Podcasts about Brex

AGENDA: 03:36 Brex Acquisition by Capital One for $5.15BN 10:54 Does Brex's Acquisition Help or Hurt Ramp? 16:28 TikTok Deal Completed: Who Won & Who Lost: Analysis 19:30 Anthropic Inference Costs Higher Than Expected 37:50 Open Evidence Raises at $12BN from Thrive and DST 53:56 Wealthront IPO Disaster: Is $1.5BN IPO Too Small? 01:07:27 Salesforce Wins $5BN Army Contract: The Last Laugh for SaaS  

Theory meets tarmac. Sushmitha "Sushi" Radhakrishnan runs finance and operations at Birddogs, the men's apparel brand born from a Shark Tank moment that's now selling through Dick's Sporting Goods. She breaks down what cash flow actually looks like when summer—not holidays—is your Super Bowl, tariffs hit mid-growth, and every trend cycle could make or break a season.Key takeaways:Seasonal brands need capital access during revenue troughs, not just peaksMulti-channel operations demand different buying cycles—wholesale plans months ahead while DTC converts in hoursSpeed separates winners in apparel—trends change faster than traditional finance approval loopsSmall teams need executive-level spend control with rapid scalability for growth momentsKey Quotes:Sushi Radhakrishnan [00:14:49]: "Because we are a seasonal business, having access to credit cards like a Brex where we have charge cards—in those situations when we're in our cash flow troughs, having that extra flexibility is really critical to us. There's a six month period where we have to have really good months because that's what funds the business in the lower months."Sushi Radhakrishnan [00:20:28]: "This is my first foray into apparel and selling it online and trends change so quickly. A winning product—it's definitely a very dynamic environment to operate in."Sushi Radhakrishnan [00:18:12]: "We move really fast. Getting that feedback loop shortened is really important when we're managing cash. That's been refreshing with Brex—the support we're getting from a credit card provider. I don't have that same level of one on one service with American Express."Sushi Radhakrishnan [00:23:22]: "People buy apparel based on emotion, not just because they see it come across their Instagram reel. It's really important that we continue to appeal to our buyers in a way that's more than just selling the value prop of our product."Associated Links:Learn more about BrexLearn more about MelioCheck out Future Commerce on YouTubeCheck out Future Commerce Plus for exclusive content and save on merch and printSubscribe to Insiders and The Senses to read more about what we are witnessing in the commerce worldListen to our other episodes of Future CommerceHave any questions or comments about the show? Let us know on futurecommerce.com, or reach out to us on Twitter, Facebook, Instagram, or LinkedIn. We love hearing from our listeners! Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode of Run the Numbers, CJ sits down with Dan Griggs, CFO of Intercom, to break down how finance leaders should think about pricing, forecasting, and resource allocation in the AI era. Dan explains why “it's not zero” is his guiding forecasting principle, how Intercom landed on 99 cents per AI resolution for Fin, and what it means to build an AI product that could eventually cannibalize a successful SaaS core. A candid look at managing uncertainty while still making bold bets.—SPONSORS:Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai—LINKS:Dan on LinkedIn: https://www.linkedin.com/in/dan-griggs-0970181/Intercom: https://www.intercom.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Inside Rocket Companies: M&A, Metrics, and Mortgage Moats | Brian Brownhttps://youtu.be/ttedn4AULt8—TIMESTAMPS:00:00:00 Cold Open00:01:03 Intro to Dan Griggs and Intercom's AI Pivot00:02:45 From Ice Cream to SaaS: Early Finance Lessons00:04:19 Learning the Business by Living the Operations00:06:26 Why Operational Reality Shapes Better Forecasts00:08:00 “It's Not Zero”: Forecasting the Unknowable00:10:09 Scenario Planning, Ambiguity, and Psychological Safety00:11:23 Sponsors — Brex | Metronome | RightRev00:14:43 Keeping a Mental Model of Key Business Metrics00:16:15 Using Mental Math to Sanity-Check Forecasts00:17:28 Core Ratios Every CFO Uses to Vet Decisions00:19:13 The Burn-the-Boats Moment for Intercom's AI Pivot00:20:53 Why AI Was an Existential, Not Incremental, Bet00:22:21 Which SaaS Categories AI Can Fully Replace Work00:23:04 Why Finance Hasn't Had Its AI Moment Yet00:23:39 Sponsors — Rillet | Tabs | Abacum00:27:05 Why Fin Needed Outcome-Based Pricing00:28:59 The Tradeoff Behind $0.99 Per Resolution00:30:46 Why Support Conversations Vary in Complexity00:32:01 What Drives the Unit Economics of AI Resolutions00:33:08 How Intercom Chooses Models as Costs Fall00:35:19 Replacing Generic LLMs With Domain-Specific Models00:36:08 Selling an AI Product That Could Cannibalize the Core00:38:50 Founder CEOs Versus Professional CEOs00:41:47 Hiring Mistakes and Acting on Instincts00:44:28 Intercom's Finance Software Stack00:45:49 The Craziest Expense Request#RunTheNumbersPodcast #Intercom #AICustomerSupport #OutcomeBasedPricing #CFOInsights This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

The old retail calendar is dead. Between TikTok virality, celebrity sightings, and ChatGPT-powered discovery, brands face a new reality: commerce runs on culture's clock. Nicole Thomas (Brex) and Anand Mehta (Melio) break down how this shift from predictable peaks to perpetual possibility demands radical financial agility.Key takeaways:Retail shifted from twice-yearly peaks to monthly cultural spikes brands can't predictCash conversion cycle reveals hidden supplier payment leverage beyond inventory optimizationCredit card float extends working capital without compounding traditional loan debtLiquidity separates trend leaders from trend chasers regardless of business sizeKey Quotes:Nicole Thomas [00:06:27]: "Seasonality is kind of taking shape in the way that it's less of like these ebbs and flows maybe twice a year to maybe once a month. If your product goes viral or if a celebrity endorses something, your consumers are now expecting to get those products when they want it."Anand Mehta [00:22:17]: "Costco managed to have a very low, if not negative cash conversion cycle because their store is the warehouse. They've already sold and converted their inventory to cash before they even have to pay it out."Nicole Thomas [00:37:06]: "Commerce is definitely making a big shift to flattening out, but not flattening out enough to where you can actually predict those peaks and valleys. We're definitely shifting from a calendar economy to more of a cultural economy."Anand Mehta [00:32:14]: "This use case of extending cash flow isn't just for businesses who are struggling. If you're a brand that is very liquid, having that cash buffer allows you to be a brand that's jumping in on a trend in the early stages of the trend, not chasing a trend."In-Show Mentions:Learn more about BrexLearn more about MelioCheck out Future Commerce on YouTubeCheck out Future Commerce+ for exclusive content and save on merch and printSubscribe to Insiders and The Senses to read more about what we are witnessing in the commerce worldListen to our other episodes of Future CommerceHave any questions or comments about the show? Let us know on futurecommerce.com, or reach out to us on Twitter, Facebook, Instagram, or LinkedIn. We love hearing from our listeners! Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Esta semana hablamos de la caída en el consumo en ciudades fronterizas de EUA, Pinterest en México, la compra de Brex por Capital One, el aumento en matrículas en escuelas de derecho en EUA, y la adquisición de Pulppo por Tuhabi, entre otros temas.Prueba Whitepaper 30 días gratisCompra tu gorra o ilustraciones de Whitepaper aquí

Cash flow isn't just spreadsheets—it's survival. In an era of tariffs, currency swings, and supply chain whiplash, small businesses face a paradox: grow fast while everything shifts beneath you. Corinne Boonstra (Brex) and Aharon Naveen (Melio) unpack how payment independence becomes the ultimate competitive advantage.Key takeaways:Tariff volatility forces brands to message consumers directly about pricing pressuresSmall businesses gain agility advantage by switching suppliers faster than competitorsPayment independence decouples cash flow from vendor relationship power dynamicsTechnology stacks need finance-novice friendliness, not just CFO sophisticationKey Quotes:Corinne Boonstra [00:08:11]: "Brands are having to reach out to their consumer base to communicate with them why prices are increasing or using that as kind of a pivotal point of, say, buy these goods now while they're this price."Aharon Naveen [00:12:06]: "Switching vendors is complex. It comes with an operational overhead of different net terms, different currency conversions, different shipping time, different payment acceptance."Aharon Naveen [00:19:45]: "Giving the control back to small business, putting them in a position that they can overcome the relationship dynamic or the power dynamic of a new vendor—that is what technology brings to play."Corinne Boonstra [00:23:10]: "These tools need to be able to be leveraged by your CMO, your head of digital, your founder—whoever is ultimately making these decisions might not have an accounting background."Associated Links:Learn more about BrexLearn more about MelioCheck out Future Commerce on YouTubeCheck out Future Commerce+ for exclusive content and save on merch and printSubscribe to Insiders and The Senses to read more about what we are witnessing in the commerce worldListen to our other episodes of Future CommerceHave any questions or comments about the show? Let us know on futurecommerce.com, or reach out to us on Twitter, Facebook, Instagram, or LinkedIn. We love hearing from our listeners! Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Shomik is the newest partner at Sierra Ventures! A longtime venture investor and an inception-focused fund backing technical founders at day zero. He supported companies like Cloudquery, Kiln AI, and Ask-Y, and played a role in many other early investments.Shomik was an investor at Top Tier Capital, where he focused on growth-stage companies including CircleCI, Anaplan, Remitly, Shape Security, and Snyk. His path into venture was anything but traditional, with early experience spanning tech M&A, venture debt, a failed startup, and fixed income sales and trading.Originally from New Jersey and a Pittsburgh alum, Shomik is an avid hiker, an aspiring guitarist—progress very much still in flight—and the proud dad of a one-and-a-half-year-old son who now takes up all of his spare time.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Shomik Ghosh: @shomikghosh21@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

How do you transform a collection of individual tools into a cohesive, AI-powered symphony? Vineeta Puranik (CPTO @ SmartBear) dissects the strategy behind evolving a product vision from point solutions to a unified multi-product ecosystem. We explore the critical architectural distinction between "AI bolt-on" and "AI native" strategies, frameworks for seamless M&A integration, and how to design for varying levels of customer AI readiness. Vineeta also discusses the shift to test “does it match intent”, using “jobs to be done” to drive solving entire workflows not just tool capabilities, and designing user experiences for both human personas and AI agents. ABOUT VINEETA PURANIKVineeta Puranik serves as Chief Product and Technology Officer (CPTO) at SmartBear, where she leads the company's global technology and product strategy to empower developers and enterprises worldwide. A seasoned technology executive with over two decades of experience, she combines strategic vision with hands-on leadership to drive innovation, growth, and operational excellence.At SmartBear, Vineeta oversees development, cloud engineers, AI, and architecture, and has been instrumental in scaling centers of excellence in India and Poland, launching the Developer Academy, and advancing the company's hub-based product strategy – Swagger suite for API capabilities, Test Hub, and Insight Hub. Recognized for her collaborative, people first leadership and commitment to inclusion, she was named a 2024 Women Worth Watching in STEM by Profiles in Diversity Journal. This episode is brought to you by Retool!What happens when your team can't keep up with internal tool requests? Teams start building their own, Shadow IT spreads across the org, and six months later you're untangling the mess…Retool gives teams a better way: governed, secure, and no cleanup required.Retool is the leading enterprise AppGen platform, powering how the world's most innovative companies build the tools that run their business. Over 10,000 organizations including Amazon, Stripe, Adobe, Brex, and Orangetheory Fitness use the platform to safely harness AI and their enterprise data to create governed, production-ready apps.Learn more at Retool.com/elc SHOW NOTES:SmartBear's evolution from individual tools to a connected ecosystem (3:34)The cultural shift toward vendor consolidation and avoiding context switching (5:39)Why "Jobs-to-be-Done" must drive the workflow, not just the tool capabilities (9:35)The shift in testing: Moving from "does it crash?" to "does it match intent?" in an AI world (14:26)The architectural difference between "AI Bolt-On" and "AI Native" products (20:44)The levels of autonomy: A framework for moving from manual control to autonomous testing (24:10)Designing for different customer personas: Addressing security, policy, and AI readiness (30:01)Rapid Fire Questions (32:50) LINKS AND RESOURCES Books MentionedOwn the Room: Discover Your Signature Voice to Master Your Leadership Presence by Amy Jen Su and Muriel Maignan Wilkins.The Leader You Want to Be: Five Essential Principles for Bringing Out Your Best Self--Every Day by Amy Jen Su.SmartBear Tools & ProductsSmartBear[**Reflect**](https://reflect.run/?utm_medium=referral&utm_source=smartbear.com&utm_campaign=prodnav&_gl=1*4gpwr4*_gcl_au*MTAzOTk0MjM2LjE3Njk0NjU4NTA.) – Mentioned as their "AI Native" product for autonomous testing.Zephyr Scale – Mentioned regarding the Atlassian ecosystem integration.[**QMetry**](https://www.qmetry.com/?_gl=1*1d5sv56*_gcl_au*MTAzOTk0MjM2LjE3Njk0NjU4NTA.) – Recently acquired test management product.[**Swagger**](https://swagger.io/product/?_gl=1*gtu348*_gcl_au*MTAzOTk0MjM2LjE3Njk0NjU4NTA.) – Mentioned as the suite for API design and compliance. This episode wouldn't have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan's also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Are you accidentally breaking CPA rules across state lines? Guest Lindsay Patterson, CPA CIA breaks down the new mobility landscape after alternative licensure paths—and the surprising data firms must track to avoid fines, failed peer reviews, and redoing audits. Plus: Congress's Fiscal State of the Nation bill, Deloitte's PR storm, QuickBooks' AI reconciliation, and what's driving a rebound in accounting majors. Walk away knowing where to get licensed, what triggers penalties, and how to protect your firm.SponsorsTaxBandits - http://accountingpodcast.promo/taxbanditsEarmark - http://accountingpodcast.promo/earmarkOnPay - http://accountingpodcast.promo/onpayUNC - http://accountingpodcast.promo/uncChapters(00:00) - Introduction and CPA Email Incident (00:33) - AI in QuickBooks: A Game Changer? (06:00) - Live Stream Shoutouts and YouTube Promotion (06:54) - New Legislation: Fiscal State of the Nation Act (10:37) - CPA Mobility and Alternative Pathways (11:47) - Guest Segment: Lindsay Patterson on CPA Mobility (33:13) - Deloitte's Bad Week: Controversies and Criticisms (35:58) - CPA Firms in Trouble: The Zwick CPA Case (40:05) - Jerome Powell's Defiant Statement (44:29) - Why Accountants Leave Public Accounting (51:24) - Listener Emails and Final Thoughts (52:08) - The Future of Accounting Jobs (55:12) - Private Equity in CPA Firms  Meet Lindsay Patterson: LinkedIn: https://www.linkedin.com/in/lindsaypatterson/Show NotesAICPA Urges Congressional Support for Fiscal State of the Nation Act https://www.aicpa-cima.com/news/article/aicpa-urges-congressional-support-for-fiscal-state-of-the-nation-actBarr Reintroduces Bipartisan Fiscal State of the Nation Act to Strengthen Oversight of Government Spending https://barr.house.gov/press-releases?id=EDF451C5-EEAE-44D7-85A8-2B714E9D7822For CPAs, one license — and 55 rulebooks https://www.accountingtoday.com/opinion/for-cpas-one-license-and-55-rulebooksDeloitte's Disturbing Pattern Allegedly Cost Americans Health Coverage, Delayed Benefits, and the US Government $74Bhttps://www.ibtimes.co.uk/deloittes-disturbing-pattern-allegedly-cost-americans-health-coverage-delayed-benefits-us-1773010Deloitte to ramp up India operations with 50,000 new hires https://www.internationalaccountingbulletin.com/news/deloitte-hiring-india/PCAOB Sanctions Audit Firm, an Owner of That Firm, and a Former Audit Manager for Multiple Violations of PCAOB Rules and Standardshttps://pcaobus.org/news-events/news-releases/news-release-detail/pcaob-sanctions-audit-firm--an-owner-of-that-firm--and-a-former-audit-manager-for-multiple-violations-of-pcaob-rules-and-standardsPCAOB bars Zwick CPA, owner and manager https://www.accountingtoday.com/news/pcaob-bars-zwick-cpa-owner-and-managerTurnover Experiences in Public Accounting and Alumni's Decisions to 'Give Back' https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4266300U.S. Accounting Undergraduate Enrollment Rises for Third Straight Year https://www.prnewswire.com/news-releases/us-accounting-undergraduate-enrollment-rises-for-third-straight-year-302665511.htmlAccounting undergrad enrollment rises for third year https://www.accountingtoday.com/news/accounting-undergrad-enrollment-rises-for-third-yearCapital One to Acquire Brex https://investor.capitalone.com/news-releases/news-release-details/capital-one-acquire-brexCapital One is buying startup Brex for $5.15 billion in credit card firm's latest deal https://www.cnbc.com/2026/01/22/capital-one-is-buying-startup-brex-for-5point15-billion-in-credit-card-firms-latest-deal.htmlFlorida Republican candidate suggests 'sin tax' for OnlyFans creators https://thehill.com/homenews/nexstar_media_wire/5691927-florida-governor-candidate-sin-tax/Florida gubernatorial candidate proposes 50% "sin" tax on OnlyFans creators; top earner Sophie Rain pushes backhttps://www.cbsnews.com/miami/news/florida-onlyfans-tax-proposal-james-fishback-sophie-rain/Need CPE?Get CPE for listening to podcasts with Earmark: https://earmarkcpe.comSubscribe to the Earmark Podcast: https://podcast.earmarkcpe.comGet in TouchThanks for listening and the great reviews! We appreciate you! Follow and tweet @BlakeTOliver and @DavidLeary. Find us on Facebook and Instagram. If you like what you hear, please do us a favor and write a review on Apple Podcasts or Podchaser. Call us and leave a voicemail; maybe we'll play it on the show. DIAL (202) 695-1040.SponsorshipsAre you interested in sponsoring The Accounting Podcast? For details, read the prospectus.Need Accounting Conference Info? Check out our new website - accountingconferences.comLimited edition shirts, stickers, and other necessitiesTeePublic Store: h...

Send us a textBrex was once valued at $12.3B. Capital One just bought it for $5.15B.In today's episode of Market Outsiders, Jenny Rae and Namaan break down why Capital One was willing to buy Brex at a $7B discount – and what the deal actually tells us about fintech valuations, banking strategy, and the future of credit cards.We unpack:Why the 50% cash / 50% stock structure reveals who really had leverageWhat Capital One is actually buyingWhether this is a smart buy vs. build move or a risky integration betThe bigger question: Is this how banks future-proof growth in financial services – or an example of catching a falling knife?Episode Links:Capital One is buying startup Brex for $5.15 billion in credit card firm's latest deal (CNBC)Partner Links:Learn more about NordStellar's Threat Exposure Management Program; unlock 10% off with code SIMPLIFIED-10Chapters:The $7B Brex DiscountWhat Brex Actually DoesWhy the $12B Valuation BrokeWhat Capital One Is BuyingCash vs. Stock LeverageRevenue Synergies vs. RiskFit with Capital One's Card StrategyMarket Reaction ExplainedSmart Bet or Falling KnifeConnect With Management Consulted Schedule free 15min consultation with the MC Team. Watch the video version of the podcast on YouTube! Follow us on LinkedIn, Instagram, and TikTok for the latest updates and industry insights! Join an upcoming live event - case interviews demos, expert panels, and more. Email us (team@managementconsulted.com) with questions or feedback.

