After the release of my new book I've done a lot of speaking events. In most cases I can get away with dressing down, as a la Steve Jobs it's part of my brand (even though it's really because I'm not comfortable wearing anything other than jeans and Under Armour t-shirts.)

Still, I sometimes needed a suit. But the suits I owned were dated and fit poorly. (I basically looked like I walked blindfolded into the men's section at J.C. Penney's and came out wearing whatever I happened to stumble upon.)

So I wanted something nice. Something current. Something that actually fit me.

That, of course, meant buying a custom suit. Custom suits are made by tailors who help you choose the right cut and style for your body type, who measure you themselves, who fine-tune the fit... it's an in-person (and, as such, expensive) process. 

But going to a tailor made me uncomfortable in the way that the thought of buying, say, a Porsche makes me uncomfortable -- like I'm pretending to be someone I'm not. (I know. A psychologist would have a field day with me.)

So I did get a custom suit. But I got it online.

And because I love entrepreneurs, I tried a suit from Black Lapel, a startup founded by Derek Tian and Warren Liao. First-time entrepreneurs, Derek and Warren set out to solve the problem of creating made-to-measure suits without (literally) touching the customer.  

The Process

Here's how it works. First I picked -- okay, actually my wife picked -- a Blue Gray Birdseye custom suit. Then I made further choices: I went for a tailored fit, two buttons, notch lapel, double side vents, slanted flapped pockets, no pleats in the pants... classic stuff. 

Then I went a little wild and chose a red inner jacket lining. (I thought it would look cool, but also rationalized that if it turned out not to look cool... no one would see it). Choosing customizations was easy.

Then I had to provide measurements. Fortunately the site walks you through the process, providing instructions and videos for each measurement. If you've never been measured for a suit, be prepared to watch a few of the videos more than once. The instructions are very clear, but for someone like me it still seems hard.

And no matter how many times you double-check your measurements, you'll still wonder if you got it right. (And that feeling won't go away until your clothes arrive.)

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Even so, the customization process took just over 15 minutes, which might sound long in the online world but is way faster than going to a tailor. (And way better than having to fend off a pushy tailor who constantly tries to up-sell you.)

Three weeks later, my suit arrived. 

The Results

I hesitated before I opened the box. I knew it would be a good-looking suit. But would it fit me? Did we do everything correctly? My wife was especially worried about the fit since she did all the measuring.

I pulled on the pants. They felt like they fit. The shirt felt like it fit. I slipped on the jacket and it felt like it fit.

I turned towards my wife to see what she thought and she gave me that look that says, "You look great..." which, if you've been married for more than a few years, you know is a priceless look.

I looked in the mirror and also thought my suit looked great. And I thought it fit perfectly.

But I'm not the best person to judge -- so I went to a tailor. I told him I had just bought the suit but wasn't sure if it fit right. He lifted, and pulled, and felt, and assessed... and finally stepped back and shrugged as if to say, "There's no money in this for me," and told me everything looked right.

That confirmed what I suspected. I'm the opposite of fashion conscious. On a scale of 1 to 10 in terms of fashion sophistication, I'm a -3.But I do know when the clothes I'm wearing make me feel insecure or self-conscious. 

And while I never think I look particularly good, I know when I'm wearing clothes that make me feel more confident, more relaxed, more... well, just more.

And my custom suit definitely makes me feel more.

The Story Behind the Story

Regular readers know I like to talk to the entrepreneurs who create products I love -- so I talked with Derek Tian who, along with his friend and co-founder, Warren Liao, started Black Lapel in 2012.

Derek and Warren have spent the last six years growing Black Lapel into an online destination for custom suits, shirts, tuxedos, separates, and accessories (and impressive gross revenues.)

If someone told me they were thinking of selling custom suits online, I would have said, "Good luck with that." So my first question is, "Why online customer suits?

Trust me, there were plenty of naysers. That's especially true since Warren and I are not just first-time entrepreneurs, we're first-generation entrepreneurs. 

But it all started because we were bored. I was working in commercial real estate finance. Warren was in investment banking. We were both doing very well but we were also looking for a different challenge.

As consumers, we had experience with suits and where we tended to run into problems was with affordability and even more so with fit. So we thought, "How do we solve this?"

You weren't the first to try.

Absolutely not. At the time direct-to-consumer online customization was spreading quickly. We weren't the first to the table. That was helpful, because we could look at how those companies executed.

