"Turpentine Finance" with Sasha Orloff | Startup Finance, Leadership, CFO Strategy

In this conversation, Sasha Orloff sits down with Steve McLaughlin, CEO and Managing Partner of FT Partners. Steve provides an insider’s look into the high-stakes world of capital raising and dealmaking for high-growth private companies. From being Goldman Sachs’ Former Head of Fintech to founding FT Partners, a global fintech investment firm, McLaughlin shares his strategies for crafting compelling narratives that unlock massive fundraising rounds - like the $33 billion valuation for Revolut and a $100 million plus raise for Sam Altman’s Worldcoin. They dive deep into storytelling, the importance of product over marketing spend, founder red flags, and much more. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: https://ftpartners.com/ X/SOCIAL: @sashaorloff (Sasha) @FTPartners (Steve) TIMESTAMPS: (00:00:00) The art of storytelling in high-growth company valuations (00:01:31) A capital whisperer's journey (00:02:26) Inside FTPartners: Shaping the fintech universe (00:04:33) The intricacies of capital raising and M&A (00:07:39) Crafting the perfect capital raise story (00:14:13) The complex world of investor networks (00:16:41) Maximizing value beyond valuation (00:19:05) A deep dive into successful storytelling and strategic selling (00:22:57) The philosophy of business growth and valuation (00:23:33) Understanding the founder's journey and ambitions (00:24:32) The role of investment bankers in raising capital (00:25:46) The importance of choosing the right banker (00:28:17) Revolut's success story: A case study (00:36:07) Strategic advice on growth vs. profitability (00:39:01) Reflecting on capital raising experiences and red flags (00:41:06) The evolution of FT Partners (00:46:12) Closing thoughts and acknowledgements

Ever wondered what the financial operations look like when you have billions in AUM at a top-tier VC firm? In this episode, Sasha sits down with Mark Allen, CFO at General Catalyst. Mark discusses the non-obvious complexities of managing billions in assets across hundreds of portfolio companies, from capital reserve strategies, geographical breakdowns, to reporting requirements. He shares candid insights on navigating intense moments like the Silicon Valley Bank collapse, tech innovations being adopted by VC firms, how being a fund’s CFO comprises two roles of being CFO of a fund and a firm, advice for CFOs coming to pitch at General Catalyst, and much more. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: https://www.generalcatalyst.com/team/mark-allen X/SOCIAL: @sashaorloff (Sasha) @generalcatalyst TIMESTAMPS: (00:00) Preview + Intro (02:37) Mark Allen’s Journey to Being CFO of General Catalyst (GC) (06:23) How the VC business model works (08:44) Power law and reserves (08:44) FP&A at a fund and capital reserve strategies (11:20) Investment mix / geographical jurisdictions (14:05) How GC maintains line of sight into their portfolio companies (14:51) Sponsor: Attio (17:04) Tools that Mark uses and revolutions in tools for CFOs (19:12) Using AI for DDQs (21:23) Inflection points in GC’s history (24:19) Transition from hundreds of millions to billions of dollars in AUM (26:01) Critical decision points for GC and Mark (30:14) Sponsor: Turpentine (30:58) Advice for CFOs on building trust with their leadership (33:03) The importance of relationships as a CFO (36:20) How General Catalyst’s work culture has changed after the pandemic (39:18) Biggest misconceptions about being CFO at VC fund (41:26) Advice for CFOs pitching to VCs (42:26) Wrap