In this episode of Run the Numbers, CJ sits down with Maria Izurieta, CFO of Huntress, to unpack what it really means to lead finance as a connective tissue across the organization. Drawing on experience across VC-backed, PE-owned, and public companies, Maria shares how she balances impact versus perfection, builds trust through small wins, and helps teams move from transactional finance to insight-driven decision making. They dig into data transparency, centralized BI, partnering with sales and marketing on revenue, and why the best CFOs unblock friction instead of becoming the “no” department — all while bringing a deeply people-first lens to scale.—SPONSORS:Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run—LINKS:Maria on LinkedIn: https://www.linkedin.com/in/maria-izurieta-909a3b/Company: https://www.huntress.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:How the Best CFOs Lead Without Being the CEO | Ken Stillwellhttps://youtu.be/O4cx9NBqQso—TIMESTAMPS:00:00:00 Preview and Intro00:01:01 Maria's Background00:03:09 People-First Team Building00:05:16 People, Process, Systems at Scale00:07:13 Removing Friction Outside Finance00:09:15 Data Transparency & Decision-Making00:11:06 Sponsors — Abacum | Brex | Metronome00:14:22 Forward-Deployed Data00:16:21 Centralized Data vs. Silos00:19:23 Finance as Data Steward00:21:08 Cost-to-Price Feedback Loop00:22:35 Curiosity Builds Credibility00:23:43 Sponsors — RightRev | Rillet | Tabs00:27:12 Trust First, Then Impact00:30:27 Celebrating Small Wins00:31:21 From Transactions to Insights00:33:00 CFO at the Revenue Table00:34:32 Educating the Org on Metrics00:36:21 Customer-Level Margin Reality00:37:13 Using Facts to Change Decisions00:38:27 Ownership Mindset in Growth Companies00:39:10 VC vs. PE vs. Public CFO Tradeoffs00:41:02 Operating Inside Constraints00:42:18 Finding Your Stage Fit00:44:17 Building a Personal Advisor Network00:46:43 Visibility and Women in Leadership00:47:44 Work–Life Integration, Not Balance00:48:45 Lightning Round: Biggest Mistake00:50:10 Advice to Younger Self00:51:36 Finance Tech Stack00:52:01 Craziest Expense Story00:52:44 Credits#RunTheNumbersPodcast #CFOLeadership #ScalingCompanies #DataDrivenDecisions #ExecutiveLeadership This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

成為這個頻道的會員並獲得福利：https://www.youtube.com/channel/UCJIPFjZSCWR15_jxBaK2fQQ/join前幾天看到新聞，我的前東家、曾經是矽谷最耀眼的 FinTech 獨角獸 Brex，正式被 Capital One 以 51.5 億美金收購。這個消息對我來說心情特別複雜，不只是因為這代表著一個時代的結束，更因為我曾身在其中，見證過它的瘋狂與轉折。你很難想像，這家公司的起點，是兩位來自巴西的 20 歲少年。他們 16 歲就靠賣掉支付公司財富自由，為了進入矽谷核心圈申請上 Stanford，最後卻因為「身價千萬卻辦不到一張美國信用卡」的荒謬痛點，決定輟學創辦 Brex，發誓要顛覆傳統銀行。九年過去了，這場金融革命的結局不是上市敲鐘，而是估值腰斬，賣給了它原本最想取代的對手。這集影片不只是商業新聞的分析，我整理了 Brex 創辦人的傳奇發跡史、它與競爭對手 Ramp 之間的「哲學之戰」：當「鼓勵花錢」遇上「幫你省錢」，為何在升息循環下命運截然不同？更重要的是，我想用「前員工」的內部視角，公開我當時的 Offer 與最終的 RSU 回報，直接算給你看：在獨角獸公司打工，還要經歷併購的層層資金分配後，到底是財富自由的捷徑，還是一場華麗的賭注？這是一個關於天才、野心、時運，以及矽谷打工人真實回報的故事。本集精彩亮點： 

Send us a textInvest in pre-IPO stocks with AG Dillon & Co. Contact aaron.dillon@agdillon.com to learn more. Financial advisors only. www.agdillon.com00:00 - Intro00:07 - ClickHouse $400M Series D $15B Valuation Langfuse M&A01:29 - Runpod $120M Run Rate 500K Developers 31 Regions02:59 - Humans& $480M Seed $4.48B Valuation 3 Months Old04:03 - Baseten $300M Raise $5B Valuation Nvidia $150M04:49 - Noveon Magnetics $215M Raise 2,000+ Tons Per Year Target06:17 - Zipline $600M+ New Funding $7.6B Valuation 2M+ Deliveries07:34 - Hatch Yelp Acquisition $300M Deal 12x ARR08:26 - Brex Capital One Acquisition $5.15B Deal $13B Deposits09:30 - DayOne Data Centers IPO Target Up to $20B10:14 - World Labs Funding Talks at $5B Potential $500M Balance Sheet Add11:08 - TikTok US New Entity 50% New Investors 200M US Users12:42 - Inferact $150M Seed $800M Valuation vLLM Commercialization13:16 - RadixArk $400M Valuation SGLang Commercial Push14:07 - Blue Origin TeraWave 6 Tbps 5,408 Satellites Q4 2027 Deployment15:15 - OpenAI Shopify Checkouts Jan 26 Launch 4% ChatGPT Fee16:24 - OpenAI API Revenue +$1B ARR in One Month $20B+ Total ARR16:51 - OpenAI Ads Testing Coming Weeks Go Plan Included17:31 - OpenAI ServiceNow 3-Year Enterprise Integration

Ok, ok, maybe the whole TikTok thing is a done deal at long last? Amazon is planning another major round of layoffs. Are Epic Games and Google doing an end-run around the judge? Capital One acquires Brex. And, of course, The Weekend Longreads Suggestions. Trump's TikTok deal is a gift to China (FT) Exclusive: Amazon plans thousands more corporate job cuts next week, sources say (Reuters) Epic and Google have a secret $800 million Unreal Engine and services deal (The Verge) Apple Expands Hardware Chief's Role (Bloomberg) Capital One Strikes $5.15 Billion Deal for Fintech Brex (WSJ) Weekend Longreads Suggestion: Russia, Ukraine and the race for Chinese drone components (FT) Learn more about your ad choices. Visit megaphone.fm/adchoices

Capital One's (COF) earnings miss and acquisition of fintech firm Brex have shares under pressure to end the trading week. Diane King Hall helps investors break down the latest quarterly report. On a positive note, TD Cowen upgraded Fortinet (FTNT) as it sees AI tailwinds for the company. Spotify (SPOT) got an upgrade and price target hike from Goldman Sachs following a months-long sell-off. ======== Schwab Network ========Empowering every investor and trader, every market day.Subscribe to the Market Minute newsletter - https://schwabnetwork.com/subscribeDownload the iOS app - https://apps.apple.com/us/app/schwab-network/id1460719185Download the Amazon Fire Tv App - https://www.amazon.com/TD-Ameritrade-Network/dp/B07KRD76C7Watch on Sling - https://watch.sling.com/1/asset/191928615bd8d47686f94682aefaa007/watchWatch on Vizio - https://www.vizio.com/en/watchfreeplus-exploreWatch on DistroTV - https://www.distro.tv/live/schwab-network/Follow us on X – https://twitter.com/schwabnetworkFollow us on Facebook – https://www.facebook.com/schwabnetworkFollow us on LinkedIn - https://www.linkedin.com/company/schwab-network/About Schwab Network - https://schwabnetwork.com/about

HSBC's Frank Lee talks with TITV Host Akash Pasricha about Intel's disappointing revenue guidance and capacity constraints despite the AI boom. We also talk with BitGo CEO Mike Belshe about their public debut and the shift toward retail-driven IPOs, and The Information's Laura Mandaro about Capital One's $5.15 billion acquisition of Brex. We then get into the reality behind the TikTok deal and OpenAI's ad testing with editors Martin Peers and Meredith Mazzilli. Finally, we go inside the political transformation of OpenAI President Greg Brockman with reporters Stephanie Palazzolo and Jemima McEvoy.Articles discussed on this episode: https://www.theinformation.com/articles/intel-now-pricier-tsmc-makes-sensehttps://www.theinformation.com/newsletters/the-briefing/brexit-fintechhttps://www.theinformation.com/newsletters/dealmaker/exit-brex-investors-rising-zombie-fundshttps://www.theinformation.com/briefings/tiktok-completes-sale-data-security-arm-joint-ventureSubscribe: YouTube: https://www.youtube.com/@theinformation The Information: https://www.theinformation.com/subscribe_hSign up for the AI Agenda newsletter: https://www.theinformation.com/features/ai-agendaTITV airs weekdays on YouTube, X and LinkedIn at 10AM PT / 1PM ET. Or check us out wherever you get your podcasts.Follow us:X: https://x.com/theinformationIG: https://www.instagram.com/theinformation/TikTok: https://www.tiktok.com/@titv.theinformationLinkedIn: https://www.linkedin.com/company/theinformation/

