Podcasts about Rippling

Ever wonder why some COOs scale businesses to legendary heights while others get swallowed by chaos and politics? If you're craving clarity, confidence, and uncommon edge in your second-in-command role, this Fan Favorite episode is your wake-up call. Cameron Herold sits down with Matt MacInnis, COO of Rippling and co-founder of Inkling, for a raw, actionable conversation about the real challenges behind hyper-growth, hiring, trust, and culture. They dig into what makes the COO role so “special,” how to build a game-changing flywheel, and why patience, precision, and authenticity are the ultimate power moves.The pain of “going it alone” is real. Tune in to learn how to avoid disaster, dodge politics, and harness proven tactics you won't find in any business book. Don't wait until burnout bites. Listen now for fiercely exclusive COO insights, bold truths, and systems that will let you scale smarter, not harder.Timestamped Highlights[00:02:22] – The hidden pain in HR, IT, and how Rippling breaks the “original sin” of bad data[00:05:55] – Why Matt almost walked away—then got schooled by Parker's contrarian “rocket ship” logic[00:08:30] – The untold power of preexisting trust between CEO and COO—and what happens if you hire without it[00:12:49] – Topgrading secrets: Why most executive hiring fails and how to get it right (even when everyone says they're an “A player”)[00:15:44] – Copilot dynamics: How Matt and Parker run the company with surprisingly little contact (and why it works)[00:19:18] – Should you debate the CEO in front of the team? The cathartic, risky art of public disagreement[00:23:13] – Inside Rippling's flywheel advantage—what Salesforce, Facebook, and Brex did differently and why you can too[00:31:04] – Killing bureaucracy and politics: The simple rule for hiring and process that most leaders ignore[00:39:29] – The brutal, proven formula for layoffs: What Sequoia teaches (and how to survive the “survivor's guilt”)About the GuestMatt MacInnis is the Chief Operating Officer of Rippling, a revolutionary all-in-one HR and IT platform transforming how businesses scale and manage people. Matt was also the co-founder and CEO of Inkling, a mobile learning platform that raised over $100M before its acquisition. With deep roots at Apple and a Harvard engineering degree, Matt blends big-company brilliance with entrepreneurial firepower. He's known for breaking boring business norms and igniting hyper-growth, all while refusing to tolerate politics, inefficiency, or shallow executive hiring.

#330 | Dave is joined by Ryan Narod, VP of Marketing at Rippling, to break down how Rippling has built one of the stand outbrands in B2B right now. Ryan walks through real examples of campaigns they've run over the last year, from scrappy iPhone videos and webinar promos to high-production customer stories and their 2026 Super Bowl commercial. They talk about how Rippling shifted from being great at growth marketing to building a brand people actually recognize, how they inject more personality and “human” into everything they ship, and how they measure brand marketing without losing pipeline accountability. To see Ryan's real campaign examples, head over to youtube.com/@heydavegerhardt.Timestamps(00:00) - - Why Rippling is going all-in on brand (02:51) - - Ryan's background and why he joined Rippling (04:14) - - What Rippling does and how they position the platform (08:14) - - What “brand marketing” means at Rippling (10:34) - - Building a story that makes HR the hero (19:47) - - Ryan shares Rippling marketing examples (ads, videos, webinars) (27:17) - - High-production customer storytelling (Berries) (32:39) - - The “HR Deserves Better” campaign (35:37) - - How Rippling measures brand and pipeline impact (43:14) - - The Super Bowl commercial and what it takes to pull it off (45:17) - - Final takeaways and wrap-up Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.  ***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used. In today's episode, we discuss: Why design leaders who stop designing stop leading The four pillars every design manager must master How to delegate when you're a perfectionist Why leaders need strong opinions How to scale good judgment What Rippling's operating system teaches about speed and commitments References: Airbnb: https://www.airbnb.com/ Amazon: https://www.amazon.com/ Apple: https://www.apple.com/ Asana: https://www.asana.com/ Brian Chesky: https://www.linkedin.com/in/brianchesky/ CrossFit: https://www.crossfit.com/ Figma: https://www.figma.com/ Honeywell: https://www.honeywell.com/ Liz Sanders: https://www.linkedin.com/in/sandersliz/ Nest: https://store.google.com/category/google_nest Notion: https://www.notion.so/ Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Rippling: https://www.rippling.com/ Stripe: https://www.stripe.com/ Where to find Ryan: LinkedIn: https://www.linkedin.com/in/ryanwlucas/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Intro 00:08 What design actually does at a software company 01:40 The roots of design: from industrial design to software 03:29 Useful, usable, desirable — and used 04:49 How design relates to engineering, product, and marketing 08:15 Measuring success as a design leader 12:40 The gap between director and VP-level design leadership 14:23 Why great design leaders jump up and down in altitude 19:26 The four pillars every design manager must master 21:34 Over-indexing on quality and the perfectionist trap 25:11 When lowering the quality bar actually cost the business 27:53 How to build judgment through pattern matching 31:25 How Ryan's design team differs from the rest 34:31 Why Figma is not the source of truth 36:32 How Ryan spends his week: recruiting, crits, and staff meetings 38:39 The "Do/Try/Consider" framework 42:12 The most important decisions of the past year 44:05 Should one-on-ones exist? 46:45 How to scale judgment 50:49 What to look for when hiring your first design leader 54:54 Advice for young designers who want to lead 58:24 Demanding yet supportive: A balanced management style 01:02:43 What Rippling's operating system teaches about execution

Keith Rabois joins the Newcomer Podcast for a wide-ranging conversation that moves between tech, venture capital, and politics.On the tech side, we start with Brex being acquired by Capital One and what that means for Ramp. Rabois argues that banks won't build the “finance organization of the 21st century,” and frames Ramp's ambition as building the CFO's “eyes, ears, and actions” across a company. We also discuss Rippling's strategy, investor responsibilities around integrity and ethics, and how he thinks about “barrels and ammunition” when companies try to do many things at once.From there we get into AI investing and Rabois's view that what matters is the end-customer value proposition and the durability of the advantage. He explains Rogo as an AI “copilot” for investment bankers and talks about workflow and data moats.The episode also turns heavily to politics and current events: Trump, tech's relationship with the administration, immigration (including H-1B and O-1 visas), free speech, and foreign policy debates (including China, Europe, and the Middle East). We also argue through a recent incident involving law enforcement and protest/obstruction, and close with Opendoor—where Rabois lays out his view of the company's turnaround, retail investors, and the company's weekly “accountability” metrics updates.

Plus Texas actor James Van Der Beek has died at the age of 48, hundreds of dogs have been rescued from a Dallas animal fighting operation, the city of Dallas' representation on the DART Board of Directors can soon change after a newly passed resolution, and more!

Keith Rabois joins the Newcomer Podcast for a wide-ranging conversation that moves between tech, venture capital, and politics.On the tech side, we start with Brex being acquired by Capital One and what that means for Ramp. Rabois argues that banks won't build the “finance organization of the 21st century,” and frames Ramp's ambition as building the CFO's “eyes, ears, and actions” across a company. We also discuss Rippling's strategy, investor responsibilities around integrity and ethics, and how he thinks about “barrels and ammunition” when companies try to do many things at once.From there we get into AI investing and Rabois's view that what matters is the end-customer value proposition and the durability of the advantage. He explains Rogo as an AI “copilot” for investment bankers and talks about workflow and data moats.The episode also turns heavily to politics and current events: Trump, tech's relationship with the administration, immigration (including H-1B and O-1 visas), free speech, and foreign policy debates (including China, Europe, and the Middle East). We also argue through a recent incident involving law enforcement and protest/obstruction, and close with Opendoor—where Rabois lays out his view of the company's turnaround, retail investors, and the company's weekly “accountability” metrics updates.

Maxima is building AI agents that automate enterprise accounting while maintaining the auditability and control standards finance teams require. In a recent episode of BUILDERS, we sat down with Yogi Goel, CEO and Co-Founder of Maxima, to explore his eight-year journey at Rubrik from Series C through IPO, and how those lessons shaped his approach to solving the 70-80% of finance time currently wasted on manual work. Topics Discussed: Why Rubrik's approach—entering stagnant markets with first-principles thinking—became Maxima's blueprint Securing $3K-$5K POC commitments from Figma mockups before writing code Why Scale AI and Rippling rejected a point solution and demanded 3-4 modules from day one The compound startup model: building multiple products simultaneously to meet buyer expectations How 17% of CFOs are adopting AI tools today (vs 51% in software development) Why finance teams view AI agents as "digital college freshmen" who need proof of work Hiring from YouTube Studios, Apple, and Robinhood instead of legacy finance software companies How NetSuite World conference booth sizes revealed the data integration infrastructure gap The $3K-$5K validation threshold that proved finance pain was urgent enough to pay pre-product GTM Lessons For B2B Founders: Demand generation unlocks engineering potential: Yogi learned from his Rubrik mentors: "focus on demand and if you have great engineers then they will solve the problems." Maxima built products in 2-3 months they didn't initially know were technically feasible—because customer demand pulled the engineering team forward. For founders with strong technical teams, customer demand should drive the roadmap, not engineering's comfort zone. Trust your engineers to solve hard problems when customers are waiting. $3K-$5K is the pre-product validation threshold: Before writing any code, Yogi secured POC commitments at this price point based solely on Figma mockups. This isn't about revenue—it's about proving urgency. Verbal interest means nothing. Small pilot commitments mean "we'll try it someday." But $3K-$5K pre-product means "this problem is urgent enough to pay before seeing a working solution." Use this threshold to separate real pain from polite interest. Sophisticated buyers will reject your narrow MVP: Scale AI and Rippling told Maxima explicitly: "If you will only build this one thing, we will not buy. You have to commit to building three, four modules." Conventional wisdom says start narrow, but enterprise buyers with complex workflows won't adopt point solutions that create new integration headaches. When sophisticated buyers articulate their real buying criteria, ignore the startup playbook. Yogi built a "compound startup" with 4-5 modules from day one because that's what the market demanded. Target acute pain over easy access: Early-stage companies (10-30 people) were easier to reach but finance wasn't urgent enough. At that scale, it's "build product, ship product"—finance operations aren't broken enough to warrant urgent attention. Companies at 500-1,000+ employees have finance teams drowning in manual work that prevents strategic contribution. Target where pain justifies urgent action and budget exists, not where calendar access is easiest. Hire intensity and first-principles thinking over domain knowledge: Maxima deliberately hired zero engineers from legacy finance software companies. Their frontend engineer came from YouTube Studios. Others came from Apple, Robinhood, Netflix—none with financial product experience. Yogi's three hiring criteria: "incredible intensity, huge confidence in themselves, and fast thinking mode." Domain expertise creates pattern-matching to old solutions. First-principles thinking creates breakthrough products. One team member didn't finish high school but is "one of the best out there." Make AI explainable or finance teams won't adopt: Finance teams adopted faster than expected because Maxima showed every calculation step. "If they can prove by looking at the Math, you know, 18 plus 88 plus 36 is X. And I can see the step of the work, they are willing to give it to them." This isn't about fancy UX—it's about auditor-grade proof of work. Finance professionals won't trust black box outputs. Build transparency into the product architecture, not as an afterthought. This explainability became Maxima's competitive moat. Conference booth sizes reveal infrastructure gaps: At NetSuite World, the largest booths weren't ERP vendors or payment processors—they were data integration companies. This single observation validated that enterprises are desperately solving data fragmentation problems. Companies manually download from Stripe, Snowflake, Salesforce weekly to build Excel pivots. Maxima invested in upstream integrations as core infrastructure from day one. Use industry conferences to validate where companies are spending money on workarounds—that's where infrastructure gaps exist. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM

