Founder Mode

EPISODE 32Founder Mode sits down with Natalie Kaminski of JetRockets to cut through AI hype in software development. Natalie shares findings from a five-month experiment using code assistants: top engineers see ~30% efficiency on tedious tasks, but AI can duplicate components, forget context, and mislead juniors who can’t evaluate output. She argues developers matter more than ever—AI augments, not replaces—while real value comes from problem definition, secure architecture, and disciplined human review. Tools help with migrations, boilerplate, and tests; judgment, clarity, and empathy still decide what ships.CHAPTERS00:00 – There’s no “I” in today’s AI03:30 – Do developers still matter?04:51 – AI as augmentation: the calculator analogy06:41 – Workable AI: migrations, boilerplate, tests (~30% gain)19:08 – Where AI breaks: duplication, lost context, human reviewLINKSConnect with Natalie Kaminskijetrockets.com • LinkedIn • X/TwitterStay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 31In this live Founder Mode episode recorded at Workshop in San Francisco, Jason and Kevin sit down with two of the most influential builders in modern tech — Max Mullen, Co-Founder of Instacart, and Andrew Ofstad, Co-Founder of Airtable. They share never-before-heard founding stories, from Instacart’s $20K Trader Joe’s hack to Airtable’s first prototype built entirely in local storage. The conversation spans early lessons in scrappy product development, balancing speed and craft, scaling company culture, leadership evolution, and founder burnout. They also dive into how AI is reshaping startup building, what makes SF’s comeback real, and their most contrarian lessons from a decade of creating category-defining companies.CHAPTERS0:00 – Welcome to Founder Mode Live2:00 – Backing the Cybertruck into Workshop4:25 – The $20K Trader Joe’s Story9:45 – Building Instacart’s First Catalog10:58 – Airtable’s Early Browser-Only MVP15:32 – Speed vs. Craft: Product Tradeoffs22:18 – Scaling Culture and Leadership29:10 – Founders on AI, Product, and Speed35:44 – Burnout, Balance, and Founder Longevity42:36 – SF’s Comeback and Final LessonsLINKSConnect with Max Mullenmaxmullen.com • LinkedIn • X/TwitterConnect with Andrew OfstadLinkedIn • X/TwitterStay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 30Microsoft product leader Sangya Singh joins Jason and Kevin to unpack how to decide what to ship first in AI and automation. She shares a “strategy to win” playbook (fall in love with the problem, define the hypothesis, then hire and build), why agility must be daily not monthly, and how Microsoft balances agentic and deterministic systems—highlighting a risky-but-breakthrough bet on self-healing RPA. The crew contrasts outputs vs. outcomes, explores eval-driven prioritization, and talks scale mechanics inside Microsoft. Sangya closes with what’s next: voice-based AI surfaces that discover what to automate and “mech-interrupt” style safety tooling so enterprises can see, govern, and correct model behavior.CHAPTERS00:00 – Cold open: “Say no to great”00:28 – MVPs and sequencing in the AI era03:45 – Sangya’s path & “strategy to win”10:40 – Self-healing RPA and outcomes over outputs25:35 – What’s next: AI surfaces & safetyLINKSConnect with Sangya Singh LinkedIn • X/TwitterStay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 29Private equity meets AI in a grounded, operator-first conversation with Jason Friedrichs of AEA Elevate. We cover why “no-regrets” initiatives and clear ROI gates beat hype cycles, how to build an AI-first value creation plan, and why team design—not just capital—drives repeatable growth. Jason shares his thoughts on where PE playbooks are shifting beyond spreadsheets, the small wins that compound across functions (GTM, support, back office), how to navigate macro shocks, and what sectors he believes are primed for outsized AI-enabled revenue and margin expansion.CHAPTERS00:00 – The “no-regrets” move00:37 – Framing PE × AI: beyond hype to operating leverage06:19 – ROI discipline, pilots, and budgeting for AI15:20 – Beyond capital: the PE playbook & first 180 days20:21 – Healthcare opportunity, macro shocks, and exitsLINKSConnect with Jason Friedrichsaeainvestors.com/elevate • LinkedInStay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 28Jason and Kevin dig into why health isn’t a solo sport—and how founders can extend their “work span” by prioritizing community, shared rituals, and better device hygiene. They cover replacing PR-chasing with longevity metrics, carving out weekly “sensorless” time to reset attention, and using an AI “board of directors” to stress-test health decisions (like peptides, CGMs, and more). Practical takeaways: find your people (gyms, classes, sauna/cold communities), schedule analog friction, and optimize for effective hours—not performative 80-hour weeks.CHAPTERS00:00 – Work span > hours: redefining “hard work”00:33 – Health as community, not willpower04:32 – Built-in community: gyms, classes, rituals10:18 – Going “sensorless”: the off-grid reset19:37 – An AI board of directors for your healthLINKSStay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/TwitterSYSTEM PROMPTHEALTH & LONGEVITY BOARD OF DIRECTORSA pragmatic, evidence-labeled council for healthspan, performance, and physical well‑being.[Consensus][Promising][Speculative]PurposeYou are a council of expert advisors serving as a personal “Board of Directors” for healthspan, performance, and physical well‑being. Each advisor is an AI persona modeled on leaders in the field (fictionalized, evidence‑based, pragmatic).Operating PrinciplesClarity first: short, specific bullets; quantify when possible.Evidence labels: [Consensus] [Promising] [Speculative]. State assumptions & uncertainty.Risk triage: flag red‑flags & when to escalate to in‑person care.Iterative: smallest high‑ROI next step; define metric & timebox experiments.Personalization: use known profile; if missing data, note assumptions.Quarterly cadence: prompt refresh of goals / labs / constraints.Profile (Example Template)Demographics: adult male.Body composition: mid‑teens % body fat.Goals: reduce body fat to ~12–15%; visible abs; strong back & shoulders; high energy & sleep quality; sustainable fitness under reasonable weekly time budget.Cardio/Metabolic: moderate VO2 max; uses CGM for tight glucose control.Training: brief daily strength sessions; occasional joint/back tightness.Lifestyle: frequent travel; values minimalism, precision, and clear instructions.Board Composition — Core (Always Respond)Moderator / Systems IntegratorSynthesizes advice; resolves trade‑offs; produces unified plan & metrics.Longevity & Preventive Medicine PhysicianFocus: risk stratification, screening, lab strategy, lifespan vs healthspan trade‑offs.Cardiometabolic & Lipid SpecialistFocus: ASCVD risk, apoB/LDL/Lp(a), CAC use, BP targets, exercise cardiology.Endocrinology & Men’s HealthFocus: thyroid axis, insulin sensitivity, testosterone, bone density, prostate screening.Sleep Medicine PhysicianFocus: OSA screening, circadian rhythm, travel protocols, insomnia differentials.Neuroscience & Behavior Change AdvisorFocus: habit formation, motivation, stress tools, light and temperature timing.Performance Physiology & Strength CoachFocus: program design, block periodization, load/volume balance, recovery rules.

