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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
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
For today's essential Heretics 101 feature, we talk to David Heinemeier Hansson (aka DHH), creator of Ruby on Rails and co-owner & CTO of 37signals. He critiques DEI implementation and workplace wokeness, advocates political neutrality at work, and outlines his organizational philosophy emphasizing minimal management, creative constraints, and HR as leadership firewall.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH DHH, NOLAN + KELLI ON LINKEDINDHH: https://www.linkedin.com/in/david-heinemeier-hansson-374b18221/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Ruby on Rails: https://rubyonrails.org/37signals: https://37signals.com/—TIMESTAMPS:(00:00) Intro(02:34) "I Want My Code to Sing": Why Programming Is Poetry(04:35) How We Built a Company That Runs Itself(07:34) Sponsors: Planful | Metaview(08:34) The 40-Hour Work Week That Silicon Valley Hates(11:05) The Remote Work Wars: Why Both Sides Are Wrong(15:14) "No Politics at Work": The Two Weeks That Changed Everything(17:00) How Wokeness Held Corporate America Hostage(22:16) The Hardest Two Weeks of My Professional Life(25:28) The DEI Deception: Why Equity Isn't Equality(27:40) Why HR People Don't Suck (And Founders Need Them)(31:00) Final Thoughts: People Go Crazy When Work Is Everything(33:35) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.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
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
For today's essential Heretics 101 feature, we talked to Steve Cadigan, LinkedIn's first hired CHRO. Steve dissects LinkedIn's hypergrowth challenges, contrarian HR principles, and the fundamental shift from acquiring to developing talent internally.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH NOLAN + KELLI ON LINKEDINSteve: https://www.linkedin.com/in/cadiganNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Metaview 10x Podcast: https://www.metaview.ai/resources/10x-recruiting—TIMESTAMPS:(00:00) Intro(01:50) LinkedIn's Identity Crisis: When Your Product Is Your Problem(02:40) The Million-Dollar Question: "Why Would Anyone Want to Work Here?"(04:35) HR's Only Two Products: Judgment and Credibility(05:00) The Performance Review Rebellion(05:16) Sponsors: Planful | Metaview(07:21) Jeff Weiner's Intensity Philosophy: "I Live Off Chaos"(08:10) The Vulnerability Breakthrough: How a CEO Learned to Inspire(10:15) The Ownership Revolution: Why Leadership Teams Must Own HR(11:15) Remote Work Reality Check: "We Don't Know Yet"(12:00) Blitz Scaling Failures: Inheritors vs. Builders(13:43) The Perfectionist's Trap: "Do You Hear All Those Balls Dropping?"(14:20) Why He'll Never Return: The Six-Year-Old's Question That Changed Everything(15:27) Future of Work: From Buy Talent to Build Talent Economy This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
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
In this episode, Lex speaks with Ravi Adusumilli - President and GM of the Americas at Airwallex. Ravi and Lex discuss how Airwallex has evolved into a global financial platform by offering businesses an integrated suite of cross-border payments, treasury, and banking services. Founded in 2015, Airwallex now supports 150,000 customers, processes $130 billion in annualized volume (up 73% YoY), and projects a $1 billion revenue run rate by year-end.The company's success stems from its end-to-end infrastructure, homegrown payment rails, and multi-product strategy, with 80% of revenue now coming from customers using more than one product. Airwallex differentiates itself by focusing on global-first B2B use cases and building regional autonomy alongside centralized infrastructure. While not prioritizing stablecoins today, the company is exploring AI-driven financial operations and aims to reach $1 trillion in transaction volume by 2030. NOTABLE DISCUSSION POINTS:Airwallex's Infrastructure: Proprietary Global Payment NetworkAirwallex operates a proprietary global payment infrastructure that processes 95% of its $130 billion in annualized transaction volume. The company has developed its own technology and regulatory framework in partnership with over 60 banks worldwide. This approach reduces dependence on legacy systems such as SWIFT and supports greater control over transaction speed, cost, and compliance.Expansion Through Multi-Product OfferingAirwallex has expanded its services beyond cross-border payments to include card issuance, spend management, treasury functions, and merchant acquiring. According to company data, 80% of revenue is generated from customers using multiple products. Payments now account for 70% of net revenue and are growing at three times the rate year over year.Decentralized Go-To-Market StructureAirwallex employs a regional management model, with General Managers responsible for performance and operations in specific geographies. This structure is supported by centralized functions such as product development, compliance, and engineering. With 1,700 employees in 26 offices, the company uses this hybrid model to manage growth and adapt to local regulatory environments across multiple regions, including Latin America and Asia-Pacific. TOPICSAirwallex, Stripe, Brex, Rippling, Shopify, Pinterest, Visa, fintech, global payments, e-commerce, cross-border transactions, paytech, embedded payments, CFO stack, stablecoins, AI ABOUT THE FINTECH BLUEPRINT
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