Matt MacInnis spent 6 years as COO at Rippling and now leads as CPO. He joined Rippling in 2019, when there were only 70 people, and has led the company across multiple stages.Before that, Matt was a founder for 9 years, building Inkling after 7 years at Apple. These three chapters of his career shape this conversation. We focus on how to build and operate teams as a company scales. Matt explains how he thinks about speed versus real progress, and which parts of building a company should move fast and which should move slowly. He shares how he decided when to introduce processes at Rippling, when to keep things informal, and how to recognize when a process that once helped the company had started to slow it down.We discuss how his role changed as Rippling grew from around 70 people to 100, then to 500, and now to thousands. He explains what he paid attention to at each stage and which metrics he deliberately did not obsess over.These are practical lessons for founders, from the earliest days of a startup to the challenges of scaling a large organization.0:00 - Trailer01:11 – One thing people get wrong about building a business?04:01 – Great founders find markets that already exist06:36 – What does a “death march” mean at Apple?10:11 – How to build a good team in early-stage startup?12:33 – Learnings from Apple to Inkling18:11 – Processes to set up in startups25:20 – Humans always optimize for comfort (and why that's bad instinct)33:09 – Why success teaches you more than failure36:01 – How should processes change as company scales?42:11 – How is AI changing the software industry?54:03 – If Matt were starting up today, how would he do it?57:07 – How would Next-gen PM roles look like?01:01:51 – Matt shares about Rippling CEO Parker01:04:32 – Founder instinct vs Data01:06:06 – Over-optimizing for employee comfort01:07:27 – If building a startup feels comfortable, it's probably dead01:08:36 – One thing only CEO's should do forever01:11:15 – One piece of startup advice Matt doesn't trust-------------India's talent has built the world's tech—now it's time to lead it.This mission goes beyond startups. It's about shifting the center of gravity in global tech to include the brilliance rising from India.What is Neon Fund?We invest in seed and early-stage founders from India and the diaspora building world-class Enterprise AI companies. We bring capital, conviction, and a community that's done it before.Subscribe for real founder stories, investor perspectives, economist breakdowns, and a behind-the-scenes look at how we're doing it all at Neon.-------------Check us out on:Website: https://neon.fund/Instagram: https://www.instagram.com/theneonshoww/LinkedIn: https://www.linkedin.com/company/beneon/Twitter: https://x.com/TheNeonShowwConnect with Siddhartha on:LinkedIn: https://www.linkedin.com/in/siddharthaahluwalia/Twitter: https://x.com/siddharthaa7-------------This video is for informational purposes only. The views expressed are those of the individuals quoted and do not constitute professional advice.Send us a text

Get ready for a high-octane episode, as Joel Cheesman and Emi Beredugo take the mic to dissect everything from "bougie" McDonald's Valentine's stunts to the high-stakes world of Big Tech. The duo dives deep into Rippling's bold Super Bowl debut featuring Tim Robinson, debating whether the "evil genius" move is a brilliant recruitment play or a calculated nod to Wall Street. While Microsoft celebrates a massive LinkedIn revenue milestone—proving the platform has officially pivoted from a resume database to a short-form video powerhouse—the hosts shift gears to the grittier side of the job hunt. From the rise of "Resume Botox" and ageism to the "resume slop" currently clogging AI-driven hiring funnels, the gloves come off. Plus, don't miss the heated critique of ZipRecruiter's new "Be Seen First" feature, which Emi and Joel argue might be doing more harm than good for the modern candidate. Chapters 00:00 - Introduction and Super Bowl Excitement 05:04 - The Beckham Family Drama 08:58 - Valentine's Day Fast Food Promotions 14:09 - Rippling's Super Bowl Ad 22:01 - LinkedIn's Revenue Growth and Strategy 27:57 - The Rise of Resume Botox and Ageism in Job Market 30:58 - The Age Discrimination Dilemma 35:59 - AI's Impact on Hiring Practices 45:00 - The Clumsy Evolution of Recruitment 56:04 - ZipRecruiter's Controversial New Feature

The Shred is a weekly roundup of what's making headlines in the world of employment. The Shred is brought to you today by Jobcase.

In this episode, Jason Bay sits down with Rippling's VP of Sales Enablement, Jonas Master to explore how effective sales training, paired with clear priorities, measurement, and reinforcement, drives real behavior change and consistent performance gains. Check out more free content and get coaching at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

Today on the Newcomer Podcast, we're at MongoDB.Local for a series of conversations on how enterprise AI is actually being built.MongoDB CEO CJ Desai joins the show 65 days into the role to explain why San Francisco is “back,” how MongoDB is repositioning itself for the AI era, and why unstructured data has made the company's platform a natural foundation for AI-native applications. He shares his view on the AI hype cycle, the rapid rise of companies like OpenAI and Anthropic, and why MongoDB is staying model-agnostic as AI product cycles accelerate.We also sit down with Rippling's Head of AI Ankur Bhatt to discuss how AI is being deployed inside a live enterprise system. The conversation covers building agents across payroll, IT, and finance, why agent identity and accountability matter, and how Rippling is approaching permissions, access control, and AI-driven productivity at scale.A grounded look at the enterprise AI stack, from the data layer to real-world deployment.MongoDB #Rippling #AIAgents #VentureCapital

Today on the Newcomer Podcast, we're at MongoDB.Local for a series of conversations on how enterprise AI is actually being built.MongoDB CEO CJ Desai joins the show 65 days into the role to explain why San Francisco is “back,” how MongoDB is repositioning itself for the AI era, and why unstructured data has made the company's platform a natural foundation for AI-native applications. He shares his view on the AI hype cycle, the rapid rise of companies like OpenAI and Anthropic, and why MongoDB is staying model-agnostic as AI product cycles accelerate.We also sit down with Rippling's Head of AI Ankur Bhatt to discuss how AI is being deployed inside a live enterprise system. The conversation covers building agents across payroll, IT, and finance, why agent identity and accountability matter, and how Rippling is approaching permissions, access control, and AI-driven productivity at scale.A grounded look at the enterprise AI stack, from the data layer to real-world deployment.MongoDB #Rippling #AIAgents #VentureCapital

In this episode, Carlos Gonzalez de Villaumbrosia, CEO & Founder at Product School, interviews Anique Drumright, General Manager and VP of Product at Rippling, the workforce management platform valued at $16.8 billion with over $570 million in ARR.Anique is a product veteran who has shaped high-growth teams at Uber, TripActions, and Loom. Now at Rippling, she helps lead a workforce of over 4,000 employees, including 100 former founders, to maintain the speed and ownership typically lost at scale. In this conversation, Anique breaks down how Rippling successfully operates as a compound startup and why product leaders must evolve into General Managers.What you'll learn:How to pivot from managing a backlog to owning a P&L as a GM.The Compound Startup framework for consolidating enterprise categories.How to build high-performing teams by hiring for "founder-level" curiosity.Strategies for proving ROI to enterprise customers to drive platform adoption.Key takeaways:Go and See: Why leaders must personally investigate customer issues to set the bar for quality.Singular Obsession: How to organize teams to maintain focus and velocity as you scale.Automating ROI: How Rippling uses product efficiency to justify headcount reduction for clients.Credits:Host: Carlos Gonzalez de VillaumbrosiaGuest: Anique DrumrightSocial Links: Follow our Podcast on Tik Tok here Follow Product School on LinkedIn here Join Product School's free events here Find out more about Product School here

THIS is how you keep your infrastructure costs from spiraling out of control. Today, we're talking to Albert Strasheim, CTO at Rippling. We discuss the cost crisis facing CTOs in the age of AI, how he reduced infrastructure costs by 30% while growing traffic by 25%, and why holding back feedback is actually the most selfish thing a leader can do. All of this right here, right now, on the Modern CTO Podcast!  To learn more about Rippling, check out their website here.

