51. Lawyer, Auditor, Fractional CFO: The Scrappy Path with Rob Bankey

Rob Bankey is the founder of Bankey & Co., a Washington, DC fractional CFO and transaction advisory practice serving growth-stage SaaS, fintech, and AI companies. He led Contactually through its acquisition by Compass and steered Opower through its NYSE IPO before Oracle bought the company, and in 2023 DCA Live named him one of DC's Tech CFO Stars. In this episode, Rob and Jack trace his path from an Arthur Andersen offer that evaporated in the firm's collapse, through Big 4 audit work counting inventory at GM and ConAgra, to law school and a brief stint at the SEC that convinced him he wanted to build things rather than review them after the fact. Rob explains how he ended up running finance at an early-stage startup that eventually IPO'd on the NYSE, why he decided to start his own practice instead of chasing another corporate finance track, and how he thinks about proving ongoing value to clients once the systems are running smoothly ("the trains run on time"). They also get into his golden rule for startup timelines, how he built his ICP through simple word-of-mouth referrals, and a lightning round covering everything from color-coded bookmark folders to how many client inboxes one CFO can realistically manage. Chapters: 0:00 Intro and Scrappy vs Sophisticated 1:43 Growing Up Around the World 7:03 Notre Dame, Japanese, and Landing at Arthur Andersen 10:14 Big 4 Auditing: GM, ConAgra, and the Limits of Audit 13:03 Law School, the SEC, and Finding His Way Back to Finance 17:15 Taking a Startup from First Audit to NYSE IPO 19:45 Starting His Own Fractional CFO Practice 24:59 Proving Value: "The Trains Run on Time" 33:20 Lightning Round: Inside Rob's Office and Inbox 40:55 What's Next and Closing Thoughts Rob Bankey: Website: https://www.bankey.co/ LinkedIn: https://www.linkedin.com/in/rob-bankey-3268561/ Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng