Podcasts about Brex

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

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

For today's essential Heretics 101 feature, Disruptive HR founder Lucy Adams dissects HR's fundamental trust problem: why designing policies around your worst employees destroys organizational performance, and how to reimagine the business partner role.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(04:15) HR's Fundamental Trust Problem & Designing for the Minority(08:30) Sponsor: Metaview(09:00) The Opportunity Cost of Distrust(12:00) The HRBP Role: Why It's Broken & How to Fix It(15:30) What HR Leaders Are Talking About: DEI, AI & Merit(19:53) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

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

On today's Dear Heretics segment, Nolan and Kelli debate equity compensation philosophy: whether companies should extend stock options to all employees or reserve them for senior roles, weighing moral imperatives against investor dilution concerns and implementation complexity.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(01:07) Question about stock options for all employees(01:48) Carta's philosophy on making everyone an owner(03:32) Moral case for giving equity to everyone(05:07) Story about Carta's employee refresh and Fred Wilson(06:21) Challenge of educating employees on equity(08:28) Pendo's approach to equity education and round tables(09:19) Setting expectations with $0 default value(10:08) Sponsor - Metaview(11:29) Cost of labor adjustments for equity across locations(13:00) Administrative challenges of geo-based equity adjustments(14:16) Employee communication and comparison issues(16:10) Board tension over equity dilution decisions(17:28) Attracting great talent requires competitive compensation(18:06) Moral case and taxes of giving equity(19:00) Importance of working with equity experts(19:46) Closing thoughts on geo strategy and communication(21:34) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

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

On today's Dear Heretics segment, Nolan and Kelli tackle a question on navigating layoffs, revealing hard-won lessons from cutting deep, treating people humanely, and avoiding rookie RIF mistakes.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(03:22) Dear Heretics: What to Know Before Your First RIF(05:10) The Carta Layoff Playbook: Cut Deep, Stay Humane, Do It Once(09:19) Sponsor: Metaview(10:41) Change Management: Why Before and After Matter Most(15:00) Opt-In Severance and Tucking In Top Performers(19:00) Designing for Trust Over Fear(22:04) Leadership Accountability and the Golden Rule(24:11) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

James Reggio (CTO @ Brex) shares the story of "Brex 3.0", an 18-month journey behind their operational evolution. We explore how they rewound their org from a Series E to a Series C mindset, and replaced siloed OKRs with seasonal "marquee initiatives." James deconstructs the “Brex Hacker House”, an AI-focused startup within a startup experiment aimed to disrupt their core business. This conversation is all about evolving operational rhythms, layers of management, product building, and culture change! ABOUT JAMES REGGIOJames Reggio is Brex's Chief Technology Officer. James is a forward thinking technology leader who currently oversees Brex's entire Engineering org. James joined Brex in 2020 as Principal Engineer and has played a vital role in building the company's mobile app and AI capabilities. Prior to Brex, James had an extensive career as a Software Engineer at leading companies such as Microsoft, Salesforce, AirBnB, Stripe and more. Additionally, James founded two companies: Altair Management and Banter, a social discovery platform for podcasts that was later acquired by Convoy in 2018. James received his B.A. of Science from The University of Texas Austin. SHOW NOTES:The birth of Brex 3.0: Using a layoff as a "moment to refound the company" (3:38)Moving from a Series E to a Series C operational mindset (5:28)The problem with a GM model: How siloed OKRs and roadmaps created "deadlock" (6:07)New rituals: Why the CEO became "chief editor of the roadmap" (8:16)The impact on morale: "Folks just knew how their work fit into the bigger picture" (11:16)The challenge of the new model: Who do you hold accountable when you "win and lose as a team"? (13:43)The lesson for reintroducing systems: "Less is more" (15:43)The "Startup within a Startup": Launching an internal team to disrupt Brex (16:49)“What if we were founding Brex again today?” The 4 constraints for the "Hacker House" experiment (17:58)Questions eng leaders should ask when running a similar experiment to Brex (21:02)Aha moment: "With agentic coating, code is so cheap" (22:35)Managing the two narratives: "compounding" the core biz vs. “innovating" with AI (26:01)A surprising dynamic: Why the AI team struggled to see their impact (while the core team didn't) (29:38)Building alongside your customer to iterate / experiment faster (36:06)The turnaround is over: Brex hits 50% YoY growth and cash-flow positive (38:45)Rapid fire questions (42:10) This episode wouldn't have been possible without the help of our incredible production team:Patrick Gallagher - Producer & Co-HostJerry Li - Co-HostNoah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/Dan Overheim - Audio Engineer, Dan's also an avid 3D printer - https://www.bnd3d.com/Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

This week, we chat with Amber Atherton!Amber is a British entrepreneur and investor based in San Francisco. She's a Partner at Patron, an early-stage venture capital firm shaping the future of gaming and online communities, and the Founder of The Atherton Award, which honors young women pursuing careers in STEM and entrepreneurship.A lifelong builder, Amber began coding as a kid in Hong Kong before founding Zyper, a Y Combinator–backed community software startup that used NLP and computer vision to connect creators and their top fans. Zyper was later acquired by Discord, where Amber led growth, launched new international markets, and spearheaded revenue initiatives.Recognized by Forbes 30 Under 30 and Business Insider's Rising Stars in VC, Amber continues to shape the future of community, technology, and venture.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Amber AthertonThe Rise Of Virtual Community Books@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

On today's HR Heretics, Nolan and Kelli dissect a viral LinkedIn post from an ex-Amazon director, exploring how inflated tech worker expectations clash with today's brutal job market realities.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/__For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(00:19) What Ex-Amazon Talent Deserves(01:22) A Post Full of Assumptions(02:41) The X Response: Out of Touch and Ego-Driven(03:11) Sponsor: Metaview(03:34) The Remote Work Reality: That Era Is Over(04:39) The ChatGPT Turning Point: When Employment Fell Off a Cliff(06:01) Why This LinkedIn Post Won't Help Her Job Search(06:29) The Coming Social Unrest and Displaced Tech Workers(07:40) The Grinding Mindset(09:09) When the Rules Changed Overnight(10:31) The FAANG Halo Effect Is Dead(11:55) The Quality of Life Fork: Ejecting from Tech(13:00) Re-Underwriting Your Career in the New Reality(14:20) Expectations Minus Reality Equals Happiness(14:39) Hedging Your Bets: Diversify Before It's Too Late(15:52:) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In this episode of HR Heretics, Kelli and Nolan interview Arnnon Geshuri, Chief People Officer at Snowflake and 8-year Tesla veteran, about building HR's strategic authority through data analytics, his automate-augment-human AI framework, and why he recruits economists and data scientists alongside traditional HR professionals.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH ARNNON, NOLAN + KELLI ON LINKEDINArnnon: linkedin.com/in/arnnongeshuriNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—Snowflake: https://www.snowflake.com/en/-For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(0:00) Intro(1:12) Three Key Lessons from Working with Elon Musk at Tesla(3:36) Why Snowflake: Reinventing the People Function(4:33) The Three-Pronged AI Framework: Automate, Augment, Human-Only(12:02) Sponsor: Metaview(19:45) Data Analytics as the Backbone of HR(24:00) Building the Winning HR Team Portfolio(27:08) Speed Through Imperfection: Fast Pilots and Iteration(29:00) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