Lenny's Podcast: Product | Growth | Career ✓ Claim : Read the notes at at podcastnotes.org. Don't forget to subscribe for free to our newsletter, the top 10 ideas of the week, every Monday --------- Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you've gone too far3. Matt's transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—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 Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion's success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling's vision and success(01:17:48) AI's impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman's website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I'm Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—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

Lenny's Podcast: Product | Growth | Career ✓ Claim Key Takeaways Deliberately understaff projects: Constraints force creativity and prevent bloat from politics and bureaucracyYou've gone too far when teams can't ship basic functionalityThe sweet spot is uncomfortable but productive tensionGood teams get tired; great teams run in the red constantly and destroy good teams in that momentHigh alpha, low beta framework: Evaluate people and processes on upside potential (alpha) versus volatility (beta)Prioritize high alpha opportunities even with higher betaProcesses exist solely to lower beta but suppress alpha as a trade-offThe nuanced dance is decreasing volatility where needed (like payroll) without killing upside in innovation areasKnow when to quit your startup: If you're not certain you have product-market fit, you don't have itCompanies that hit big do so quickly; the “never quit” mentality is VC propaganda designed to extract value from founders, not protect themPivot twice or three times maximum, typically by year fourYou're running an experiment to see if the universe has binding receptors for your product. If not, move on… Leadership means fighting entropy relentlesslyTeams naturally optimize for local comfort and disorderExecutives must demand 99% energy levels daily, or the system decaysTop performers don't get 10% more rewards; they get 10-100xBeing “chill” accomplishes nothingWithholding negative feedback is selfish because you prioritize your comfort over making teammates and the company better Read the full notes @ podcastnotes.orgMatt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you've gone too far3. Matt's transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—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 Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion's success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling's vision and success(01:17:48) AI's impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman's website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I'm Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—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

Lenny's Podcast: Product | Growth | Career ✓ Claim Key Takeaways Deliberately understaff projects: Constraints force creativity and prevent bloat from politics and bureaucracyYou've gone too far when teams can't ship basic functionalityThe sweet spot is uncomfortable but productive tensionGood teams get tired; great teams run in the red constantly and destroy good teams in that momentHigh alpha, low beta framework: Evaluate people and processes on upside potential (alpha) versus volatility (beta)Prioritize high alpha opportunities even with higher betaProcesses exist solely to lower beta but suppress alpha as a trade-offThe nuanced dance is decreasing volatility where needed (like payroll) without killing upside in innovation areasKnow when to quit your startup: If you're not certain you have product-market fit, you don't have itCompanies that hit big do so quickly; the “never quit” mentality is VC propaganda designed to extract value from founders, not protect themPivot twice or three times maximum, typically by year fourYou're running an experiment to see if the universe has binding receptors for your product. If not, move on… Leadership means fighting entropy relentlesslyTeams naturally optimize for local comfort and disorderExecutives must demand 99% energy levels daily, or the system decaysTop performers don't get 10% more rewards; they get 10-100xBeing “chill” accomplishes nothingWithholding negative feedback is selfish because you prioritize your comfort over making teammates and the company better Read the full notes @ podcastnotes.orgMatt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you've gone too far3. Matt's transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—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 Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion's success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling's vision and success(01:17:48) AI's impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman's website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I'm Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—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

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The Legion of Doom (LoD) wasn't just a “hacker group”, it captured the essence of underground hacking in the 80s/90s. BBSes, phreaking, rival crews, and the crackdowns that changed everything. From those humble beginnings came a legacy that still echoes through modern security culture today.SponsorsSupport for this show comes from ThreatLocker®. ThreatLocker® is a Zero Trust Endpoint Protection Platform that strengthens your infrastructure from the ground up. With ThreatLocker® Allowlisting and Ringfencing™, you gain a more secure approach to blocking exploits of known and unknown vulnerabilities. ThreatLocker® provides Zero Trust control at the kernel level that enables you to allow everything you need and block everything else, including ransomware! Learn more at www.threatlocker.com.This show is sponsored by Rippling. Rippling is the unified platform for Global HR, Payroll, IT, and Finance. They've helped millions replace their mess of cobbled-together tools with one system designed to give leaders clarity, speed, and control. With Rippling, you can run your entire HR, IT, and Finance operations as one, or pick and choose the products that best fill the gaps in your software stack. Learn more rippling.com/darknet.This show is sponsored by Meter, the company building networks from the ground up. Meter delivers a complete networking stack - wired, wireless, and cellular - in one solution that's built for performance and scale. Meter's full-stack solution covers everything from first site survey to ongoing support, giving you a single partner for all your connectivity needs. Go to meter.com/darknet to book a demo now!Sources Book: Masters of Deception (https://amzn.to/4q3O0gJ) Book: The Hacker Crackdown (https://amzn.to/3N4bovY)

At the end of Michael's first Wavemaker Conversation with psychiatrist Irvin Yalom, in 2015, Michael extracted a promise: that Dr. Yalom would join him for another conversation after Yalom completed his memoir. Two years later, Dr. Yalom released his memoir, and kept his promise.Irvin Yalom is a highly esteemed psychoanalyst, with a large, devoted following; a Professor Emeritus at Stanford University; and a best-selling author. Among his most influential books is “Staring At The Sun: Overcoming the Terror of Death.”Michael is bringing this conversation with Dr. Yalom and the previous one (entitled 50,000 Hours Of Therapy) out of the Wavemaker archives because he hopes and believes that they will provide fuel for a fulfilling 2026.https://wavemaker.me

At the end of Michael's first Wavemaker Conversation with psychiatrist Irvin Yalom, in 2015, Michael extracted a promise: that Dr. Yalom would join him for another conversation after Yalom completed his memoir. Two years later, Dr. Yalom released his memoir, and kept his promise.Irvin Yalom is a highly esteemed psychoanalyst, with a large, devoted following; a Professor Emeritus at Stanford University; and a best-selling author. Among his most influential books is “Staring At The Sun: Overcoming the Terror of Death.”Michael is bringing this conversation with Dr. Yalom and the previous one (entitled 50,000 Hours Of Therapy) out of the Wavemaker archives because he hopes and believes that they will provide fuel for a fulfilling 2026.https://wavemaker.me

Your brand isn't losing to competitors, it's getting flattened by “good enough.”In a world where AI can generate passable B2B content in seconds, bland isn't safe. It's fatal.In this episode, Dan Schwer of Rippling breaks down what brand actually looks like inside a 6.000-person SaaS company with a creative team of 15. We go straight at the uncomfortable stuff: why “brand vs. demand” is a lazy (and expensive) debate, how a brand refresh becomes a business lever (not a design hobby), and what it takes to keep quality high when the org is moving at startup speed and the pipeline still wants receipts.If you're still treating brand as the “pretty layer” on top of performance, this one's going to sting — in a useful way.We also cover:Brand ROI without the fantasy math: Measuring impact through speed, scale, and craft.The “brand vs. demand” trap: Why the fight is fake — and what actually drives pipeline.Video as the new moat: Product launches, customer stories, and earning attention in B2B.AI won't fix bad taste: Where AI helps, where it slows you down, and why judgment still wins.

2025 didn't just shake HR and recruiting. Nope, it yanked the curtain back and lit the place on fire. This year-in-review isn't about press releases and keynote fluff. It's about what really went down when the doors were closed: job boards locking down your hiring data like it's nuclear codes, HR tech rivals apparently confusing “competition” with espionage, private equity strip-mining legacy platforms,and founders playing 4D chess while employees got stuck paying the entry fee. From Indeed trying to own the entire hiring pipeline, to the Rippling vs. Deel spy thriller nobody asked for, to Monster France shutting its doors while exec bonuses stayed warm, to Job.com's bankruptcy unfolding like reality TV — none of this is theoretical. It all happened. Add AI agents ghosting resumes, Slack messages turning into courtroom exhibits, LinkedIn becoming a credibility minefield, and recruiters caught in the blast radius wondering how the hell this became their job. Welcome to 2025's Wrap-Up Show. HR's messiest season yet.

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

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.We discuss:1. Why “extraordinary results demand extraordinary efforts”2. Why you should deliberately understaff projects, and how to know when you've gone too far3. Matt's transition from COO to CPO and what surprised him about leading product4. The “high alpha, low beta” framework for evaluating people, processes, and products5. When founders should quit their startups (hint: much earlier than VCs want you to)6. How to fight entropy in your organization through relentless energy and intensity—Brought to you by:Google Gemini—Your everyday AI assistant: https://ai.dev/Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyGoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation—Where to find Matt MacInnis:• X: https://x.com/stanine• LinkedIn: https://www.linkedin.com/in/macinnis• Email: macinnis@rippling.com—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 Matt MacInnis and Rippling(04:38) The importance of extraordinary efforts(08:37) The challenges and rewards of relentless effort(10:11) Your job as a leader is to preserve intensity(12:39) You learn far more from success than failure(16:34) Transitioning to chief product officer(19:54) Fixing product management at Rippling(25:27) The “high alpha, low beta” framework(28:55) The PQL framework(35:16) Hiring frameworks and team dynamics(36:52) A helpful interview tactic(40:00) Leading as a COO vs. a CPO(42:34) The reality of product-market fit(46:38) The problem with venture capital(49:29) When founders should quit their startups(41:48) The immutable market(54:13) Lessons from Notion's success(57:43) Investment strategies and narrative violations(01:00:42) The power of compounding, power law, and entropy(01:07:02) Maintaining intensity and fighting entropy(01:11:33) The importance of feedback and escalations(01:14:31) Rippling's vision and success(01:17:48) AI's impact on SaaS and business software(01:23:42) AI corner(01:26:23) Final thoughts and lightning round—Referenced:• Rippling: https://www.rippling.com• Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman• Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill• Carvana: https://www.carvana.com• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad• Inkling: https://www.inkling.com• Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari• Notion: https://www.notion.com• Conway's law: https://en.wikipedia.org/wiki/Conway%27s_law• Seeking Alpha: https://seekingalpha.com• Dennis Rodman's website: https://dennisrodman.com• Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle• Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick• SPOTAK: The Six Traits I Look for When I'm Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html• Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1• Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits• New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling• Workday: https://www.workday.com• Matic robots: https://maticrobots.com• Wall-E: https://www.imdb.com/title/tt0910970• Conviction: https://www.conviction.com• Mike Vernal on X: https://x.com/mvernal• Sarah Guo on X: https://x.com/saranormous• No Priors: https://linktr.ee/nopriors• Gemini: https://gemini.google.com• ChatGPT: https://chatgpt.com• Claude: https://claude.ai• Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier• Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c• Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker—Recommended books:• Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557• The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459—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

A modern sales enablement strategy isn't about more activity - it's about better preparation. In this episode of B2B Sales Trends, we explore why preparation has become the true differentiator in B2B selling and enterprise sales strategy. In this conversation, host Harry Kendlbacher sits down with Gena Dakos, a seasoned sales enablement leader, to unpack how high-quality outreach, customer empathy, and thoughtful preparation help sellers stand out in a noisy, AI-driven market. From executive discovery to enterprise-scale deals, this episode reframes enablement as confidence, clarity, and credibility - not just training.

