Podcasts about Brex

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.  

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

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:

In this episode of The SaaS CFO Podcast, host Ben Murray welcomes Austin Carroll, the dynamic founder and CEO of Warrant. Drawing from her deep roots in marketing and product management at household names like Capital One, Mercury, and Brex, Austin shares how real-world challenges navigating regulatory approvals inspired her to launch Warrant—a platform harnessing AI to automate and streamline marketing compliance for the financial services industry. Austin highlights the complexities and pitfalls of adhering to rapidly evolving federal, state, and local regulations in sectors like mortgage, insurance, and banking. She explains how Warrant checks marketing materials for compliance, helping companies of all sizes—from nimble startups to large enterprises—avoid costly missteps and accelerate their go-to-market strategies. Her journey provides invaluable insight into the needs of modern fintech marketers and compliance teams. Beyond the tech, Austin opens up about her path as a female founder, candidly discussing the fundraising process, her unique go-to-market approach, and the lessons learned from early customer traction. Whether you're passionate about fintech, compliance, or entrepreneurship, this conversation offers a compelling look at the future of AI-powered marketing compliance and the vision of a founder determined to solve one of the industry's most pressing challenges. Show Notes: 00:00 Streamlining Crisis Communication Compliance 06:09 Regulatory Challenges in Financial Compliance 07:12 Targeting Small to Mid-Market Clients 10:59 Strategic Market Engagement Approach 16:57 Entrepreneurship: Play to Your Strengths 17:51 Conversation-Driven Fundraising Strategy 21:40 Tracking Key Business Metrics 25:37 "Sign Up for Newsletter Now" Links: SaaS Fundraising Stories: https://www.thesaasnews.com/news/warrant-raises-720k-in-pre-seed-round Austin Carroll's LinkedIn: https://www.linkedin.com/in/austincarroll/ Warrant's LinkedIn: https://www.linkedin.com/company/warrant/ Warrant's Website: https://www.hellowarrant.com/ To learn more about Ben check out the links below: Subscribe to Ben's daily metrics newsletter: https://saasmetricsschool.beehiiv.com/subscribe Subscribe to Ben's SaaS newsletter: https://mailchi.mp/df1db6bf8bca/the-saas-cfo-sign-up-landing-page SaaS Metrics courses here: https://www.thesaasacademy.com/ Join Ben's SaaS community here: https://www.thesaasacademy.com/offers/ivNjwYDx/checkout Follow Ben on LinkedIn: https://www.linkedin.com/in/benrmurray

Welcome back to Not Fintech Investment Advice, where Simon Taylor and I talk about fintech companies that we're definitely not giving investment advice on!  We kick things off with Nekuda. Human-not-present is the new card-not-present. Nekuda's building SDKs (software development kits) for agentic checkout, so your AI assistant can securely store and inject payment credentials at just the right moment. This is Visa's “agent on file” era. We've spent a decade trying to keep bots out of commerce. Now we're figuring out how to let the right ones in (without blowing up the fraud model). What happens to trust, attribution, and liability when no human's at the checkout? Next is Vontive. Call them embedded mortgage lending for investment properties (basically, BNPL for real estate investors).They raised $135M in 2022, just added fresh equity from Citi, and secured a $150M revolving securitization shelf. They connect proptech platforms, banks, and marketplaces with private credit, so those platforms can embed short-term bridge loans or long-term rental mortgages directly into their UX. They don't hold the loans, but they do centralize underwriting across a very regionally variable asset class. And that can get risky fast. Then, there's Atticus, a stablecoin neobank in extreme stealth mode (with Palmer Luckey reportedly leading a new round at a $2B valuation). So naturally, we speculated: is Atticus a stablecoin bank with Fed access? A defense-industrial banking layer with regulatory immunity? If the GENIUS Act passes, this could be the first stablecoin issuer with full access to traditional rails. Finally, there's Affiniti. Embedded, vertical-specific SMB credit cards. Affiniti partners with trade associations (pharmacists, HVAC techs, auto dealers) to co-brand its SMB credit cards and distribute to pre-qualified member bases. They hit $5.5M ARR in year one and are on pace for $1B in transaction volume this year. Their edge is twofold: tailored underwriting based on industry norms, and an AI-powered CFO agent that flags anomalies, forecasts bills, and suggests vendor strategies. It's Ramp-as-a-service for the parts of the market that Ramp and Brex won't touch. The scaling question then becomes: choose depth (more products) or breadth (more industries)? We'll be watching. Plus, a manifestation: can someone please build a model that uses cashflow data to detect early signs of gambling addiction? It's doable, valuable, and might just save lives. This episode is brought to you by: Newline™ by Fifth Third is an innovative, API-first platform that enables fintechs to launch embedded payment, card and deposit solutions directly with Fifth Third Bank. Visit Newline53.com to see how Newline can elevate your business. Sign up for Alex's Fintech Takes newsletter for the latest insightful analysis on fintech trends, along with a heaping pile of pop culture references and copious footnotes. Every Monday and Thursday: https://workweek.com/brand/fintech-takes/ And for more exclusive insider content, don't forget to check out my YouTube page. Follow Simon: LinkedIn: https://www.linkedin.com/in/sytaylor/ Substack: https://sytaylor.substack.com   Follow Alex:  YouTube: https://www.youtube.com/channel/UCJgfH47QEwbQmkQlz1V9rQA/videos LinkedIn: https://www.linkedin.com/in/alexhjohnson Twitter: https://www.twitter.com/AlexH_Johnson Companies featured: https://nekuda.ai/ https://www.vontive.com/ Atticus (extreme stealth mode is right) https://affiniti.finance/

