Run The Numbers

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Run the Numbers is a weekly podcast about financial metrics and business models, designed for ambitious people operating tech startups. It's a collection of things host CJ Gustafson (CFO at Partstech and writer of Mostly Metrics) has learned and thought about in the trenches as a tech CFO. This show is meant to serve as a playbook of sorts for the stuff CJ wishes he knew earlier in his career, both from experience and from copying people smarter than himself. Topics frequently touch upon Startup SaaS Metrics, Annual Budgeting, Financial Forecasting, Headcount, Equity, Dilution, and Fundraising – and how all of these drive business performance and growth.

CJ Gustafson


    • Sep 15, 2025 LATEST EPISODE
    • weekdays NEW EPISODES
    • 49m AVG DURATION
    • 227 EPISODES


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    Latest episodes from Run The Numbers

    TikTok Will Beat Amazon, Google Is Going to Zero, and Other Wild Predictions With VC Turner Novak

    Play Episode Listen Later Sep 15, 2025 81:04


    Facebook is undermonetized, TikTok poses an existential threat to Amazon, and ChatGPT has probably already captured most of Google's high-value users. These are the opinions of today's guest, a venture capitalist deeply embedded in consumer networks and social product investing. In this episode, CJ chats with Turner Novak, the Founder and Managing Partner of Banana Capital, host of The Peel podcast, and a man who is known for his Twitter threads and podcast interviews as much as he is for his impressive portfolio. Turner breaks down the monetization models of some of the world's biggest platforms. Together, they discuss undervalued and overvalued business models, the long-term viability of subscription models, how platforms can identify and serve their highest-value users, and how to adapt acquisition strategies as AI reshapes the customer journey. Turner also reveals what excites him for future investments and the underestimated power of memes as a marketing tool.—LINKS:Turner Novak on LinkedIn: https://www.linkedin.com/in/turnernovakTurner Novak on X (@TurnerNovak): https://x.com/TurnerNovakBanana Capital: https://www.bananacapital.vcThe Peel: https://www.youtube.com/@ThePeelPodthespl.it: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(02:09) Sponsor – Rillet | Pulley | Brex(06:15) Turner's Embarrassing Accounting Story(08:10) How Turner Became an Accidental Influencer(09:02) Monetizing Content(12:22) How Turner Built His Media Platform(16:02) Sponsor – Aleph | RightRev | Navan(20:26) From Fantasy VC Portfolios to Podcasting(24:30) Turner's Main Business: Media Versus VC(25:42) Monetizing Premium Experiences on Social Products(30:27) Finding and Targeting High-Value Customers(32:27) Memes as a Tool for Marketing(36:10) Identifying High-Value Users and Opportunities(41:00) Why Pinterest Is Undermonetized(42:57) TikTok Versus Amazon for E-Commerce(46:30) Is ChatGPT Coming for Facebook and Google's Cash Flow(48:36) Facebook as an Undermonetized Business(54:24) The Long-Term Viability of Subscriptions(1:00:31) Customer Acquisition in a Platform-Dominated World(1:04:09) Paid Acquisition in the Era of AI(1:06:23) The Increasing Cost of CAC(1:08:59) What Turner Is Investing in Now(1:15:25) Doing Hard Things as a Moat(1:19:12) Wrap—SPONSORS:Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.#VentureCapital #BusinessModels #GoogleVsChatGPT #ConsumerNetworks #SocialCommerce This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    How Much Revenue Do You Need to IPO in 2025?

    Play Episode Listen Later Sep 13, 2025 22:21


    It used to be that if you built a good company, showed solid growth, and had decent unit economics, you could go public. But today? The bar has been raised—big time.Let's take a trip through the last ~15 years of tech IPOs to put today's market into context and zoom in on the most recent companies to go public.* 2010's: $100M is the Bar* 2021: The Year of the Mega IPOs* 2022-2023: The IPO Freeze* 2024: The Rebound – But With a Higher Bar* The New IPO PlaybookToday's podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you're curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don't miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You'll hear directly from industry leaders on how they're using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Humans, Robots, and Agents: UiPath on Agentifying Your Business in the Age of AI

    Play Episode Listen Later Sep 11, 2025 71:34


    Is it too soon to leverage agentic automation to drive AI transformation, streamline workflows, and boost productivity in finance? And how do you calculate the ROI of AI? Today's guest runs a high-functioning finance team at a company that's at the forefront of AI, where bonuses are tied to AI adoption. In this episode, CJ interviews Hitesh Ramani, Deputy CFO and Chief Accounting Officer at UiPath. After sharing wisdom from his years at Deloitte on the “muscle memory” that a company needs pre-IPO and mistakes to avoid after going public, he explains how his company is using its own technology to transform the finance function. He breaks down the difference between agents, robots, and workflows, describing what each does and how they interact. The conversation covers what it's like to manage org charts that include humans and AI agents, how to hire for the future of tech-savvy finance teams, and UiPath's vision for near-autonomous finance operations. Hitesh also reveals real-world AI use cases inside UiPath and offers lessons learned on embracing AI as a powerful productivity partner while maintaining trust and governance.—LINKS:LINKS:Hitesh Ramani on LinkedIn: https://www.linkedin.com/in/hitesh-ramani-a4a78118/UiPath: https://www.uipath.comMeghan Curtin McKenna: https://www.linkedin.com/in/meghan-curtin-mckenna-%F0%9F%94%A5-66a5022b/ FIF Collective: https://www.fifcollective.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:(00:00) Preview and Intro(02:04) Sponsor – Pulley | Brex | Aleph(06:19) Going Public Versus Being Public(09:50) The Need for a Company-Wide Operating Rhythm Pre-IPO(12:30) Top Mistakes To Avoid Before Going Public(16:01) Sponsor – RightRev | Navan | Rillet(20:06) Common Foot Faults After Going Public(23:57) Robots Versus Agents(30:17) RPA Versus AI(31:09) Agents & Workflows(34:05) Accountability: Outsourcing Your Agency(39:46) How To Measure ROI on AI(45:06) Scaling With Robots & Agents(48:15) Budgeting for People and Automation(50:41) High-Impact Versus Low-Impact Ideas in AI Implementation(53:36) Hiring & Developing Tech-Savvy Finance Talent(57:36) Build Versus Buy & Building an Autonomous Workflow(1:00:15) The Future of Autonomous Finance(1:01:14) Use Cases for AI at UiPath(1:03:18) Long-Ass Lightning Round: A Career Mistake(1:04:25) Advice to Younger Self(1:05:58) Finance Software Stack and the Future of In-House Systems(1:10:14) Craziest Expense Story—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.#AutonomousFinance #IPOJourney #AIinFinance #FutureOfFinance #AIAdoption This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Selling Your Company? A Silicon Valley Lawyer's Guide to Not Getting Screwed Over

    Play Episode Listen Later Sep 8, 2025 62:27


    How do founders and finance leaders prepare for the sale of their company when the other side of the negotiating table does this every day? In this episode, CJ interviews David Siegel, Partner at Grellas Shah LLP, a Silicon Valley law firm that guides some of the biggest names in tech through their most significant raises and exits. David shares insights from countless deals, revealing what it really takes to prepare for a sale, negotiate with buyers, and manage conflicting advice from bankers and lawyers. He unpacks investor dynamics, deal timelines, and why the $150 million to $350 million valuation range is the “awkward middle.” The conversation also covers how companies can de-risk themselves before going to market, how to spot a bad banker, what critical pitfalls to avoid in Letters of Intent (LOIs), the emotional realities founders face when selling their “baby,” and the shifting power dynamics in today's M&A landscape.—LINKS:David Siegel: https://www.linkedin.com/in/david-siegel-a271265Grellas Shah: https://grellas.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(02:06) Sponsor – Brex | Aleph | RightRev(06:41) The Average Time To Close M&A Deals Today(10:55) How To Start the Process of Selling a Company(13:09) Being Realistic About Your Valuation(15:13) Sponsor – Navan | Rillet | Pulley(19:08) VCs Versus Acquirers(20:12) The $150 Million to $350 Million Valuation Awkward Middle(23:17) Investor Behavior and Founder Incentives in Deals(24:59) The Banker Versus Relationship Route in Selling(27:46) What Makes a Bad Banker(28:43) PSA: Investment Banker Engagement Letters Are Negotiable(34:43) LOIs: What Sellers Should Push To Include Before Signing(39:43) What To Prioritise as a CFO in an LOI(43:21) The Worst Case Scenario for Vague Networking Capital Targets(46:22) De-Risking Your Company in the Eyes of an Acquirer(49:17) How Acquirer Risk Aversion Derails Deals(52:07) The Emotional Impact of Selling a Company(55:32) The Rules of Negotiation(57:19) Current State of M&A in Tech(1:01:30) Wrap—SPONSORS:Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.#TechAcquisitions #AcquisitionLaw #StartupExit #MergersAndAcquisitions #ExitStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Do PE Companies Trade Innovation for Margins?

    Play Episode Listen Later Sep 6, 2025 8:51


    Do PE Companies Trade Innovation for Margins?Private equity firms love to talk about operational excellence… but when “efficiency” comes at the cost of innovation, are they mortgaging tomorrow for today's margins?In this episode I break down why 25% operating margins became the magic number in software, how PE-backed businesses chase the Rule of 50, and what happens when cutting R&D tips companies into the “Innovation Death Spiral.”Today's podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you're curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don't miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You'll hear directly from industry leaders on how they're using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    From Facebook's Hypergrowth to Daffy's Disruption: A CFO's Playbook for Saying Yes

    Play Episode Listen Later Sep 4, 2025 71:19


    How do finance leaders enable growth while fostering a culture of partnership, positivity, and saying yes? In this episode, CJ interviews Ed Park, Head of FP&A at Facebook during its explosive hypergrowth years, Head of Finance and Internal Operations at Asana, the current CFO of Daffy, and a “glass-half-full” finance leader. Ed shares stories about working at Facebook in the early days, how he brought finance into the company's engineering and product-first culture, and how he built trust while navigating rapid user and infrastructure expansion. He talks about his role at Asana, why the company plans in episodes, not quarters, how they discovered their unique “three user” metric, and how they transitioned from bottoms-up to sales-led growth. Ed also gives an introduction to donor-advised funds and how Daffy, his current company, is disrupting this field. The conversation covers how a company's business model shapes its destiny, finding the balance between what's urgent and what's important, and Ed's glass-half-full approach to being a finance leader who enables teams by saying yes.—LINKS:Edward Park on LinkedIn: https://www.linkedin.com/in/edwardyparkDaffy: https://www.daffy.orgCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:Big Systems Thinking for Building a Finance Org: Advice From a Zoom Hypergrowth Survivor — —TIMESTAMPS:(00:00) Preview and Intro(02:16) Sponsor – Aleph | RightRev | Navan(06:43) Ed's First Job at a Startup: Head of FP&a at Facebook(11:35) Bringing Finance Into an Engineering and Product-Led Culture(16:42) Sponsor – Rillet | Pulley | Brex(20:34) Balancing What Was Urgent Versus Important(25:02) Monetizing Facebook(26:48) Becoming a Glass-Half-Full Finance Leader(33:27) Managing Four Chefs at Asana(35:38) How Asana Plans in Episodes, Not Quarters(42:48) Monetization Model Intuition and the “Three User” Metric(48:13) Transitioning From Bottoms-Up to Proactive Sales at Asana(53:24) Daffy's Monetization Model and Donor-Advised Fund Innovation(57:34) How a Business Model Shapes Destiny(1:00:02) Ed's “How Might We” Approach to Being a CFO(1:01:56) Long-Ass Lightning Round: A Big Mistake(1:04:38) Advice to Younger Self(1:05:44) Finance Software Stack(1:07:57) Craziest Expense Story—SPONSORS:Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics#FacebookBusinessModel #FPandA #StartupFinance #MonetizationStrategy #DonorAdvisedFunds This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    The Anti-Exit Strategy: Premji Invest's Approach to Evergreen Capital (& the Future of CFO Tech)

