When I almost quit…

“I Quit.”

After 7 years of running hard every day to build my dream company, I couldn’t believe those words were coming out of my mouth. It was 2017 and I was staring at my best friend and co-founder, Nick Shah.

I had been out for a month on my second paternity leave and this was supposed to be a meeting for me to “ramp back up.”

The problem: We had charged hard on Ampush for 5 years from 2010-2015. My wife never saw me. The business was always on my mind.

It was a roller coaster of ups and downs. In 2012, we divested our “original” business to focus on the Facebook ads business. We knew Facebook was going to be the future and went all in. Our “plan”: let's work like crazy for 3 years and grow the business, then flip it for a massive price.

We worked like crazy. 80-hour weeks.

The business grew from $3M to nearly $30M in 3 years (net revenue).

And so we marched out to market ready for a 9-figure check.

The only problem: ad tech valuations had tanked.

We ended up with some mid- to high-8-figure offers and I was… distraught. I had lost all perspective, was completely disappointed, and didn’t know what to do.

Without properly processing all of this, we chose our favorite suitor (Red Ventures) and we struck a very weird deal. They would buy a minority stake in our business for $15M (all secondary) which gave us meaningful personal liquidity (I was 31).

But we’d give them a 2-year option to buy the rest of the business for… 9 figures.

The day the deal closed I’ve described as the MOST disappointing day of my life. Since I was 15, I had worked my ass off to get into a great college, top companies, and then build and exit a company to make millions.

I saw the money in my account but felt nothing. I was waiting for wings to sprout or superhuman strength but neither came. I was the same person with a bank account. That was very hard.

Nonetheless, I carried on. As a part of the deal, we agreed to change the strategy to fewer clients with deeper relationships.

Fast forward to 2017, we learned a ton from them but the strategy wasn’t exactly working, certainly not in the time we’d hoped. They continued to be great partners but told us: we will not be buying you.

That began with me doing a multi-month spiral of what I told my wife were “low mojo” days. Really, I was completely burnt out, disappointed, and had lost motivation.

After I told Nick I quit, I spoke with the founder of Red Ventures. His advice was simple and caring:

I liked the sound of that and figured there wasn’t much downside from here.

After meeting a handful of coaches, Nick (my Ampush co-founder) and I selected Dave Kashen.

Within ~3 years, Ampush’s culture and engagement scores were up 50%, the business had grown profits steadily and I was not experiencing the classic “ups and downs” anymore. I felt calm and still as ambitious as ever.

I could probably write a multi-month series on my journey with coaching but I’ll try to summarize the big stuff.

The first wisdom Dave taught me (coming from The Conscious Leadership Group or CLG) was “Types of Motivators.” When you read them, see if you can spot your motivator.

The 5 motivators::

• Fear

• Extrinsic (money, titles, status)

• Intrinsic (beating your own score)

• Play/Genius (something that is just fun/enjoyable that naturally brings you energy)

• Empathy/Love (helping other people/the human experience).

We all use all of these motivators all the time. Most people tend to use 1 or 2 more than others. And MOST people use fear.

I was one of those people. I was afraid Ampush wouldn’t succeed, afraid I wouldn't make the most of my gifts, that I would disappoint my family, that leaving finance was a bad call, etc. Fear reigned supreme. It got me to make tough phone calls, work 80-hour weeks, and keep driving myself and others to excellence.

BTW, none of these motivators are good or bad, they just have trade-offs. Fear is HIGHLY effective. If I put a gun to your head, you’ll run faster than you ever have. But fear tends to leave a negative residue on you and your team.

PLUS it's a non-renewable resource. (once you outrun me, you walk). It's not pleasant. This explains why entrepreneurs often have success and then move their goalposts. THEY NEED MORE FEAR.

Play/Genius and Love are evergreen motivators. Doing them more makes you want to do them more. They are renewable resources and tend to also be pleasant and enjoyable! And they seem harder to figure out and come by. Humans are hardwired to be in fear (it's a survival mechanism).

For the first year or so of coaching, Dave was like Mr. Miyagi. But instead of saying “wax on, wax off” he would say: “Just notice” NOTICE WHAT?! I’d scream.

Notice your body and sensations. Notice your thoughts. Notice emotions. Building this self-awareness is the first and probably the most critical step in my coaching journey.

Prior to this, I had no idea when I was frustrated or feeling worried. I was just constantly reactive.

After doing this for a while, I started to build self-awareness IN THE MOMENT. I walk into a meeting where I hear a big client is firing us and I notice my CHEST gets tight. Oof, I feel scared. Rather than reacting which usually involved blaming someone on the team or anxiously coming up with a “plan” to save the client, I would breathe or write down my fears. My head would then be clear enough to MAKE A CHOICE on how to respond.

