The boring-business filter

Be the public face of car-wash investing (the next storage/strip-mall guy)

Sam pitches picking a boring asset class nobody is loud about yet and becoming its Twitter personality. His specific suggestion: car washes, pointing to carwashadvisory.com listings showing surprisingly high EBITDA and prices, ripe for someone to tweet about constantly and attract investors.

“I think because this is so interesting, I think that there's a world where someone could get into this business and start tweeting about it constantly and just tweet publicly.”

Steal thisPick a boring, data-poor asset class, document deals publicly on Twitter, and let investors come to you.

ESRI: a family-owned mapping firm doing $1B+ a year, no outside money

Sam describes ESRI, a geographic-information-system software company started in the 1960s, still 100% owned by one man and his brother with no debt and no outside funding, doing over a billion dollars a year in subscription revenue.

“It's 100% owned by this one guy and his brother. So 100% owned by the same family. No debt. They've never taken any outside funding. You can't find anything about it. It does over a billion dollars a year in subscription revenue.”

Sam's Type: 1800s-founded, physical product, Midwest, family-named, profitable

Shaan articulates Sam's business 'type' — companies started in the 1800s with a tangible physical product, founded in the Midwest or heartland, named after a family (Rockefeller, Schindler, Otis), and absurdly profitable. Sam optimizes for durability and freedom; Shaan optimizes for excitement.

“Basically, Sam's type on companies. Did you start in the 1800s? In some way? Did you, um, did you have a physical product that you could, that you could touch and feel? Were you started in the Midwest or some, some part of America? You know, are you named after a family like Rockefeller or Schindler or Otis or, or something like that? Um, let's see, what else, what else is it? You know, are you absurdly profitable?”

You don't need to be Elon — buy a poorly-run boring business and fix it

Wilkinson's takeaway from Lemann: skip the urge to invent something revolutionary. Take a traditional, poorly-run business — ideally one that's low-risk, growing, and succeeding despite bad management — and simply run it better.

“you don't need to do something innovative and crazy, right? You don't need to be the next Elon Musk or start some crazy technology. You can just choose a traditional business that's very poorly run. And run it better. And I, you know, even better if it's a business that's low risk growing and kind of successful despite bad management or, you know, bloated cost structure or something.”

Steal thisSkip inventing the next big thing: acquire a boring, poorly-managed but growing business and create value just by running it better.

The uncle who wound down a $2-3M-profit plumbing business he could have sold

Codie's Uncle Eb, a former sharecropper, had a $5M plumbing business throwing off $2-3M in profit but didn't know M&A existed, so at retirement he just let everyone go and wound it down instead of selling. That waste sparked Codie's micro-PE thesis: apply private equity to sub-$3M businesses.

“We Started it because my Uncle Eb, he had a $5 million business. Let me make sure I get the numbers right. That was doing about $2 to $3 million in profit. And he was old, you know, '70s-ish. And he was a sharecropper. He grew up in a sharecropping family, didn't know anything about the business world. And when he came to retire, he didn't know anything about M&A. So instead of selling the company, he basically just wound it down.”

The boomer business handoff: buy steady $5-15M businesses at reasonable multiples

Shaan describes the generational shift where boomers are aging out of profitable, steady businesses their kids don't want to run, creating a wave of $5-15M/year profitable companies available to buy at reasonable multiples.

“And it just seems like there's this huge generational shift of people who are aging out of their business and need to hand it off. The kids don't want to take it over necessarily, or, or aren't able to, or whatever. And so basically the boomers handing over businesses, there's just like all these businesses that are beautiful $5, $15 million a year profitable, super steady book of business. Um, and you can, you could buy these out at like super reasonable multiples.”

Steal thisHunt for retiring boomer owners of steady, profitable businesses whose kids won't take over, and buy at low multiples.

SpyGuy does $3M+ top-line, ~$1M profit a year

Shaan estimates the niche spy-gear store SpyGuy.com is doing over $3 million in top-line revenue with roughly $1 million in profit annually, mostly from reselling other people's gadgets.

“I thought this was awesome because it's a 7-figure store. I think he's doing over $3 million top-line revenue now, probably about $1 million of profit a year.”