Get an inside look at Runway - the visually stunning finance platform that's breaking conventions and captivating users with its approach to making finance fun again. In this interview, founder and CEO Siqi Chen shares the arduous 3-year journey of iterating on the product from its inception during a meeting with the a16z team, working alongside early design partners, and the key inflection points that transformed Runway into what it is today. He emphasizes the importance of storytelling, having the data from different company functions centralized and in communication with each other, and fostering a culture where work, and finance in particular, is genuinely fun. Whether you're in finance or appreciate great product design, this is a must-watch episode. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS MENTIONED: Runway Financial: https://runway.com/ Sandbox VR: https://sandboxvr.com/ X/SOCIAL: @sashaorloff (Sasha) @blader (Siqi) @runwayco (Runway) TIMESTAMPS: (00:00) Introduction to Runway and Siqi Chen (01:30) Background and Inspiration for Runway (08:25) Challenges and Pivot during COVID-19 (12:29) Raising Capital and Product Iteration (14:57) Sponsor: Attio (16:25) Balancing Feature Parity and Novelty (17:30) arly Design Partners and Customers (19:36) Building an Audience and Storytelling (23:01) Mission and Vision of Runway (26:13) Convincing Users to Leave Excel (38:05) Demo of Runway (41:45) Development and Design Process (42:49) Product Features and Future Plans (44:43) Company Culture and Team (46:45) Future of Runway

In this episode, Sasha sits down with Razzak Jallow, CFO at FloQast, to discuss the evolving role of the modern CFO as a strategic partner across the organization. They dive into how he builds trust with the CEO, his approach to fostering product innovation responsibly, and why he turned down a financing round that would have doubled FloQast's valuation. Razzak also offers advice for aspiring CFOs on evaluating their first CFO role, skills like "precision Q&A", and hiring great talent This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- X/Twitter: @sashaorloff (Sasha) @floqast (Floqast) @turpentinemedia TIMESTAMPS: TIMESTAMPS: (00:00) Preview (02:22) How Razzak would describe the role of CFO (02:55) Razzak’s superpowers: hiring and working with different people (04:28) Building trust with different colleagues across different functions and cultures (06:31) How to be the office of “how to” rather than “no” (08:47) Having an effective discussion when there isn’t a right answer (11:47) Changing the culture from being a no shop to a let’s be a partner shop (14:26) Precision Q&A (15:24) Sponsor: Attio (17:22) What is FloQast (19:34) Taking on the first CFO role and evaluating fit (21:45) Deciding not to raise at a higher valuation and why (25:20) Having a cash war chest (27:02) Balancing product innovation and financial discipline as CFO (30:00) The early milestones in a new product that unlock more capital (31:32) Getting alignment on what payback on a new product should be (38:16) Advice to future CFOs and an underrated skill people should work on more (41:39) Building trust with your CEO (45:27) Wrap

Ever wonder what it's like to get a call from Elon Musk, wanting to buy your company? In this episode, Sasha sits down with serial entrepreneur Chris Bakke to find out. Chris is the co-founder behind several successful startups, including Laskie, which was acquired by Elon Musk's X, and Interviewed, acquired by Indeed. Chris shares insights on: building a content-driven growth strategy as a founder that's led to his 200k+ follower base, navigating the M&A process and negotiating a deal directly with Musk, transitioning from founder to his current role in building X's job search platform, and much more. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- X/Twitter: @sashaorloff (Sasha) @chrisjbakke (Chris) @turpentinemedia TIMESTAMPS: (00:00) Chris Bakke Intro (02:49) Laskie and what got Chris excited about it (04:03) Content as a growth strategy (07:29) How Chris found his content voice (12:50) What’s the next thing in content (19:32) Best practices as a founder to set up M&A as a future path (24:36) Getting Indeed as a partner, investor, and acquirer of Interviewed (26:51) Laskie’s M&A Story (29:13) How Chris ended up talking to Elon about Laskie and Twitter recruiting (35:11) What Chris would’ve done differently at Indeed (37:12) Common mistakes and misconceptions during the M&A process (45:00) Chris’ most memorable X post, not of his own (46:22) Wrap

