I'm hardly a fashion plate. In fact I'm probably a poster child for poor fashion sense and dressing down. Jeans and Under Armour Heat Gear T-shirts make up the bulk of my wardrobe. I pretty much dress only for comfort, admittedly sometimes to my detriment.

But still: I can tell when clothes look good on other people. I can tell when the clothes I'm wearing make me feel insecure or self-conscious. And while I never think I look particularly good, I can tell when I'm wearing clothes that make me feel more confident, more relaxed, more... well, just more.

For a guy like me that feeling can be hard to come by, though, so I definitely notice when it does. That's why, after wearing -- and loving -- a polo shirt that fit well and felt great, I decided to talk to the entrepreneur who made the shirt: Brian Berger, the CEO and co-founder of Mack Weldon. (I love talking to the entrepreneurs that make products I love.)

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In 2012, Berger and co-founder Michael Isaacman launched Mack Weldon, designing and selling their own socks and underwear brands. Five years later they've expanded to offer almost 200 different styles of socks, underwear, t-shirts, polos, and swim and activewear. To date they've sold well over 1 million units and enjoyed triple-digit sales gain every year.

How have they built a thriving brand -- and managed to make someone as unfashionable as me like their shirts, underwear, socks and activewear?

Good question.

So you decide to start a clothing company... and you focus on underwear and socks?

The original thinking was to choose a product category that had been overlooked or commoditized, and provide a specific but subtle upgrade. We figured it we did that well...

Most guys have a similar mindset to yours. Some will sacrifice comfort for fashion, but even then they still start with was they feel is comfortable. Yet we're also seeing a counter-trend: Guys are caring more about what they wear and how they look.

Both of those factors work in our favor. If you're a guy with a slim, fit silhouette, you once opted for the standard fit... but now you don't like it. You feel you're in better shape.

Yet you still want to be comfortable.

I get that, but still: Underwear and socks?

I always hated the process of buying underwear and socks. The marketing never made sense, the pilgrimage to the store was awful, then you faced choice overload... and the product never lived up to the promise. Underwear are your base layer; they dictate how everything feels.

So I wore stuff into the ground. One day my wife literally threw out everything and said, "Guess what you're doing today: You're buying new underwear and socks." I went to a department store, stood there looking at a ton of stuff, and the salesperson walked over and said, "Are you confused yet?"

I had been in the consumer Internet businesses, investing and M & A for a media company that was acquiring and investing in companies. I realized this was the chance to go out on my own and differentiate. I have these issues, other guys do too... so I pulled the rip cord and started the journey of creating this brand.

Retail clothing is a big leap from M & A, though.

Maybe, but then again, this business is all about consumer buzz, great marketing and distribution... and I thought, "If you can crack this nut, if you can solve this problem and really deliver an upgraded experience for men... there's an enormous opportunity to build loyalty.

Men typically buy on a regular cycle of replenishment. I felt that was the opportunity -- not just new and flashy and surface-level, but delivering value that creates long-term customers.

Long-term customer loyalty is the holy grail of retail -- and any other business -- but it's extremely hard to come by.

We started with product and brand.

We needed to get product development rolling so we could apply what we were thinking about in terms of our brand. I was jumping on airplanes, flying all over, meeting with mills, meeting with factories....

Then couple that with brand development. How do you translate the essence of the brand and create a visual esthetic point of view that will resonate with customers?

Ultimately I connected with my co-founder. He has over 25 years of fashion apparel expertise, we connected with a guy who was formerly head of products for Nike and Adidas, and he was head-over-heels about creating the brand. He helped us to not only execute products that were unique and differentiated but also to translate aspects of the brand into the product. The details are subtle, but they help translate the brand onto the product.

You see a lot of one-hit wonder startups that conceptualize on Kickstarter, fund their first order, sell some product... and then, later, if they get successful they think about building out the brand.

For us it was always about about presenting something to the customer that is comprehensive and can be expressed in more than one product category. If you bought our underwear you might naturally think we're just an underwear company, but we wanted our customers to focus on product innovation and utility and comfort and fit and realize that we could accomplish those things across a broad range of products.

