In this episode of Run the Numbers, CJ sits down with Matt Hedberg, a sell-side equity analyst at RBC who has covered software for more than 20 years. They break down how AI compares to the cloud transition, why traditional software moats are changing, what separates management teams that will actually capitalize on AI, and why cash, customer relationships, data, and technical leadership matter more than ever.

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SPONSORS:

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 posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/

Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. 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 a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj

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

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

EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups

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LINKS:

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

Guest: https://www.linkedin.com/in/matt-hedberg/

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

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

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RBC Capital Markets: This content is based on information available at the time it was recorded, and is for informational purposes only. It is not an offer to buy or sell, or a solicitation, and no recommendations are implied. It is outside the scope of this communication, to consider whether it is suitable for you, and your financial objectives. For Required Conflicts Disclosures, see: https://www.rbccm.com/GLDisclosure/PublicWeb/DisclosureLookup.aspx?entityId=1. For Disclaimer, see: https:/www.rbccm.com/en/policies-disclaimers.page.

What 20 Years of Software Investing Says About AI | Matt Hedberg

Run the Numbers

What 20 Years of Software Investing Says About AI | Matt Hedberg