In this episode, Sasha sits down with Sagar Sanghvi, Current Partner at Accel and former CFO at Instacart. They discuss how Sagar drove the change in financial culture at Instacart and adapted rapidly to Whole Food’s acquisition by Amazon, scaling Instacart during the COVID pandemic, the balance between growth at all costs and unit economics, Sagar’s transition from CFO at Instacart to being Partner at the venture firm Accel, and much more. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: https://www.accel.com/people/sagar-sanghvi X/SOCIAL: @sashaorloff (Sasha) @spsanghvi4 (Sagar) @turpentinemedia CONTACT: sps@accel.com TIMESTAMPS: (00:00) Preview and Intro (02:30) Sagar's time at Instacart (04:29) Training from Goldman and KKR (06:58) When to transition to unit economic focus instead of growth at all costs (08:31) The process of changing a financial culture at a company (10:57) Advice for CFOs in driving culture with a founder where financial discipline is not present yet (13:39) Sponsor: Attio (14:55) How do you bring colleagues from other functions into alignment (17:22) Amazon's acquisition of Whole Foods and Instacart's internal dynamics (20:17) Signs that Amazon's acquisition of Whole Foods was a positive infection for Instacart (21:43) Instacart's wartime and tactical parts of Sagar's job during wartimes (24:04) Size of Instacart's finance team (25:10) What Sagar would have done differently in response to the acquisition (27:54) Sagar's VP of Strategy transition to CFO at Instacart (30:13) Balancing growth versus profitability (36:27) Instacart during COVID and lockdown (40:41) Sagar's transition to Accel and VC (44:59) Advice for CFOs positioning themselves to VC (47:34) What gets Sagar excited about a deal? (49:58) Wrap

In the debut episode of Turpentine Finance, host Sasha Orloff sits down with Casey Woo, Founder of Operator's Guild, GP at Fog Ventures, and WeWork's former Global Head of Strategic Finance. They unpack the value of being a business-first CFO, the lessons learned from working in pressure-cooker settings like WeWork, how CEOs can evaluate CFOs (and vice versa), and frameworks for being a career 'specialist generalist'. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: Operator's Guild: https://operators-guild.com/ Fog Ventures: https://www.fog.ventures/ Casey's Linkedin: https://www.linkedin.com/in/caseywoo Casey's contact: hello@operators-guild.com --- X/Twitter @sashaorloff (Sasha) @caseyswoo (Casey) @FogVentures (Fog) @turpentinemedia --- TIMESTAMPS: (00:00) Preview (02:00) Life as a banker (04:06) Story following numbers or numbers following story (04:39)How banking prepared Casey for working in a startup's finance team (07:00) Deciding that working in a startup is a right fit (09:10)Hiring a CFO (11:20) Advice for bankers transitioning to operating roles (12:41) First things to accomplish when stepping into a role (14:05) Sponsor: Attio (14:52) Interview question to see if a founder takes finance seriously (16:16) Advice for CFOs to change the dynamic that finance has in the company (18:08)Casey's time at WeWork as CFO for Western US and Canada (22:00) Casey's experience being Global Head of Strategic Finance at WeWork (29:40 Advice for founders in dealing with different growth or recessive cycles (32:57) Probabilities (34:00) Time spent on fundraising vs supporting the founder as a CFO (35:26) Operator's Guild and Generalists (42:00) How can operators thrive in a transition role (47:28) The number one piece of advice Casey would give to CFOs (49:38) Wrap

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

In this episode, CJ discusses the business of global payments and B2B fintech with Camilla Matias Morais, COO of Brex. Camilla came up in the FP&A world and is a stellar guide to Brex’s strategic bets and moats. Also covered is how she balances the COO role of risk management and company strategy while also being in the weeds with customer feedback. — **PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode 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 ✅ Now through April 15th NetSuite is offering a one-of-a-kind flexible financing program https://netsuite.com/metrics Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN 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: @cjgustafson222 (CJ) @turpentinemedia — TIMESTAMPS: (00:00) Preview (01:06) Intro (02:21) Sponsor: Maxio | NetSuite (05:39) Exploring Fintech Monetization and Business Models (09:36) How the Founder of the Fyre Festival Possibly Started a Credit Card Company (11:11) Making Money Out of Free Fintech Services (14:26) Competitive Moats in Fintech (16:11) Global Expansion: Brex's Strategy for Success (21:01) Sponsor: Attio | Thoropass (23:01) B2C FinTech versus B2B FinTech (29:57) Lifetime Value of a Brex User (32:44) Brex’s Northstar Metric (34:45) Revenue Per Rep: A Deep Dive into Sales Metrics (38:04) Balancing Strategy and Execution: Insights from a COO (39:07) Credit Limit and Managing Risks (44:06) Frameworks for Success: Metrics, Talent, and Internal Mobility (50:24) Avoiding Burnout (54:42) Camila’s Career Screw-Up (58:43) Brex’s Software Stack - Sponsored by Tropic (1:00:10) Wrap

