Automotive Ventures didn’t start as a venture fund. It started as two operators trying to figure out how to help founders.

In this first episode of Greenfield, Automotive Ventures General Partner Steve Greenfield and Venture Principle Justin Charbonneau unpack the unlikely path that led to building one of the most active seed-stage investment firms in mobility. From quitting stable corporate jobs and surviving failed startups to launching a venture fund in the middle of the COVID shutdown, they share the real story behind how Automotive Ventures came together.

Along the way, they break down how venture capital actually works, why most startups fail, what red flags they look for when evaluating founders, and why the best entrepreneurs don’t need capital—they choose their investors. After reviewing thousands of startups and investing in more than 55 companies across three funds, Steve and Justin reveal the mindset, pattern recognition, and founder traits that drive the biggest outcomes in mobility.

Takeaways:

0:00 Intro

0:40 Justin on the long road to entrepreneurship

4:31 The coffee meeting that triggered a resignation

5:46 Telling his parents after quitting in week one

8:20 Running out of runway and finding startup life

10:20 Building a startup in the wine industry

13:33 What failed founders learn that others miss

15:55 Winding down a startup in March 2020

18:15 From angel network research to launching a fund

21:34 Steve’s own founder journey and corporate reset

27:57 The $5,000 angel bet that changed everything

36:08 The karma bank and how Automotive Ventures helps founders

45:32 Red flags, return math, and why stage matters

Connect with Steve Greenfield at https://www.linkedin.com/in/stevegreenfield416/

Connect with Justin Charbonneau at https://www.linkedin.com/in/justincharbonneau/

Learn more about Automotive Ventures at https://www.automotiveventures.com