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A Startup’s Worst Enemy

Question: What’s the biggest challenge with starting a business, or a startup’s worst enemy?

Answer: The biggest challenge is who you are working with. Are they encouraging you? Are they not encouraging you?  It’s probably taken you a lot of time, effort, and consideration to get to the point where you could tell your friends about your business idea. I don’t think peers recognize how damaging it can be to tear down a fledgling idea.

I often wonder how many businesses don’t start because of these other people? When you get ripped by your friends who call you a dumbass and say they can’t believe you’re doing this, it’s hard to ignore them. That environment hurts new businesses.

When I was a DJ, my dad literally asked me, “How do you make money? That doesn’t seem like a real job.” I replied, “Well, I show up at the club with all my music, I play records, people dance, they leave at the end of the night, then I get paid and I go home.” But as a school principal, he could not wrap his head around the idea. “You pay your mortgage by playing music?” I have a history of ignoring my parents (with love of course). If I had been wired a different way I might have listened to them and given up on my passions. If I followed the plan they laid out for me, my life would be totally different. It wouldn’t be bad, but I wouldn’t be reaching for my own dreams.  I would have been acting on someone else’s dreams and not my own, because of listening to a startup’s worst enemy advice rather than what I want to accomplish.

These environmental challenges are the sleeping giant nobody sees. People will listen to those they’ve established trust with i.e. their parents and friends. They’ll think, “You’ll never give me bad advice. You love me.” But we give these people too much credit. If I had listened to my parents, I would be a police officer. Which could not be further away from what I do now. My dad’s logic for this job made sense though. I could work for 20 years, retire, and get a pension. He also thought since I wasn’t very academic that this would be a good fit for me. But I knew myself, and I found my niche elsewhere.

A startup’s worst enemy is the failure to take action. All the people who paid attention to what other people said will wake up 10 years from now, and think “I missed my chance.” I never ever ever want to look back and think about all the opportunities I didn’t take.