How a Former Musician Became the CFO of a $1B Marketplace, with Kevin Drost
Can an unconventional path actually make you a better CFO? For Kevin Drost, the road to finance leadership didn’t start in accounting or banking, but with running a business and figuring things out as he went.
Before becoming CFO of Reverb, the musical instrument marketplace later acquired by Etsy, Kevin was a jazz musician, a talent scout at Sony, and the founder of his own record label. Finance wasn’t something he set out to do. It became necessary because the business needed it.
“I found that I actually really loved running a business. I loved the kind of mechanics and operations of how a business operates. I loved the financial elements of it. They were all things I didn’t totally know until I was actually in the seat making decisions.”
That experience shaped how he thinks about finance. When you’re responsible for making something work, the numbers stop being theoretical. They’re tied directly to outcomes.
Learning Finance By Doing (and Studying Alongside)
Kevin didn’t learn finance in a classroom first. He learned it through running a business, where every decision had consequences. Managing a record label meant dealing with cash flow, trade-offs, and uncertainty every day, often without perfect information. There was no separation between strategy and execution, so he had to understand how decisions played out in reality.
Later on, he did choose to pursue an MBA, but he did it part-time while continuing to work. It wasn’t about stepping away from the business to learn theory. It was about adding structure to what he was already experiencing.
When asked about the value of an MBA, his view is balanced:
“There’s certainly value in what you’re going to learn from there… but if you’re in a startup business, an MBA is not going to guarantee you a promotion, it’s not going to guarantee you any kind of salary.”
For Kevin, the real learning still came from being in the business. Seeing how decisions unfold, where things break, and how value is actually created is what builds judgment over time.
From Operator to Marketplace CFO
By the time Kevin became CFO at Reverb, he was bringing an operator’s mindset into the role. He understood how businesses run, not just how they’re reported on.
That becomes especially important in a marketplace business. These businesses are interconnected systems. Pricing changes behaviour, supply affects demand and pushing too hard in one area can create problems somewhere else. What looks like progress in a dashboard doesn’t always reflect what’s happening in the product or customer experience.
In that environment, finance needs to stay close to the business. It has to be part of the decision-making, not just tracking what happens after the fact.
Risk, Growth, and the Role of Finance
Once finance is embedded in the business, the conversation shifts. It’s less about explaining what happened and more about deciding where to go next.
That’s where Kevin sees the role of the CFO evolving. Finance isn’t just there to manage downside, but plays a role in enabling growth:
“You are gonna have a hard time sort of being innovative, driving real growth, really differentiating both yourself and your business if you’re not able to make calculated risks…”
Growth always involves risk, and the challenge is knowing which risks are worth taking and how far to push. That’s where judgment comes in, and that judgment depends on how well you understand the business.
Staying Close to the Customer
A big part of that understanding comes from getting out of the finance function and closer to customers:
“I think, quite honestly, getting yourself out and speaking to customers is probably the most valuable thing you can do as a finance leader.”
It’s easy to rely on dashboards and reports, but they only tell part of the story. Without context, numbers can be misleading. Talking to customers gives you a better sense of what’s actually driving the numbers. It helps connect the data to real behaviour, which leads to better decisions.
Staying Uncomfortable
A consistent theme in Kevin’s career is a willingness to step into unfamiliar territory. After Reverb, he moved into a very different space with New Era ADR, a company focused on legal dispute resolution.
“I’ve always tried to put myself in positions where I’m a little bit uncomfortable… because that’s where you actually learn the most.”
At a senior level, it’s easy to stick to what you know. But Kevin has deliberately taken the opposite approach. Each move has forced him to learn something new and adapt how he thinks about the role. That mindset is becoming more important as the CFO role continues to evolve.
A Different Kind of CFO
Kevin’s journey shows how much the CFO role has changed. It’s broader now. It requires judgment, context, and a clear understanding of how the business operates day to day.
There isn’t a single path into the role anymore. What matters is whether you can connect the numbers to what’s actually happening and make decisions in situations that aren’t always clear.
Full Episode
If you’re a CFO or finance leader trying to move from reporting the numbers to shaping the business, this episode is worth your time.
Kevin’s story is a reminder that strong finance leaders stay close to how the business really works — not just how it looks on paper.
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