Planning cadences and the value of planning

In this episode of Run the Numbers, CJ sits down with Jason Lee, CFO of Faire, to unpack the economics of wholesale marketplaces. They break down how Faire connects independent brands with local retailers, the key metrics that matter in marketplace businesses, and ROI as a decision-making framework. Jason also shares lessons from scaling Square through its IPO and how finance leaders navigate valuation resets in private markets.

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SPONSORS:

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Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

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LINKS: 

Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN

Jason: https://www.linkedin.com/in/jason-lee-11787020/

Faire: https://www.faire.com/

CJ: https://www.linkedin.com/in/cj-gustafson-13140948/

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

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TIMESTAMPS:

0:00 Preview and intro

3:01 How Faire serves retailers

5:49 Revenue model and retention metrics

8:21 Recurring vs. reoccurring revenue

11:54 Sponsors — Metronome | RightRev | Rillet

15:17 Input vs. output metrics

17:13 The business equation

19:08 Metric ownership

22:07 Killing metrics: signal to noise

23:21 800 metrics at Faire

24:51 Customer count as a misleading metric

26:04 Sponsors — Tabs | Abacum | Brex

29:25 Planning cadences at Faire

32:41 When to reallocate resources

36:40 ROI as a framework

40:25 Portfolio view of investments

43:53 Discipline is knowing where to say yes

47:11 Faire's valuation reset

50:49 Tender offer mechanics

55:33 Screwing up IR at Square IPO

56:52 Advice to younger self

58:44 AI at Faire

59:32 Claude connected to data warehouse

1:00:16 Tariff analysis with AI

1:02:38 Credits

#RunTheNumbersPodcast #Marketplace #CFO #SaaS #FinanceLeadership