Sheel Mohnot — fintech VC, co-founder of Thistle (100M revenue food delivery), and veteran domain auction entrepreneur — joins Sam and Shaan to share five actionable business ideas he sees as real opportunities. The conversation weaves through his origin story (iPod Mini headphone hustle in China, living on $1/day in India, meeting the Flexport founder on a train), then dives into each idea: affinity-based retirement communities, a Yelp for professional services, a teeth-cleaning franchise, a hotel pizza franchise, and an AI tools school for adults. The second half covers personal finance hacks, Nvidia/Bitcoin investing, stablecoin thesis, and life philosophy around saying yes, coaching, and negotiation.
Speakers: Sam Parr (host), Shaan Puri (host), Sheel Mohnot (guest, co-founder Better Tomorrow Ventures / Thistle / domain auctions)
Introduction: The Most Interesting Man in Tech [00:00:00]
Sam: All right, we have Sheel here today, who is by my call the most interesting man in tech. That is a big claim, and I’m aware of the power of my words, but I did not stutter.
Sam: Sheel, I think I’ve told you this before, but I think of all people I feel like you live in this beautiful blend — you do things that make you successful, but then you do a lot of things that just seem like a lot of fun. They’re random, and you’re letting life kind of bounce you in whatever direction it’s going to take you, and it’s kind of inspiring.
Sheel: And Sam, I know it’s inspiring for you, because Sam is a perfect square and he just likes to be a perfect square, and he doesn’t know what to do with this crazy blob shape like me.
Sam: Sam, is that right?
Sam: Yeah, I mean, he’s inspiring to me. He just does the silliest stuff. But let’s set the table — Sheel, here’s what I’ll brag on your behalf: you have a $20 million VC fund, you’ve built a business called Thistle to $100 million in revenue, and you’ve built another business that sold domains — I think you’ve sold half a billion dollars in domains. You’ve done all this amazing stuff, but then you do the silliest things. Like you did an online version of The Bachelor, you were in a Justin Bieber music video, you do ridiculous stuff.
Shaan: He got married sponsored by Taco Bell in the metaverse. He had a wedding in the metaverse with Taco Bell somehow.
Sam: I don’t even know what that is.
Sheel: I didn’t know about that. That’s awesome. What was that?
Shaan: Oh, it’s a long story. Yeah, Taco Bell sponsored my wedding. We had a series of events — I figured if you’re going to have a wedding, it’s a great excuse to bring your friends together. And it’s an excuse for all your friends to come together. They’re all going to come. So we had six weddings and nine wedding-related events over the course of a year, one of which was sponsored by Taco Bell because we entered a contest. And my amazing wife let me do this.
Sam: Yeah, makes sense. I don’t even know what to make of all this.
The iPod Mini Headphone Hustle [00:03:30]
Sam: I went back and listened to your old episode — you were probably in the first 20 episodes back in 2019, when I first started and I wanted to have interesting people on. I went back and listened this morning because I forgot all of it. I’m going to repeat a couple of the stories. I actually want to start with maybe the relatable side hustle. Can you talk about one of the early ways you made money — the iPod Mini hustle? I don’t even know if you remember the full story, but can you tell it?
Sheel: Yeah. I was a new college graduate, I was working a job, and they gave me an iPod Mini — which is, the iPod had come out in white, and then the Mini came out in smaller size, available in four colors: blue, yellow, pink, and green. Right after I got it, my headphones got stuck in a bike I was riding and broke. And Apple was not selling those headphones — those iconic headphones that I wanted. So I had this idea: let me make these headphones, and I’ll make them in the colors matching the iPod Mini.
Sheel: So I went to China for the first time in my life, just to figure this out.
Sam: You went for this reason?
Sheel: I went for this reason. I was working a full-time job. I took a two-week vacation and I was like, let me spend those two weeks in China and figure it out.
Sam: Where in China? China’s a big place. You were just like, I’m going to go. I’ll find a guy. What was the plan?
Sheel: I went to Hong Kong first. I looked up trade shows — there was a big consumer electronics trade show. I was like, I’m just going to go to this trade show and figure it out. I hadn’t booked anything else. So I went to this trade show, there were thousands of booths, and I just went around having no idea about anything, going to booths, finding ones that made headphones. Their English was very poor. My Chinese is negligible. So it was a lot of: they pull out a calculator, I’m showing them a sketch I had made of what I was looking for, they enter a number — that’s $5 — and I’m like, no, no, that’s 83 cents.
Sheel: Then I actually went and visited their factories in Southern China — Guangzhou and Shenzhen. It was awesome. It was a really fun way for me to get into business.
Sam: How much time passed between your headphone breaking and you being in China?
Sheel: I think it was like a couple of months.
Sam: So you have a job, you decide to go, and you’re funding this off your savings? Did you place a big initial order?
Sheel: The initial order was cheap. It was 10,000 headphones. For me at the time it was a lot of money — it was my first job — but I think it was a total outlay of about $20,000.
Sam: Do you make these headphones — which, by the way, seems like an insane oversight by Apple to not sell the headphones — how are you going to sell 10,000 pairs of headphones? There’s now a playbook for quantitative marketing and all that. At that time, there wasn’t.
