Simplicity vs Black‑Box Models in the Age of AI

In the early days of a startup, forecasting isn’t about nailing the numbers, it’s about setting the course. In this episode, the world’s most interesting CFO describes the art of “Cowboy forecasting” and how this back-of-the-envelope model can be far more valuable than a complex simulation. Kevin Drost started his career as a musician and talent scout for Sony before becoming the chief strategy officer of the music gear marketplace Reverb. Now, as the CFO of New Era ADR, he explains how the company is disrupting the notoriously expensive legal industry by replacing the billable hour with flat fees, and making dispute resolution faster and more predictable for businesses. The conversation also covers why simplicity often beats complexity in financial modeling, how a hands-on understanding of the product and customer builds real financial confidence, and how finance teams can empower every employee to understand and drive the business.

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LINKS:

Kevin Drost on LinkedIn: https://www.linkedin.com/in/kevindrost

New Era ADR:

https://www.neweraadr.com

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

https://www.mostlymetrics.com

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TIMESTAMPS:

(00:00) Preview and Intro

(02:40) Sponsor – Aleph | RightRev | Navan

(07:18) Kevin’s Music Background & A&R at Sony

(12:09) Record Labels Versus Venture Capital

(17:01) Sponsor – Rillet | Pulley | Brex

(20:53) Finding Motivation After Success

(21:34) Building Reverb & the Etsy Acquisition

(25:33) Stacking Skillsets & Interests

(27:11) Cowboy Forecasting at Reverb

(32:01) The Importance of Simplicity in Forecasting in the Early Stages

(35:46) The Art and Science of Making Estimated Guesses

(41:42) Building Firsthand Customer & Product Knowledge

(45:36) Teaching Finance Across the Company

(50:44) New Era ADR & Legal Industry Disruption

(57:35) Legal Strategy Versus Financial Strategy

(1:01:30) How New Era Gets Parties To Use the Platform

(1:05:27) Other White Hot Use Cases for New Era ADR

(1:09:25) The Long Ass Lightning Round: Kevin’s Biggest Mistake

(1:12:41) Advice to a Younger Self

(1:14:01) Finance Software Stack

(1:15:21) Life as an A&R Rep

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SPONSORS:

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RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit

https://www.rightrev.com

and schedule a demo.

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Rillet is the AI-native ERP modern finance teams are switching to because it’s faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.

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#CowboyForecasting #FinanceLeader #StartupFinance #LegalTech #StartupForecasting

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