How a Former Pro Musician Became the CFO of a $1B Marketplace, with Kevin Drost

How does someone go from jazz musician to CFO of a $1B marketplace?

In this episode of The Growth-Minded CFO, Alex Louisy and Lauren Pearl speak with Kevin Drost, former CFO of Reverb — the musical instrument marketplace acquired by Etsy — about his unconventional path into finance and what it taught him about the role.

Kevin didn’t start in finance. He started by running a business. From founding a record label to navigating cash flow, trade-offs, and uncertainty in real time, he learned finance by doing — not by following a traditional path.

In this conversation, he shares how that operator mindset shaped his approach as a CFO, why finance leaders need to stay close to customers, and how the role has evolved from reporting performance to helping drive growth.

Chapters:

02:38 From Jazz to Record Labels

05:18 Learning Business on the Fly

06:51 MBA While Operating

10:40 MBA Value Framework

14:13 Faking It and Risk

20:19 Why Choose CFO

23:57 Leaving Consulting for Reverb

25:28 Building the Music Marketplace

26:32 Choosing Growth Priorities

27:25 From Strategy to CFO

29:21 Learning by Doing

35:05 Public Company Rigor at Etsy

37:27 Marketplace Metrics and ROI

40:42 New Era ADR Mission

44:57 Advice for Finance LeadersIn this episode, Kevin covers:

• Why learning finance inside the business builds better judgment
• The limits of traditional career paths (and when an MBA actually helps)
• How marketplace businesses create complex trade-offs
• Why CFOs need to take calculated risks to drive growth
• The importance of staying close to customers and product
• How to scale a business without losing control
• Why putting yourself in uncomfortable roles accelerates learning

As Kevin puts it: “Getting yourself out and speaking to customers is probably the most valuable thing you can do as a finance leader.”This is a practical look at how finance leaders can move beyond reporting and play a more active role in shaping the business.Watch this episode on YouTube: https://youtu.be/W30D0JNJnLg?si=53lBTp2oyBHyTXBVIf you’re a CFO, finance leader, or operator, this episode will give you a clearer view of how the role is evolving — and what it takes to stay effective as the business grows.Subscribe for more conversations with growth-minded finance leaders shaping the future of the CFO role.The Growth-Minded CFO podcast challenges the status quo and explores how the best CFOs approach their work and lives. Hosts Lauren Pearl (Fractional CFO, 3-time Founder, and Startup Finance Instructor at NYU) and Alex Louisy (FinTech CEO and Y Combinator graduate) speak with inspiring finance and business leaders about what it takes to support high-performing organizations.This podcast is powered by Upflow — a Financial Relationship Management platform enabling faster payments, stronger customer relationships, and efficient growth for your business.Join thousands of next-level finance leaders and go from chasing invoices to engaging customers. Find out more at upflow.io.Want to get in touch? Reach out to our producer at joseph.sweeney@upflow.ioWant to recommend a guest? Apply via our form: https://insights.upflow.io/apply-to-be-a-guest-on-the-growth-minded-cfo-podcast