Sheel: I started out going after blogs. There were a lot of blogs and I was like, I’ll give you a giveaway for your readers. That was one technique. And then one that was pretty awesome is Facebook had just come out. At that time, Facebook was limited to college campuses, and the way they monetized it was you could set up a flyer — so I could pay a dollar a day to have a sidebar ad at Carnegie Mellon, basically like if I was throwing a party.
Sheel: So what I did was I went back to my high school friends who went to the biggest colleges — University of Michigan, Ohio State, Penn State — those colleges where they had 30 or 40,000 students. I said, give me your Facebook login, I’ll pay you something, and I was able to market to those audiences for $10 a day. You want the biggest audience you can for that $10 a day. So we did in Michigan like the colors of Michigan — blue and yellow stuff like that. It was a cool little business.
Sam: That’s amazing. Facebook used to let you do that — market to your whole campus for ten bucks a day. How much did it end up making?
Sheel: How much money did it make? I want to say net was probably like $80,000.
Dot Collecting: The Philosophy Behind Saying Yes [00:09:00]
Sam: One of the parts of this episode is that you’re pretty spontaneous. But you have a $300 million fund, a $100 million company — pretty epic success — but you also do really random, spur-of-the-moment things. You have a bunch of success but you also do really random things.
Sheel: Yeah. I’ve always chosen the more adventurous path. And I think something I get from my grandfather — my mom’s dad — he was just always bored and always coming up with new ideas. He would read about something in the newspaper and be like, I should start something. When TVs were coming out in India there was only one TV station, and he was like, TVs are going to be big, and he started a TV manufacturing company knowing nothing about it. He set up a pay phone company. He would just read about something and then do it.
Sheel: And as a kid he would actually mail me clips from the newspaper and be like, should we start this company together? I’m 15 years old and he’s sending me ideas. He had some good ones. One I remember — my sister just took this up recently, he passed away many years ago — he had this idea: he looked up Ancestry.com, great business, and he was like, in India people love their ancestry. Why don’t we start one for India?
Sam: Wow. Did anybody do that? Is there an Ancestry for India now?
Sheel: I actually don’t know. It’s probably still a good idea.
Sam: That’s wild.
Shaan: So on the first episode Sheel did, he talked about the domain business. The short version is you were the auctioneer for people who wanted to buy new top-level domains — like .photo, .blog, whatever. So Amazon and Google and rich guys would come and bid, and you’d take 4% of the auction. You sold like $500 million worth of top-level domains. One of the things he talked about — his co-founder was this expert in auction theory and he met him on a train in India.
Sheel: He’s German. In India.
Shaan: That’s ridiculous. What year?
Sheel: I met him in 2006.
Shaan: When Sheel came on the podcast last time, he talked about the Steve Jobs Stanford speech — you can’t connect the dots looking forward, only looking backwards. The famous example is Jobs studying calligraphy, then years later making sure the first Apple computers had beautiful fonts no other computer company cared about. And our friend Darius pointed out: a lot of people hear that and just shrug, like, well, I can’t connect the dots so don’t even try. He said no — what that means is your job is to be a dot collector. The dots will connect later, but you’ve got to be a dot collector.
Shaan: So when I say you’ve chosen the more adventurous path — what are some examples where at the time you didn’t fully realize it, but you followed your curiosity and good things later happened?
Sheel: There’s a lot of that. I love the idea of being a dot collector. I think a lot of it is just saying yes to stuff. I’ll say yes to a lot of crazy ideas people throw at me. Investing — of course you have to be discerning when you’re investing other people’s capital. But for ideas for myself, or if people invite me to speak at a conference in some random country — Latvia, wherever — I’ve been to all these countries people don’t go to just because somebody invited me. And I’ve learned a lot by doing those things.
Sheel: One of the crazier things I did: I lived in India on a dollar a day. I did it for a year. I moved to India when I was 24 years old and lived for one year on around a dollar a day.
Sam: What does a dollar a day get you in India? Is that like a McDonald’s value meal?
Sheel: Yeah, maybe like a McDonald’s value meal per day. What I learned from that year was supremely influential in my life. One: I don’t need a lot of money to be happy. I was so happy during that time. I’d been a management consultant in the United States making a six-figure salary, and I moved to India on a dollar a day. I had a convertible here; in India I had a bicycle, and even the bicycle was a big deal for me to buy. I just had so much fun.
Sheel: There’s this concept in India called jugaad — a Hindi word that means creative problem solving. I really learned a lot of creative problem solving during that year. Just reusing things. The importance of community. Resourcefulness.
Sam: You spent $365 in one year?
Sheel: Yeah. That was it.
Sam: Does that include rent and — what type of program is this?
Sheel: The program no longer exists. It was called Indicorps. It was a volunteer program. I was working for Kiva — a nonprofit microlending institution — and I wanted to live like my borrowers. The people we were lending money to were living on a dollar a day, so I was like, I’m going to do it too.
Sam: So did you just have a midlife crisis at 25? What was the why?
