"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech

OpenAI Controller Sowmya Ranganathan sits with Sasha Orloff to share accounting insights from her experience at Square, Rippling, and OpenAI. She discusses automation and using AI in accounting, how difficult software motivated her to make the move to Controller at Rippling, and how she’s streamlining the accounting workflow at OpenAI, where she is currently Controller. Sowmya also explains how AI is making accounting easier and why future accounting teams may be small and broadly skilled. 🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj RECOMMENDED PODCAST: Patrick McKenzie (@patio11) talks to experts who understand the complicated but not unknowable systems we rely on. You might be surprised at how quickly Patrick and his guests can put you in the top 1% of understanding for stock trading, tech hiring, and more. Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812 📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week. Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812 --- This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co --- SPONSORS: ATTIO 📊 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 NETSUITE 📈 NetSuite has 25 years of providing financial software for all your business needs. More than 36,000 businesses have already upgraded to NetSuite by Oracle, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you’re looking for an ERP platform head to NetSuite: http://netsuite.com/zen - NetSuite has extended a one-of-a-kind flexible financing program for a few more weeks. BEEHIIV 🐝 Head to Beehiiv, the newsletter platform built for growth, to power your own. Connect with premium brands, scale your audience, and deliver a beautiful UX that stands out in an inbox. Go to https://beehiiv.com and use code “MOZ” for 20% off your first three months BRAVE 🎯Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. --- 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/SOCIAL: https://twitter.com/sashaorloff (Sasha) https://twitter.com/heysowmya (Sowmya) --- TIMESTAMPS: (00:00) Preview and Intro (02:51) Soumya's Journey: From Square to Rippling (03:14) Challenges and Learnings in Public Accounting (07:30) Automation in Accounting: A Necessity (10:02) Joining Rippling: Building from the Ground Up (11:47) Balancing Controls and Growth in Startups (14:52) Sponsor: NetSuite | Attio (16:52) Putting On the Auditor's Hat (18:24) What If There's No Buy-in from Management? (21:02) Stepping into OpenAI and Embracing AI in Accounting (24:12) Transforming Accounting with ChatGPT (25:35) Real-World Applications and Success Stories (26:29) Future of AI in Accounting (29:44) OpenAI's Accounting Team and Processes (30:02) Sponsor: Beehiiv | Brave (33:12) Innovative Tools and Systems (37:36) Advice for Future Accountants (45:30) Addressing Fear of AI in Accounting (47:41) Wrap

In this episode, Sasha Orloff is joined by Andrew Gazdecki, founder of Acquire.com, who shares his expertise on successfully selling companies, maximizing exit value, and key lessons from his own acquisition experiences, with over $500 million in closed deals. — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — Highlights from the Episode: Creating a competitive process with multiple potential buyers is crucial for maximizing exit value - "if you have one buyer, you have no buyer" Proper preparation and documentation (clean financials, confidential information memorandum) significantly speeds up the acquisition process and builds buyer confidence Being transparent about business challenges upfront ("bruises and all") builds trust and allows you to control the narrative around potential objections -- RECOMMENDED PODCAST: Check out Modern Relationships, where Erik Torenberg interviews tech power couples and leading thinkers to explore how ambitious people actually make partnerships work. Founders Fund's Delian Asparouhov and researcher Nadia Asparouhova kick off the series with an unfiltered conversation about their relationship evolution. Apple: https://podcasts.apple.com/us/podcast/id1786227593 Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg YouTube: https://www.youtube.com/@ModernRelationshipsPod — SPONSOR: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod — LINKS: Acquire: https://acquire.com/ https://www.linkedin.com/in/agazdecki/ — X/SOCIAL: @acquiredotcom (Acquire) @agazdecki (Andrew) @sashaorloff (Sasha) — TIMESTAMPS: (00:00) Intro (02:10) Personal lessons from selling Business Apps (03:50) Building Acquire.com from personal experience (06:49) First acquisition story with ESW Capital (09:28) Negotiating terms and tax considerations (12:20) Story of Altcoin acquisition (13:53) Sponsor: Notion (15:15) Experience at Spiff and path to Acquire.com (18:35) Maximizing exit value strategies (25:47) Process of listing on Acquire.com (27:36) Types of buyers and deal sizes (29:34) Success stories and notable deals (32:57) Future plans for Acquire.com (34:04) Wrap