In this episode, CJ talks with the original duo of the HR Heretics podcast, Kelli Dragovich and Nolan Church about tech layoffs in 2024. Kelli and Nolan hold no punches and give straight answers to tough questions on layoffs, the job market, and employment best practices. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a one-of-a-kind flexible financing program until April 15th, 2024. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — RECOMMENDED PODCAST: HR Heretics Join Nolan Church and Kelli Dragovich for unfiltered conversations with people leaders, investors, and CEOS. Dive deep into the kind of leadership-level strategy that often happens behind closed doors. Substack: https://hrheretics.substack.com/ Spotify: https://open.spotify.com/show/1WML9AfadzaH9WCR4HHqbZ — 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 ✅ Now through April 15th NetSuite is offering a one-of-a-kind flexible financing program https://netsuite.com/metrics 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: @cjgustafson222 (CJ) @kellidragovich (Kelli) @NolanChurch (Nolan) @turpentinemedia — TIMESTAMPS: (00:00) Preview (00:25) Round 2 with HR Heretics (01:57) Sponsor: Maxio | NetSuite (04:27) Why Heretics? (05:05) Millennials, Social Media, and Recorded Layoffs (11:26) Navigating Layoffs and Role Eliminations (15:31) Human-Centered is Good Business (17:52) Role Eliminations or Layoff? (19:00) Sponsor: Thoropass | Tropic (21:27) Managing Out Bottom Performers (26:37) Severance Packages: From Crappy to Great (28:11) Supporting Low Performers (31:55) The Illusion of Safety in Big Companies (34:33 ) When Big Company Experience is Sending a Negative Signal (43:20) Working at Smaller Startups (45:31) On Attrition Rates (50:19) Quiet Quitting and Beyond (53:55) Wrap

In this episode CJ is joined by Fred Havemeyer, a leading sell-side equity analyst from Macquarie specializing in AI and software research within the US, delve deep into AI’s impact on the near term role of a CFO. Fred offers an unparalleled analysis of how to quantify productivity gains with AI, the difference between the metrics the sell side uses versus operators and their day to day models. They also cover what company valuations are an art and a science. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode 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 ✅ Now through April 15th NetSuite is offering a one-of-a-kind flexible financing program https://netsuite.com/metrics Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN 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: @cjgustafson222 (CJ) @Montaukmagic (Fred) @turpentinemedia — TIMESTAMPS: (00:00) Preview (01:03) Episode Summary and Intro on Fred (03:10) Sponsor - Maxio | Netsuite (05:46) 2021: High-Profile Breaches (08:19) CFO Metrics and Managing Expectations (11:05) The Beauty Of The Software Space (12:16) Carefully Playing the Game of Metrics (15:40) Does Everything End Up in a DCF Model? (18:06) The AI Revolution: Adoption, Impact, and Future Prospects (22:42) AI's Productivity Paradox: Boosting the Bottom Line (27:10) Sponsor - Attio | Thoropass (29:25) CFOs on AI Pricing Models (32:56) Cost Management and Avoiding Misconfiguration Mistakes (37:39) Margin Profile of Generative AI (42:50) Sponsor - Tropic (44:00) Optimizing Hardware Usage and Mapping the Right Hardware to the Right Problem (46:09) On Snowflake and Optimization, Infrastructure, and Negotiation (50:36) Exploring AI's Capabilities and Limitations on Working with Numbers (58:02) The Future of AI in Business and Risk Management (1:00:09) Wrap