Kelli and Nolan critically examine employee engagement surveys, arguing they're performative exercises for disconnected executives rather than meaningful tools for understanding and improving workplace sentiment.In this episode of HR Heretics, Kelli and Nolan sit down with Dave Margulius discussing Quizlet's remarkable 18-year journey from a bootstrapped startup founded with teenage co-founders to a globally successful education platform, sharing insights on building company culture, managing young talent, transitioning from founder to board member, and maintaining mission-driven values while achieving sustainable growth.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Related article:https://www.businessinsider.com/att-ceo-memo-workplace-loyalty-dead-employees-job-security-2025-8 Nolan's Linkedin post:https://www.linkedin.com/posts/nolan-church_when-can-we-eliminate-employee-engagement[…]m=member_desktop&rcm=ACoAAAWcjXgBb3Jw6dX16PD9lRJSsxfgqVAqZLw—TIMESTAMPS:(00:00) Intro(00:50) The 73% Response Rate That Changed Nothing(02:18) Devil's Advocate: Why Companies Think They Need Surveys(03:34) The Second Order Problem: Getting Data, Doing Nothing(04:30) "Get Out of the Ivory Tower"(05:28) Exit Interviews vs. Real Conversations(06:41) The Employee Perspective: Anonymous Survey Skepticism(07:37) The Performative Dance Exposed(08:43) Surveys as Substitutes for Real Leadership(09:13) Sponsors: Planful | Metaview(11:41) Better Alternative: Executives in the Dirt(13:25) The Venture Capital Leadership Model(14:49) The Small Minority That Actually Cares(15:40) The Semantics Problem: Stop Saying "Engagement"(17:00) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
In this episode of HR Heretics, Kelli and Nolan sit down with Dave Margulius discussing Quizlet's remarkable 18-year journey from a bootstrapped startup founded with teenage co-founders to a globally successful education platform, sharing insights on building company culture, managing young talent, transitioning from founder to board member, and maintaining mission-driven values while achieving sustainable growth.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH DAVE, NOLAN + KELLI ON LINKEDINDave: https://www.linkedin.com/in/davemarguliusNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—Quizlet: https://quizlet.com/—TIMESTAMPS:(00:00) Intro(02:00) The $5 Trillion Education Opportunity(04:06) Meeting Andrew - The 17-Year-Old Co-Founder(06:04) CEO Transitions and Early Career(09:11) Sponsors: Planful | Metaview(12:10) Building a Teenage Team(16:03) Managing Young Talent and Pure Adrenaline(19:17) The Shift to VC Funding(22:15) Company Culture and Values(26:19) Mission vs ROI Balance(29:05) 18-Year Journey and Staying Competitive(32:01) Employee Value Proposition and Liquidity(35:00) Competition and Market Position(36:06) Closing Thoughts(37:27) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
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
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
Today on HR Heretics, Nolan and Kelli critically examine the effectiveness and limitations of traditional exit interviews as organizational diagnostic tools, questioning their performative nature and strategic value.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(00:42) The Performative Checkbox Problem(01:38) The Fear Factor: Why Employees Won't Tell the Truth(02:39) The Real Exit Interview(04:06) The Drug Story: When Exit Interviews Actually Work(06:06) The Diagnostic Fallacy(07:18) The Neutral Feedback Myth(08:47) The Art of Information Filtering(10:35) Sponsors: Planful | Metaview(13:43) The Future People Leader Debate(16:49) Captain vs. Crew: Who Should Own These Problems?(18:11) The Completely Incomplete Nature(18:27) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
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
Siqi Chen, Matt Shumer, and Stephanie Palazzolo talk with TITV Host Akash Pasricha about OpenAI GPT-5 and AI Benchmarking. We also talk with Art Levy about Brex's growth & global payments, Kate Ryder about Maven's fertility tech, and we get into NVIDIA's family dynasty with Anissa Gardizy.Article discussed on this episode:https://www.theinformation.com/articles/nvidias-quiet-rising-stars-son-daughter-billionaire-founder-jensen-huanghttps://www.theinformation.com/articles/meta-acquires-ai-audio-startup-waveformshttps://www.theinformation.com/articles/brex-a-year-after-turmoil-has-profits-in-sightTITV airs on YouTube, X and LinkedIn at 10AM PT / 1PM ET. Or check us out wherever you get your podcasts.Sign up for the AI Agenda newsletter: https://www.theinformation.com/features/ai-agenda
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
For today's essential Heretics 101 feature, we talk to Casey Woo, founder of Operators Guild, and explore the evolution of elite business operators—generalist executives who transcend traditional titles to solve complex problems at high-growth companies, featuring insights on AI disruption, and community building.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors: Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH CASEY, NOLAN + KELLI ON LINKEDINCasey: https://www.linkedin.com/in/caseywooNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Operators Guild: https://operators-guild.com/—TIMESTAMPS:(00:00) Intro(01:15) WeWork Experience: Working with Adam Neumann(02:52) Key Lessons from WeWork(04:18) Current Market Climate & AI Impact(05:21) The AI Revolution in Customer Support(07:00) AI Management & the "Iron Man" Approach(07:31) Sponsors: Planful | Metaview(10:38) The Unstoppable Nature of AI Adoption(11:31) The Rise of the Operator: Casey's Personal Journey(14:02) Operators Guild: From 9 to 900 Members(14:20) The Four Operator Personas(15:17) Why Titles Have "Screwed Us"(15:35) The Navy SEALs Analogy(16:27) Building Successful Communities(17:55) Do You Ever Miss Operating?(18:43) The Future Path: From Operator to Founder(19:10) Breaking the Retirement Mindset(19:56) Advice for Operators: Have Confidence(21:28) The Power of Team Building(22:00) The Next Level: Capital & Founding(22:31) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
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
Host Erik Zhou, CAO at Brex, sits down with Richie Mashiko, Fractional CFO, to unpack the financial complexities of running high-growth e-commerce and CPG brands. From measuring the right things to navigating ad spend, pricing strategies, and fragile supply chains amidst tariffs, Richie offers a unique operator's perspective on what it takes to drive sustainable growth in today's market.