Welcome to the podcast, Rippling IT, who are working on a novel solution for full lifecycle management related to the devices that their platform enables. Hosts: Tom Bridge - @tbridge@theinternet.social Selina Ali - LinkedIn Guests: Zaafir Kherani - LinkedIn Sponsors: Iru 1Password Backblaze Meter Watchman Monitoring If you're interested in sponsoring the Mac Admins Podcast, please email podcast@macadmins.org for more information. Get the latest about the Mac Admins Podcast, follow us on Twitter! We're @MacAdmPodcast! The Mac Admins Podcast has launched a Patreon Campaign! Our named patrons this month include Weldon Dodd, Damien Barrett, Justin Holt, Chad Swarthout, William Smith, Stephen Weinstein, Seb Nash, Dan McLaughlin, Joe Sfarra, Nate Cinal, Jon Brown, Dan Barker, Tim Perfitt, Ashley MacKinlay, Tobias Linder Philippe Daoust, AJ Potrebka, Adam Burg, & Hamlin Krewson  

The Topline team interview Ethan Smith, founder of Graphite, an San Fransico-based growth and SEO agency with clients like Notion, Webflow and Rippling. As well as Rahul Jain from Noble, a consultant who writes and speaks about AI. Thanks for tuning in! Catch new episodes every Wednesday. Subscribe to Topline Newsletter. Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech. Join the free Topline Slack channel to connect with 600+ revenue leaders to keep the conversation going beyond the podcast! Chapters: 00:00 Introduction and Host Introductions 00:41 How Well Do You Know AI Search? 08:14 SEO vs. AI: The Changing Landscape 13:42 The Role of PR in AI Search 14:46 Get Cited By THESE Websites 18:13 SEO Strategies in the AI Era 25:07 Is SEO Actually Dead? 33:16 HubSpot's Message to The Market 34:27 SEO Evolution and Traffic Trends 34:54 The Future of Search and LLMs 36:34 Signs You Have The Wrong Product 40:01 Scaling AI Search Content 46:38 The Role of PR and AI in Marketing 01:01:42 What Have You Learned?  

Blake breaks down how AI can help with cost segregation and explains why AI currently works best on tasks that take humans 2-5 minutes. Michael Burry is betting against AI companies, claiming they're manipulating earnings by stretching server depreciation from 3-4 years to 5-6 years, adding billions to their bottom lines. Also covered: Intuit's $100 million annual OpenAI deal to integrate QuickBooks and TurboTax into ChatGPT, new bank evidence in the Rippling corporate espionage case, and a survey showing 10% of adults are acting on AI tax advice despite error rates up to 50%.SponsorsOnPay - http://accountingpodcast.promo/onpayRelay - http://accountingpodcast.promo/relayCloud Accountant Staffing - http://accountingpodcast.promo/casChapters(00:00) - Welcome to The Accounting Podcast (00:49) - Blake's Illness and Recovery (02:05) - Upcoming Topics (04:06) - Cost Segregation Explained (06:46) - AI in Cost Segregation (11:15) - AI's Current Capabilities and Limitations (19:10) - Intuit's OpenAI Deal (22:01) - Intuit's Strategy and Industry Implications (30:12) - Michael Burry's New Bet Against AI (31:21) - Depreciation and AI Companies (39:15) - Rippling vs. Deel: Corporate Espionage (42:44) - New Jersey's Alternative Pathways Bill (44:39) - AI's Role in Tax and Investing Advice (47:37) - Defining Audit Quality: PCOB's New Initiative (51:56) - FASB's Costly Lease Standard (56:13) - Ancient Accounting Systems in Peru (58:45) - Conclusion and Viewer Interaction  Show NotesComing soon!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: http://cloudacctpod.link/merchSubscribeApple Podcasts: http://cloudacctpod.link/ApplePodcastsYouTube: https://www.youtube.com/@TheAccountingPodcastSpotify: http://cloudacctpod.link/SpotifyPodchaser: http://cloudacctpod.link/podchaserStitcher: http://cloudacctpod.link/StitcherOvercast: http://cloudacctpod.link/OvercastClassifiedsCollective by DBA - https://collective.cpa/ Want to get the word out about your newsletter, webinar, party, Facebook group, podcast, e-book, job posting, or that fancy Excel macro you just created? Let the listeners of The Accounting Podcast know by running a classified ad. Go here to create your classified ad: https://cloudacctpod.link/RunClassifiedAdTranscriptsThe full transcript for this episode is available by clicking on the Transcript tab at the top of this page

Nasdaq bleibt trotz starker Nvidia-Zahlen volatil. Google bringt Gemini 3 Pro als neues Spitzenmodell auf eigenen TPUs und führt mehrere Benchmarks an. Anthropic verdoppelt seine Bewertung binnen drei Monaten; Microsoft und Nvidia investieren Milliarden. Perplexity startet ein kostenloses Shopping-Tool, bleibt aber ohne klares Geschäftsmodell. Nvidia meldet erneut starkes Wachstum und optimistische Guidance. Baidu kämpft trotz KI-Trend mit rückläufigem Umsatz. Klarnas erste Zahlen seit dem IPO enttäuschen. PDD warnt vor Abschwächung, Temu unter Druck durch neue Importregeln. Larry Summers verlässt das OpenAI-Board. Bei Deel taucht ein Bestechungsskandal auf. Grok lobt Elon Musk überschwänglich. Lutnicks Familie profitiert von KI-Deals. Android Quick Share wird mit iOS AirDrop kompatibel. Unterstütze unseren Podcast und entdecke die Angebote unserer Werbepartner auf ⁠⁠⁠⁠⁠doppelgaenger.io/werbung⁠⁠⁠⁠⁠. Vielen Dank!  Philipp Glöckler und Philipp Klöckner sprechen heute über: (00:00:00) Intro & Nasdaq Volatilität nach Nvidia Earnings (00:03:19) Google Gemini 3 Pro Launch ohne Nvidia-Chips (00:06:32) Anthropic $350B Deal (00:20:34) Perplexity (00:30:08) Nvidia Earnings (00:38:30) Baidu Earnings (00:40:06) Klarna Earnings (00:47:20) PDD Earnings (00:53:53) Larry Summers tritt nach Epstein-Files zurück (00:57:35) Deel Bestechungsskandal gegen Rippling (01:01:34) Grok (01:06:19) Familie Lutnick (01:09:10) Android Quick Share mit iOS AirDrop kompatibel Shownotes US-Tech-Aktien fallen bei Volatilitätsschub an der Wall Street – ft.com Google bringt Gemini 3 heraus, sein bisher 'intelligentestes' KI-Modell – theverge.com Anthropic kooperiert mit NVIDIA und Microsoft, expandiert auf Azure – linkedin.com Anthropic auf $350 Milliarden geschätzt nach Investition von Microsoft, Nvidia – cnbc.com Perplexity kündigt kostenloses Produkt zur Vereinfachung des Online-Shoppings an – cnbc.com Nvidia-Aktien steigen aufgrund unerwartet starker Umsätze und Prognose – cnbc.com Baidu verzeichnet trotz KI-Boom den größten Umsatzrückgang – bloomberg.com Anmelden bei Similarweb Plattform – pro.similarweb.com Klarna übertrifft Umsatzschätzungen im ersten Quartalsbericht seit IPO – cnbc.com Temu-Eigentümer PDD warnt vor Abschwächung in Chinas Konsumsektor – bloomberg.com Musk's xAI baut 500 Megawatt Rechenzentrum in Saudi-Arabien – bloomberg.com Larry Summers tritt aus OpenAI-Vorstand zurück – axios.com Charles Rollet über X: Deel verbuchte angebliches $6k Bestechungsgeld als Geschäftsausgabe – x.com Groks Verehrung von Elon Musk wird seltsam – theverge.com Familienangelegenheit: Söhne des Handelsministers profitieren vom KI-Boom – nytimes.com Android Quick Share jetzt kompatibel mit iOS AirDrop – blog.google

Max Altman is Co‑Founder & Managing Partner at Saga Ventures, a US$125 M early‑stage fund.  Before Saga Max was an investor with Apollo Projects, Hydrazine Capital and Altman Capital (where he helped deploy over US$500 M) into breakout names such as Rippling and Reddit. AGENDA: 03:55 – Venture Capital Is FULL of Tourists With Single-Digit IQs 06:20 – Inside the Madness of Parker Conrad: Genius, Chaos, and WTF Emails 10:35 – The Rippling Deal That Changed Everything 12:40 – Living in Sam Altman's Shadow: The Confession 17:30 – $200M Fund Mistakes: Max's Brutal Lessons From Hydrazine 22:05 – The $2B Reddit Return… and the $2B Left on the Table 25:00 – Why Climate Tech Is a Total VC Mirage 28:40 – The New Seed War: Can Anyone Survive Sequoia & Andreessen? 46:55 – Max's Boldest Predictions  