In this episode, Rishi Garg, former Head of Corporate Development at Twitter and Square, shares insider knowledge on tech acquisitions. He explains when companies should start considering M&A and the three key approaches: tops down, bottoms up, and strategy influence. Rishi reveals how he managed up to 15 deals in 12 months and why integration is crucial for M&A success. He debunks common M&A misconceptions and discusses the "sins of omission" - deals he regrets not making. The conversation shifts to his current role as a VC at Mayfield Fund, offering a unique perspective on both sides of acquisitions. LINKS: https://www.twitter.com/rishigarg https://www.mayfield.com/ RECOMMENDED PODCAST: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz YouTube: https://www.youtube.com/@ThisWontLastpodcast SPONSORS: More than 37,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud financial system bringing accounting, financial management, inventory, HR, into ONE proven platform. If you're looking for an ERP platform, get a one-of-a-kind flexible financing program on NetSuite: https://netsuite.com/102 Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics The Brave search API can be used to assemble a data set to train your AI models and help with retrieval augmentation at the time of inference. All while remaining affordable with developer first pricing, integrating the Brave search API into your workflow translates to more ethical data sourcing and more human representative data sets. Try the Brave search API for free for up to 2000 queries per month at https://brave.com/api Omneky: Omneky is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/ X/SOCIAL: @sashaorloff @rishigarg (Rishi) TIMESTAMPS: (00:00:00) Introduction (00:02:53) How companies should think about M&A and corp dev (00:06:58) Signs that a company is ready to consider M&A (00:11:37) Different approaches to M&A: tops down, bottoms up, and strategy influencing (00:16:52) How to start building an M&A team (00:18:16) Sponsors: Netsuite | Metaview (00:22:15) Misconceptions about M&A in Silicon Valley (00:26:53) Valuation considerations in M&A deals (00:34:31) Current state of M&A market and opportunities (00:38:24) Sponsors: Omneky | Brave (00:39:47) How M&A deals happen and relationship building (00:45:55) Reasons why M&A deals don't work out (00:51:50) Transition to Rishi's experience as a venture capitalist (00:57:50) Advice for founders considering M&A (01:02:09) Rishi's current interests in investing, particularly in AI and new platforms

In this episode of Turpentine Finance, Sasha sits down with Eric Ries, author of "The Lean Startup" and founder of the Long-Term Stock Exchange (LTSE). Ries shares the challenging journey of creating a new national securities exchange designed to promote long-term thinking in public companies. He discusses the obstacles faced in gaining SEC approval, the misconceptions about corporate governance, and why many companies struggle with balancing short-term pressures and long-term vision. Ries offers valuable insights for CEOs and CFOs considering going public or dual-listing, emphasizing the importance of aligning investors with a company's long-term mission. This conversation explores how rethinking capital allocation and corporate structure can lead to more sustainable, successful businesses. LINKS: The LTSE: https://ltse.com/ The Lean Startup: https://theleanstartup.com/ Listen here at: https://www.ericriesshow.com/ RECOMMENDED PODCAST 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz YouTube: https://www.youtube.com/@ThisWontLastpodcast SPONSORS: RIPPLING SPEND: Imagine total control over your company's spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit rippling.com/spend for a free demo and one month free trial. NETSUITE More than 37,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud financial system bringing accounting, financial management, inventory, HR, into ONE proven platform. If you're looking for an ERP platform, get a one-of-a-kind flexible financing program on NetSuite: https://netsuite.com/102 BRAVE: The Brave search API can be used to assemble a data set to train your AI models and help with retrieval augmentation at the time of inference. All while remaining affordable with developer first pricing, integrating the Brave search API into your workflow translates to more ethical data sourcing and more human representative data sets. Try the Brave search API for free for up to 2000 queries per month at https://brave.com/api X/SOCIAL: @sashaorloff @ericries (Eric) TIMESTAMPS: (00:00:00) - Introduction and opening quote from Eric Ries (00:02:18) - Explanation of what the Long-Term Stock Exchange (LTSE) is (00:07:11) - Eric's background and journey to founding LTSE (00:14:29) - The challenge of convincing investors to fund LTSE (00:16:03) - Sponsors: Netsuite | Rippling Spend (00:21:47) - Eric's experience navigating the SEC approval process (00:29:38) - Sponsor: Omneky (00:31:30) - Discussion on how companies are notified of SEC approval (00:42:36) - Challenges and questions companies ask behind the scenes (00:50:36) - Brief mention of companies listed on LTSE (00:58:36) - The importance of allocating shares to long-term investors (01:01:21) - What's next for LTSE and Eric Ries (01:02:49) - Closing remarks and outro