This week, we chat with Des Traynor! Des is the Co-founder and Chief Strategy Officer of Intercom, the company behind Fin.ai, and he also sits on Intercom's board of directors. Over the years, Des has led teams across Product, Marketing, Customer Support, and Content, playing a key role in shaping Intercom into one of the most influential customer communication platforms in the world. Today, he oversees Intercom's R&D team, based in Dublin and London.Before founding Intercom, Des was a UX consultant, a university lecturer in computer science, and a Ph.D. researcher focused on improving computer science education. He also previously co-founded Exceptional, a software company acquired by Rackspace.Beyond his work at Intercom, Des is an author, speaker, and angel investor, sharing insights on startups, product strategy, and scaling companies through books, podcasts, and conferences. He's also an investor in some of the most notable startups of our time — including Miro, Stripe, Notion, and Hopin.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Des Traynor: @destraynorFin AI: fin.ai@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

For today's essential Heretics 101 feature, Kelli and Nolan have a candid discussion with Silicon Valley operator Molly Graham on founder depression, imposter syndrome, executive team dynamics, and building business-first people operations at scaling companies.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH MOLLY, NOLAN + KELLI ON LINKEDINMolly: https://www.linkedin.com/in/mograham/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—Glue Club: https://www.glueclub.com/-For coaching and advising inquire athttps://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(00:43) Origin of “Giving Away Your Legos”(02:28) Emotions at Work(02:49) Meet Bob the Monster(04:15) Founder Depression Reality(06:27) The Emptiness of Startups(08:00) Life as a Barter Economy(09:14) “I Can't Do Math” - Professional Moron Strategy(12:00) Growth Solves All Problems(13:00) When Leaders Hate Each Other(14:20) 50% Executive Hiring Success Rate(17:00) 18-Month Executive Tenure(18:34) Business First, Not Happiness(21:00) Era of Excess Is Over(21:51) Best Interview Question(22:05) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

On today's Dear Heretics segment, Kelli and Nolan analyze why traditional bonus programs fail at early-stage companies, advocating for flexible sprint incentives and spot bonuses over rigid annual structures that create organizational debt.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—For coaching and advising inquire athttps://kellidragovich.com/—TIMESTAMPS:(00:00) Introduction: The Bonus Program Question(01:04) The Cyclical Wave & Sales Incentives(01:42) Why Early-Stage Companies Struggle(02:46) The Coin-Operating Problem(03:26) The 96% Problem: Legacy & Recruiting Pressure(04:34) You Can't Put the Toothpaste Back(05:30) Equity Over Bonuses(06:09) Inconsistent Application Across Teams(06:43) Walking It Back Is Brutal(08:06) Sponsor: Metaview(09:28) Technical Debt vs People Debt(11:10) Second Order Consequences(12:31) MBOs Are a Fable(12:53) The Solution: Sprint Incentives(14:04) Surprise and Delight: Spot Bonuses(15:08) Discretionary Budgets & Agility(15:54) Final Thoughts: Avoid People Debt(15:59) Outro This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

Today on HR Heretics, we're excited to cross post a conversation from Metaview's 10x Recruiting Podcast featuring Viet Nguyen, Head of Global Recuiting Operations of Vercel, on using AI to analyze top interviewers' transcripts, extracting their unconscious patterns and building tools that scale interviewing excellence.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH VIET, NOLAN + KELLI ON LINKEDINViet: https://www.linkedin.com/in/vietnguyen6/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—Vercel: https://vercel.com/-For coaching and advising inquire athttps://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(00:13) Progress Over Perfection(01:00) Why Throwing Messy Data at AI Actually Works(01:37) The Three-Hour Experiment That Changed Everything(02:38) Create Leverage Where Possible(03:30) Do Nothing vs. Do Something: The Real Choice(04:00) Sponsor: Metaview(04:14) Interview Begins: Meet Viet Nguyen(04:51) The Rejection That Led to Friendship(05:26) The Five-Year Tour of Duty in Recruiting Ops(06:37) From Zero Coding Skills to Building AI Tools(08:00) The Gaspar Effect: Decoding Your Best Interviewer(10:30) What Makes a Great Interviewer Great?(13:45) Building the Automated Back-Channel Reference Tool(17:20) The RAG Database That Knows Everyone(20:00) When AI Says “No Connections Found” (And Why That's Okay)(23:15) The Webhook That Keeps Your Database Fresh(26:51) Perfect Is the Enemy of Progress(28:00) “Anybody Can Cook” - The Non-Technical Builder's Manifesto(28:27) Automating Interview Debriefs: The Next Frontier(29:28) Real-Time Debrief Summaries: The Dream State(30:04) Where to Find Viet(30:33) Community Show and Tell: The Vision(31:15) We're All Stupid Together (And That's the Point)(32:05) Friday Night Recruiting Projects (32:18) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

This week, we chat with Amanda Goetz! Amanda Goetz is a 2x Founder, CEO and 4x CMO. She is an inspirational writer and content creator captivating millions of people every month through her social insights and newsletter “Life's a Game”. Amanda graduated Summa Cum Laude from the University of Illinois at Urbana-Champaign and went on to lead marketing teams at Ernst & Young, The Knot and still advises as Fractional CMO to multiple startups. She started her last company, House of Wise, during the pandemic in her garage, raised two rounds of venture capital and sold it in 2022 all while homeschooling three young children as a single mom. She found love again and lives with her partner and 3 kiddos in Miami, FL after a decade dodging hustle culture in NYC.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Amanda Goetz: @theamandagoetzhttps://www.amandagoetz.com/@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