Sheel: The why is kind of silly in hindsight, but I watched a Hindi movie called Rang De Basanti — they’re like, India isn’t just going to change, you have to change it. I was thinking, I grew up in America but I have a lot of affinities to India, I want to change India. I had this lofty ambition, and then I don’t think I accomplished anything for India. I did a lot for myself, but I don’t think I did anything for India.
Sam: That’s defining. I was trying to convince Shaan a few weeks ago to like, don’t spend any money for a week or something, way less significant than what you did, and I got a hard no.
Shaan: I didn’t watch that movie, dude.
Sheel: In hindsight it was stupid — I got super sick, I got typhoid — well, besides that. Overall it was an amazing experience, and actually so many of my close friends today are from that time.
The Flexport Connection [00:18:00]
Shaan: There’s another good dot-collector story for you. Correct me if I’m wrong, but you were one of the first investors in Flexport?
Sheel: Yeah.
Shaan: But it wasn’t a traditional VC move where somebody cold-pitches you and you write a check because you see the future of freight forwarding. You did something — you said yes to something before that. What’s Flexport’s valuation now versus when you invested?
Sheel: I actually don’t know the most recent, but it’s in the several billions. When I invested it was at a $10 million valuation. Something like 10 million to three billion.
Sam: Let’s call it yeah. And you sold some shares?
Sheel: The ones I sold were more than a 100x return.
Sam: Okay, amazing. Go ahead.
Sheel: So Flexport is a digital freight forwarding company. If you have a bunch of stuff in China and need to get it here, there are a bunch of steps — getting it onto a container, onto a boat, from the boat to the port, port to a truck, truck to your warehouse, through customs, all that. And it just made sense to me that this needed to be digital; it’s a real pain if you don’t use something like Flexport.
Sheel: I met Ryan at a party, and we bonded over some really funny things. He’s a hacky guy — he just figures stuff out. He started the company by himself, non-technical, outsourced team originally. We were both buying Uber credits under our names by advertising Google AdWords for our referral codes. At that time I would buy free rides from this guy in India who was probably doing what we were doing.
Sam: Was your guy in India?
Sheel: Yeah, I would buy like $1,000 of Uber credit for like $100 or something.
Sam: So you were effectively doing the same thing. And you bonded over that.
Sheel: We bonded over it, became friends. He’d done some previous businesses in the import-export space, and I was like, whatever you start, I’m going to invest in it. And it obviously turned out great.
Shaan: Isn’t it crazy — you don’t know what Ryan’s worth, but if you have a multi-billion dollar company you’re in the vicinity of hundreds of millions of net worth. And just eight years prior you’re selling Uber credits.
Sheel: That’s a pretty common story. I’ve lived in San Francisco for 12 years now, and there are a bunch of people I met early on who were just hustling, and then eventually started something that became big.
Thistle: The $100M Food Delivery Origin [00:22:30]
Shaan: What’s the story of Thistle? I remember we went out to dinner once many years ago and you were telling me you’d started this local food delivery business. At the time, it looked like a bloodbath — Sprig was going out of business — and you were like, no, we’re approaching it differently. Not the venture-funded way.
Sheel: My roommate in San Francisco and I were just making unhealthy choices — eating the fastest thing possible to get back to work. The idea was: what if there was healthy food in your fridge already? That would be the most convenient and healthy thing you could eat. At that time there were Sprig, Munchery, Spoon Rocket — you could order and in 20 minutes food would show up at your door. We were like, should we invest in these? Should we start one?
Sheel: I ended up driving for Sprig. I signed up as a driver to do due diligence.
Sam: That is so funny.
Sheel: And I identified a bunch of problems with the model. One: they were wasting a ton of food — you cannot predict how much food you need on any given day. Two: drivers are all driving at the same time — lunchtime, dinnertime. Three: routes aren’t optimized, so you’re driving all over the city.
Sheel: So we set out to solve it. The idea was a subscription service. You have to order by Friday for your meals for the following week. It doesn’t work for everyone — like, I might get invited somewhere for dinner — but for people who are more structured, we can give them a meal plan at an affordable price point. Kind of like a private chef. And it’s been great. The business is awesome.
Sam: Is it bootstrapped or did you raise funding?
Sheel: We did ultimately raise funding — a few rounds — but not that much money over time.
Sam: Is it still just in San Francisco? At one point you said it was doing $20 million a year just in San Francisco.
Sheel: It’s now all along the West Coast and the Northeast as well.
Shaan: I see it where I live, right outside New York.
Sheel: You might see Billboards. One fun thing is a lot of celebrities use it, so you’ll see videos of celebrities carrying the Thistle bag, which is kind of cool. Like, this mega-famous person is carrying something I helped create.
Saying Yes vs. Focus: The VC Tension [00:26:00]
Sam: The way you say you live is different from what you probably advise the companies you invest in. You’re saying yes to a variety of things, which — if I wanted to paint this badly — you’re ADD and you can’t focus and you’re missing out on years 8, 9, 10, 20, where all the compounding comes from. How do you balance being focused — which is what every VC tells founders — versus saying yes to speaking in Latvia or going to China to start a headphone company?