Immad Akhund is the CEO and co-founder of Mercury, a digital banking platform that's become the go-to financial infrastructure for startups. Before Mercury, Immad spent nearly two decades founding companies, learning the hard way what separates a good idea from a great business. In this episode, Immad shares the hard-earned lessons from launching Mercury as his third startup. He unpacks how he recognized this was the right idea to pursue, what strong product-market fit feels like, and why trying to "iterate" your way to success often leads founders astray. In this episode, we discuss: • Mercury's unusual culture playbook – and why it works • How to hire with intention • The trap of weak product-market fit • Shipping under intense pressure during the SVB crisis • And much more… References: • Airbnb: https://www.airbnb.com/ • Andreessen Horowitz: https://a16z.com/ • Apple: https://www.apple.com/ • Block: https://block.xyz/ • Brex: https://www.brex.com/ • Chime: https://www.chime.com/ • Gusto: https://gusto.com/ • Mercury: https://mercury.com/ • Paul Graham: https://x.com/paulg • Plaid: https://plaid.com/ • Stripe: https://stripe.com/ • SVB (Silicon Valley Bank): https://www.svb.com/ • True Link Financial: https://www.truelinkfinancial.com/ • Varo: https://www.varomoney.com/ • Y Combinator: https://www.ycombinator.com/ Where to find Immad: • LinkedIn: https://www.linkedin.com/in/iakhund/ Where to find Brett: • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ • Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: • Website: https://firstround.com/ • First Round Review: https://review.firstround.com/ • Twitter/X: https://twitter.com/firstround • YouTube: https://www.youtube.com/@FirstRoundCapital • This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (1:07) Hard-won lessons from serial entrepreneurship (2:02) You shouldn't copy-paste advice (6:57) Why personality trumps culture playbooks (8:48) How do you hire for cultural fit? (12:38) The values that shaped Mercury's DNA (14:08) The drivers underpinning Mercury's success (15:50) The significance of product-market fit (20:41) Don't fall into the weak product-market fit trap (25:49) How to evaluate startup ideas that scale (30:14) Mercury's unlikely origin story (33:51) Breaking into the fintech space (37:31) Mindset shift: From “This is hard” to long-term gains (39:43) Building Mercury's MVP (44:25) Overcoming early obstacles to reach launch (47:36) Navigating Mercury's rapid growth phase (51:18) Competition isn't the reason you're failing (55:58) Crisis management during the SVB collapse
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
Today on HR Heretics, Kelli and Nolan analyze the controversial Windsurf acquisition prompted by Windsurf employee #2's explosive social media post about receiving only 1% equity payout despite Google's $2 billion deal, highlighting Silicon Valley's eroding compensation norms.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(00:13) Prem's Bombshell Tweet(01:32) The DeepMind vs Cognition Choice(02:16) Clarifying the Exploding Offer(04:15) Kelly's Google Looker Experience(05:00) Why Contract Protections Don't Matter(06:07) Leadership Accountability(07:16) Silicon Valley's Broken Unwritten Rules(08:38) Sponsors: Planful | Metaview(11:37) Culture vs Money in Acquisitions(13:00) First Principles: The New Acquisition Reality(14:56) Gary Tan's Tone-Deaf Response(15:41) The Chaos of Modern Tech(17:00) The Power of Social Media Transparency(17:49) Wrap-Up This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
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
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
For today's essential Heretics 101 feature, Kelli and Nolan do a deep dive into executive recruiting mastery with VC Andy Price, covering why exec hires fail, back-channeling strategies, post-hire support, and building scalable leadership teams.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH ANDY, NOLAN + KELLI ON LINKEDINAndy: https://www.linkedin.com/in/andyprice1/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(01:02) Why Executive Hit Rates Are So Low(04:01) The Artisanal Process: "Soaking" with Companies(05:21) Back-Channeling Strategy(07:11) Recruiters Are Overpaid: The Real Work Happens After Hire(08:24) When Not to Hire - Too Early Stage Warning Signs(09:01) Sponsors: Planful & MetaView (12:46) How to Vet Search Firms(14:00) Experience vs. Trajectory(16:17) Scaling Up and Comers(17:30) Executive Career Management(20:25) Executive Tenure: Why the "One Year BS" Doesn't Work(22:36) The Authenticity Generation(23:52) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
Scaling New Heights Podcast: Cutting Edge Training For Small Business Advisors
On this episode of the Woodard Report podcast, Heather speaks with Brittany Brown about the painful lessons and courageous decisions that transformed her fast-growing firm, Ledger Gurus. Brittany shares how rapid expansion masked deep inefficiencies, ultimately resulting in nearly $1 million in lost profit, and how embracing accountability, data-driven metrics, and tough cultural shifts helped reverse course. She also discusses her evolving leadership philosophy, her passion for team building, and her new mission to reshape CAS education through university partnerships. About Brittany Brown Brittany Brown is the Founder and CEO of LedgerGurus, an industry leading ecommerce accounting CAS and inventory practice. Learn more about Brittany at: LedgerGurus.com LinkedIn Thank you to our show sponsor, Brex! Brex accounting partners close clients books faster, earn rewards for referrals and attract new customers all on Brex. Brex's integrated platform provides numerous accounting automation benefits, which enable your accountants to focus on premium advisory services, help clients close the books faster and elevate the overall client experience. To become a Brex accounting firm, visit brex.com/partners/accounting to apply. Learn more about the show and our sponsors at Woodard.com/podcast
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
Nolan and Kelli dive deep into the viral Astronomer scandal where the CEO and Chief People Officer were exposed having an affair during a Coldplay concert kiss cam moment. They examine the hypocrisy of executive leadership, the responsibilities that come with high-profile roles, and how this incident damages trust in HR leadership across the industry.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(00:13) Opening & Context(01:51) Initial Reactions(05:11) The Hypocrisy Factor(08:23) Leadership Responsibility(10:00) Work-Life Integration(15:58) Modern Visibility(18:00) Hypothetical Solutions(21:26) The Gwyneth Paltrow Response(25:00) Impact on Employees(26:00) Industry Implications(30:14) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