 This episode with Jason James from Tezi briefly vanished from Spotify. Don't ask us why. But it's too good to not share again. So here's Jason unpacking the future of recruiting. Please enjoy.Jason James doesn't sugarcoat it: recruiting coordinators and sourcers won't exist in 5 years. In this episode, James (Co-founder and COO of Tezi) sits down with Kelli and Nolan to discuss how to screen 3000 applicants in minutes, why most great resumes just rode the elevator up at hypergrowth companies, and why AI bias audits set a higher standard than humans ever could.Support our Sponsors:Ethena is the compliance training platform built for modern workplaces. Visit goethena.com/heretics and get 10% off your first year.Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH JASON, NOLAN + KELLI ON LINKEDINJason: https://www.linkedin.com/in/jasontezi/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—Tezi: https://tezi.ai/-For coaching and advising inquire athttps://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(01:55) Meet Max: The AI Agent Replacing Recruiting Busywork(03:16) AI Bias vs Human Bias: Which Is Fairer?(06:08) Human-in-the-Loop: AI Recommends, Humans Decide(07:34) AI Interviews at Top of Funnel: What Works, What Doesn't(11:00) Standing Out in a Crowded AI Recruiting Market(14:26) Sponsors: Ethena & Metaview(17:18) “RCs and Sourcers, Find Something Else”(20:30) The New Grad Opportunity: Alpha in a Tough Market(22:23) “Riding the Elevator Up”: The Resume Pedigree Problem(24:26) How to Spot Resume Riders vs Real Contributors(26:00) 100-Hour Weeks and the 9-9-6 Culture Debate(30:00) “The Best Culture Is Growth”(31:00) Tezi's Culture: Committed to Calm, Team of Adults(34:00) What's Next for Tezi?(34:56) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In this latest installment of AI Corner, Kelli, Nolan and Metaview CEO Siadhal Magos discuss the “Trough of Disillusionment” in enterprise AI adoption, exploring the gap between inflated expectations and practical implementation realities in recruiting workflows. Watch as Siadhal demonstrates Metaview's AI sourcing, showcasing its intuitive, agent-based approach that moves beyond traditional Boolean methods.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH SIADHAL, NOLAN + KELLI ON LINKEDINSiadhal: https://www.linkedin.com/in/siadhal/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—Metaview: https://www.metaview.ai/-For coaching and advising inquire athttps://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(00:35) Why Metaview Built AI Sourcing(02:20) The Vision: Humans and AI Working Together(03:09) Technical Breakthrough: Browser Use and Computer Use(04:41) Beta to GA Launch Story(05:01) Promptless Sourcing Feature(06:36) Sponsor: Metaview(07:58) Demo(26:38) Data Sources and LinkedIn Compliance(28:01) Future: ATS Integration and Multi-Database Search(30:13) What's Coming Next for Metaview(31:29) Product Development Philosophy(32:04) How to Try Metaview Sourcing(32:33) Closing This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

This week, we chat with Rex Woodbury! Rex is the Founder and Managing Partner of Daybreak, an early-stage venture capital firm based in New York. Daybreak is a first-check firm built on the belief that the companies shaping the future will be those improving the lives of the next generation.Before starting Daybreak, Rex was a Partner at Index Ventures, where he invested in consumer technology and the creators building online communities. Beyond investing, Rex is also the writer behind Digital Native, a widely read weekly publication exploring the intersection of technology, culture, and the internet with over 70,000 readers each week.With his unique perspective as both an investor and a storyteller of the digital age, he brings deep insight into how technology continues to shape how we live, work, and connect.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Rex Woodbury: @rex_woodburyDaybreak: @daybreak_fund@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

On today's Dear Heretics segment, Kelli and Nolan analyze why traditional bonus programs fail at early-stage companies, advocating for flexible sprint incentives and spot bonuses over rigid annual structures that create organizational debt.Support our Sponsor:Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—For coaching and advising inquire athttps://kellidragovich.com/—TIMESTAMPS:(00:00) Introduction: The Bonus Program Question(01:04) The Cyclical Wave & Sales Incentives(01:42) Why Early-Stage Companies Struggle(02:46) The Coin-Operating Problem(03:26) The 96% Problem: Legacy & Recruiting Pressure(04:34) You Can't Put the Toothpaste Back(05:30) Equity Over Bonuses(06:09) Inconsistent Application Across Teams(06:43) Walking It Back Is Brutal(08:06) Sponsor: Metaview(09:28) Technical Debt vs People Debt(11:10) Second Order Consequences(12:31) MBOs Are a Fable(12:53) The Solution: Sprint Incentives(14:04) Surprise and Delight: Spot Bonuses(15:08) Discretionary Budgets & Agility(15:54) Final Thoughts: Avoid People Debt(15:59) Outro This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

Welcome back to Trailblazers by Park Rangers Capital!In this week's solo episode, host Erica Wenger shares her hot takes on venture capital the unspoken takes that many in the industry quietly know but rarely say out loud.From fundraising dynamics to investor-founder relationships, Erica unpacks the realities that shape how VC really works behind the scenes beyond the headlines and polished pitch decks.If you've ever wondered what people in venture really think (but don't tweet), this episode is your insider look into the honest, unfiltered side of the industry.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by Rocketreach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo (formerly OpenPhone): Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

Jason James doesn't sugarcoat it: recruiting coordinators and sourcers won't exist in 5 years. In this episode, James (Co-founder and COO of Tezi) sits down with Kelli and Nolan to discuss how to screen 3000 applicants in minutes, why most great resumes just rode the elevator up at hypergrowth companies, and why AI bias audits set a higher standard than humans ever could.Support our Sponsors:Ethena is the compliance training platform built for modern workplaces. Visit goethena.com/heretics and get 10% off your first year.Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH JASON, NOLAN + KELLI ON LINKEDINJason: https://www.linkedin.com/in/jasontezi/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—Tezi: https://tezi.ai/-For coaching and advising inquire athttps://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(01:55) Meet Max - The AI Agent Replacing Recruiting Busywork(03:16) AI Bias vs Human Bias: Which Is Fairer?(06:08) Human-in-the-Loop: AI Recommends, Humans Decide(07:34) What Works, What Doesn't in AI Interviews at Top of Funnel(11:00) Standing Out in a Crowded AI Recruiting Market(14:26) Sponsors: Ethena | Metaview(17:18) “RCs and Sourcers: Find Something Else”(20:30) The New Grad Opportunity(22:23) “Riding the Elevator Up”: The Resume Pedigree Problem(24:26) How to Spot Resume Riders vs Real Contributors(26:00) 100-Hour Weeks and the 9-9-6 Culture Debate(30:00) “The Best Culture Is Growth”(31:00) Tezi's Culture: Committed to Calm, Team of Adults(34:00) What's Next for Tezi (34:56) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

This week, we chat with Avni Barman! Avni is the CEO and Founder of Gen She, a media company and fund empowering a community of over 700,000 women across Instagram, TikTok, a newsletter, a podcast, and a job board. Through Gen She, Avni writes $50K–$100K checks into ventures that directly help their audience rise to the top 1%, driving real impact for the next generation of women leaders.Before launching Gen She, Avni spent over four years in Big Tech as an engineer and product manager — experience that now fuels her mission to unlock the potential of young women in entrepreneurship, tech, venture, and media.Her work bridges empowerment and innovation — creating pathways for women to lead in every corner of tech, venture, and media.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Avni Barman: @avnibarman_Gen She: @gen.she@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

On today's HR Heretics, Kelli and Nolan debate radical workplace transparency: eliminating private Slack messages. They explore tensions between cultural openness, practical communication needs, and effective use of asynchronous tools.Support our Sponsors:Ethena is the compliance training platform built for modern workplaces. Visit goethena.com/heretics and get 10% off your first year.Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(00:13) The “No Private DMs” Rule(01:04) First Reactions: How This Would Actually Work(01:54) The Case for Transparency: Underground Slack Channels Are Toxic(02:35) The Reality Check: Leaders Still Need Private Conversations(03:42) Is Radical Transparency Just Performance Art?(04:20) The Productivity Problem: Slack Surfing vs Getting Work Done(05:11) Creating a “How We Slack” Document with Clear Rules(06:15) Using Public Channels to Develop Holistic Leaders(07:13) The Jensen Huang Model: Why He Doesn't Do One-on-Ones(08:12) Sponsors: Ethena | Metaview(11:34) Hyper-Transparency from the CEO Builds Trust(12:31) It All Comes Down to Judgment(13:11) The Audio Message Revolution: Why Voice Beats Typing(15:20) Good vs Bad Audio Messages: It's About Sender Judgment(16:15) The 10x Pace: Why Traditional Meeting Cadences Don't Work Anymore(17:34) Final Thoughts: Experiment with Your Communication Style(17:46) Outro This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

Oura CEO Tom Hale talks with TITV Host Akash Pasricha about raising $900M at an $11B valuation and the company's AI-driven plans for the future of health tech. We also talk with Brex CEO Pedro Franceschi about the company's "unconstrained ambition" and how they're competing with incumbents. The Information's Stephanie Palazzolo explains the rise of "NeoClouds" and the race to rent out NVIDIA chips. Lastly, we get into AI-powered material science with Radical AI CEO Joseph Krause.Articles discussed on this episode:https://www.theinformation.com/articles/race-rent-nvidia-chips-cloud-intensifiesTITV airs on YouTube, X and LinkedIn at 10AM PT / 1PM ET. Or check us out wherever you get your podcasts.Subscribe to: - The Information on YouTube: https://www.youtube.com/@theinformation4080/?sub_confirmation=1- The Information: https://www.theinformation.com/subscribe_hSign up for the AI Agenda newsletter: https://www.theinformation.com/features/ai-agenda

In this episode of Planning Aces, host Jack Sweeney and resident thought leader Brett Knowles explore how finance leaders are approaching AI's early returns—balancing efficiency, experimentation, and human judgment. CFO Craig Foster of Pax8 discusses how AI enablement is driving measurable productivity gains. CFO David Obstler of Datadog reflects on finding ROI amid rapid innovation and market demand. And CFO Ben Gammell of Brex shares why forecasting still requires human intuition despite data-driven progress. Together, their insights reveal a spectrum of FP&A strategies defining the modern CFO's mindset toward AI adoption and business transformation.Brett Knowles' Key TakeawaysBrett Knowles observes that finance leaders are positioning themselves along a broad continuum—from bold experimentation to cautious skepticism—when it comes to AI in planning. He notes a shift in tone: CFOs are now openly discussing productivity gains and cost efficiency rather than avoiding them. Knowles cautions against overreliance on ROI metrics, emphasizing instead disciplined cost management, pragmatic experimentation, and the evolving role of finance in navigating technology-driven transformation.

In this episode of Planning Aces, host Jack Sweeney and resident thought leader Brett Knowles explore how finance leaders are approaching AI's early returns—balancing efficiency, experimentation, and human judgment. CFO Craig Foster of Pax8 discusses how AI enablement is driving measurable productivity gains. CFO David Obstler of Datadog reflects on finding ROI amid rapid innovation and market demand. And CFO Ben Gammell of Brex shares why forecasting still requires human intuition despite data-driven progress. Together, their insights reveal a spectrum of FP&A strategies defining the modern CFO's mindset toward AI adoption and business transformation. Brett Knowles' Key Takeaways Brett Knowles observes that finance leaders are positioning themselves along a broad continuum—from bold experimentation to cautious skepticism—when it comes to AI in planning. He notes a shift in tone: CFOs are now openly discussing productivity gains and cost efficiency rather than avoiding them. Knowles cautions against overreliance on ROI metrics, emphasizing instead disciplined cost management, pragmatic experimentation, and the evolving role of finance in navigating technology-driven transformation.

For today's essential Heretics 101 feature, Kelli and Nolan talk to Sally Thornton, CEO and Founder of Forshay who offers a candid examination of fractional executive work, exploring trust barriers, adverse selection problems, pricing models, and why consulting acumen matters more than traditional executive experience.Support our Sponsors:Ethena is the compliance training platform built for modern workplaces. Visit goethena.com/heretics and get 10% off your first year.Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH SALLY, NOLAN + KELLI ON LINKEDINSally: https://www.linkedin.com/in/sallythornton/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Forshay: https://forshay.com/-For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(01:46) The Trust Barrier: Why Companies Resist Fractional Work(03:34) The TAM Debate and Market Dynamics Post-COVID(05:14) The Dirty Secret: There's No Such Thing as Fractional Work(06:34) Sponsors: Ethena | Metaview(10:01) Who's Buying and Why Finance Gets It(11:06) Let's Talk Money: The 65/35 Structure and Market Rates(12:30) The Honeymoon Phase: Managing Boundaries and Expectations(14:44) How to Assess Fractional Executives: The 75% Rule(16:31) From Interim to Modular: How the Market Evolved(18:04) The Black Hole Question: Why Nobody's Calling You Back(19:36) Network for Yourself: Nobody's Managing Your Career But You(21:36) How to Sustain 15 Years: Running Experiments & Following Curiosity(22:31) Closing Thoughts: Agents for Executives Don't Yet Exist(23:11) Outro This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

Welcome back to Trailblazers by Park Rangers Capital!In this week's solo episode, host Erica Wenger dives into why every founder should have a manifesto — a clear, written declaration of what they stand for and where they're headed.Erica breaks down three key benefits of writing one and walks you through five actionable steps to get started. She also makes a compelling case for the power of thoughtful, long-form writing — not just as a branding exercise, but as a way to sharpen conviction, attract alignment, and move your mission forward.If you've been waiting for the “perfect moment” to write your manifesto — this is your sign to just start.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by Rocketreach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo (formerly OpenPhone): Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

For today's essential Heretics 101 feature, Kelli and Nolan talk to Culture Amp CEO Didier Elzinga, revealing data-driven insights on building culture-first companies, balancing psychological safety with accountability, and prioritizing growth as engagement's foundation.Support our Sponsors:Ethena is the compliance training platform built for modern workplaces. Visit goethena.com/heretics and get 10% off your first year.Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.KEEP UP WITH DIDIER, NOLAN + KELLI ON LINKEDINDidier: https://www.linkedin.com/in/didierelzinga/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Culture Amp: https://www.cultureamp.com/For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(00:01) The Origin Story: Why People and Culture Matter Most(00:02) What Makes a Culture-First Company?(00:03) The Coherency Matrix: Trust vs. Mission Orientation(00:04) Why Top Performance is Unstable (And That's OK)(00:05) The Data That Never Changes: Growth Drives Everything(00:06) Shocking Data: Leaders Matter More Than Managers(00:07) The Heretical Answer: Stop Trying to Convince People(00:08) Gender Gap Data: How Structured Reviews Change Everything(00:09) Sponsors: Ethena | Metaview(00:13) Esther Perel's Challenge: Leaders Don't Know How to Say No(00:14) The Engagement Survey Mistake Most CPOs Make(00:15) “Feedback Is Not a Gift, It's a Workout”(00:16) Running Culture Amp: Vulnerability and Accountability(00:18) Growth Philosophy: Betting on Internal Potential(00:19) You Can't Be Everything for Everyone(00:20) The Most Important Leadership Skill(00:22) The Origin Story Framework That Closes Deals(00:23) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