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

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:

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

In this episode of HR Heretics, Nolan Church and Kelli Dragovich interview Fidelma Butler, Chief People Officer at Couchbase, a NoSQL cloud database platform company. They talk about how to build effective L&D programs by defining clear leadership standards, focusing resources on senior leaders, and integrating learning into daily work instead of traditional training sessions.Fidelma emphasizes that L&D needs to be agile, continuously evolving, and solve actual business problems rather than existing as a separate "nice-to-have" function.*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 Fidelma, NOLAN + KELLI ON LINKEDINFidelma: https://www.linkedin.com/in/fidelmabutler/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINK/S:Couchbase: https://www.couchbase.com/—TIMESTAMPS:(00:00) Intro(00:39) The L&D Challenge at Scale(01:19) Tailoring L&D to Your Organization(03:00) Defining Good Leadership(06:00) Creating Leadership Language and Framework(08:00) Why L&D Struggles - Making Squishy Things Tangible(10:00) Meeting People Where They Are(12:00) Optimizing L&D for Top Performers(16:32) Sponsor: Planful | Metaview(19:30) Engagement Surveys Done Right(25:00) When Surveys Conflict with Leadership Vision(28:00) Leaders Teaching Leaders(31:30) Coaching Strategy and Deployment(35:30) The Future of L&D Roles(39:30) Getting Career Development Wrong(42:30) The Promotion Obsession Problem(46:00) 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

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

In this episode of HR Heretics, Nolan Church and Kelli Dragovich interview Sally Thornton, founder of Forshay. Sally shares insights on the fractional executive placement business she's built since 2011. Thornton emphasizes that successful fractional work requires consultative skills, boundary management, and rapid trust-building rather than simply scoped part-time arrangements. If you're thinking of going fractional, this is a must-listen discussion.*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 SALLY, NOLAN + KELLI ON LINKEDINSally: https://www.linkedin.com/in/sallythornton/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINK/S:Forshay: https://forshay.com/—TIMESTAMPS:(00:00) Intro(01:58) What Forge Does(02:33) Trust Barriers in Fractional Work(03:25) The Relational Approach(04:36) Buyer Mindset Challenges(06:10) Marketplaces vs. Agents(10:00) The Adverse Selection Problem(10:56) The Dirty Secret of Fractional(11:45) Different Interview Approach(13:03) Consulting Background Advantage(13:53) Sponsors: Planful | Metaview(16:57) The Ideal Buyer(17:26) Early vs. Late Stage Company Challenges(18:24) CFOs Make Better Clients(18:59) Transparent Pricing Model(21:41) Hourly Rate Guidelines(22:41) W2 vs. 1099 Considerations(23:27) The Honeymoon Phase(24:52) Managing Client Expectations(26:46) Beyond Filling Open Roles(29:08) The Assessment Process(34:29) Evolution from Interim to Fractional(37:05) Advice for New Fractional Execs(38:15) The Black Hole Complaint(40:11) Career Self-Management(42:11) Sustaining a 15-Year Business(43:06) 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

