How Great Deals Are Found, Evaluated, and Won | PSG’s Chris Nesbitt

In this episode of Run the Numbers, CJ sits down with PSG Managing Director Chris Nesbitt to unpack how great deals are actually found, how investment decisions are really made, and why narrative often matters more than most investors admit. They also dig into forecasting, boardroom authenticity, simple vs. complex models, and the roles of market, product, and leadership in driving outcomes.—SPONSORS: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/metricsAleph 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/runRightRev 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/CJRillet 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/cjEY 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/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/christophersnesbitt/Company: https://psgequity.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro2:44 PSG origin story4:01 Growth to 30B AUM5:07 Strategy: small software at scale5:50 Vertical SaaS treasure hunting8:10 Ministry Brands: software meets payments9:28 Sponsors — Brex | Aleph | RightRev12:46 Early M&A work and rollup strategy15:52 Sourcing is more competitive now18:28 Smoke signals and relationship sourcing21:22 Does brand get you in the room?22:15 Authenticity as a sourcing edge22:52 Sponsors — Rillet | EY | SpendHound26:09 Brand name of investor or deal partner?27:44 Investors are narrative driven animals29:18 Market, product, then execution31:26 Danger of falling in love with the narrative33:40 Operator AI pivot story: GRC company34:51 Keep it simple: one tab, five key inputs39:21 Forecasting confidence beyond 12-18 months41:51 What makes a useful board meeting45:01 Build vs. buy: the payments decision47:45 ARR vs. EBITDA multiples50:30 Lightning round50:34 Board materials: send 3 days in advance51:03 LTV to CAC and cap software debates51:32 First deal at PSG52:35 What young investors get wrong54:04 Credits