Today, I’m talking with Tom Patterson, founder of Tommy John, the underwear brand that turned a frustrating problem into a 9-figure business.
Tom started the company after getting tired of undershirts constantly coming untucked while working in medical sales. What began as a simple fix turned into one of the biggest direct-to-consumer apparel success stories of the last 15 years.
In this conversation, we break down how Tommy John bootstrapped its way to over $100M in revenue before taking meaningful outside capital, why Howard Stern and Kevin Hart became game-changing growth channels, and what founders misunderstand about building premium consumer brands today.
Tom also shares lessons on raising capital, balancing wholesale with direct-to-consumer, building a company with your spouse, and why experience can actually become a disadvantage in fast-changing markets.
Brad Weimert: Today’s guest is Tom Patterson, founder of Tommy John. Tens of millions of pairs of underwear sold, nine-figure brand, profitable since inception. Welcome to Beyond a Million.
Tom Patterson: Thanks for having me. Excited to be here.
Brad Weimert: I am glad that you’re here. Now, you sell a lot of underwear. How often do guys tell you that you make their balls feel really comfortable?
Tom Patterson: Yeah. I mean, if you saw the text messages I get on a daily basis, you probably have a lot of questions, but I’m used to it at this point. But, yeah, I hear it all the time. People show me their underwear all the time, men and women. So, what’s weird to many is just normal to me.
Brad Weimert: I think I actually am guilty of sending you one of those messages a few days ago.
Tom Patterson: Yeah, I’ve gotten a couple from you, but it means you’re thinking about the product in a good way.
Brad Weimert: That’s true. Bigger game changer for you, Howard Stern’s 20 million listener shout-out, or Kevin Hart’s equity check?
Tom Patterson: Oh, man. Similar, but different in a lot of ways. I mean, Howard, I think when you look at kind of a brand map, people that we want to really be ambassadors of the brand, Howard probably would’ve been up there, but not in the top 10. But the story there is we sent underwear to 30 or 40 different influencers at the time, TV host, radio host, celebrities, athletes, and Howard ended up getting a pair, talked about it live on air about how it changed his life. He couldn’t picture a day without wearing Tommy John after trying it on, and we had our best day of sales ever. At the time, it was $40,000, and a month later, he talked about it again. I think we did around $52,000 in one day.
And then shortly after that, Sirius Radio called and said, “Hey, Tom, would you be interested in advertising in the Howard Stern Show?” And I was thinking to myself, I’m like, “Why? We’re getting free advertisements every month,” but I said, “Send us a proposal.” And at the time, it was $60,000 for about a month test, one ad a week, one one-minute read. And that was about four or five months of our total marketing budget. So, we kind of put all the chips in, and we ended up paying for the whole month of advertising in the first 36 hours.
Brad Weimert: Damn.
Tom Patterson: We went through six months of inventory in six weeks. That one-minute ad was like a three-minute evangelism of the brand. You couldn’t have had an agency write a better ad. But I think what it really came down to, Brad, is he loved the brand, he loved the product first and foremost. It solved a problem for him. And his listeners, whatever he says, good and bad, they trust with a high degree of loyalty.
Brad Weimert: Let’s timestamp this. What year was this?
Tom Patterson: That was 2014.
Brad Weimert: So, he also was the first person in mainstream media to speak his mind freely. Full stop.
Tom Patterson: Yeah.
Brad Weimert: He said the most inappropriate sh*t ever on radio from day one. And I think that when you’re selling underwear, that probably is a very positive thing to be able to do.
Tom Patterson: For sure. He verbalized what a lot of people were thinking.
Brad Weimert: Yeah, exactly.
Tom Patterson: Right? And I think the way he spoke about the product just resonated. But I think any great marketer can sell a product once, but only a great product can sell itself twice. So, yeah, Howard could help us sell a product once, but it was really the repeat behavior we found from his listeners that really created this litmus test, where we sent it out to other people on Sirius radio, like Colin Cowherd and Mike & Mike. And we would always make sure they liked the product first before we advertise, because we wanted it to be an authentic partnership. So, back in 2014, no one was advertising a lot of products on the radio, let alone underwear.
But we kind of pioneered podcast and Sirius Radio marketing underwear through your ears instead of your eyes looking at a box with a guy with a shirt off in their department stores. We kind of invented a new way to market the category, positioning the problems that we solved through fabric fit and function, for lack of better words.
Brad Weimert: Most entrepreneurs today that are like, “Hmm, what should I do? What industry should I get into? What products should I make?” don’t think, “You know what I should do? Sell underwear.” So, let’s back out to the beginning of the journey here. You’re hundreds of millions of dollars sold in this, a billion-plus dollars sold a product at this point, but you started with an undershirt out of your apartment. The initial, I think you had a 200 batch run initially. What was that story, and what gave you the confidence to actually run with that product and say, “This is actually going to work for me”?
Tom Patterson: So, back in 2007, there was this TV show called The Big Idea with Donny Deutsch. He had a lot of entrepreneurs come on who invented products, and most of them had thought, “I don’t like the way this works. I want to invent a new way, solve a problem that’s really unique to me and authentic to me. So, they would either solve their own problem or look at a product. I think maybe there’s a better way to make something that’s already existing on the market.” So, I’d watch it every couple of days. Next morning I’d wake up thinking, what’s my problem I can solve? Is it a cell phone cover? Is it magnetic collar stays? Because I wear a dress shirt and suit every day.
And one day I got out of my car at a hospital in San Diego, and my undershirt was bunched up to here, but my dress shirt was tucked in, and you kind of like pull the dress shirt down, and you pull the undershirt down through your pockets. And I’m like, “There’s got to be a better way to make a men’s undershirt.” So, I went to some department stores in San Diego, and what I found is most brands pin the shirts behind the model. So, the shirt looks fitted on the box, but when you get it out, it actually is form-fitting for a UPS box. It’s the same width at the bottom as it is at the chest. They shrink one to three inches in length. They yellow quickly. And I thought, “Why doesn’t anyone make an undershirt that solves these problems?”
