Managing ego in the founder's journey (or as a leader) is a very delicate balance. It both is what makes us take great leaps, and is also what makes us ultimately give up.

This balance has been one that I've talked about with thousands of founders in my time in venture capital, to founding a healthcare company, to then shutting down companies, to even now having recently excited a company we started 6 years ago for $1B+.

I've distilled the best analogy I can for what I've come to learn about the role of ego in the founder's journey, or frankly any leader's journey as they pursue an ambitious goal. We will chat through:

1) what ego means?

2) why ego is important and where it can be debilitating

3) how we can tell when toxic ego is surfacing

4) questions that help us manage and fuel ego in a more productive way

I share reflections from my founder and VC journey interacting with 4,000+ CEOs and founders - some of whom have brought their companies public, and some of who have to sunset their company.

The solo episodes isn’t advice. It’s a weekly reflection that I want to remember and share in the pursuit of building a world where we all take that bet on ourselves, whatever it may be.

New episodes every two weeks — sometimes with guests I deeply admire, sometimes just honest thinking in progress.

“There is no such thing as risk-free greatness.”

When Arnold Schwarzenegger wrote this in support of Olympian Lindsey Vonn, it deeply resonated.

As someone who has lived both sides — venture capitalist and founder — I’ve seen firsthand that the people who build anything meaningful all share one thing in common: they are willing to enter the arena.

In this solo episode, I unpack:

• Why greatness is never risk-free

• The psychological warfare of leadership

• What separates spectators from builders

• And the mindset patterns I observed after meeting 4,000+ founders and CEOs

This episode is for first-time founders and first-time leaders leveling up into the next version of themselves.

New episodes every two weeks — sometimes with guests I deeply admire, sometimes just honest thinking in progress.

“If you assumed it was real, what would you do?”This question has quietly shaped every major chapter of my career since business school and from venture capital, to founding a healthcare company, to now writing my first novel.

I first learned it from a founder we invested in - the founder of Zola, the wedding registry company that reaches millions of couples - and it’s a question I keep coming back as I embark on an ambitious goal. In this solo episode, I reflect on:

1) Why “believing in yourself” is vague and why I prefer this question

2) How assuming something is real changes the quality of feedback you get

3) Why conviction is built through action, not affirmation

4) What it means to assume the identity you want next — founder, athlete, writer, creator, whatever

I share reflections from my founder and VC journey interacting with 4,000+ CEOs and founders - some of whom have brought their companies public, and some of who have to sunset their company.

The solo episodes isn’t advice. It’s a weekly reflection that I want to remember and share in the pursuit of building a world where we all take that bet on ourselves, whatever it may be.

New episodes every two weeks — sometimes with guests I deeply admire, sometimes just honest thinking in progress.