Kelli and Nolan explore the art of professional boundary-setting and etiquette. After Nolan shared a LinkedIn post about declining a meeting with a founder who didn't show up on time to their scheduled call, the hosts examine the delicate balance between protecting one's time and extending grace to others. Their conversation delves into how personal boundaries, stress levels, and professional status influence our responses to professional missteps*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 NOLAN'S POST:Community Regulation When People Break Social Etiquette—TIMESTAMPS:(00:00) Intro(00:16) When LinkedIn Goes Nuclear: The Time Management Debate(02:05) How Your Day Affects Your Tolerance(04:14) Different Cultures, Different Rules: Looker vs Google Time Ethics(07:48) Sponsors: Planful | Metaview(10:48) The Mother Test: When Accountability Matters Most(11:21) Calendar Hijacking: When Professional Boundaries Get Crossed(13:08) Societal Rot or Personal Standards? The Unwritten Rules Debate(15:34) Finding Your Boundary Line(16:14) What's Your Unwritten Rule?(16:22) 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, 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

Moving money internationally is mission-critical for many businesses in the world, particularly those outside the U.S. But, today, for businesses using traditional banks, moving money across borders is often expensive, slow and a terrible user experience. Wherever you have that combination you can be sure a fintech company is attacking the problem aggressively, which is certainly the case here.My next guest on the Fintech One-on-One podcast is Ravi Adusumilli, the President and GM of the Americas for Airwallex. They have built their own payments rails, as an alternative to SWIFT, to serve businesses who want to move money and accept payments internationally. How they have done that makes for a fascinating conversation.In this podcast you will learn:The target market for Airwallex in the Americas.How they help businesses expand internationally.Why they decided to build their own payments rails as an alternative to SWIFT.How the money moves exactly.The percentage of their payments that move in real time.What was behind their acquisition of MexPage in Mexico.Why they decided to build a business themselves in Brazil.How they are working with Brex.How Airwallex is able to serve smaller businesses.How they help tech companies offer embedded global payments as a profit center.How their multi-currency wallets work.Ravi's perspective on stablecoins and other alternative payments rails.His view on the future of embedded finance and global payments.Connect with Fintech One-on-One: Tweet me @PeterRenton Connect with me on LinkedIn Find previous Fintech One-on-One episodes

In this episode of HR Heretics, Nolan Church and Kelli Dragovich interview Jared Kleinert, founder of Offsite.com, who shares insights on planning effective team retreats that transform from "nice-to-have" into strategic "must-have" events for remote and hybrid companies. Kleinert emphasizes that successful offsites require intentional planning with clear objectives, arguing that thoughtfully designed retreats drive organizational alignment, build trust between teammates, and provide measurable business value beyond just logistics.*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 JARED, NOLAN + KELLI ON LINKEDINJared: https://www.linkedin.com/in/jaredkleinertNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINK/S:Offsite: https://marketplace.offsite.com/inquiry?utm=hrheretics—TIMESTAMPS:(00:00) Intro(00:47) Offsite's Business Model and Vision(02:17) Remote Work Trends and Offsite Planning(04:49) Elements of a Successful Offsite(09:38) Measuring Offsite ROI and Effectiveness(14:00) Adapting Offsites During Economic Downturns(16:26) Sponsors Planful | Metaview(19:52) Strategic Offsite Planning and Best Practices(26:46) Balancing Team Building and Business Performance(30:34) Executive Offsite Tactics and Trust Building(34:04) Pre-Offsite Preparation and Intention Setting(37:15) 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 this candid "HR Heretics" segment, Nolan and Kelli expose the hidden risks of equity compensation, including Nolan's $8 million DoorDash missed opportunity. They reveal essential questions about share counts, strike prices, and exercise windows that can make or break startup wealth. Their message: equity details are negotiable, but education is your responsibility—not the company's.*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:(00:13) Intro(00:52) Being Smart about Equity(01:46) Nolan's $8 Million Mistake(03:05) Understanding Share Count(04:44) Strike Price Explained(06:00) Preferred Price vs. Strike Price(07:43) Net Value Calculation(08:42) Golden Handcuffs Reality(10:31) Exercise Windows(12:00) Negotiation Opportunities(12:26) Tax Implications(14:07) Early Exercise Benefits(15:09) Sponsors: Planful | Metaview(18:09) Additional Negotiation Tactics(19:57) Executive Liquidity Options(21:32) Double Trigger Provisions(23:12) Vesting Schedule Negotiation(24:00) Key Takeaways(24:37) Personal Responsibility(26:08) Resources & Research(27:01) Final Thoughts(27:23) 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