So, I went to the garment district in downtown Los Angeles, bought some fabric, took that fabric to the dry cleaners with a sketch I drew with my limited art skills, and I had 10 prototypes made. It’s $100. I figured it took five hours out of my time. The worst thing that’s going to happen is I lose money. And the first undershirt she created, it was really long, but it had a V-shaped design, stayed tucked in, it didn’t stretch, it didn’t yellow, and kind of solved all of my problems. And anyway, long story short, I made more, I sent them out to friends, type of people that would say, “Tom, dude, what are you doing here?” or, “Hey, this is a great idea. If you make more, I’ll buy them.” And that’s what happened. They all called back and said, “If you ever make more of these, I’ll buy them from you.”
So, ended up going back to Los Angeles, found someone to produce the first 200 undershirts, built a two-page PayPal checkout website before Shopify. I did the modeling on a rooftop in San Diego with a really elementary photographer friend of mine. But I think not having an experience or having a formula to follow was kind of an advantage at that time because I asked a lot of questions just because I didn’t know. So, we kind of thought of a new way to enter the category, which was really through the stay-tucked undershirt, and it kind of led to underwear and pajamas after that.
Brad Weimert: So, you patented the stay-tuck design, and it sounds like, and correct me if any of this is wrong, this is my research from the internet, which can be wrong, but you submitted a patent for the stay-tuck shirt in 2008, but it didn’t get granted until 2015. Is that right?
Tom Patterson: Yep.
Brad Weimert: How did you think a patent would help, and how did it end up actually helping if it did?
Tom Patterson: Yeah. I mean, we have a utility patent because our patent makes a claim that our undershirt stays tucked in through movement, which no one had done up until that point. There’s also that eight-year period where you can just wait and wait and wait. But what we did during that seven-year period is we wanted to go out and build a brand, right? Build a brand around the product, sell the features and benefits that the undershirt has. So, it has certain protections, I think, that prevent competitors from entering the category with the same measurements and components that we have. But at the end of the day, you still need to continue to grow during that time, where the patent was in a pending mode.
So, we never really built the business to be dependent on that. It’s nice to have, and we certainly enforce it when we need to, but it’s been a great advantage for us, and I think people have now looked to us as when we enter a category or a product, it’s, “What’s the utility?” “Oh, underwear that doesn’t ride up your legs, socks that never fall down, T-shirts that are preshrunk so they’re unshrinkable.” So, we always try to have a smart utility around the mode of our brand. Then we try to have fun with it, right? We have a stay-tuck guarantee, the end to EFG, which means excess fabric gut, which when your undershirt bunches up, a no-wedgie guarantee with our underwear because it doesn’t ride up your legs because we have fabric that stretches in 16 different directions.
So, there’s a lot of intent, I think, that goes into it, but there’s a lot of details that I think the end consumer doesn’t really get, other than like, “That was awesome,” or like, “These feel great,” but there’s a reason why it feels better than your other products you’ve worn from other brands.
Brad Weimert: Yeah. Well, I kind of think about in today’s world, a lot of things have been democratized through mass manufacturing, distribution, drop shipping locations. Like a lot of things got centralized through other companies that make it easier to just spin something up real quick. And so, when I think about something like this, look into something like a patent, I’m looking for, was it a moat? Clearly, it’s intended to be a moat when you file a patent, and then you’ve got the actual moat, but then you’ve got this big gap where maybe there’s a branding opportunity or marketing opportunity through it. But clearly in the first eight years, somebody else could have done something like it. Did you get the benefit before the patent got granted through marketing, or do you see the benefit in retrospect?
Tom Patterson: I would say both. We certainly had trademark pending, patent pending on our packaging, on our website, on our copy, but it was more so just getting it out into the market. And, at the time, I don’t think our competitors realized how big that business had become for us. But undershirts, I would say it’s 75% of men wear an undershirt, but not daily, right? For weddings, for funerals, for getting dressed up. You’re not wearing one, are you?
Brad Weimert: Nope.
Tom Patterson: Okay. Some guys don’t need them. They don’t sweat through. I’m pretty sure you’re wearing underwear.
Brad Weimert: No.
Tom Patterson: Maybe not. Okay. Well…
Brad Weimert: I’m in Texas. I feel like when I moved to Texas, I was like, “Listen.” But your hypothesis, I think, is generally right, where underwear everybody’s wearing it almost all the time.
Tom Patterson: Yeah. That’s why it’s so cold in here. But 99% of men wear underwear. So, underwear is a much bigger TAM, total addressable market, than undershirts. And I think we quickly realized is you need to have both to be in the category. Underwear is a much bigger business for us than undershirts. Undershirts also last longer. They’re not worn as tough, I guess, so to say, as underwear is. So, underwear is a more predictable model where undershirts guys will wear until they’re literally holy.
Brad Weimert: Yeah.
Tom Patterson: At the end of the day, because they’re not really seen as much as underwear.
Brad Weimert: That makes sense. Well, to the sort of defensible moat, you also created sort of new fabric and construction techniques that helped define the product. How did you approach that 10 or 15 years ago, and how would your approach be different today in 2026?
Tom Patterson: I think for us, we kind of looked at what are the problems we can solve, not just with fit and function, but also fabric. And our first fabric was this fabric called micromodal. There was other brands that had micromodal at the time. But the problem with micromodal is when you wash and dry it, it would pill, which means you get balls on the surface, and it looks older faster. We worked with a manufacturer in Israel that produces in Egypt that had patented a non-pilling micromodal. So, it looks newer longer, it never pills, still maintains that luxurious soft. It’s our Second Skin line, which I think is what you have.
Brad Weimert: Yes, thank you.
Tom Patterson: And for the listeners that are wondering. But that was our hero product. That is still our biggest business today. But there was a lot of people that said, “Tom, I like the micromodal fabric, but I only wear cotton. I only like natural fabrics.” So, we found a super lightweight Pima cotton with a little bit of stretch for stretch and recovery, so it maintains its shape. It doesn’t ride up your legs. So, we had different alternatives for different fabric preferences, but it dries four to five times faster, and it keeps you three to four times cooler than traditional cotton because of the weaving process that it goes through.
Another example is we have our air underwear for guys who like to travel. It weighs two ounces, and it dries in two hours or less. You go on a trip for two weeks, you can bring two pair of those, wash it and dry in the sink. So, we’ve found these kind of smart utilities for different user benefits in the fabric, and we market it differently. Like, for example, I would go to our manufacturers overseas, and I would wear women’s products, not underwear, but I would wear women’s shirts, because why? Because the fabrics were lighter. They were stretchier and more innovative. We took those female fabrics into the men’s category in ways that really hadn’t been done before. Half the weight, more breathable, stretchier, that kind of fit I think the needs that the modern men were going towards.