Sheel: It’s such a good question. I think the way I think about it is I’m more of a zero-to-one guy than a one-to-100 guy. I’ve started a lot of things and mostly found other people to actually run them over time. Some of the things I started got to exit and were successful. But if you want huge success — multi-billion-dollar companies — you need to be really focused. I would not invest in most of the companies I would start. If I were running a VC fund, these companies aren’t VC-type opportunities.
Idea 1: Affinity-Based Retirement Communities [00:28:00]
Sheel: I just got back from Florida. My parents moved there — to an Indian retirement community called Shantivan. It’s not that well-executed, but the idea is: this guy created a huge plot, put up about a hundred homes, and there’s a community center where they have Indian food, movie nights, stuff like that. It’s really fun for Indian retirees.
Sheel: And I’ve been thinking: there are a lot of retirement communities out there, and most of them are aligned to a single affinity — golf. But there are so many other affinities that should have their own retirement community. People are living longer than they did. They’re still retiring at 65, but they’re living longer and healthier. You could build communities where people do whatever their affinity is, and then stamp it for other affinities over time.
Shaan: I’ve looked at this. They’re good businesses, right? You’re basically taking raw land and doing the math — we’re going to sell 50, 75, or 100 plots, and the numbers get pretty big fast when you’re buying at raw-land prices and selling to residents.
Shaan: One of the things some of them are doing is they blend together different health spans. You can start there when you’re just retired, then as you need assistance there’s an assisted area, then full service. But you don’t have to move far — you’re still in the same community. And as your body goes down that gradient you just move to a different level of service. Super profitable when you do that. The LTV of the customers — imagine, 20 to 30 years in one of these communities. It’s really high.
Shaan: My parents had the same reaction. They were like, that’d be great. I don’t play golf, but if there was a place that had the food we like, with people we get along with, that speak our language, that have the same cultural values — that’s going to exist for every ethnicity. But also not just ethnicity — what are the other things people bond over? What’s the central pillar of their life?
Sheel: For this one, my parents were on a waiting list. They prepaid 100% of the money down and didn’t get the home for five years. These are like a plot of land where you buy a townhouse and pay a monthly fee. You get food — which for Indian people is a really big deal — and they have community events. Movies. Concerts. We actually had one event that was a showcase of all our wedding videos, and then I called in for a Q&A.
Sam: That’s hilarious.
Shaan: This is like the country club model, but for other things. What else is there besides a bougie country club? We have a friend who came on the pod — Craig Fuller — who did this with flying enthusiasts. He bought a plot of land, developed homes on it, pre-sold a bunch, and the center of the property is not a golf course but an airplane hangar. If you own a Cessna you could keep it there and live there, and just walk out to a runway in the morning.
Sheel: That’s so cool. I think you can do this for a bunch of different affinities. My Chinese friends — their parents play a lot of mahjong. You could just build this around every affinity over time.
Sam: These businesses are high-dollar-value — you can make tens of millions of dollars doing this — and there’s a very high likelihood of success. You don’t need a stroke of genius. Fifty people could go do this and they would all succeed. It’s just a matter of execution.
Sheel: And with the silver tsunami — the shortage of space — my parents pre-bought because they couldn’t get into other Indian communities. Prices had increased so much or there was no availability. So they pre-bought into a new one.
Shaan: Is there a status element? Like you have to be a doctor?
Sheel: It actually is a status symbol. I think the community or the social dynamic does work that way.
Sam: How much is a nursing home anyway? I was with a financial advisor like three years ago. He was like, I assume your kids are going to go to school that’s in the 85th percentile of cost, and in 20 years in’s going to be $250,000 a year. And I was baffled. And now I’m realizing some nursing homes are $10,000 to $20,000 a month today.
Shaan: That’s right. There’s a range — $3,000 a month, $8,000 a month, $15,000, $20,000. Nice places can be at $15,000 a month. Some are covered by insurance, some are out of pocket.
Shaan: In different cultures, like you said — in Indian culture there’s an expectation that either the parents move in with you, or you’re going to have your own house and in-home care. My grandparents have their own house and basically have around-the-clock care — someone who lives there and helps them manage day-to-day things. That was what was comfortable for them.
Sheel: I think for all of those options, being in the same place with a community makes sense. Like your grandparents may not need one person full-time, but maybe other people want a fractional one. It’s so much easier if that person lives in the community or can serve many people at once.
Sam: And a bunch of people tried this for post-college twenty-somethings — the After-College Community thing — but this is way better because people are going to be in these for 30-plus years. And they actually have money.
Sheel: Yeah. The twenty-something might spend one or two years in a big city doing this and then graduate out. Crazy churn. I like this model better.
Idea 2: Yelp for Professional Services [00:43:00]
Sheel: Okay, this is the Yelp one. The idea is Yelp for professional services. Why is it so hard to know which insurance brokers are good, which lawyers, which financial planners, which accountants? How do you know who’s good and who’s going to serve your needs? There should be a site for that, and it’s easily monetizable.
