you push a button and get a pre-made meal. Smart because they’re going after hospitals and corporate accounts where there’s pressure to have healthier options. They charge way more than a typical vending machine. It’s a similar model to Bevvy — the water company — which became like a billion-dollar company.
Shaan: The guy who came on to talk about vending machines once said most of America just wants a Monster. But you can do really well in specific prime placements: hospitals, airports, corporate offices that are incentivized to offer something better.
Sam: Second thing: I am so bullish on America over the next two years. Every rental car place — sold out. Hotels sold out. Roads are packed. I talked to people earning $50K to $150K a year, and I said how much money have you saved? And they said more than they’ve ever saved in years. And what are you going to do with it? They want to spend. They want to buy a Rolex, they want to travel.
It feels like the roaring 2020s. People are ready to go after being sheltered in place for over a year.
The NCAA NIL Rule Change and Business Opportunities [00:16:00]
Sam: Okay, let’s do ideas. The big one is the NCAA thing.
The law changed to allow college athletes to make money off their name, image, and likeness. Previously, if you made money as an NCAA athlete, you lost your amateur status, couldn’t play your sport, could even have your scholarship revoked. Overnight, a bunch of opportunities opened up.
Shaan: Can you explain the rule? Is there anything weird — like can they not actually access the funds yet?
Sam: I think they’re already signing contracts and getting paid. I don’t know all the fine print.
So I had this suitemate in college. If you Google “Pure Sweat Basketball” — this guy named Drew Hanlon. He’s the trainer on Instagram you always see with every NBA player. I knew him in high school, we went to college together. He was my suitemate, I was a Division I track athlete.
He was always working nights on Pure Sweat. He didn’t drink, didn’t party. He started with literally a binder of paper workouts he’d sell for $50 to kids in the neighborhood. Eventually made a website and app. After college he started training the guys — Anthony Davis, Bradley Beal, Zach LaVine — and he has this app that’s maybe $100 a year. I bet he makes $5 to $10 million a year off that.
And in college he was in the compliance office all the time, making sure he was following the rules with Pure Sweat, because they were strict.
Shaan: So the easy opportunity now: you’re going to see loads of “little Pure Sweats.” Super simple apps with basketball workouts for $100 a year. Low-hanging fruit.
Sam: Right. My best friend Trevor was a kid from Wyoming who tried to walk onto the Duke basketball team — five-foot-nine white guy who was the best high school player in his state. He almost made the team, got the last guy cut. Long story. But in the summers he’d go back to Wyoming and run camps. $100 per kid, three camps running simultaneously. He’d make his whole year’s worth of money in two and a half months. Coaches — that’s the money-maker.
Shaan: So here’s what I saw happening. First: Cameo was a winner. All of a sudden every athlete put themselves on Cameo. If you go to Cameo’s NCAA page, there are already 17 pages of people available. And they’re all so cheap — like $25 each.
Second: Barstool Sports. Dave Portnoy went online and said “emergency press conference” — announced Barstool Athlete. An athlete DMed him: “I’ll be the first Barstool athlete.” He’s like, okay. A volleyball player from whatever school. Tweets it out: didn’t even say what it is yet, and people are signing up.
Barstool basically said: if you play Division I sports and you blink at me, I’ll sign you. I’ll send you a T-shirt. You want pizza? You want money? I don’t know what’s going to happen here, but we may just become the most powerful agency in the world.
Sam: And that legitimately could happen. Athletes can now have lawyers, agents, brand deals. Barstool has the brand that’s super loved among college athletes. Level four luck — your reputation is so strong that luck finds you.
Shaan: The most interesting idea though, the one I think is the best thing I’ve said in the last three months: these athletes have to report their deals to their schools. You can’t just do anything — you have to report it. And most athletes are not going to do a good job keeping track. How much they got paid, when, what the terms were, what collateral they need to report to the NCAA.
Somebody who builds the back-office reporting tool for that — that underlying infrastructure layer — is going to become incredibly valuable.
Sam: That’s the best idea you’ve had in a long time.
Shaan: Think about it like Carta or AngelList — underlying platforms that sit underneath the entrepreneur. Universities will pay tens of thousands a year for this software. And you’re sticky — they’re not going to switch two years in because some other system has a new feature. Then you build the add-ons: banking, contracts, deal marketplaces, all on top of the system of record.
Sam: We actually invested in a company called Stan. It’s basically a link-in-bio tool that lets athletes and creators do commerce — booking calls, selling things. That might play in this space, though it’s a slightly different angle.