So, I think at Tommy John, we like to think we never rest on innovation. It’s like you have to continue to evolve and innovate. What’s interesting to me today is having Claude and ChatGPT. I think you can innovate differently, faster, tinkering to a certain extent with all categories of clothing or consumer goods in general, and I think that’s going to be a really exciting evolution in the next five or 10 years. As brands think about what to launch, they’ll be able to buy their inventory smarter with less risk than just following 100% gut instinct.
Brad Weimert: So, you’re saying the AI implementation today in the apparel section is contingent on, is founded in the research side of it. Was that the hypothesis that you can lean on those tools to learn?
Tom Patterson: Again, I’m not an expert. I think that could be said to a certain extent.
Brad Weimert: You kind of are.
Tom Patterson: Yeah. Well, I think if you’re an expert today, you got to clear your cookies because tomorrow’s different. The speed and velocity of which AI is changing, I think you have to be aware of the bias. I’ve always kind of felt that data helps you minimize making mistakes, but our biggest, most impactful decisions we made at Tommy John, they never would’ve supported those. It was more of the intuition, right? Why Howard Stern? Why Kevin Hart, right? These partnerships that we’ve developed, I wouldn’t say our brand data would have said Howard’s top three. Kevin’s top three. But they ended up being game-changing partnerships for us in a lot of ways.
So, maybe AI can get refined to that point, but then it’s going to be everybody’s using the same thing at the end of the day. So, what’s a separator? I think it’s probably going to come back to just intuition. I don’t know if AI, maybe AI can override that with avatars. We’ll see.
Brad Weimert: We will. And then the other side of that is sort of manufacturing and distribution. So, to me, creating the materials or finding the materials and then getting the distribution seems easier today in 2026 than it was 10 years ago by a lot. What are the keys to defending yourself as a premium brand against all of these knockoffs that have good-feeling materials on TikTok shops?
Tom Patterson: Yeah. I mean, I would say go buy 10 TikTok brands and see how they perform. I think there’s a reason why the Yetis and the Lululemons and the Pelotons of the world have maintained their space because they kind of premiumized what was former commodity products. And I think there’s always going to be demand for, look, I mean, we’re never interested in making the cheapest. I think dollar for dollar you kind of get what you pay for, and your repeat behavior of your consumer cohorts really validate that. But the barrier to entry is much lower today in TikTok and in Instagram. I would also wonder what sort of margins those companies are running on, also. So, when we launched in 2008, we were primarily a wholesale brand.
So, when we went direct-to-consumer, we had a really strong margin profile, which was different than a lot of brands that were digitally native first and then wholesale second. We were wholesale first, digitally native second. Most of our business today is digitally native, direct-to-consumer. We’re still in wholesale, so I think you need to be all places for all consumers. But, yeah, if you buy some product on TikTok, it may be better than what you’re wearing, right? There’s different levels to go from like dog food to filet mignon and everything in between. So, I think we’re not for everybody, but I think once you get into a brand, we have a lot of loyalists, too.
Brad Weimert: Okay. This is the interruption where I’m supposed to take money and let somebody else advertise on the podcast, but I don’t really want to do that, so I’m going to remind you that I also own EasyPayDirect.com. And if you are a business that’s accepting credit cards or needs to, you should understand why we have thousands of people a year come to us off of platforms like Stripe or PayPal, and why they prefer Easy Pay Direct. You can check us out at epd.com/bam. That’s epd.com/bam.
Brad Weimert: Yeah. Well, you said it from the beginning, which was you said it very eloquently, and I’m going to butcher it now, that you can market your way into the first sale, but not the second. The only thing that sells the second sale is the quality of the product.
Tom Patterson: I mean, how many times have we bought something off Instagram or TikTok and you get it, and it’s kind of a letdown, right? I think brands have gotten really good at the marketing and the branding and the data to target the right consumer. And the product sometimes is just like, okay, it’s not great. It’s not terrible. It may be good enough for where you’re at, but I think there’s a certain stage of life where you just want less things, but the things you have, you want them to be nice and trustworthy and dependable and just work. And I think that’s kind of where we meet the intersection of the consumer mindset and products that they’re really preferring at that time.
Brad Weimert: Can you break down the economics of the wholesale versus direct-to-consumer proposition and how the margin works with that?
Tom Patterson: Well, wholesale, obviously, they buy it at anywhere from 50%-60% off suggested retail price. But there’s a lot that goes into that because they have to mark it up to sell it in their store to cover expenses for employees, fulfillment, and everything else. But when you go direct-to-consumer, cut out the middleman, which is a traditional retailer, and you go right to the customer, you have that direct relationship. But I’d say what’s changed in the last five years is duties, tariffs, inflation. Direct-to-consumer’s become a lot more competitive. The algorithms on Meta and Instagram are constantly changing. The arbitrage moments aren’t like what they used to be. All brands are using the same platforms, right?
So, the separator is a little more difficult. I think you just need to be more surgical and, in a lot of ways, not to say it can’t be done. There’s a lot of people at the bottom now.
Brad Weimert: Yeah. I guess what I was trying to wrap my head around was you said that you had a competitive advantage going direct-to-consumer because you were already wholesale. And so, were you saying that you were already able to make a margin wholesale, so by the time you had to go direct-to-consumer, you had a much bigger margin to play with?
Tom Patterson: Yeah. I think a lot of digitally native brands who don’t have wholesale on their future plans create a margin profile around never going into wholesale. Well, when you go into wholesale, you’re going to give up a lot more margin where you really can’t make any money. So, we had a profitable margin profile at wholesale from day one, so we never had to like increase our price drastically to kind of offset that. And I think that’s where a lot of brands got stuck in the last five or 10 years, where they said, “We’re going to give you the consumer a better product for a fair price.” But then what they learned is like it continue to grow or reach their valuation that they raised their last round at. They have to increase distribution. And that’s traditionally through wholesale.
I think we’ve always felt it’s not one channel. It’s wherever the customer is, whether it’s our website, whether it’s wholesale. Wholesale’s a great place for product placement, right? If you’re in a Nordstrom like we are, it gives you validation. It gives you credibility that a lot of TikTok brands don’t have, right? If you see something in Nordstrom, you’re like, “Whoa.” They were obviously vetted by buyers who have been buying for a really long time. There’s a certain customer that knows when they walk into a Nordstrom, usually it’s going to be a quality product that they can stand behind. So, I think we’ve been fortunate to be in great retailers for a long time that I think helps kind of balance everything.
