How to Build a Co-Founder Relationship That Lasts

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

• 1:40 Check’s bold career pivot into VC with no finance background
• 4:46 Matt’s courageous leap despite the financial and family strain
• 6:18 Why Check didn’t believe Matt was “real” (and how that changed everything)
• 8:40 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