In this episode of Run the Numbers, CJ sits down with Ken Stillwell, CFO and COO of Pegasystems, to explore the realities of leading from the second seat. Ken shares hard-earned lessons from guiding Pega through the shift from term licenses to ARR and ACV, including how to rework sales compensation without losing trust or momentum. They discuss the limits of KPI obsession, the importance of directional clarity over false precision, and why private equity often drives sharper execution than public markets—and how to apply that discipline while still playing the long game.—SPONSORS:Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cj—LINKS:Ken on LinkedIn: https://www.linkedin.com/in/ken-stillwell-83a499a/Pegasystems: https://www.pega.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubakerhttps://youtu.be/T2YjdoiJtFA—TIMESTAMPS:00:00:00 Preview and Intro00:02:57 Sponsors — Tabs | Abacum | Brex00:07:26 The Strategic Value of Being Number Two00:08:46 Earnings Calls, Messaging, and Real-Time Judgment00:10:41 Using Feedback to Sharpen Executive Communication00:11:38 CFOs as Storytellers & Message Repetition00:12:31 Managing Up: Reading the Room00:13:59 Learning the Hard Way: Misreading Dynamics00:15:18 Confidence, Aggression, and Early CFO Mistakes00:15:58 Sponsors — Metronome | RightRev | Rillet00:19:45 When to Email vs Pick Up the Phone00:22:48 Tailoring Communication to Different Functions00:23:23 Audience-Specific Messaging: “Why Me?”00:25:24 Values vs Behaviors in Leadership00:28:13 Why Big Changes Need Anchoring00:31:14 Moving Pega to the Cloud00:32:43 Rewiring Sales Comp for ARR & ACV00:34:56 Sales Credibility Breakdowns with Customers00:36:20 Economics vs Trust in Sales Teams00:37:48 Balancing Field Feedback with Company Goals00:39:17 De-Emphasizing New Logos to Fix the Sales Model00:41:12 The Danger of Over-Obsessing on KPIs00:42:51 Public vs Private: Incentives and Operating Discipline00:45:57 Why Companies Go Private: Motivation Over Patience00:47:29 The Shrinking Public Markets00:47:57 Private vs Public CFO Mindsets00:49:39 Meeting Investors Where They Are00:50:16 A Risky Decision That Paid Off: Going All-In on the Cloud00:51:29 Long-Ass Lightning Round00:53:24 Ken's Finance Tech Stack & Craziest Expense00:54:39 Credits#RunTheNumbersPodcast #CFOLeadership #ExecutiveCommunication #SalesStrategy #PublicVsPrivate This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Tyson Singer (Head of Tech & Platforms @ Spotify) joins us to unpack how Spotify is transforming its product development lifecycle across creation, experimentation and maintenance to shift from "localized speed" to "systematic speed." We explore why the industry's current obsession with the "Build It" phase of development is shortsighted, and how Spotify is aggressively deploying AI in the "Think It" (prototyping/strategy) and "Maintain It" (fleet management) phases. Tyson also details the internal tools driving this shift, including AiKA and Honk, and shares why the future of engineering relies on moving from I-shaped specialists to T-shaped generalists. ABOUT TYSON SINGERTyson Singer is the SVP of Technology & Platforms at Spotify, where he leads technology infrastructure, developer experience, cybersecurity, and finance IT. Tyson is the executive behind Spotify's internal developer portal, Backstage, and Spotify's experimentation system, Confidence, which are now both commercially available. He has a background as an engineer, architect, and product lead, and he holds a Master's in Computer Science from Stanford University. Tyson is also an avid outdoor adventurer. This episode is brought to you by Retool!What happens when your team can't keep up with internal tool requests? Teams start building their own, Shadow IT spreads across the org, and six months later you're untangling the mess…Retool gives teams a better way: governed, secure, and no cleanup required.Retool is the leading enterprise AppGen platform, powering how the world's most innovative companies build the tools that run their business. Over 10,000 organizations including Amazon, Stripe, Adobe, Brex, and Orangetheory Fitness use the platform to safely harness AI and their enterprise data to create governed, production-ready apps.Learn more at Retool.com/elc SHOW NOTES:Tyson's 9-year journey @ Spotify: From the "crucible" of hyper-growth to leading Tech & Platforms (3:46)The pivot from "localized speed" to "systematic speed" (7:27)Core principles of Spotify's Platform org: Partnering with customers & "Taking the pain away" (10:37)The "Think it, Build it, Ship it, Tweak it" lifecycle framework & why the industry obsession with "Build It" (coding agents) is missing the bigger picture (14:57)How Spotify is investing in the "Think It" phase: AI prototyping with deep business context (16:49)AiKA (AI Knowledge Assistant): Context engineering for humans and bots (18:47)"Honk": Spotify's internal framework for large-scale automated code changes (22:17)Addressing the decline of code quality and the bottleneck of human PR reviews (25:50)Probabilistic vs. Deterministic code reviews: A new approach to quality checks (29:43)Identifying bottlenecks to company value outside of R&D (Legal, Licensing, etc.) (32:12)Why systems change is fundamentally about people and identity shifts (35:57)Rapid fire questions (38:49) This episode wouldn't have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan's also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

This week we chat with Haseeb Qureshi!Haseeb is the Managing Partner at Dragonfly, a multibillion-dollar leading crypto VC firm, and is a longtime technology-focused crypto investor.He was previously a General Partner at Metastable Capital (now acquired by Dragonfly). Earlier in his career, Haseeb founded a stablecoin startup, worked as a blockchain engineer at Earn.com (acquired by Coinbase), and served as an anti-fraud engineer at Airbnb. Before entering tech, he was among the top heads-up no-limit Hold'em poker players in the world, becoming a sponsored professional and self-made millionaire by age 19. He later authored a best-selling poker book, donated the bulk of his poker earnings—about half a million dollars—to charity, and pursued an earn-to-give path that led him into software engineering and eventually blockchain.Haseeb has taught a Web3 Entrepreneurship course at UC Berkeley and is widely followed for his technical expertise in crypto. Today, he continues to write, invest, and contribute to the ecosystem while committing a third of his pre-tax income to charitable causes.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Haseeb Qureshi: @hosseeb@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

In this episode of Run the Numbers, CJ sits down with Chris Brubaker, SVP of Finance at Postscript, who's helped build the finance function from the ground up. Chris shares how he partners with sales through deal desks, sets pricing guardrails, and makes sure finance helps close deals instead of slowing them down. They dig into his hands-on approach to automation using AI with limited engineering resources, how Postscript's metrics evolved as the company scaled, when to trust internal data over benchmarks, and where teams get tripped up. Plus, a private jet accounting story—because of course.—SPONSORS:Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com—LINKS:Chris on LinkedIn: https://www.linkedin.com/in/wchrisbrubaker/Postscript: https://postscript.io/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:So You're Looking for a “Strategic” CFO? Bloomerang's Steve Isom on What That Really Meanshttps://youtu.be/cgHOtvG1CesThe IPO Playbook: Expert Advice from Lee Kirkpatrick, Twilio's Former CFOhttps://youtu.be/PTKAUD7PSWUThe CFO Case for Probabilistic Forecasting With AI | Bruno Annicqhttps://youtu.be/Dl8nDZPJMpE—TIMESTAMPS:00:00:00 Preview and Intro00:02:22 Sponsors — Rillet | Tabs | Abacum00:06:55 Interview Begins00:07:36 First Finance Hire and Early Scale at Postscript00:09:02 Usage-Based Margins, COGS, and the Twilio Parallel00:10:31 Partnering With Sales and Building Deal Desk00:13:16 Pricing Guardrails, Payback, and Deal Economics00:15:35 How Deal Desk Evolves Over Time00:16:01 Sponsors — Brex | Metronome | RightRev00:19:44 Making Finance a Deal-Closing Partner00:20:44 Automating Deal Desk With a Slack Bot00:23:48 How Technical Finance Leaders Need to Be00:25:17 Automating Without Engineering Help00:27:12 Why Human Touch Still Matters in SaaS00:27:53 Postscript's Finance Tech Stack00:28:30 ERP Migration and Month-End Efficiency00:29:42 The Reality of Continuous Close00:30:34 First Real AI Wins in Accounting00:31:18 Experimenting With AI Forecasting00:33:32 Metrics That Matter: Usage as a Leading Indicator00:35:49 How Metrics Evolve as the Company Scales00:37:41 Understanding the Product in a Usage-Based Model00:39:27 Micro-Seasonality and Forecasting Volatility00:42:21 How to Use Benchmarks Without Misusing Them00:43:50 Long-Ass Lightning Round: A Costly Modeling Mistake00:45:45 Advice to a Younger Finance Leader00:47:05 The Private Jet Accounting Story00:49:11 Credits#RunTheNumbersPodcast #FinanceLeadership #DealDesk #UsageBasedSaaS #AIinFinance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

From building internal AI labs to becoming CTO of Brex, James Reggio has helped lead one of the most disciplined AI transformations inside a real financial institution where compliance, auditability, and customer trust actually matter. We sat down with Reggio to unpack Brex's three-pillar AI strategy (corporate, operational, and product AI) [https://www.brex.com/journal/brex-ai-native-operations], how SOP-driven agents beat overengineered RL in ops, why Brex lets employees “build their own AI stack” instead of picking winners [https://www.conductorone.com/customers/brex/], and how a small, founder-heavy AI team is shipping production agents to 40,000+ companies. Reggio also goes deep on Brex's multi-agent “network” architecture, evals for multi-turn systems, agentic coding's second-order effects on codebase understanding, and why the future of finance software looks less like dashboards and more like executive assistants coordinating specialist agents behind the scenes. We discuss: Brex's three-pillar AI strategy: corporate AI for 10x employee workflows, operational AI for cost and compliance leverage, and product AI that lets customers justify Brex as part of their AI strategy to the board Why SOP-driven agents beat overengineered RL in finance ops, and how breaking work into auditable, repeatable steps unlocked faster automation in KYC, underwriting, fraud, and disputes Building an internal AI platform early: LLM gateways, prompt/version management, evals, cost observability, and why platform work quietly became the force multiplier behind everything else Multi-agent “networks” vs single-agent tools: why Brex's EA-style assistant coordinates specialist agents (policy, travel, reimbursements) through multi-turn conversations instead of one-shot tool calls The audit agent pattern: separating detection, judgment, and follow-up into different agents to reduce false negatives without overwhelming finance teams Centralized AI teams without resentment: how Brex avoided “AI envy” by tying work to business impact and letting anyone transfer in if they cared deeply enough Letting employees build their own AI stack: ChatGPT vs Claude vs Gemini, Cursor vs Windsurf, and why Brex refuses to pick winners in fast-moving tool races Measuring adoption without vanity metrics: why “% of code written by AI” is the wrong KPI and what second-order effects (slop, drift, code ownership) actually matter Evals in the real world: regression tests from ops QA, LLM-as-judge for multi-turn agents, and why integration-style evals break faster than you expect Teaching AI fluency at scale: the user → advocate → builder → native framework, ops-led training, spot bonuses, and avoiding fear-based adoption Re-interviewing the entire engineering org: using agentic coding interviews internally to force hands-on skill upgrades without formal performance scoring Headcount in the age of agents: why Brex grew the business without growing engineering, and why AI amplifies bad architecture as fast as good decisions The future of finance software: why dashboards fade, assistants take over, and agent-to-agent collaboration becomes the real UI — James Reggio X: https://x.com/jamesreggio LinkedIn: https://www.linkedin.com/in/jamesreggio/ Where to find Latent Space X: https://x.com/latentspacepod Substack: https://www.latent.space/ Chapters 00:00:00 Introduction 00:01:24 From Mobile Engineer to CTO: The Founder's Path 00:03:00 Quitters Welcome: Building a Founder-Friendly Culture 00:05:13 The AI Team Structure: 10-Person Startup Within Brex 00:11:55 Building the Brex Agent Platform: Multi-Agent Networks 00:13:45 Tech Stack Decisions: TypeScript, Mastra, and MCP 00:24:32 Operational AI: Automating Underwriting, KYC, and Fraud 00:16:40 The Brex Assistant: Executive Assistant for Every Employee 00:40:26 Evaluation Strategy: From Simple SOPs to Multi-Turn Evals 00:37:11 Agentic Coding Adoption: Cursor, Windsurf, and the Engineering Interview 00:58:51 AI Fluency Levels: From User to Native 01:09:14 The Audit Agent Network: Finance Team Agents in Action 01:03:33 The Future of Engineering Headcount and AI Leverage