So, yeah, wholesale can be a lower margin channel than direct-to-consumer. I think it depends on how your prices are set up front.
Brad Weimert: Yeah, that’s interesting. I think that you had the whole chain of why you should have a different level of respect or perception of something that’s in Nordstrom’s. I think most people don’t have all those data points or think through it. They just think, “Oh sh*t, this is a real product.” The frequency with which now I’ll buy things on Instagram, somebody’s like, “Where’d you get that?” I’m like, “I got sucked in by an Instagram ad.” And that’s the conversation, right? It’s not about the quality of the product. It’s not about anything else. It’s just I got sucked in by an ad. And that is, I think, in consumer’s minds, very different than somebody that has a retail presence somewhere.
Tom Patterson: Oh, for sure. For sure. And I think too, your advertising is more effective. For example, if you hear a podcast or a CRTV ad and then you walk into a Nordstrom and see the brand, you just have more chances for recall, also, versus relying on the echo chamber of the algorithms we’re in on social media.
Brad Weimert: Which will follow you around for a period of time, then disappear.
Tom Patterson: Yeah.
Brad Weimert: Usually. So, your women’s line is now roughly 30% of your total sales. What convinced you to go all in on bras? You just like boobs?
Tom Patterson: I wouldn’t say it was all in on bras. I think what we learned is we had a really high percentage of our customers who were women buying for the men in their household, their sons, their husbands, their dads, whatever. Women still make up a high percentage of men’s underwear purchases. So, the data really shown, we had the consumer buying, and we felt we could kind of serve a need with innovative fabric fit functionality. So, yeah, the end of booby traps is one of our bra claims. What the gusset, having a cool cotton gusset on the underwear for women, using the same fabric, so there’s a lot of economies of scale to have Second Skin men’s and women’s sharing fabrics.
So, there’s a lot of smart synergies we were able to benefit off of. But you know, we launched women’s after we were 10 years old in 2018. So, the women’s line is eight years old. But what was really interesting is when COVID happened, it really accelerated our women’s business because women were kind of like buying and shopping, buying toilet paper, groceries, whatever, during COVID. And men were kind of like hunkering down, not really buying a lot of things because of the uncertainty in the economy. But they were buying pajamas. They were buying underwear. We had a lot of inventory available, so that the homebody, work-from-home economy really accelerated the growth of our women’s business kind of unexpectedly. So, I would say you could call it luck because we certainly had no crystal ball to that.
Brad Weimert: Yeah. Well, you said something that stuck out to me, which was that the women are buying the men’s clothing most of the time. So, you created a product that spoke to the actual buyer to sell them, which then probably had significant downstream effects to buy their husband’s underwear as well. I had a great friend, rest in peace, John Ruhlin, who had a gifting business, and one of his tenets was to always take care of the spouse. So, if you were targeting somebody or you wanted to, he would say drop a love bomb on a prospective client, the path to that very often was to take care of the family because you knew if you took care of the family, you had a raving fan built into the ecosystem that would fuel the target market and the purchase.
Tom Patterson: Yeah, that’s exactly right. And one thing I didn’t share is when we launched into Neiman Marcus was our first retailer back in 2009, and we did a survey to women at the time, when we found out it was something like 65% of men’s underwear was bought by women, but women only looked for three things when they went to a store. This is kind of pre-Internet 2008. They look for a good-looking guy in the packaging. They look for the brand that their husband or boyfriend’s been wearing because guys don’t really change. They put up with what’s good enough or they look for some like a good-looking guy. Did I say that? Good-looking guy, packaging, or the brand that they’re used to seeing.
So, we found a good-looking guy to be on the packaging, but we did a survey, and we found that the women in the survey, two things stood out. They liked Tiffany’s jewelry for some reason, and almost all of them liked chocolate. At the time, all the packaging and retail stores was black and white. So, we launched our packaging with a chocolate brown and a Tiffany’s blue. Not the Tiffany’s blue because it’s patented, but a version of that. So, our color kind of fired like a diamond on the department store shelves to attract them to a brand that really no one had heard of, right? We weren’t the baseball pitcher. My middle name’s John. People call me Tommy. But that really allowed the product to stand out amongst our competitors.
And then once you got to the box, you could open it up really easily and touch and feel. And once they touched and felt it, that’s what really sold them on it. So, we catered to women buying it from day one in a physical environment like a department store. And then we learned how to market it to women online. And what’s crazy is men only buy underwear for 17 years out of their entire life.
Brad Weimert: Oh, you mean until somebody buys it for them.
Tom Patterson: Yeah, exactly. Exactly.
Brad Weimert: That’s so twisted. That’s not true of me. I’m 45. I’ve been buying it the whole time.
Tom Patterson: Well, zero to 18, mom usually buys it, or dad, if you don’t have a mom. But then, between that time and when you get married, you buy it. And then once you get married or in a partnership, usually the spouse buys it. So, that’s how they get that average of 17 years. So, you’re kind of crazy not to market to the ones who’s making up all the purchasing for the household.
Brad Weimert: I mean, it sounds very logical. It’s also just one of these things that people haven’t figured out or don’t do or are too shortsighted to do.
Tom Patterson: Yeah.
Brad Weimert: Yeah. That’s super interesting to me.
Tom Patterson: That was my love bomb then, right?
Brad Weimert: Yeah. That you gave me.
Tom Patterson: Yeah.
Brad Weimert: Yeah, exactly. You gave me a package of all sorts of stuff. It was crazy. And when I first got it, I got one pair, and I was like, “Oh, that’s amazing. Thank you.” And then like two days later, I got 15, I got all this stuff.
Tom Patterson: Yeah.
Brad Weimert: Which was very, very cool. I appreciate it. Great product. For anybody that hasn’t played with it, you need to go, and like you said, go to a store and touch it or just buy some because I think the brand speaks for itself at this point. Well, I want to talk about the journey, the bootstrapping, raising money. Why and when? I’m sort of endlessly fascinated by the difference between a bootstrapping journey and a funded journey, and the people that crossed the line at some point. So, you waited several years before bringing on money. You were profitable. When you finally brought on money, why not just raise debt? Why did you raise equity to do that? Why wouldn’t you just go get a loan to handle things?