In this installment of AI Corner, Siadhal Magos, the CEO of Metaview, and Nolan Church explore the emerging trend of "CEO AI mandates" from the likes of Tobias Lütke and Aaron Levie at Box.*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:Thatch makes it easy to give your team great healthcare. Save ~$1620 per employee yearly while giving them customizable plans. Visit https://thatch.AI/HR for a demo and receive a $100 gift card.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 SIADHAL, NOLAN + KELLI ON LINKEDINSiadhal: https://www.linkedin.com/in/siadhalNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINK/S: The 6 Steps to Master AI: TIMESTAMPS:(00:00) Intro(00:33) The CEO AI Mandate Trend(01:22) Siadhal's Take on AI Mandates(02:35) AI Orchestration as a Career Necessity(03:00) Headcount Management in the AI Era(04:04) AI Leverage vs. Team Size(06:03) Sponsors: Thatch | Planful(08:13) AI Upskilling and Education(09:21) Personal AI Tuition in Organizations(10:18) The Reflexive AI Problem-Solving Approach(11:27) Show and Tell: Learning from Power Users(12:00) Knowing What's Possible as Motivation(13:22) Carrot vs. Stick: Recognizing AI Adoption(14:38) Beyond AI as a Metric: Performance is the Goal(15:34) Wrap(15:58) Sponsor: Metaview 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 this week's 'Dear Heretics' segment, Kelli and Nolan unpacks the intricacies of 360 reviews from a management perspective, offering pragmatic approaches to synthesizing overwhelming feedback data. They contrast methodical theme-based analysis with modern AI-assisted solutions, emphasizing that meaningful feedback isn't an annual crucible but a continuous conversation peppered with five compliments per criticism.*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 (00:36) Dear Heretics - 360 Reviews Question (00:52) Good vs Bad 360 Reviews (06:34) Sponsors - Planful | Metaview (09:34) Using AI for 360 Reviews (11:38) On Using AI Tools (13:27) Sports Analogy Break (14:45) Getting the Ball Rolling (15:22) Continuous Feedback Approach (17:21) 5:1 Positive Ratio (17:59) Explaining the Why in Feedback (19:20) Making Feedback Enjoyable (19:26) 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 Lon break down the biggest stories in tech and startups this week: OpenAI's new models are powerful but glitchy, Meta's internal docs hint that Zuck knows the Facebook friends graph is toast, and fintech startup TapCheck might actually be doing some good. Plus, robot lifeguards and humanoid races — the wildest videos of the week and what they mean. Then, Alex sits down with Jason Reminick, founder of Thalamus, the platform that helps match medical residents to hospitals (with 85% market share!). They talk about becoming a Public Benefit Corp and how Thalamus is tackling the doctor shortage in the U.S.*Timestamps:(0:00) Jason kicks off the show(1:43) OpenAI's new models and issues with Wikipedia as AI knowledge bases(8:27) FTC antitrust case around Meta; breaking up big tech(11:13) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(13:04) Tapcheck's impact on employee retention and minimum wage variations(19:56) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(24:31) New company Revel's safety software(27:14) Humanoid robot marathon in Beijing(30:15) Brex. Get the business account trusted by 1 in 3 US startups at ⁠https://brex.com/banking-solutions(35:46) New color discovery “Olo”(40:30) Blue Sky is Falling: Robots, delivery, surveillance, and privacy concerns(55:20) Alex sits down with Jason Reminick of Thalamus(56:01) Thalamus and the medical residency application process(59:42) AI in residency applications and standardizing medical school grades(1:03:30) Thalamus' market share and collaboration with medical associations(1:10:08) Impact of budget cuts on rural hospitals and business model expansion*Subscribe 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 Thalamus: https://www.thalamusgme.com/Check out the Robot Lifeguard: https://oceanalpha.com/product-item/dolphin1/Check out TapCheck: https://www.tapcheck.com/*Follow: Jason ReminickLinkedIn: https://www.linkedin.com/in/jason-reminick-md-mba-ms-bb251645/Thalamus on X: https://x.com/ThalamusGME/status/1757812695787581485*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:(11:13) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST(19:56) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(30:15) Brex. Get the business account trusted by 1 in 3 US startups at ⁠https://brex.com/banking-solutions*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

