Communication, Tax, and Cashless Exercises

Secondaries aren’t a niche anymore — they’re the main event. In 2025, the secondary market hit $233B, outpacing IPOs 5:1. This episode breaks down how we got here, why companies stay private longer, and how employees, investors, and CFOs actually navigate liquidity. From Facebook’s wild west to structured tenders and continuation vehicles — this is the new playbook.

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SPONSORS:

Aleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run

RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ

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

EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com

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

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

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

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

Slacker Stuff: https://www.slackerstuff.com/

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Finance vs. Marketing: Who’s Really Right About ROI? | Brandon Sullivan

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Do the things spreadsheets can’t do | SeatGeek’s Teddy Collins

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TIMESTAMPS:

0:00 The $233B market replacing IPOs

2:57 What is a secondary?

4:24 The dot-com hangover

5:48 The wild west era

8:58 Sponsors — Aleph | RightRev | Rillet

12:21 Why companies stay private longer

13:56 The three stakeholders

18:57 When is it too early?

20:42 How to run one of these things

23:57 Sponsors — EY | SpendHound | Brex

27:04 Not all shares are created equal

31:08 The good, the bad, and the ugly

34:23 GP-led continuation vehicles

36:19 The whole game changed

37:34 Credits

#RunTheNumbersPodcast #PrivateMarkets #SecondaryMarkets #VentureCapital #CFO