Tom Patterson: Yeah. So, when we launched, I cashed up my 401(k). I used my savings, used credit cards from American Express to Visa and MasterCard to finance a lot of the startup costs. But in our category, like inventory is the big cash constraint, right? So, it was tough because a lot of times, the purchase orders from a department store, we didn’t have the cash to finance the inventory. So, we would have to use a credit facility or they’re called a factor where they take a percentage of the purchase order, hold it, and then when the department store pays, they pay them first. They keep their percentage that they earn 5% to 6%, but it allowed us to get cash upfront from the factor to finance our inventory as we grew.
Brad Weimert: Oh, God.
Tom Patterson: So, yeah, some would say it’s cheaper in the long run to do that. Some would just go, “I need you. I’m going to go raise money and use other people’s money.” So, for the first five years, 2008 through 2013, we used our own money, not other people’s money, to finance the growth, getting creative with factoring. We eventually convinced our factor to finance our online growth because it was more predictable than wholesale growth, which our factoring facility had never done before. And I think that’s where a sales background comes in really well. Not that we’re trying to sell them on something we don’t believe in, but sales comes down to trust and relationship, and conviction. I think we had proven to the factor that we could walk the talk of our inventory planning, so that’s what we did.
And then in 2013, we raised a small venture round between venture and angels of about 1.5 million, and that really went to hiring for direct-to-consumer expertise. Just financing our growth. We were growing from 2.4 to 4.7 to 11 million. For us, that was a big growth.
Brad Weimert: Yeah. It’s a big growth for anybody.
Tom Patterson: And you have to keep up with inventory because we’re a replenishment model, especially for department stores, where they would order every week from us. So, that investment was fruitful because we got the direct-to-consumer expertise that we needed to kind of change our model in 2012-2013, going from wholesale, having a direct relationship with the online customers. So, I think we were really one of the first brands to start marketing underwear, not only a podcast and radio, but direct-to-consumer as a result of that. And then from there, we waited from 2013 to 2021, and we just financed our own growth. We didn’t raise money. We built a hundred-million-dollar-plus business off of 1.5 million in funding.
I think a lot of companies haven’t been able to do that. It just takes patience, 20%, 30% growth, not biting off more than you can chew. But I think, in hindsight, it allowed us to have more control growth. It helped us be more measurable, hiring the right people, maintaining culture, and I think those are a lot of things that can become problems if you grow too fast.
Brad Weimert: So, what I didn’t get an answer to, well, so you alluded to gaining experience or access through the $1.5 million equity raise. I didn’t hear all the details. Did you bring money on from somebody that gave you insights, connections, et cetera?
Tom Patterson: Yeah. I would say it was certainly smart money. It was money where I felt like they could help us bring on and hire the right people for direct-to-consumer marketing, the front and backend development, the things that we needed to do to really grow our direct-to-consumer business, also financing inventory. And it just helped ease some of the growth constraints that we had. Because at the time, the wholesale mindset was very different than the direct-to-consumer mindset. Now everybody’s doing direct-to-consumer. It’s much more common. But back then, it was harder to find the talent. You could argue a little more expensive to pay for them, but the right people will pay for themselves in two or three months. We made a couple of key hires at the time, and they paid for their whole salary in like three months.
Brad Weimert: I mean, look, that’s the dream. The mis-hire is more common, and I think that that’s one of the rationalizations for smart money, right, is for bringing on money from somebody that can actually guide you through the process. So, fast forward a little bit. You gave Kevin Hart equity in your company in 2016. Did you seek that out to try to replicate the Howard Stern effect, or how did that come to be?
Tom Patterson: Not really. Someone came up to me in the office and said, “Hey, Tom, check this out on my phone. Kevin Hart’s dancing around in our underwear on the Instagram video.” Kevin was being Kevin. He had his shirt off, and we saw our waistband, and I’m like, “Oh, that’s cool. I’m going to find someone I know in LA. Someone I knew knew his agent, and I was able to get an address, and I sent Kevin some underwear and just a personal note, “Hey man, I’m a huge fan. I respect your journey. Ours has been similar at Tommy John. If you’re ever in New York, please come by, and here’s my number. I’d love to hear from you.”
Brad Weimert: Crazy.
Tom Patterson: Is Kevin the first and only person I’ve ever done that to? No. I mean, I’ve done that to hundreds of people over time. So, it’s not like I struck gold in my first try. But Kevin called three months later and said, “Hey, I’m going to be in New York and would you be able to meet?” And I was like, “God, actually, that sounds just like him. I think it might really be him.”
Brad Weimert: Oh, my God.
Tom Patterson: He came by, and he ended up being there for three hours. We just had a lot in common, connected in a lot of ways. And he came across our product in Nordstrom and just loved how soft it was, had been wearing it, was a customer. So, he already passed a litmus test like he was a believer. And he said, “Well, hey, can I invest?” And I said, “No, we don’t need the money.” I go, plus, I don’t think it’s really authentic. Everybody works with a celebrity or athlete, and you can slap our brand like a label on a NASCAR. And he goes, “Well, actually, I would want to be involved in some of the advertising and the marketing. I would actually put my own money into it. You wouldn’t even have to pay me.”
So, kind of the running joke is Kevin paid us through an investment to really become an ambassador. But you know, for us to work with one of the top comedians in the world was really natural because we took a comedic approach to men’s underwear, which in my opinion, was too serious. It was weird and unrelatable. And I think the way we spoke to the customer kind of cut through with this approachable swagger, humor, kind of like the way Kevin speaks to a certain extent. And it worked out to be a great partnership. We had TV commercials, a big event with the Kevin Hart line at Macy’s in Herald Square. Some of his documentary on Netflix was covered in our office. So, Kevin was an amazing partner when we were working with him. He’s still an investor of the brand.
Brad Weimert: Crazy. That’s a wild story. Of the other targeted gifts to people, who else did you try to target that way? Was it a part of the actual marketing process? Was it a one-off thing you did?
Tom Patterson: Oh, man. Well, we targeted you. Nothing came from that one.
Brad Weimert: You’re here, man. You’re here.
Tom Patterson: Yeah, I’m here. But that was…
Brad Weimert: I don’t have the audience like Kevin Hart, but you know.