Josh Liburdi, Principal Engineer of Security Operations at DoorDash, joins Maxime Lamothe-Brassard, LimaCharlie CEO / Founder, to talk about building the Strelka file scanning system.As a security engineer who works in security operations (prevention, detection, and response), Josh has more than a decade of industry experience and has worked at several diverse organizations, including Brex, Target, and CrowdStrike.He also presents at information security conferences (BSides NYC & SF, SANS, fwd:cloudsec), is a published author (Bluenomicon from Splunk, Huntpedia from Sqrrl), and is active in the open source security community with contributions to many projects, including Substation at Brex (creator), Strelka at Target (creator), and the Zeek network analysis framework.Join Defender Fridays, live every Friday, to discuss the dynamic world of information security in a collaborative space with seasoned professionals. Become part of the LimaCharlie Community. Learn more about LimaCharlie at limacharlie.io.

For today's essential Heretics 101 feature, Kelli and Nolan talk to Coinbase Chief People Officer LJ Brock reveals how the company's mission-first philosophy, refusal to negotiate salaries, and rigorous talent density standards challenge conventional HR orthodoxy.Support our Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.Ethena is the compliance training platform built for modern workplaces. Visit goethena.com/heretics and get 10% off your first year.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(00:46) Banning Politics at Work(02:29) Backlash and Reality: “You'll Never Work Again”(04:32) The Near-Death Moment(05:22) How Coinbase Creates Radical Ideas(06:34) Talent Density: The Future of Hiring Standards(09:04) CEO Approval for Every Hire(09:14) Real-Time Feedback: Eliminating Manager Bias(11:33) Performance Systems That Don't Suck(13:34) Sponsors: Ethena | Planful(16:43) Work Trials(15:37) Sponsor: Metaview(16:43) Work Trials: The 12-Week Internship Strategy(19:49) Single Pay Target(21:00)Executive Alignment on No Negotiation(22:03) Stock Grants: From Four Years to One Year(23:17) Building the Next Generation of CHROs(26:40) Closing This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

This week, we chat with Maya Bakhai! Maya Bakhai is the founder of Spice Capital, a first-yes fund investing at pre-seed and seed. Maya's Fund II is a $25M Fund that will invest in ~40 companies with check sizes ranging from $250k-$750k. Spice Capital has over 50 companies in the portfolio including Beehiiv, MUBI, Prosper Health, Hype, Skej, and more.In the last 8 years, Maya has backed 100+ founders.. Prior to starting Spice Capital in 2021, she ran venture investments for Kevin Durant at Thirty Five Ventures where she invested in multiple now-unicorns including: Hugging Face, Robinhood, Skydio, Mercury, Whoop, Rubrik, and Underdog Fantasy. She has a B.S. in Finance and Data Science from NYU. In 2023, she was recognized for her investing in Forbes 30 under 30's Venture Capital list.Maya is based in NYC. Fun fact: In a past life, she produced a sold out off-broadway musical- “Aliens Coming”, a narrative podcast -“Illuminati Interns” and an award-winning web series called “Freelance”.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by RocketReach, Gusto, OpenPhone & Athena.RocketReach: rocketreach.co/trailblazersGusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Maya Bakhai: @MayaBakhaiSpice Capital: @spice_cap@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

On today's HR Heretics, Kelli and Nolan deliver candid analysis of H1B visa policy disruptions impacting tech hiring, then recap their Confluent People Team offsite with Colleen McCreary, featuring contrarian HR perspectives on compensation equity, organizational beliefs, and fostering intellectual disagreement.Support our Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.Ethena is the compliance training platform built for modern workplaces. Visit goethena.com/heretics and get 10% off your first year.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(00:40) H1B Visa Impact on Tech(11:48) Sponsors: Ethena | Planful(15:25) Confluent People Team Offsite Recap(20:37) Sponsor: Metaview(22:27) Contrarian HR Beliefs & Organizational Leadership(27:34) Fashion Roast: Is Silicon Valley Dressing Up?(29:08) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In this episode, Sasha Orloff sits down with Jason Mok, VP & GM of Startups at Brex, about the company's evolution from credit cards to a comprehensive financial platform and their new partnership with Puzzle to offer "one-click accounting" that automatically sets up bookkeeping for startups during Brex onboarding, eliminating the friction that typically delays founders from getting proper financial infrastructure in place from day one. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Puzzle

On today's Dear Heretics segment, Kelli and Nolan deliver candid, practical advice for Chief People Officers navigating their critical first 90 days, featuring real-world insights on building stakeholder trust, executing quick wins, and establishing strategic organizational influence.Support our Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.Ethena is the compliance training platform built for modern workplaces. Visit goethena.com/heretics and get 10% off your first year.KEEP UP WITH NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(01:13) Three Core Goals for New CPOs(01:41) Common Fail States to Avoid(02:03) Over-Communicating with Your CEO(02:23) Building Executive Relationships Beyond One-on-Ones(02:58) Getting to the Ground Floor: The Modern Executive Approach(03:19) The Colleen McCreary Method: 100 One-on-Ones in 90 Days(04:26) Quick Wins and Board Relationship Strategy(04:44) Four-Pillar Framework in Action(05:34) Pre-Start Transparency: Setting Expectations Early(06:40) The Four Pillars: Listen, Execute, Strategize, Build(08:18) The Brutal Reality: 3X Speed for Three Months(09:15) Sprint vs Marathon: Managing Energy and Family Expectations(09:58) Reframing “S**t Shows” as Solvable Problems(11:22) The Critical Importance of In-Person Time(12:13) Sponsors: Ethena | Planful(15:22) Building on Company Strengths vs Starting from Scratch(16:31) Team Building Strategy: Know Before You Walk In(17:47) Making “Unnatural” Efforts for Face-Time(18:33) Build Your Scaffolding or Die: The Team Priority(20:14) Ditch HR Speak: Talking Business, Not Corporate Vernacular(21:47) CEO Shadowing: What It Really Means(23:00) Real Partnership: Daily Communication and Quick Feedback Loops(23:59) Sponsor: Metaview(25:18) The Bait-and-Switch Problem in Executive Hiring(27:10) Market Reality: Nine-Month Average Tenure Crisis(29:21) Board Relationships and Air Cover Strategy(30:10) Building Your Narrative: Board Meeting Preparation(31:41) Documentation Strategy: Journaling and Whiteboarding(32:09) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In the early days of a startup, forecasting isn't about nailing the numbers, it's about setting the course. In this episode, the world's most interesting CFO describes the art of “Cowboy forecasting” and how this back-of-the-envelope model can be far more valuable than a complex simulation. Kevin Drost started his career as a musician and talent scout for Sony before becoming the chief strategy officer of the music gear marketplace Reverb. Now, as the CFO of New Era ADR, he explains how the company is disrupting the notoriously expensive legal industry by replacing the billable hour with flat fees, and making dispute resolution faster and more predictable for businesses. The conversation also covers why simplicity often beats complexity in financial modeling, how a hands-on understanding of the product and customer builds real financial confidence, and how finance teams can empower every employee to understand and drive the business.—LINKS:Kevin Drost on LinkedIn: https://www.linkedin.com/in/kevindrostNew Era ADR: https://www.neweraadr.comCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Secrets to Scaling a Marketplace Business with Jack Greco, VC and Co-founder of ACV Auctions — —TIMESTAMPS:(00:00) Preview and Intro(02:40) Sponsor – Aleph | RightRev | Navan(07:18) Kevin's Music Background & A&R at Sony(12:09) Record Labels Versus Venture Capital(17:01) Sponsor – Rillet | Pulley | Brex(20:53) Finding Motivation After Success(21:34) Building Reverb & the Etsy Acquisition(25:33) Stacking Skillsets & Interests(27:11) Cowboy Forecasting at Reverb(32:01) The Importance of Simplicity in Forecasting in the Early Stages(35:46) The Art and Science of Making Estimated Guesses(41:42) Building Firsthand Customer & Product Knowledge(45:36) Teaching Finance Across the Company(50:44) New Era ADR & Legal Industry Disruption(57:35) Legal Strategy Versus Financial Strategy(1:01:30) How New Era Gets Parties To Use the Platform(1:05:27) Other White Hot Use Cases for New Era ADR(1:09:25) The Long Ass Lightning Round: Kevin's Biggest Mistake(1:12:41) Advice to a Younger Self(1:14:01) Finance Software Stack(1:15:21) Life as an A&R Rep—SPONSORS:Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalized demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metrics#CowboyForecasting #FinanceLeader #StartupFinance #LegalTech #StartupForecasting This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

