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Raising capital isn’t the summit, it’s the start of the climb.
The moment you take the money, expectations change. Trust is tested. Discipline is exposed. And what looked like momentum can quickly turn into a mess.
In this For You Leaders mini-series, Kirk Dando and Spencer Traver bring together five iconic founders and investors who’ve raised, deployed, and returned billions — and learned what it really takes to scale with integrity and discipline.
You’ll hear from:
- Brett Hurt — Serial entrepreneur (Bazaarvoice, data.world) on raising when you don’t need the money and why ego is a founder’s silent killer.
- Dug Song — Co-founder of Duo Security on capital discipline, his unique “12-month post-money rule,” and how to grow without losing control.
- Julie Maples — Co-founder of FYRFLY Ventures on downrounds, trust, and what healthy investor relationships actually look like.
- Mitchell Green — Founder of Lead Edge Capital on clean deals, messy cap tables, and why simplicity beats complexity every time.
- Gregg Kaplan — Founder of Redbox on treating cash as a precious commodity and staying honest when markets change overnight.
Together, they’ve built and backed companies worth billions. But their shared insights go beyond capital... they reveal the patterns of leadership, trust, and discipline that separate those who scale wisely from those who burn out fast.
In this episode, you’ll learn how to:
- Avoid the “valuation trap” that quietly destroys alignment.
- Raise capital without compromising control or clarity.
- Recognize when to slow down before speeding up.
- Build the trust and awareness that sustain long-term growth.
This is a candid look at the truth behind raising and deploying capital, and why the climb after the check clears is where real leadership begins.
Episode Breakdown:
00:00 – Intro: Capital and the Climb
03:02 – Setting the Stage: Why Raising Capital Isn’t the Summit
11:03 – Defining the Valuation Trap
38:18 – How to Exercise 'Capital Discipline'
1:10:39 – The Value of a Self-Aware Founder
1:21:55 – Closing Thoughts: Trust, Discipline, & The Climb Ahead
