How I went from “can’t be trusted” to “bringing humanity to leaders”

A colleague at GX recently said this about me:

Let's back up 10 years.

How did I go from "The CEO can simply not be trusted" to "You add a layer of humanity I've never seen from other leaders."

Well, let me tell you. It wasn't by accident — nor was it easy. It's been the hardest work of my life, and the thing I'm probably most proud of in my life. 

Beyond work, it impacted every relationship in my life, including my wife, kids, family and friends.

Here's what I did:

"Everything has truth in it, so instead of asking IS it true or not, to learn/grow, always ask yourself: ‘How is what they're saying true?’" -Dave Kashen.

I'd love to tell you that as soon as bad Glassdoor reviews came in about, I stopped what I was doing and said, "How is it true that I can't be trusted?"

But I did not. Instead, I ignored the posts. Then, when they kept coming in, I dismissed them as a few bad apples. 

This all came to a head when Red Ventures was buying a stake in Ampush. 

As a part of deals like this, it's common for the buyer to require a "majority of the minority shareholders" to approve the deal. 

This isn't strictly required by law, but it massively limits the chances of annoying lawsuits.

One of our early employees was a shareholder whose dad caught wind that we needed his signature to close the deal, and he demanded we buy out all of his shares (instead of his pro-rata portion).

When we refused, he lobbied several other shareholders (all former employees) to hold out in order to get leverage over the deal. 

It was like something out of a TV show. Ultimately, one of the holdouts defected, and we closed the deal.

But I was stunned. It was the first (and only) time I ever cried during the Ampush journey. 

I couldn't understand why so many people would "turn" on me.

As I cried my sob story to Jon Oberlander (who replaced me as CEO), he lovingly pushed me: "You may want to start taking some responsibility for people’s lack of trust in you."

Again, I didn't do it immediately, but over the next few years, with the help of Nick Shah (my co-founder), Jon and Dave Kashen, I started getting more honest with myself and finally asked the question:

"How is it true that I'm not trustworthy?" It was scary, but it led to immense growth.

The TL;DR isn't that I'm some kind of shady criminal.

But I hurt trust by embellishing too often, not being organized enough, and, at times, being persuasive to the point of manipulation. 

These were all things I was doing to "protect" myself which, ultimately, didn't serve me. 

As I shined light on these behaviors, I started evolving.

I've written a lot about Dave Kashen and my coaching journey. 

What you may not know (and Dave still teases me about this) is that I met Dave five years before I worked with him!

When young entrepreneurs ask me about the top things I would have done differently, this always tops the list: I wish I had gotten a coach earlier. 

I was young, running a bootstrapped company, and the idea of paying $5K a month sounded crazy!

It turns out, it’s been the best money I've ever spent.

If you want to see what it’s like to work with Dave, this YouTube video of us will give you a taste of his impact.

There are so many things a coach does, but the big one in this transformation was helping me develop self-awareness, SPECIFICALLY when I was feeling fear.

And then when I felt fear, choosing not to lead in that way.

Like lots of leaders, my "heart" underneath everything was good, and many people saw that. 

But what good is it if I'm constantly disconnected from my heart and letting fear lead me?

When most people feel fear or threat, they try to control or manipulate, withhold information, or they yell or criticize, or all the other behaviors I'm sure every human has done at some point when feeling fear. 

Learning to see myself in that state and then pause, changed my life.

It wasn't without awkward moments. I remember about a year post-coaching, the team reporting revenue was down for two clients, one client was a churn risk.

Old Jesse would have either lectured and reprimanded OR jumped into problem-solving mode. 

New Jesse paused and said, "I notice my chest got tight and I am feeling fear."

Everyone kinda looked around and laughed nervously. 

But that little bit of work and vulnerability meant I wasn't letting the fear win — I was able to be aware of it and then chose how I showed up. 

In that case, I just said, "So what's our plan?" 

The team shared a game plan and I agreed with 80% of it (old me would have mansplained a plan to them they already had!), and we went off on our way.

Beyond Dave, I was supported by an amazing group of executives — people who had tons of support, loyalty and confidence in me, but were the OPPOSITE of sycophants.

No, they would tell me when exactly I was f*#king things up and help make me better. That helped immensely.

I remember this like it was yesterday. It was 2019, and Dave had returned from some kind of inspirational conference. 

We'd been working together for almost two years. As I built up more awareness of my default fear mode and chose not to be reactive, another obvious question came up:

If fear isn't what motivates me, then what is?

The answer was purpose. When I heard that, I went into a tailspin: "I must FIND my purpose!

“I will brainstorm and catalog and think of all the great things I can live for and then choose one and that shall be my purpose."

Dave had a different take.

"Purpose isn't another brass ring. It’s not ‘out there’ and something you need to go achieve. No, it already lives inside you. It already shows up when you walk in the room. You live it — you just don't know it yet."

Then he asked me a life-changing question, and I recommend you stop now and write down your answer to this question:

"What's the one thing you can't NOT do?"

Weird question. But the idea is… what's something that is just such a part of you?

If all the people you knew got together in a room and had to agree that "This is SO Jesse," what would they say?

I thought for a few minutes and then wrote: "Help others learn and grow to be the best versions of themselves."

My employees, friends from high school, and family would all agree with that statement.

I tucked it away and revisited it every week. As I did so, the fire of it grew inside me.

Later I added "via business" to the end, because that's my canvas of choice.

But my purpose had always been there… Adriane (CEO of GrowthAssistant) tells a story about me from when we were 16.

She told me where she wanted to go to college, and I simply replied, "You can do better."

And that motivated her to explore and go to a much better school than her original plan.

That's my “why.” That's why I write this newsletter, and why I do most of the things I do!

With that clarity, I had something to keep me from fear and instead bring my heart to others.

So there you have it.

Now, one last thing: do I have no fear? Do I walk around like some enlightened guru? Hell no!!

Much to my frustration, this is not a binary switch. 

No, it’s a gradient. A daily one. An hourly one. Fear still takes over all the time. I get worried about myself. I get triggered. 

And, other times, I can show up with my heart open and the humanity my colleague noted.

I would say I went from 75% fear and 25% love to the other way around, and that is awesome progress.

And it comes from presence day by day, minute by minute. It's been the journey of a lifetime, and I'm still in the middle of it!

Have a great week,

jesse