Todd Rakow, CFO of Gladly joins CJ for this deep dive into usage-based revenue models, strategic finance leadership, and the complexities of managing growth and headcount in line with ARR. Todd shares tons of tactical insights, including building out the usage-based model, forecasting customer usage patterns, commissioning sales reps, and teaching your teams to distinguish between reoccurring and recurring revenue. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a one-of-a-kind flexible financing program until April 15th, 2024. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode 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 ✅ Now through April 15th NetSuite is offering a one-of-a-kind flexible financing program https://netsuite.com/metrics 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: @cjgustafson222 (CJ) @turpentinemedia — TIMESTAMPS (00:00) Preview (01:11) Intro (02:31) Sponsor: Maxio | Netsuite (06:09) Usage Based Benchmarks: Here to Stay? (08:01) Understand ARR and its Components (10:30) Recurring or Reoccurring? (12:33) Computing Gladly's ARR (18:13) Seasonality and Alternative Methods to Better Track Revenue (22:25) Sponsor: Thoropass (23:45) Commission Structures And Incentivizing Sales Reps (27:28) Avoiding Foot Faults in Usage-Based Models (28:57) Frameworks Used in Day-to-Day (31:36) Strategic Leadership, Customer Support and Success (32:50) Being a CFO: A Series of Long Uncomfortable Conversations (36:12) Removing the Stigma Around CFOs (37:45) Todd's Insights on the Difference Between a Good and a Great CFO (40:07) Forging a Good Relationship with Your CEO (43:29) Long Ass Lightning Round: What Did Todd Mess Up in His Career? (45:37) What Would Todd Tell His Younger Self? (50:35) Todd’s Software Stack - Sponsored by Tropic (52:41) Craziest Expense Request (53:30) Wrap

Today CJ is joined by Cameron Hyzer, the CFO of ZoomInfo, one of the world's most successful publicly traded data businesses. Cameron discusses the nuances of running a data-driven subscription business, focusing on forecasting, revenue generation through subscriptions and usage-based models, and the importance of customer segmentation. Cameron is a master capital allocator and this conversation touches on why you should focus on quality versus reducing costs as a CFO, share repurchase programs 101, and frameworks for making resource allocation bets. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode 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. Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN 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: @cjgustafson222 (CJ) @turpentinemedia TIMESTAMPS: (00:00) Intro (02:11) Sponsor: Maxio | NetSuite (04:44) ZoomInfo's Secret Sauce (15:13) ZoomInfo's Success (21:50) Translating Macro Trends into Business Strategy (25:14) Strategies for Maintaining Margins and Cash Flow (26:14) Sponsor : Attio | Thoropass (28:27) Managing Customer Relationships and Retention (30:11) Qualities of a Great CFO (33:47) Effective Financial and Operational Data Management (37:26) CFO-CEO Relationship (39:51) Balancing Risk and Opportunity (41:24) CFO as Chief Investment Officer (43:53) Cameron's Tech Stack Brought to You By Tropic (45:52) Wrap

Today CJ welcomes Dave Kline, a leadership coach and owner of the MGMT Accelerator to the pod. The discussion covers tactical advice for managers and leaders to develop high performance cultures among their current teams, including setting clear expectations, running productive 1:1s, and encouraging a compounding ownership mentality from direct reports. They also touch on Dave’s lessons from working at Bridgewater under Ray Dalio, whether a company can have . If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode 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: @DKlineii (Dave) @cjgustafson222 (CJ) @turpentinemedia — LINKS: Dave’s Newsletter: https://mgmt.beehiiv.com/ Dave’s Accelerator Program: https://maven.com/dave-kline/mgmt-accelerator — TIMESTAMPS: (00:00) Intro (02:55) Sponsors: Maxio | NetSuite (05:32) Bridgewater’s Unusual Feedback cycle (08:05) People Capital: the Importance of Understanding Individual Strengths (18:24) Sponsors: Thoropass | Tropic (20:46) Defining Ownership Mentality in Business (26:40) Implementing Ownership Mentality in Teams (28:00) Aligning Incentives for Retention (33:36) The Impact of Job Hopping (35:00) What to Do About Dennis Rodmans (36:28) The Problem with Exceptions (41:27) The Danger of 'That's Okay, I'll Do It' (45:58) Better 1:1 Meetings (49:26) Wrap