In this episode of Run the Numbers, CJ sits down with Bruno Annicq, CFO of Wellhub (formerly Gympass), to unpack a practical finance playbook built around cash discipline, sustainable growth, and simplicity. Bruno explains how he rebuilt forecasting using an AI-driven, probabilistic ensemble model, moving teams beyond single-scenario planning. They also dig into his EMPOWER planning framework, usable OKRs, and why tighter alignment between finance, HR, and wellbeing is becoming a durable lever for long-term performance.—SPONSORS:RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com—LINKS:Bruno on LinkedIn: https://www.linkedin.com/in/bannicq/Wellhub: https://wellhub.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:“Run Toward a Tough Market” — Developing the Hard and Soft Skills To Be a Great Finance Leaderhttps://youtu.be/iNHbkcG7YEo—TIMESTAMPS:00:00:00 Preview and Intro00:02:19 Sponsors — RightRev, Rillet, Tabs00:06:43 Accidental CFO Origin Story00:07:34 Consulting to Operations Pivot00:08:12 Why Finance Clicked for Bruno00:09:28 McKinsey Prioritization in Real World00:10:02 Eisenhower Matrix and Prioritization00:11:08 Investing in Non-Urgent Work00:13:30 Lessons From AOL Reinvention00:16:10 Sponsors — Abacum, Brex, Metronome00:20:01 Career Growth Through Hard Problems00:20:52 Broadening Skills Through Change00:23:12 Five Core Finance Principles00:24:02 Cash Is King00:25:14 Driving Sustainable Growth00:26:01 No Surprises and Forecasting00:26:07 Finance as Business Enabler00:27:22 Less Is More Philosophy00:28:47 Hardest Principle: Less Is More00:29:46 Deterministic vs Probabilistic Forecasting00:31:11 Marketplace Volatility and Forecast Error00:32:10 Ensemble Models Explained00:33:37 Forecast Accuracy Gains00:34:53 Building Models In-House00:36:46 Why Explainability Matters00:37:48 Empower Framework Introduction00:47:47 Urgency, Compounding, Long-Term Thinking00:48:10 Advice to Younger Self00:50:06 Finance Stack and Expense Stories00:52:51 Credits#RunTheNumbersPodcast #CFO #FinanceLeadership #Forecasting #AIinFinance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

This week, we chat with Nicolas Cary! Nic is the Co-Founder and Vice Chairman at Blockchain.com! He is responsible for bringing new adopters into the crypto ecosystem. A fascination with tech, money and politics led Nic to become deeply passionate about helping people reinvent their relationship with money.After an international upbringing, Nic worked as a teacher in India before becoming a founding team member at SaaS company PipelineCRM.com, where he focused on product development and management.A trilingual communicator, Nic is the Founding Commissioner of the Blockchain Commission for Sustainable Development and co-author of The Future is Decentralised. Deeply passionate about entrepreneurship, Nic is also co-founder and chairman of SkysTheLimit.org, the leading non-profit digital business accelerator. Regularly cited in the global press as one of the earliest crypto industry experts, Nic was named the European Digital Leader of the year in 2015 and honored with a Professional Achievement Award in 2017 by his alma mater, the University of Puget Sound.A proven leader, investor, public speaker, and brand ambassador, Nic focuses on designing performant cultures that persevere in adverse markets.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Nicolas Cary: @niccarySky's The Limit: https://www.skysthelimit.org/@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

In this episode of Run the Numbers, CJ sits down with Jason Kong, General Partner at Base10 Ventures, to unpack the firm's focus on “automation for the real economy” — software built for industries most tech investors overlook, but the world depends on. Jason breaks down what makes Series B investing uniquely hard, how he evaluates back-office and vertical SaaS opportunities, and where markets tip from niche to overcrowded. They also discuss Base10's decision to donate 50% of profits to fund scholarships, plus a lightning round spanning fantasy football, shorting SaaS in 2022, and a venture take that might spark debate.—SPONSORS:Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics—LINKS:Jason on LinkedIn: https://www.linkedin.com/in/jasonykong/Base10 Partners: https://base10.vc/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillipshttps://youtu.be/vBY6WZBMljw—TIMESTAMPS:00:00:00 Preview and Intro00:02:20 Sponsors — Metronome, RightRev, Rillet00:06:02 Base10 Background00:06:41 Automation for the Real Economy00:09:27 Vertical vs. Horizontal Software00:10:38 Cash Flow and Durability00:11:19 Product-Market Fit and ROI00:12:56 Growth Limits Selling to Tech00:13:19 The Size of the Real Economy00:14:16 Sponsors — Tabs, Abacum, Brex00:18:50 Base10's Giving Model00:20:30 Access, Education, and Tech00:21:53 Purpose and Founder Alignment00:22:51 Radical Transparency00:23:56 Portfolio Focus and Strategy00:24:05 Investing Ahead of Consensus00:26:29 ERP Adjacency as Alpha00:28:58 Lessons From Hedge Funds00:32:29 Public Markets Reality00:34:05 Public vs. Private Investing00:34:48 The Series B Sweet Spot00:36:49 A Bifurcated Series B Market00:38:56 Fast Series Bs and 2021 Vibes00:42:16 What Series B Looks Like Now00:44:36 Back Office Automation00:46:02 ERP-Centric Workflows00:48:33 Long-Ass Lightning Round00:49:36 Shorting SaaS in 202200:50:16 Fantasy Football and Investing00:52:57 Career Advice That Surprises00:55:03 A Contrarian Venture Take00:56:22 Credits#RunTheNumbersPodcast #SeriesB #RealEconomy #VerticalSaaS #BackOfficeAutomation This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ sits down with Dominic Phillips, CFO of Samsara, to unpack what it takes to scale a capital-intensive SaaS business from startup to public company in under a decade. Dominic reflects on his six-plus years at Samsara through hypergrowth, COVID disruption, supply chain constraints, a down-round survival raise, and an IPO at the very end of the 2021 tech window. Drawing on his earlier career at ServiceNow under Mike Scarpelli, he shares how experience across FP&A, IR, corp dev, and treasury shaped his approach to capital allocation, investor education, and analyst management. The conversation dives into asset-based pricing, selling into non-discretionary operations budgets, balancing hardware and software economics, and building credibility with a broad analyst base while scaling past $1B in ARR.—SPONSORS:Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/runAbacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai—LINKS:Dominic on LinkedIn: https://www.linkedin.com/in/dominicphillips/Company: https://www.samsara.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:“Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & Growthhttps://youtu.be/VRpTNDIfzPYFrom SMB to Enterprise: The CFO Scaling Playbook With Andrew Casey | Mostly Classicshttps://youtu.be/kMuJ6gAuEpgDriving revenue without selling | Greg Henry of 1Passwordhttps://youtu.be/f5FsNoG8A3E—TIMESTAMPS:00:00:00 Preview & Intro00:02:40 Sponsors — Brex | Metronome | RightRev00:06:18 Interview Begins00:06:46 Dominic's Early Career00:08:47 From ServiceNow to CFO00:09:47 Joining Samsara00:10:54 COVID, Burn, and a Down Round00:12:40 IPO Messaging and Investor Education00:15:50 Sponsors — Rillet | Tabs | Abacum00:20:27 Hardware + Software Story00:21:29 What Samsara Does00:22:30 Data, AI, and ROI00:23:23 Horizontal Platform and Verticals00:24:27 Growth Drivers at Scale00:26:09 Selling Into Operations00:28:19 Change Management in Legacy Orgs00:29:46 Non-Discretionary Budgets00:33:02 Storytelling Lessons from Scarpelli00:36:14 Managing Analysts00:39:23 Earnings Timing Strategy00:41:06 Metrics and Investor Trust00:42:38 Investor Communication Channels00:44:22 Investor Days and Long-Term Vision00:45:37 Annual Planning Maturity00:48:24 Forecast Accuracy and Cadence00:49:28 The 1000-Day Strategy00:50:40 Top-Line and Margin Targets00:51:59 Capital Allocation by Function00:54:46 Becoming a CFO00:58:21 Lightning Round and a CFO Mistake01:02:41 End Credits#RunTheNumbersPodcast #CFO #ScalingCompanies #B2BSaaS #PublicMarkets This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

In this episode of Run the Numbers, CJ Gustafson sits down with Gordon Coyle, a 40-year commercial insurance veteran, to demystify one of the most anxiety-inducing topics for founders and CFOs: business insurance. Drawing on decades of experience with startups, scaleups, and regulated industries, Gordon breaks down what leaders need to know about D&O, E&O, cyber, and general liability, why investor pressure is rising, and where “cheap and easy” online policies fail when real risk hits. Through real-world examples, they explore how claims arise, how defense costs erode limits, why cyber insurance is as much about response as reimbursement, and how to balance budget, risk tolerance, and peer benchmarks—treating insurance as a critical layer of protection, not a box-checking exercise.—SPONSORS:Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.aiBrex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metricsMetronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comRightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.comRillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you're scaling on an ERP that wasn't built in the 90s, book a demo at https://www.rillet.com/cjTabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run—LINKS:Gordon on LinkedIn: https://www.linkedin.com/in/gordoncoyle/The Coyle Group: https://thecoylegroup.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:The Coyle Group - Business Insurancehttps://www.youtube.com/@TheCoyleGroupNY—TIMESTAMPS:00:00:00 Preview and Intro00:01:53 Sponsors — Abacum | Brex | Metronome00:05:39 Interview Begins with Gordon Coyle00:06:23 Gordon Coyle & The Coyle Group00:07:21 Explaining Insurance on YouTube00:08:40 Turning Education into Inbound Leads00:09:40 Content as a Pull Strategy00:10:53 Insurance Complexity for Tech Founders00:13:28 Why Investors Require D&O Insurance00:14:09 What D&O Covers and Why It Matters00:15:50 Sponsors — RightRev | Rillet | Tabs00:20:19 Who D&O Covers and Rising Investor Pressure00:22:37 D&O Limits and Cost Tradeoffs00:23:21 Panic Calls and Late D&O Purchases00:24:39 How Defense Costs Erode Coverage00:25:31 Common D&O Claims and Employment Risk00:27:08 D&O vs E&O Explained00:29:12 Cyber Insurance and Social Engineering00:31:59 AI's Impact on Cyber Risk00:33:50 Real-World Ransomware Stories00:34:17 Cyber Insurance as Money and Response00:35:29 Business Email Compromise Scams00:39:43 Why Tech Still Needs General Liability00:41:16 What a BOP Covers00:42:32 Convenience vs Proper Coverage00:44:29 Surprising General Liability Claims00:46:45 Insurance Costs for Startups00:47:36 Higher Costs in High-Risk Industries00:48:26 Balancing Budget, Risk, and Coverage00:50:39 PEOs, Workers' Comp, and EPLI00:54:39 Choosing the Right Insurance Partner00:56:42 End Credits#RunTheNumbersPodcast #StartupFinance #BusinessInsurance #RiskManagement #CyberRisk This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