    Play Episode Listen Later Sep 1, 2025 53:59


    Premji Invest is an investment firm that backs some of the biggest names in the CFO and enterprise tech stack, including Anaplan, Zuora, Coupa, and Looker. In this episode, CJ is joined by Sandesh Patnam, the firm's Managing Partner, to discuss their approach to investing and the future of CFO tech. Sandesh talks about the evergreen nature of Premji's investment model and explains how this permanent pool of capital enables the company to focus on deep partnerships and durable growth, rather than chasing fund cycles or portfolio diversification. He breaks down why he views total addressable market (TAM) as a floor rather than a ceiling, how investing across both public and private markets creates a strategic advantage, and how startups should approach capital construction and optionality in today's market. The conversation also touches on the evolution of the CFO toolkit, how AI is shifting the finance role, what persistent finance problems are still waiting for innovation, how org design is changing inside finance teams, and why he believes AI is a bigger shift than both the dot-com and mobile eras.—LINKS:Sandesh Patnam on LinkedIn: https://www.linkedin.com/in/sandeshpatnamPremji Invest: https://in.premjiinvest.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:BlackRock Managing Director on the Secrets of Durable Companies - —TIMESTAMPS:(00:00) Preview and Intro(02:08) Sponsor – RightRev | Navan | Rillet(06:59) Evergreen Capital and Premji's Approach to Investing(09:25) Portfolio Construction(12:58) TAM Versus SAM Versus Product(15:28) Sponsor – Pulley | Brex | Aleph(19:51) Seats Versus Outcome-Based Pricing(23:30) Defining Durability(26:31) Public Versus Private Investing(28:44) Why One Team Manages Both Public and Private Investing(30:47) Capital Construction for CFOs With Evergreen Investors(32:13) How and When Evergreen Funds Seek Liquidity(35:32) Building Optionality in Capital Strategy Amid Market Changes(38:01) Secondary Markets in the Private World(41:39) The Evolution of the CFO Tech Stack(43:41) AI and Systems of Action(45:43) How CFOs Are Starting To Interact With AI Tech(49:09) A Finance Problem That's Open for Innovation(50:25) The Evolution of the CFO's Role Beyond Finance(51:33) The AI Era vs. Prior Tech Eras—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run#EvergreenCapital #PremjiInvest #CFOTechStack #InvestmentStrategy #PortfolioDurability This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Netskope IPO: S1 Breakdown

    Play Episode Listen Later Aug 30, 2025 24:48


    Cybersecurity company Netskope has filed to go public on the NASDAQ.Today we're breaking down their S1 filing, including their financials, valuation outcomes, and potential red flags.Today's podcast is brought to you by Campfire.You may know that we use Campfire as our ERP, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick and painless, and it's freed us up to focus on strategic work instead of manual processes. In case you don't know, Campfire is an AI-first ERP powering next-gen finance & accounting teams. Helps you close fast, unlock insights and scale smarter.If you're curious about where finance tech is heading, and would like to hear more of my thoughts on the topic, don't miss Campfire's Finance Forward AI Summit - the upcoming summit bringing together the sharpest minds in finance and operations.You'll hear directly from industry leaders on how they're using AI to shape the future of finance, and how your team can get ahead of the curve. I'll be speaking on panels with finance leaders from Anthropic, Snowflake, Mercury and more. The summit is October 28th in San Francisco; I hope to see you there.Sign up for the summit at campfiresummit.ai or learn more about Campfire at www.campfire.ai. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    From Karaoke With Benioff to the Death of SEO: Alex Konrad on the Business of Media

    Play Episode Listen Later Aug 28, 2025 72:13


    The media landscape is noisier than ever. How can founders and business leaders get their stories heard? And in an age of AI-driven content, how can creators distinguish themselves and build a direct relationship with their audience? In this episode, CJ sits down with Alex Konrad, a longtime tech journalist, former Forbes editor (responsible for curating the renowned Forbes 30 Under 30, Cloud 100, and Midas lists), and founder of Upstarts, a newsletter covering startups, venture capital, and the people shaping the innovation economy. Alex shares insider stories from his decade at Forbes, including how lists like the “30 Under 30” were created and what it was like profiling (and sometimes singing karaoke with) the likes of Marc Benioff, Satya Nadella, and Sam Altman. The conversation explores the evolving landscape of media, the business fund-raising announcements, how startups can actually work with journalists to shape perception, the rise of VC firms as media powerhouses, the shifting role of platforms like Substack and LinkedIn, why relationship-driven content will outlast the race to break news, and the death of traditional SEO.—LINKS:Alex Konrad on LinkedIn: https://www.linkedin.com/in/alexrkonradAlex Konrad on X (@alexrkonrad): https://x.com/alexrkonradUpstarts Media: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: LINKS MENTIONED:No Priors: AI, Machine Learning, Tech, & Startups: https://www.youtube.com/@NoPriorsPodcastLatent Space: https://www.youtube.com/@LatentSpacePodThe Daily: https://www.nytimes.com/column/the-daily52 Sourcery with Molly O'Shea https://www.youtube.com/@SourceryVCThe Information: https://www.nytimes.com/column/the-dailyRELATED EPISODES:“Let's Just See What Breaks” — Intuit's CFO on Being a Disruptor When You're Already the Incumbent - —TIMESTAMPS:(00:00) Preview and Intro(02:32) Sponsor – Navan | Rillet | Pulley(07:13) Building the Forbes 30 Under 30, Cloud 100, and Midas List(11:49) The Meme of SEC Trouble on Forbes List and a Media Tip(14:08) Why Lists Work So Well(17:17) Sponsor – Brex | Aleph | RightRev(21:57) What Might Convince Alex To Start a List(23:13) Karaoke With Benioff & Interacting With Billionaires(29:14) Entrepreneurship & Work-Life Integration(33:25) Sales Skills Alex Learned as a Founder(37:56) The Dance Behind Fundraising Announcements(42:30) How To Capitalize on the Media Outside of Funding Rounds(45:24) Examples of Founder “Oh S**t!” Moments(47:58) VC Firms As Media Companies(51:16) Non-Journalists Interviewing in Tech(55:02) Audience Relationship & Guarding Against AI(57:41) The Death of SEO(1:00:45) The Value of Time Sensitivity and News in the Era of AI(1:02:40) Platform Relationships & Substack(1:04:55) Bootstrapping Media & VC Pressure(1:10:55) Wrap—SPONSORS:Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. Visit https://navan.com/runthenumbers for your demo.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.#TechJournalism #MediaStrategy #AIinMedia #StartupPR #FutureOfMedia This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    “Stop Trying To Quantify Risk”: Risk Management Wisdom (& Star Wars Analogies) From CISO Andy Ellis

    Play Episode Listen Later Aug 25, 2025 66:13


    Cybersecurity risks have become more complex and unpredictable than ever, yet many companies struggle to quantify these threats in terms that truly matter. How can CFOs and CISOs effectively communicate about risk, make smart security investments, and navigate the emerging challenges posed by AI? In this episode, CJ interviews Andy Ellis, a renowned cybersecurity leader, former CISO of Akamai, investor, director, advisor, leadership coach, and author of the book 1% Leadership. Andy unpacks why most companies measure risk the wrong way and breaks down his "Pyramid of Pain” framework for categorizing it. He discusses the dynamics between CFOs and CISOs in purchasing security tools, demystifies security budgeting and vendor negotiations, dives into the evolving role of AI in security operations, and explains why the CISO and CIO roles are on a collision course. Andy also reveals insider stories from the frontlines of major breaches, shares a compelling risk analogy inspired by vampires and zombies, and clears up once and for all why the demise of the Death Star was not a failure of risk management.—LINKS:Andy Ellis on LinkedIn: https://www.linkedin.com/in/csoandyAndy Ellis on X: (@CSOAndy) https://x.com/csoandyWebsite: https://www.csoandy.com1% Leadership: https://www.amazon.com/1-Leadership-Master-Improvements-Leaders/dp/0306830817How to CISO: https://www.howtociso.comDuha One: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(02:49) Sponsor – Rillet | Pulley | Brex(07:23) Defining Risk: Technical & Human-Friendly Perspectives(09:20) Actuarial Risk Versus Human-Driven Risk(15:33) Why the Demise of the Death Star Wasn't a Failure of Risk Management(16:58) Sponsor – Aleph | RightRev | Navan(21:22) How the Death Star Metaphor Relates to Real-World Security Breaches(23:20) Why Risk Should Not Be Quantified in Dollar Terms(25:15) The Pyramid of Pain: Risk Severity and Surprise Levels(30:21) How CFOs and CISOs Should Partner on Security Purchases(34:03) Are Security Budgets Over or Under-Spent?(36:22) Balancing Budget for Security Tools and People(39:48) Tips for FP&As on Brokering the Security Budget With Your CISO(44:10) Factoring AI Uncertainty in a Three-Year Security Roadmap(46:38) AI Washing in Security Products and Realistic Impact(48:55) The Limitations of Security Operations(50:53) The Future of CIO and CISO Roles and Organizational Reporting(54:55) Why IT Shouldn't Report to the CFO(57:18) Israeli Unit 8200 and Cybersecurity Innovation(59:50) Startups Versus Public Companies: Differing Risk Models(1:02:52) Wrap—SPONSORS:Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.#Cybersecurity #RiskManagement #CISO #SecurityOperations #SecurityFinance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Are Fractional CFOs a Grift?

    Play Episode Listen Later Aug 23, 2025 9:17


    On average, I get asked 2x a week for fractional CFO recommendations.And on average, I get complaints 3x a week about someone's current setup.Today we investigate the booming fractional CFO market, and my checklist to making sure you get a good one.This week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    From $500M Losses to $500M Profits: The CFO Who Helped Major League Baseball Win off the Field

    Play Episode Listen Later Aug 21, 2025 80:56


    In 1997, the Florida Marlins won the World Series, but they also lost $30 million in the process. In 2002, only three Major League Baseball teams had positive EBITDA. Due to a dramatic collective bargaining agreement, five years later, only three clubs had negative EBITDA, and the MLB had gone from $500 million in losses to a $500 million in profit. Today's guest had a front row seat to the action. Jonathan Mariner is the former CFO of the Florida Marlins, the Florida Panthers, and Major League Baseball. He is also he founder of TaxDay and a seasoned board member on different boards, including Tyson Foods, OneStream, and Delaware North, among others. In this episode, he takes us inside the complex economics of pro sports. The conversation covers the surprising way sports franchises are actually valued, the massive shift from cable TV to streaming, the complex world of player merchandising, the challenges of expanding sports internationally, and how Jonathan helped implement a controversial EBITDA rule to rein in league-wide debt.—LINKS:Jonathan Mariner on TaxDay: https://www.taxday.com/team/Tax Day: https://www.taxday.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:The Boston Celtics' Other Playbook: Business Insights from President Rich Gotham — —TIMESTAMPS:(00:00) Preview and Intro(02:35) Sponsor – Pulley | Brex | Aleph(07:11) How Jonathan Became CFO of the Florida Marlins and Panthers(13:17) The Marlins: Winning the World Series and Losing $30 Million(16:03) Sponsor – RightRev | Navan | Rillet(20:08) How Not Having a Salary Cap Affects the MLB(21:27) The Collective Bargaining Agreement That Changed the Economics of the MLB(30:00) The Science of How Sports Franchises Are Valued: Revenue(31:53) The Art of How Sports Franchises Are Valued: Perception(36:20) How Local Broadcast Rights and Revenue Sharing Work(37:44) Contractually Obligated Income and Its Ramifications(41:57) How Player Jersey Sales Really Work(46:34) The Shift From Cable to Streaming and the Economic Effects(53:48) The Challenges and Opportunities of Global Expansion(59:57) Expansion Teams & Franchise Fees(1:01:58) Being on the Tyson Foods Board During COVID(1:05:39) Jonathan's Other High-Stakes Moments as a Board Member(1:08:03) Founding TaxDay(1:11:41) Long-Ass Lightning Round: Career Mistakes(1:14:00) Advice to Younger Self(1:15:11) The Best Sporting Events Jonathan's Ever Attended—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.#SportsFinance #MLB #MajorLeagueBaseball #TeamValuation #BusinessOfSports This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Inside the $5B Plaid Deal That Never Happened and the Massive Business Model Transition That Did

    Play Episode Listen Later Aug 18, 2025 66:10


    If you're curious about what it's really like to navigate a multibillion-dollar acquisition deal during a global pandemic, while under intense scrutiny of the Department of Justice, this episode is for you. Jason Pate, Chief Strategy Officer at Plaid, takes us behind the scenes of Visa's $5 billion bid to acquire Plaid and why it ultimately didn't happen. Jason also explains the massive evolution of Plaid from a linking infrastructure company to a thriving network business powering some of the biggest names in fintech. The conversation delves into the company's pivotal moments, including its recent $575 million fundraising round to solve for employee RSU liquidity. Beyond that, Jason shares lessons from his experience, unpacking the importance of understanding a customer's P&L, breaking down how to build durable fintech revenue streams through diversification, and offering candid insights on negotiation, the future of payments, and making big bets to fix something that isn't broken.—LINKS:Jason Pate on LinkedIn: https://www.linkedin.com/in/jason-pate-50735310/Plaid: https://plaid.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(01:43) Sponsor – Brex | Aleph | RightRev(06:08) Duke and “I Hate Christian Laettner”(07:45) Jason's Product Development Experience and Career Journey(10:38) The Importance of Understanding Your Customer's P&L(12:41) Plaid's Transition From Linking Infrastructure to Network Business(15:23) Sponsor – Navan | Rillet | Pulley(18:55) Building the Plaid Data Network and Ecosystem(25:41) Friction in Payments: Feature Versus Bug(27:46) The Future of Payments: Check-In Versus Checkout(31:21) Negotiations: Less Like Chess, More Like Marco Polo(35:21) Identifying Gives That Aren't Actually Gives(37:10) Plaid's Unsuccessful Acquisition by Visa(40:45) Being Interviewed by the DOJ During the Pandemic(43:49) Plaid's Recent Raise and the Unconventional Reason for It(47:00) Valuations: Fundraises Versus Sales(48:19) Building an Equity Program When Companies Stay Private Longer(50:48) Multi-Product Diversification: The Key to Durable FinTech Revenue(53:07) When & How To Transition From an Infrastructure to a Network Business(59:03) Jason's Philosophy on Ramping Team Members(1:01:04) Lessons From Roger Federer(1:02:52) Long-Ass Lightning Round: A Career Mistake(1:04:03) Advice to Younger Self(1:04:48) A Helpful Tactic for Negotiations—SPONSORS:Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.#Plaid #Fintech #acquisition #fundraise #employeeRSU #BusinessTransition This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Emergency Capital Markets Update: Stubhub IPO (Take 2)

    Play Episode Listen Later Aug 16, 2025 6:32


    What matters more: Your company performance, or market conditions?Stubhub is preparing to go public (again) after initially pulling the plug back in March of 2025. A lot has changed since then. The market is up. And their performance is down. We analyze what's going on in the capital markets, and how to think about what matters most when you're preparing to go public.(Read: Stubhub's original S1 breakdown on Mostlymetrics.com)This week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Thinking About Adding Payments to Your Software Product? Listen to This First!

    Play Episode Listen Later Aug 14, 2025 54:38


    If you're thinking about adding payments to your software company's tech stack, listen to this first. Today's guest knows that turning payments into a prolific growth engine isn't as simple as plugging in a processor; it's about knowing when you have the “right to win” and building the infrastructure, team, and go-to-market strategy to make it work. In this episode, Andrew Mosawi of JMI Equity and a self-named “dinosaur in the world of embedded payments”, joins CJ to unpack how embedded payments are reshaping industries, why certain platforms are perfectly positioned to own the payment flow, and when you're better off staying out of the game. They share the frameworks for sizing the TAM, deciding which vertical plays make sense, and forecasting revenue in a world where payments don't behave like SaaS, while also referencing real-world use cases. The conversation covers the common mistakes companies make when entering payments, standout examples of companies that have done this well, and the right and wrong questions you should be asking before starting out.—LINKS:Andrew Mosawi on LinkedIn: https://www.linkedin.com/in/andrewmosawi/JMI Equity: https://www.jmi.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: Companies mentioned:Mindbody: https://www.mindbodyonline.comBlackbaud: https://www.blackbaud.comToast: https://pos.toasttab.comShopify: https://www.shopify.comFlagship Advisory Partners: https://insights.flagshipadvisorypartners.comBCG “Fortune Favors the Bold: Global Payments Report 2024”: https://www.bcg.com/publications/2024/fortune-favors-bold-global-payments-reportRELATED EPISODES:The Art of Stacking S-Curves: Olo's Winning Vertical SaaS Strategy with CFO Peter Benevides - Efficiency Metrics, Management, and Consolidation - Tony Boor's CFO Playbook for Scaling Blackbaud - —TIMESTAMPS:(00:00) Preview and Intro(02:17) Sponsor – Aleph | RightRev | Navan(06:50) How the Payments Ecosystem Has Changed in the Last Two Decades(09:02) The Inflection Point That Brought Payments Into the Mainstream(10:23) The Size of the Payments Pie in 2025(11:49) Why Not Every Company Should Do Payments(14:23) What Makes a Company Well-Positioned To Offer Payments(15:50) Sponsor – Rillet | Pulley | Brex(19:42) Having a Strategic High Ground To Offer Payments(21:35) The Stickiness of Embedded Payments(24:14) What “Embedded Payments” Means(27:12) Different Models Used for Embedded Payments(32:14) A Typical Take Rate for Embedded Payments(36:45) The Accretive Nature of Embedded Payments and Other Benefits(40:14) The Next Phase of Payments: Other Finance Solutions(44:56) CJ's Mental Model for Assessing Payments at PartsTech(47:45) Running a Payments Function Versus a Traditional Software Function(50:46) Sales Dynamics: Traditional SaaS Versus Payments(52:01) Companies That Have Done Embedded Payments Well(53:05) The Right and Wrong First Questions To Ask Before Starting in Payments—SPONSORS:Aleph automates 90% of manual, error-prone busywork, with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. Visit https://navan.com/runthenumbers for your demo.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics#EmbeddedPayments #payments #PaymentsInfrastructure #PayFac #PaymentsStrategy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Having Gone Through Sh*t Is an Asset: Yext CFO's Playbook for the Tough Times

    Play Episode Listen Later Aug 11, 2025 59:13


    With a decade of experience at Yext, a company now approaching half a billion in ARR, Darryl Bond has seen it through negative EBITDA margins, executive turnover, and company-wide resets. In this episode, he sits down with CJ to talk about his approach to the finance function, which involves prioritizing growth over compensation, tackling the messy problems head-on, making the hard P&L calls in the “grey zones,” knowing when to ask for help, and staying focused through the tough times. Darryl shares how he scaled from controller to CFO, and how, in the process, he made sense of the chaos, led with transparency, and built a high-impact finance function that doesn't just report the numbers, but also drives the business. He explains the role of systems and processes in scaling operations, the mistakes he made early in his management journey, and why relationship-building has been the real unlock in his career. They dive into building deal desks, what operational excellence really means, and capital allocation decisions that actually start with listening to the customer.—LINKS:Darryl Bond on LinkedIn: https://www.linkedin.com/in/darryl-bond-788b962a/Yext: https://www.yext.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:“Run Toward a Tough Market” — Developing the Hard and Soft Skills To Be a Great Finance Leader — —TIMESTAMPS:(00:00) Preview and Intro(02:49) Sponsor – RightRev | Navan | Rillet(06:54) The Reasons for Darryl's Career Loyalty(08:58) Prioritizing Learning Over Comp(11:09) What Yext and Its Finance Function Looked Like in 2015(15:40) Sponsor – Pulley | Brex | Aleph(20:03) Choosing Which Messy Problems To Take On(22:00) The Right Time To Create a Deal Desk(23:39) When To Bring General Counsel In-House(24:36) Asking for Help and Building a CFO Network(28:25) What Operational Excellence Looks Like in the Finance Team(31:11) Staying Focused Through Tough Times(35:39) Making the Hard P&L Calls In the “Gray Zone”(37:05) The Importance of Talking to Customers(38:30) A Guide to Communicating the Bad News(40:25) The Role of Systems and Automation in Gaining Control of the P&L(43:07) Capital Allocation Decisions: Yext's Two Recent Purchases(45:06) Build, Buy, or Partner(47:57) The Pros and Cons of Being a Sub-$1B Public Tech Company(49:38) How To Get (and Lose) Sell-Side Analyst Coverage(51:04) What Excites Darryl Most About Yext's Current Stage(53:13) Long-Ass Lightning Round: A Career Mistake(54:36) Advice to Younger Self(56:17) Finance Software Stack(57:42) Craziest Expense Story—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run#CFOLeadership #FinanceLeadership #FinanceStrategy #OperationalExcellence#BusinessTurnaround #CapitalAllocation This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    An Unholy Alliance

    Play Episode Listen Later Aug 9, 2025 7:46


    What do Whitey Bulger, FBI Agent John Connolly, AI and Venture Capitalists have in common? In today's episode we explore an unholy alliance between two forces that need each other—massive capital piles and foundational model companies that can actually absorb that capital.This week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    How To Win at Early-Stage Sales (With the Guy Who Helped Take Snyk From $0 to $100M+)

    Play Episode Listen Later Aug 7, 2025 64:41


    Are you building a sales org from scratch? Or rebuilding one in the middle of an AI boom? If so, this episode is your field guide. CJ sits down with Ethan Schechter, SVP of Global Sales and Customer Success at Qodo (and the guy who helped take Snyk from $0 to $100M+ in revenue), to talk about the wild days of early-stage sales leadership. Ethan shares how he navigates “basecamp” moments and the “smile” and “cry” days of year one. He explains his approach to hiring for a new org, building internal trust while over-communicating, designing incentive structures for the early days, trading dollars for speed through discounting, and staying competitive in the fast-changing era of AI. The episode ends with an entertaining roast of LinkedIn's cringe posts, from fake ARR math to self-given nicknames and beyond.—LINKS:Ethan Schechter on LinkedIn: https://www.linkedin.com/in/ethanschechterQodo: https://www.qodo.aiCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:A CFO's Guide to Understanding Sales Teams, featuring Snyk's Ethan Schechter — —TIMESTAMPS:(00:00) Preview and Intro(02:07) Sponsor – Navan | Rillet | Pulley(06:10) Ethan's Career as an Early-Stage Sales Leader and Understanding Equity(10:04) The “Basecamp” Mindset and Restarting Strong(12:33) Building Out Your Rules of Engagement(14:25) Sponsor – Brex | Aleph | RightRev(18:45) Navigating the “Smile and Cry” Days of Year One(24:03) Ethan's Approach to Hiring for a New Org(27:38) Building Trust With Founders as a New Sales Leader(30:19) Incentives: Creating a Commission Plan for the Early Days(34:10) Why You “Can't Divide Zero”: Handling Deal Splits(35:52) Other Early-Stage-Isms or Philosophies(38:52) Discounting at an Early-Stage Company(41:17) Selling in Today's Environment: Competitive Trap-Setting(44:47) Budgets for AI Products: Experimental ARR(45:50) Monthly Deals and Decision Cycles in the Current Environment(47:33) Remaining Competitive in the Era of AI(51:08) The Lighter (and Cringier) Side of LinkedIn(1:03:01) Wrap—SPONSORS:Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.#SalesLeadership #StartupSales #SalesStrategy #SalesCompensation #discounting This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    Your Company Is a Utility Function: Here's How to Pull the Right Levers

    Play Episode Listen Later Aug 4, 2025 66:03


    Have you ever tried running a business like it's a utility function? Today's guest has. CJ is joined by Michaela Lehr, a seasoned FP&A leader and former CFO of ActionIQ, who breaks down how CFOs can pull levers like growth, retention, margin, and cash runway to maximize value without blowing something up. Michaela explains how not all growth is created equal and why how you grow matters as much as how much you grow. She talks about gross margin as the most sensitive area of the P&L and how to communicate with engineers about their impacts on it. The conversation also covers the rise of “experimental recurring revenue” in AI-first products, why investors are obsessed with net dollar retention, the risks of over-servicing customers, looking out for your own finance team, and what it means to budget in the real world when everything changes after board approval.—LINKS:Michaela Lehr on LinkedIn: https://www.linkedin.com/in/michaela-lehr-2908996/ActionIQ: https://www.uniphore.com/actioniqCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: Loveable: https://lovable.devCanva: https://www.canva.comConcourse: https://www.concourse.co—TIMESTAMPS:(00:00) Preview and Intro(02:20) Sponsor – Rillet | Pulley | Brex(07:33) What It Means To Run a Company Like a Utility Function(10:45) An Example of Optimising for This Utility Function Regarding AI Spend(15:36) Sponsor – Aleph | RightRev | Navan(19:35) Less Visible but High-Impact Levers That Drive Revenue(22:15) Gating Headcount Based on Performance Milestones(25:09) Cloud Costs as a Hidden Lever(27:30) Why How You Grow Matters As Much as How Much You Grow(30:08) Professional Services as a Necessary Investment(32:43) What ERR (Experimental Recurring Revenue) Is(36:39) Margin As the Most Sensitive Area of the P&L(38:13) Communicating With Engineers About Gross Margin(41:56) Why Investors Care So Much About Net Dollar Attention(43:53) Making Sure Your Upsells Don't Mask a Churn Problem(44:40) What Over-Servicing Your Customer Looks Like(46:58) Why the “Just Give Me My Budget” Mindset Doesn't Work(49:23) Brokering the Budget With Execs in Real Time(51:38) Looking Out for Your Own Team as a CFO(56:26) The First Sign of an Erosion of Trust(59:50) Finance's Role in Upholding Capital-T Truth(1:01:31) Long-Ass Lightning Round: A COVID-Era Multitasking Mistake(1:02:06 ) Advice to Younger Self(1:04:07) Michaela's Favorite Finance Tool(1:04:17) Craziest Expense Story—SPONSORS:Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.#UtilityFunction #FPandA #BusinessStrategy #GrossMargin #NetDollarRetention This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    NEW DATA: Q2 Private Company Benchmarks

    Play Episode Listen Later Aug 2, 2025 11:51


    Today we're reviewing the state of the private markets using the NEW benchmarks released by Mostly Metrics. We surveyed our readers to see how their company's are doing… And it's tough to be a company between $5M and $25M in revenue right now.Three other things that stood out from the benchmarks this quarter:1️⃣ CAC Payback is up across the board. It's taking longer to earn back customer acquisition costs. AI is disrupting traditional search channels, and companies are building internal tooling instead of buying when it makes sense.2️⃣ Revenue is coming from existing bases. Net Dollar Retention is doing the heavy lifting — especially beyond $25M ARR. Expansion efficiency is becoming the key growth lever.3️⃣ Burn multiples keep falling. In reaction to expensive growth, capital efficiency is trending up. Even companies under $25M ARR are showing discipline.Get the whole 33 page report hereThis week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.mostlymetrics.com

    “Let's Just See What Breaks” — Intuit's CFO on Being a Disruptor When You're Already the Incumbent

    Play Episode Listen Later Jul 28, 2025 67:44


    How do you keep innovating and disrupting when you're already the incumbent? And how do you prevent a $200B+ company from becoming slow and complacent? In this episode, CJ is joined by Sandeep Aujla, CFO of Intuit, who shares how one of the world's largest software companies continues to operate with the agility of a startup. With QuickBooks, TurboTax, Credit Karma, and MailChimp all falling in the Intuit family tree, serving both consumers and businesses, Sandeep breaks down the company's platform strategy, explains how he tells a unified story across these product lines, and describes how he prioritizes capital allocation. He also talks about Intuit's efforts to leverage AI to improve internal efficiencies, insights into the ideal CFO-CTO relationship, tactics for saying no, the benefits of letting stuff break, and how finance helped uncover a major growth opportunity for Intuit in the mid-market. The conversation touches on the company's 25 golden metrics, why leap years and the Super Bowl affect revenue, and the lesson Sandeep learned from a $2 coffee.—LINKS:Sandeep Aujla: https://www.linkedin.com/in/aujla/Intuit: https://www.intuit.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: —TIMESTAMPS:(00:00) Preview and Intro(02:30) Sponsor – Pulley | Brex | Aleph(07:11) Sandeep's Career Journey at Intuit(09:41) The Stigma Around CFOs and Seriousness(11:01) Being the Disruptor When You're Already the Incumbent(14:04) Intuit: Software, Payments, or Services Company?(15:21) Sponsor – RightRev | Navan | NetSuite |(19:00) The Intuit Family Tree(20:14) Cross-Platform Network Effects(21:54) Telling a Unified Story Across Multiple Product Lines(25:24) How Finance Discovered a Mid-Market Growth Opportunity(28:56) Reducing Churn by Keeping Customers on Platform(31:04) How Small Businesses Are Evolving To Leverage Tech and AI(34:11) How Sandeep Prioritises Capital Allocation(37:17) Tactics for Saying No Gracefully as a CFO(39:39) The Benefits of Letting Stuff Break(43:10) Reinvesting Across the Business: Consumer Versus Business(45:36) The CFO-CTO Relationship in the Age of AI(49:45) Tracking Intuit's Target for Internal AI Efficiency(52:06) Surprising Usage Patterns: Leap Years, Game of Thrones, etc(53:15) The Different Use Cases for AI Internally(55:48) The 25 Golden Metrics That Matter(58:45) Leap Years and Other Surprising Things That Impact the Business(1:00:04) Long-Ass Lightning Round: A Deadline Mistake(1:02:04) Advice to Younger Self(1:03:48) Finance Software Stack(1:04:36) A Bonus Question: Printed Notes(1:05:17) Craziest Expense Story—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.#platformbusiness #innovation #disruption #CapitalAllocation, #FinancialSoftware Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    The Evolution of Software Pricing (A History Lesson)

    Play Episode Listen Later Jul 26, 2025 15:33


    Pricing and packaging has undergone a radical transformation since the early 1950s. And the clear through line is a changing unit of value and how it's tracked.Historically, the tech industry has undergone six waves of change.* Hardware + Software sold together* Software Sold for Hardware* Application Service Providers* Outsourced Infrastructure + SaaS* Usage Based Pricing* HybridWe'll walk through each evolution, and leave you with some tips for overcoming common pricing challenges in the age of AI.This week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai.Referenced on podcast:* Jason Kap's expert pricing consultancy: https://bluerocket.io/ Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    “Most Sales Reps Are Coin-Operated”: A Guide To Building Better Comp Plans

    Play Episode Listen Later Jul 24, 2025 72:48


    How do you build a sales culture where top performers are empowered and poor performers are not protected? In this episode, CJ is joined by Daniel Lentz, whose career has spanned sales, taking an e-commerce platform public during a global pandemic, and, interestingly, seminary. Daniel Lentz is the CFO of BigCommerce and an expert in designing comp plans that work. In this episode, he breaks down his approach to this and how to avoid the pitfalls that can easily discourage your salespeople. He explains how to align sales and marketing efforts, touching on multi-touch attribution models, before discussing why he focuses on input metrics over output metrics. The conversation covers the importance of having an operator-first mindset, the skill of having a BS detector, the challenges of navigating macroeconomic factors, the role of mentorship, and why teaching your team how the company actually makes money is the ultimate unlock.—LINKS:Daniel Lentz on LinkedIn: https://www.linkedin.com/in/daniel-lentz-5ba8134/BigCommerce: https://www.bigcommerce.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:Customer-First Finance: PagerDuty's Secret to “Small” Public Company Success — —TIMESTAMPS:(00:00) Preview and Intro(02:28) Sponsor – Brex | Aleph | RightRev(07:04) Daniel's Unconventional Career Arc(11:40) Being an Operator-First CFO(14:05) The Skill of Having a Good BS Detector(15:45) Sponsor – Navan | NetSuite | Pulley(19:16) Why People Make Things Sound More Complicated Than They Are(21:33) Transitioning From a Top Sales Rep to a Top Sales Leader(24:46) Daniel's Philosophy When Designing Comp Plans(28:53) A Hot Take on Capping Big Deals(35:01) Onboarding Great Sales Leaders(38:17) Multi-Touch Attribution Models(42:36) How Finance Can Reduce Sales Versus Marketing Turf Wars(44:52) The Metrics That Matter: Input Versus Output(47:30) Misdiagnosing Problems in SaaS Go-to-Market Models(49:00) Why Benchmarking Can Be Misleading(51:06) How Small Companies Can Compete With Big Companies(52:22) The Power of Explaining to Employees How the Company Makes Money(55:56) Why Daniel Doesn't Want Employees To Be Distracted by the Macro(57:19) Explaining Rational Interest Rates to Employees Under 30(59:24) How Mentorship Has Influenced Daniel's Career(1:01:12) Advice for Taking Investor Advice(1:03:04) Long-Ass Lightning Round: A Big Career Mistake(1:04:51) Advice to Younger Self: Careerism Is a Trap(1:06:49) Finance Software Stack(1:10:32) Craziest Expense Story—SPONSORS:Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.#SalesComp #SalesCompPlan #InputMetrics #SalesCulture #SalesLeaders Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Beat, Raise, Repeat: Former IBM CFO on Developing Watson, AI Automation & Financial Stewardship

    Play Episode Listen Later Jul 21, 2025 66:53


    In this episode, CJ is joined by Chris Greiner, CFO of Zeta Global and former CFO of IBM's analytics division, where he worked on AI during the development of Watson. He's had a front-row seat to the evolution of AI across industries. He's also on a 15-quarter streak of beat-and-raise performance in his current role. Chris breaks down how strong financial stewardship can be a launch pad for innovation, not a constraint, and unpacks his “Closest to code, closest to customer” philosophy. The conversation covers how to determine whether a company's data advantage is real or just storytelling, what Chris learned from cataloging every task in the finance org, and why some things are better left unautomated. He explains what's on his personal IPO pre-flight checklist, how and why Zeta Global tracks daily revenue, and the “hustle metric” as a predictor of good salespeople. He also shares many lessons and anecdotes from his time at IBM, including one where he played tennis with the Emperor of Japan.—LINKS:Chris Greiner: https://www.linkedin.com/in/chrisgreiner1Zeta Global: https://zetaglobal.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: RELATED EPISODES:Monetizing Community Engagement: The Business of Fitness with Strava CFO Lily Yang - Everything You Need to Know About Sales Rep Comp + Commissions Planning w Ryan Walsh, CEO of RepVue - —TIMESTAMPS:(00:00) Preview and Intro(02:22) Sponsor – Aleph | RightRev | Navan(06:28) Chris's Tenure at IBM During the Development of Watson(08:24) The Evolution of Chris's Relationship With Data and AI(11:40) Why “Showing Not Telling” Is Key in Finance and Investor Relations(12:56) A Company's Data Advantage: Real Versus Storytelling(15:07) Cataloging Tasks in the Finance Org To Identify Automation Opportunities(17:02) Sponsor – NetSuite | Pulley | Brex(20:53) Enabling Internal Data Exploration Without Conflicting Results(23:13) The One Thing Chris Refuses To Automate and Why(26:46) Forecasting: The Tension Between Trusting AI and Your Own Calculations(28:58) Zeta Global's 15-Quarter Beat-and-Raise Streak(31:40) Daily Pacing and Confident Forecasting(33:58) Sizing Up Zeta Global by Daily Active Users and Usage-Based Activity(36:50) Unexpected Predictors of Customer Behaviour(38:47) The “Hustle Metric”: The Best Predictors of Good Salespeople(43:05) Chris's IPO Preflight Checklist(45:49) Strong Financial Stewardship as a Catalyst, Not a Constraint(48:10) The Top Controls That a CFO Should Have Their Eye On(49:55) The Fallacy of Having To Choose Between Growth and Margin Expansion(53:26) Finance Teams: Closer To Code Versus Closer to Customer(55:47) Value-Based Pricing(57:42) Long-Ass Lightning Round: A Career Mistake(58:20) Making Friends With the Emperor of Japan(1:02:32) Advice to Younger Self(1:03:57) Finance Software Stack—SPONSORS:Aleph automates 90% of manual, error-prone busywork, with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. Visit https://navan.com/runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. Head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics#BeatAndRaise #CFOInsights #AIinFinance #AutomationInFinance #FinancialStewardship Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    The CEO's #1 Job: Capital Allocation

    Play Episode Listen Later Jul 19, 2025 14:23


    Today we're talking about capital allocation, and how it's one of the most powerful, yet least discussed, skills a CEO needs to learn.Every CEO has three core jobs:* Run a good company (Operations)* Tell a good story (Investor Relations)* Deploy capital effectively (Capital Allocation)Most CEOs focus 80% of their time on the first two. Yet it's the third, capital allocation, that often has the highest leverage and the least guidance.You can read more about this topic at lookingforleverage.comThis week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai. Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    “AI Might Be Coming for Your Job, but There's No Better Time To Be an Accountant”

    Play Episode Listen Later Jul 17, 2025 62:10


    If you're an accountant, AI might be coming for your job, but today's guest believes that there's never been a better time to be in the profession. CJ is joined by Scott Spiegel, the COO and former CFO of the American Institute of Certified Public Accountants (AICPA). He has decades of experience in finance and leadership at the intersection of business, mission, and membership. He breaks down how the accounting profession has changed and what skills you need to embrace in order to thrive in today's world. He also shares insights into the surprising overlap between accounting and sales, the soft skills required for a successful accounting career, and the business dynamics of nonprofits, which, contrary to public belief, can and do make money. He also tells the story about how he uncovered fraud before making his predictions for the future of accounting.—LINKS:Scott Spiegel on LinkedIn: https://www.linkedin.com/in/scott-spiegel-cpa/American Institute of Certified Public Accountants: https://www.aicpa-cima.com/homeCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:Netflix Co-Founder Shares the Secrets to Being a Great CFO - Scoring Big: The Playbook for Nonprofit Financial Success with USA Hockey CFO Kelly Mahncke - Budgeting Your External Facing Time as a CFO: Tipalti's Sarah Spoja - —TIMESTAMPS:(00:00) Preview and Intro(02:43) Sponsor – RightRev | Navan | NetSuite(07:21) An Intro to the AICPA(09:25) How the Accounting Path Has Changed in 20 Years(13:37) The Talent Crunch and the Relationship Side of Accounting(15:05) If You're an Accountant, Your Job Is Sales(16:02) Sponsor – Pulley | Brex | Aleph(20:12) The Relationship Side of Sales(23:00) Scott's Personal Product Market Fit at AICPA(24:55) Making Lateral or Downward Career Moves(27:39) Fighting for the Role You Want(30:48) Why Leaders Don't Have To Know All the Answers(33:57) A Nonprofit Can Make Money(36:16) How AICPA Has Changed the Way They Recruit for Talent(40:35) The Constraints That Come With Being a Nonprofit(42:41) No Mission Without Margin(44:35) AI in AICPA and the Accounting Industry(49:14) Keeping Your Job in the Era of AI(52:13) Stories About Fraud(55:57) How Fraud Has Changed Over the Past 5 – 10 Years(58:04) The Future of the Accounting Career Path—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit https://navan.com/runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run#accounting #AIAndAccounting #AICPA #FutureOfAccounting #FinanceCareers Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Don't Sign That Yet: Small M&A Mistakes That Can Cost You Big

