On this episode of Run the Numbers, CJ sits down with Dave McClure and Aman Verjee of Practical VC to talk about the evolution of startup investing — from the PayPal mafia and Founders Fund era to 500 Startups, YC-style scale, and today’s secondary market.
—
SPONSORS:
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer cut their close in half, took audit findings from seven to zero, and cut back-office costs by 70% in six months. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered agents that capture expenses automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000+ companies like OpenAI, Coinbase, Anthropic, and DoorDash already run on Brex. It's time to get Brex AF. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is an automated revenue recognition platform that lets your product team ship new pricing without asking finance for permission, and your sales team close deals without creating downstream chaos. Check out their free tool at calculator.rightrev.com It scores your rev rec process, shows what's exposing you to risk, and tells you exactly where to focus before it bites you in the rear end. Check it out at https://calculator.rightrev.com
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
—
LINKS:
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guests:https://www.linkedin.com/in/davemcclure/https://www.linkedin.com/in/aman-verjee/
Company:https://practicalvc.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
—
TIMESTAMPS:
0:00 Preview and Intro
3:00 Writing as a distribution strategy
5:17 How Dave's blog led to Founders Fund
7:24 Aman: writing at PayPal and law school
9:29 PayPal: the red pen of David Sacks
11:44 Sponsors — Rillet | Maximor | Brex
14:59 500 Startups: the original thesis
16:22 The volume strategy: more shots on goal
18:44 Twilio, Lyft, Sendgrid, Credit Karma
20:15 60x returns: right place, right time
23:07 Sponsors — Anrok | RightRev | Pulley
25:58 Accelerator ecosystem evolution
28:42 500 vs. YC: scale as a weapon
32:52 Globalizing the accelerator model
35:04 Seed to secondaries: how it happened
37:00 Scratching their own itch for liquidity
38:10 The secondary market explained
40:50 Types of secondaries
43:29 Why would a VC sell a winner?
46:07 Managing DPI as a late-stage manager
47:02 The five horse framework
49:15 Skipping the J curve
51:44 Imperfect information as a feature
55:22 Landmines: fraud, mismarked valuations
57:00 VCs lie about valuations three ways
57:58 Forward contracts and counterparty risk
1:00:29 Credits