How to Sell Your Company: A Multi-Time CFO's Full Playbook | Rick Smith

CJ sits down with multi-time CFO Rick Smith, founder of Bonfire Advisory and author of Six Months to the Sale, to break down what actually happens when you sell a company. They cover why buyers value some businesses on ARR and others on EBITDA (and why being slightly profitable can hurt you), how to negotiate banker fees, what buyers find when they dig into your balance sheet, and why every cap table Rick inherits is wrong.—SPONSORS: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 It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down.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/cjRillet 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/cjMaximor 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/metricsAnrok 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/rtnEY 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/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: linkedin.com/in/rick-smith-906939Company: https://www.linkedin.com/company/bonfire-advisoryCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:1:21 Meet Rick Smith and "Six Months to the Sale"2:44 Why Teach M&A Through Fiction4:26 CEO/CFO Tension7:08 Botching the Announcement8:15 How Staff Really React9:18 When Personal Life Collides With a Deal13:50 ARR vs. EBITDA17:58 What to Optimize Before a Sale18:50 Churn and Contract Renewal20:43 Strategics vs. PE27:46 Investment Banker Fee Structures29:09 What's Negotiable29:56 The Realtor Problem34:53 Big 4 vs. Regional Firms for Audit and QoE35:47 Negotiating Accounting Fees37:47 Deferred Revenue41:23 Warrants, Options, and Carta Cleanup44:02 QSBS: What CFOs Need to Know45:28 Quality of Earnings: Who Pays and Why47:44 What a QoE Actually Digs Into51:22 Why Deal Momentum Is So Hard to Stop53:47 The Waterfall58:19 Who Keeps Their Job61:31 Why Selling CFOs Feel Intimidated62:56 Prospect Theory65:28 Where to Find the Book#RunTheNumbersPodcast #MandA #CFOLife #SellingACompany #QualityOfEarnings