    Play Episode Listen Later Jul 14, 2025 62:02


    M&A deals usually involve a vast amount of legal fine print, and small oversights can have very costly consequences. To help you navigate this, CJ is joined in this episode by Trey O'Callaghan, a partner in Tech, M&A, and Emerging Companies at Goodwin. Trey breaks down the strategic role M&A lawyers play throughout the deal process in terms of both legal and business advice to help avoid costly missteps. The conversation explores when to involve legal counsel, issues like sales tax and contractor classification, and common deal-killers such as IP ownership and unresolved co-founder disputes. Trey also explains why earn-outs are the most litigated part of M&A deals and how to handle them wisely. The discussion touches on the personal implications of M&A deals for CFOs and how to negotiate adequate compensation. Trey also covers non-compete and non-solicit agreements, and the importance of understanding working capital fluctuations.—LINKS:Trey O'Callaghan on LinkedIn: https://www.linkedin.com/in/trey-o-callaghan-3196896a/Goodwin: https://www.goodwinlaw.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.com—TIMESTAMPS:(00:00) Preview and Intro(02:12) Sponsor – Navan | NetSuite | Pulley(06:55) The Types of Law Trey Specialises In(10:08) When a Company Should Engage With an M&A Lawyer(16:52) Sponsor – Brex | Aleph | RightRev(21:24) Deals That Have Fallen Apart(24:15) Unpaid Sales Tax as a Common, Solvable Issue(25:27) Issues With Contractors and How To Solve Them(27:08) Problems With IP Ownership(28:37) Co-Founder Issues(29:43) The Most Litigated Part of M&A Deals: Earn-Outs(34:30) Choosing the Right Plan To Use To Sell the Company(37:11) Deal Fatigue(38:36) The TLDR on Earn-Outs(39:57) The Ideal Mindset for the CFO During the Deal Process(42:33) When and How To Negotiate Compensation as a CFO(47:55) Understanding Working Capital Fluctuations(52:25) Non-Competes: How They Work(56:34) Considerations for Non-Solicits(59:51) Closing Words for Anyone Doing an M&A Deal—SPONSORS:Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.#MandA #MergersAndAcquisitions #MandALawyer #earnouts #CFO Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    The Shrinking Public Markets, and Rise of Private Liquidity Loops

    Play Episode Listen Later Jul 12, 2025 14:33


    Over the past 30 years, the number of publicly traded companies in the U.S. has been sliced in half, falling from a peak of ~8,000 in the late '90s to just ~4,000 today.That stat shocked me. I knew IPOs were a slow drip, but I didn't realize that the number of companies being taken private was far out pacing the number joining the NYSE and NASDAQ ranks.Today we discuss:* Three structural changes in the capital markets that brought us to this point* The rise of private credit* How companies staying private changes your job as an operator or CFOThis week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai. Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    “Anything new needs to have AI core to its offering”: Amy Butte on How Navan Is Redefining Finance Ops

    Play Episode Listen Later Jul 10, 2025 64:26


    In the current tech landscape, everyone is experimenting with AI, but when it comes to finance, we tread more carefully. In this episode, CJ is joined by Amy Butte, the CFO of Navan, one of the most AI-forward travel and expense platforms in operation. Amy highlights how the company is weaving AI into its operating system, not just to summarize documents, but to manage financial workflows with real impact. With a career spanning Wall Street and Silicon Valley, Amy also discusses her journey from being the CFO of the New York Stock Exchange to her current role. She delves into her experiences as an audit chair and touches on the challenges and opportunities in building teams and navigating change. She also breaks down the dynamics of the build versus buy debate in the current tech space before sharing anecdotes about her unique experiences at the New York Stock Exchange and her perspectives on being a woman in leadership.—LINKS:Amy Butte on LinkedIn: https://www.linkedin.com/in/amybutte/Navan: navan.com/RunthenumbersExtraordinary Women on Boards: https://www.ewobnetwork.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.com—TIMESTAMPS:00:00 Preview and Intro02:59 Sponsor – MUFG | NetSuite | Pulley06:52 Conferences and Networking09:09 How Navan Has Implemented AI12:17 Whose Responsibility Is It To Drive AI Adoption14:50 The Risks Involved in Using AI in Finance15:50 Navan's New Bot “Miles”17:00 Sponsor – Brex | Aleph | RightRev | Navan22:31 The Operational and Financial Impact of Using AI at Navan23:36 CSAT Scores: Humans Versus Bots24:46 AI Within the Finance Department27:37 What an Audit Chair Does32:04 Using the Audit Chair Seat To Influence Business Outcomes33:33 Mentoring CFOs and Unlocking Opportunities As Audit Chair36:29 How To Become a Board Member or Audit Chair38:58 The Role of the Director Versus the Role of the Operator39:44 Building Teams and Empowering People48:48 Build Versus Buy in the Era of AI51:28 Partnering: Collaboration Versus Control53:07 A Story About the Security at the New York Stock Exchange55:36 Meeting the CEO of Merrill Lynch57:43 Leadership and Opportunities for Women in Finance1:00:37 Long-Ass Lightning Round: A Big Mistake1:01:31 Advice to Younger Self1:02:37 Finance Software Stack1:02:55 Craziest Expense Story—SPONSORS:MUFG is a global banking powerhouse that provides comprehensive banking services for VC-backed, PE-backed, and public companies with revenues starting at $40M. Accelerate your growth trajectory. Contact group head Bob Blee at bblee@us.mufg.jp to find out more.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.#Navan #AIFinance #FinancialTransformation #AuditChair #WomenInLeadership Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Inside the “PayPal Mafia”: One of the Most Influential “Seed Funds” in Tech History with Jimmy Soni

    Play Episode Listen Later Jul 7, 2025 77:01


    Elon Musk, Peter Thiel, Reid Hoffman, Max Levchin, David O. Sacks, Roelof Botha, Chad Hurley, Russel Simmons, and Jeremy Stoppelman are among those considered the “PayPal Mafia”. These are cofounders or early team members of PayPal who went on to found or invest in major tech companies like Yelp, Palantir, YouTube, Facebook, SpaceX, X, LinkedIn, Affirm, Airbnb, and others. In this episode, CJ is joined by Jimmy Soni, bestselling author of The Founders, which chronicles the early years of PayPal. He delves into some of the lesser-known aspects of PayPal's history. He sheds light on Peter Thiel's prediction of the dot-com collapse, why he advocated for the employment of Roelof Botha as CFO at the age of just 26, and his second-chance philosophy for hiring failures. The conversation covers PayPal's “frenemy relationship” with eBay, how they convinced their users to advocate for them, and pivotal moments that influenced their IPO and sale. Tune in for unique insights into one of the most important "seed funds" in tech history.—LINKS:Jimmy Soni on X (@jimmyasoni): https://x.com/jimmyasoniJimmy Soni on LinkedIn: https://www.linkedin.com/in/jimmysoniThe Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley: https://www.amazon.co.za/Founders-Paypal-Entrepreneurs-Shaped-Silicon/dp/1501197266CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:How Upwork CFO Erica Gessert Drove 20 Points of EBITDA Growth in Just 3 Quarters: —TIMESTAMPS:(00:00) Preview and Intro(02:12) Sponsor – Pulley | Brex | Aleph(07:40) Jimmy's Approach to Writing the Book(08:56) An Intro to the “PayPal Mafia”(10:57) The 1998 to 2002 Time Period(12:36) Present-Day Successes of “PayPal Mafia” Members(14:06) Challenges of Interviewing High-Profile Figures(16:06) Sponsor – RightRev | Navan | NetSuite(19:46) Comparisons to Other Influential Tech Groups(21:05) PayPal, YouTube, and the Embed Strategy(23:21) The Company's $20 Referral Program(27:10) Peter Thiel's Prediction of the Dot-Com Collapse(30:48) The Fallout From the Merger That Resulted in PayPal(33:00) The Evolution of PayPal's Business Model(36:58) The Unique Skillset That Roelof Botha Brought to the CFO Role(41:04)) Fraud-Fighting Techniques(43:26) PayPal's “Frenemy Relationship” With eBay(47:10) Challenges Faced by PayPal That Modern Fintechs Still Grapple With(49:13) How PayPal Made Its Users Advocates for the Business(53:44) PayPal's Talent Acquisition and “Misfits” Culture(56:54) Peter Thiel's Talent-Spotting Abilities and Second-Chance Philosophy(1:00:12) The Outcome of the eBay Sale(1:05:03) One of the Most Important “Seed Funds” in Tech History(1:08:07) Advice for Moving From Fast Work To Slow Work(1:11:18) Favorite Behind-the-Scenes Anecdote(1:13:04) The Most Underrated Member of the “Mafia”(1:14:04) One of the Most Pivotal Decisions Made(1:15:03) Wrap—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.#PayPalMafia #JimmySoni #CAPTCHA #PayPal #fintech Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    IPO Alert: Breaking Down Figma's S1 Filing

    Play Episode Listen Later Jul 5, 2025 18:09


    Figma Figma just raised the bar for IPOs in 2025.Today we break down their revenue, margins, retention, and potential valuation in the public markets.You can find the full analysis in written form at:https://www.mostlymetrics.com/p/figma-ipo-s1-breakdownThis week's podcast is brought to you by Campfire (www.campfire.ai)We've all used legacy ERPs. Painful migrations, endless consulting fees, and even after you're live, getting simple answers still means hours in spreadsheets.Campfire fixes that. It's the AI-first ERP built for modern finance and accounting teams. It's helping mid-market and enterprise teams close faster, unlock insights instantly, and scale smarter - without the additional headcount.I use Campfire myself, and it's been a game changer for our finance workflow. The interface is intuitive, migration was quick & painless, and it's freed us up to focus on strategic work.They just raised $35 million from Accel to further reimagine ERP. That's not easy to do.I'm excited to see how they keep reimagining this space – and you should be too.Check them out at www.campfire.ai. Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    The Modern CFO: Scott Engler on How To Master the Most Important Role in the Company

    Play Episode Listen Later Jul 3, 2025 79:12


    In many companies, the CFO is more important than the CEO. And the majority of private equity-backed CFOs are actually not up to par. In this episode, CJ is joined by Scott Engler, of LinkedIn fame, to explain why he believes these bold statements to be true. Scott is the CEO and co-founder of Sync Executive Partners and the co-founder of PE-Xcelerate. He has decades of experience studying, recruiting, and coaching CFOs. He shares insights on the evolving role of the CFO, the many hats they wear, and which they should prioritise. He gives advice on how to navigate your relationship with your CEO, your PE sponsor, and other stakeholders, and provides some social profiling hacks that can help. The conversation covers the benefits of upside-down reviews and why not having a recommendation can be the smartest move, before examining the best way to get a CFO job at a PE-backed company, and how to negotiate equity packages.—LINKS:Scott Engler on LinkedIn: https://www.linkedin.com/in/scottengler/Sync Executive Partners: https://www.syncexecutivepartners.com/PE-Xcelerate: https://www.pexcelerate.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comLooking for Leverage: RELATED EPISODES:So You're Looking for a “Strategic” CFO? Bloomerang's Steve Isom on What That Really Means - CFO of FloQast on Why Finance Teams are Data Curators: “What's in It for Me?” The Art of Storytelling in an IPO - with Monday.com CFO Eliran Glazer: Inside the "Triangle of Doom”: How Great CFOs Navigate CEO and Board Dynamics: —TIMESTAMPS:(00:00) Preview and Intro(02:20 ) Sponsor – Brex | Aleph | RightRev(07:12) How the CFO Role Has Changed Over the Last Decade(12:08) Why the CFO Needs To Drive the Pace(14:49) Why Most Private Equity-Backed CFOs Aren't up to Par(16:36) Sponsor – Navan | NetSuite | Pulley(20:07) The PE-Backed CFO Versus Hypergrowth VC CFO(21:54) How Senior Leaders Are Incented To Play It Safe(26:04) The Operational CFO: The CFO Becoming More of a COO(28:41) Why the CFO Is More Important Than the CEO(32:16) How a CFO Should Prioritize Their Many Roles(34:46) The Importance of Being a Good Storyteller(38:49) What an Upside-Down Review Is(43:46) Why Not Having a Recommendation Can Be the Smartest Move(49:50) The Hardest CFOs Are the Easiest To Influence(55:37) The Art and Science of Managing Your CEO(57:48) Social Styles Hack(1:00:47) Working With Your CEO and PE Sponsor(1:04:08) The Best Way To Get a CFO Job at a PE-Backed Company(1:11:54) The State of Comp for PE-Backed CFOs in This Market(1:13:16) Negotiating Equity Packages(1:15:39) The Biggest Challenge for PE-Backed CFOs Today—SPONSORS:Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.#CFO #CEOversusCFO #ChiefFinancialOfficer #PrivateEquity #ScottEngler Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    I sold a company, and then fired myself immediately