Inflection Points Framework [00:28:00]
Shaan: The NCAA thing is interesting, but what’s even more important is the concept of inflections. There are these cultural, political, or technological moments where a new thing becomes possible — and that’s when big businesses get built.
Mike Maples has a blog post on this. Examples: everyone has an iPhone, so GPS-based apps are now possible. Being gay is accepted, so a gay dating app makes sense. Weed is no longer frowned upon, so cannabis businesses open up. Two years ago, telemedicine laws changed — huge opportunity that has since partially reversed. Sports gambling — companies that had terrible businesses suddenly had amazing ones when the law changed. The UFC wasn’t allowed in New York for years — then it was.
This is one of those moments. In 20 years we’ll look back at the NCAA NIL ruling and think about all the businesses that came from it.
On the regulation side: GDPR came out and you saw companies like OneTrust emerge. OneTrust is probably the fastest-growing enterprise SaaS company of the last 10 years — over $200 million in ARR, probably a $5 billion valuation. It’s GDPR compliance as a service: hey, big company, making the changes required by the new privacy laws will take your lawyers and engineers months — let us do it for you.
Same with Obamacare. Look at United Health’s stock chart — flat, flat, flat, then goes from $24 a share to $400 a share starting around 2009-2010 as Obamacare kicked in. That was a better investment than Amazon, Google, or Netflix during the same period.
Sam: I’ve heard this story many times. Jesse Pujji built Ampush, a digital marketing agency working with Dollar Shave Club and Blue Apron. He told me: we were just doing this other thing, it wasn’t quite working, and then Facebook launched News Feed — or Google launched AdWords — and we jumped on it. And that was their start.
Our friend Sully: he quit Microsoft, moved back to his parents’ house, was just browsing the internet and saw Facebook launched its app platform. He built a simple dumb app the same day. It immediately went viral because Facebook was rewarding early app developers. That was his start.
I’ve heard this so many times: you just need to be in the market. You need to be in the game. Even if your current thing isn’t working, if you’re aware of these inflection points and already running, you’re the perfect person to pivot. You’re not at a cold start. You’re already jogging.
Nira: Document Security Search Engine [00:38:00]
Sam: All right, you want to do another one?
Shaan: Yeah. I found this company called Nira — formerly called FYI. It was started by Heaton Shah, who was Neil Patel’s right-hand man and operator at QuickSprout.
What Nira does: if you’re a company with 3,000 employees, your Google Drive alone has a terabyte of data. Hundreds of thousands of documents. And you have two problems. One, it’s really hard to find things. Two, you have no idea who has access to what.
For example: you have a document called “Salaries” and you accidentally shared it with an entire folder. You don’t notice. Someone quits and they still have access to your passwords document. This happens constantly.
Nira is basically a security platform that lets you see, in one interface, who has access to what across all your cloud storage — Google Drive, Dropbox, Box, whatever — and you can revoke access, fix vulnerabilities, and audit your documents.
Sam: I didn’t even realize this was a problem until someone described it. It’s like — oh, this is just the way the world is. You live with it until someone says you can fix it.
Shaan: And here’s what’s interesting about the company: they’ve been working on this for two years without getting any customers. Because to sell enterprise security software, everything has to be buttoned up. The sales cycle is six to eighteen months. You need to sell into the IT department, where everyone is uptight (as they should be).
That’s not the DNA Sam and I have. We do stuff and make money in five days. But it’s really cool to see inside that world — the epic planning, the three-year roadmaps, spending $2 to $5 million on ten engineers before getting a single customer.
Bottom-up SaaS vs. enterprise sales. Completely different games. Enterprise sales is incredibly valuable when you can do it.
Zapier for Sounds [00:45:00]
Shaan: Okay, last one. Have I talked about this before?
Sam: You’ve mentioned it. You had a year-and-a-half embargo on it.
Shaan: My friend Samir had this idea. He was going to do it but then found a faster-growing startup and joined as an exec instead. I held the embargo and now I’m pretty confident he’s not doing it.
Here’s the idea: every company has events they celebrate. For The Hustle, it might be getting a new email subscriber, or a new advertiser, or a Trends subscription sale. There’s usually a gong in the office. You make a sale, you walk to the gong, you hit it, and everyone knows.
What if there was just a sound — any service you have, whether it’s Stripe, your email list, your bank account, anything — and whenever the good thing happens, it plays a sound on your phone or your Sonos speakers?
Sam: That’s actually kind of great.
Shaan: And it gets more sophisticated, because you can’t just have every event make a sound forever — it gets too frequent. You need rules: alert me when we hit 100 new subscribers today. Not every single one. So there’s nothing out there that lets you set those rules.
