How Jesse Pujji Rewired His Mind (and Built Multiple 8-Figure Companies)

What happens when you build everything you ever wanted… and still feel empty?

For Jesse Pujji, that moment came after bootstrapping Ampush to a multi-eight-figure exit and realizing that money and titles weren’t enough.

So he stepped back, did the inner work, and started Gateway X, a venture studio built around one radical idea: you can scale businesses and stay human.

Jesse and I met as college kids at Wharton 20+ years ago. He was the calm, wise one. Let’s just say I was… not that. That’s why this conversation felt like a full circle moment for me.

In this conversation, Jesse and I talk about what happens behind the curtain of “success” and how fear, ego, and self-awareness shape everything from our leadership style to our happiness.

You’ll hear:

• Why fear and extrinsic motivation (money, titles, status) will get you far but can’t take you all the way.

• The 5 motivators that drive every founder (and how to choose yours consciously).

• How to find your “one thing you can’t NOT do.”

• Why Jesse left a $1M offer on the table to start his company.

• How to turn anxiety into presence: in real time, even in a meeting.

• The difference between treating people like employees vs. adults.

• What it means to run your business as a spiritual practice.

• The moment humility became Jesse’s superpower.

This episode is for for anyone building something big and trying to stay grounded while they do it.⏱️ TIMESTAMPS

00:00 — How Healey and Jesse met at Wharton (and the TA story that started it all)

03:30 — Why Jesse left Wall Street to build a company from scratch

06:00 — The crash after the win: what happens when external success stops working

07:30 — The 5 motivators that drive all human behavior (and how to choose your fuel)

10:00 — When money stopped motivating and what filled the gap

11:50 — “What’s the one thing you can’t not do?” Finding purpose through practice

13:20 — From purpose to play: how to live in your “zone of genius”

18:00 — The decision to leave a $1M job offer and follow intuition

25:30 — “Fear is excitement without breath.” How to reframe fear as energy

27:00 — Aliveness as the compass: how to know you’re on your path

30:00 — Work as a spiritual pursuit (and how to turn frustration into curiosity)

33:00 — Mirrors, ego, and the parts of ourselves we don’t want to see

38:00 — The moment Jesse said “I feel scared” in a meeting (and how it changed the room)

42:00 — Why presence is contagious and awareness builds trust

44:30 — Treating people like adults (and why “loving candor” works better than control)

47:00 — How humility became Jesse’s leadership advantage

50:00 — What he wishes someone told him earlier about money, fear, and fulfillment

52:30 — Where to find Jesse today and what he’s building next

—

🎧 Listen now to Don’t Be a Jerk wherever you get your podcasts. Follow for more conversations on leadership, kindness, and the inner work of building something that lasts.

IG: @healeycypher | @dontbeajerkpodcast

LinkedIn: Healey Cypher