    Play Episode Listen Later Jun 28, 2025 42:29


    The number one thing listeners of the pod ask me for is to flip the script and let someone interview me. I've historically been reluctant to do it because it feels little self aggrandizing or whatever the term is. But you gotta give the people what they want.On this episode my friend Mike Wu, founder of Hire Frame, interviews me on my transition to full time content creation. We talk about* How I sold a company as CFO, and then fired myself immediately* Why having supportive partners in any entrepreneurial endeavor is the real key to success* How I came up with the idea for my second newsletter Looking for Leverage.Mike's a gracious host and shout out to him for letting me share this with my audience. Mike's Podcast: What Worked on Spotify | Apple | YouTubeMike's Company: Hire FrameRun the Numbers is brought to you by Zenskar.Zenskar is an AI-powered order-to-cash platform that automates billing, revenue recognition, and SaaS reporting — no spreadsheets, no engineering required. Built for modern B2B companies, Zenskar supports any pricing model: subscriptions, usage-based, or complex custom contracts.Step into the future of finance today. Visit zenskar.com/rtn and book a demo! Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Inside the CFO Tech Stack (and the Failure Museum): Insights From Norwest's Sean Jacobsohn

    Play Episode Listen Later Jun 26, 2025 48:00


    The CFO software ecosystem is highly fragmented and ripe for disruption. Sean Jacobsohn, partner at Norwest, has a front-row seat to the action: He's backed 10 companies selling to CFOs, while Norwest has invested in 20. Having identified 300 companies in 15 different categories operating in the space, he joins CJ to share takeaways from his market map of the evolving CFO software stack. They dig into what's driving disruption, how new players are challenging legacy systems, and what it takes for founders to stand out. The conversation spans everything from the staying power of spreadsheets to the debate between building for verticals versus horizontals, the future of FP&A, and how AI agents might reshape the stack. Sean delves into the dynamics of partnerships, outlining five key rules for successful collaborations. Additionally, he talks about his Failure Museum which showcases a collection of items representing failed products and companies, and breaks down what he has identified as the six forces of failure.—LINKS:Sean Jacobsohn on LinkedIn: https://www.linkedin.com/in/seanjacobsohnNorwest: https://www.nvp.comMarket Map: Reimagining the CFO Software Stack: https://www.nvp.com/blog/market-map-reimagining-cfo-software-stackFailure Museum: https://failure.museum/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:CFO of FloQast on Why Finance Teams are Data Curators: The $7 Million Wake-Up Call: Mastering Rebates for Profitability with Enable's Nick Rose: G2 CFO Chad Gold on Building A Durable Career as a Venture Backed Exec: —TIMESTAMPS:(00:00) Preview and Intro(02:04) Sponsor – Rippling Spend | Pulley | Navan(06:08) The Fragmentation of the CFO Tool Ecosystem(07:24) Advice for Founders on Deep Domain Expertise(10:39) Enable: Disrupting an Existing Solution Versus Creating a New Category(12:32) The Prevalence of Spreadsheets in the Current Ecosystem(13:39) Solutions Built for Verticals Versus Horizontals(16:24) Sponsor – NetSuite | Planful | Tabs(20:22) Vertical Software and the Move to the Cloud(22:17) The Likelihood of Consolidation by Incumbents in the Space(24:53) Developments in the FP&A Space(26:55) The Future of AI Agents in Finance(28:05) The Five Key Rules of Partnerships: Partner Fit(29:17) Entering New Markets(30:16) Enablement: The Importance of Training(32:28) Reciprocation(33:49) How Often the Little Guy Approaches the Big Guy in Partnerships(34:51) M&A in Partnerships(37:01) The Best Way To Form a Partnership(37:45) The Inspiration Behind the Failure Museum(39:14) The Six Forces of Failure(40:38) Falling out of Product-Market Fit(41:25 Examples of Failures From the Failure Museum(44:58) How the Failure Museum Informs Sean's Work at Norwest(46:12) The Magic of Pivoting—SPONSORS:Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.#CFOsoftware #marketmap #verticalSaaS #FPandA #FailureMuseum Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Big Systems Thinking for Building a Finance Org: Advice From a Zoom Hypergrowth Survivor

    Play Episode Listen Later Jun 23, 2025 56:41


    When the COVID-19 pandemic hit in March 2020, Zoom went from steady growth to hyperscale almost overnight, even generating a backlog of a million tickets. Sarah Riley was a finance leader in the company at the time. She joins CJ to talk about what she learned from the experience and how it impacted her in her current role as CFO of dbt Labs. She also explains the influence of Helmer's Seven Powers framework on her strategic decisions. The discussion covers how Sarah's evolved pricing models, and helped bring product-led and sales-led growth together into a single go-to-market strategy at dbt Labs. She breaks down how she uses big systems thinking to build out a finance org, how to create healthy off-ramps for pilots, and what's actually okay to break when “moving fast and breaking stuff”. She also touches on the current use cases for AI in finance and for turning your team from “doers to reviewers”.—LINKS:Sarah Riley on LinkedIn: https://www.linkedin.com/in/sarahjriley/dbt Labs: https://www.getdbt.com7 Powers: The Foundations of Business Strategy: https://7powers.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:Wasted Capital and Where to Find It: The CFO's Guide to Spoilage Levers Leakages: —TIMESTAMPS:(00:00) Preview and Intro(02:18) Sponsor – Pulley | Navan | NetSuite(05:53) Being at Zoom at the Start of the Pandemic(10:14) Challenges Caused by the Influx of Customers(14:06) Takeaways From Sarah's Time at Zoom: M&A and Build Versus Buy(15:49) Sponsor – Planful | Tabs | Rippling Spend(19:38) Taking Advantage of Your High Share Price for M&A(20:56) What dbt Labs Does(24:27) Pricing Evolutions at dbt Labs: Freemium and Open-Source(27:51) Seat-Based, Usage-Based, Hybrid, or Outcome-Based Pricing(30:27) Pros and Cons of a Free Component(32:17) Finance and Sales in dbt's Evolving Go-to-Market Strategy(34:09) The Evolution of dbt Labs' ICP(35:09) The Helmer 7 Powers Framework(40:39) Being a Big Systems Thinker While Building a Finance Org(44:16) Moving and Iterating Quickly: Creating Healthy Off-Ramps for Pilots(46:19) What You Can and Can't Break When “Moving Fast and Breaking Stuff”(47:32) The Current State of AI and Use Cases in Finance(51:20) Long-Ass Lightning Round: Boundary Definition(52:08) Advice to Younger Self(52:56) Finance Software Stack(55:20) Craziest Expense Story—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.#hypergrowth #7Powers #FinanceStrategy #bigsystemsthinking #GoToMarketStrategy Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Preparing for Google Zero

    Play Episode Listen Later Jun 21, 2025 13:32


    We're heading towards a world where Google not only stops sending us traffic, but uses our own content against us.In today's podcast we discuss how Google's incorporation of AI summaries into search is changing the shape of the search funnel. For those responsible for making resource allocation bets across their companies to drive new users, this is a fundamental shift.How are you preparing for it? And what are we seeing? Tune in.Run the Numbers is brought to you by Zenskar.Zenskar is an AI-powered order-to-cash platform that automates billing, revenue recognition, and SaaS reporting — no spreadsheets, no engineering required. Built for modern B2B companies, Zenskar supports any pricing model: subscriptions, usage-based, or complex custom contracts.Step into the future of finance today. Visit zenskar.com/rtn and book a demo!Referenced:* Link to The Rebooting newsletter* Link to The Rebooting Podcast “Google Zero” episodeWant a Run the Numbers or Mostly Metrics custom Yeti Mug? They're dope. Share mostlymetrics.com in a Slack of Teams channel with +25 members, screenshot it, and email it to me at cj@mostlymetrics.comI'll hook you up. Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    a16z's Alex Immerman on the Evolving Role of the CFO in the Age of AI

    Play Episode Listen Later Jun 19, 2025 56:02


    In this episode, Alex Immerman, partner at Andreessen Horowitz, joins CJ to discuss the CFO role and how it's changing in the era of AI. He explains what the components of a company's AI agenda the CFO should own, how and where it should be leveraged in an organization, and why, if you're preparing to go public, AI needs to be mentioned in your S-1. He breaks down how the financial landscape differs greatly between AI-native SaaS companies and traditional B2B SaaS companies in terms of retention curves and gross margins, and how this relates to the ever-important LTV to CAC metric. As someone who has worked with prominent CFOs and interviewed many for a16z's portfolio companies, Alex also describes the qualities of a great CFO, and shares his favorite interview question, before discussing CFOs, CEO, and board dynamics.—LINKS:Alex Immerman on X (@aleximm): https://x.com/aleximmAlex Immerman on a16z: https://a16z.com/author/alex-immermanAlex Immerman on LinkedIn: https://www.linkedin.com/in/immermanAndreessen Horowitz: https://a16z.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:So You're Looking for a “Strategic” CFO? Bloomerang's Steve Isom on What That Really Means: —TIMESTAMPS:(00:00) Preview and Intro(02:19) Sponsor – Navan | NetSuite | Planful(05:52) What Separates Good CFOs From Great Ones(11:56) Questions Alex Asks When Interviewing CFOs for Portfolio Companies(15:17) How CFOs Should Engage With Investors During the Hiring Process(17:22) Sponsor – Tabs | Rippling Spend | Pulley(22:22) What a Great CFO-Investor Relationship Looks Like(24:46) The CFO-CEO-Board Dynamic(28:27) How the Role of a CFO Is Changing in the Era of AI(31:41) AI-Native Company Versus Incumbent for Finance Category Leader(33:49) Components of a Company's AI Agenda That the CFO Should Own(38:39) Why the LTV to CAC Metric Is So Important to Investors(41:13) LTV to CAC by Sector(42:41) The Importance of Gross Margin Adjusting Your CAC Payback(43:21 Retention and Churn Patterns in AI-Native Companies(45:23) Gross Margin in AI-Native Companies Versus Traditional B2B SaaS(50:11) What It Takes To Be a Public Company-Ready CFO Today(53:58) How IPO Expectations for the CFO Have Shifted in the Past Few Years(55:05) Wrap—SPONSORS:Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.#AINativeSaaS #a16z #CFO #LTVtoCAC #AIinSaaS Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    The CFO As the Culture Leader: KPIs, OKRs, and Embracing Failure To Achieve Success

    Play Episode Listen Later Jun 16, 2025 59:26


    If you work for a software company, odds are that people make up 80-90% of your business's costs. Today's guest argues that in order to effectively manage a company's greatest asset, the CFO should be heavily involved in shaping the company culture. Bill Tole is the CFO of TrustRadius, a trusted platform where tech buyers find real reviews. He is skilled in creating structures around ambition and breaks down how TrustRadius creates and implements Objectives and Key Results (OKRs). He explains how they differ from KPIs, why they fail, and how to set aggressive but achievable goals. He discusses the Rule of 40 and why it's essential for the rest of the company to understand it. Bill also shares how CFOs can influence culture from a finance perspective and why a lack of failure is a cause for concern.—LINKS:Bill Tole on LinkedIn: https://www.linkedin.com/in/bill-tole-0a99789/TrustRadius: https://www.trustradius.com/15Five: https://www.15five.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:Less but Better: Miro's Justin Coulombe on the Power of Strategic Divestment in SaaS: —TIMESTAMPS:(00:00) Preview and Intro(02:15) Sponsor – NetSuite | Planful | Tabs(06:00) TrustRadius's Business Model(09:20) OKRs at TrustRadius and Finance's Role in Them(14:07) Finance's Role in Asking the Stupid Questions(15:58) Sponsor – Rippling Spend | Pulley | Navan(20:10) How To Set Aggressive but Achievable Goals(23:19) The Ideal Number of OKRs(24:21) Leaving Room for Failing or Innovating(25:57) OKR Derivatives at Department Level(27:36) Why OKRs Fail(28:55) Rewriting or Killing Off an OKR Mid-Way(29:51) Where To Track Your OKRs(32:03) Applying the Rule of 40(34:39) Educating the Org on the Rule of 40(37:34) EBITDA Versus Free Cash Flow for Calculating Rule of 40(39:24) The CFO As the Culture Leader(43:21) Using Money To Change the Culture in a Positive Way(45:42) Mistakes CFO's Make When It Comes to Culture(47:06) Long-Ass Lightning Round: Why Failure Is Okay(51:41) Advice to Younger Self(53:44) Finance Software Stack(55:12) The State of SaaS Fragmentation or SaaS Sprawl(57:28) Craziest Expense Story—SPONSORS:NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.#failure #companyculture #OKR #KPI #Ruleof40 Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Saying the quiet part out loud