Why do billions of dollars of stock trade hands based on napkin math and vibes? Billy Gallagher, CEO of Prospect and former Rippling employee, joins Patrick McKenzie (patio11) to walk through the information asymmetry that costs less-sophisticated employees massive amounts of money. From understanding when to early exercise options to navigating 83B elections and tender offers, they discuss the critical decisions that have a shot clock ticking the day you sign your offer letter.–Full transcript available here: www.complexsystemspodcast.com/understanding-equity-at-tech-companies/–Sponsor: Framer is a design and publishing platform that collapses the toolchain between wireframes and production-ready websites. Design, iterate, and publish in one workspace. Start free at framer.com/design with code COMPLEXSYSTEMS for a free month of Framer Pro.–Links:Prospect: www.joinprospect.com/–Timestamps:(00:00) Intro(00:44) Billy's professional journey(01:07) Equity management challenges(02:29) The importance of equity compensation(04:53) Equity grant structures in startups(06:09) Understanding vesting terms(07:09) The value of equity over time(08:48) The myth of options as lottery tickets(11:23) Career tailwinds from startup experience(14:25) Breaking into the tech industry(15:16) The role of equity in compensation(17:49) Employee equity plans and dilution(19:59) Sponsor: Framer(21:06) Stock options vs. RSUs(21:55) The decision to exercise options(27:11) Tax implications of exercising options(33:03) The role of HR in equity management(36:14) Bootleg spreadsheets and vibes-based investing(38:09) Navigating tax complexities in different scenarios(41:31) The importance of extended exercise windows(44:18) Challenges with tax residency and remote work(49:43) The role of accountants in managing equity(53:41) Understanding the 83(b) election and QSBS(01:01:03) Tender offers and secondary sales(01:08:38) Strategies for exercising and selling options(01:12:28) Navigating financial decisions in startups(01:16:59) Wrap

Side A of StrangeCast Episode 120 debuted earlier this week and Adnan Riaz and Adam Evalt are BACK for the Side B part of Player 1 vs The World's podcast episode. The Lost Records Journal co-hosts continue their talk around the aftermath of Life Is Strange: Double Exposure publisher Square Enix dropping its bombshell news on the U.S. and UK-based divisions of the Japanese company.

Arjun Sethi is co-CEO of Kraken, one of the most secure and enduring cryptocurrency platforms. He is also Chairman of Tribe Capital, a leading venture capital firm managing $1.7B in assets, with investments in Block, OpenAI, Rippling, Slack and xAI among others.Previously, Arjun was a Partner at Social Capital, where he led the venture team. He co-founded two startups—LOLapps (acquired by 6waves) and MessageMe (acquired by Yahoo). He joined Yahoo's executive team to lead data and analytics teams and run mobile and emerging products. He also served as a Board Observer, helping to oversee the investment in Alibaba. Arjun has also incubated and co-founded Termina.ai, Kapital, and Foundation Robotics.

Alicia Katz Pollock joins the show fresh from Intuit Connect with detailed notes on everything announced for QuickBooks Online and the accounting profession. The discussion covers Intuit's consolidation strategy to reduce reliance on third-party apps, the new tiered pricing structure for the Intuit Accountant Suite launching in 2026, and how AI agents are currently performing in bank feeds and transaction categorization. They also examine QuickBooks' move into CRM and marketing tools, the role of QuickBooks Live in Intuit's strategy, and what alternatives small businesses and accountants might consider.SponsorsCloud Accountant Staffing - http://accountingpodcast.promo/cas Rippling - http://accountingpodcast.promo/ripplingBILL - http://accountingpodcast.promo/billChapters(00:00) - Introduction and Guest Welcome (00:56) - Intuit Connect Conference Overview (01:32) - Changes in QuickBooks and Intuit's Strategy (02:03) - AI Integration in QuickBooks (05:26) - The New Customer Hub and MailChimp Integration (06:54) - Concerns About AI and QuickBooks Ecosystem (12:10) - ProAdvisors' Role in the AI Era (19:44) - Addressing Reporting and Automation Issues (27:43) - The Future of QuickBooks Online Accountant (28:21) - New Features and Paid Tiers (29:24) - Intuit Accountant Suite Overview (30:40) - Core and Accelerate Versions (30:54) - Client Management and Dashboards (33:22) - Practice Management Tools (34:01) - Intuit's Market Strategy (38:04) - ProAdvisor and QuickBooks Live (40:31) - Quicken's Comeback (43:34) - AI and Automation in Accounting (53:52) - Intuit's Future Plans and Innovations (56:44) - Conclusion and CPE Information  Show NotesComing soon!Listen and Subscirbe to The Unofficial QuickBooks Accountants Podcast!https://uqb.show/subscribeConnect with Alicia Katz Pollock!https://www.linkedin.com/in/aliciakatzpollock/https://royalwise.com/ 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: http://cloudacctpod.link/merchSubscribeApple Podcasts: http://cloudacctpod.link/ApplePodcastsYouTube: https://www.youtube.com/@TheAccountingPodcastSpotify: http://cloudacctpod.link/SpotifyPodchaser: http://cloudacctpod.link/podchaserStitcher: http://cloudacctpod.link/StitcherOvercast: http://cloudacctpod.link/OvercastClassifiedsCollective by DBA - https://collective.cpa/ Want to get the word out about your newsletter, webinar, party, Facebook group, podcast, e-book, job posting, or that fancy Excel macro you just created? Let the listeners of The Accounting Podcast know by running a classified ad. Go here to create your classified ad: https://cloudacctpod.link/RunClassifiedAdTranscriptsThe full transcript for this episode is available by clicking on the Transcript tab at the top of this page

High-volume recruiting is officially in its “everything is on fire” era. Applicant fraud is exploding. Screening is eating recruiter calendars alive. And scaling sourcing without torching your team? Good luck doing that manually in 2025 and beyond. So we're bringing in the people who actually lived it… not analyst fantasy land. In this session — leaders from Rippling, Phantom, Foley and more break down the pain they actually felt, the bad solutions they tried first, and how they finally got ahead of the chaos. You'll hear exactly how the speakers have taken a native approach in catching fraud before it infects pipelines, shrink screening overhead, and put recruiter time back into outbound sourcing where it actually moves the needle — not “spreadsheet archaeology.” Speakers include: Vijay Mani — Co-Founder & CEO, Covey Jay Patel — Sr Director Talent, Rippling (ex DoorDash) Laura Stapleton — VP People, Foley (ex Engine) Derrick Gellidon — Head of Talent, Phantom (ex Lyft, Instacart) And yes… Chad & Cheese stirring the bourbon into the chaos.

Blake and David cover BDO's legal threat against Going Concern over independence questions, Crowe hiring an investment bank to explore private equity options, and Trump pardoning Binance founder after the crypto venture made his family richer than their entire property portfolio. Plus, tariffs create a paperwork nightmare for small businesses, accounting ranked 90th out of 100 best jobs, a film production accountant who embezzled $2 million for Vegas stays and sugar daddy payments, and the Supreme Court hearing arguments on whether Trump's tariffs amount to an illegal $3 trillion tax.SponsorsCloud Accountant Staffing - http://accountingpodcast.promo/cas Rippling - http://accountingpodcast.promo/ripplingChapters(00:00) - Welcome to the Accounting Podcast Live from Intuit Connect (01:16) - Top Story: BDO vs. Going Concern (05:02) - The Fraud Triangle and Independence in Accounting (08:21) - BDO's Response to Allegations (18:02) - Accountants Rank 90th Best Job in the US (19:38) - Stablecoins and Treasury Management (20:28) - Trump Pardons Binance Founder (24:29) - Positive Hiring Outlook in Accounting (25:41) - Impact of Trump's Tariffs (28:44) - Challenges for Small Businesses Due to Tariffs (32:46) - Workplace Friendships and Pay Cuts (34:35) - App News: Keeper Rebrands to Double (37:53) - AI Adoption in Accounting (45:25) - Fraud in Film Production Accounting (48:15) - Private Equity in Accounting Firms (50:49) - Conclusion and Upcoming Events  Show NotesA Message from CEO Wayne Berson to BDO USA Professionals https://www.bdo.com/insights/press-releases/a-message-from-ceo-wayne-berson-to-bdo-usa-professionalsAuditor BDO Cuts Jobs With Focus on Managing Apollo Debt https://www.bloomberg.com/news/articles/2025-10-11/auditor-bdo-cuts-jobs-with-focus-on-managing-apollo-debtAccountants Hold the 90th Best Job in U.S. News & World Report's 2025 Rankinghttps://www.cpapracticeadvisor.com/2025/10/27/accountants-hold-the-90th-best-job-in-u-s-news-world-reports-2025-ranking/171733/Accountant - Career Rankings, Salary, Reviews and Advice https://money.usnews.com/careers/best-jobs/accountantTrump pardons Binance founder Changpeng Zhao, aka "CZ" https://www.cnbc.com/2025/10/23/trump-pardons-binance-founder-cz-zhao.htmlThe Accounting Firm Weighing Private-Equity Ownership After Years of Ignoring Calls https://www.wsj.com/articles/the-accounting-firm-weighing-private-equity-ownership-after-years-of-ignoring-calls-8b7377fcCrowe Ponders PE Investment Amid Middle Market Firm Shake-Up https://news.bloombergtax.com/financial-accounting/crowe-ponders-pe-investment-amid-middle-market-firm-shake-upThe Disproportionate Effects of Declining Interest Within Different Accounting Fields: An Uneven Pipeline (CPA Journal)https://www.cpajournal.com/2025/10/22/the-disproportionate-effects-of-declining-interest-within-different-accounting-fieldsMovie Accountant Charged with Embezzling Nearly $2M From Indie Films https://www.cpapracticeadvisor.com/2025/08/12/movie-accountant-charged-with-embezzling-nearly-2m-from-indie-films/167240/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: http://cloudacctpod.link/merchSubscribeApple Podcasts: http://cloudacctpod.link/ApplePodcastsYouTube: https://www.youtube.com/@TheAccountingPodcastSpotify: http://cloudacctpod.link/SpotifyPodchaser: http://cloudacctpod.link/podchaserStitcher: http://cloudacctpod.link/StitcherOvercast: http://cloudacctpod.link/OvercastClassifiedsCollective by DBA - https://collective.cpa/ Want to get the word out about your newsletter, webinar, party, Facebook group, podcast, e-book, job posting, or that fancy Excel macro you just created? Let the listeners of The Accounting Podcast know by running a classified ad. Go here to create your classified ad: https://cloudacctpod.link/RunClassifiedAdTranscriptsThe full transcript for this episode is available by clicking on the Transcript tab at the top of this page

Outbound prospecting isn't dead, it's just different. TSHP welcomes Jason Bay, outbound sales coach, trainer, and SKO speaker for a conversation about how to outbound smarter. Uncover the math problem haunting sales teams—those dismally low cold call and conversion rates—and explore innovative ways to manage and improve them. Discover how sales reps can benefit from AI tools like ChatGPT for practical, real-world experience, even when live conversations are scarce. Mark and Jason shed light on crafting an effective sales rhythm, and how voicemails can double as marketing messages, guiding prospects to your emails, rather than just seeking callbacks.

Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-quality experiences to business buyers — a lesson that shapes how Serval turns complex IT automation into something that feels magical. In this episode, Jake and Brett dive into the lessons from Verkada that inspired Serval's founding, what it takes to disrupt entrenched enterprise categories, and practical tips for getting deeply embedded with customers and hiring high-quality candidates. In today's episode, we discuss: Why building “in existing categories” can be more powerful than creating new ones The lessons from Verkada that shaped Serval's platform strategy The customer interview question that unlocked the IT buyer's hidden pain points How Serval's automation builder uses AI to generate code-based workflows Redefining engineering and PM roles with forward-deployed engineers Keeping the hiring bar high in an AI-native startup Why there's a “land grab” moment right now in enterprise AI And much more... Where to find Jake: LinkedIn: https://www.linkedin.com/in/jakestauch/ Twitter/X: https://x.com/jakeserval Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Alex McLeod: https://www.linkedin.com/in/alexmcleodio/ Clay: https://www.clay.com Cloudflare: https://www.cloudflare.com Cursor: https://cursor.sh Filip Kaliszan: https://www.linkedin.com/in/kaliszan/ Hans Robertson: https://www.linkedin.com/in/hansrobertson Linear: https://linear.app Okta: https://www.okta.com Rippling: https://www.rippling.com Serval: https://www.serval.com/ ServiceNow: https://www.servicenow.com Verkada: https://www.verkada.com Workday: https://www.workday.com Timestamps: (02:25) Lessons from holding different product roles (07:29) Turning “hard mode” into a moat (10:49) The early days of Serval (12:59) Scratching the founder itch (14:57) Unconventional interview techniques (17:47) Solving core interview challenges (21:10) Planning the early product roadmap (23:03) The surprising power of patience (26:12) Serval's impressive technical advantage (27:35) Disrupting legacy incumbents (31:13) Building for mid-market and enterprise (33:35) Serval's enduring roadmap (36:08) How to sell to an existing market (39:16) The evolving role software plays (43:55) Building for AI that didn't exist yet (49:49) Serval's forward-deployed engineers (58:31) The hybrid PM-GM (1:00:27) “You can over-prioritize” (1:02:48) The unexpected value of panic buttons (1:04:50) What Serval looks for in new talent (1:07:01) The ultimate hiring litmus test (1:13:59) Building out Serval's go-to-market function (1:16:31) The evolving IT market in 2025

Alex Bouaziz is the Co-Founder and CEO @ Deel, the $17BN global payroll juggernaut that just last week announced their latest $300M fundraise led by Ribbit, a16z and Coatue. Deel has been on the most insane journey, they do $1BN+ in ARR, they just had their first $100M revenue month and they have been profitable for over 3 years.  AGENDA: 03:38 Announcing $300M Fundraise at a $17BN Valuation 06:24 Rippling vs Deel: WTF is Going On? Where is the Lawsuit?  14:01 Why 1-1s Are BS and Leaders Should Stop Doing Them 17:31 Do Rich Leaders Make Better Leaders 28:33 Biggest Lesson from Ben Horowitz? Why Most CMOs Are Bad? 34:48 Lessons from Nik @ Revolut and Why Companies Need to Make Their Own Software 42:23 Deel's Acquisition Playbook: Lessons from 13 Acquisitions 45:17 How to Price Acquisitions? How to Align Incentives with Founders? 55:45 Deel is Profitable and Growing Fast: When is the IPO? 01:01:35 Best Acquisition Ever + Worst Ever: What Did We Learn?  

Could an AI catch what auditors and a CFO missed? This week, Blake and David unpack how a founder used Claude to scan QuickBooks and uncover a $2.1M embezzlement in 18 minutes. They also tackle Deloitte's AI ‘workslop' refund, shutdown-driven IRS and air travel woes, the IRS's new “CEO” and crypto ties, OpenAI's personal finance play, EY's audit rebound, BDO's ESOP squeeze, and crypto funds courting CPA clients.SponsorsCloud Accountant Staffing - http://accountingpodcast.promo/cas Rippling - http://accountingpodcast.promo/ripplingAssembly - http://accountingpodcast.promo/assemblyChapters(01:35) - Deloitte's AI Report Scandal (09:05) - Government Shutdown Impact on IRS and Air Travel (23:56) - AI in Accounting: Risks and Opportunities (34:49) - Competing with the Status Quo (35:38) - Pricing Bookkeeping Services (36:31) - Standardizing Services Based on Price (37:14) - Client Needs vs. Service Offerings (38:00) - The Monthly Close Obsession (40:01) - Broken Charts in Financial Reports (43:15) - Cracker Barrel Logo Controversy (47:08) - EY's Audit Quality Turnaround (49:53) - Crypto Investment Schemes (55:48) - BDO's Financial Struggles (01:00:34) - Conclusion and Announcements  Show NotesDeloitte to partially refund Australia for report with apparent AI-generated errors https://abcnews.go.com/Technology/wireStory/deloitte-partially-refund-australian-government-report-apparent-ai-126281611Claude Exposed My Co-Founder's $2M Theft — AI Evidence Turned Into Lawsuit https://techbullion.com/claude-exposed-my-co-founders-2m-theft-ai-evidence-turned-into-lawsuit/New Research: 20% of Americans use AI tools 10X+/month, but growth is slowing and traditional search hasn't dippedhttps://sparktoro.com/blog/new-research-20-of-americans-use-ai-tools-10x-month-but-growth-is-slowing-and-traditional-search-hasnt-dipped/The Danger of Bad Charts https://www.cpajournal.com/2025/10/10/the-danger-of-bad-charts-2/Cracker Barrel's logo controversy was driven by bots https://www.nrn.com/casual-dining/cracker-barrel-s-logo-controversy-was-driven-by-bots-what-operators-should-learn-from-thisOur commitment to audit quality — Ernst & Young LLP's 2025 report https://www.ey.com/en_us/assurance/audit-quality-reportEY drops clients to improve audits after leading Big Four in deficiencies https://www.cfobrew.com/stories/2024/08/27/ey-drops-clients-to-improve-audits-after-leading-big-four-in-deficienciesOpenAI Buys Personal Finance App Roi https://www.pymnts.com/acquisitions/2025/openai-buys-personal-finance-app-roi/With its latest acqui-hire, OpenAI is doubling down on personalized consumer AI https://techcrunch.com/2025/10/03/with-its-latest-acqui-hire-openai-is-doubling-down-on-personalized-consumer-ai/BDO USA Expands Professional Services Capabilities Through HORNE https://www.bdo.com/insights/press-releases/bdo-usa-expands-professional-services-capabilities-through-horneAuditor BDO Cuts Jobs With Focus on Managing Apollo Debt https://www.bloomberg.com/news/articles/2025-10-11/auditor-bdo-cuts-jobs-with-focus-on-managing-apollo-debtNeed 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: http://cloudacctpod.link/merchSubscribeApple Podcasts: http://cloudacctpod.link/ApplePodcastsYouTube: https://www.youtube.com/@TheAccountingPodcastSpotify: http://cloudacctpod.link/SpotifyPodchaser: http://cloudacctpod.link/podchaserStitcher: http://cloudacctpod.link/StitcherOvercast: http://cloudacctpod.link/OvercastClassifiedsCollective by DBA - https://collective.cpa/ Want to get the word out about your newsletter, webinar, party, Facebook group, podcast, e-book, job posting, or that fancy Excel macro you just created? Let the listeners of The Accounting Podcast know by running a classified ad. Go here to create your classified ad: https://cloudacctpod.link/RunClassifiedAdTranscriptsThe ...