Tom Patterson: You know what’s funny? I think there’s a lot of highs and lows in being an entrepreneur. Right before Howard Stern happened, we had a really big low, and I got a call one day in 2013 from somebody that represented this professional athlete called Cody Bryant. And my wife answered the phone in customer service. I’m like, “I haven’t sent an email. I don’t know who Cody Bryant is.” And I Googled it, and I think he was like a lineman for some football team. And I’m like, “I don’t think a lineman’s probably the best spokesperson for the brand.” Anyway, I get an email like two minutes later, and it’s from Rob Pelinka. He’s the president of the Lakers now. He was Kobe’s agent, Kobe Bryant’s agent. Kobe wanted to talk to me about the brand.
His stylist had given him Tommy John. And I looked up the stylist, and they had bought thousands of dollars’ worth of Tommy John, and he ended up calling, and we had a great conversation. I ended up going out to LA, met with him a couple of times, and really got to know Kobe fairly well. And we were working on a partnership where he was going to be working with the brand, in the US and in China. This was right after he tore his Achilles. And I remember meeting with him, and he had his Achilles in an ice bucket for the first hour. But what ended up happening is Kobe decided to kind of go down the sports marketing only kind of staying in that lane of sports.
And we found out on Halloween 2013. I remember exactly who I was with and where I was when we got the call. And it was really disappointing news because we had great visions of what we were going to do with Kobe, I mean, arguably the most recognizable guy in the NBA at the time. So, that was kind of a low. We kind of rethought things, and then three months later, Howard Stern hit.
Brad Weimert: Oh, damn.
Tom Patterson: And you could argue Howard maybe impacted our business more than Kobe could have. So, it’s funny how those things work out, and I think so many entrepreneurs are so close to breaking through, and they give up maybe when they have a Kobe moment, but I’ve always believed there’s something better around the corner. So, those lows more often than not become really big highs.
Brad Weimert: Yeah, they probably give up without the Kobe moment, but also I could see how that would be more deflating than it never happening, right? Like, you feel like, “Sh*t, I put all this time and energy into this. This is my big moment,” and it falls flat.
Tom Patterson: Yeah, and you still got a business to run.
Brad Weimert: You still got a business to run.
Tom Patterson: Yeah. So, I mean, we had to downgrade and work with Kevin Hart years later. But no, I love Kevin. Yeah, so we’ve had the opportunity to really meet and have different experiences with a bunch of great people. But the cool thing is they liked the product. It wasn’t us pushing the product down their throat. We’ve never really pushed partnerships, so we’ve at least wanted them to be more natural and authentic, you know? And we’ve been blessed to have a lot of those along the way.
Brad Weimert: Yeah, that’s wild, man. So, okay, in 2023, you sold a minority, but big chunk to private equity. Why not sell the majority at that point? You’ve been doing this for years and years and years. You no longer are operating the company. So, you did functionally move out of the CEO role. Why not sell at that point entirely?
Tom Patterson: Yeah, I think we love the business. You know, I think to take some chips off the table was one thing, but we fully intended to plan on continuing to run the business after that point. So, that was in late 2021. We hired a CEO in 2023. But what changes during COVID? You know, we thought we’d move back to New York, and we just made a family decision where we didn’t want to raise our kids in New York City, and the company needed a CEO that was there and present on a consistent basis. And the commuting back and forth just became too difficult as the COVID things kind of went away, and we just decided it was the best for the company to have someone there.
So, we couldn’t move the company, so we decided to hire our CEO at that point. So, the intent was never to really fully exit. That was never part of the deal. I think they always wanted the founders involved to a certain extent.
Brad Weimert: Well, those are two different things, right? One is getting an offer where it’s required that you stay, and the other is that you have a desire to continue to stay there and just take some money off the table. From talking to you over the course of the last couple of months, it sounds like there has been a significant transition to be less involved in the business. Would you have played that differently now?
Tom Patterson: To be less involved with the business?
Brad Weimert: Yeah. To sell the majority in ‘21 versus sell a minority stakes still be involved, and then two years later defer responsibility to a CEO.
Tom Patterson: I don’t know. Like, our term sheets all came in on March 13th, 2020. That’s when COVID shut down, right? So, term sheets went down significantly. So, you can never really time these things perfectly. I think everybody always has hindsight 2020. But honestly, no, not really any regrets. We’re still involved with the brand to a certain extent. We’re not running it daily. But yeah, it was a great run in New York, and we learned a ton, had great relationships from it. The brand is still doing really well. I think that’s kind of all you can ask for.
Brad Weimert: Well, you can ask for anything.
Tom Patterson: Yeah. Well, yeah, if I could go back and ask, I guess that the number was right, but it was never really part of the intent at that time, if that makes sense.
Brad Weimert: Yeah, totally. Okay, so one of the other things that I find interesting about your journey is that you co-founded it with your wife. Do you have any guidance on how to operate a business with your partner and also keep the marriage stable?
Tom Patterson: None.
Brad Weimert: How did it change from the early stages to the later stages?
Tom Patterson: Well, before we got married, we were both working from home. I was in a medical device sales job. My wife was selling software. She was in software sales. So, we had always worked together under the same roof. Then she started her own organic reseller company, selling organic products online. I was like, “Wait, I want to sell something on, I want to create a product and an idea.” So, she really inspired me to start going into Tommy John. And then a year into it, a year into Tommy John, she was laid off her software sales job, and I was like, “I need help. I can’t do this all by myself.” So, Erin’s skillset was always really complementary to mine, finance, anything in a spreadsheet, HR, operations, inventory planning, customer service, where I was more sales, marketing, brand, and product.
So, we’ve always kind of divided and conquered. And then as we grew, I mean, for me, there’s no one I trust more than my spouse. So, I think it can become challenging where as an entrepreneur, it never shuts off 24/7. It can be all you talk about. It can be all-consuming. So, we had to send guardrails discussions after 7:00 PM. Let’s have one night a week where we go out and talk. Nothing about business. Sometimes we go back to business just because we love what we do. But I think you got to find out what works for you. Tomorrow’s our 15-year wedding anniversary, so we’ve been married for 15 years together.
Brad Weimert: Congrats.
Tom Patterson: Thank you. Together for almost 20. So, yeah, I can’t imagine not doing it with her. You’re running the business, and we really ran it together in a lot of ways, dividing and conquering for the 16 years we were running it.