#285 Creative Strategy | In this episode, Dave is joined by Pranav Piyush, Founder & CEO of Paramark, a measurement platform helping B2B and B2C companies run smarter marketing experiments. Pranav is known for turning strategy documents into repeatable creative processes that generate campaigns, ads, and content tied directly to a company's story.Dave and Pranav cover:How to translate your company narrative into concrete marketing campaigns and creative hooks across channelsWhy creative output (not measurement) is the biggest bottleneck for most B2B marketing teams todayThe frameworks like category entry points, jobs-to-be-done, and behavioral psychology that help marketers spark fresh, testable campaign ideas month after monthYou can expect a practical, example-filled conversation on turning strategy into execution and building a creative engine that never runs dry.Timestamps(00:00) - – Intro and audience roll call (05:09) - – Why narratives often get stuck in a Google Doc (08:09) - – Foundational docs you need before creating campaigns (13:09) - – Category entry points and jobs-to-be-done explained (17:09) - – How to feed company inputs into AI tools (23:09) - – Generating ad campaign ideas with real examples (25:09) - – Using analogies (like basketball) to explain complex concepts (29:54) - – Where AI falls short (and why human judgment matters) (32:54) - – Mining sales call transcripts for campaign hooks (36:54) - – Turning customer objections into marketing messages (40:54) - – Repurposing podcasts, presentations, and blog posts into new formats (44:54) - – Systemizing idea generation for repeatable output (48:54) - – Closing thoughts and audience Q&A Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5

This week, we chat with Katie Stanton!Katie is the Founder and General Partner of Moxxie Ventures. Katie is an investor, operator, board member, and proud mom of three kids and two “poorly-trained” dogs. She has built her career leading teams at Yahoo, Google, Twitter, and Color, and also served in the Obama White House and Clinton State Department.As Founder and Managing Partner of Moxxie Ventures, Katie backs entrepreneurs tackling hard problems that improve life, work, and the planet. She was also a Founding Partner of #Angels and has invested in over 50 early-stage companies including Airtable, Coinbase, Cameo, Carta, and Modern Fertility.Katie currently serves on the Boards of Vivendi and Yahoo and previously served on the Board of Time Inc. Her career has been defined by a commitment to brilliant people, bold ideas, and building a better future.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by Gusto, OpenPhone & Athena.Gusto: gusto.com/trailblazersQuo: Quo.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Katie Stanton: @katies@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

In this episode of HR Heretics, Nolan talks to Immigration attorney Nicole Gunara (Manifest Law) who analyzes the new $100,000 H-1B policy that sparked rapid industry adaptation across Silicon Valley, breaking down how this strategic shift creates different advantages for big tech versus startups while driving companies to explore innovative alternative visa pathways.Support our Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Check it out: https://www.metaview.ai/heretics* Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.* Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.* It only takes minutes to get up and running.Ethena is the compliance training platform built for modern workplaces. Visit goethena.com/heretics and get 10% off your first year.KEEP UP WITH NICOLE, NOLAN + KELLI ON LINKEDINNicole: https://www.linkedin.com/in/ngunara10/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Manifest Law: https://manifestlaw.com/Gary Tan's LinkedIn post: A $100K H1B fee won't bother big tech…For coaching and advising inquire at https://kellidragovich.com/—TIMESTAMPS:(00:00) Intro(01:51) What Happened Friday Night: The $100K H-1B Bombshell(02:53) Monday Reality Check: What We Actually Know(04:16) Clear vs. Unclear: Exemptions and Renewal Definitions(07:49) Sponsors: Ethena | Planful(10:58) Crisis Response Strategy: Audit, Pause, and Pivot(15:56) The Alphabet Soup: Alternative Visa Pathways(21:19) Sponsor: Metaview(23:08) The O-1 Opportunity: 94.5% Approval Rates Explained(24:43) The Startup Dilemma: Gary Tan vs. Big Tech Advantage(28:57) Strategic or Chaotic? The Department of Labor Clue(30:13) America's STEM Pipeline Problem: The Real Policy Driver(32:21) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