Truth for Soul Progress is a 5-part journey exploring truth as the foundation of spiritual growth. Each episode reveals a unique key—from enabling truth to courage in storms to meditations that let truth ripple outward in light. Together, these five keys work synergistically to free the soul, strengthen character and illuminate the path of progress. In this meditation episode, Dr. Judith guides you on a journey to discover the transformative power of truth. Explore how speaking your truth creates ripples of light that positively impact your soul and extend far beyond into the world around you. Through deep breaths and visualizations, enter your inner sanctuary, find peace, and let the healing light of truth flow. Learn how each act of honesty brings clarity, freedom, and courage, and feel the eternal support of your higher self-amplifying these energies. Take this time to release truths you've been holding back, and witness how they bless not only your life but also the lives of others.00:00 Introduction to Meditation on Truth00:38 Preparing the Body and Mind01:54 Entering the Inner Sanctuary03:47 The Ripple Effect of Truth07:19 Facing Unspoken Truths11:35 The Presence of Higher Self15:10 Reflecting on the Importance of Truth19:37 Final Reflections and Closing

“I wouldn't be able to be the Chief Marketing Officer of the company without AI. … It's like having a person expert in marketing that explains things exactly the way I want to understand them.” -Gianluca Ferremi   Gianluca is a technology expert with over 25 years of experience in innovation and digital transformation. He's launched two AR/VR educational apps used by 35,000 students, generated $46.5M in B2B sales, and co-launched the first low-cost Pay TV in South Africa. Specializing in soft skills development, Gianluca believes in an education that values human talent and personal growth. Website: https://www.wisepath.ai/ LinkedIn: https://www.linkedin.com/in/gianlucaferremi/    Most product demos suck. Madhav knows this better than anyone—after a decade in B2B marketing, he's seen thousands of terrible demos kill deals. That's why he leads marketing at Storylane, where 4,000+ teams like Gong, Clari and Rippling now create killer demos in 2 minutes instead of 2 weeks. Website: https://www.storylane.io/ LinkedIn: https://www.linkedin.com/in/madhavbhandari/ YouTube: https://www.youtube.com/@StorylaneOfficial/videos   In this episode, we explore the intersection of education, technology, and storytelling—how innovation in both learning and marketing can unlock growth, impact, and connection.   Apply to join our marketing mastermind group: https://notypicalmoments.typeform.com/to/hWLDNgjz   Follow No Typical Moments at: Website: https://notypicalmoments.com/ LinkedIn: https://www.linkedin.com/company/no-typical-moments-llc/ YouTube: https://www.youtube.com/channel/UC4G7csw9j7zpjdASvpMzqUA Instagram: https://www.instagram.com/notypicalmoments Facebook: https://www.facebook.com/NTMoments

“I wouldn't be able to be the Chief Marketing Officer of the company without AI. … It's like having a person expert in marketing that explains things exactly the way I want to understand them.” -Gianluca Ferremi   Gianluca is a technology expert with over 25 years of experience in innovation and digital transformation. He's launched two AR/VR educational apps used by 35,000 students, generated $46.5M in B2B sales, and co-launched the first low-cost Pay TV in South Africa. Specializing in soft skills development, Gianluca believes in an education that values human talent and personal growth. Website: https://www.wisepath.ai/ LinkedIn: https://www.linkedin.com/in/gianlucaferremi/    Most product demos suck. Madhav knows this better than anyone—after a decade in B2B marketing, he's seen thousands of terrible demos kill deals. That's why he leads marketing at Storylane, where 4,000+ teams like Gong, Clari and Rippling now create killer demos in 2 minutes instead of 2 weeks. Website: https://www.storylane.io/ LinkedIn: https://www.linkedin.com/in/madhavbhandari/ YouTube: https://www.youtube.com/@StorylaneOfficial/videos   In this episode, we explore the intersection of education, technology, and storytelling—how innovation in both learning and marketing can unlock growth, impact, and connection.   Apply to join our marketing mastermind group: https://notypicalmoments.typeform.com/to/hWLDNgjz   Follow No Typical Moments at: Website: https://notypicalmoments.com/ LinkedIn: https://www.linkedin.com/company/no-typical-moments-llc/ YouTube: https://www.youtube.com/channel/UC4G7csw9j7zpjdASvpMzqUA Instagram: https://www.instagram.com/notypicalmoments Facebook: https://www.facebook.com/NTMoments

Blake and David examine the growing threat of AI-generated fake receipts, with 32% of accountants unable to recognize fraudulent documents and 30% reporting an increase in fraud since last year. They also discuss the concerning decline in entry-level auditor positions (down 43% since January) as firms adopt AI automation, while nearly half of accounts payable professionals now fear layoffs and also explore the concept of "work slop"—low-quality AI-generated work costing businesses nearly $200 per employee monthly—and debate whether firms should require clients to use standardized technology stacks, with only 37% currently doing so. SponsorsCloud Accountant Staffing - http://accountingpodcast.promo/cas Rippling - http://accountingpodcast.promo/ripplingBill.com - http://accountingpodcast.promo/bill.comBluebook - http://accountingpodcast.promo/bluebookChapters(01:43) - Headline Story: Tech Stack Adoption in Accounting Firms (03:05) - Survey Insights: Tech Stack Usage in Firms (07:15) - AI's Impact on Entry-Level Jobs (13:55) - The Rise of 'Work Slop' and Its Costs (20:44) - AI and Automation in Accounting (25:08) - Human-in-the-Loop Automation with Zapier (28:22) - AI in Tax Research and IT Blockers (30:51) - Competitive Moats and Custom Bots (32:26) - Exciting Changes in CPE Standards (34:59) - Drake Software's Cloud-Based Tax Solution (43:06) - State Department Embezzlement Scandal (44:59) - Trump's Tariff Announcements (50:28) - H-1B Visa Fee Increase (56:20) - Conclusion and CPE Information  Show Notes32% of accountants can't recognize AI-generated fake receipts https://www.accountingtoday.com/news/32-admit-they-cannot-recognize-ai-generated-fake-receiptsEntry-level auditor job postings fell 43%, per Randstad https://www.accountingtoday.com/news/entry-level-auditor-job-postings-fell-43-per-randstadAI-Generated "Workslop" Is Destroying Productivity https://hbr.org/2025/09/ai-generated-workslop-is-destroying-productivity97% say CPA firms not using tech efficiently says survey https://www.accountingtoday.com/news/97-say-cpa-firms-not-using-tech-efficiently-says-surveyCPA.com & BILL Growth Survey: How Firms Plan to Stay Ahead https://www.bill.com/blog/cpa-and-bill-growth-technology-surveyAP Pros Face Growing Layoff Concerns and See Automation as a Career Lifeline https://www.cpapracticeadvisor.com/2025/09/11/ap-pros-face-growing-layoff-concerns-and-see-automation-as-a-career-lifeline-2/168818/Get more control over your workflows with Human in the Loop! https://help.zapier.com/hc/en-us/articles/38838619533069-Get-more-control-over-your-workflows-with-Human-in-the-Loop54% use AI in tax research, but search engines remain prominent https://www.accountingtoday.com/news/54-use-ai-in-tax-research-but-search-engines-remain-prominentDrake Software Introduces Drake Tax Online https://www.cpapracticeadvisor.com/2025/09/24/drake-software-introduces-drake-tax-online/169572/Drake Software Launches Drake Tax Online: Powerful, Flexible Tax Software in the Cloud https://www.prnewswire.com/news-releases/drake-software-launches-drake-tax-online-powerful-flexible-tax-software-in-the-cloud-302566087.htmlNASBA, AICPA release proposed revisions to CPE standards https://www.journalofaccountancy.com/news/2025/sep/nasba-aicpa-release-proposed-revisions-to-cpe-standardsNASBA, AICPA Release Exposure Draft of Proposed Revisions to CPE Standardshttps://nasba.org/blog/2025/09/15/revisions-to-cpe-standards-2025/ H-1B FAQhttps://www.uscis.gov/newsroom/alerts/h-1b-faq 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: http://cloudacctpod.link/merchSubscribeApple Podcasts: http://cloudacctpod.link/ApplePodcastsYouTube: https://www.youtube.com/@TheAccountingPodcastSpotify: http://cloudacctpod.link/SpotifyPodchaser:

In this episode of the Dental Boardroom Podcast, host Wes Read, CPA and financial advisor at Practice CFO, continues the discussion on putting your kids on payroll as a smart tax and wealth-building strategy. This time, he dives deeper into how to maximize the benefits by pairing payroll with 529 education savings accounts and Roth IRAs.Key Takeaways:Shifting income for tax savings:Move income from a higher parent tax bracket to your child's 0% bracket (standard deduction in 2025 is $15,750).Saves roughly $3,000–$4,000 per child per year. Over many years, that adds up significantly.Practical execution:Children can start as early as age 6–7 and continue through college years.Create job descriptions and light documentation (e.g., photos, office work, modeling fees) to substantiate employment.Use a modern payroll service (Wes recommends Rippling) to simplify compliance.How to use the payroll funds:Deposit paychecks into the parent's checking account (simpler than setting up child accounts).Direct those funds toward:A custodial Roth IRA (tax-free growth).A 529 education savings account (tax-free growth + tax-free qualified withdrawals).529 Education Plans explained:State-administered plans with varying benefits Utah's “My529” (Vanguard, low-cost index funds) is Wes' favorite.Benefits:Tax-free growth and withdrawals for education.Potential state tax deductions in some states.High contribution limits.Parent-owned accounts are more favorable for financial aid and offer flexibility to transfer funds among siblings.Can cover not just college, but also K–12, trade schools, apprenticeships, and up to $10K in student loan repayment.Suggested split strategy:After payroll and FICA taxes, about $14K remains per child.Example: Fund $7K to a Roth IRA + $7K to a 529 plan, balancing retirement savings with education funding.Risk & compliance notes:Wes has never seen an IRS audit on this strategy in 17+ years, but stresses proper documentation.Pay a fair wage aligned with actual work performed.Always consult your CPA if unsure.Big picture:This is more than just tax savings it's wealth building.Combining small strategies like payroll, home office, auto deductions, and retirement plans can collectively cut taxes by 30–60% (or more) and accelerate financial independence.Why This Matters:By intentionally leveraging tax rules, you can redirect money that would have gone to the IRS into your kids' education, retirement, or family wealth. Over time, these small wins compound into major financial independence.

