AI Agents and Proactive Matchmaking

In this episode of Run the Numbers, CJ Gustafson sits down with Colin Gardiner, General Partner at Yonder VC and former Chief Revenue and Product Officer at Outdoorsy, to unpack what really drives successful marketplace businesses. Colin shares lessons from scaling a peer-to-peer RV platform, where the biggest unlock came not from casual users but from power hosts optimizing utilization and yield through the SaaS tools they built. He introduces his “Marketplace Plus” investing framework—showing how layering SaaS and professional tools can transform a platform into an operating system—and where founders risk overreaching by taking on inventory or managing supply too tightly. The conversation dives deep into monetization, pricing psychology, take rates, and the fine balance between product-market fit and margin obsession, before zooming out to explore how AI and the decline of SEO are reshaping marketplace discovery.

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LINKS:

Colin on LinkedIn: https://www.linkedin.com/in/colingardiner/

Company: https://www.yonder.vc/

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

Mostly metrics: https://www.mostlymetrics.com

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RELATED EPISODES:

996 Culture, Exploding AI Bills & SaaS Chaoshttps://youtu.be/qhrxDL0gsRo

“Keep the Take Rate Low” - Turo’s Chuck Fisher on Scaling a Successful Peer-to-peer

https://youtu.be/LKH8o1MjnZo

The Art of Stacking S-Curves: Olo’s Winning Vertical SaaS Strategy with CFO Peter Benevides

https://youtu.be/1X2VoYogj44

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TIMESTAMPS:

00:00:00 Intro and Guest Overview

00:02:57 Sponsors – RightRev, Tipalti, and Aleph

00:07:13 Outdoorsy and the RV Market

00:10:33 Balancing Supply and Demand

00:13:05 Marketplace Plus Model

00:16:59 Sponsors – Fidelity Private Shares, Metronome, and Mercury

00:21:45 Professionalizing Marketplaces

00:24:10 Building Software, Insurance, and Financing Layers

00:28:07 Avoiding Fully Managed Models

00:32:34 Take Rates and Pricing Strategy

00:35:00 Monetizing Both Sides

00:37:06 Advertising and Marketplace Scale

00:39:48 Marketplaces Meet Social Platforms

00:42:36 AI and Marketplace Distribution

00:45:54 AI Agents and Matchmaking

00:47:03 When AI Becomes the Supply

00:49:09 Negative Gross Margins and Scale

00:53:04 Picking a Side – Supply or Demand

00:54:35 Branding, Utilization, and Growth

00:55:42 Closing and Credits

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SPONSORS:

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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Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run

Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com

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#RunTheNumbersPodcast #MarketplaceStrategy #AIPoweredBusiness #SaaSModel #StartupFinance

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