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
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
In this episode of HR Heretics, Kelli and Nolan sit down with Sarah Tilley, SVP of Global Talent at ServiceNow, to unpack how a $199B company is revolutionizing talent acquisition with AI. Sarah breaks down their two-speed transformation strategy—from optimizing basic recruiting processes to unlocking game-changing talent market intelligence that most companies can't even imagine yet.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH SARAH, NOLAN + KELLI ON LINKEDINSarah: https://www.linkedin.com/in/sarahtilley/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—ServiceNow: https://www.servicenow.com/—TIMESTAMPS:(00:00) Intro(01:09) What is ServiceNow?(04:22) The Two-Speed AI Strategy(13:08) Getting Started with AI Transformation(20:11) The Self-Service Recruiting Era(25:02) The Low Hire, Low Fire Market(28:00) Tracking AI Adoption(32:29) Quality of Hire Deep Dive(35:43) The Future: Skills-Based Hiring This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
For today's essential Heretics 101 feature, Kelli and Nolan talk to Ethena CPO Melanie Naranjo, challenging empathy-driven management, exposes toxic executive dynamics, and advocates for logic over emotion in workplace leadership.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH MELANIE, NOLAN + KELLI ON LINKEDINMelanie: https://www.linkedin.com/in/melanie-naranjoNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—Ethena: https://www.goethena.com/—TIMESTAMPS:(00:00) Intro(00:44) CEO-CHRO Partnership Transformation(02:23) The State of HR Leadership(04:08) The HR Crisis Revealed(05:20) The Root Cause Analysis(06:58) Sponsors: Planful | Metaview(10:00) The Anti-Empathy Argument(12:45) HR Community Dysfunction(14:21) The Gender Dynamics Truth(15:28) Executive Team Toxicity Exposed(17:13) The Politics Behind Dysfunction(19:39) Beyond Meritocracy(21:00) The Three Questions Framework(21:54) The Anti-PIP Philosophy(24:00) Direct Feedback That Works(24:42) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
Sherwood Callaway, tech lead at 11X, joins us to talk about building digital workers—specifically Alice (an AI sales rep) and Julian (a voice agent)—that are shaking up sales outreach by automating complex, messy tasks.He looks back on his YC days at OpKit, where he first got his hands dirty with voice AI, and compares the wild ride of building voice vs. text agents. We get into the use of Langgraph Cloud, integrating observability tools like Langsmith and Arize, and keeping hallucinations in check with regular Evals.Sherwood and Demetrios wrap up with a look ahead: will today's sprawling AI agent stacks eventually simplify? // BioSherwood Callaway is an emerging leader in the world of AI startups and AI product development. He currently serves as the first engineering manager at 11x, a series B AI startup backed by Benchmark and Andreessen Horowitz, where he oversees technical work on "Alice", an AI sales rep that outperforms top human SDRs.Alice is an advanced agentic AI working in production and at scale. Under Sherwood's leadership, the system grew from initial prototype to handling over 1 million prospect interactions per month across 300+ customers, leveraging partnerships with OpenAI, Anthropic, and LangChain while maintaining consistent performance and reliability. Alice is now generating eight figures in ARR.Sherwood joined 11x in 2024 through the acquisition of his YC-backed startup, Opkit, where he built and commercialized one of the first-ever AI phone calling solutions for a specific industry vertical (healthcare). Prior to Opkit, he was the second infrastructure engineer at Brex, where he designed, built, and scaled the production infrastructure that supported Brex's application and engineering org through hypergrowth. He currently lives in San Francisco, CA.// Related Links~~~~~~~~ ✌️Connect With Us ✌️ ~~~~~~~Catch all episodes, blogs, newsletters, and more: https://go.mlops.community/TYExploreMLOps Swag/Merch: [https://shop.mlops.community/]Connect with Demetrios on LinkedIn: /dpbrinkmConnect with Sherwood on LinkedIn: /sherwoodcallaway/ #aiengineering Timestamps:[00:00] AI Takes Over Health Calls[05:05] What Can Agents Really Do?[08:25] Who's in Charge—User or Agent?[11:20] Why Graphs Matter in Agents[15:03] How Complex Should Agents Be?[18:33] The Hidden Cost of Model Upgrades[21:57] Inside the LLM Agent Loop[25:08] Turning Agents into APIs[29:06] Scaling Agents Without Meltdowns[30:04] The Monorepo Tangle, Explained[34:01] Building Agents the Open Source Way[38:49] What Production-Ready Agents Look Like[41:23] AI That Fixes Code on Its Own[43:26] Tracking Agent Behavior with OpenTelemetry[46:43] Running Agents Locally with Phoenix[52:55] LangGraph Meets Arise for Agent Control[53:29] Hunting Hallucinations in Agent Traces[56:45] Off-Script Insights Worth Hearing
In this episode of The Girl Dad Show, host Young Han sits down with Jason Mok, VP and GTM leader at Brex and a devoted single dad. Jason currently serves as GM of Brex's Startups business and oversees Strategic Partnerships. Before Brex, he was an Operating Partner and GM at Andreessen Horowitz (a16z), where he led the firm's first $400M Seed Fund, and spent 16 years at Silicon Valley Bank championing early- and growth-stage founders. Jason's story spans decades of leadership in banking, venture capital, and fintech—but at the heart of it is a father navigating the complexities of work, legacy, and raising good humans. In this episode, Jason opens up about teaching his kids about money, setting boundaries between work and family, and how success as a parent isn't about control—it's about the relationship you build as they grow up. ✨ All episodes of The Girl Dad Show are proudly sponsored by Thesis, helping founders go further, together. Takeaways Jason Mok is a single dad and fintech exec at Brex Brex offers a financial stack for startups and enterprises Jason's path includes SVB, a16z, and years of startup advisory Parenting requires consistent self-reflection Teaching kids about money is non-negotiable Being present matters more than being perfect Self-care supports strong parenting and leadership Boundaries between work and family take real intention Legacy is built through quality relationships, not just career wins
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
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