One of the biggest things we noticed was the typical e-commerce approach of starting a business and immediately looking for 10X growth. But with a complicated experience like custom clothing, getting the fit right, getting the right look... a lot of things go unaddressed when you try to scale too quickly.

That was a great lesson. We had to really value the customer and the customer experience, and we prioritized it. That's why our first two hires were customer service and content marketing.

I get customer service as an initial hire... but content marketing?

That might sound counterintuitive, but because so many people weren't familiar with custom clothing, we needed to address that right away. We needed to "condition" our customers, to help them understand the value of comfort, of fit, of lifestyle... and to help them understand that we could provide all those things through an online experience.

That was our thought process. And it turned out to be a really good decision. 

But we didn't know to call it "content marketing." Later we started hearing that term and thought, "Oh, so that's what we've been doing." (Laughs.)

Marketing and customer awareness was a challenge, but the operations side had to be extremely hard to work through.

You're right, especially since neither of us had a fashion background. The nuts and bolts were probably the hardest part of getting the business off the ground.

To understand, for example, the different types of suit construction, how measurements get turned into patterns and suits, undertand suit construction, know how to work with the factory, to manage just-in-time inventory since everything is custom-produced... learning all of those things was incredibly challenging. It took the better part of a year before we were ready to prototype. 

So you have a MVP (minimum viable product), but that's a risky moment for any startup. It's a cliche, but you only get to make a first impression one time.

The risks involved with a MVP are big, particularly in the nascent phase of a business.

We were careful with the fabrics we solicited and with setting the right expectations. We focused on friends and family, got them to try it... and asked them to be brutally honest about the experience and the product.

We also worked with a handful of style bloggers and early brand ambassadors so we could get more educated feedback. They had real-world experience and understood the marketplace pain points.

When did you know you "had something"?

Once we did all our testing and got the website online, we had some early luck. One was when we were voted one of Lifehacker's Top 5 custom clothing companies. That gave us a lot of confidence and validation.

From there we did an AMA on Reddit that was fairly well attended; we probably spent the better part of 15 hours responding to every question that came our way.

Those things helped us know there really was a demand for our product. People were curious. They had problems buying suits off the rack, they didn't have the budget for a bespoke suit... they were looking for something in between.

That inspired us to keep going.

Talk a little about content marketing. Lots of companies do it. Relatively few do it well.

We want to build a relationship through our content. For example, one thing we did early on was try to help people understand what to wear beyond just a suit. Like what to wear when a dress code is involved. 

All along our plan was to branch out. And what's great about it is our customers give us a lot of feedback; that's where much of our product development comes from. Customers would ask for an off-white off white tuxedo. Or they'd say they love our suits and shirts, but where is the outerwear? So we did a cream-colored dinner jacket, and we did topcoats. 

That dialog is critical because it tells us whether we're working in the right direction.

We had our share of luck, but you can't build a sustainable business with just luck. You really need to listen to your customers, which means finding ways to engage them and build a relationship.

Looking back, what would you do differently?

In retrospect we would do a better job of saying "no" to good ideas. Good really is the enemy of great.

We hired a good team of people with very ambitious ideas... but when you have all those ideas, it's tempting to decide to go for them all. Ultimately, though, those ideas require more than one person to execute. They almost always require cross-functional, shared resources... and in any company, and especially a bootstrapped startup, there just aren't enough resources to go around. 

Two or three years ago a lot of ideas were being worked on... but we were often missing the deadlines for those projects, and the execution wasn't quite as good as it could have been.

I wish we'd had the foresight to know we needed to be very careful with our capacity. That's hard, though, because when you and your team are excited about what you do... you naturally want to do a lot.

Now we try really hard to channel all that enthusiasm, help our people succeed individually, help them succeed organizationally... and do it in a way that we can maintain over a long period of time.

For all the aspiring entrepreneurs who have an idea but haven't gotten started yet: What's the best part about running your own business?

For one thing, I am definitely not bored. (Laughs.)

If anything, I don't get as much sleep because there's so much to do. We have a team in the U.S., a team overseas handling sourcing and quality control, we conference calls from 8 a.m to as late as 10 p.m.

But it's really fun, and probably what I enjoy most is that there is still this sense of newness to everything. We honestly learn something new every day.

That's what attracted Warren and I. We share that desire for intellectual challenge. Early on we documented a set of core values for the company, and one is that we want to "be better tomorrow than we are today."

As we make business decisions and build our team we look for people who share those core values and help reinforce those core values.

Because of that, it hasn't been difficult to maintain our level of intellectual curiosity -- because we're surrounded by smart, curious people.