What does it mean to " shoot your shot"?

We hear this phrase all the time, and I LOVE it. I often say it to myself when I need to lean into something seemingly scary like during fundraising, or sending cold emails to industry titans.

The phrase "shoot your shot" has quietly shaped every major chapter of my career since business school and from venture capital, to founding a healthcare company, to recently selling a biotech company I started 6 years ago for $1.2B+, to most recently publishing my first book (which now one has become a bestseller).

But the issue I have with "shoot your shot" is that for as easy as it is to say to someone, there's a lot more emotion underneath it that needs to be overcome for someone to actually...shoot their shot.

So in this quick episode, I reflect on:

1) The history of "shooting your shot" and where that phrase first came from

2) The learnings from NBA players when they are actually in those "buzzer beater" moments and what they tell themselves as they quite literally..."shoot their shot"

3) Why the ability to shoot your shot is tied to first letting go of any expectations you might have

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 an honest, pretty unedited 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.