In this episode, Sasha sits down with Jody Padar, the Radical CPA, 3x author, to discuss the incentive misalignment in accounting firms, and how radical pricing can solve it. Jody shares her insights on the evolving landscape of accounting, discussing the need for firms to adapt to new technologies, embrace value-based pricing, and shift from traditional hourly billing models. She emphasizes the importance of redefining the accountant-client relationship in the digital age, advocating for a more advisory-focused approach. Jody also addresses the challenges facing the accounting profession, including talent shortages and the impact of automation, while offering her vision for the future of accounting firms. -- 🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode RECOMMENDED PODCASTS: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz YouTube: https://www.youtube.com/@ThisWontLastpodcast -- LINKS: Radical Pricing by Jody Padar: https://cpatrendlines.com/shop/jp24pri-jody-padar-radical-pricing-how-to-optimize-profits-delight-clients-and-build-a-top-value-firm-jp24pri/ Connect with Jody on Linkedin: https://www.linkedin.com/in/jody-padar-18a9711 -- SPONSORS: 📈 NetSuite has 25 years of providing financial software for all your business needs. More than 36,000 businesses have already upgraded to NetSuite by Oracle, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you’re looking for an ERP platform head to NetSuite: http://netsuite.com/zen - NetSuite has extended a one-of-a-kind flexible financing program for a few more weeks. 🦾 Level up your ineffective website chatbot with CommandBar. CommandBar builds a new type of web assistant which delivers highly personalized responses, real time co-browsing, and can perform actions on behalf of the users. Learn how Hashicorp, Gusto, Freshworks and more use CommandBar at https://commandbar.com/moz 🌐 Ready to achieve your 2024 goals? Start learning a new language with Babbel in just three weeks. Enjoy app lessons, live classes, and podcasts designed for real-world conversations. Get up to 60% off at https://babbel.com/torenberg -- TIMESTAMPS: (00:00:00) Episode preview (00:01:05) Introduction to Turpentine Finance Podcast (00:01:31) Meet Jody: The Radical CPA (00:03:06) The disconnect in accounting firms (00:05:53) Jody's journey into accounting (00:07:23) Innovating in a firm with technology and cloud solutions (00:12:58) Challenges in changing the pricing model (00:18:04) The role of automation in accounting (00:24:32) Innovative constraints in small firms (00:25:33) Realizing pricing as the core problem (00:27:20) Transitioning to value-based pricing (00:36:01) The role of AI and technology in accounting (00:37:41) The future of bookkeeping firms (00:39:56) Reimagining the accounting profession (00:43:04) Strengthening accountant-client relationships (00:47:39) Training the next generation of accountants (00:49:40) Conclusion and final thoughts

In this episode, Sasha sits down with Seema Amble, Partner at Andreessen Horowitz. Seema shares her research on the transformation of the CFO’s office, and how generative AI is powering financial teams. She discusses how AI can empower CFOs and finance teams to focus on strategic rather manual tasks, increasing client communication through automation, the impact of AI on valuations in service businesses such as law and accounting, and the progression from “service as a software” vs “software as a service”. Seema also discusses investing cycles, and how AI adoption in enterprise might follow the trajectory of other technologies, beginning with consumer adoption first.  -- 🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode RECOMMENDED PODCASTS: 🎙️1 to 100 | Hypergrowth Companies Worth Joining Every week we sit down with the founder of a hyper-growth company you should consider joining. Our goal is to give you the inside story behind breakout, early stage companies potentially worth betting your career on. This season, discover how the founders of Modal Labs, Clay, Mercor, and more built their products, cultures, and companies. Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw Apple: https://podcasts.apple.com/podcast/id1762756034 -- SPONSORS: NETSUITE 📈 NetSuite has 25 years of providing financial software for all your business needs. More than 36,000 businesses have already upgraded to NetSuite by Oracle, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you’re looking for an ERP platform head to NetSuite: http://netsuite.com/zen - NetSuite has extended a one-of-a-kind flexible financing program for a few more weeks. COMMANDBAR 🦾 Level up your ineffective website chatbot with CommandBar. CommandBar builds a new type of web assistant which delivers highly personalized responses, real time co-browsing, and can perform actions on behalf of the users. Learn how Hashicorp, Gusto, Freshworks and more use CommandBar at https://commandbar.com/moz BABBEL 🌐 Ready to achieve your 2024 goals? Start learning a new language with Babbel in just three weeks. Enjoy app lessons, live classes, and podcasts designed for real-world conversations. Get up to 60% off at https://babbel.com/torenberg -- LINKS: The CFO in Crisis: https://a16z.com/the-cfo-in-crisis-mode-modern-times-call-for-new-tools/ Death, Taxes, and Accounting: https://a16z.com/generative-ai-in-accounting/ X/SOCIAL @seema_amble (Seema) @sashaorloff (Sasha) TIMESTAMPS: (00:00:00) Introduction to Turpentine Finance Podcast (00:01:44) Discussing the CFO in Crisis Mode article (00:02:10) Challenges faced by CFOs with legacy software (00:06:35) The pyramid graph of finance team tasks and market insights (00:15:10) Generative AI's impact on finance (00:16:24) Emerging trends and changes in the market (00:20:14) The rise of bundled solutions in finance (00:22:49) Death, taxes, and AI: Transforming accounting (00:24:33) The excitement of AI in accounting (00:26:42) Challenges and opportunities in AI adoption (00:29:29) Incentive alignment and talent development in service businesses (00:32:36) The future of services as software (00:34:14) AI's impact on business models and valuation (00:38:17) Andreessen Horowitz's AI investment strategy (00:40:07) Future trends and predictions in AI (00:44:12) Engaging with Andreessen Horowitz (00:45:18) Conclusion and call to action