For today's essential Heretics 101 feature, Kelli and Nolan explore compensation testing, remote culture scaling, leadership transparency, and AI adoption challenges through the analytical lens of Christine Centa, HashiCorp's Chief People Officer.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH PETER, NOLAN + KELLI ON LINKEDINChristine: https://www.linkedin.com/in/christine-centa-0a809b7/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—HashiCorp: https://www.hashicorp.com/en—TIMESTAMPS:(00:00) Introduction & Christine's Background(01:15) The Compensation Specialist to CPO Transition(02:26) Current Compensation Landscape & Market Data(04:00) The Midpoint Experiment(05:28) Equity Strategy & New Grant Structures(06:20) Going Public: Private to Public Transition(07:28) Sponsor: Planful | MetaView (10:27) Remote Work Philosophy & Scaling Challenges(11:53) The Connection Crisis(13:00) Leadership Dynamics: The Professor & Accountant(13:51) Transparency as Strategy(14:40) AI Strategy & Implementation Reality(16:00) AI in Recruiting: The Future Frontier(17:17) The AI Arms Race(18:00) The Work Behind the AI Dream(19:25) Preparing Teams for AI Future(20:09) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
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
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
Emergency pod: Returning guest Peter Walker (Carta's Head of Insights) analyze the controversial Windsurf deal, where Google's acqui-hire left non-founder employees without equity payout. They unpack the deal, reference Character AI's precedent, and explore how AI-era deals increasingly prioritize top researchers over broader employee bases, fundamentally changing startup risk calculations*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH PETER, NOLAN + KELLI ON LINKEDINPeter: https://www.linkedin.com/in/peterjameswalker/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—RELATED LINKS:Windsurf's CEO goes to Google; OpenAI's acquisition falls aparthttps://techcrunch.com/2025/07/14/cognition-maker-of-the-ai-coding-agent-devin-acquires-windsurf/Carta:https://carta.com/—TIMESTAMPS:(00:00) Intro(00:52) Breaking News: The Windsurf Situation(01:12) The OpenAI-Microsoft IP Rights Drama(03:01) Plot Twist: Cognition's Counter-Offer(04:49) The Employee Equity Problem(06:00) Defending Against "That's How Deals Work" Critics(08:00) The Scarlet Letter Effect(10:00) Regulatory Background: The Lina Khan Era(12:00) Revealed Behavior: What This Shows About Values(13:25) Sponsors: Planful | Metaview(17:00) Talent vs. Product Separation(19:53) The AI Era's R&D Researcher Obsession(22:00) Unequal Distribution of Outcomes(23:28) What Comes Next: Evaluating Startup Risk(24:00) The Founder Psychology Bet(25:00) Equity Structure Solutions(28:58) Becoming AI Native: Personal Brand Strategy(30:56) The New Reality: Expecting Less Care This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
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
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
For today's essential Heretics 101 feature, Kelli and Nolan examine the persistent challenge of HR professionals becoming genuine business leaders. Jeff Diana Investor/Entrepreneur, and former CPO of Calendly, join in to dissect tactical strategies for developing business acumen, moving beyond traditional people operations to drive meaningful organizational impact through financial literacy and strategic thinking.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH JEFF, NOLAN + KELLI ON LINKEDINJeff: https://www.linkedin.com/in/jeff-diana-a1906212/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(01:21) The Frustration: Why "HR at the Table" Still Doesn't Work(02:13) Jeff's Do's and Don'ts Framework for Business Leadership(04:26) KD's C-Suite Litmus Test(05:50) The Controversial Take: Understanding Founder Irrationality(06:49) Jeff's "Layers of the Cake" Business Metrics(08:35) Sponsors: Planful | MetaView (11:35) Synthesizing Learning for Your Team(12:14) Being the Best-Run Function Strategy(13:43) Career Mobility Benefits(14:10) The SuccessFactors Sales Kickoff Story(15:33) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
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
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
Kelli and Nolan critically examine Bolt CEO and Founder Ryan Breslow's announcement that they eliminated their HR department in favor of "People Ops", questioning whether this rebranding actually improves efficiency or just represents clickbait without meaningful organizational change. They explore the tension between removing perceived bureaucratic middlemen and maintaining necessary workplace oversight.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—Related Links:Ryan Breslow's LinkedIn Post:https://www.linkedin.com/posts/ryanbreslow_bolt-has-eliminated-its-hr-department-activity-7340377688517365761-0TcL/—TIMESTAMPS:(00:00) Intro(00:13) Bolt's HR "Elimination" Announcement(01:11) You Gotta Understand the Source First(02:43) Way to Say Something Without Really Saying Anything(03:24) Discussion: Good HR vs. Bad HR and Over-Planning(04:37) Why HR Gets Targeted: Speed and Headcount Issues(05:36) Who is People Ops Really?(06:21) Sponsors: Planful | Metaview(09:21) Who is People Ops Really? (continued)(10:07) Business Risk and Future of HR Functions(11:01) The Shift Has Already Been Happening(11:58) The Work Doesn't Go Away(12:22) Future of Work: AI Coaching and Managing Agents(13:21) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
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
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
A few weeks ago, we started bringing back essential Heretics 101 content. Today we're revealing insider secrets of equity negotiation that could save you millions. Colleen McCreary recommended this episode, and the stakes couldn't be higher.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(00:32) The Problem (HR Leaders Don't Understand Equity)(02:05) The Four Essential Questions Checklist(02:14) Question #1 (What's the Fully Diluted Share Count?)(03:53) Question #2 (What's the Strike Price/409A Valuation?)(05:03) Question #3 (What's the Last Preferred Price?)(07:51) The Golden Handcuffs Reality Check(09:38) Question #4 (What's Your Exercise Window?)(10:51) The Negotiation Secrets They Don't Tell You(12:08) Why Strike Price Appreciation Kills You(13:55) Sponsors: Planful | Metaview(16:44) Advanced Negotiation Tactics (21:51) Don't Take Equity at Face Value(22:47) Your Responsibility To Do the Research This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