WinRed: a 2-year-old company quietly making millions off political fundraising

Sam describes WinRed.com, a roughly two-year-old payments platform behind aggressive conservative fundraising emails (matching-donation pitches from Trump and Breitbart). It takes a fee on every transaction and has processed billions in political donations.

“And I looked at the service that was, uh, do it like the service that was promoting it had like amazing copywriting. I was like, what is this? And it's a website called winred.com. It's only 2 or 3 years old. And that short amount of time it's trans, uh, it's, it's collected roughly, or it's done, uh, over, I think a few billion dollars in transactions.”

Buy paper-ledger storage from 65-year-olds, then automate it

Huber's edge: buy mom-and-pop self-storage in small-town America run by 65-year-olds who keep handwritten ledgers and never took a credit card, then automate so it runs without a full-time manager. That boosts net operating income and lets him find better yield where other investors won't go.

“But what we do that's kind of unique is we buy these self-storage facilities that are in small-town America, owned by 65-year-olds who literally keep paper ledgers, handwritten ledgers, and have never accepted a credit card or check. And we come in and we automate the facility, make it so we can run it without a full-time manager. And you boost the net operating income.”

Steal thisAcquire under-automated small-town operators and wrap them in cheap software to lift NOI and resale value.

The less hype a company needs, the more money it makes

Shaan's heuristic: a boring company name and a bare website often signal a business that's quietly crushing it. His friend's reverse-call-center AI launched with a stitched-together Shutterstock video — and Shaan argues needing more hype usually means a more competitive, fragile business.

“And his launch video was like straight up, go to shutterstock.com, search for the word video and then be like, doctor, thumbs up, happy, call. And he just stitched those together. And like, I was like, dude, if this can be your launch video, your company is gonna make so much money because the more hype you need, the more competitive and ruthless your industry probably is and the more fragile your business probably is.”

Steal thisTreat the amount of hype/branding a business needs as an inverse signal of how durable and profitable it actually is.

The Indian tycoon who got mega-rich selling the color blue

Shaan recounts visiting a fabulously wealthy man in India (cricket field backyard, servants with servants) whose fortune came from petrochemicals — specifically being the largest producer of the chemical dye that makes things blue, even envying 'that bastard' in Africa who owned yellow.

“And he's like, "Blue, like the color, like the dye you need to make anything blue. Yeah, like my company is the largest producer of that petrochemical dye that you need, the chemical dye." And I was like, "What the hell?" And he's like, "Yeah, so like, you know, if you see a blue car, because they bought my dye, that's how they got the blue car." And I was like, "Holy shit." And he's like, "Yeah, there's a guy in Africa, he's got yellow, and that bastard, like I wanna get yellow."”

Build the layer that abstracts away the lowest-NPS experiences

Shaan's heuristic for boring-space opportunities: find the experiences that would get a negative-5-star Yelp review — DMV, visa offices, airport security pre-CLEAR — and build the alternative or the layer on top that removes all the pain.

“Like going to the DMV, going to the visa immigration office, uh, you know, like, you know, the one like this would be— would have been going through airport security before CLEAR. Um, so if you just go and you say, what is the— what's the absolute worst? What would get like a negative 5-star review on Yelp? And then you go and you like build the alternative or build the like layer on top that like abstracts away all the pain, um, that's like a pretty valuable thing if you're willing to go into that boring space.”

Steal thisList the lowest-NPS, most hated experiences and build the layer that abstracts away the pain.

SHRM: a trade association doing $150M/year on subscriptions

Sam holds up the Society for Human Resource Management as the model trade-association business: a simple membership product with huge recurring revenue.

“So it has 350,000 members of this human resource management company and makes $150 million a year in subscription revenue. And it's beautiful.”

WeatherTech: $400M in sales, $100M profit on car floor mats

Sam marvels that WeatherTech made car floor mats sexy with high quality, premium pricing and outdoorsman branding, building a hugely profitable business on a mundane product.

“But it is high quality and it feels like they branded it like an outdoorsman thing. $400 million in sales, $100 million a year in profit.”

Billion-dollar businesses hidden in plain sight

Shaan's takeaway from the Thule example: products you see constantly but never think about (like car roof racks) can mask huge, overlooked companies. Because you're not a buyer, you never ask who makes it or what it's worth.

