What nobody tells engineers about becoming a CEO | Jay Kreps (Co-founder and CEO, Confluent)

Jay Kreps is the co-founder and CEO of Confluent, the company built around Apache Kafka — the open-source data streaming platform he originally built while at LinkedIn. In this conversation, Jay shares his full journey: how Confluent grew from a scrappy group of engineers with no go-to-market experience into a publicly traded enterprise software company. He makes the case that the difference between what a company can do, and what it must do, is one of the most underrated building levers; illustrated through his years spent pushing Confluent towards a cloud product, in the face of widespread opposition. In this episode, we discuss: Why moving from software engineer to CEO requires almost an entirely new skillset The product marketing pyramid Jay built to explain Kafka to the world How Confluent bludgeoned its way to a cloud-first business when the early product was “embarrassing” The critical difference between what a company can do and what it must do What keeps scaling companies from becoming "Chipotle” References: Amazon Web Services: https://aws.amazon.com/ Apache Kafka: https://kafka.apache.org/ Benchmark: https://www.benchmark.com/ Confluent: https://www.confluent.io/ Jun Rao: https://www.linkedin.com/in/junrao LinkedIn: https://www.linkedin.com/ McKinsey & Company: https://www.mckinsey.com/ MySpace: https://www.myspace.com/ Neha Narkhede: https://www.linkedin.com/in/nehanarkhede Oracle: https://www.oracle.com/ Red Hat: https://www.redhat.com/ Snowflake: https://www.snowflake.com/ Where to find Jay: LinkedIn: https://www.linkedin.com/in/jaykreps/ Twitter/X: https://x.com/jaykreps Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 01:18 Making the leap from engineer to CEO 03:33 The 80% rule: what a CEO actually needs to know 04:54 Scaling different business disciplines 09:31 How Confluent’s story began in LinkedIn 12:13 The growing need for scalable data tech 13:37 What the early Kafka product looked like 16:38 Kafka’s underwhelming open-source launch 18:38 The blog post that accelerated Kafka’s adoption 20:16 Why so many marketing messages fail 28:08 The decision to build Confluent 34:24 Planning to fundraise before building the product 39:19 Confluent’s early years: Tough product decisions 47:07 The underrated growth lever question for companies 55:46 Why founder optimism is an overrated trait 1:00:29 What should founders give up as they scale? 1:02:47 Why people become trapped in a failure mindset 1:08:33 The Chipotle problem: Losing excellence at scale

In the latest episode of Executive Function, Brett is joined by Jeremy Epling, CPO of security and compliance platform Vanta. Jeremy details his career journey, unpacking what it took to make the jump from tenured Microsoft executive to startup CPO. He also shares hard-won insights: how to maintain shipping velocity as headcount explodes, how to manage performance without the safety net of big-company process, and what it means to run a product org where the buck truly stops with you. In today's episode, we discuss: The mindset shift that made Jeremy's transition to startup CPO work Why it’s essential for the CPO to stay connected to details The rule to ensure teams ship fast while growing quickly Why rigid hierarchies derail quality decision-making How Jeremy uses open office hours for the entire company References: Christina Cacioppo: https://www.linkedin.com/in/ccacioppo/ Dropbox: https://www.dropbox.com GitHub: https://www.github.com Ironclad: https://www.ironcladapp.com Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ Lovable: https://lovable.dev Microsoft: https://www.microsoft.com Nat Friedman: https://www.linkedin.com/in/natfriedman/ NVIDIA: https://www.nvidia.com Span: https://www.span.app/ v0: https://v0.dev Vanta: https://www.vanta.com Where to find Jeremy: LinkedIn: https://www.linkedin.com/in/jeremy-epling-j40/ Twitter/X: https://x.com/jeremy_epling Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Introduction 00:09 Why most big-tech executives fail at startups 05:38 Great product leaders stay in the details 09:21 The biggest mindset shift from VP to CPO 16:24 Revenue and product teams are always at odds 18:00 The key to a quality CPO and CRO relationship 23:21 Stop making your team fetch rocks 25:54 Who ultimately oversees the quality bar? 32:27 Why rigid hierarchies kill great companies 36:38 How to leave actionable, detailed feedback 38:55 Great CPOs should avoid comfort metrics 47:27 A glimpse into Jeremy’s working week 49:07 The case for weekly 1:1s 55:13 Why ICs are the unsung heroes of a company 58:25 Jeremy’s most formative career moments 1:07:55 The hardest skills Jeremy had to learn 1:09:31 Why great managers know when to push

Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives per year. In this episode, Keller breaks down his extreme hiring philosophy that has powered Zipline for over a decade. He also walks through Zipline’s full origin story: from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown. In today's episode, we discuss: Why Zipline hires teenagers over PhDs Why the best startup employees are "heat-seeking missiles for pain" The 5 leadership attributes Zipline has never shared publicly The brutal firing advice that shaped Keller’s leadership How Rwanda’s health minister changed Zipline’s trajectory References: Airbnb: https://www.airbnb.com Alfred Lin: https://www.linkedin.com/in/linalfred/ Amazon: https://www.amazon.com Apple: https://www.apple.com Brian Chesky: https://www.linkedin.com/in/brianchesky/ Cleveland Clinic: https://my.clevelandclinic.org Netflix: https://www.netflix.com Paul Kagame: https://www.linkedin.com/in/paulkagame/ Reflect Orbital: https://www.reflectorbital.com Sequoia Capital: https://www.sequoiacapital.com SpaceX: https://www.spacex.com Sphero: https://www.sphero.com Tesla: https://www.tesla.com University of Washington: https://www.washington.edu Walmart: https://www.walmart.com Zipline: https://www.zipline.com Where to find Keller: LinkedIn: https://www.linkedin.com/in/kellerrc/ Twitter/X: https://x.com/Keller Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Introduction 02:11 Why Zipline doesn't hire for experience 06:04 Are founders born or made? 07:37 Why Zipline hires 17-year-olds over PhDs 17:03 The employees Zipline doesn't want 18:53 The ultimate startup hire is a "heat-seeking missile" 20:36 Why blind references are a non-negotiable 23:07 Can candidates admit when they screwed up? 30:10 Zipline's secret leadership playbook 35:16 Why you should always fire quickly 36:26 The early vision for Zipline 39:48 How Zipline almost died - twice 44:55 From toy robots to drone delivery: Zipline's pivot 51:35 How Rwanda's health minister changed everything 57:10 Why Zipline's launch was a "complete disaster" 1:04:05 Scaling from 1 hospital to 5000 1:05:17 The 10x hardware cost rule every founder should know

Chris Degnan was the first sales hire at Snowflake and spent 11 years scaling the company from zero to $3.5 billion in revenue as its CRO, working alongside four different CEOs and learning from each one. In this episode, Chris breaks down what it actually takes to scale an enterprise sales organization, why MEDDIC is the methodology every founder should know, and what working under Frank Slootman taught him about firing fast, taking feedback and finding the fakers in your team. In today's episode, we discuss: What the CRO job looks like at $10M vs. $1B+ Why sales leaders must know how to sell the product themselves The MEDDIC methodology and why it's a founder's best insurance policy How to find the fakers, manage-uppers and passengers in your org What Frank Slootman got right — and wrong — about scaling Snowflake Why most AI companies will face a go-to-market reckoning References: Amazon: https://www.amazon.com/ Bob Muglia: https://www.linkedin.com/in/bob-muglia-714ba592/ Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/ Christian Kleinerman: https://www.linkedin.com/in/christian-kleinerman-a973102/ Denise Persson: https://www.linkedin.com/in/denisepersson/ Dell: https://www.dell.com/ Frank Slootman: https://www.linkedin.com/in/frankslootman/ John McMahon: https://www.linkedin.com/in/johnmcmahon1/ Michael Scarpelli: https://www.linkedin.com/in/michael-scarpelli-1b289b9/ Microsoft: https://www.microsoft.com/ Oracle: https://www.oracle.com/ Salesforce: https://www.salesforce.com/ Snowflake: https://www.snowflake.com/ Sridhar Ramaswamy: https://www.linkedin.com/in/sridhar-ramaswamy/ Stanford Graduate School of Business: https://www.gsb.stanford.edu/ Where to find Chris: LinkedIn: https://www.linkedin.com/in/chris-degnan/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 What is the job of a CRO? 01:12 What excellence looks like at different revenue stages 02:59 Sales leaders need to know how to sell the product 04:52 The hardest skill leaders have to learn 08:17 You need to stay open to feedback - at all levels 14:01 Sales, segmentation, and international expansion 16:17 Why MEDDIC is the foundation for every sales org 20:32 The metrics that actually matter 22:56 A week in the life of a CRO at scale 28:32 Navigating compensation at a GTM organization 31:45 What technical CEOs get wrong about GTM 36:01 The role of hunger in great sales leaders 40:35 What makes an exceptional IC sales rep 46:41 Dysfunctional vs. high-performing executive teams 48:01 Chris' most impactful decisions at Snowflake 49:53 "When there's doubt, there's no doubt" 54:49 Learning from world-class leaders

Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one of the most unconventional paths to the C-suite in tech. In this episode, she unpacks why early revenue hires fail, what separates a true CRO from a VP of Sales, and why she believes fewer than 10% of current CROs will thrive by 2028. In today's episode, we discuss: Why early revenue hires fail What a top 1% CRO actually does The scaling mistake Stevie made by copying Twilio's playbook at Vanta Why Vanta remains 100% sales-led at every segment AI vs. humans in go-to-market References: Cursor: https://cursor.sh/ Gong: https://www.gong.io/ Salesforce: https://www.salesforce.com/ Twilio: https://www.twilio.com/ Vanta: https://www.vanta.com/ Where to find Stevie: LinkedIn: https://www.linkedin.com/in/steviecase/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Why early revenue hires fail 02:23 Who to hire at $5M in revenue 04:16 Coin-operated sellers vs. long-term builders 05:57 What excellence looks like in the CRO role 07:44 Metrics, confidence, and velocity 12:04 Should CROs lead sales? 14:39 From shy seller to revenue leader 16:36 Learning to scale at Twilio 17:44 "There is no CRO playbook" 19:58 Stevie's scaling mistake at Vanta 22:16 Why Vanta stays 100% sales-led 23:16 The value of planning 24-26 months ahead 29:54 When trusting intuition was the wrong call 30:49 Do humans still have a place in the future of GTM? 33:33 Stevie's leadership non-negotiables 36:36 The myth of hiring for industry expertise 40:00 What stays centralized in a 600-person company 47:09 The hidden leverage of a customer's first 30 days 53:42 Why the CRO role will face enormous changes by 2028 58:42 What leaders must do now to stay relevant 01:02:30 Unpacking the CEO-CRO dynamic

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

In the first Executive Function episode, Brett sits down with Jeanne De Witt Grosser, Chief Operating Officer at Vercel. Before Vercel, Jeanne spent nearly a decade at Stripe, where she built and scaled global revenue teams and led product partnerships. In this conversation, she unpacks what separates good executives from extraordinary ones, shares her rigorous executive hiring process, and reveals the brutally honest performance review feedback she'll never forget. In today's episode, we discuss: What it takes to operate at 30,000 feet and ground level simultaneously The leap from frontline manager to manager of managers Inside Jeanne's executive interview process The inherent value of driver trees for metrics Why context is everything References: Akamai: https://www.akamai.com Claire Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/ Culture Amp: https://www.cultureamp.com Guillermo Rauch: https://www.linkedin.com/in/rauchg John Collison: https://www.linkedin.com/in/johnbcollison/ Next.js: https://nextjs.org Nike: https://www.nike.com OpenAI: https://www.openai.com Patrick Collison: https://www.linkedin.com/in/patrickcollison Stanford Graduate School of Business: https://www.gsb.stanford.edu Stripe: https://www.stripe.com Vercel: https://www.vercel.com Where to find Jeanne: LinkedIn: https://www.linkedin.com/in/jeannedewitt Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:17) What separates good executives from extraordinary ones (02:48) How leadership changes as companies scale (04:15) What an executive is actually accountable for (06:11) The leap most rising leaders never make (07:52) When to dive deep vs. when to step back (10:09) Teaching people to think like you do (11:56) Creating a shared language across the business (13:52) What a COO job description actually looks like (17:20) The upside of owning the full customer experience (19:10) Why marketing rolls up under a COO (21:06) Being demanding and supportive at the same time (22:33) Inside the executive interview process (27:35) The workshop prompts that reveal everything (30:11) The common thread in failed executive hires (36:36) Metrics: the driver tree philosophy (43:04 What a collaborative exec team looks like (57:08) How Stripe got 30 people to operate as one team (1:03:50) Working yourself out of a job (1:10:32) The review feedback you can't unhear