Sam: I can give you an update here. Eight or ten months ago I created something called Sam’s List — samslist.co — basically Yelp for accountants. I did it because I needed an accountant, and I actually found one on the website, so it worked. It did $99,000 in revenue and a little bit of profit. We have someone working on it, but we’re adding a financial advisor category.
Sam: Everyone is begging us to add an agency category. I don’t know anything about agencies, so I’m hesitant, but people are constantly posting on Twitter like, hey, can anyone recommend an agency? There should be a site that does all of this. Maybe Sam’s List is it.
Sheel: The market is there.
Sam: It’s hard to pull off though. Here’s why: we had a lot of mom-and-pop accountants on the website. What we did with Milk Road and The Hustle — we had advertisers spending tens or hundreds of thousands, sometimes millions, of dollars a year. But when you’re working with a mom-and-pop accountant, I’m selling packages for like $500. You’re basically like the mob knocking on the door. It becomes a bit of a game. So if you’re going to do it, whoever you pick — the category — has to be where they’re already spending a lot of money, and it’s bigger companies who can write bigger checks. Otherwise you’re going to end up like Yelp.
Shaan: You know the joke in San Francisco? Yelp is where you go to learn how to do sales. They would hire anyone with a pulse and be like, here’s $40K a year and commission, if you hit your On-Target Earnings you’ll make $200K. And then you’d find out you’re going to an ice cream shop asking them for $900. Wasn’t it more like threats than sales?
Sam: People have said Yelp would make reviews go away if you paid. I never found actual evidence of that happening. People have said, okay, if there’s any proof, send it to me — and nobody has.
Shaan: There is with the Better Business Bureau, but not with Yelp, from what I can tell.
Idea 3: Pearly Whites — Teeth Cleaning Franchise [00:51:00]
Sheel: Okay, so this is my wife’s idea. There’s something called Drybar where you can just go get a blowout — kind of like an In-N-Out, 20 minutes and you’re done. My wife feels like she would like to get her teeth cleaned more than twice a year with a dentist. The idea: you go to a place and all they do is clean your teeth. No X-rays, no anything else. In and out in 20 minutes, $100 to $120, something like that. And she would do that every couple months.
Sam: So she likes getting her teeth cleaned.
Sheel: She likes getting her teeth cleaned, and I could see people doing it. Like, I’m going to an event — I’m going to get my hair done, I’m going to get my teeth cleaned.
Shaan: I like the unbundling of the dental checkup. What’s the one part that people would want most or need most often? There might be a market for people who just want this.
Sam: I kind of buy that. But I thought it would be teeth whitening, not cleaning.
Sheel: That’s part of it too, and you probably make more money on the whitening side. But you could standardize it, have a really nice-looking space, and dentists would franchise this. They’d be like, I’m a dentist, I can open one of these. You need a dental hygienist, and in some states you need a dentist present — they don’t have to be doing the work, they just have to be there.
Sam: I went to my dentist and there was this one sign that stood out — everything else looked like a typical dentist office, and then this one sign looked really nice. It was basically advertising something like what you’re describing: 20-minute teeth whitening for like $85. I was like, what is this? Is this yours? And he said, actually yeah — there’s this company that made this service and provides marketing and a name, and we just get incremental revenue from upselling it.
Shaan: It’s basically the Hunt Brothers Pizza model. They did this for gas stations — here’s a pizza shop inside your gas station. Somebody is doing this for dental offices, putting in a teeth-whitening upsell program. It works because the dentist offers like a thousand services, but if you’re just sitting there trapped in the chair, strapped in, the first thing you see in front of you — before-and-after photo — you’re like, yeah, add that on.
Idea 4: Pizza alla Luna — Hotel Pizza Franchise [00:56:30]
Shaan: Speaking of Hunt Brothers — another idea. One of my best friends is doing this and I’ve invested. It’s called Pizza alla Luna. The idea is: people who go to mid-range hotels order pizza constantly. Domino’s is always coming in. So the idea: what if we gave the hotel the ability to sell a high-quality pizza? Originally it was, we’ll give you the oven and the pizza — hand-tossed, made in Italy, actually shipped from Italy, tastes amazing. A lot of hotels now use Pizza alla Luna. We have table tents, all that stuff.
Sam: This is a great idea. It’s just Hunt Brothers but for hotels, and Italian. Is it working?
Shaan: It’s working. Still fairly early but doing really well. My friend is on a plane to Italy all the time. He wanted to make sure it was super high quality, something hotels felt proud to offer.
Sam: Why Italy specifically? Would my taste buds know the difference between Kentucky and Italy?
Shaan: He says you would. And it’s not cheap pizza — Italy knows how to do it. What you’re probably thinking is, isn’t it expensive to bring it over here? It’s actually not that much — it’s kind of worth it. The pizza is actually made near Naples, which is where pizza comes from.
Sam: My dad saw a sign that just said “hand-tossed pizza” with a guy in the window tossing, and he wouldn’t shut up about the hand-tossed pizza for an entire year. These things just work.
Shaan: If it says “world’s greatest cup of coffee,” I buy it every single time.