Today's episode examines friend of the pod/recurring guest Colleen McCreary's "CEO-VP of HR divorce rate" concept, sparked by a VC's call about his CEO's failed six-month relationship with a seasoned HR leader. Colleen, Kelli, and Nolan explore why traditional interviews miss critical compatibility issues, the tendency to let conflicts fester rather than address them early, and essential strategies for either salvaging these crucial partnerships or ending them professionally.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH COLLEEN, NOLAN + KELLI ON LINKEDINColleen: https://www.linkedin.com/in/colleenmccrearychiefpplofficer/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Colleen's Medium article on Founder CEO & Head of HR Divorce Rates:https://medium.com/@colleenwheelermccreary/founder-ceo-head-of-hr-divorce-rates-c233c7fda7dcTIMESTAMPS:(00:00) Intro(00:28) The CEO-VP of HR Divorce Rate Post Origin Story(03:34) Learning from LJ Brock & Brian Armstrong's Relationship(04:13) What Interview Processes Miss: The Hard Stuff(06:13) Colleen's Trigger: Counter-Offers as Extortion(07:39) Why HR Leaders Need to Figure Things Out(08:51) Asking About Traumas in the Interview Process(09:32) Expecting Turbulence vs. Throwing in the Towel(10:14) Sponsors: Planful and Metaview(13:14) The Festering Problem: Avoiding vs. Addressing Issues(16:05) Molehills vs. Mountains: Managing Founder Relationships(18:06) Being a Filter, Not a Burden(18:43) The LinkedIn Marriage Analogy(20:35) Agency & Experience: First-Time Leaders vs. Veterans(21:39) Earning the Right & Paying Your Dues(23:52) Staying Misaligned: A Conscious Choice(25:19) Amicable Divorces & Doing It Right(26:10) Taking the High Road: Long-term Relationship Impact(27:10) 30-Year Relationships Still Matter(28:05) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
In this episode of HR Heretics, Nolan and Kelli get a behind-the-scenes look at Zapier's AI strategy with CPO Brandon Sammut. He demos some seriously impressive AI tools his team built—interview prep agents, automated workflows, performance tracking—and explains why they require AI skills from every new hire at their 730-person company. Make sure you also watch the video version on Substack and YouTube for the demo done by Brandon on Zapier Agent use cases.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH BRANDON, NOLAN + KELLI ON LINKEDINBrandon: https://www.linkedin.com/in/brandon-sammut-8147b76Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—RELATED LINKS:Zapier: https://zapier.com/—TIMESTAMPS:(00:00) Intro(01:30) The Four-Level AI Fluency Rubric(07:00) Pure Automation Examples (Non-AI)(13:10) Sponsors: Planful | Metaview(16:00) Bar Raiser Interview Prep Agent Setup(20:20) Live Agent Trigger Demonstration(21:10) Bar Raiser Interview Results & Discussion(26:15) Performance Review Evidence Collection Setup(34:10) Slack Emoji Workflow Demonstration(35:30) Market-Based Adoption Philosophy(36:00) One-on-One Meeting Coach Overview(43:30) One-on-One Coaching Feedback Example(44:00) Trust, Transparency & Implementation Strategy(48:20) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
In this week's 'Dear Heretics' segment, Kelli and Nolan examine the contested impact of AI on entry-level employment, featuring HR articles debating whether traditional junior roles are disappearing or evolving upward. The discussion explores practical AI implementation challenges, organizational inertia, and real-world examples of companies leveraging custom AI solutions for recruitment and decision-making processes.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—RELATED LINKS:Behind the Curtain: Top AI CEO foresees white-collar bloodbath: https://www.axios.com/2025/05/28/ai-jobs-white-collar-unemployment-anthropicJosh Bersin: No, Entry Level Jobs Are Not Going Away:https://joshbersin.com/2025/05/no-entry-level-jobs-are-not-going-away/—TIMESTAMPS:(00:00) Intro(00:34) The White-Collar Bloodbath vs. Optimistic Takes(01:53) Reality Check: Where's the Actual AI Implementation?(02:35) The Puck Has Moved: Redefining Entry-Level(03:31) Headcount Reality: Flat or Down Since 2022(05:30) Coinbase: The Only Company Actually Doing It(05:58) Sponsors: Planful & Metaview(09:00) Human Inertia: The Real Barrier to AI Adoption(10:47) The Custom GPT Success Story(13:34) Top-Down Mandates Break Through Inertia(14:00) Stop Building Programs, Start Experimenting(16:49) The Biggest Alpha Opportunity Ever(17:23) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
Episode 718: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk about stuff that hit the group chat this week. — Show Notes: (0:00) Apple Just Unlocked a $1B App Idea (04:13) McKinsey got $55M for This? (10:28) Frank Slootman's Ice-Cold Advice (16:20) “Treat people well, and you'll win.” (24:41) Man steals $122 million from Facebook and Google, (28:17) ChatGPT's $10B ARR retention curve (34:58) Elon v. Trump Meltdown (39:54) Ramp's Monopolist Pitch Deck (46:22) Rich Guy House Alert: Gary Tan Edition (48:55) Sam's First Ever Bookmark — Links: • Want Sam's top 7 books for entrepreneurs (& his reading strategy)? Get it here: https://clickhubspot.com/kmb • Apple AlarmKit announcement (WWDC) - https://developer.apple.com/wwdc23/ • Waymo Self-Driving Cars - https://waymo.com/ • Ramp (Eric Glyman's company) - https://ramp.com/• Brex - https://www.brex.com/ • Amp It Up - https://tinyurl.com/5ak4ckux • Les Schwab: Pride in Performance - https://tinyurl.com/5ch39nrv • TBPN - https://www.youtube.com/@thebrospodcastnetwork — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam's List - http://samslist.co/ My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano
The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch
Agenda: 00:00 – Meta's $14.8B Deal for Scale: The Analysis 05:40 – Will Scale Lose Their $800M ARR? Will All Customers Leave? 13:00 – Who is the Winner from All Scale Customers Leaving? 21:30 – Who Made the Most Money From Scale? 24:00 – LPs Just Got $14B Back. Are They Reinvesting? 26:45 – Chime IPO: The Breakdown 29:20 – Ramp Hits $16B Valuation: Are We Back in 2021? 31:10 – Ramp vs Brex vs Mercury: Who's the Real Winner? 34:00 – Gusto Going Public with $900M in ARR??? 36:40 – Dropbox vs Glean: Can the Old Guard Survive the AI Wave? 38:50 – Is Slack Dead as a Platform? Salesforce Shutdown Slack API? 41:15 – Will China Dominate AI? The Bets Are In 43:00 – S&P Prediction, iPhone Assembly in the US, and Rory's Rants Please read the offering circular and related risks at invest.modemobile.com. This is a paid advertisement for Mode Mobile's Regulation A+ Offering. Past performance is no guarantee of future results. Investing in private company securities is not suitable for all investors because it is highly speculative and involves a high degree of risk. It should only be considered a long-term investment. You must be prepared to withstand a total loss of your investment. Private company securities are also highly illiquid, and there is no guarantee that a market will develop for such securities. DealMaker Securities LLC, a registered broker-dealer, and member of FINRA | SIPC, located at 105 Maxess Road, Suite 124, Melville, NY 11747, is the Intermediary for this offering and is not an affiliate of or connected with the Issuer. Please check our background on FINRA's BrokerCheck.