Anil Varanasi is the co-founder and CEO of Meter, which provides full-stack networking infrastructure as a service for businesses. Since founding Meter with his brother Sunil in 2015, Anil has been playing a distinctly long game in one of the most entrenched markets in technology, betting on vertical integration, business model innovation, and a multi-decade time horizon. In this conversation, he unpacks Meter’s origin story, from four-plus years of heads-down R&D, and shares how his unconventional approach to planning, management, and pace keeps him excited to run the company for decades. In today’s episode, we discuss: Why Anil thinks in 25-year horizons How operating in a monopolistic market shaped Meter’s approach Why Meter scrapped a year of OS work during the R&D phase How Meter is rethinking networking’s business model Surviving COVID, Apple’s M1 transition, and “a thousand bad days” Anil’s contrarian views on planning, OKRs, and management How founders can build companies they’ll want to run for decades Where to find Anil: LinkedIn: https://www.linkedin.com/in/anilcv/ Twitter/X: https://x.com/acv Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: ADT: ⁠https://www.adt.com⁠ Alex Honnold: ⁠https://www.alexhonnold.com⁠ Alex Tabarrok: ⁠https://x.com/ATabarrok⁠ ⁠alarm.com⁠: ⁠https://www.alarm.com⁠ Andreessen Horowitz (a16z): ⁠https://a16z.com⁠ Apple: ⁠https://www.apple.com⁠ Bloomberg: ⁠https://www.bloomberg.com⁠ Bryan Caplan: ⁠http://www.bcaplan.com/⁠ Cisco: ⁠https://www.cisco.com⁠ Coca-Cola: ⁠https://www.coca-colacompany.com⁠ George Mason University (GMU): ⁠https://www.gmu.edu⁠ Intel: ⁠https://www.intel.com⁠ Julia Galef: ⁠https://x.com/juliagalef⁠ Martin Casado: ⁠https://www.linkedin.com/in/martincasado/⁠ Meraki: ⁠https://meraki.cisco.com⁠ Meter: ⁠https://www.meter.com⁠ Michela Giorcelli: ⁠https://x.com/M_Giorcelli⁠ Nicholas Bloom: ⁠https://www.linkedin.com/in/nick-bloom-stanford/⁠ Raffaella Sadun: ⁠https://www.linkedin.com/in/raffaella-sadun-3a182225/⁠ Sanjit Biswas: ⁠https://www.linkedin.com/in/sanjitbiswas/⁠ Sunil Varanasi: ⁠https://www.linkedin.com/in/sunil-varanasi-662a01253/⁠ Tyler Cowen: ⁠https://www.linkedin.com/in/tyler-cowen-166718/⁠ Twitch: ⁠https://www.twitch.tv⁠ Timestamps: (01:27) Meter’s unusual timeframes (04:06) “We don’t do OKRs” (06:32) How to plan without planning (08:31) Track your unhappy customers (11:43) How Meter’s journey began (15:02) Dissecting the 2010s SaaS boom (17:06) The networking industry trap (21:44) Meter’s first roadblock (22:07) Why Shenzhen accelerated Meter’s progress (26:29) The process to get a sales-ready product (31:02) Why you should own the full stack (32:45) The surprising thing you should innovate (35:03) Avoiding the one-trick pony trap (37:39) The secret to finding an excellent market (43:48) How COVID’s constraints propelled growth (48:25) Why founders need to know their customers (49:34) Why Meter didn’t sell via traditional channels (51:44) You need “seller-market fit” (54:51) The danger of meta-work (56:25) Decoupling management from authority (1:02:17) When the person is the problem (1:05:05) The inherent value of going slowly (1:09:41) Running a company for as long as possible

Jyoti Bansal is the co-founder and CEO of Harness, the software delivery platform used by thousands of engineering teams, and previously founded AppDynamics, which he led from inception to a multibillion-dollar acquisition by Cisco. In this episode, Jyoti unpacks what it really takes to move from mid-market to enterprise, why he thinks in terms of “product-market-sales fit,” and how he structures Harness as a collection of “startups within a startup” to launch multiple “best-of-breed” products. In today’s episode, we discuss: Why companies get stuck in the mid-market and struggle to move up into enterprise Why Jyoti deliberately lost Netflix as their customer The difference between product-market-sales fit, and product-market-fit How to build a scalable, capacity-driven go-to-market machine (instead of chasing deals) Diagnosing whether you have a product problem or a distribution problem How to hire and evaluate your first head of sales and top sales leaders Why Jyoti sold AppDynamics three days before IPO The “binary differentiator” rule for launching new products into crowded markets Why Harness runs 16 product lines under one roof Where to find Jyoti: LinkedIn: https://www.linkedin.com/in/jyotibansal/ Twitter/X: https://x.com/jyotibansalsf Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Amazon: https://www.amazon.com/ AppDynamics: https://www.appdynamics.com/ Barclays: https://home.barclays/ BIG Labs: https://www.biglabs.com/ Carlos Delatorre: https://www.linkedin.com/in/cadelatorre/ Charles Schwab: https://www.schwab.com/ Cisco: https://www.cisco.com/ Citi: https://www.citi.com/ Cloudability: https://www.apptio.com/products/cloudability/ Datadog: https://www.datadoghq.com/ Dynatrace: https://www.dynatrace.com/ Harness: https://www.harness.io/ Jeff Bezos: https://x.com/JeffBezos Microsoft: https://www.microsoft.com/ Nasdaq: https://www.nasdaq.com/ Netflix: https://www.netflix.com/ New Relic: https://newrelic.com/ Salesforce: https://www.salesforce.com/ Splunk: https://www.splunk.com/ Traceable: https://www.traceable.ai/ Unusual Ventures: https://www.unusual.vc/ VMware: https://www.vmware.com/ Timestamps: (01:48) Why do companies get stuck in the mid-market? (05:09) Designing a product for enterprise and mid-market (07:19) Why Jyoti lost Netflix as a customer - on purpose (10:18) Becoming a scalable GTM organization (12:32) The real signs of product-market fit (14:04) Have you delivered the value? (15:46) How to hire your first sales team (19:59) The four signs of excellent sales leaders (23:16) How to interview a sales leader (27:51) Where Jyoti developed his commercial taste (29:37) Why early founders need to learn sales (32:02) How AppDynamics began (36:36) Why Jyoti sold three days pre-IPO (41:55) What does a healthy board look like? (44:23) How Jyoti perceives competition (46:18) Why you need a binary differentiator (49:53) How to launch multiple products (52:00) “We need to be best of breed” (57:38) Why PMs are like mini-entrepreneurs (1:00:20) The startup within a startup (1:02:45) A culture of continuous improvement

Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever encountered: business-to-business transaction exchange. He spent years building EDI infrastructure, threw away the entire codebase eight times, and found extraordinary traction in healthcare. Stedi recently raised a $70M Series B co-led by Stripe and Addition. In this conversation, Brett and Zack discuss why venture capital means "going pro," why execution is never actually a moat, and how "eating glass" became Stedi's competitive advantage. In today’s episode, we discuss: How 16-year-old Zack turned $2,500 into a wholesale empire Why bootstrapping means being "constrained by capital" and how VC removes that ceiling Why Zack rebuilt their EDI product eight times before launch The snake swallowing a deer: what extreme product-market fit really looks like What software companies can learn from discount retail and Toyota Why Stedi’s new hires are told "everything’s your fault now" And much more Where to find Zack: LinkedIn: https://www.linkedin.com/in/zkanter Twitter/X: https://x.com/zackkanter Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Aetna: https://www.aetna.com/ Amazon: https://www.amazon.com/ AWS: https://aws.amazon.com/ Blue Cross Blue Shield: https://www.bcbs.com/ Change Healthcare: https://www.changehealthcare.com/ Cigna: https://www.cigna.com/ Clay: https://www.clay.com/ Costco: https://www.costco.com/ Ford Motor Company: https://www.ford.com/ GM: https://www.gm.com/ HIPAA overview (HHS): https://www.hhs.gov/hipaa/index.html Jeff Bezos: https://x.com/JeffBezos Kanban / TPS (Toyota): https://global.toyota/en/company/vision-and-philosophy/production-system Microsoft Teams: https://www.microsoft.com/microsoft-teams NetSuite: https://www.netsuite.com/ O’Reilly Auto Parts: https://www.oreillyauto.com/ Peter Thiel: https://x.com/peterthiel Porter’s five forces: https://www.isc.hbs.edu/strategy/pages/the-five-forces.aspx "Reality has a surprising amount of detail": https://johnsalvatier.org/blog/2017/reality-has-a-surprising-amount-of-detail Slack: https://slack.com/ Stedi: https://www.stedi.com/ Summit Racing: https://www.summitracing.com/ Target: https://www.target.com/ Walmart: https://www.walmart.com/ Zapier: https://zapier.com/ Timestamps: (01:24) Zack’s first business (08:54) Why the first customer is tricky (10:12) The downside of bootstrapping (11:42) Why venture capital is like “going pro” (14:20) The confusion between ownership vs. control (16:08) Building a company you don’t want to leave (20:46) Do things better than other people (24:49) Stedi’s early years (31:43) Physical vs. digital product-market fit (34:41) How Stedi scaled decision-making (40:08) Stedi’s journey to product-market fit (45:22) Finding founder-approach fit (50:42) “All software is a cascade of miracles” (52:52) The surprising lessons from discount retail (57:50) How the Toyota production system influences software (1:01:31) What it means to be a high-agency person (1:03:09) The core trait Zack looks for when hiring (1:02:57) Maintaining conviction in unconventional practice (1:14:19) When should you start to hire managers? (1:17:42) “Reality has a surprising amount of detail”