Victor Lazarte is a General Partner @ Benchmark, one of the mot renowned venture firms in the world. At Benchmark, Victor has led deals into the likes of HeyGen and Mercor. As an angel, he was the first investor and board member of Brex, and as a Founder he scaled Wildlife Studios, bootstrapping into the largest gaming company in LatAm, with about 4 billion downloads.  In Today's Episode We Discuss: 04:10 Lessons Scaling Wildlife Studios to 4BN Downloads 04:49 Why Predicting the Future is Wrong When Starting a Company 07:11 Three Different Categories of Company in an AI World: Who Wins & Loses? 09:25 Why You Should Always Ask What a Founder Does in Their Free Time? 17:30 Two Traits That All the Best Founders Have? 23:17 Why If You Start a Company in SF You are 1,000x More Likely to be Successful? 35:30 Why Spreadsheet SaaS Investing is Dead 36:10 Why Replacing Humans is the Most Exciting Opportunity in AI 37:02 Why Knowledge Work Will Be Destroyed and What Happens Then? 37:30 Why China is a Stabilising Force for the US 38:59 China vs. US: The AI Race 42:33 Why All Students Today Should Study Computer Science 44:38 Why Portfolio Construction is BS 47:04 What Makes Peter Fenton One of the Best Ever 51:31 Why Duolingo Will Be One of the Most Valuable Companies in the World 01:00:17 Quick Fire Round: Insights and Predictions  

Flexport was a breakout success—reimagining global trade with tech at its core. But when the freight market cooled and efficiency overtook service, things started to unravel. Founder Ryan Petersen stepped aside, handing the CEO role to former Amazon exec Dave Clark. Months later, he was back at the helm.In this episode, Ryan explains what went wrong, how he's rebuilding Flexport—cutting $300M in costs, restoring customer focus—and why promoting from within beats chasing outside stars. He also weighs in on Trump's proposed tariffs and what they could mean for the future of global trade.Chapters: 00:00 Trailer00:31 Introduction02:07 Meeting smart people, seeing the world03:40 Eroded margins09:52 Charismatic and overconfident15:32 Not an overnight decision20:08 The founder has returned23:10 Redoing the hiring26:38 No substitute for passion31:00 Working for and with my brother37:28 Working with forwarders42:14 Being a founder can be lonely47:49 Life's work54:06 The right person for the job1:00:55 19 countries1:04:57 Blowing people up1:07:24 Work and being a good dad1:08:34 Not doing it for money and loving money1:17:52 Import and export tariffs1:22:57 De minimis1:25:54 Panama and the Suez Canal1:36:50 Going public1:42:24 Who Flexport is Hiring 1:42:42 What "grit" means to Ryan1:43:06 OutroMentioned in this episode: Founders Fund, Amazon, Toyota Motor Corporation, Slack, Brex, Pedro Franceschi, Henrique Dubugras, United States Customs and Border Protection, ImportGenius, Michael Kanko, Y Combinator, Paul Graham, Intel Corporation, Shopify, Geely Holding (Zhejiang Geely Holding Group Co., Ltd.), The Volvo Group, Intuit TurboTax, David Petersen, BuildZoom, TechCrunch, Google, Figma, Barack Obama, Donald Trump, Jimmy Carter, Panama Canal Authority, United States Navy, Coinbase, Uber, AirbnbLinks:Connect with RyanXLinkedInConnect with JoubinTwitterLinkedInEmail: grit@kleinerperkins.comLearn more about Kleiner Perkins

Today's show: Jason, Alex, and Lon talk about stories reshaping the startup world: 70mph drone deliveries are officially live in Dallas, with Zipline and Walmart promising groceries “as the crow flies” in under 5 minutes. Meanwhile, Trump slaps a 125% tariff on China and hints at a global economic shakeup — Jason warns founders to brace for layoffs and bankruptcies unless they've got a Plan B and C. Finally, a UK startup sells for $450M and VCs barely break even… but the founders walk with $20M. Jason explains how small exits create the most dangerous kind of founder: the one who never needs another check. Plus Office Hours with Orchestra CEO Sergie Poe.Timestamps:(0:00) Jason kicks off the show!(1:37) Tariffs, market volatility, and startup implications(5:33) Startup resilience: Layoffs and bankruptcies(10:35) Brex. Get the business account trusted by 1 in 3 US startups at ⁠https://www.brex.com/banking-solutions(12:10) Globalization and startup ecosystems(13:52) Recent startup deals and Zipline's expansion(19:56) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(21:16) Zipline drones and Marquese Brownlee's review(24:31) 70MPH Drones and the future of ddeliveries(30:05) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(31:51) Founder FridaysPitch Madness matchups(33:35) LifeStack and Burble pitches and discussion(43:26) Arcana and Tactun pitches and discussion(50:12) Summer West Whiskey and MomSub pitches and evaluation(56:36) Orchestra's office hours: Challenges and strategiesSubscribe 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 the show:Orchestra: https://orch.so/Follow 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:(10:35) Brex. Get the business account trusted by 1 in 3 US startups at ⁠https://www.brex.com/banking-solutions(19:56) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist(30:05) Northwest Registered Agent. Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!Great 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