An epic conversation with Harry Stebbings: My 1:1 on The 20 Minute VC (finally!)

Say it with me: IT’S ABOUT DAMN TIME!

Yes, that’s right, your eyes and ears aren’t deceiving you — Harry and I finally (fintally with a T, yall) got to sit down and talk with each other for his podcast, The 20 Minute VC, a pod that gets millions of downloads each month, and has been rocking and rolling for years now.

We have tried to make an interview work for what seems like years, but something always got in the way for one of us. You could say that timing is everything, though, because I think this episode really fires on all cylinders. I’m so excited for you to hear it. Check out the episode on Harry’s site, Apple, Spotify, or anywhere your favorite podcasts are found!

—

In our episode, we talk about…

1.) How I made my way from the airport floor to founding my own venture firm, Backstage Capital and writing a book, “It’s About Damn Time”?

2.) What’s my relationship to money and wealth? What are my thoughts around my desire to give away 90% of my wealth in my lifetime? How do I evaluate my own appetite for risk? How has that changed over time?

3.) From a strategic perspective, what are some core elements to my strategy that are not obvious? What are the main misconceptions that remain with regards to under-represented founders? What do I believe are the leading indicators when assessing founders today?

4.) What have been the biggest challenges in building my venture firm, Backstage? What have been the core breaking points in the scaling of people and strategy? How do I think about the relationship between brand vs reputation? What do I believe are the main misconceptions people have about me?

5.) How would I like to see the world of venture change over the next decade? What can LPs do to encourage more underrepresented founders are backed? How can this be measured? Who should be held accountable?

Let’s go!