Raising and deploying capital can be one of the most defining moments in the life of any company.
To explore what really separates the great capital allocators from the rest, I spent over five hours in recorded conversations with five iconic leaders and investors. These aren’t just big industry names — they’re people I’ve had the privilege of working alongside for years. That trust opened the door for candid, behind-the-scenes conversations you won’t hear anywhere else.
Each guest was interviewed individually, and those full conversations will be released as bonus episodes. But in this three-part mini-series, we’ve woven those insights together — with Spencer and me in the studio reacting to clips — to reveal the patterns, decisions, and principles that define exceptional capital strategy.
In this episode, you’ll hear the full interview with:Mitchell Green — founder and Managing Partner of Lead Edge Capital, the global growth equity firm behind companies like Alibaba, Spotify, Asana, and Toast. Mitchell shares how Lead Edge built its unique investor network, what he looks for in world-class founders, and how great capital partners create value far beyond the check. Lead Edge was recently named the top-ranked growth equity firm by PitchBook.
Subscribe to catch the rest of the series and hear from other iconic leaders. Drop your biggest insight from Mitchell's story in the comments below.
Raising and deploying capital can be one of the most defining moments in the life of any company.
To explore what really separates the great capital allocators from the rest, I spent over five hours in recorded conversations with five iconic leaders and investors. These aren’t just big industry names — they’re people I’ve had the privilege of working alongside for years. That trust opened the door for candid, behind-the-scenes conversations you won’t hear anywhere else.
Each guest was interviewed individually, and those full conversations will be released as bonus episodes. But in this three-part mini-series, we’ve woven those insights together — with Spencer and me in the studio reacting to clips — to reveal the patterns, decisions, and principles that define exceptional capital strategy.
In this episode, you’ll hear the full interview with:
Julie Maples — founder of FYRFLY Venture Partners and longtime early-stage investor who’s partnered with dozens of founders at the intersection of enterprise software, data, and AI. Julie brings decades of perspective on what it takes to build enduring companies — and the investor-founder relationships that make it possible. Julie also has helped The V Foundation raise over $100M for cancer research as a valued board member.
Subscribe to catch the rest of the series and hear from other iconic leaders. Drop your biggest insight from Julie's story in the comments below.
Raising and deploying capital can be one of the most defining moments in the life of any company.
To explore what really separates the great capital allocators from the rest, I spent over five hours in recorded conversations with five iconic leaders and investors. These aren’t just big industry names — they’re people I’ve had the privilege of working alongside for years. That trust opened the door for candid, behind-the-scenes conversations you won’t hear anywhere else.
Each guest was interviewed individually, and those full conversations will be released as bonus episodes. But in this three-part mini-series, we’ve woven those insights together — with Spencer and me in the studio reacting to clips — to reveal the patterns, decisions, and principles that define exceptional capital strategy.
In this episode, you’ll hear the full interview with:
Gregg Kaplan — founder and former CEO of Redbox, former President/COO of Coinstar, and now CEO at Dentologie, where he's raised over $50M to date.
Subscribe to catch the rest of the series and hear from other iconic leaders. Drop your biggest insight from Gregg's story in the comments below.
Raising and deploying capital can be one of the most defining moments in the life of any company.
To explore what really separates the great capital allocators from the rest, I spent over five hours in recorded conversations with five iconic leaders and investors. These aren’t just big industry names — they’re people I’ve had the privilege of working alongside for years. That trust opened the door for candid, behind-the-scenes conversations you won’t hear anywhere else.
Each guest was interviewed individually, and those full conversations will be released as bonus episodes. But in this three-part mini-series, we’ve woven those insights together — with Spencer and me in the studio reacting to clips — to reveal the patterns, decisions, and principles that define exceptional capital strategy.
In this episode, you’ll hear the full interview with:
Dug Song — co-founder and former CEO of Duo Security (acquired by Cisco for $2.35B), investor, and community builder passionate about cultivating the next generation of founders, operators, and civic leaders.
Subscribe to catch the rest of the series and hear from other iconic leaders. Drop your biggest insight from Dug's story in the comments below.