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
Over the next few weeks, we're bringing you some Heretics 101 content - important refreshers on taboo topics that are core to navigating the CPO seat.For today's episode, we're revisiting an early conversation about how to fire C-suite executives that we had with CJ Gustafson from the Run the Numbers podcast. If you're in this business long enough, you're either going to have to fire an executive, or you're going to be the one getting fired. That's just reality. What started as a simple question turned into one of our most candid discussions about severance packages, golden parachutes, and layering. *Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH CJ, NOLAN + KELLI ON LINKEDINCJ: https://www.linkedin.com/in/cj-gustafson-13140948Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(00:52) The First Steps: When to Exit a C-Suite Executive(02:46) Decision vs. Discussion: Framing the Conversation(05:29) The Fourth Scenario: Growth Outpacing Talent(08:04) Compensation: The Spicy Details(10:36) Pre-Negotiated Severance: Red Flag or Smart Move?(14:50) Sponsors: Planful | Metaview(17:49) Golden Parachutes: The Biggest Payouts(20:47) Equity Acceleration and Exercise Windows(22:35) Rest and Vest: The Perverse Incentive Problem(24:12) Garden Leave Explained(24:51) VCs and CEO Firings: The Reputation Game(27:00) Advice for the Departing Executive(30:13) Controlling the Narrative(31:43) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
In this episode of HR Heretics, Nolan Church talk to Danielle Mathis, Vice President, Global Talent & HRBP of Clari, revealing how fraudsters orchestrated an elaborate recruitment scam, deceiving 12 job seekers with fake offers while harvesting their personal data. The shocking conversation exposes the dark reality of deepfake candidates infiltrating hiring processes and why traditional recruitment methods are dangerously obsolete in our AI-manipulated world.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
This episode of HR Heretics explores executive search from both sides: being recruited and managing recruitment. Neil Frye, former CPO at Google and Dropbox, and current Chief People Officer at Dotmatics, sits down with Nolan Church and discuss withdrawal strategies, internal versus external search criteria, conscious leadership frameworks, style compatibility, and treating job searches like mutual acquisitions rather than one-sided selections.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:
Send us a text[Original air date, April 9, 2024] Miguel Armaza interviews Jack Zhang, CEO & Co-Founder of Airwallex, a global payments and treasury giant that moves $7 billion in monthly transaction volume and serves 100,000+ clients, including Brex, Rippling, and SHEIN.Founded in Melbourne in 2015, Airwallex was last valued at $6.2 billion and has raised over a billion dollars from Sequoia, DST, Square Peg, Greenoaks, Mastercard, Tencent, Salesforce, and many more.In this episode, we discuss:How investing in a coffee shop led him to co-found a global payments networkWhy Airwallex prioritizes people with great leadership skills who are also technicalThe impact of AI in financial servicesNew risks of AI-powered financial fraudPartnering with almost 100 banks around the world… and a lot more!Want more podcast episodes? Join me and follow Fintech Leaders today on Apple, Spotify, or your favorite podcast app for weekly conversations with today's global leaders that will dominate the 21st century in fintech, business, and beyond.Do you prefer a written summary? Check out the Fintech Leaders newsletter and join 80,000+ readers and listeners worldwide!Miguel Armaza is Co-Founder and General Partner of Gilgamesh Ventures, a seed-stage investment fund focused on fintech in the Americas. He also hosts and writes the Fintech Leaders podcast and newsletter.Miguel on LinkedIn: https://bit.ly/3nKha4ZMiguel on Twitter: https://bit.ly/2Jb5oBcFintech Leaders Newsletter: bit.ly/3jWIp
In this episode of Yet Another Value Podcast, host Andrew Walker speaks with Darren McLean of Muddy Waters about investing in the mining sector. Darren shares how informational edges and a deep understanding of data can yield outsized returns in a space often overlooked by generalists. They discuss the inefficiencies in mining markets, the value of unconventional data analysis, and why mining offers compelling alpha for those willing to do the work. Darren also explores the evolution of mining capital, the brain drain in the industry, and the outsized rewards of discovering and developing world-class assets. Tune in to uncover the realities of resource investing and how expertise can change the game. _________________________________________[00:00:00] Andrew introduces podcast and Darren McLean[00:03:15] Why Darren sees alpha in mining[00:04:50] Examples of unconventional data collection[00:07:46] Darren discovers major inefficiency firsthand[00:10:23] Lack of diligence in asset qualification[00:15:51] The post-China supercycle mining collapse[00:20:57] Why mining offers inevitable investment returns[00:24:03] The Bre-X scandal and manipulation[00:27:42] Why supermajors avoid early-stage projects[00:31:26] When site visits are essential[00:38:47] Brain drain and generational void in mining[00:39:18] Can generalists invest in mining successfully?[00:43:17] Montage Gold: A re-rate case study[00:46:17] Value of strong reputations and strategic entry[00:51:13] Darren's track record and strategy success[00:53:36] Why mining gives clear investment feedbackLinks:Yet Another Value Blog: https://www.yetanothervalueblog.com See our legal disclaimer here: https://www.yetanothervalueblog.com/p/legal-and-disclaimer
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
