Why This Entrepreneur Wouldn’t Start Another Business Alone

“Takes Two to Tango” – Al Hoffman and Dick Manning

I’m going to come right out and say it, address the elephant in this post – working alone sucks. Don’t get me wrong, that wasn’t always the case.  In starting my pocket square line, Gangsterchief, I spent a lot of time debating fonts, packaging, production, costs and design all by myself, and in the early stages it fueled me. It felt good staying up late at night, burning the midnight oil, giving everything I had because I knew this was the path to success. Nothing could stop me – adrenaline high, head higher, dreams sky high.

Then it happened.

I truly underestimated how many decisions I’d have to make and the energy+time+sanity I needed to keep making them.

Working alone forces you to be your own motivational coach, your own boss, and your own fluffer. It will exhaust you when you’re most needed. It will kick you when you’re down. It will need you present when you’re ten steps ahead.  It will burn you out. Just ask the editors of Maker’s Row how many times I needed to extend my deadline for this article. It will force you to stretch your limits.

Lucky for you though, I’m here to give you the billion-dollar secret that took me a year to figure out.

You ready?


No one works alone. That’s a fact. Well, at least no one successful. If you don’t believe me, ask one of these entrepreneurs: Mark Zuckerberg had four co-founders, Steve Jobs had Wozniak, Dr. Dre has Jimmy Iovine, and even Nike has Michael Jordan. In a recent episode of The Tim Ferriss Show podcast, Seth Rogen and his partner Evan Goldberg responded to a question about why they don’t worry about writers’ block. Evan replied, “When one of us is not doing great, the other one can pick up the weight, and when one of us is uninspired, the other one can be inspired.”

We can all agree, 2 > 1.

So how do you get to 2? Here’s some advice on finding your future business partner:

1. Discover Your Resources

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Think about the person you ask for help the most, your go-to person when you need a second opinion. Think hard, I know you have one, everybody does. It could be your best friend, your spouse or your neighbor. Got it? Ok, now call them and give them an offer they can’t refuse. And don’t be stingy. On Shark Tank, Mark Cuban (who also has a partner, Todd Wagner) once said, “Better to have 20% of a $100 million company than 100% of nothing.” I couldn’t agree anymore.

2. Reach Out to Someone You Respect

Find someone who you admire and email them for some advice. Better yet, tell them how you could make their lives better if they join your board. Don’t have a board? You do now. If they’re interested and don’t have the time they will most likely refer you to someone who does. Tim Ferriss teaches Princeton students to connect with business mentors and celebrities with just a simple call or email. Check out how here and here.


3. Come to an Agreement

So you’re at the end of the manufacturing process ready to start selling. At this point you’re wondering “Why would I give up some of my company now when I’m done with the hard part?” The answer is: because you need help.  It never stops being hard. Try calling an agent/salesperson/rep and pay them a commission for helping you out. This way you won’t have to give up a part of your company right away. Who knows, if it works well, you could end up becoming partners.


Having a partner is like being in a marriage so choose carefully and play nice. When Jessica Alba started Honest it took her three years to find her three business partners. You may not have three years but for the sake of your own sanity, your friends and family around you, and your future billion-dollar business, please don’t do it alone. I know I won’t.

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