Jason Lemkin is the founder of SaaStr, the world's largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn't, and how the GTM landscape is quickly being transformed.We discuss:1. How AI is fundamentally changing the sales function2. Why most SDRs and BDRs will be “extinct” within a year3. What Jason is observing across his portfolio about AI adoption in GTM4. How to become “hyper-employable” in the age of AI5. The specific AI tools and tactics he's using that have been working best6. Practical frameworks for integrating AI into your sales motion without losing what works7. Jason's 2026 predictions on where SaaS and GTM are heading next—Brought to you by:DX—The developer intelligence platform designed by leading researchersVercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the webDatadog—Now home to Eppo, the leading experimentation and feature flagging platform—Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation—Where to find Jason Lemkin:• X: https://x.com/jasonlk• LinkedIn: https://www.linkedin.com/in/jasonmlemkin• Website: https://www.saastr.com• Substack: https://substack.com/@cloud—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jason Lemkin(04:36) What SaaStr does(07:13) AI's impact on sales teams(10:11) How SaaStr's AI agents work and their performance(14:18) How go-to-market is changing in the AI era(19:19) The future of SDRs, BDRs, and AEs in sales(22:03) Why leadership roles are safe(23:43) How to be in the 20% who thrive in the AI sales future(28:40) Why you shouldn't build your own AI tools(30:10) Specific AI agents and their applications(36:40) Challenges and learnings in AI deployment(42:11) Making AI-generated emails good (not just acceptable)(47:31) When humans still beat AI in sales(52:39) An overview of SaaStr's org(53:50) The role of human oversight in AI operations(58:37) Advice for salespeople and founders in the AI era(01:05:40) Forward-deployed engineers(01:08:08) What's changing and what's staying the same in sales(01:16:21) Why AI is creating more work, not less(01:19:32) Why Jason says these are magical times(01:25:25) The "incognito mode test" for finding AI opportunities(01:27:19) The impact of AI on jobs(01:30:18) Lightning round and final thoughts—Referenced:• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org• SaaStr Annual: https://www.saastrannual.com• Delphi: https://www.delphi.ai/saastr/talk• Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/• Vercel: https://vercel.com• What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently• Everyone's an engineer now: Inside v0's mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch• Replit: https://replit.com• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad• ElevenLabs: https://elevenlabs.io• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack• Bolt: https://bolt.new• Lovable: https://lovable.dev• Harvey: https://www.harvey.ai• Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence• UiPath: https://www.uipath.com• Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser• Agentforce: https://www.salesforce.com/form/agentforce• SaaStr's AI Agent Playbook: https://saastr.ai/agents• Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan• Brian Halligan's AI: https://www.delphi.ai/minds/bhalligan• Sierra: https://sierra.ai• Fin: https://fin.ai• Deccan: https://www.deccan.ai• Artisan: https://www.artisan.co• Qualified: https://www.qualified.com• Claude: https://claude.ai• HubSpot: https://www.hubspot.com• Gamma: https://gamma.app• Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b• Brex: https://www.brex.com• Outreach: https://www.outreach.io• Gong: https://www.gong.io• Salesloft: https://www.salesloft.com• Mixmax: https://www.mixmax.com• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr• Clay: https://www.clay.com• Owner: https://www.owner.com• Momentum: https://www.momentum.io• Attention: https://www.attention.com• Granola: https://www.granola.ai• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• Palantir: https://www.palantir.com• Databricks: https://www.databricks.com• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan• Rippling: https://www.rippling.com• Cursor: https://cursor.com• The rise of Cursor: The $300M ARR AI tool that engineers can't stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna• Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza• Sora: https://openai.com/sora• Reve: https://app.reve.com• Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/• The Revenue Playbook: Rippling's Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Today on HR Heretics, we're excited to cross post a forward-thinking dialogue from Metaview's 10x Recruiting Podcast on 2026 recruiting predictions, examining AI's transformative impact on talent acquisition, compensation dynamics, agent orchestration, and the evolving relationship between human expertise and algorithmic screening.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* 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.KEEP UP WITH SIADHAL, NOLAN + KELLI ON LINKEDINSiadhal: https://www.linkedin.com/in/siadhal/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__LINKS:For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Introduction: 2026 Predictions Episode Setup(01:00) Prediction #1: The VC Talent Partner Exodus to AI Companies(05:00) Prediction #2: AI Becomes the Default First Screen for Inbound(12:00) Prediction #3: The ATS Becomes Invisible(14:00) Prediction #4: 90% of Sourcing Will Be Automated(15:00) Prediction #5: Outreach Automation Will Be an Unmitigated Disaster(22:00) Sponsor: Metaview(23:00) Prediction #6: Backlash Against Human Data Extraction(26:00) Prediction #7: Social Unrest from White Collar Tech Workers(31:00) Prediction #8: Agent Managers Emerge as High-Status Roles(36:00) Prediction #9: Crazy Comp Packages for Non-Technical Talent(43:00) Prediction #10: Foundation Labs Move Deeper Into Applications(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

For today's essential Heretics 101 feature, executive coach Nathan Tanner reveals the real economics of coaching: transparent revenue breakdowns, pricing strategy, and the path from corporate burnout to independent practice. Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* 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.KEEP UP WITH NATHAN, NOLAN + KELLI ON LINKEDINNathan: https://www.linkedin.com/in/nathantanner/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__LINKS:For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(01:41) The breakdown story (crying on floor)(05:49) “Weekend warriors” critique(09:00) Fire your coach every year?(10:03) Sponsor: Metaview(12:47) $240K → $335K revenue reveal(14:20) First full year: $335K breakdown(19:14) “Hire Nathan or do nothing” strategy(22:16) Burning the boats philosophy 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

This week we chat with Paige Finn Doherty!Paige is the Founding Partner of Behind Genius Ventures, an early-stage venture firm managing nearly $14 million in AUM. Behind Genius makes concentrated investments in pre-seed and seed-stage companies led by technical storytellers across applied AI, frontier tech, and what's next.A writer and former engineer, Paige first broke into venture capital in a truly unconventional way by writing a best-selling “children's book for adults” about how venture capital works, Seed to Harvest. At the time, she was working as a Developer Success Engineer at WorkOS, a role she actually landed through Twitter!Paige's impact and storytelling have earned her widespread recognition: she was featured on the Forbes 30 Under 30 Cover in Venture Capital (2022), named a Rising SDSU Aztec Awardee, and most recently, inducted into the Rancho Bernardo High School Hall of Fame.Originally from San Diego and now based in San Francisco, Paige continues to bring transparency, creativity, and heart to the world of venture through storytelling and curio✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Paige Finn Doherty: @paigedohertyBehind Genius Substack: @behindgenius.substack.com@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

For today's essential Heretics 101 feature, Chris Yeh discusses infinite learning, staying relevant through younger generations, Blitzscaling adaptability principles, assessing founders through shared experiences, and negotiating equity by establishing fair processes before debating numbers.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* 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.KEEP UP WITH CHRIS, NOLAN + KELLI ON LINKEDINChris: https://www.linkedin.com/in/chrisyeh/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__LINKS:For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Introduction: Infinite Learning & Blitzscaling Adaptability(01:00) The Source of Energy, Public Speaking & Performance Background(02:00) The Power of Unlearning & Staying Relevant(04:08) Blitzscaling: Hiring for Adaptability & Resilience(07:12) Picking Companies: Thinking Like an Investor(09:08) Assessing Founders: The Travel & Summer Camp Effect(10:14) Sponsor: Metaview(11:36) Negotiating Founder Shares & Equity Splits(17:00) Compensation Philosophy & The Numbers Hack(19:13) 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

One of our biggest episodes of this past year was with Zapier's CPO Brandon Sammut, ICYMI or as a refresher, in this essetial Heretics 101 feature, he demonstrates AI agents transforming HR workflows: from automating bar raiser interview prep to performance evidence collection, while explaining their four-level AI fluency framework.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* 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.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__LINKS:For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(00:26) Why AI Fluency is Required for 100% of New Hires(02:00) The 4-Level AI Fluency Rubric: Capable to Transformational(03:38) Demo 1: Bar Raiser Interview Agent(04:33) 730 Employees, 10 VPs - Job Level Discipline(05:47) Agent Explains WHY It Chose Each Question(06:27) The Spectrum of AI Interview Approaches(08:18) Demo 2: Performance Review Evidence Collection(09:21) The Blob Notes Emoji: Triggering Evidence Collection(10:33) Don't Let Perfect Be the Enemy of Good(11:21) Future Vision: AI Coach Idling in Slack(13:25) “It's Like Steroids” - Not AI Overlords Taking Over(13:51) Sponsor: Metaview(15:41) Live Demo: Blob Notes in Action(18:13) Employee Choice vs Mandates: Marketing Over Requirements(19:27) Leadership Doing Real Work - Few Companies Have Real Use Cases(21:00) Demo 3: One-on-One Meeting Coach (Most Sophisticated Build)(23:20) Calculating Talk-to-Listen Ratios(24:40) Scaling HR Business Partners - Every Company's Manager Problem(26:07) Implementation Choices: On-Demand vs Required(27:35) Transparency: What Data? Where Stored? Who Sees It?(28:44) The Iron Man Suit vs AI Overlords(28:56) Where to Find Brandon - LinkedIn(29:12) 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