In this episode of Turpentine Finance, Sasha sits down with Dan Fletcher, CFO of Planful. They discuss how CFOs can build trust with the CEO and the board, balancing growth and profitability across different company stages, the nuances of working with VC versus PE investors, and more. Dan also shares his perspective of working at Planful, building infrastructure for CFOs. -- 🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode -- RECOMMENDED PODCASTS: 🎙️1 to 100 | Hypergrowth Companies Worth Joining Every week we sit down with the founder of a hyper-growth company you should consider joining. Our goal is to give you the inside story behind breakout, early stage companies potentially worth betting your career on. This season, discover how the founders of Modal Labs, Clay, Mercor, and more built their products, cultures, and companies. Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw Apple: https://podcasts.apple.com/podcast/id1762756034 -- SPONSORS: NETSUITE 📈 NetSuite has 25 years of providing financial software for all your business needs. More than 36,000 businesses have already upgraded to NetSuite by Oracle, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you’re looking for an ERP platform head to NetSuite: http://netsuite.com/zen - NetSuite has extended a one-of-a-kind flexible financing program for a few more weeks. COMMANDBAR 🦾 Level up your ineffective website chatbot with CommandBar. CommandBar builds a new type of web assistant which delivers highly personalized responses, real time co-browsing, and can perform actions on behalf of the users. Learn how Hashicorp, Gusto, Freshworks and more use CommandBar at https://commandbar.com/moz BABBEL 🌐 Ready to achieve your 2024 goals? Start learning a new language with Babbel in just three weeks. Enjoy app lessons, live classes, and podcasts designed for real-world conversations. Get up to 60% off at https://babbel.com/torenberg -- LINKS: https://planful.com/ X/SOCIAL: Dan Fletcher on Linkedin: https://www.linkedin.com/in/danfletchersf/ @sashaorloff (Sasha's X) TIMESTAMPS: (00:00) The best advice for growth and profitability (02:13) Meet Dan Fletcher: Navigating CFO challenges (02:57) Stakeholder management for CFOs (04:22) Building trust with the CEO (08:30) Growth vs. profitability: A balanced approach (17:28) Navigating M&A discussions (20:43) Preparing for board meetings (25:08) Common questions CFOs face (25:45) The importance of knowing your business (26:24) The role of the CFO in board meetings (27:22) Differences between venture-backed and private equity-backed boards (29:00) Career path to CFO: CPA vs. corporate finance (33:53) Essential skills for aspiring CFOs (35:04) The role of the controller in strategic finance (37:07) Planful's success and CFO insights (43:02) Future of AI in financial planning (45:28) Conclusion and final thoughts