    Play Episode Listen Later Jun 14, 2025 9:18


    This one's for anyone who's ever mistaken SaaS metrics for gospel. I sit down (ok, dine out) with two CFOs—one from a dating app, the other from an HVAC parts company—and come away questioning the whole tech-is-king narrative.Turns out, the guy replacing dirty rugs in Georgia public schools pulled in $22 million last year. And no, he doesn't have a Substack.In this episode:* A billion-dollar business that makes… bolts* SaaS dreams vs. rug-cleaning realities* The myth of “build it once, sell it forever”* Why R&D is just COGS in a costume* A gentle roast of hustle culture and spreadsheet empiresThis is a reminder that while tech has its perks, the world is full of quiet, profitable businesses that don't require churn curves or pitch decks. Sometimes, the best margins come with dirt under the fingernails.Run the Numbers is brought to you by Zenskar.Zenskar is an AI-powered order-to-cash platform that automates billing, revenue recognition, and SaaS reporting — no spreadsheets, no engineering required. Built for modern B2B companies, Zenskar supports any pricing model: subscriptions, usage-based, or complex custom contracts.Step into the future of finance today. Visit zenskar.com/rtn and book a demo! Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Customer-First Finance: PagerDuty's Secret to “Small” Public Company Success

    Play Episode Listen Later Jun 12, 2025 64:30


    When PagerDuty went public in 2019, it was generating just $100 million in annual revenue which made it relatively small for a SaaS IPO. One of the main motivations for this was that visibility into the company's financials would inspire customer trust. In this episode, CJ speaks with Howard Wilson, PagerDuty's CFO, who shares the unique challenges of going public as a small company, how the landscape has changed since then, and how to approach an IPO when you don't have the experts you need in-house. As a former chief commercial officer, Howard brings unique insights into the role of a CFO. He discusses the importance of building a finance team with customer awareness, how he uses customer usage patterns to challenge traditional SaaS metrics, and how to uncover the unexpected pathways that customers take to reach your business. He also talks about the complexities of the “beat and raise" forecast, how market volatility creates opportunity, and breaks down his framework for mapping out potential investment areas.—LINKS:Howard Wilson on LinkedIn: https://www.linkedin.com/in/howardwilson01/PagerDuty: https://www.pagerduty.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.com—TIMESTAMPS:(00:00) Preview and Intro(02:08) Sponsor – Planful | Tabs | Rippling Spend(06:01) Earnings Calls and Being a Public Company CFO(11:14) How the Bar for Going Public Has Changed Since 2019(14:04) How Going Public Affects Customer Trust(15:50) Sponsor – Pulley | Navan | NetSuite(19:34) Approaching the IPO Process Without the Necessary Experts In-House(21:47) Using Advisors To Fill Functional Gaps in Small Companies(24:38) The IPO Tech Stack for Small Companies(25:44) The Complexities of the “Beat and Raise” Forecast(28:33) How Market Volatility Creates Opportunity(34:37) How Experience as a Chief Commercial Officer Makes a Better CFO(38:16) A Framework for Mapping Out Potential Investment Areas(44:08) Customer Awareness in Your Finance Organisation(47:47) Customer Usage Patterns Versus Traditional SaaS Metrics(52:16) The Unexpected Pathways Customers Take To Reach Your Business(57:54) Long-Ass Lightning Round: A Learning Mindset(59:22) Advice to Younger Self: Don't Stay in Your Lane(01:01:24) Finance Software Stack(01:02:57) Craziest Expense Story—SPONSORS:Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.#goingpublic #SaaSIPO #CustomerTrust #CustomerAwareness #PagerDuty Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    From $30M to Almost $1B: A Guide to Hypergrowth, IPO Prep, and Navigating the Public Market

    Play Episode Listen Later Jun 9, 2025 66:33


    How do you know when a company is ready to go public? And what do you do to prepare for this? Chirag Shah, CFO of Motive and former CFO of Kong and Cornerstone OnDemand, joins CJ to share insights from his experience of scaling businesses from $30 million to nearly $1 billion and tripling ARR. He talks about taking companies public and how he helped take one private again in a $5.2 billion deal. In this episode, he explains what signals indicate that a company is ready to accelerate its growth, the art and science of building sales capacity, and how to balance efficiency and growth in hypergrowth mode. He also covers how to achieve a great valuation without a strong performance, the biggest headache on the road to IPO, and whether you should IPO in the first place or remain private.—LINKS:Chirag Shah on LinkedIn: https://www.linkedin.com/in/chirag-shah-787b1b20/Motive: https://gomotive.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.com—TIMESTAMPS:(00:00) Preview and Intro(02:11) Sponsor – Tabs | Rippling Spend | Pulley(06:25) Personal Product Market Fit: Preparing Companies for IPOs(10:34) How Being a General Manager Made Chirag a Better CFO(15:02) Sponsor – Navan | NetSuite | Planful(18:11) Asking Better Questions in Finance(20:08) Signals That a Company Is Ready To Accelerate Its Growth(25:10) The Art and Science of Building Sales Capacity(28:35) The Dangers of Adding Too Many Sales Reps(33:22) Determining the Numbers of Recruiters and Sales Manager Interviews(35:03) How To Garner a Great Valuation Without a Strong Performance(37:18) The Sweet Spot for Earnings Guidance(41:22) The Biggest Headache on the Road to IPO(44:03) Underappreciated Challenges of Being a Public SaaS Company(46:42) Taking Cornerstone OnDemand Public and Then Private Again(50:17) IPO or Stay Private: Advice for CFOs(52:15) Optimizing for Public Company Holders Versus Private Equity Investors(55:05) Balancing Efficiency and Growth in Hypergrowth Mode(58:34) Long-Ass Lightning Round: Preparation for Being a CFO(01:01:34) Advice to Younger Self(01:04:04) Finance Software Stack(01:05:01) Craziest Expense Story—SPONSORS:Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.#scaling #goingpublic #hypergrowth #IPO #PrivateVersusPublic Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Bet on Yourself, and Putting in "Time on the Board" (CJ gets interviewed)

    Play Episode Listen Later Jun 7, 2025 51:04


    The tables are turned: CJ is interviewed by Lilly Wyden, host of the Shared Narratives podcast, to talk about the intersection of tech, finance, and writing.We discuss:* How I found a CFO job via my newsletter* The power of owning specific patches of real estate on the internet* If big Substack writers will have talent agents someday* How the memeification of finance has made the industry more fun and approachable* Whether I would ever write about corporate gossip or finance junk food* What types of products I might launch in the future, and more.Subscribe to Lilly's podcast: https://feeds.acast.com/public/shows/67dc51a1f48da98092cff738And subscribe to her Substack where you can also get her podhttps://sharednarratives.substack.com/Run the Numbers is brought to you by Zenskar.Zenskar is an AI-powered order-to-cash platform that automates billing, revenue recognition, and SaaS reporting — no spreadsheets, no engineering required. Built for modern B2B companies, Zenskar supports any pricing model: subscriptions, usage-based, or complex custom contracts.Step into the future of finance today. Visit zenskar.com/rtn and book a demo! Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Wasted Capital and Where to Find It: The CFO's Guide to Spoilage, Levers & Leakages

    Play Episode Listen Later Jun 5, 2025 59:43


    How can finance leaders identify where their capital is silently going to waste and where it can be better used to drive growth? In this episode, CJ interviews Russell Lester, the CFO of Tropic, where capital allocation is both the product and the mission. Russell introduces the concept of “spoilage”, deployed capital that fails to deliver its intended value. He also talks about “levers”, positive actions that force multiply your efforts, and “leakages”, headwinds or detractors that sap momentum. Russell believes it is the job of the CFO (or “Chief Alignment Officer”) to proactively go looking for these levers and leakages. He then explains how he uses his "center of the table" framework to redeploy the freed-up capital to fuel growth. Russell also covers how to address misalignment, what helicopter skills are and why you need them, what a data safari is and why you should take one daily, and why every CFO needs a spend management tool.—LINKS:Russell Lester on LinkedIn: https://www.linkedin.com/in/russell-lester-aa98463/Tropic: https://www.tropicapp.io/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:The Roadshow, the IPO Process, and Ringing That Bell, With CFO Amanda Whalen of Klaviyo.CFO Jenny Decker Unveils Top Frameworks Used at Front. —TIMESTAMPS:(00:00) Preview and Intro(02:34) Sponsor – Rippling Spend | Pulley | Navan(06:18) The Business of Star Wars(08:33) The Concept of “Spoilage” in Business(10:27) How To Identify Spoiled Capital(15:10) Spoilage Caused by Strategy Drift(16:25) Sponsor – NetSuite | Planful | Tabs(20:06) What Are “Levers and Leakages”(21:40) Identifying Levers(25:52) Identifying Leakages(26:37) The Center-of-Table Framework for Budgeting(31:03) The CFO As “Chief Alignment Officer”(33:06) How To Address Misalignment(34:57) What Alignment Looks Like in a Founder-Led Business(35:54) What Helicopter Skills Are and Why You Need Them(38:07) Data Safaris and Curiosity as a Secret Weapon(42:54) Aligning Data and Defining Metrics(45:08) Using Tropic for Capital Allocation Decisions(48:13) Spend Management: Cutting Costs Versus Driving Growth(51:08) Why Every CFO Needs a Spend Management Tool(52:59) Long-Ass Lightning Round: Alignment With Investors(55:13) Auto-Renewals: Good or Bad(56:25) Advice to Younger Self(57:08) Finance Software Stack(57:57) Craziest Expense Story—SPONSORS:Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.#capitalallocation #spendmanagement #capitalspoilage #centerofthetableframework #spendmanagementtool Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Carta's Head of Insights on Dilution, Equity, and the State of the Market Right Now

    Play Episode Listen Later Jun 2, 2025 67:14


    Is it true that founders should still own 50% of a company after a Series A fundraising round? Is 10% ownership at IPO a win or a loss? This episode delves into the topic of dilution, breaking down how much of your company you should sell at each stage, how to approach employee and advisor equity, and what employees should know about equity before taking a job. To answer these questions is Peter Walker, Head of Insights at Carta, and someone with a strong read on where the private tech market is headed. He and CJ also discuss when the best time to join a startup is and which cities outside of New York and San Francisco are desirable for people in this space. Peter shares insight into the state of the markets in 2025: What is happening with bridge rounds and down rounds, the odds of making it from seed to Series A, and the most telling statistic: AI funding.—LINKS:Peter Walker on LinkedIn: https://www.linkedin.com/in/peterjameswalker/Carta: https://carta.com/Carta's Founder Ownership Report 2025: https://carta.com/data/founder-ownership/Carta's published data reports: carta.com/dataCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.com—TIMESTAMPS:(00:00) Preview and Intro(02:33) Sponsor – Pulley | Tropic | NetSuite(07:17) Head of Insights at Carta(09:32) The Users of Carta(12:20) Multiplayer Finance and Serving Both Sides(16:24) Sponsor – Planful | Tabs | Rippling Spend(20:15) Dilution: How Much Ownership You Should Give Up at Each Stage(23:02) What SAFEs Are(24:31) The Median Amount of Ownership for a Founding Team After the Series A(26:21) Should You Still Own 50% of the Company After Series A(27:18) Is 10% Ownership for a Founder at IPO Normal?(30:41) The Other Form of Dilution: Employee Equity Grants(34:25) What Employees Should Know About Equity Before Taking a Job(37:51) Why Equity Is Not Money(38:54) ISOs Versus RSUs(40:43) The Best and Worst Risk-Adjusted Time To Join a Startup(44:48) Remuneration by Location in Private Tech(47:39) Equity Comp by Location(48:43) Advisor Equity by Stage(51:28) Bridge Rounds Versus Down Rounds in the Last 6–12 Months(55:36) Survival Rates From Seed to Series A to Series B(57:36) The Best Time of Year To Fundraise(59:05) The Typical Age of a Startup When It's Acquired or It Exits(01:03:19) The State of the Market in 2025: AI Funding(01:06:18) Wrap—SPONSORS:Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. Take control of your spend with intelligent spend management at tropicapp.io/mostlymetrics.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.#dilution #equity #stateofthemarket #privatetech #carta Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Mostly Mailbag - May Audience Questions

    Play Episode Listen Later May 31, 2025 19:13


    Welcome to our inaugural mailbag. I grew up worshipping the mailbags of Bill Simmons (Grantland) and Drew Magary (Deadspin). We needed one of our own.If you have a question for next month, drop it in the comments. And please give us five stars!!!This month's questions:* Career Screw-up Story – “You ask CFOs for mistakes. What's yours?” (Matthew from CO)* OnlyFans Valuation – “Is OnlyFans worth $8B?” (Lewis from MN)* Excel Model Versions – “What's the highest version number you've had in a model?” (Rebecca from MA)* Creative CAC Strategies – “What are some non-digital, low-cost customer acquisition strategies that actually work?” (Justin from FL)* Zombie Startups – “How many companies are 'default dead' but don't know it yet?” (Jackie from NY)* Cursed Model Tabs – “What's the worst tab name you've ever seen in a financial model?” (Tyler from MA)* Misunderstood Metrics – “What's one metric everyone pretends to understand but misuses?” (Rob from SF)* Finance-core Moments – “What's your most finance-core moment?” (Collin from SF)* Profit vs. Valuation in Startups – “Why don't more startups aim to be profitable businesses, not just high-valuation assets?” (Gregg from FL)Run the Numbers is brought to you by Zenskar.Zenskar is an AI-powered order-to-cash platform that automates billing, revenue recognition, and SaaS reporting — no spreadsheets, no engineering required. Built for modern B2B companies, Zenskar supports any pricing model: subscriptions, usage-based, or complex custom contracts.Step into the future of finance today. Visit zenskar.com/rtn and book a demo! Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    An Operationally-Focused CFO's Guide to Scaling From SMB to Enterprise: Lessons From ServiceNow

