What Is It Really Like To Be An Entrepreneur?

Confident surfer riding the barrel of documents wave

I remember talking to my Dad years ago when he was running his company. My Dad used to talk about being “knocked around.”

I would say to my Dad, “It doesn’t sound like much fun. Why would you want to do this?”

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“Because Brett, I’m having the time of my life.”

“It doesn’t sound like you are,” I answered.

Fast forward many years later to when I was an Entrepreneur in Residence with a VC fund in San Francisco.

I was talking with my Dad about the work I was doing getting my company off the ground. One thing I remember saying (naively) to my Dad was, “I think I should only be CEO for ten years maximum. Then someone else should take over.”

My Dad laughed and said, “You’ll get knocked around like I did, but you’ll never want to quit.

“Trust me.”

My Dad’s comment stuck with me as I got my company off the ground. Sure enough, I was getting knocked around on a regular basis too.

There were always issues that seemed to have nothing to do with the fun stuff of building a company:

There was the coup two of my cofounders tried to stage right before we closed our funding. “Randy” and “Ken” demanded we have an “Office of the President” where key issues would be agreed upon by the three of us.


Are we having fun yet?


Then there was the time I was driving back from the Courtside Club in Los Gatos while we were closing our initial funding. It was a driving rainstorm.

The rain was coming down in sheets. But at least 85 was deserted.

Suddenly, the phone rang. It was our new investor “Raul”.

My heart rate went up another 50 beats per minute.

“What does he want now?” I said to myself.

I debated whether to answer the call for a couple of rings. Then on ring number four I decided against my better instincts to answer the call.

“Hello, this is Brett,” I said.

“Brett, what is this craziness about you withholding some previous patents!”

Raul was screaming at me.

The rain kept coming down. It seemed to be getting even harder.

“I’ve about had it with you and your lawyer!”

I thought I heard thunder in the background.

What was he talking about, I wondered? I still had 10 minutes of driving through this crazy rain before I got home.

And I didn’t feel like dying today. So, I punted.

“I’ll look into it Raul,” I said as calmly as I could. My heart felt like it was going to explode out of my chest.

The rain kept coming down.

“You better do that today because I’ve had it!”

Click. The line went dead.

Another shitstorm. It was the third one this week, and we hadn’t even gone into operating mode yet.

What would life be like with Raul then?

The rain kept coming down even harder. I just wanted to get home safely.

I always had this vision of Raul coming home after work and sharing how his day went with his wife. He’d be relaxing having a glass of wine.

His wife would ask, “Raul, how was your day?”

“Oh it was a good day.

“You know that deal I’m closing? It’s going really well.

“I’m pushing the CEO to the wall. He’s going to agree with every concession I’ve asked for.”

Then Raul would smile contentedly and he would have another glass of wine.

So was I getting knocked around like my Dad said? You bet:

  • I had the cofounders knocking me around.
  • I had Raul knocking me around.
  • And just like my Dad predicted, I was having the time of my life.

How can it be that you’re having the time of your life when you’re getting knocked around all the time?


  • Because the company, this thing you’ve been dreaming about doing, is your baby, and…
  • If getting knocked around a little bit was the price you had to pay, then so be it, so…
  • Yes, you remember the crap you have put up with because the crap put your dream in danger of being realized, but…
  • It was true bliss in between those danger points because…

You get to implement your dream, your vision, and your company the EXACT way you want.


Seriously, what could be better then that?

Um, nothing.


Starting and building a company was a dream come true.


And nothing was going to keep me from realizing and enjoying my dream. Not Randy, not Ken, and definitely not Raul.


I loved every second of building my company.


The euphoria of getting investors to give you millions of dollars based on a few meetings was mind-blowing. It was like having a baby.

I’ll never forget where I was (in my kitchen) when the initial funding was wired into our bank account.

Then selling an incredibly talented group of people on the vision for your company. And then watching them quit their jobs to join your fledgling venture.


What a rush!

Then watching this team of unbelievably talented people execute the plan you’ve developed with them is an indescribable feeling. And then watching this group of people of incredibly talented people come develop truly ground breaking ideas is well…

Immense pride and satisfaction is the best way to describe it.


Then watching customers actually buy your products! And then watching customers buy more and more of your products week after week, and month after month!

It was a dream come true!


Then, when we were out of money and we had to go to minimum wage to keep the company alive, and the whole team applauded when you told them! Who could have predicted that reaction?!

I had to hold back my tears.


That day remains the best day of my career.


My Dad was a type 2 diabetic. He took really good care of himself and looked great.

My Dad had a stroke right before Avery’s second birthday. I flew down to LA to visit him in the hospital.

The doctor said the stroke was a “mini stroke” or TIA (Transient Ischemic Attack). I Googled it, and supposedly all the symptoms were supposed to quickly go away in a few hours.

My Dad’s speech was slurred. But mentally, he seemed to be all there.

I was optimistic he would make a full recovery.

It was a late Sunday night when the phone rang. My Mom was on the line.

“Brett…” I knew instantly that my Dad was dead. He was 75 years old.

He had a massive stroke 18 days after the first “mini stroke.” He died instantly.

My only regret as an entrepreneur is that my Dad never got to see me live out my dream. He would have loved seeing me getting knocked around.


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