Today, the tables are turned as guest Alex Peterson, an expert in Financial Planning & Analysis (FP&A) – and CJ’s first hire – puts CJ in the hot seat. Tune in for two old friends sharing war stories and talking about performance reviews, net dollar retention rates, and Frank Slootman’s retirement. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode 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. Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN 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: @cjgustafson222 (CJ) @turpentinemedia — TIMESTAMPS: (00:00) Preview and Intro (01:57) Sponsor - Maxio |NetSuite (04:47) On Swimming, Endurance and Working in FP&A (07:45) Understanding the Headcount Model (13:12) Reflections on Working Relationships and Working Against the Norm (22:27) Sponsor - Attio | Thoropass (24:42) Alex’s CJisms and Navigating the Job Market Post-COVID (32:14) FP&A Is a Customer Service Role (41:15) Sponsor - Tropic (42:28) A Really Cool Performance Review (44:21) The Legacy of a Leader (47:47) On Frank Slootman’s Retirement (53:28) Understanding the Product You're Selling (56:36) 30-Minute Standing Water Cooler Friday Mornings (59:30) Wrap This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.

In this episode, CJ interviews Adam Swiecicki, CFO at Rippling and former CFO at Brex. They cover valuable insights into Swiecicki's role as well as the strategies that have fueled Rippling's growth in the competitive HR, Finance, and IT space. Adam also shares lessons from being a short seller to a company CFO, the ROI on R&D investment, capital allocation and how to avoid CFO burnout. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — SPONSORS: 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. 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. 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: @cjgustafson222 (CJ) @turpentinemedia — TIMESTAMPS: (00:00) Preview (02:27) Sponsor - NetSuite | Thoropass (05:23) Understanding Rippling's Business Model (09:42) Resource Allocation in a Compound Startup (15:54) Sponsor - Maxio (17:02) Competitive Moats in the SaaS Industry (23:01) Launching Rippling’s Finance Cloud (26:43) Understanding Customer Lifetime Value at Rippling (28:36) The Signal of a Strong PMF (30:34) Rippling's Northstars (32:45) The Concept of Revenue Growth Endurance (33:40) The Role of a CFO (36:12) Balancing Strategy and Execution (40:25) Adam’s Frameworks, Methods, or Processes for Prioritizing Work (44:10) From Short Selling to Running a Company (48:10) Avoiding CFO Burnout: Enjoying the Journey (51:23) Adam’s Craziest Work Experience and Expense (53:27) Rep Yo Stack Sponsored by Tropic: Adam’s Finance Software Stack (57:57) Wrap This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.

In this episode, CJ interviews Jack Greco, the co-founder of ACV Auctions, a publicly traded B2B marketplace for automobiles. Now Greco is a VC and Angel investor. In this conversation they cover the human element necessary in any marketplace business, setting up makep-good budget for mistakes, business seasonality, and how the auction model affect supply and demand liquidity. This is truly a masterclass in all things marketplaces and valuable for anyone who is interested in businesses which depend on a high degree of trust. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — SPONSORS: 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. Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join OpenAI, Replicate, ElevenLabs and more at https://bit.ly/AttioRTN 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. 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: @cjgustafson222 (CJ) @turpentinemedia — TIMESTAMPS: (00:00) Preview (02:20) Sponsors: NetSuite | Attio (05:12) Understanding the Human Aspect of Business (09:07) Using a 'Make Good Budget' in Business (13:18) Marketplace is the Cart, Not the Horse (Understanding the Nature of Marketplaces) (14:59) Sponsor: Maxio | Thoropass (17:27) Creating Liquidity From Marketplaces (22:55) Auction in Marketplaces: Where Kinetic Energy Dances On (26:12) Seasonality in Business (30:45) The Role of Timing in Business Success (32:25) How ACV Evolved and Developed its Competitive Edge (35:52) Human Interaction - A Necessary Spice (39:04) Sponsor: Tropic (39:48) The Single Decision that Unlocked the Most Value (42:49) Jack's General Philosophy Around Setting a Take Rate (47:11) Payment Responsibility and Demand Generation (48:18) The Colorful People in the Used Car Business (and other wacky operational things) (50:44) The Importance and Frequency of Investor Updates (52:51) Wrap This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.