    Play Episode Listen Later May 26, 2025 76:12


    Serving SMB mid-market customers is one thing, but when you go upstream to enterprise sales, everything changes: go-to-market strategy, the sales process, how you structure deals, even how you define customer value. Today's guest, Andrew Casey, has helped scale four SaaS companies: ServiceNow, WalkMe, Lacework, and his current company, Amplitude. At ServiceNow, he worked closely with Snowflake's Mike Scarpelli and Coatue's David Schneider, and he was instrumental in establishing the company's deal desk to support its sales motion. As an operationally focused CFO, he shares a wealth of knowledge on the importance of staying close to the customer, structuring deals that work for both sides, establishing transparency in usage-based pricing, aligning incentives and strategy in sales, the pros and cons of multi-year deals, the problem with auto-renewals and what to do instead, and how to adapt your go-to-market strategy when moving from SMB mid-market to enterprise.—LINKS:Andrew Casey on LinkedIn: https://www.linkedin.com/in/andrew-casey-6b14875/Amplitude: https://amplitude.comServiceNow: https://www.servicenow.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:Gaining Strategic Advantage in Vertical SaaS With Guidewire's CFO, Jeff Cooper"Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & GrowthThe Largest Software IPO Ever: How Snowflake Still Left Money on the Table —TIMESTAMPS:(00:00) Preview and Intro(02:40) Sponsor – Tropic | NetSuite | Planful | Tabs(08:45) Becoming an Operationally Focused CFO(11:50) Staying Close to the Customer as a CFO(16:37) Sponsor – Rippling Spend | Pulley | MUFG(20:34) Running Towards a Challenging Market at ServiceNow(24:15) How He Established the Deal Desk at ServiceNow(26:13) Structuring a Deal That Works for Both Sides(29:08) Transparency in Usage-Based Pricing(32:39) A Client's “Budget Problem”: Cash or Expense Issue(36:42) Lessons From Building Out the Deal Desk at ServiceNow(40:53) Pros and Cons of Multi-Year Deals(43:57) Auto-Renewals: Do This Instead(46:10) Adapting the Go-to-Market Strategy for Enterprise Sales(55:33) Selling to CIOs Whose Jobs Are at Stake(58:18) What Defines “Enterprise”(59:43) The Most Important Thing To Get Right in Enterprise Sales(1:01:01) Lessons From Andrew's Background in Corporate Finance(1:03:12) The Story of How Andrew Got His Job at ServiceNow(1:07:57) Long-Ass Lightning Round: A Big Mistake(1:10:31) Advice to Younger Self(1:11:17) Finance Software Stack(1:14:47) Craziest Expense Story—SPONSORS:Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. Take control of your spend with intelligent spend management at tropicapp.io/mostlymetrics.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.MUFG is a global banking powerhouse that provides comprehensive banking services for VC-backed, PE-backed, and public companies with revenues starting at $40M. Accelerate your growth trajectory. Contact group head Bob Blee at bblee@us.mufg.jp to find out more.#SMBtoEnterprise, #gotomarketstrategy #scalingSaaS #dealdesk #ServiceNow Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Chime IPO: S1 Breakdown

    Play Episode Listen Later May 24, 2025 22:21


    Chime, the consumer fintech powerhouse, just filed to go public on the NYSE. On this podcast we'll cover everything you need to know before they hit Wall Street

    “Run Toward a Tough Market” — Developing the Hard and Soft Skills To Be a Great Finance Leader

    Play Episode Listen Later May 22, 2025 75:29


    To be a great finance leader, one needs to have both hard and soft skills. Today's guest believes in running towards the hard market, asking dumb questions, and showing up as your whole self at work. Craig Conti is the EVP and CFO of Verra Mobility, the almost $900 million in revenue, publicly-traded company that is responsible for the silent infrastructure behind seamless tolling, traffic enforcement, and smart mobility. Apart from providing a visual breakdown of his approach to mitigating risk, he shares a wealth of wisdom from his years in finance. Hear about why Craig prioritizes investing in existing customers when it comes to capital allocation and how he explains Verra Mobility's complex business model to non-finance people in the organization. This episode covers impostor syndrome, the difference between cost avoidance and cost savings, and why it may be more beneficial for you to work at a paper mill than at Apple, Meta, or Google.—LINKS:Craig Conti on LinkedIn: https://www.linkedin.com/in/craigcconti/Verra Mobility: https://www.verramobility.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:Uncovering Blind Spots and Other Lessons from High-Growth Companies with Five-Time CFO David Lapter. —TIMESTAMPS:(00:00) Preview and Intro(02:35) Sponsor – NetSuite | Planful | Tabs(06:20) An Intro to Verra Mobility(11:36) Continually Investing in Existing Customers(14:47) Explaining Your Business Model When You Have Multiple Business Lines(17:02) Sponsor – Rippling Spend | Pulley | Tropic(21:10) A Tip for Orienting Outsiders to Your Business(22:56) Decoding Finance for Non-Finance People in Your Org(29:33) Cost Avoidance Versus Cost Savings(31:00) How Having Resources To Reinvest Affects Capital Allocation Decisions(34:12) A Skillset for Stepping Into New Roles: Stupid Questions(38:55) Imposter Syndrome(40:52) A Visual Framework for Mitigating Risk(44:52) Known Risks Versus Unknown Risks(46:07) Why Incentives Need To Align With Risk and Reward(50:40) The Feedback Loop: Crisis Management to Future Risk Management(52:16) Hard Skills Versus Soft Skills in Finance(56:51) The Benefits of Bringing Your Whole Self To Work(59:12) “Always Run to the Tough Market”(1:03:34) “Life Comes Down to a Series of a Couple of Interactions”(1:08:04) Long-Ass Lightning Round: Bad Hiring Decisions(1:10:05) Advice to Younger Self: Move at Your Own Pace(1:11:46) Finance Software Stack(1:13:18) Craziest Expense Story—SPONSORS:NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. Take control of your spend with intelligent spend management at tropicapp.io/mostlymetrics.#financeleader #softskills #mitigatingrisk #capitalallocation #chieffinancialofficer Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Former PayPal CFO on Risk and Return in Venture Capital, Private Equity, and Public Companies

    Play Episode Listen Later May 19, 2025 71:18


    As a CFO, how should the way you navigate risk and return change from venture-backed companies to publicly-traded companies to private equity companies? To answer this question, CJ speaks with Mohit Daswani, a seasoned CFO with experience across multiple stages, including roles as CFO of Payments, Platform, and Risk at PayPal, and Head of Finance & Strategy at Square. Mohit shares the lessons learned from his time at Square, including when Jack Dorsey seeded a second billion-dollar business from within the company, and his experience at PayPal when they spun out from eBay under activist pressure. The conversation also covers the Rule of 40 in the different financial models, the dangers of using valuation as a scorecard, how founders should reset their mindset on what defines success, and the likelihood of a super app for the USA.—LINKS:Mohit Daswani on LinkedIn: https://www.linkedin.com/in/mohitdaswani1/SimplePractice: https://www.simplepractice.com/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.comRELATED EPISODES:From CF-No to CF-Go: Serial CFO Michael Bayer's Guide to Hypergrowth: Inside Grab: How a Super App Transformed Southeast Asia — with CFO Peter Oey: —Timestamps:(00:00) Preview and Intro(02:42) Sponsor – Planful | Tabs | Rippling Spend(06:36) Mohit's Office and a Tip From Churchill(09:07) Risk and Return in Different Investment Models(13:05) Financial Discipline Versus Room for Growth in Venture-Backed Companies(16:30) Sponsor – Pulley | Tropic | NetSuite(20:25) Balancing Short-Term Performance and Long-Term Bets in the PE Space(24:00) The Rule of 40 in Different Financial Models(30:19) What People Get Wrong About the Private Equity Model(34:40) The Benefits of Using Leverage(37:41) The Dangers of Using Valuation as a Scorecard(41:41) How Founders Should Reset Their Mindset on What Constitutes Success(44:00) Being at Square When Jack Dorsey Seeded a Second Billion-Dollar Business(49:43) Being at PayPal When They Spun Out From eBay(53:59) PayPal's Acquisition of Braintree(55:48) The Probability of a Super App for the USA(58:38) Learnings From Launching PayPal's Payments Dongle in Japan(1:04:12) Long-Ass Lightning Round: A Flight Mistake(1:06:20) Advice to Younger Self(1:07:31) Finance Software Stack(1:09:28) Craziest Expense Story—SPONSORS:Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics.Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. Take control of your spend with intelligent spend management at tropicapp.io/mostlymetrics.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.#VentureCapital #PrivateEquity #RiskManagement #RuleOf40 #PayPal Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

    Why Romanticizing PLG is Dangerous

    Play Episode Listen Later May 17, 2025 15:00


    This is going to make all the PLG fan boys & girls angry...Today we talk about why Romanticizing PLG is dangerous.With AI companies hitting $50M ARR overnight (amazing product, credit cards, and a golden retriever named Kevin), a dangerous myth is spreading:

    Portfolio Operations: This Is What You Actually Have To Do To Make Sure a Company Is Successful

    Play Episode Listen Later May 15, 2025 68:14


    To explain why portfolio operations are increasingly the secret weapon in private equity, CJ interviews Paul Stansik. Paul is the writer of the Hello Operator Substack and Operating Partner at ParkerGale. He shares hands-on insights into how his team helps portfolio companies scale by transforming sales data into decisions, navigating post-acquisition go-to-market challenges, and driving the shift from being merely data-aware to fully data-driven. He also discusses sales teams, from hiring the right sales leader for each stage of growth to whether or not having a great playbook is important. With insights on the dangers of unspoken problems (“you can't fix a secret”), how "templates build trust”, and how repeatable processes can unlock real commercial traction, this episode is packed with practical advice for CFOs, finance leaders, and operating partners.—LINKS:Paul Stansik: https://www.linkedin.com/in/paulstansikParkerGale: https://www.parkergale.comHello Operator: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: http://mostlymetrics.com—TIMESTAMPS:(00:00) Preview and Intro(02:52) Sponsor – Tabs | Rippling Spend | Pulley | Tropic(09:18) What ParkerGale Capital Does(11:35) Revenue Operations: Being the Keeper of the Standard(17:05) Sponsor – NetSuite | MUFG | Planful(20:34) Why Go-to-Market Teams Struggle To Provide More Data(24:29) Data-Aware Versus Data-Driven(26:54) Streamlining and Automating the Right Data(29:56) Why Everything Being Okay Is a Signal That Something Is Wrong(34:03) Defining Metrics and Why You Track Them(40:18) The Qualities of Great Sales Leaders(43:00) Why CEOs Often Pick the Wrong Sales Leader(47:58) The Importance of Hiring Someone With a Good Playbook(54:40) You Can't Fix a Secret(56:13) The Right Cadence for Reviewing Performance(58:34) What Good Quota Attainment Looks Like(01:01:02) The Lack of Training for Sales Teams(01:03:54) The Urge To Promote the Best Sales Rep to People Manager(01:07:10) Wrap#PortfolioOperations #PrivateEquity #GoToMarketStrategy #DataDrivenDecisions #SalesLeadership—SPONSORS:Tabs is a platform that brings all of your revenue-facing data and workflows - billing, AR, payments, rev rec, and reporting - onto a single system so you can automate and be more flexible. Find out more at: tabs.inc/metrics.Rippling Spend is a spend management software that gives you complete visibility and automated policy controls across every type of spend, saving you time and money. Get a demo to see how much time your org would save at rippling.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.Tropic is an intelligent spend management solution that consolidates your spend data and processes into one unified offering, enabling insights and decisive action. Take control of your spend with intelligent spend management at tropicapp.io/mostlymetrics.NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO's Guide to AI and Machine Learning.MUFG is a global banking powerhouse that provides comprehensive banking services for VC-backed, PE-backed, and public companies with revenues starting at $40M. Accelerate your growth trajectory. Contact group head Bob Blee at bblee@us.mufg.jp to find out more.Planful's financial planning software can transform your FP&A function. Built for speed, accuracy, and confidence, you'll be planning your way to success and have time left over to actually put it to work. Find out more at www.planful.com/metrics. Get full access to Mostly metrics at www.mostlymetrics.com/subscribe

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