“the same thing, it's the hidden in plain sight. I see these on cars all the time. I never even once thought to myself, because I'm not buying it, right? Like, who makes these? How much do they cost? How much is that company worth, right? But like, boom, billion-dollar company hidden in plain sight. Freaking roof racks of cars.”

Steal thisAudit products you see daily but never buy, then look up who makes them and how big that company really is.

Study old, boring incumbents to see proven demand

Sam's repeatable move: look up dated, unsexy operators like KOA campgrounds or Boy Scouts to confirm real demand exists, then build a modern version that adds features and prioritizes revenue and profit.

“what I love doing is I love looking at these older things, uh, like KOA, like Boy Scouts, and it's like, show me the demand. And that kind of gives me an idea. And then if you just like add add-ons and operate it in a in a way where you prioritize revenue and profit, then things get super interesting.”

Steal thisFind a decades-old incumbent in your space to prove demand, then rebuild it profit-first with modern add-ons.

Be the credible authority for a niche the incumbents ignore

Sam pitches selling research about emerging niches (like 2020 crypto/Bitcoin) to financial institutions and consulting firms for thousands of dollars per report, reaching single-digit millions in revenue fast before adding a conference, since legacy brands like Gartner won't cover it for years.

“And I think you could sell that for thousands of dollars to all the consulting firms, all the financial institutions, and you could get to single-digit millions in revenue pretty quickly there. Then you add a conference, then you kind of go from there. And so I think that's one where I would go towards a niche that the existing big brands don't cover because it's not their area of expertise, and also it's small today.”

Steal thisBecome the trusted research stamp in an emerging niche the incumbents are too slow to cover.

Buy boring: Tiny acquires simple, profitable, durable internet businesses

Andrew Wilkinson describes Tiny's thesis: a long-term holding company that buys majority stakes in profitable, simple, often boring internet businesses from bootstrapped founders. He deliberately avoids sexy categories like drones, AI, and VR in favor of predictable cash flow.

“So we go out and we find profitable, simple, often boring internet businesses, and we acquire majority stakes and we take over ownership. And we usually buy from founders. Often they're bootstrapped., and usually the businesses have been around for, you know, 5, 10 years. These are longer-term things, and we don't go for sexy stuff. We're not doing drones and AI and VR and all that kind of stuff. We look for businesses that are simple and predictable and boring.”

Steal thisHunt for simple, boring, cash-flowing internet businesses that have already survived 5-10 years instead of chasing sexy categories.

Boring beats sexy: TechCrunch hype invites competition

Kukoff makes the case for boring businesses: the more press and TechCrunch attention you get, the more competitors fight for your market. Staying under the radar, like Veeva, lets you dominate a huge market quietly.

“And by the way, boring is good. The more like sexy, big, like press and TechCrunch stuff you get, the more competition you have for that slice of your market. If you are boring, under the radar, like Veeva, great example, right? No one knows who they are. Multibillion-dollar company that only raised one round of funding in a huge, like, big whale hunting market.”

Steal thisPick a boring, under-the-radar market so you face less hype-driven competition.

GovDocs: labor-law posters to $20M+ government MailChimp

Shaan tells how a Minnesota company started in 1999 selling the legally required labor-law posters every business must buy yearly (~$28, 99% renewal), then spun out GovDelivery, a 'MailChimp for governments' embedded in cities for constituent email/SMS, now a $20M+/year subscription business.

“And then they actually have this other business they spun out called GovDelivery, which I thought was kind of interesting. So it's government tech. So basically it's MailChimp for governments. So every state, city, county, whatever, has a bunch of constituents on an email list that they— or SMS or physical mail— that they need to contact to communicate basic rules, information, road closures, whatever it may be. And so these guys are like, oh yeah, we'll be the tech for you to power that system. And now they're just embedded in like all these cities. They'll never get swapped out.”

Paid Kentucky workers 40% above local, 30% above US average

Smith ran the business in Kentucky and paid wages roughly 40% above the Kentucky average and 30% above the US average, with everyone getting a bonus of about a month's salary every profitable year.

“We were in Kentucky and our wages were typically 40% above average in Kentucky and 30% above average in the US. Every year, everybody got a bonus. Everybody got a bonus typically as long as we made a profit. We always made a profit.”