How To Build A Co-Founder Relationship That Lasts The Courageous Leaders podcast

How to Build a Co-Founder Relationship That Lasts

11d ago 51:46

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What happens when two unlikely co-founders challenge everything about the venture capital world?

In this episode of The Courageous Leaders Podcast, I sit down with Check Warner and Matt Penneycard, the duo behind Ada Ventures. They open up about money, stress, parenthood, relentless rejection and what it takes to build a business from nothing but trust and audacity.

If you’ve ever wondered how to start a company with zero roadmap, navigate co-founder friction, or fundraise against the odds this one’s for you.
We Cover:
01:40 – Check’s bold career pivot into VC with no finance background

04:46 – Matt’s courageous leap despite the financial and family strain

06:18 – Why Check didn’t believe Matt was “real” (and how that changed everything)

08:40 – Equal partnership: how they split everything 50/50 from day one

11:54 – Building Ada Ventures with no salary, no certainty, just vision

13:13 – How trust and shared risk carried them through tough times

15:25 – The first moment of friction (and the awkward feedback conversation)

18:35 – Leading with inclusivity, especially when no one else was doing this

29:47 – Did they ever think about quitting? Yes. Here’s how they didn’t.

32:10 – The viral “privilege” article and why Check had to speak up
Don’t miss out on this powerful episode.

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Chapters

1. How to Build a Co-Founder Relationship That Lasts (00:00:00)

2. Check’s bold career pivot into VC with no finance background (00:01:40)

3. Matt’s courageous leap despite the financial and family strain (00:04:46)

4. Why Check didn’t believe Matt was “real” (and how that changed everything) (00:06:18)

5. Equal partnership: how they split everything 50/50 from day one (00:08:40)

6. Building Ada Ventures with no salary, no certainty, just vision (00:11:54)

7. How trust and shared risk carried them through tough times (00:13:13)

8. The first moment of friction (and the awkward feedback conversation) (00:15:25)

9. Leading with inclusivity, especially when no one else was doing this (00:18:35)

10. Did they ever think about quitting? Yes. Here’s how they didn’t. (00:29:47)

11. The viral “privilege” article and why Check had to speak up (00:32:10)

191 episodes