How to stop being an ass***le

In 2019, I took an eye-opening walk during a 1x1 with Adonis V. He had joined Ampush as an intern from Berkeley in 2014, and quickly rose to leading 25% of the company.

As we strolled through SoMa in downtown San Francisco, we stopped at the light at 9th and Harrison. Adonis looked at me quizzically.

"Jesse, I want to ask you something,” he said.

“Last week, we talked about how performance with the Provide Commerce account was down, and that the relationship was at risk. What you responded with was no different from what you said during that same meeting 3 years ago, but I felt COMPLETELY different. I was inspired and felt supported walking out. I used to feel afraid and belittled. What changed?"

At once, I was both embarrassed and gratified. All my hard work in coaching and personal growth is paying off!” I thought.

But that thought quickly turned to, "Oh my God, was I such an ass****le back then?!"

I reflected on his question, stumped at first… But then it hit me.

"Adonis, I've become more interested in coaching you than getting the answer right. Or even, more specifically, I now get my motivation from helping you grow, rather than just focusing on the financial results of our business.”

What I realized in that moment was a game-changer. As Adonis pointed out, the actual words I responded with hadn’t changed over the years.

I was still addressing the same business problems with similar solutions.

The differences were in my intention and focus.

Previously, I had approached these conversations primarily concerned with being right and getting the best financial results.

Now, I realized I cared more about developing Adonis as a leader (though the financial results were still important).

This shift in my internal motivation, despite not noticing it until that moment, had completely transformed how Adonis experienced our interactions.

The same words delivered with a different intent created an entirely different emotional impact.

Where I placed my energy and focus (on coaching him versus being right about financial results) turned into countless subtle body movements, vocal inflections and sentence structures that communicated genuine support.

When I first heard people use this phrase, it sounded woo-woo and weird. But ask yourself this series of questions.

When you take a meeting with your team…

• Is your phone in one hand and are you constantly looking down at it?

• Is your mind on the previous meeting and how that initiative is going awry?

• Are you thinking about next week’s big client conversation and getting spooked?

• Are you judging the person presenting because they aren't delivering?

• Are you tired because you woke up late and have been reactive all day?

There's a line in a famous Sikh scripture:

And I think it’s really apt here! What's going through our minds drives how we show up; and how we show up as CEOs or leaders, impacts everything happening around us.

As I write this, I cringe thinking about our 2016 offsite. Our office manager did a "Jesse imitation."

She walked in the office, head buried in her phone, bumping into walls, not acknowledging anyone as she made her way to her desk.

No wonder people rated me a shitty CEO.

Also, for what it’s worth, I'm FAR from perfect here. I have bad days. Sometimes I pick up my phone during meetings — especially on Zoom.

I get distracted if I get bored in a conversation. (I hate Zoom!) I’m not saying this to make you feel bad or guilty, but to help you create awareness.

Ok, Jesse. You've convinced me that how I show up is important. How do I improve it?

Here are a few tips:

Of course, it always starts with awareness.

Notice how your body feels walking into a meeting. Are you happy? Sad? Are you feeling tightness in your chest? Is your mind racing? Or are you open? Excited? Curious?

Knowing where you are is the first step in choosing how you show up.

Noticing your body posture is often a hint to how you show up.

Are your arms crossed? Are you "stuck" in a position? Or are you freely moving with an openness?

I'll often be sitting in a meeting (especially a negative or tense one) and notice my body is closed off. My fists are clenched.

So I'll just stand up or shake it out, and my ENTIRE being SHIFTS.

Most meetings around Gateway X start with a brief pause. We breathe (I love 4x4 breathing). We may share one fact. We pause notifications and put the phones away.

If there is something on your mind you can't shake, share it with everyone. Seriously, try it.

Something like, "I've been arguing with my wife about X,” and watch as it quickly disappears from your mind.

In a meeting, if you notice you're losing presence, call it out! Then, reset.

Set an intention for important meetings.

I often ask, "What's a 10/10 in this conversation?" Or "How do you want me to show up in this meeting?" Answers could include: supportive, curious, skeptical, with ideas.

A little intention goes a LONG way. It creates focus and clarity in ways I've rarely seen.

For your own mindset, try this special trick Dave Kashen taught me.

Take 5 index cards and write single words on them like, "Inspiring,” "Loving” or "Helpful." Whatever you want.

Before beginning a meeting, flip through the cards and pick one. Silently commit to showing up that way, and watch how the meeting unfolds.

I'll write a whole email on this, but learning how to share your feelings in an "unarguable" way (i.e. a way that doesn't attack someone else) is a superpower.

My go-to phrases when sharing my feelings are, "I worry that…" "I fear that…" "What keeps me up at night is…"

This isn’t manipulation — it’s genuinely sharing a fear that’s running through my mind.

When I share openly, I can release those thoughts and get fully present to solve the problem, rather than allowing those thoughts to live in my head, causing me to lose presence or push the meeting a certain way, both of which impact how I show up.

People can feel when you're "leading them to water," and it rarely feels good. Candor leads to better outcomes.

During your next meeting with 4 or more people, I want you to try something.

Start it by saying, "Let’s all go around and say 1 thing we appreciate about each other, this project or anything else." Then, you start it off. Watch what happens.

I believe gratitude is one of the closest things to the "Divine" that humans can experience, and it instantly shifts our perspective.

I've talked about my journey with gratitude journaling, but the key thing to realize is: humans are hardwired to focus on the negative — to find the problems.

It's our survival instinct. Almost everyone walks into a meeting with a negative slant, even the bubbly people.

A brief, earnest moment of sharing gratitude can shift everyone.

Use this downloadable checklist to remind you to use these tips and see how your leadership changes.

So there you have it! Are these methods a silver bullet? Of course not. You will still have challenging interactions and tense meetings. That's business.

But they can be a powerful way to shift your company. And when practiced daily, they become culture, which is a huge long-term differentiator.

Take this email and during your next business day, pay attention to how you show up in every meeting and conversation.

Then, try these implementing these 5 tips and see how your day shifts and how your team performs.

You'll never be the same.

-jesse

PS Andrew & I are hosting meetups in our hometowns. The last time we hosted a meetup, people flew and drove in from other states. Come join us for a drink and conversation. RSVP to Austin here and St Louis here.

And if you know founders in either city, pass the invitation page to them.