In this episode, Sasha sits down with Nadia Asoyan, former CFO of Strike, Robinhood, and Controller at Square. Nadia shares her journey from EY to Silicon Valley's top fintech rocketships, offering invaluable insights on transitioning from accounting to CFO positions. She discusses the challenges of IPO readiness, the evolution of financial processes in fast-growth startups, and the delicate balance between growth and profitability. Nadia also provides candid advice for aspiring CFOs, emphasizing the importance of cross-functional partnerships and data literacy. 🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode -- RECOMMENDED PODCAST: 🎙️ Second Opinion - A new podcast for health-tech insiders from Christina Farr of the Second Opinion newsletter. Join Christina Farr, Luba Greenwood, and Ash Zenooz every week as they challenge industry experts with tough questions about the best bets in health-tech. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1759267211 Spotify: https://open.spotify.com/show/0A8NwQE976s32zdBbZw6bv 📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week. Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812 -- SPONSORS: NETSUITE 📈 NetSuite has 25 years of providing financial software for all your business needs. More than 36,000 businesses have already upgraded to NetSuite by Oracle, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you’re looking for an ERP platform head to NetSuite: http://netsuite.com/zen - NetSuite has extended a one-of-a-kind flexible financing program for a few more weeks. COMMANDBAR 🦾 Level up your ineffective website chatbot with CommandBar. CommandBar builds a new type of web assistant which delivers highly personalized responses, real time co-browsing, and can perform actions on behalf of the users. Learn how Hashicorp, Gusto, Freshworks and more use CommandBar at https://commandbar.com/moz BABBEL 🌐 Ready to achieve your 2024 goals? Start learning a new language with Babbel in just three weeks. Enjoy app lessons, live classes, and podcasts designed for real-world conversations. Get up to 60% off at https://babbel.com/torenberg -- LINKS: Strike: https://strike.me/ X/SOCIAL @sashaorloff @NadiaAsoyan TIMESTAMPS: (00:00) Introduction (01:06) Nadia’s Accounting Origins (04:17) Big Four Lessons (07:38) Square's Early Days (09:03) The Audit to In-House Transition (11:22) IPO Readiness at Square (17:05) Building Processes at Robinhood (18:21) Sponsors: Netsuite | CommandBar (21:00) Attracting Founders (24:30) Expanding Responsibilities (28:18) Evolving Processes (28:42) Sponsors: Babbel | Attio (32:33) Advice for Accounting Professionals (35:05) Board Management and Fundraising (42:00) Board Meetings (45:20) Growth vs. Profitability (48:32) Counterintuitive Advice (50:00) Misconceptions and Unsolved Problems (54:41) Square IPO Challenges (59:48) Complexity and Automation (1:04:10) Free Products and Hyper Growth (1:07:01) Pricing Models (1:10:22) Budget Setting (1:14:20 ) Wrap

In this episode, Tomer London, co-founder and Chief Product Officer at Gusto, shares insights into aligning product and finance teams for responsible growth. He dives deep into the frameworks and practices Gusto employed to make trade-offs between core products, expansion opportunities, and moonshot ideas - all while maintaining a relentless focus on customer needs and healthy unit economics. Tomer discusses Gusto's thoughtful, iterative approach to product development, avoiding the pitfalls of pursuing growth at all costs. He provides a candid look into Gusto's fundraising philosophy and managing the product-finance relationship through the company's evolution from startup to industry leader. 🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode -- RECOMMENDED PODCAST: 🎙️ Second Opinion - A new podcast for health-tech insiders from Christina Farr of the Second Opinion newsletter. Join Christina Farr, Luba Greenwood, and Ash Zenooz every week as they challenge industry experts with tough questions about the best bets in health-tech. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1759267211 Spotify: https://open.spotify.com/show/0A8NwQE976s32zdBbZw6bv 📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week. Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812 --- SPONSORS: ATTIO 📊 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 NETSUITE 📈 NetSuite has 25 years of providing financial software for all your business needs. More than 36,000 businesses have already upgraded to NetSuite by Oracle, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you’re looking for an ERP platform head to NetSuite: http://netsuite.com/zen - NetSuite has extended a one-of-a-kind flexible financing program for a few more weeks. COMMANDBAR 🦾 Level up your ineffective website chatbot with CommandBar. CommandBar builds a new type of web assistant which delivers highly personalized responses, real time co-browsing, and can perform actions on behalf of the users. Learn how Hashicorp, Gusto, Freshworks and more use CommandBar at https://commandbar.com/moz BABBEL 🌐 Ready to achieve your 2024 goals? Start learning a new language with Babbel in just three weeks. Enjoy app lessons, live classes, and podcasts designed for real-world conversations. Get up to 60% off at https://babbel.com/torenberg LINKS: gusto.com X/SOCIAL @sashaorloff @tomerlondon TIMESTAMPS: (00:00) Intro (01:25) Landing on Payroll (03:46) Payroll as a Wedge (05:20:)The Importance of Emotional Pain Points (07:23) Dream Big, Make it Real (13:06) The Three Horizons Framework (15:07) The Importance of Product & Finance Alignment (17:08) Sponsor: NetSuite | Attio (21:00) Milestones and Accountability (24:00) Killing Products (28:30) Staying Focused Amidst Competition (30:39) Sponsor: beehiiv | Babbel (34:00) Fundraising Strategy (36:46) Evolving Thinking on Profitability (40:25) The Power of Customer Connection (42:00) The Future of Gusto (43:12) 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

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 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.