In a world increasingly dominated by software and automation, how vital are human relationships in banking and finance? In this episode, CJ sits down with Meghan McKenna, founder of Females in Finance (FIF) and a seasoned banker with experience at JPMorgan, HSBC, and Stifel, to explore how trusted connections continue to drive success. As a community builder and banker, Meghan has a unique perspective on the intersection of human connection and capital markets. She explains the philosophy behind her community, which is based on generosity and genuine connection rather than a transactional mindset, and how this has become her competitive advantage. The conversation also covers sales as an essential leadership skill, the rise of the modular banking stack, changes in private credit, the evolving ERP landscape, how a personal touch proved invaluable during the SVB crisis, and career lessons Meghan learned along the way.—LINKS:Meghan McKenna on LinkedIn: https://www.linkedin.com/in/meghan-curtin-mckenna-%F0%9F%94%A5-66a5022b/FIF Collective: https://www.fifcollective.comMeghan McKenna email: meghan@fifcollective.coCJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comRELATED EPISODES:Venture Debt for Growth With Ruslan Sergeyev of Hercules Capital — The One Use Case for Venture Debt That Most Founders Never Think About — —TIMESTAMPS:(00:00) Preview and Intro(02:30) Sponsor – RightRev | Navan | Rillet(06:41) Connecting People as a Skill(08:03) Sales as an Essential Leadership Skill(12:07) The Power of In-Person Community & Events(14:39) FIF's Ideal Customer Profile(15:42) Sponsor – Pulley | Brex | Aleph(20:05) The Evolution of the Banking Ecosystem(22:00) Modular Banking Stacks and Fintech Challengers(24:37) The Rise of Private Credit(27:32) Banks Adapting to Companies That Stay Private Longer(30:06) Fintechs vs. Traditional Banks(31:54) Current Trends in AI and ERP in Finance(35:07) Importance of Human Relationships When Software Fails(36:09) Reflecting on the SVB Bank Run & Facing New Risks in Tech(37:59) Building a Personal Brand in Finance(39:42) Community Spirit, Giving Back, & Sharing Your Network(43:25) Meghan's Early Career and Mentors(46:15) Long-Ass Lightning Round: Staying Too Long in a Role(47:49) Advice to Younger Self(48:24) A Memorable Deal & Client Story(50:07) Wrap—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/run#FemalesInFinance #FinanceLeadership #BankingInnovation #Networking #FinanceCommunity This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

#284 Brand | Dave sits down with Ari Yablok, Head of Brand at Island, to share his approach to creating a brand in the cybersecurity space. Ari shares his journey from agency life to leading the brand narrative at Island, where he helped build the concept of the "enterprise browser."Dave and Ari Cover:The key differences between category creation and strategic positioning, and why it matters for B2B marketersThe steps to building a brand story that resonates with both your internal team and your target audienceHow focusing on the last 20% of branding efforts can elevate your company above the competitionTimestamps(00:00) - - Intro to Ari (04:33) - - Rapidly Growing Enterprise Browser Company Secures $375M in Series D Funding (08:42) - - SEO Strategy vs Branding (14:09) - - How Brand is an Art and a Science (19:24) - - Challenges in Cybersecurity Branding (21:08) - - Early Stage Marketing (29:48) - - Cognitive Behavioral Branding (34:57) - - How Ari Manages Projects with the Brand Team (37:07) - - Comfortable vs. Uncomfortable Approaches to Brand Strategy (41:25) - - What Founders Really Want to Do (46:31) - - Balancing the Day-to-Day with Visionary Goals Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5

In 2018, Brex made a defining decision: rather than rely on middleware providers like Stripe or Marqeta, it built its own payments infrastructure from the ground up. That move, Ben Gammell tells us, gave the company a direct integration with MasterCard and the ability to issue corporate cards in “over 50 plus local currencies.” The choice, he explains, was born of necessity at the time but has since become a structural advantage, offering customers greater control and global reach.That same principle of intentional investment extends to Brex's software strategy. The company designs its expense management platform to meet the demands of sophisticated, high-growth businesses such as Arm and Anthropic. The result, Gammell tells us, is a solution that not only competes with legacy providers like Concur but also improves accessibility for smaller firms “with aspirations of being the next DoorDash or Coinbase.”Partnerships further expand the ecosystem. Because Brex controls its processing stack internally, it can integrate with best-of-breed solutions—Navan in travel, Zip and Coupa in procurement—delivering the breadth that global enterprises require while keeping Brex at the center of the transaction.Looking outward, the company recently began expanding into Europe. Gammell tells us the first priority is to better serve U.S. multinationals with operations abroad. Only later will Brex pursue wholly foreign clients. Still, he emphasizes discipline: the U.S. remains “the largest market by a country mile,” and maintaining focus there is key to balancing growth ambitions with profitability and investor confidence.

Returning guest Bryan Power (Head of People, Nextdoor) talk about AI workplace adoption, contrasting executives who avoid AI as time-consuming with his dedicated approach of treating AI as teammates, scheduling one-on-ones with custom GPTs, and transforming workflows.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!Ethena is the compliance training platform built for modern workplaces. Visit goethena.com/heretics and get 10% off your first year.KEEP UP WITH BRYAN, NOLAN + KELLI ON LINKEDINBryan: https://www.linkedin.com/in/bryanpower/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Nextdoor: https://nextdoor.com—TIMESTAMPS:(00:00) Intro(01:00) The Tinkerer vs. The Resisters(03:00) The AI Bubble and Workplace Resistance(05:00) Project Neighbor: Nextdoor's AI Initiative(07:00) Case Study: Building AI Training with ChatGPT(09:00) Mental Model Shift: AI as Teammate, Not Tool(10:00) Scheduling One-on-Ones with Custom GPTs(10:51) Ad Break - Athena & Planful Sponsors(14:01) Executive Offsite Planning: AI in Action(16:00) The Onboarding Problem: Context and Custom GPTs(18:00) Compensation GPT: Domain-Specific AI Applications(21:00) Output and Velocity: Gamma and Slide Creation(22:43) Ad Break - Metaview Sponsor(24:37) Optional or Essential: The Future of AI Adoption(26:00) The Mass Extinction Event for Knowledge Workers(30:00) Creating Permission to Tinker(32:00) Restructuring Executive Time for AI(34:00) Corporate Lingo Roast(44:08) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

The venture capital landscape is evolving, and a founder's choice of fund size and partner could make or break their business. In this episode, CJ sits down with Kyle Harrison, General Partner at Contrary and writer of the Substack Investing 101, to make sense of the changing incentives and power dynamics in the field of venture capital. He explains how capital agglomerators and cottage keepers are playing dramatically different games, how the ethics of backing competitors have changed since the advent of AI, why a fund's size is its strategy, and what the potential pitfalls of dilution could be for founders. The conversation also covers why the line between hype and tangible business value in AI is so blurry, the role of narrative as an economic driver, and why the most valuable thing a VC can offer might just be "borrowed credibility.”—LINKS:Kyle Harrison on LinkedIn: https://www.linkedin.com/in/kyle-harrison-9274b278/Contrary: https://www.contrary.comInvesting 101: CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.comLINKS MENTIONED:* “The Unholy Trinity of Venture Capital”: * “The Horse, The Jockey, or The Whole Race?” * Endowment Eddie on X (@endowment_eddie): https://x.com/endowment_eddie* “Institutionalized Belief In The Greater Fool”: * “The Unbundling of Venture Capital”: * “The Productization of Venture Capital”: https://kwharrison13.com/essays/the-productization-of-venture-capital—TIMESTAMPS:(00:00) Preview and Intro(02:23) Sponsor – Navan | Rillet | Pulley(07:13) VC Models: Cottage Keepers Versus Capital Agglomerators(11:16) Balancing Taking On Money and Finding Great Investments(16:35) Sponsor – Brex | Aleph | RightRev(20:54) Founder-Friendliness: The Ethics of Backing Competitors(26:33) When Fund Size Sabotages Outcomes(32:32) The Sins of Omission Versus Commission(36:02) The Dilution Trap for Operators in Venture-Backed Companies(38:17) Underestimating the Magnitude of the Outcomes(40:35) AI Hype, Valuation, and Real Business Impact(45:37) Market Psychology: Narrative and Story As Economic Drivers(48:21) Valuation: Cursor and Windsurf(52:50) The Unbundling of Venture Capital: What Founders Really Hire VCs For(1:01:47) Things To Consider When Choosing a VC(1:04:35) FTX Lessons & Compounding Growth(1:10:02) Kyle's Predictions for the Future of VC—SPONSORS:Navan is the all-in-one travel and expense solution that can give you access to exclusive, proprietary Nasdaq-validated data that reveals what's happening with corporate travel investments. See the Navan Business Travel Index at https://navan.com/bti.Rillet is the AI-native ERP modern finance teams are switching to because it's faster, simpler, and 100% built for how teams operate today. See how fast your team can move. Book a demo at https://www.rillet.com/metrics.Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics.Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at https://www.brex.com/metricsAleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.##VentureCapital #VC #Startups #Founder #FundSize This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