Brad Weimert: Yeah. I mean, that’s contrary to almost all advice people give around running a business, yet I have sort of a core belief that almost all things can be resolved through open, effective communication. And I think people are so bad at communicating that a lot of advice is true to the norms. And I think that the advice of don’t get in business with your spouse or significant other or family is true if you’re a terrible communicator. And I think if you just make a decision to be better at communicating, it can be one of the best things in the world because of all the things you just said, which is who do you trust more? Who do you want to spend more time with? Who can you relate to more?
And if those things are true and you’re good at working through the bad things, it would stand to reason that the synergy and the capacity to produce would be much higher and much more enjoyable.
Tom Patterson: Yeah, I agree. And, of course, there’s disagreements over time, right? It was not always roses and rose petals. I mean, we’ve certainly had different things, but I think we’ve always been able to resolve. And at the end of the day, we always say like, same team, right? We had the same goals, the same vision. We’re both going sort of in the same direction. So, I think the communication is important, but also like entrepreneurs, you’d burn out, and I would say like when I would burn out, she would carry the torch, and when she would burn out, I would carry the torch.
So, I have a lot more respect for the people that have done it, not by themselves, but not having partners, I think would be more difficult, at least for me, because I’m used to having somebody kind of like co-running it with me.
Brad Weimert: Yeah, I’m not. When you said that, my mind immediately went to, “Nope.”
Tom Patterson: Yep. I saw that without you saying it.
Brad Weimert: I can’t imagine having a partner. I’ve thought about it on several different occasions, but I think, as you just said, part of it is it’s just what I’ve known. And so, I would have to change a lot of patterns, and I would have to make a concerted effort to navigate that and different path. A lot of data points suggesting that I can do it on my own.
Tom Patterson: Well, I think too, to your point, there’s been a lot of great businesses that never lasted, right? Probably because of communication breakdowns, to your point, right?
Brad Weimert: And marriages.
Tom Patterson: Yeah, and marriages. And I think like the last thing you want is a business to be the killer of a marriage, like that defeats the whole point of getting married. Yeah. And I would say like you’ve probably hear of it not working out more than you hear of it working out.
Brad Weimert: Which is also true of any business partnership in any marriage in general. So, I guess all with a grain of salt. You had in an interview with Ed Mylett, you said experience can be your worst enemy. What did you mean by that, and how can CEOs guard against that?
Tom Patterson: Yeah, I mean, I would say like we had no experience in fashion, right? I never had “the right internship with the right connections.” I didn’t go to the right school or the right grad school, but I think I always had a curiosity and kind of like this not giving up when a lot of people would’ve given up mindset. And I think that’s back in 2008-2009, made a lot of listeners. That’s when the financial crisis happened. We went into the retail recession, the housing market crashed, and I read an article, there’s no better time to start a company than during a recession. I’m like, “Well, it’s only going to be up from here if I’m starting in the worst time,” but I have a product everybody needs that’s never been sold before. So, I knew it was only going to be growth. You could argue it was going to be slower.
And we kind of reinvent the new ways to market the underwear, new ways to design the underwear, new ways to speak about it in ways that hadn’t spoken. So, yeah, I think the reinvention happens during a lot of like changes. I think we’re in one right now with AI. I think that’s going to be a bigger change in what we went through in the recession. And I think a lot of brands are just going to get passed by because they’re not evolving and changing their platforms and making the right things to adjust to this environment, from design to marketing to operations. And like that’s kind of the reality, and who knows how it’s going to shake out, but I think we all have to adopt it, whether you like it or not, AI’s going to play a big role in all of our businesses, especially businesses like ours.
So, I think entrepreneurs have to be able to say, I always talk about you have to be able to clear your cookies. If you know a lot today and you’re an expert, you don’t know anything tomorrow because it changes so quickly. You have to come in with this almost like a rookie mindset every day. And if you know too much, it’s almost a detriment. So, I think you just kind of have to check your ego at the door and just be humble because there are a lot of things going on right now where experience, I think, can get in the way.
Brad Weimert: Speaking of checking your ego, ultimately, you brought in an ex-Calvin Klein CEO, Cheryl Abel-Hodges, to run your company. Bringing in outside leadership to a founder-led brand, especially one that’s been built to the size that you built it to, what is the biggest ego trap to avoid in that situation?
Tom Patterson: Oh, man. I think just being able to let go, make sure they’re onboarded. I think the most important thing is just giving them autonomy, but it’s also, I think, been a really tough couple of years with tariffs and duties and just what’s going on in the world. I think anybody would be crazy not to think it’s been a challenging time to be a CEO running a consumer brand in general. So, we take that with a grain of salt. But yeah, no one will run it like the founders. It’s hard. It’s not fair to really expect somebody to come in and be the founder. But yeah, she comes from a great brand. She ran Calvin Klein globally, really big business, understands all the distribution, operations, manufacturing, and fulfillment. So, she has the pedigree to really continue carrying it on, which we were excited about.
Brad Weimert: All right. So, you’re now three years out from that transition of not being CEO, almost. Almost three?
Tom Patterson: Yeah.
Brad Weimert: What does day-to-day life look like for you now, post-CEO? What are the good points and the bad points?
Tom Patterson: Oh, man. I wouldn’t say there’s really anything bad about it. I’ve been able to invest in a lot of companies. I think building relationships over 16 years you realize kind of how many people you know over time. And I think it’s opened up a lot of doors outside of just the brand allowed us to diversify a little bit more, rather than just into Tommy John advising a few entrepreneurs in the space. And then coaching my kids’ teams, take them to school, dropping them off, not really in a rush to kind of do what’s next, still helping from afar, still co-chair of the board at Tommy John, but kind of in this season of like 100-hour weeks, grinding it 24/7. It’s been a nice kind of decompression period at the end of the day.
And your kids are only this age for a short period of time, and we made the intentional choice where we didn’t want to miss out on this period. So, man, no regrets. It’s been awesome.
Brad Weimert: That’s awesome to hear. Almost everybody that I know, I don’t know that there’s an exception, actually. I think everybody that I know personally that has exited quickly gets back into something, has some existential crisis around meaning and what’s important to them, or gets into like a legit depression from it afterwards. What do you think prevented you from falling into that trap?
