E52: A CFO & CEO Walk Into a Bar | CJ Gustafson & Sasha Orloff

Today is a special episode where CJ Gustafson and Sasha Orloff (3x founder and current CEO of Puzzle) go deep on the CFO-CEO mindsets…and talk podcasting. They cover: highlights and memorable advice from CJ’s 50+ interviews on this feed, how to have impact as a CFO & CEO, the challenges of building finance software, each host’s biggest mistakes, and how to make a successful podcast. Turpentine Finance hosted by Sasha Orloff will debut later this week and this season will feature firsthand stories from guests about the greatest inflection moments in the history of Mercury, OpenAI, Andressen Horowitz, Netflix, Runway, and more. 📅 Turpentine Finance hosted by Sasha Orloff debuts on 4/4/24. CJ's Run The Numbers continues with great new content over on: Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — SPONSORS: Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year. NetSuite provides financial software for all your business needs. More than 37,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒 Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how. — FOLLOW US ON X: @sashaorloff (Sasha) @cjgustafson222 (CJ) @turpentinemedia — TIMESTAMPS (00:00) A Hilarious Start (00:33) Starting a Podcast (02:25) Exploring the CEO-CFO Relationship (04:09) Two Superpowers of CFOs (07:52) From Content Creation to Building Run the Numbers (11:11) Sponsor: Maxio | NetSuite (13:41) Lessons CJ Learned from Episode 1 Onwards (17:37) Creating Content and Finding the Right Audience (22:28) Sports, Seasonality and Unique Business Models (28:44) Challenges of Building Puzzle.io (31:46) AI Revolution in Finance (35:29) Sponsor: Thoropass | Tropic (38:00) Building the Turpentine Finance Podcast (40:23) Sasha's Career Mess-Up (46:50) Building Something Bigger (and Still Have a Bit of Hair) (53:40) Sasha's Frameworks for Managing Time and Impact (57:39) Spinning Your Own Thing and Betting on Yourself (1:02:04): Wrap