In this episode, CJ is joined by Matt Gallatin, CFO of Stack Overflow, the largest online community for developers and one of the most popular websites in the world. They cover the impact of doing SaaS 101 learning sessions with departments across the org, how CFOs can get involved in the customer lifecycle reviews, CFO career stories demonstrating high stress decision-making in action, and more. If you’re looking for an ERP platform, check out our sponsor, NetSuite: https://netsuite.com/metrics — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — SPONSORS: 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. 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. 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: @cjgustafson222 (CJ) @turpentinemedia — TIMESTAMPS: (00:00) Preview (02:25) Sponsors: NetSuite by Oracle | Thoropass (05:05) Tying Together the SaaS Model for the Whole Company (06:54) SaaS 101 Sessions (09:36) Understanding SaaS Metrics (13:51) Customer Life Cycle Review (17:16) Sponsor: Maxio (18:29) Matt’s Bold Decision at Drawbridge (25:57)The Aftermath and Lessons Learned from that Decision (27:33) Not All Revenue is Created Equal (28:14) Understanding Business Growth and Trajectory (29:55) Using Public Companies As Aspirational Benchmarks (37:59) Digging Into S1s (40:30) Matt’s Favorite Benchmark Reports (43:50) CFOs are like NFL Coaching Trees (48:20) Matt’s Finance Software Stack Brought to you by Tropic (50:51) Wrap This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.

Today CJ welcomes back Jim Cook, a renowned coach to chief financial officers throughout Silicon Valley through his company BenchBoard Advisory -- and a co-founder of Netflix. Jim takes us through a number of frameworks for decision making and communication, including the three eras of CFO requirements, the concept of disagreeing, but still committing as a management team, challenging the problem, not the person, how the most valuable skill CFOs can learn is communication, the leadership SECS talk, and much more. If you’re looking for an ERP platform, check out our sponsor, NetSuite: https://netsuite.com/metrics — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — SPONSORS: 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. 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. 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: @cjgustafson222 (CJ) @cookflix (Jim) @turpentinemedia — TIMESTAMPS: (00:00) Introduction: The Power of Data-Driven Decisions (02:32) Sponsor - Netsuite | Attio (04:46) The Return of Jim Cook: A Masterclass in CFO Communication (07:06) The Four C's of Teams: A Framework for Decision Making (16:40) Sponsor - Maxio | Thoropass (23:29) The Three Eras of a CFO: From Ownership to Leadership (26:10) The Five Steps to Ownership (31:20) Sponsor - Tropic (32:33) Communication: Who is in the room? (37:16) SECS Talk (40:10) Being Comfortable in Silence (40:40) 3 Things Humans Remember (48:00) Captain of Three Ships: Relationships, Partnerships, and Leadership (49:06) Wrap This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.

On today’s episode, CJ welcomes Chad Gold, the CFO of G2 and the former CFO of Salesloft. Gold shares valuable insights on the role of finance in startups and the qualities that set you on the path for a successful CFO career in venture-backed ecosystems. If you’re looking for an ERP platform, check out our sponsor, NetSuite: https://netsuite.com/metrics — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — SPONSORS: 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. 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. 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: @cjgustafson222 (CJ) @chadjgold (Chad) @turpentinemedia — TIMESTAMPS: (00:00) Intro (02:32) Sponsors: NetSuite | Thoropass (05:04) Building Relationships with Investors (11:28) Understanding Majority Recapitalization (18:16) Sponsor: Maxio (22:07) Building Great Finance Teams (25:06) Ownership Mentality (25:42) How Finance Teams Can Empower Their Company (29:39) Making The News and proactivity (33:15) Feedback Cycle (37:20) The Importance of Relationships (40:16) The Role of Finance in Business Operations (42:03) Chad’s Past Mistakes (45:55) Chad’s software stack brought to you by Tropic This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.