I told my co-founder, “I want to quit.”

Seven years into Ampush, I stared at my co-founder and said the words I’d been thinking for a really long time, ”F*ck this. I want to quit.”

My second daughter had just been born. Before that, I was coming into the office late and leaving early. I wasn’t paying attention in meetings. I was just burnt out.

So I called Rick — an investor who’d given me 15 million bucks and told me to “do whatever I want with it.”

“I’m in a rut,” I told him.

He laughed. “Jesse, you are the luckiest motherf*cker I’ve ever met. You’ve got two beautiful children. You’re a successful entrepreneur. You call your own shots.”

Then he said something that shifted my brain, “It’s probably time for you to do some inner work.”

We lie to ourselves as entrepreneurs.

Ask anyone why they became an entrepreneur and they’ll say one of these three things:

1. Money (”I’m gonna be rich.”)

2. Freedom (”I want to call my own shots.”)

3. Impact (“I’m gonna change the world.”)

Those are all lies.

Well, sort of.

There’s something much more powerful that goes on in entrepreneurship. And that is that the greatest gift entrepreneurship gives you is the ability to meet the best version of yourself.

As my coach recently texted me, “Entrepreneurship is the ultimate personal growth vehicle.”

It pulls out all your patterns, insecurities and bullshit. Then it gives you the opportunity to transcend them.

Today I want to share three lessons from my own journey, where entrepreneurship forced me to grow.

Rick told me to hire a coach. So I did. (By the way, it’s something I highly recommend.)

The coach sat with me, listened in on my meetings and met my executive team. I asked him, “So, what have you learned? How do I become a better leader?”

He said, “Stop using fear to motivate.”

I was confused. “Fear?! I’m Mr. Happy! What are you talking about?”

He said, “Jesse, I watched you for a couple days. Do you know how many times you use the words ‘should,’ ‘have to,’ ‘must’ and ‘need?’ Are those inspiring words? Do you feel inspired when someone tells you that you should grow your business or you need to do a reorg?”

I realized he was right.

“Well, those are the words you say to your team every day,” he continued.

And so we started playing with other words I could use. What if instead of “should,” I said “want to?”

Over the course of a year, I changed a lot of the language I used — with myself, my team and life in general.

The language you use matters. Stop using fear to motivate yourself and your team.

Uber was our biggest client for years. They spent over $100 million annually with us, so they paid us nearly $10 million in fees a year.

One day, we got a call. “We’ve loved everything you’ve done for us, but we’re a big company now. We don’t need you anymore. We’re taking the business in-house.”

They were nearly 20% of our business.

I got scared. And I did what scared leaders do: I blamed people.

I went to the account manager, “How could you miss this?”

I got everyone together and told them that there was no way we were going to lose this business.

Someone tried to speak up. I said, “No, get the slides. We’re gonna do this. We’re gonna work all weekend and make sure this happens.”

Days later, I looked at the deck, “This is terrible, guys. Don’t you care about this?”

We presented to Uber. They said, “Great presentation. We’re not interested.” Half the team quit.

Fast forward a few years.

A big movie studio was now our largest client. Same thing happened — except worse. We found out through a fat-fingered email from a Facebook rep that they were taking the business in-house.

It sucked.

But I got the team together, and I was a bit older and a bit more mature. I didn’t yell. I didn’t blame. I just said, “Let’s put together this renewal. We’re going to win this.”

The same thing happened. A really crappy deck came together.

But this time, I had learned a few things from my coach. I looked around the room and asked, “You guys are really angry right now, aren’t you?”

Someone on the team said, “Yes! We’ve been working our asses off for this client for three years, and they didn’t have the courtesy to tell us they wanted to take the business in-house.”

So I stopped everything.

“Let’s feel our feelings,” I said. “Everyone’s safe in this room. No one’s going to get in trouble. We’re going to spend as much time as it takes and just say whatever you want about the client and the situation.”

We went around the room. People got real nasty. But they let their anger and frustration out.

The next morning, everyone came in. I asked, “Do you guys want to try to renew this business? You don’t have to if it feels like it’s too far gone.”

They said, “No, of course we want to try.”

And so this time, we worked hard, but not out of resentment.

We presented it. The client said, “Yes.” Not fully, but they kept a lot of business with us.

Here’s what I learned: As a man, especially as a man of Indian descent, feelings were not something that came into my life a lot. We didn’t talk about them at the dinner table.

But learning to identify and feel them made me a better version of myself. A better leader.

Your startup shows you opportunities to feel your feelings multiple times a day — it’s about whether or not you’re willing to listen. I would encourage you to feel your feelings and lead your team so they do the same.

I had a longtime executive. Good guy. Liked me a lot.

One time, he sat me down and gave me some feedback, “I would trust you a lot more if you were more organized.”

Ouch, that hurt.

Here’s the thing: I am disorganized.

And yet, for years, I controlled compensation. I managed offer letters. I did all these things that a really organized person should do.

But what my exec meant was that I’d make promises and forget. I’d say I’d be somewhere at a certain time and wouldn’t show up on time.

Every time I was disorganized, every time I was late to a meeting, every time I missed an event, I lost trust.

That’s where my third lesson comes in: Identify and live in your Zone of Genius.

When I started Gateway X (my second company), I quickly hired a COO. I don’t touch offer letters anymore. I don’t touch compensation. There’s a whole set of things I just avoid.

Why? Because it gives me time to do what I’m great at:

• Inspiring people

• Solving challenging problems

• Working on marketing and sales

A lot of entrepreneurs hear the lie that “you gotta do everything.” You gotta systemize. You gotta do sales. You gotta mop the floor. That’s not true. And if you try, not only will your startup struggle, you’ll lose your energy.

You’ll be like me after seven years, saying, “I want to quit.”

Here’s the framework:

• Zone of Incompetence: Things you can’t do (for me: drawing)

• Zone of Competence: Things you can do fine (for me: driving)

• Zone of Excellence: Things you’re great at but drain you (for me: financial analysis)

• Zone of Genius: Things that bring you energy (for me: inspiring people, solving problems)

But here’s the thing I’m most passionate about when it comes to entrepreneurship: How do we use it to uplift ourselves?

Once you start uplifting yourself, you’ll uplift everyone around you.

The money, status, fame, changing the world — all those things can happen as byproducts. But I think it starts with a deep desire to grow yourself personally and better yourself every day.

jesse

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