That's how we went from socks and underwear... to everything else.

Every entrepreneur needs to have some amount of irrational optimism, especially during the planning stage. But what were those first days of actually having product to sell like?

You're right. Belief is one thing, proof is another.

We built the product line, built the website, set up the supply chain, set up fulfillment... and then we wrote a gigantic check for an initial run of inventory.

We were confident, but still: Were we smart enough to pull off an initial launch? We went on a full-court PR offensive. What really set us off were all the influencer sites, sites that spoke to our target customer audience. Those guys all wore our stuff and had a direct reaction to it. We were fortunate enough to get coverage on all these targeted sites, and it validated the value of our product and drove a lot of initial momentum.

We sold through in half the time we thought we would, but of course that created another problem: Now we had to buy more, and more... and that means the anxiety never really goes away because you're constantly raising the bar.

How have you continued to grow at such a rapid rate?

One way is through an expanded version of what I just described. We're still very focused on raising awareness through PR and editorial for new customer acquisition.

We also have a very active forward leaning marketing strategy where we spend money on Facebook, Google, etc to cost-effectively expose customers. That's really the strategy for customer acquisition.

Parallel to that is the team that focuses on maximizing the long-term customer relationship. Our business model is based on retention and loyalty. We have people opt in, yet we took the contrarian view that it is important to message the customer at the right interval in time to replenish. We do that based on our customer's needs, not our needs.

Then we focus on new products, and exposing our existing customers to new categories.

Which creates the classic flywheel.

Exactly. It really is circular. The better we get at acquiring new customers, the better we can engage those customers and make them loyal customers, which gives us the opportunity to expose them to new products...

Which means you can afford to spend a little more to acquire new customers.

In essence, yes: We can spend a little more to get you... because we'll keep you.

Because we don't have a formal subscription model, though, the burden of keeping a customer is all on us. Most subscription companies understand churn and play to that, knowing that some customers will keep paying simply out of habit. We think it's our job to keep customers.

That means we constantly have to be better. If we're going to launch a polo, the shirt you liked, well, polo shirts have been around forever. If we're saying our polo is an upgrade to a classic, it better be. The guy who wears it has to say, "It fits better, it feels better, it wicks away sweat..."

That's how we win. We have to be better.

Another way to "win" in retail, at least in the short term, is to compete on price.

When you look at brands and retailers it's often a race to the bottom with respect to pricing. Many companies use heavy-handed promotional strategies to generate customer engagement. We knew we were entering a category that is highly promotional, heavily discounted, with flash sales... we decided that if we ever became a promotional brand we would never build a substantial, long-term customer base and business model.

We take a different approach. Based on how much customers spend, they can enjoy discounts at the next level. That's how we've never had to resort to heavy discounting, and that lets us preserve our relationship with our customers.

Of course it also means we have to come up with interesting ways to activate our base while preserving price integrity, but that's a challenge we're happy to take on.

Five years in, any lessons learned that other entrepreneurs can benefit from?

There are plenty.

When you first start out, it's easy to really sweat the small stuff. I was obsessed with creative details and design details. I think they're critically important because you only have one chance to make a first impression... but from the standpoint of the amount of time I spent versus the size of the issue, I spent more time on those things than was absolutely necessary.

Another is decision making. One of the things you hear with tech entrepreneurs is break things fast: Move fast and break things. I am generally a careful person, but when you do something like this you have to be comfortable stepping into that zone of "I don't know how this is going to work, we haven't tested it as much as we want..."

When you have data to inform your decision making it can make you move more slowly than possibly should.

Over time you realize that you can make decisions more quickly. With experience you build up more scar tissue and can make decisions faster.

The last one is learning to let go. One of the most important things for a company in our stage is hiring great people. We look for self-starters, people understand the landscape really quickly and can just go.

As an entrepreneur you want to hold on to things... but letting go and letting the team lead in various areas of ownership has enabled us to move much faster.

That's something I didn't do so well early on. That's to be expected: There will be plenty of "first rodeo" moments. Learn from them, and next time make sure you do better.