This week, we chat with Ali Kriegsman! Ali is a writer, entrepreneur, and business strategist whose work lives at the intersection of brand building, storytelling, and sales. At just 24, she co-founded Bulletin, a retail technology company that reimagined how premium brands and retailers connect. Bulletin went on to be acquired by Emerald [NYSE:EEX], the largest B2B events company in the United States, in a $10 million deal.Since then, Ali has helped founders and companies raise more than $20 million in venture funding, secure profitable exits, and close major sponsorship and partnership deals. She's also the author of How to Build a Goddamn Empire, and her most recent fiction project, The Raise, which pushes the boundaries of traditional publishing by blending storytelling with cinematic, social, and direct-to-consumer elements to create an immersive brand experience.Ali has been recognized as a Forbes ‘30 Under 30' honoree and one of Fast Company's ‘Most Creative People in Business,' and her work has been featured in The New York Times, The Wall Street Journal, Entrepreneur, Refinery29, The Today Show, and more✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by Gusto, OpenPhone & Athena.Gusto: gusto.com/trailblazersOpenPhone: openphone.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!Ali Kriegsman: @alikriegs@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger

For today's essential Heretics 101 feature, Kelli and Nolan talk to Katelin Holloway, Founding Partner of Seven Seven Six. Katelin argues HR professionals possess essential early-stage investing skills, and advocates their transition from support roles to decision-making positions through founder relationship-building strategies.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH KATELIN, NOLAN + KELLI ON LINKEDINKatelin: https://www.linkedin.com/in/katelinholloway/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS: Seven Seven Six: http://sevensevensix.com—TIMESTAMPS:(00:00) Intro(01:27) How HR "Found" Katelin: The Accidental Career Path(02:02) Pixar University: Learning from World-Class People Operations(03:16) Meeting Alexis Ohanian: The Reddit Turnaround Story(04:12) When Employees Refused to Wear Company Swag(04:43) Why Hard Challenges Build Deeper Professional Bonds(05:42) From Boardroom to Back Room: The VC Industry Problem(07:24) Why Early-Stage Investing IS People Work(08:52) The "Talent Partner" Problem: Wasted Potential in VC(09:40) Sponsors: Planful | Metaview(12:03) The Marc Andreessen Challenge: Selection vs. Support(13:23) Platform Shifts Are Disrupting Venture Capital(14:07) Product and People First: 776's Different Approach(15:30) The Tactical Playbook: How to Break Into Venture(15:49) Build Founder Relationships, Not VC Relationships(16:22) The "How Can I Help?" Problem: Why Most VCs Fail Founders(17:39) From Advisor to Angel: Getting Equity Without Cash(18:28) The Golden Rule: Genuine Help Must Come First(20:06) Ed Catmull's 5-Year Rule: Knowing When to Leap(21:57) Why the Smartest People Never "Figure It Out"(22:26) Closing: Building the Future of Venture Capital This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

AGENDA: [00:05] Musk's $1 Trillion Pay Package: The Breakdown? [00:15] Scale, Windsurf: Are Founders Just Mercenaries Chasing Cash Today? [00:21] Ramp at $1B ARR, Brex at $700M — Is AI Causing All Boats To Rise? [00:26] Sierra at $100M ARR Worth $10B — Bubble or Brilliant Bet? [00:30] Kleiner Perkins Invests $100M into Anthropic at $183BN… WTF? [00:36] $10B in OpenAI Secondaries — What Happens When 1,000 New Millionaires Hit SF? [00:40] Anthropic Pays $1.5B to Authors — Fair Deal or Pure Piracy? [00:44] Why Did ASML Just Invest into Mistral at $14BN? [00:52] Atlassian Buys the Browser Company for $610M — Genius Move or Panic Buy? [01:18] IRL CEO Arrested for Fraud: Is More To Come?  

For today's essential Heretics 101 feature, Kelli and Nolan talk to Iain Roberts, Airbnb's Global Head of Employee Experience and discuss his transition from IDEO designer to Airbnb's CHRO, exploring how design thinking principles reshape organizational structure, collaborative leadership, and workplace policies in opposition to traditional HR practices.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI platform built for recruiting. Our suite of AI agents work across your hiring process to save time, boost decision quality, and elevate the candidate experience.Learn why team builders at 3,000+ cutting-edge companies like Brex, Deel, and Quora can't live without Metaview.It only takes minutes to get up and running. Check it out!KEEP UP WITH IAIN, NOLAN + KELLI ON LINKEDINIain: https://www.linkedin.com/in/robertsiainNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINKS:Airbnb: http://airbnb.com/—TIMESTAMPS:(00:00) Intro(01:08) "Everything Needs to be Designed" Philosophy(02:48) Founder Mode: Leadership Through Collaboration(05:50) The One Roadmap Strategy(08:04) Prototyping Human Experiences(12:14) Sponsors: Planful | Metaview(14:42) Live and Work Anywhere: The Contrarian Bet(18:12) Talent Strategy & Future of Work(20:19) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

Welcome to the very first episode of Trailblazers by Park Rangers Capital!In our very first episode, our host, Erica Wenger sets the stage for what's ahead — redefining what it means to be a trailblazer and introducing the bold, unconventional voices you'll hear on this show.This is the starting point for conversations with contrarian tech leaders who challenge the norm, break barriers, and build in unexpected ways.✨ This episode is presented by Brex.Brex: brex.com/trailblazerspodThis episode is supported by Gusto, OpenPhone & Athena.Gusto: gusto.com/trailblazersOpenPhone: openphone.com/trailblazersAthena: athenago.me/Erica-WengerFollow Us!@thetrailblazerspod: Instagram, YouTube, TikTokErica Wenger: @erica_wenger