Simple company, a few million dollars in revenue maybe. But maybe it’s more like Zapier — maybe this is a bigger problem than it seems. Celebrations as a service.
Sam: Here’s how I think about it: you look at the macro. All companies want to celebrate wins. All companies know celebrating wins is good for morale. So it’s plausible this can work. How big? I don’t know. But it can definitely work at some scale.
Shaan: Most things that end up quite big started with humble-looking ambition. Facebook was just a college network for Harvard, then for all colleges — Zuckerberg himself said early on, maybe it’ll just stay a cool college thing. Now he’s building internet infrastructure in Africa.
Stake Rent: Rewards for Renters [00:52:00]
Sam: All right, you want to do one more?
Shaan: Hit me.
Sam: Go to Stake.rent.
Shaan: Cash back for rentals?
Sam: Yes. So the guy who started this — I don’t even know his name — he created the rewards program for Amex and a couple of airlines. He knows loyalty programs. And he’s applying that to rent.
Here’s the insight: if a landlord gives a tenant one month free, that’s 8.3% of annual rent. Instead, what if you gave three to five percent cash back every month the tenant pays on time? That’s compelling. Maybe $20 a month cash back. Tenants feel good about it. Landlords get better on-time payment rates. You can go to landlords and say: I’ll lower your late payment rate by X%, and here’s the data to prove it.
Shaan: And it builds a habit. Once a tenant is getting $20 back a month, they’re not going to move — the new place doesn’t have this.
Sam: The thing I like about it: the founder has no real estate experience, but he has deep experience with human behavior and loyalty psychology. Applying a proven model from a totally different industry.
First time I heard this, I thought: this seems shockingly obvious. Why isn’t anyone doing this? Part of me said: well, if nobody’s doing it, there’s probably a reason. But the other part said: maybe no one’s done it because they haven’t thought of it this way.
Shaan: Things in this family I’ve seen work: Rhino, which is rent insurance instead of a security deposit. Instead of putting $1,000 down, you pay $5 a month as an insurance policy. And the concept is similar — apply a financial product mechanic to a real estate pain point.
Sam: And then Smile.io — they took the Starbucks loyalty program experience and made it a Shopify app for any e-commerce store. Points, referrals, birthday rewards — all available to any small brand, not just companies that spent millions building it.
That’s the pattern:
- Go look at what big retailers have built custom for themselves.
- Make the white-label version and offer it to everyone else.
The Domino’s / Starbucks / Slice Pattern [01:00:00]
Shaan: I invested in a company called Joe Coffee. They did the same thing Slice did for pizza. Domino’s has the best pizza ordering experience — track your order, see it in the oven, know when it’s out for delivery. Domino’s spent a lot of money building that.
Slice went to every indie pizza shop and gave them an app with that same experience. Now a mom-and-pop pizza place can compete on the ordering experience — not just the quality of the pizza.
Joe Coffee did the same for coffee shops. Starbucks has the slickest mobile ordering experience — you earn stars, you order ahead, you get push notification marketing. Joe Coffee gave any indie coffee shop that exact experience in a white-label app.
Sam: And in my D2C business I wish more of these things had existed. I’d rather pay a software fee than hire an engineer to build it.
Shaan: Here’s the pattern recognition: when you see three or four versions of the same model, that’s a blueprint you can follow. Go look at what the top retailers do. Walk around their store. Use their app. Ask: what did they build custom and amazing for themselves? Now make the white-label version for everyone else who’s competing with them.
Another one: the paywall. The New York Times has the best converting paywall in media. They spent enormous amounts optimizing it. Someone should take the New York Times paywall experience — that exact conversion flow — and sell it as New York Times Paywall as a Service to every media company that’s using a crappier version.
Sam: You talked about this once. We do this drop model where we launch new products every week, and it creates a huge weekly sales spike. But it also puts us on a treadmill. New product means new photo shoot, new inventory whether or not we’re sold out of the old stuff. It’s driving sales spikes but also creating costs. Is it a dumb idea? I don’t know.
Shaan: The thing to look for is: what served you in an earlier stage may not serve you now. The weekly drop created cash flow and excitement when you needed it. But once you’re more mature, you might not need the spike, and the treadmill costs more than the spike is worth.
Sam: Right. I wish I could weigh these things against each other, but they speak different languages and operate on different time scales.
Shaan: That’s the episode. Let us know how you liked it. My Twitter is @ShaanVP, Sam’s is @TheSamParr.
Sam: All right. Never looking back.