# Gregg Schoenberg | Do You Have More Than One Way To Win?

By: Justin Abrams
Published: 2026-09-24

Every piece of career advice you learned was written before November 30, 2022.

That is the day ChatGPT launched. Gregg Schoenberg's position is that most of the advice conceived before it should go in a drawer, and the biggest casualty is the one everybody repeated for generations. Focus. Do one thing really well.

In this episode of Forward to Extraordinary, Justin Abrams sits down with Gregg Schoenberg, executive coach and founder of Wescott Inc. Capitol Hill aide, corporate lobbyist, then thirteen years in investment banking running U.S. Capital Markets at Natixis. He built and sold a fintech media company and spent years as a TechCrunch fintech contributor.

Then Justin hands him the whole business and asks him to grade it live on air.

We get into:

- The portfolio career, borrowed straight from Wall Street risk parity
- Convexity, and why you need a couple of bets that are life changing if they hit
- Why correlation of one ruins a portfolio, and what a counter cyclical activity looks like
- Justin's actual allocation broken down live: the agency, the show, angel investing, LIT
- Why a media house is a billion dollar opportunity and a service business is not
- The one question Gregg asks before writing an angel check
- Why the best leads he ever got came from investments where he lost every dollar
- Where entrepreneurs are supposed to find mentorship when nobody assigns it to them

Connect with Gregg:
LinkedIn: https://www.linkedin.com/in/greggschoenberg/

Website: https://greggschoenberg.com/
https://provokingtransformation.com/

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