Sam: You guys know the Grey Goose story? So the guy who started Grey Goose — he brought Jagermeister to the US and made it popular first. He was part of a family alcohol business, his wife’s parents’ business, and they get in a fight, kick him out. He’s out one night and he sees a group of German friends sipping this weird cough-syrup-looking thing, and it was Jagermeister — an after-dinner drink. He figures it out, decides he’s going to become the US importer.
Sam: But to make it popular, he created the Jager bomb and got the Jagerettes — the girls who would go around bars pouring it down college kids’ throats. He made it the party drink. Jager becomes this huge drink, he’s successful. Now he’s in his 70s and he wants to start a vodka company.
Sam: He says, I want to do two things differently. First, where are we sourcing the vodka? They say Moscow, and he says, no — go to France and find me vodka. They say there’s no vodka in France. He says, go to France and find me vodka, because if I tell people this is French vodka, it makes that Russian vodka look like crap. They say, but what if it’s not better? He says, I said it’s French vodka — that means it’s better.
Sam: Then he tells another group: go to the bar right now and buy the most expensive vodka there is. Bring all the bottles. They line them all up. He’s like, what’s the most expensive? Absolut. Cool. We’re going to be 30% more expensive than whatever the most expensive one is. Their bottle’s fat? We’re going to be tall. And then he commissioned somebody to make a frosted glass bottle. Frosted glass, tall — looks expensive as hell.
Sam: And it was so tall it wouldn’t even fit on the shelves, so you had to put it on the top shelf. It had to become “top shelf vodka” by default because it was too tall to go anywhere else.
Shaan: That’s hilarious.
Sheel: It’s basically a commodity — it’s all pretty much the same. Hard for people to distinguish. I have a friend who started a vodka brand and the bottle cost more than the vodka.
Shaan: Alcohol is a tough business though — the regulatory environment, different state by state.
Idea 5: AI Tools School for Adults [01:07:00]
Sheel: Something I want in my life is a school for AI tools. Maybe you could franchise it. But right now I would pay a few hundred bucks to go to a class — half a day — just to become a better iPhone photographer. Show me how to edit things, how to make funny things on the internet, memes, whatever. Same for video. And I think the same is true for many other products you can use with AI or software. A software school, in person, like a Kum Ba Ya but for other useful tools in your life.
Sam: For adults or for kids?
Sheel: Start with adults. Then also kids.
Shaan: Sheel was telling me before this — he’s like, I’m trying to hire someone to teach me video editing and AI. And two things: one, Sheel actually hired an AI tutor, which is pretty amazing. And two, Shaan, you went on this big rant a month ago about what the world wants, what you’re good at, what you’re passionate about — and creating like an AI Kum Ba Ya university is quite aligned.
Shaan: Yeah. First, I did get an AI tutor, mostly because I’ve realized coaches are an absolute life hack once you get some money. It’s a luxury that doesn’t actually cost that much but adds a lot of value. So now anytime I want to do something, my first stop is: who’s a coach I can hire to speed up my learning curve?
Shaan: With the AI tutor — I just tweeted it out. I was like, hey, I’m willing to pay $500 an hour for somebody to sit with me for 90 minutes every Wednesday. I want you to tell me what’s going on in AI, but also be hands-on keyboard with me so I actually learn how to do it. And it’s been kind of amazing, honestly.
Sam: You’re still doing it?
Shaan: We’re still doing it, though it shifted — other friends wanted to join, so now it’s a group thing. But just in general, I’m comically all-in on the idea of getting a coach for everything. Whatever I’m doing, I’m going to keep doing it until it doesn’t work. And it’s worked at everything.
Sam: We hired an organizational coach to come teach us how to organize a closet. I am so on board. Our organizer comes in all the time. Last time she was here, she mentioned that a client from San Francisco is flying her out to organize their new place in Switzerland. She’s got this thing going — people under her, traveling internationally.
Sheel: Is your house just incredible now?
Sam: My wife would say it’s fine. I have a friend who just bought a home — 8,000 square feet — they paid a service $25,000 to map it all out before they moved in. Buy the storage supplies, come up with the strategy, put the labels. $25K.
Sheel: That’s a lot.
Sam: It’s a lot. I don’t know how much we paid total because if I saw it, it would make me crazy. But the kitchen alone was a couple thousand.
Sheel: Do you have the Indian frugality gene, or are you an okay spender?
Shaan: I’m not a good spender. My lifestyle hasn’t changed even as my net worth has increased quite dramatically over the past decade. I’m always looking for a deal. I check Slickdeals first. I’ve got the credit card points thing down — like all this stuff that shouldn’t matter. But for me it’s kind of a game and I love it.
Credit Card Stacking and Financial Hacks [01:14:30]
Sam: Give us a quick credit card tip. What’s your credit card stack?
Sheel: Okay. I use the US Bank Smartly card — it’s 4% on everything. If you just want a single card, that’s the one. US Bank Smartly.
Sam: 4% on everything?
