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What I Should Be Doing: Making Men’s Custom Shirts


A couple years ago my younger sister moved to Rio and started a massage practice. And I wondered, “Huh, why didn’t I think of that? Christy is living my life. That’s what I should be doing!”

Who among us hasn’t fantasized about turning a hobby or passion into a successful business? Of living a more thrilling life in a parallel universe?

That’s exactly the topic of a new series called What I Should Be Doing, which will highlight advertising people moonlighting as authors, adventure travelers, small business owners and other fun things.


We’ll kick off with Matt Tepper: VP, Business Strategy for AgencyNet AND Co-Founder/CEO of Second Button, a men’s custom shirt company.

Have you heard of Second Button? It was launched in 2010 by Matt and a couple colleagues to solve the dilemma of the ill-placed second button on men’s shirts, forcing guys to either flaunt chest hair or run around dweebishly buttoned up.

Once the team cured the button issue, they went on to improve other shirt aspects, so that everything – from collar, cuff, fabric and buttons – is customizable. No kidding, you can build your perfect shirt for about $80.

You can view all styles online and Matt is offering a 15% limited-time discount to blog members. Just use promo code “GoodCompany” when you check out. Want one of Second Button’s NYC stylists to take your measurements and work with you to design your shirts? No problem. Schedule an in-person fitting appointment here.

Here’s how Second Button was brought to life:

JS:          At what moment did you decide to launch Second Button? Why was an important goal for you? How did you explore the idea before undertaking it?

MT:        There wasn’t one specific moment, it was a general feeling that built up over time that I’d love to have an outlet for my ideas and strategies that did not require someone else’s buy in.

I started with consumer research to see if other men in creative industries were as frustrated as I was with off-the-rack dress shirts. Then I did research into the cost side of the business to see if I could profitably address the issue I had identified. Only then did I do some basic projections to see how many shirts I would need to sell a month to make it into a sustainable business.

JS:          What goals did you set for yourself in making Second Button a reality? How long did it take from start to finish? When did you find time?

MT:        My goal was to create a cash flow positive business that could provide me with an outlet for my ideas while bringing in a consistent flow of revenue. My original goal was for Second Button to be a hobby; I never expected it to grow as much as it did and become a viable full-time business.

I basically made the time. Nights, weekends, and any spare minute I had. It wasn’t ideal timing, given my son was born one month after Second Button launched!

JS:          So what’s the scorecard: How do you feel now that Second Button is over a year old? Are you pleased with the results? What would you have done differently?

MT:        I’m very pleased.  We reached cash flow positive in Month 13, and it’s been consistently growing. It helps that I’m now three days a week at AgencyNet and have two full days to devote to Second Button.

The biggest rookie mistake I made was thinking I could treat Second Button the way I do my client’s businesses. There is a HUGE difference between how to run business strategy for a start-up and a Fortune 500 company. A much greater difference than I ever could have anticipated.

JS:          What’s your advice for people who want to launch their own retail/ecommerce business?

MT:        Start small and simple. Take the most critical piece of the business and only build that. It’s impossible to predict how your business will change and evolve over time. If you invest too much in functionality that you think may be useful, you will unnecessarily waste time and money. Let your customers show you how your business should evolve.

Check out Second Button styles

Second Button on Facebook

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