This week we chat with Claire Hughes Johnson!Claire is the former COO of Stripe, where she played a critical role in scaling the company from 160 employees to more than 7,000 during its period of rapid global expansion. Before Stripe, she spent over a decade at Google, leading large international teams across multiple high-growth products and operations.She now serves on the boards of HubSpot, The Atlantic, Aurora, and several other organizations, is an active angel investor, and is the bestselling author of Scaling People, widely regarded as a modern classic on leadership, management, and organizational design.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Claire Hughes Johnson: @chughesjohnson@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

For today's essential Heretics 101 feature, former Meta HR leader Cynthia Bazlamit (Baz) Shrauner talks about demoting herself twice for fulfillment over title. She also describes Facebook's pandemic hiring frenzy that ballooned teams 10x, the subsequent brutal layoffs, and the effect of DEI resource groups on the company.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* 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.KEEP UP WITH BRYAN, NOLAN + KELLI ON LINKEDINBaz: https://www.linkedin.com/in/cynthia-bazlamit-shrauner-683767/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__LINKS:For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:17) Intro(01:06) The First Demotion Story: Getting Demoted at Facebook(05:17) The Second Demotion: Hiring Christine Ellis & Doing It Again(10:00) “Comparison is the Thief of Joy” - The Ego Struggle(11:00) Sponsor: Metaview(12:59) Meta's Pandemic Hiring Spree: “We Were Sloppy”(15:44) The Layoffs: Three Waves of RIFs, 8,000+ Cuts(19:42) DEI & Resource Groups: From Fun to Corporate Chaos(24:00) Closing 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

Boeing reports orders and deliveries for the month of November. The numbers, this hour. Then crypto company ‘Twenty One Capital' makes its NYSE debut after completing a SPAC merger. Founder and CEO Jack Mallers joins the show to break down the outlook. Plus, an exclusive with the CEOs of Fifth Third and Brex after announcing a new commercial partnership. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Welcome back to Trailblazers by Park Rangers Capital!In this week's solo episode, host Erica Wenger breaks down 7 things she wishes every founder knew before raising their first check. The honest, unfiltered truths that can dramatically change the way you approach fundraising.Drawing from the countless lessons she's learned while raising for her own firm, Erica unpacks the realities behind investor conversations, what actually moves a deal forward, and the common mistakes first-time founders don't even realize they're making.From understanding how investors really make decisions to setting expectations, building genuine momentum, and crafting a narrative that sticks, Erica shares the tactical learning nuggets she had to earn the hard way.If you're preparing for your first raise or simply want a clearer look at how fundraising really works behind the scenes. This episode is your grounded, practical guide to entering the capital-raising arena with confidence.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by Rocketreach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo (formerly OpenPhone): Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

Bryan Power, who recently left Nextdoor after seven years, discusses his viral article on quitting properly, why exits define careers, manager failures, and the Growth by Design-Cursor acquisition's implications.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* 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.KEEP UP WITH BRYAN, NOLAN + KELLI ON LINKEDINBryan: https://www.linkedin.com/in/bryanpower/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__LINKS:For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Introduction & Power Hour Returns(00:55) Bryan's Viral “How to Quit” Article(04:00) Why Your Exit Becomes Your Entire Story(06:00) Why Companies Don't Teach Employees How to Leave(09:00) The Loyalty Expectation Problem(12:27) Sponsor: Metaview(14:38) How Managers Screw Up Exits(21:57) No Long Goodbyes: The Best Timing Advice(24:13) What to Do When Someone Resigns(27:30) Maintaining Relationships After You Leave(29:26) Growth by Design Acquired by Cursor(36:33) The State of the Recruiting Market(40:00) AI Native Skills & The Future of Entry Level Hiring(46:49) Cringey Corporate Lingo Game(50:55) 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

#EP322 Today on the Clean Power Hour, we dive into one of the biggest bottlenecks strangling the clean energy transition: the slow, messy world of zoning, permitting, and early-stage development. Our guests are Julia Wu and Anuj Saigal, co-founders of Spark AI, a Y Combinator-backed platform that has ingested and summarized nearly every zoning code, ordinance, and permitting pathway in the United States.Julia Wu is CEO and co-founder of Spark AI. She's a software engineer who cut her teeth at Microsoft, Apple (working on Siri), and Brex before founding Spark. Her background spans AI, natural language processing, and financial technology.Anuj Saigal is the co-founder of Spark AI and a veteran of the energy sector since 2010. He worked at the Department of Energy Loan Programs Office during the Obama administration, then moved through SunEdison, EVgo, and Natto (a video AI telematics company). Anuj has been a developer of utility-scale and distributed generation projects and understands the pain points of permitting and interconnection firsthand.Key Discussion Points:Spark AI uses large language models to aggregate zoning regulations, permitting requirements, local sentiment, and news articles for every jurisdiction in AmericaThree core use cases: early-stage greenfield site selection, monitoring projects in development for regulatory changes, and rapid acquisition due diligenceStandard Solar (Brookfield-owned) reduced acquisition diligence from months to one week, cutting time by 75%Dynamic Energy accelerated site screening while improving community sentiment risk assessmentUGE used Spark to assess a massive portfolio acquisition, determining which parcels had viable zoning pathsThe platform is LLM-neutral, easily swapping between OpenAI, Anthropic, DeepSeek, and other models to optimize for accuracy and speedUnlike off-the-shelf AI tools, Spark delivers consistency, accuracy, and citations developers need for trust-but-verify workflowsConnect with Anuj and Julia Julia Wu: https://www.linkedin.com/in/wu-julia/Anuj Saigal: https://www.linkedin.com/in/anujsaigal/Spark AI Website: https://www.sparkhq.ai/ Support the showConnect with Tim Clean Power Hour Clean Power Hour on YouTubeTim on TwitterTim on LinkedIn Email tim@cleanpowerhour.com Review Clean Power Hour on Apple PodcastsThe Clean Power Hour is produced by the Clean Power Consulting Group and created by Tim Montague. Contact us by email: CleanPowerHour@gmail.com Corporate sponsors who share our mission to speed the energy transition are invited to check out https://www.cleanpowerhour.com/support/The Clean Power Hour is brought to you by CPS America, maker of North America's number one 3-phase string inverter, with over 6GW shipped in the US. With a focus on commercial and utility-scale solar and energy storage, the company partners with customers to provide unparalleled performance and service. The CPS America product lineup includes 3-phase string inverters from 25kW to 275kW, exceptional data communication and controls, and energy storage solutions designed for seamless integration with CPS America systems. Learn more at www.chintpowersystems.com

This week, we chat with Nikhil Basu Trivedi! Nikhil is Co-Founder & General Partner at Footwork, an early-stage focused venture firm in San Francisco. Footwork leads Seed and Series A rounds in companies with early signs of product-market fit, across both consumer technology and the consumerization of enterprise technology.The firm was founded in 2021 and is investing its second fund, with $400M of AUM. Footwork's portfolio companies include Elicit, Felt, GPTZero, Tracksuit, Watershed, and WindBorne. Nikhil was previously a Managing Director at Shasta Ventures, where he led the firm's investments in Athelas, Canva, ClassDojo, Color, Frame.io, Imperfect Foods, Lattice, and The Farmer's Dog. He started his career on the investing team at Insight Partners and on the founding team at Artsy. Nikhil graduated from Princeton University with a degree in molecular biology and finance.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Nikhil Basu Trivedi: x.com/nbt@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

For today's essential Heretics 101 feature, Couchbase CPO Fidelma Butler talks about modern L&D: building contextual leadership frameworks, meeting employees in workflows, activating peer teaching, and addressing career development's promotion fixation.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* 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.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:16) Intro(01:21) Building L&D from Scratch at Couchbase(02:45) Defining Good Leadership: The Three-Way Framework(05:04) Meeting People Where They Are: Escaping Theoretical Land(06:06) When Survey Results Disagree with CEO Priorities(07:35) Embedding L&D in the Fairway of the Job(08:19) Leaders Teaching Leaders: Why It Works(11:36) Coaching for Senior Leaders: Addressing the Intangibles(13:35) Hiring for Modern L&D: New Skills Required(14:25) The Career Development Problem: Everyone Wants It, Nobody Does It(16:30) Why Career Ladders Become Checkbox Exercises(19:01) The Ladders Dilemma and Being Transparent with Employees(20:10) Treating Employees Like Adults(20:59) Outro 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, Joe and Heather talk about major updates from Intuit, including its expansion of TurboTax service locations and the introduction of the new Intuit Account Suite. They also explore deeper themes, from how past experiences shape us, to generational perspectives on AI, to how firms can adapt strategically to a changing profession. Current events — Intuit Accounting Suite launch Intuit opening a total of 600 on premises locations throughout the U.S. TV/Movie quote of the week — How to Train Your Dragon IT chapter 2 Excellent things we learned — These 14 colleges offer bachelor's degrees in AI—including one Ivy League school Notion Member spotlight — Auburndale Bookkeeping The Woodard Report article of the week — Setting Up a Business for Spouses: Steps to Take 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

This week, we chat with Jeffrey Bussgang! Jeff has spent his career at the intersection of startup experimentation and transformative technology. For over a decade, he has taught one of Harvard Business School's most popular entrepreneurship courses, Launching Tech Ventures, where he's helped thousands of founders build and scale successful companies. As co-founder of Flybridge Capital Partners (a leading seed VC fund with over $1 billion under management), he and his partners were early to recognize AI's potential to transform startups, evolving the firm's investment thesis to focus exclusively on AI-forward companies and founders. Before his time as an educator and investor, Bussgang experienced the startup journey firsthand—joining Open Market's early team and helping lead it through an IPO in 1996, and then co-founding Upromise in 2000, which was successfully acquired. This unique vantage point—as professor, investor, and startup executive—has given him an unmatched perspective on how AI is revolutionizing the startup landscape.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Jeff Bussgang@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

