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

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

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

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

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?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

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

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

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

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

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