The Greatest Lesson I Never Learned

For as long as I can remember, my father has been an entrepreneur.

The entrepreneurial gene, to me, is the single greatest gift I was ever given. It feels like it was a part of my DNA, but in reality, I’m an entrepreneur because of observation and desire. It’s the only life I knew growing up and all I’ve ever wanted.

While I give credit to observation, I also give a ton of credit to the micro-lessons I learned along the way. These weren’t intentional lectures, but more subtle nudges that stuck with me.

The simplest and biggest of which was a question he often asked me, “Why don’t you just do that for yourself?” While on the surface, it’s a harmless question. In reality, it has been both a blessing and a curse. On the plus side, it’s allowed me to think as an entrepreneur. In every job I’ve ever had, I’ve been able to dissect a business from top to bottom and essentially reverse engineer its success. On the negative side, I haven’t been able to hold a job for more than a year. The question my father always asked, continued to repeat each day. Eventually, I’d get resentful towards the company that hired me and leave to do something on my own.

Another micro-lesson that I was taught growing up was to “never go into business with your friends or family.”

This one I witnessed first-hand.

In late 2007, after 20 years of operating a business together, my father’s childhood friend, and business partner, went behind his back to remove him from the company they started together. That wasn’t the worst of it though. He did this while my dad was taking a leave of absence from the company because of a brain tumor.

Worried that the brain tumor would end his life, leaving half the company in my mother’s hands, he turned the employees and stakeholders against him.

Long story short, my dad survived, but his friendship and partnership did not.

While the experience stuck with me, the lesson did not.

Nearly every business I’ve started in my life, I’ve done with a friend. Quite honestly, as a startup looking for funding, it’s almost frowned upon not to have a relationship with the person you’re in business with. Investors want to hear that this person is practically a life partner. It’s a complete contradiction to the advice I received growing up.

Aside from that, it’s just more fun starting a company with a friend.

Most of the ventures in my life have only generated little to moderate success, except for one. This particular one has generated a ton of success. In fact, if I mentioned the name, you’d probably have either used it or heard of it.

I started this particular company with my best friend. Ultimately, I had to fire my best friend.

I’ve always told myself that I wouldn’t let a business get in the way of my family or my friendships. That was, of course, until it happened.

I’m not going to get into the details, but I can tell you that it had everything to do with friendships getting in the way of business. At least for me it did. Personally, as an anointed superior, I had trouble acting the part with him. It was difficult to see the line between friendship and business. The tough conversations were even tougher and ultimately things didn’t get said. In the end, I was a wuss for not speaking up when speaking up was needed.

It’s been over a year since it has happened, and things still aren’t the same. I’m not sure they ever will be and I understand why. It truly blows. I love him like a brother and wish I could go back and do things differently. I miss him and the way things use to be.

If I could do things over again, I would absolutely still go into business with him. This time though, I would grow a pair and speak openly and honestly about issues well before it ever came to the decision that I had to make.

I hope someday I’ll get a chance to make it right.


  • I can understand, I am right now going through a similar thing with my friend/partner. Some times, my empathy, as a friend is mistaken for indecisiveness and/or meekness.

    Time will tell how this will work out.

  • I have found myself in similar situations and I can attest to the fact that it is a very very tough place to be in. Ideally I would like to be more human in such situations but can’t. The only answer which provides me relief when I am in such situations is this phrase from Bhagvat Gita

    “O Arjuna, listen, this tendency of yours to run away from action is not the answer to your dilemma and your problem. You must open your eyes, have an inner understanding and see clearly. It is not a question of action and inaction. The wise thing is to know that there is a third way, which is the right and proper way, and that alone is the solution and answer to your present situation. And that way is wisdom-filled action. ”

    I am not sure how others have handled it in past but this is the best I have found during my research. I would like to know how others feel about it.

  • Sadly I think we need to learn this at an early stage of business before we get things messed up. I also have been through this and its really sad but we just have to move on. Brilliant write up here

  • I’m staring at the screen in disbelief because our stories are shockingly similar. I thank you for sharing. Believe it or not reading this and knowing I am not alone has been therapeutic for me. Thank you!

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