Sheel: Yeah. I use it on my taxes. I pay 1.82% to the government to use my credit card, and I get 4% back from US Bank. So I’m getting about 2% back on my taxes. I could use it for Facebook ad spend — anything.
Sam: Is there a limit?
Sheel: Just your credit limit. It’s called US Bank Smartly. You have to have $100,000 with US Bank, but what I did is I just have a brokerage account with a single stock, and that’s my $100,000 with US Bank. It’s a great deal — they’re losing money on me for sure.
Sam: On one hand I’m like, this is sick, I have to do this. On the other hand I went through a lot of hoops to get 2.6% from Bank of America.
Sheel: This is way better. Way better.
Sam: I also saw you tweet about Robinhood giving like 4% interest or something.
Sheel: Robinhood has a card that gives 3% cash back on everything. Right now they have a promo — 4% or 5% if you put $25,000 into a Robinhood brokerage.
Sam: If you’re a big company spending a lot on Facebook ads, couldn’t the difference between 0% and 4% have a meaningful impact on your margin?
Sheel: Absolutely. If you’re buying Facebook ads at scale — could be really massive.
Sam: Even just on your taxes getting 2% back is many thousands of dollars. That’s like free money.
Sheel: I know a guy — David Hower, he sold Grasshopper for I think $125 million. He’s famously frugal. He convinced American Express to let him pay his tax bill with Amex. On a $100 million sale, that’s probably $36 to $40 million in taxes. And he was like, for the next 30 years I ball out on flying and don’t have to pay for a thing.
Sam: One thing I don’t want to do is accumulate miles. I already have more than I need. People say you’re getting 5% because miles are worth 2.3 cents each — but you’re flying at a random time on a business class flight that isn’t the flight you want to take. Just give me cash back, and I’ll buy my own ticket. Also, miles inflate at some insane rate, and you’re never going to use 100% of your points, so you have to discount back off that.
Sheel: Exactly. For me, cash back is king.
Sam: I know a guy in the Hamptons who’s a two-person company spending $10 million a year on Facebook ads. He had all these miles and was like, hey, book a flight for me and I’ll send you money. I bought four first-class tickets to Europe and probably got a 30% discount. Significant savings.
Sheel: I have another one. Robinhood had this thing — and they continue to have it — where if you move your assets over, they match 1%. So if you have $10 million of assets in stocks somewhere, you move it over and you get $100,000 free money.
Sam: How long does it have to stay there?
Sheel: I think two years. And I’ve been very happy with the service. I just did a transfer from Schwab. Schwab called me — red alert — they’re like, we’ll give you $15,000 right now in your account, you don’t have to do anything, just don’t move your money. And I was like, yeah, but I’m getting a lot more from Robinhood. So I moved it and I’ve been very happy. I use a bunch of their products now. Great margin rate — around 5%.
Personal Portfolio: Nvidia and Bitcoin [01:21:00]
Sam: Are you a stock picker, or just boring index funds?
Sheel: I want to not be a stock picker. I want to be boring index funds. But inevitably I get excited about an idea and I invest in it, and it’s been very good for me. I’ve been fortunate to outperform the market pretty significantly.
Sam: What was your best pick?
Sheel: My biggest position was Nvidia in 2017.
Sam: No way. What was the thesis?
Sheel: I did a lot of research. It was actually more based on crypto than AI — I thought GPUs would drive crypto mining. I was wrong about that; mining moved away from GPUs and into ASICs. But it ended up being right anyway, because of AI.
Sam: Did you keep it the whole time?
Sheel: I kept it the whole time. Haven’t bought any more or sold any. It was my biggest position in 2017. The stock is about 30x from that.
Sam: $5 to $150 something. 30x is wild.
Sheel: I haven’t actually moved it.
Sam: You’re a fintech expert — your fund is fintech focused — what’s your position on crypto? Bitcoin? Altcoins?
Sheel: I don’t talk about this much. But looking at my assets, it’s probably Bitcoin number one, Nvidia number two, and then the house I live in number three.
Sam: No way. Really?
Sheel: Yeah.
Sam: Tell me more. What got you into Bitcoin?
Sheel: I actually have a tweet where I was anti-Bitcoin when it was like 60 cents. I was like, this is never going to work, governments will never allow it. Then I finally bought in around $300. At the time the thesis was: it’s going to be a fast and efficient way to move money. That isn’t what happened at all. So in some ways I was right — but I lost a lot of money by not doing it earlier. As a store of value, the more successful it gets, the more successful it’s going to get. More people are putting money in, so I’ve put money in personally.
Sheel: For my fund, I want to invest in things actual people are going to be able to use and that have real impact. I haven’t found that many use cases. We have made a couple of investments in stablecoins — I think there’s something there.
Sam: Stablecoins. What’s going on there? A stablecoin didn’t — well, a tech company that was doing stablecoins got bought for over a billion by Stripe?
Sheel: Bridge, I think.
Sam: Bridge. Is there anything actually going on here or is this all hot air?
Sheel: I think there’s something real. Transferring money internationally is genuinely hard. There’s something called SWIFT, which is how banks do it — basically a messaging protocol. Stablecoins can make things easier. But I still think at the end of the day, people are overhyping stablecoins, because you still need to on-ramp and off-ramp to get money, and the ramps aren’t that easy.