Tom Patterson: Oh, man. No one’s really asked me that question that way. I think because I saw that happen to so many people, I read so many stories about it. I watched so many YouTube videos, and I think like your purpose changes, right? It doesn’t always have to be about the company. I saw a pattern where so many people ran the company, and they got so many awards and made so much money, they’re like, the one thing they wish they would’ve got back is time. And I just think how fast time has gone since our kids were born. And how much of their first three to five years we missed out on. A nanny raising our kids, seeing them for one hour a day when they wake up, and maybe make a home before they go to bed.
Like, we missed out on a lot, miss out on weddings, events, family events. And after a while, you just kind of like, man, I don’t want to miss out on any more of this stuff. And I think that at some point your priorities change, and I think for us it was kids and COVID really reprioritized what was important to us. And, yeah, I think, is there things that we could have done differently with the business? Could it be bigger? Could we still be running it? Yeah, it’d be fun sometimes, but it’s not worth the trade-offs. But I think now what’s going to happen, which I think is really cool, in the next 10 years, there’s going to be a lot of 2, 3, 5, 10-person companies that are doing a lot of revenue that’s automated.
And I don’t think we’ll require as much in-person time as it did for us in the last 15 years if you can figure out how to put those systems in place. And I think that’s the advantage all the listeners have today, who are thinking about ideas is the grind will be different, I think in a lot of ways. And you hear about like these are lifestyle brands for founders that are launching right now. And I think it’s because they’ve also seen what the sacrifices the entrepreneurs before us kind of went through and missed out on, and it’s like, how do you do both? Does that make sense?
Brad Weimert: Yeah, totally. Well, I think historically you couldn’t do both. My belief is that there’s a fair amount of delusion in the entrepreneurial community around maintaining lifestyle. The number of f*cking people that talk about work-life balance and then expect to have greatness is hilarious to me. And I think we are moving into an era where the possibility of that is much, much higher than it’s been. And I also think that you can architect work-life balance currently if you don’t want greatness, if good enough is good enough, or if great for you has a different definition than it does for me. But at least the journey that we’ve been on so far, if you want to produce something astounding, you have to have an astounding work ethic to get there.
Tom Patterson: Yeah. I mean, it takes twice as long, and it’s 10 times harder, right? But I’m sure the way you think about your business is probably different than you did five or 10 years ago.
Brad Weimert: Absolutely.
Tom Patterson: Like radically different. You probably are like, “Who was that guy even thinking about that, that way?” But I think there’s a lot to be said for owning 100% of your business and not having to raise money and not really reporting to anybody. Especially if you can get strong advisors around you, which you obviously have, and have built an incredible business that I think supports a lot of your lifestyle in a lot of ways, where some people just weren’t able to do. I think that’s even harder.
Brad Weimert: Well, that’s good to hear. I think the bootstrap versus funded paths are so different, and the grass is always greener. One of the great experiences of my life has been being able to have conversations with people like you that have gone through the other path, and you’re sort of a hybrid because you mostly bootstrapped this thing and you had full control over it the whole time. But then I also talked to people that raised hundreds of millions of dollars, and many of them that exited net the same as where I am right now. Right? Or less. Because the picture from the outside is beautiful and glamorous and shiny, and the reality of the inside is dilution, and a boss that controls you, or a board that controls you in a different type of stress.
Tom Patterson: Yeah, I mean that happens a lot. You don’t really hear the details of those stories very often, but it happens more than you think.
Brad Weimert: Way more than you think.
Tom Patterson: And I think for us, we were fortunate to hear a lot of those stories, and I think it prevented us from even wanting to raise more money because of it. And there were times where we needed more money, right? But I go fly to China or fly to Egypt or fly to Israel and negotiate better terms with the vendor versus spending four days putting a PowerPoint together to pitch to investors. Because it’s also a huge time suck and very distracting to your business to constantly be raising money, because who’s running the business when you’re raising money? So, I think it just depends. You kind of pick your poison, or my poison was getting on a plane and kind of building that relationship versus giving more of my company away.
Brad Weimert: Well, speaking of lifestyle, when are we going to have Kevin Hart and Howard Stern out to my lake house for dinner?
Tom Patterson: Wouldn’t that be a fun group?
Brad Weimert: Yes, it would.
Tom Patterson: Oh, my gosh,
Brad Weimert: Yes, it would. Alright. What advice do you have for a new entrepreneur starting out today?
Tom Patterson: Find your own path. I think the challenge, there’s so much out there right now between podcasts and YouTube. It can kind of create like this, “What do I do? There’s too many things to do.” Like, if you listen to too many podcasts, it’s hard to even like take action.
Brad Weimert: Yeah.
Tom Patterson: I think find something that’s authentic to yourself. And just start, right? Start tinkering and testing. A lot of the best businesses didn’t really have a great business plan. I think you can overthink things. I tend to kind of start and build on the fly, but I think a lot of people are overthinking it and making it more complicated because by the time it’s ready, it’s too late. You missed the moment. For us, our product when we started this, now, 70% perfect. There were still a lot of problems. The fabric was thick. It could have been made a little nicer. The sewing construction could have been better, but it was really like the iPod 1 or the iPhone 1, and it’s improved over time. But proof of concept doesn’t need to be 110%. I think I see a lot of people just get stuck there.
Brad Weimert: That’s awesome. Well, Tommy John Patterson, appreciate you carving out time. Where do you want to point people? Where can people find out more about you if you want them to find out more about you?
Tom Patterson: Yeah, Tommyjohn.com and my Instagram handle is IamTomPatterson and TommyJohn for our Instagram handle for the company.
Brad Weimert: Beautiful. Thanks for carving out time, man. Until next time.
Tom Patterson: Yeah, thanks for having me.
Today, I’m talking with Tom Patterson, founder of Tommy John, the underwear brand that turned a frustrating problem into a 9-figure business.
Tom started the company after getting tired of undershirts constantly coming untucked while working in medical sales. What began as a simple fix turned into one of the biggest direct-to-consumer apparel success stories of the last 15 years.
In this conversation, we break down how Tommy John bootstrapped its way to over $100M in revenue before taking meaningful outside capital, why Howard Stern and Kevin Hart became game-changing growth channels, and what founders misunderstand about building premium consumer brands today.
Tom also shares lessons on raising capital, balancing wholesale with direct-to-consumer, building a company with your spouse, and why experience can actually become a disadvantage in fast-changing markets.
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