That’s why this practice is called Conscious Leadership - it's intended to get us away from reacting and to responding. When we're reacting, we're operating on autopilot, like a hot-headed driver responding impulsively in traffic without considering the consequences. When we're responding you're actively engaging and choosing your actions.

As my awareness built (and continues to build), there was another helpful framework from Conscious Leadership: “Context vs Content”

They posit that what you actually do –digital marketer, founder, surgeon, product management – is irrelevant to your motivation.

The only thing that matters is which of the 5 motivators above you are using.

At first, I COMPLETELY disagreed with this. I fought it tooth and nail. I told Dave: “dude I'm a smart guy, I’ve been doing digital marketing for 7 years… I’m just bored of it!”

He came back: “I think you were using fear to motivate yourself and now you made millions and have a successful business so you don’t feel fear anymore… and you are lost because of it.”

With time and lots of proof points, I slowly did a 180 on this point. Here’s an example that hit home for me, which company would you rather work for?

A) “Cancer curing startup” - BUT the founder is an egomaniac, only cares about being on magazine covers and pushes people with fear to hit deadlines.

B) “Boring insurance brokerage” - BUT the founder genuinely cares about serving his customers, looks out for employees' well-being, believes insurance is the key to human peace of mind and tap dances to work..

There were other impactful things I did on my journey. Two most noteworthy were:

1. Gratitude journal - I learned that humans naturally slant negative as a survival tactic. So writing what we're grateful for counteracts that negativity, esp if it's specific. Without it, you will wake up negative every day. I use the 5 minute journal app every morning which has a great guided interface.

2. Meditation - I learned that the point of meditation isn’t to stop having thoughts. It’s to HAVE thoughts and not REACT to them. When I sit in the morning, I’d guess I have 100+ thoughts. An email I didn’t respond to, a weird comment someone made, how I wish I appreciated my wife more. And I continue to sit and let those thoughts pass.

There were weeks and years of practicing awareness, noticing my motivators, and choosing how to respond. Setbacks. Sometimes I questioned all this and considered it BS, maybe you're thinking some of that as you read this.

After a couple of years though, I was definitely in it and ready for the next level.

The idea was now that I was aware and could accept myself when I felt fear etc… Could I more regularly CHOOSE to be motivated by genius/play and love, instead of fear?

This involved two different, important exercises:

1) Figuring out my Genius - Genius is like the Japanese concept of Ikigai, which means "reason for being." You find what you are good at, what you love and what brings you energy. It’s often not known to people because it's like asking a fish about their swimming skills. Dave helped me reflect on my days, do energy audits, and ask others to really key in on my genius areas. I discovered mine are:

1. Coaching/teaching people

2. Selling/building relationships

3. “Entrepreneurial problem solving”

4. And several others…

2) Figuring out my “WHY” or the love I wanted to bring into the world for others.

To do this: Dave asked me a question at some point in 2019:

The theory here is that somewhere deep inside, you know your WHY, your purpose, you already carry it around with you. But it's important to name it and know it so you can do it more intentionally. So you ask yourself that question, write down what comes to mind and look at it again every few weeks. Does it still resonate? Does it burn like a fire? Or does it need changing. Keep doing it till you find something that takes over.

For me, my why is: Helping others learn and grow to be the best versions of themselves. That’s what motivates me beyond money, titles and anything else. How many people can I help grow? And my “tool” to do it is entrepreneurship.

That was a “this is the first day of the rest of your life” moment for me.

During this coaching phase, Ampush’s culture and business started to improve by leaps and bounds. Our “culture and engagement” scores were up 50% over 2 years. And profitability was steadily growing. Three years after I first wanted to quit, the company was in a good place and I could move on, but move from love, not fear

And the seeds of my genius led me to start Gateway X, my startup studio, so that I could spend every day coaching and teaching entrepreneurs + starting companies. And why I spend hours each week writing this newsletter. I’ve experienced peace and success beyond what I could have ever dreamed. And feel like I’m just getting started.

Is it a straight line? HELL NO. Do I still have meetings, days, etc where I react from fear? DEFINITELY. But the improvement and journey have been astounding.

At New Year's dinner, my wife told me the best thing that happened to HER this year was me investing in coaching. I received a beautiful note from one of my new CEO partners thanking me for the positive impact I was having. I get emails from you guys constantly positively affirming my genius. It really is amazing and I am so grateful.

I could share much much more about my journey but I’ll end it here with a story:

Adonis who worked with me for 7 years (pre and post-coaching) took a walk with me in 2019. He shared the biggest compliment with me ever. He said: “When something is going wrong now, you don't SAY anything different. You dig in, look at numbers, break it down. But I FEEL so different. I used to feel belittled and nervous. Now I leave feeling supported, empowered, and inspired.”

Work on yourself. It’s the absolute best investment you can make.

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Jesse

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PS What's your experience with coaching? Or do you need help working with a coach? Hit reply and tell me.