Sheel: I had this issue: I had a wedding in India and needed to pay a lot of vendors in cash. I tweeted, can someone help me get a lot of cash in India? And the reality is, there’s a reason why it was so difficult — money laundering. And also what my vendors wanted was illegal on their end, because they wanted cash to avoid taxes. The government doesn’t want people to dodge taxes — that’s why it’s hard. Stablecoins don’t fully solve that.
Sheel: What I ended up doing: I convinced my bank, Schwab, to let me withdraw $4,000 per account per day. I opened six bank accounts at Schwab and was able to withdraw $4,000 per account per day from an ATM. I was there for the week before the wedding and basically paid for a lot of it that way.
Sam: You know what the takeaway is? That’s the second time you’ve said something where you went to a major institution and negotiated. When I hear “you went to Schwab” I’m like, is Schwab a person? It’s like getting Google AdWords help by calling Google and saying, hey, I need you to fix this.
Sheel: If you explain your situation, they’ll sometimes help. One thing I do: I know pretty quickly if I’ve got a good agent or a bad agent. If I have a bad one, I hang up and call back. I told them my story, told them what I needed, somebody walked me through the process, and I got it done.
The Art of Negotiation (and Life Skills Worth Teaching) [01:33:00]
Shaan: Speaking of negotiation — you can negotiate at Macy’s. I did this with my wife. She bought a dress at Macy’s — it was like a $400 dress for one of our weddings — and I was like, can you get a better deal? She did. She got like 20% off, just by asking. Saved about $100.
Sam: That’s legit. I’ll do things like — I won’t know if they had a sale recently, but I’ll be like, I think you had a sale recently, can you match that? I actually always prefer to talk to women who work retail. I have way more success — there’s something about it. You do a little fake flirt and it works way better for me. Just talking to a woman and being like, hey, how are you doing today, look, I know this is a little obnoxious, but can I get that sale discount?
Sheel: My friend — when we were in college, we’d go buy stuff for our dorms. His mom was the master at this. While we’re checking out, she’d say to the cashier: give the boys a discount. Give these college boys a discount. And they’d be like, what? For what? And she’d just say: give the boys a discount, they need it. And sure enough, 20, 30, 40% off would just happen. She’d say it like it was already a done deal. Not “do you think it’d be possible?” Just: yeah, throw that in, put the discount on.
Sam: That’s an alpha move. I think it’s something I want my kids to learn — how to ask, how to sell. I wish I had a sales job growing up. Those guys selling Dead Sea Cosmetics at the mall — they’re just coming up to you like, hey, what phone do you have? That skill set is incredible.
Sheel: It’s got to be like a 98% profit margin business too.
Sam: Didn’t your dad sell door to door?
Shaan: Yeah, my dad sold encyclopedias door to door when he first moved here from India. He was very poor in India. To come to the US he had to raise money from his community to pay for his flight. He had to have $300 stamped on his passport; he came with exactly $300 in his pocket. He had a stipend as a graduate student and decided to work as an encyclopedia salesman — Indian guy, thick Indian accent, at that time, in Louisiana, Mississippi, and Alabama — door to door. And he became the best encyclopedia salesman in the country.
Shaan: He made enough money to buy a one-bedroom condo in India, and that’s still the condo my uncle lives in. We still go and stay in it.
Sam: You have a bunch of great tweets about your dad. I feel like I kind of know him. He quoted Robert Mugabe — the dictator of Zimbabwe — at your wedding. He must have gone on like brainy quotes and typed in “quotes on love” and it came back with something by Mugabe, and your dad was like, Robert Mugabe, very very famous for his quips.
Shaan: I think he was famous for something else. And then there’s the video of my dad on a cruise — we went on a family cruise a couple weeks ago. We go to this tasting menu restaurant and my dad shows up with a pizza to the tasting menu restaurant. The people were pretty mad at him. He covered it with a napkin. They were like, sir, we can still see it. He treated it like a baby — put something in front of someone’s eyes and it just doesn’t exist anymore.
Sam: That’s hilarious.
Wrap-Up [01:41:00]
Sam: Thank you for doing this, man. This was fun hanging with you, as it always is. If you want to hear Sheel’s full story, go back and listen to episode 18. I think it’s called something like “the guy who made millions selling wacky domains.” He told his story in order there and it’s a great episode. I went back and re-listened to it this morning — for me to listen to my own voice for a whole hour means the episode is pretty good.
Shaan: Give Sheel a follow on Twitter. He’s a great follow — it’s just the small things. You tweeted a photo of your couch — a 9-by-9-foot couch.
Sheel: I love my couch. My wife hates it. It’s modular so you can turn it into other things, but it’s basically this giant square. When we have people over it’s so fun. You kind of have to hop on like a small child because your feet won’t touch the ground if you’re sitting on it — you just crawl around.
Sam: I’m somehow convinced that’s the right decision. Thanks for doing this, man. You’re the best. We appreciate you.
Sheel: All right, that’s it.