Howie Liu is the co-founder and CEO of Airtable, the no-code platform valued at around $12 billion. After a viral tweet declared “Airtable is dead” based on incorrect data, Howie led a radical transformation: reorganizing the entire company around AI, becoming an “IC CEO” who codes daily, and achieving over $100 million in free cash flow.What you'll learn:1. The “fast thinking” vs. “slow thinking” team structure that lets Airtable ship AI features weekly (inspired by Daniel Kahneman)2. Why Howie uses AI hourly (not daily) and is Airtable's #1 inference-cost user globally3. Why CEOs must become ICs again in the AI era (and how to restructure your calendar to make it possible)4. Why “playing” with AI tools should be mandatory—Howie tells employees to cancel all meetings for a week to experiment5. The specific skills product managers, engineers, and designers need to develop to succeed in the AI era6. Why evals can kill innovation (and when to use “vibes” instead)—Brought to you by:LucidLink—Real-time cloud storage for teamsDX—The developer intelligence platform designed by leading researchersClaude.ai—The AI for problem solvers and enterprise—Where to find Howie Liu• X: https://x.com/howietl• LinkedIn: https://www.linkedin.com/in/howieliu/• Email: howie@airtable.com—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 Howie Liu and Airtable(04:05) The “Airtable is dead” viral tweet controversy(08:07) The rise of IC CEOs(10:57) AI's paradigm shift in product development(16:27) Specific changes Airtable has made(21:38) Fast- and slow-thinking teams(32:57) The emergence of new form factors in AI models(34:48) Airtable's vision and philosophy(40:20) Empowering teams with AI tools(46:50) Encouraging experimentation and play(50:55) Cross-functional skills in product teams(01:03:35) The importance of evals and open-ended testing(01:08:06) Key strategies for AI-driven success(01:12:43) Counterintuitive startup wisdom(01:22:21) Don't step away from the details that you love(01:25:50) Advice for aspiring engineers and designers(01:30:00) Lightning round and final thoughts—Referenced:• Airtable: https://www.airtable.com/• All In podcast: https://allin.com/• Nikita Bier on X: https://x.com/nikitabier• Figma: https://www.figma.com/• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder and CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper• Every: https://every.to/• 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• Windsurf: https://windsurf.com/• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan• Rippling: https://www.rippling.com/• Omni: https://www.airtable.com/lp/ai-psu-plp• How ChatGPT accidentally became the fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Palantir: https://www.palantir.com/• Harvey: https://www.harvey.ai/• v0: https://v0.dev/• 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• Lovable: https://lovable.dev/• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Runway Game Worlds: https://play.runwayml.com/login• Sesame: https://www.sesame.com• NotebookLM: https://notebooklm.google• Salesforce: https://www.salesforce.com• Andrew Ofstad on LinkedIn: https://www.linkedin.com/in/aofstad/• Stripe: https://stripe.com/• Eames chair: https://en.wikipedia.org/wiki/Eames_Lounge_Chair• OpenAI's CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai• Anthropic's CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next• IDEO design thinking: https://designthinking.ideo.com/• Brian Chesky's new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• The Studio on AppleTV+: https://tv.apple.com/us/show/the-studio/umc.cmc.7518algxc4lsoobtsx30dqb52• Silicon Valley on HBOMax: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d• Self Edge: https://www.selfedge.com/• Studio D'Artisan: https://www.selfedge.com/studio-dartisan• Whitesville T-shirt: https://store.toyo-enterprise.co.jp/shopbrand/ct48/• Guest Series | Dr. Paul Conti: How to Understand & Assess Your Mental Health: https://www.hubermanlab.com/episode/guest-series-dr-paul-conti-how-to-understand-and-assess-your-mental-health—Recommended books:• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032• Trauma: The Invisible Epidemic: How Trauma Works and How We Can Heal From It: https://us.amazon.com/Trauma-Invisible-Epidemic-Works-Heal/dp/1683647351/—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

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader My guest: Sam Lessin is a Partner at Slow Ventures, with prior experience as Vice President of Product Management at Facebook and CEO of Drop.io. His career highlights include serving as a key executive at Facebook, leading product management efforts, and successfully co-founding Fin. His current role at Slow Ventures involves investing in innovative startups across various sectors, showcasing his expertise in entrepreneurship and venture capital. Notes: Key Learnings The 4:30 AM Advantage – Sam's father would be at his desk by 4:30 AM every day, saying, "It's easy to look smart if you have a several-hour head start on everyone else." Early work creates compounding advantages over time. Either Be Early or Be Late, Don't Be On Time – Father's wisdom about timing and seasons. Start your career super early to get ahead, or strategically wait and come in later. Timing matters more than perfect preparation. Joy as the Ultimate Competitive Advantage – "I just don't think that in the long run, angry people win." Look for joyful people in hiring and partnerships because joy is sustainable while anger burns out. Type Two Fun Builds Resilience – Type 1 fun is enjoyable while doing it (rollercoaster). Type 2 fun "completely sucks while you're doing it, but there's joy on the other side" (climbing mountains, marathons). Entrepreneurs need Type 2 fun experiences. Practice Voluntary Hardship – Sam ran a sub-3-hour marathon and got a pilot's license not for love of activities, but for "practice moments" of perseverance. Creates evidence that you can handle business adversity. Right Person, Right Opportunity, Right Time – Don't ask "is this a great person?" Ask, "Is it the right person at the right moment?" Success requires all three elements to align, not just talent. Write Publicly for Intellectual Receipts – "If you can't write the check, write me the thesis and timestamp it." Writing creates accountability, proves thinking ability, and builds reputation over time. Nobody Knows What They're Doing – Working at Bain taught Sam that even prestigious companies "have no idea what you're doing." This is liberating—you can figure it out too. Big Things Take Time (Slow Ventures Philosophy) – Most success isn't quick wins. Venmo took "so many turns of the crank." Be patient finding the right wind, then sail fast when you catch it. Embrace Being Wrong Most of the Time – Seed investing means "you're mostly wrong, you mostly lose money." Success comes from being very right occasionally, not being right consistently. The Solana 2000x Return Story – Put in $400K, returned 2000x to LPs. Success came from the intersection of thesis (looking for "Ethereum killer") and relationships (following Raj Gokal through multiple startups). Use Humor and Authenticity as Filters – Slow Ventures website looks like a law firm in tuxedos "on purpose." If you don't think it's funny, "you're not who we want to invest in." Writing Pushes Away Wrong People – "I really like to be not liked by the people I don't want to work with." Authentic writing attracts the right people and repels the wrong ones. Manufacturing Hardship for Privileged Kids – "Tiger Dad" sports culture might be a misguided attempt to create necessary adversity for wealthy children who lack natural hardships. I loved the throughline of this whole conversation being about his dad, working exceptionally hard, and having joy and excitement for the journey. Maybe it was the near-death experiences that his dad had that led to that mindset. Regardless, it's something we can all learn from. We want to be around optimistic people who have joy and love for what they're doing… Nobody knows what they're doing. We're all figuring it out as we go. You'll never learn unless you go out and do the thing. Figure it out as you go. Just get started. And iterate. Learn. Try again. And keep going. Advice from Sam – Write publicly. You don't know what you think until you get your thoughts out of your head onto the page. And if you publish them, you have a record of the journey. Also, you might attract someone to work with. That is how Jack Raines (guest on episode #539) caught Sam's attention, and now they work together. Useful Quotes: "It's easy to look smart if you have a several-hour head start on everyone else." "I just don't think that in the long run, angry people win." "Either be early or be late, don't be on time." "The right question is, is it the right person at the right moment?" "Writing is thinking. If you can't write, you can't think." "I feel like a tenured professor of capitalism—responsible to make a lot of money over the long term by being very right every once in a while with permission to be wrong all the time." "One of the most insulting things you can call someone is a market participant." "The beauty of the internet is so big. The right people find you." "Big things take time." "Life's short. Is this really what you're spending your time on?" Apply to be part of my next Learning Leader Circle. Time Stamps: 00:11 Sam's Dad's Unique Career Path 00:39 Life Lessons from My Dad 04:35 The Trade-offs of Hard Work 06:57 Betting on the Right People 07:23 The Importance of Joy in Success 10:39 Overcoming Hardships and Building Resilience 20:40 My Journey: From Harvard to Bain 26:06 Joining Facebook and Learning from Mark Zuckerberg 29:36 Balancing Joy and Competitive Spirit 30:15 The Story of Rippling and Parker 31:48 The Solana Investment Journey 34:33 The Importance of Writing and Public Thought 41:07 The Philosophy Behind Slow Ventures 52:54 Advice for Aspiring Venture Capitalists 55:46 Future Plans

My guest today is Ramtin Naimi. Ramtin is the founder of Abstract Ventures, one of the most talked-about seed funds in Silicon Valley. What makes Ramtin's story so compelling isn't just his firm's remarkable track record—including early investments in Rippling, Solana, and dozens of unicorns—but also the unconventional path he took to get there. From running a hedge fund straight out of high school to filing for bankruptcy at 24, then bootstrapping his way to building a $2 billion AUM venture firm using AngelList and relentless hustle. Our conversation begins in an unexpected place—the art world—where Ramtin has become a sophisticated collector, learning from mentors like Michael Ovitz about market dynamics that surprisingly mirror venture capital. We dive deep into how the art world actually works, and Ramtin explains how these lessons about "masterpieces" apply directly to identifying power-law companies in venture. We go deep on his approach to early-stage investing and how he built Abstract as a co-investment vehicle alongside firms like Sequoia, Benchmark, and Andreessen Horowitz. We explore his portfolio construction model, his philosophy on dilution-sensitive founders, and why he takes upwards of 30 pitch meetings per week to build his "frame of reference." We discuss why Abstract has the highest graduation rate from seed to Series A among all seed funds, and how this competitive advantage compounds over time. This is his first time telling his story, and we discuss the power of pattern recognition, relentless work ethic, and the unique opportunities available to those willing to start from scratch in Silicon Valley. Please enjoy this great conversation with Ramtin Naimi. Colossus Review Profile: Ramtin Naimi For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠here⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp.com/invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:40) Learning from Mentors and Starting to Collect (00:08:50) Parallels Between Art and Venture Capital (00:12:57) Challenges in Art Collecting (00:20:45) The Role of Status in the Art World (00:25:00) Who Makes the Most Money in the Art World? (00:28:19) Abstract Ventures: Early Stage Investing (00:42:34) Starting a Venture Capital Firm from Scratch (00:43:12) Overcoming Bankruptcy and Early Struggles (00:50:34) Evaluating Technical Capabilities and Momentum (01:02:53) Competing for Deals and Building Relationships (01:15:25) The Role of Brand in Venture Capital (01:22:39) Early Life and Entrepreneurial Beginnings (01:28:40) Starting a Hedge Fund and Learning Hard Lessons (01:31:26) Transition to Venture Capital (01:37:19) Building Abstract and Family Life (01:52:03) The Kindest Thing Anyone Has Done For Ramtin