Make Millions Selling T-Shirts to High School Athletes? You Bet.

When a friend first recommend that I talk to Chad Hartvigson for this blog, I was skeptical.

A guy who runs a business selling screenprinted t-shirts for high school sports? Not sexy enough. For someone like me who mingles in the self-absorbed, “[NOUN] 2.0” buzz of Silicon Valley all day, every day, the idea of debuting with a t-shirt printer was so unglam as to be a downright blogkiller.

I love being wrong.

Chad’s company, Prep Sports Wear, blows many of the Web 2.0 startups down in SoMa completely out of the water. For one thing, Prep Sports Wear actually makes money (ouch!).

For another, you don’t have to be a fancypants Bay Area yupster to understand the basic American appeal of comfy loungewear with your school’s logo on it. And lastly, though I haven’t yet met Chad in person, he’s got a damn sexy phone persona for a former semipro-baseballer (wink).

During our hour-long conversation last Tuesday night, Chad struck me, incredibly, as being simultaneously innocent and shrewd as hell. He was also pretty fun to talk to, and offered a few surprising nuggets worth repeating.

What I learned from Chad

1. Entrepreneurship does not necessitate expertise. Chad wasn’t a t-shirt manufacturer. He wasn’t a tech guy. He was an athlete who wore t-shirts and was interested in technology. He wasn’t an expert in any of the areas that were core to his business. But, he thought he had a good idea, so his job was to rally the experts.

2. The day job will save you. Prep Sportswear started as a teeny, tiny side project when Chad was still a college athlete. It stayed as a slightly less tiny side project when Chad was a grown-up working at a financially stable, regular job. The security of his day job actually gave him the confidence to pursue his side project to its current glorious state – precisely because everything was NOT on the line.

3. If you don’t like your boss, it might not be your boss’ fault (gasp!). Maybe you just don’t like working for other people, like Chad. Great entrepreneurs recognize this in themselves and, instead of fuming against their company or their managers, channel it into projects that will get them out of the employee lifestyle.

4. Laugh in people’s face. I loved when I asked Chad how he felt when people told him this was a stupid idea, or that he was crazy, or that he would fail. Instead of just giving me some inspirational blahblah about adversity making you stronger, or even just saying he felt bad, the way I probably would have felt, he just said he laughed. People don’t know what they don’t know, and it’s funny sometimes. But seriously, don’t take it (or them) too seriously.

See the full interview notes below.

How did you get your start?

I was in college at the UW, playing baseball for the team there. Huskies football gear was everywhere, but you could never find a sweatshirt about anything besides football. We wanted something for us, so, as team captain, I started taking orders.

The first year we sold to players and families. The next year, the coach asked me to do it again, and to help out with the softball shirts the year after that. It came from a need by the team, it wasn’t a business idea, so I always sold at a cost.

I had this idea that we could really make a business this way, selling one-off, customized t-shirts in low volume to a massive customer base. But it was 1995 and the Internet was just starting to take off. There was no real e-commerce then and no way to make it happen with the technologies that were available.

So, then by some magic you still made it into a multimillion dollar biz?

Well, eight years later, my dad, who sold t-shirts from manufacturers to retailers, got laid off and needed some help. My brother and I thought about ways we could bring him into our insurance sales business at the time, but there was really nothing he could do there. So, we started thinking, Hey, what about the t-shirt idea…

So my dad and I ran a beta test with six schools in the area. We went around and did a bunch of surveys with them, and figured out that the concept worked. People liked the idea and thought an online store for school merchandise would be very useful.

Oooh… beta test. How did you figure out which six schools to survey? Some complex algorithm, I assume?

Those were the only six schools that actually returned our calls.

Customized merchandise for high schools – doesn’t that go against most desirable business principles (high volume, low-cost mass production, deep-pocketed customer)?

Lots of people were out there trying to sell 500 shirts to 1 customer, but I wanted to sell 1 shirt to 5000 customers.

I was looking at the long tail of consumers, and I saw a need. Most printers don’t even have Internet in their offices, and they won’t serve you if you just want to a couple of shirts. I wanted to aggregate that market.

Did you know that you were going to scale your business to its current degree – affiliate program, corporate clients, targeted ads and co-branded stores – from the beginning?

Our goal was to scale the business from day one. Anything other than a “big hit” would not be worth the time or risk.

How did you craft your vision without being an expert in the technology that would take you there?

I don’t think you need to understand the technology. You really need to understand your vision and be able to communicate it to others in a way that allows them to share it. Once you’ve done that, you can attract others to help you execute it.

I had some friends working at big tech companies in the area, so I talked to them a lot. Eventually, one of them introduced me to Ivan, who became my lead developer, and eventually the CTO.

How did you pay Ivan when you first met him?

Uh, well, I paid him entirely on equity.

It helped that he had some pretty good stock options from his InfoSpace days to help him keep a roof over his head.

How long did it take him to decide to work with you?

I met him at a Starbucks on a Wednesday night. I told him about the idea, and I was just really excited about it. He said he’d let me know within two days, and on the second day, I got a call from him.

Wow. When I get ideas, I only feel good about them if other people tell me, “That’s a great idea! You should do it!” Didn’t a lot of people tell you it was a stupid idea in the beginning? And then here you’ve also gotten this nice Russian man involved…

Yes, a lot of people told us it was crazy, or stupid. People laughed, and no one would believe us.

But, as a person who’s played baseball since being a little kid, including professionally, you have a lot of people telling you that you can’t do this or you can’t do that. In sports, people are always trying to talk you down – you can’t succeed unless you figure out that all that doesn’t matter. The only thing that matters is what you believe personally.

The fact that it started as a side project was important too. I had my other business that I worked on with my brother, and I knew I’d be financially ok with that, so it took the pressure off a bit. I also never took VC funding or anything like that. It was just a little bit of money from family and friends, so I never felt like I had to go running around pleasing all these funders and doing things with my company that I didn’t want to do.

Ivan  didn’t really get the t-shirt idea at first, because in Russia you had a choice of either a black t-shirt or a white t-shirt. It didn’t make sense to him why people would want all these customized sports shirts. But, for someone who’d come from Russia only four years prior, he really embraced the idea of American entrepreneurship and was looking to get away from the corporate atmosphere of his last job.

So, why did you do it all? Bucks? Babes? To fulfill your dream to be on Ask The Entrepreneurs?

I grew up watching my dad going through the ups and downs of working for other people. In college, my goal became to never work for someone else. And, I saw an opportunity that wasn’t there in the insurance sales business I worked on with my brother, where your success was always 1:1 – limited to how much you as one person could get done.

Our business is basically a technology company. We’re now 50 people using technology as a platform to monetize a massive base of consumers. We offer schools and teams completely customized items with a minimum purchase of one, and we’re making money doing it.