Coulda, Woulda, Shoulda: 3 Tips for Starting a Business for First Time Entrepreneurs

Coulda, Woulda, Shoulda: 3 Tips for Starting a Business for First Time Entrepreneurs
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Founder and CEO Tom Patterson with his wife Erin Fujimoto, co-founder and head of merchandising in the Tommy John design studio.
Founder and CEO Tom Patterson with his wife Erin Fujimoto, co-founder and head of merchandising in the Tommy John design studio.
Tommy John

Life is comprised of daily decisions. Many of them are menial, some are more substantial. The biggest decision I ever made meant I never again had to wonder “what if.”

I was at a crossroads eight years ago. I was laid off from my job as a medical device salesman and I had a decision to make; Do I get back on the horse, find another job in the field, or do I change course entirely and pursue the idea that’s been nagging me for years?

I spent my entire career as a medical device salesman frustrated with the one-size fits all mentality of traditional undershirts. My undershirts would constantly bunch and would always come untucked. They’d yellow easily and the neck would often stretch out. It was irritating. Maybe I was alone in my frustration? Maybe I wasn’t? But I couldn’t let go of the “what if.”

That’s when I decided to launch Tommy John.

I had no previous experience in clothing design, manufacturing, or even entrepreneurship, but I was set on finding a solution. I found fabric and a tailor to sew up some prototypes, and when we finally created the fit and feel that I liked, I sent samples out to my friends and family to gauge feedback. I wanted to see if anyone else shared my frustrations. There were more than I ever anticipated.

Fast forward eight years and Tommy John has grown significantly. Where it used to be just my now-wife and I working out of our 500 square foot apartment in New York City with our 120 pound Bernese Mountain Dog, we now have a team of 50 working out of a 17,000 square foot office in the Manhattan Financial District. Reflecting on how far we’ve come gives me the confidence to go much further.

Making the initial leap into the murky waters of starting a business is never easy. But neither is watching your idea being built and executed by someone else. Here are my top three pieces of advice for first time entrepreneurs:

  1. Do It.

I launched an underwear company during the recession. On paper, not so smart, but I wouldn’t be where I am today if I hadn’t seized the opportunity and allowed myself to become completely consumed by it. There will always be a reason not to. At any given moment, you can come up with a million excuses why now is not the right time, or why it isn’t the right idea. Simply do it, because it’s better to try, fail and learn, than to not try at all. When you’re starting out, time is your greatest asset. Use it to take any step forward. Take a meeting, make a few phone calls, whatever it takes to set yourself in motion. Do it. You need to commit to your endeavor entirely, because the idea is only as good as the execution.

  1. Stick it out.

There were times in the not so distant past when the future of the entire company (along with my family’s) resided in a single order form. There were times when my now-wife and I simply couldn’t afford to go to dinner because we invested everything we had into men’s underwear. It was hard, but it’s important to stay committed through it all and have faith. You need to know, that there will inevitably be a time when you want out. Whether you miss your revenue goal, or become overwhelmed with scaling the company, you may be tempted to cut your losses. Don’t. Starting a business is hard, but running a business is even harder. You have to take the good times and the hard times in equilibrium. And when you’re truly overwhelmed, ask for help. There’s a network of entrepreneurs available to you who have been there before. Don’t be too proud to seek the help needed to overcome whatever obstacles you’re facing.

  1. Be focused.

I barged into an antiquated industry that in many ways had been unchanged for 25 years. All other big players were just that – BIG players. How could I compete with established brands that were already positioned as leaders in the industry? Numerous people warned me about diving in at the deep end and the difficulties in trying to stay afloat. I didn’t listen. I started Tommy John to solve the real problems men have with their undergarments – the problems that I, myself, have experienced. There will always be other companies with different budgets doing different things. It’s easy to get wrapped up in that thought and often difficult to resist trying to compete head on. Don’t. Stay true to your own course. Don’t be reckless. Find what works for your company, prove that it’s successful and then pour gasoline on the fire.

From one first time entrepreneur to another, I can promise you it’s not going to be be easy – if it was easy, everyone would do it. It’s going to be extremely difficult at times. You'll reach the highest of highs and plummet to the the lowest of lows. You’ll be pushed to your absolute limit and with great joy will come great fear. But I can guarantee that you’ll regret it if you don’t try. In the end, that’s all you can do, and I promise you that trying is worth doing.

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