For today's essential Heretics 101 feature, former co-founder and executive coach Adam Weber examines power dynamics and identity transformation following Amplify's acquisition by 15Five, revealing insights on leadership evolution and maintaining authentic culture through organizational integration.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* 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.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(01:57) Post-Acquisition Power Dynamics: The Humbling Moment(03:00) HR's Inflection Point: More Responsibility, Same Resources(05:12) Top 5% HR Leaders: Show Courage and Speak the Language of Business(06:59) What ‘Understanding the Business' Really Means(08:15) The Reality Check: HR's Impossible Workload(10:25) Sponsor: Metaview(11:47) The Troubling Trend: AI Up, Leadership Development Down(13:50) The Future of Management: NVIDIA's Model and Investing in ICs(18:18) Ruthless Experimentation and the Death of Best Practices(20:00) Building Credibility: Sharing Both Wins and Losses 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

A tiny Calgary-based exploration company ignites a global market frenzy when it discovers the world's largest gold deposit before collapsing into one of the biggest frauds in mining history. Prelude: The "Bushman of the Shuswap" flees society after uncovering a massive conspiracy. –––-–---------------------------------------- BECOME A VALUEDLISTENER™ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Patreon⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠ –––-–---------------------------------------- DONATE: ⁠⁠⁠⁠⁠⁠⁠⁠⁠SwindledPodcast.com/Support⁠⁠⁠⁠⁠⁠⁠⁠⁠ CONSUME: ⁠⁠⁠⁠⁠⁠⁠⁠⁠SwindledPodcast.com/Shop⁠⁠⁠⁠⁠⁠⁠⁠⁠ –––-–---------------------------------------- MUSIC: ⁠⁠⁠⁠⁠⁠⁠⁠⁠Deformr⁠⁠⁠⁠⁠⁠⁠⁠⁠ –––-–---------------------------------------- FOLLOW: ⁠⁠⁠⁠⁠⁠⁠⁠⁠SwindledPodcast.com⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Twitter.com⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠ Thanks for listening. :-) Learn more about your ad choices. Visit podcastchoices.com/adchoices

Rachel Lockett is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coaching session with me.We discuss:* When to coach and when to just tell people what to do [09:00]* The GROW technique for helping people figure out a solution for themselves [18:37]* Techniques for making difficult conversations less difficult [01:20:28]* Avoiding burnout and designing a more energizing career [41:55]* Building and sustaining a healthy co-founder relationship [01:06:50]* Creating a one-page plan that aligns your entire company [01:31:47]* Practical ways AI is transforming executive coaching and leadership development [01:36:50]* Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions [23:55]Also on Spotify and Apple PodcastsBrought to you by:Stripe—Helping companies of all sizes grow revenueVanta—Automate compliance. Simplify security.Persona—A global leader in digital identity verificationWhere to find Rachel Lockett:• LinkedIn: https://www.linkedin.com/in/rhlockett/• Website: https://www.lockettcoaching.comReferenced:• One-page plan template: https://www.lockettcoaching.com/#resources• Lockett Coaching Leadership Toolkit: https://www.dropbox.com/scl/fi/s74a9cn1ka1ebz6pglypf/Leadership-Toolkit_-Coaching-Rachel-Lockett.pdf?rlkey=yg2m9df2ziwy0fa6p0dt4gcfu&st=dgzvnf76&dl=0• Renew Your Co-Founder Vows—and Other Tactics for Strengthening the Most Important Relationship in Your Startup: https://review.firstround.com/five-practices-to-strengthen-your-co-founder-relationship/• First Round Guide to Co-Founder Check-Ins: https://docs.google.com/document/d/1yUosmfMuE-8-sAwPrEPDcGqkJLVLWg5dC2_8lcXm7U4/edit?tab=t.0• Coinbase: https://www.coinbase.com• Management Time: Who's Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey• Chuck Palahniuk's quote from Fight Club: https://www.goodreads.com/quotes/1338270-people-don-t-listen-they-just-wait-for-their-turn-to• Patrick Collison on X: https://x.com/patrickc• Stripe: https://stripe.com• Remind: https://www.remind.com• Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams• Brex: https://www.brex.com• Bridge: https://www.bridge.xyz• Superhuman's secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building• The Enneagram Institute: https://www.enneagraminstitute.com• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin• How have I been complicit in creating the conditions I say I don't want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence• What Is PeopleFirst?: https://alpineinvestors.com/story/what-is-peoplefirst• How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor, founder of Alpine Investors): https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver• Granola: https://www.granola.ai• KPop Demon Hunters on Netflix: https://www.netflix.com/title/81498621• Loom: https://www.loom.com• Joseph Campbell's quote: https://www.goodreads.com/quotes/21396-if-you-can-see-your-path-laid-out-in-front• Wes Anderson's short films (Roald Dahl) on Netflix: https://www.netflix.com/tudum/articles/wes-anderson-netflix-short-filmsRecommended books:• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904• Designing Your Life: How to Build a Well-Lived, Joyful Life: https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321• Roald Dahl books: https://www.amazon.com/Roald-Dahl-Collection-Books-Box/dp/0241377293Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.Lenny may be an investor in the companies discussed.My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Welcome back to Trailblazers by Park Rangers Capital!In this week's solo episode, host Erica Wenger dives into Starting a VC Fund 101, breaking down the real reasons why you might want to start a fund, what it actually takes to launch one, and the lessons she's learned from being in the trenches herself.From structuring your first fund to navigating LP conversations and finding your unique edge, Erica shares insider tips and hard-earned insights that every aspiring fund manager should hear.If you've ever thought about building your own VC fund or just want to understand how the process really works behind closed doors, this episode is your practical and honest guide to getting started in venture capital.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by Rocketreach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo (formerly OpenPhone): Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

For today's essential Heretics 101 feature, Disruptive HR founder Lucy Adams dissects HR's fundamental trust problem: why designing policies around your worst employees destroys organizational performance, and how to reimagine the business partner role.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* 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.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(04:15) HR's Fundamental Trust Problem & Designing for the Minority(08:30) Sponsor: Metaview(09:00) The Opportunity Cost of Distrust(12:00) The HRBP Role: Why It's Broken & How to Fix It(15:30) What HR Leaders Are Talking About: DEI, AI & Merit(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

Ankur is a serial entrepreneur, investor, and the founder of Carry, a modern platform helping business owners build durable wealth through smarter tax strategies and long-term financial systems.He's also the founder of Vibe Capital, a $100M venture fund backing bold founders across the U.S., India, and beyond, and the creator of Silly Money, a fast-growing newsletter and community helping people beat the game of capitalism.Before that, Ankur founded Teachable, the groundbreaking platform that empowered over 100,000 creators to turn their expertise into income—helping them earn over $1 billion and scaling Teachable to $60M in ARR before its nine-figure exit to Hotmart.Ankur is passionate about helping founders and entrepreneurs not just make money, but keep it, through the right systems, strategy, and mindset for long-term freedom.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Ankur Nagpal: @ankurnagpalsillymoney.com@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

On today's Dear Heretics segment, Nolan and Kelli debate equity compensation philosophy: whether companies should extend stock options to all employees or reserve them for senior roles, weighing moral imperatives against investor dilution concerns and implementation complexity.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* 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.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(01:07) Question about stock options for all employees(01:48) Carta's philosophy on making everyone an owner(03:32) Moral case for giving equity to everyone(05:07) Story about Carta's employee refresh and Fred Wilson(06:21) Challenge of educating employees on equity(08:28) Pendo's approach to equity education and round tables(09:19) Setting expectations with $0 default value(10:08) Sponsor - Metaview(11:29) Cost of labor adjustments for equity across locations(13:00) Administrative challenges of geo-based equity adjustments(14:16) Employee communication and comparison issues(16:10) Board tension over equity dilution decisions(17:28) Attracting great talent requires competitive compensation(18:06) Moral case and taxes of giving equity(19:00) Importance of working with equity experts(19:46) Closing thoughts on geo strategy and communication(21:34) 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

Master Your Cashflow (Templates Included): https://startup-ideas-pod.link/money-map On this episode, I share my simple financial operating system that helps me run my business. I share actual workflows that have saved one of my portfolio company from an 11-week runway crisis (when they thought they had 8 months), and the templates behind his 13-week cash tracker, Bear/Base/Bull decision framework, and one-page board report. This is a rare look inside the tactics I use to think about cash flow, dilution strategy, and building companies that don't run out of runway by accident. Bank with Brex: https://startup-ideas-pod.link/brex-sip Timestamps 00:00 – Intro: The whiteboard that saved two companies 02:08 – The Financial Rhythm: Daily, weekly, monthly cadence 03:23 – Rule 1: The 13-Week Cash Flow System 06:10 – Rule 2: Cash vs. Accrual 08:14 – Rule 3: Extend Runway 12:13 – Rule 4: Be Exit Ready 15:06 – Rule 5: Cards and Credit 18:01 – Rule 6: Track 5 Weekly Metrics 20:00 – Rule 7: The Monthly One-Pager 21:12 – Rule 8: Tools and Automation 26:11 – Rule 9: Dilution Mindset 27:59 – How to implement: The weekly rhythm in practice 29:31 – Action plan and closing Key Points Your P&L lies about survival—one portfolio company thought they had 8 months of runway but actually had 11 weeks when mapped to real cash flow The Bear/Base/Bull decision framework prevents emotional spending: if two-plus scenarios say no, wait (a $60K conference booth was rejected in bear case, approved two months later in bull case) Acquisitions happen in 48 hours—keep a 10-file data room updated quarterly so you can respond to Tuesday emails with Wednesday meetings Trust doesn't scale, policy does: weekly corporate card reviews caught an $8K personal ad spend in 7 days instead of 30 The system runs itself once built: 15 minutes Monday + 30 minutes Friday + 4 hours/month replaces heroic monthly scrambles Every dollar raised costs ownership forever—cutting $40K/month burn has the same 12-month runway impact as fundraising but with 0% dilution The #1 tool to find startup ideas/trends - https://www.ideabrowser.com LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/ Boringmarketing - Vibe Marketing for Companies: boringmarketing.com The Vibe Marketer - Join the Community and Learn: thevibemarketer.com Startup Empire - get your free builders toolkit to build cashflowing business - https://startup-ideas-pod.link/startup-empire-toolkit Become a member - https://startup-ideas-pod.link/startup-empire FIND ME ON SOCIAL X/Twitter: https://twitter.com/gregisenberg Instagram: https://instagram.com/gregisenberg/ LinkedIn: https://www.linkedin.com/in/gisenberg/