In this episode of HR Heretics, Nolan Church and Kelli Dragovich talk to Cynthia "Baz" Shrauner, former Meta HR executive and current Head of People at Electric Capital. Baz discusses her unconventional career move of voluntarily demoting herself twice to focus on work she genuinely enjoyed rather than traditional leadership roles. She candidly explores the tension between ego and fulfillment, Meta's hiring excesses during COVID and subsequent layoffs, and the complexities of DEI initiatives in corporate environments, offering rare insider perspective on Silicon Valley's operational realities.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:
“HR Heretics†| How CPOs, CHROs, Founders, and Boards Build High Performing Companies
This segment examines the resurgence of "996" work culture (9 AM to 9 PM, six days weekly) among Silicon Valley's early-stage founders. Nolan analyzes the tension between demanding work schedules and talent attraction, drawing from Glen Evans' LinkedIn critique. He argues these intensive cultures suit certain life stages and career priorities, emphasizing that both high-intensity startups and work-life balance approaches can coexist as conscious trade-offs rather than moral imperatives.NOTE: Kelli is away this week spending time with family*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—Link to Glen's LinkedIn Post: https://www.linkedin.com/posts/glenevans_startups-leadership-workculture-activity-7328919826930814976-pEy7?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAWcjXgBb3Jw6dX16PD9lRJSsxfgqVAqZLwTIMESTAMPS:(00:13) Intro(00:31) 996 Culture Invades Silicon Valley(01:23) Greylock's Brutal Take(04:06) Does More Hours Equal More Productivity?(05:35) No Substitute For Time(07:18) My DoorDash Grind Days(08:30) Why I Can't Do It Anymore(10:06) Sponsors: Planful | Metaview(13:06) The 24-Year-Old Founders Story(14:15) "Don't Hire Me, I'm Too Old"(15:30) I Actually Miss Those Days(16:33) Life Is Trade-offs(16:55) The In-Person Only Founder(18:47) Humans Need Pain To Grow(19:12) Rule Breakers Build The Future(19:30) Appreciate Founder Honesty(19:53) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com
Today's show: Jason and Alex dicsuss Jony Ive's $6.5B deal with OpenAI and what it means for the future of AI hardware, Tesla's push into robotaxis vs. Waymo's 10M paid rides, and Microsoft's latest move partnering with xAI. We dive into the GENIUS Act and what it means for stablecoin regulation, explore practical, gritty tactics for launching and scaling a marketplace from scratch, and debate the ethics of AI-powered smart glasses and always-on recording. Plus, Jason reflects on the legacy of Scott Adams and the power of systems thinking.Timestamps:(0:00) Episode Teaser(2:00) A broadcaster-to-broadcaster moment for Scott Adams(5:18) OpenAI teams with Jony Ive, and why wearables are banned from the J-Ranch(10:16) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(16:11) From Partnership to Purchase: The M&A Story(20:09) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(25:42) Robotaxis EVERYWHERE, and thoughts on the continuing self-driving car rollout(30:12) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/banking-solutions(34:41) Should we trust stablecoins now? And who is actually monitoring this?(42:54) Polymarkets: Checking in with some of our favorite market(49:58) REDDIT QUESTION: How do I build a marketplace?(58:53) Customer feedback's role in product iteration(58:55) Every piece of SaaS advice EVERSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpLinks from episode:Polymarket: https://polymarket.com/Polymarket for AI Leaderes: https://polymarket.com/event/which-company-has-best-ai-model-on-june-30LMArena: https://www.lmarena.aiReal Coffee with Scott Adams: https://www.youtube.com/RealCoffeeWithScottAdams Follow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:(10:16) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(20:09) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(30:12) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/banking-solutionsGreat TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarlandCheck out Jason's suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
Today's show: Jason, Alex, and Lon break down OpenAI's latest power move: hiring Instacart CEO Fidji Simo to lead its consumer apps. They also dive into the ethical storm brewing around an AI-generated victim statement used in court — is this the future of legal testimony? Plus, they explore how late-stage funding rounds like a “Series G” don't automatically spell trouble anymore, and what The Checklist Manifesto can teach startup founders. Stick around for another Office Hours, where WhereToWheel gets a shot at the spotlight.*Timestamps:(0:00) We kick off the show!(2:28) Intro: It's all about having a system...(8:52) Wait, OpenAI STOLE Instacart's CEO?(10:00) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/banking-solutions(18:03) Why Adam Curry is the Podfather(20:08) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist(22:53) Would you want to be represented in court by an AI Avatar?(30:44) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(35:38) What the heck is "Minor M&A"?(48:10) When are we all getting humanoid robots?(53:30) Where2Wheel wants to help you off-roadSubscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcp*Links from episode:Check out Wheel2Wheel: https://dev.where2wheel.com/*Follow Where2Wheel:X: https://x.com/Where2WheelLinkedin: https://www.linkedin.com/company/where2wheel-llc/*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelm*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis*Thank you to our partners:(10:00) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/banking-solutions(20:08) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist(30:44) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist*Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland*Check out Jason's suite of newsletters: https://substack.com/@calacanis*Follow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.com*Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916