EPISODE 27Ankur Goyal joins Founder Mode to show how real teams get from AI prototype to production: build a two-click loop from user complaint to eval, treat observability as a driver of quality, and design iteration environments that connect production logs back to tests. Ankur explains why LLMs behave more like databases than CPUs, how to avoid eval fatigue by curating the 5–10 examples that matter, and why top teams re-evaluate model choices monthly. He also looks ahead to agents that can review and improve other models’ work, turning today’s manual feedback loops into scalable systems.CHAPTERS07:53 – Why prototypes break in production10:22 – Iteration environments and closing the loop12:21 – LLMs are databases, not CPUs14:48 – Beating eval fatigue with ruthless prioritization21:15 – Observability as a driver of quality, not uptime25:25 – What’s next for evals, agents, and AI infraLINKSConnect with Ankur Goyalusebraintrust.com • LinkedIn • X/TwitterSPECIAL OFFEREmail ankur@braintrust.dev and mention Founder Mode to receive a special offer.Stay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 26Bobby Evans goes inversion-first on startup failure modes—from overhiring and bonus wars to vanity metrics, misaligned influencers, and shipping the wrong features. We dig into crypto betting’s realities, why credibility and payouts matter more than hype, the cost of public financialization, and how to protect thinking time, delegate, and avoid perfectionism that delays MVPs. Evans closes with location and personal-brand lessons: build where the network is and productize the founder early.CHAPTERS00:00 – Think time over busy calendars06:45 – Hard-earned lessons from crypto betting12:01 – Growth tactics that backfire18:43 – Red flags and credibility in the space25:22 – Location, personal branding, and founder adviceLINKSConnect with Bobby EvansCompany X/Twitter • Personal X/TwitterStay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 25In this episode, Metronome CEO Scott Woody breaks down how AI is rewriting the value of software—from “seats and subscriptions” to agents that do work—and why modern pricing must blend stability with upside. We cover where seat-based models break, how to design hybrid packages that align incentives (platform fee + usage/outcome), why early founders should copy the market and iterate fast, and how smart packaging reveals your ICP. Scott also looks ahead to a future where pricing and packaging become the competitive battleground across SaaS.CHAPTERS00:00 – AI rewrites software’s value04:05 – From Dropbox pain to Metronome10:06 – Hybrid pricing that aligns incentives14:35 – Early-stage: copy market, iterate, segment26:30 – Pricing/packaging becomes the battlegroundLINKSConnect with Scott Woodymetronome.com • LinkedIn • X/TwitterSPECIAL OFFEREmail sales@metronome.com and mention Founder Mode to get a special offer.Stay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

This highlights the importance of framing luck as the result of consistent effort and warns against burnout in entrepreneurship. Empathy is emphasized as a crucial competitive edge, while innovative strategies like sub-50 sq ft kiosks showcase creative go-to-market plays. The discussion also covers the balance of AI and human input in content creation, the significance of clear communication in product development, and the necessity for founders to prioritize ownership over mere virality.

EPISODE 23In this episode of Founder Mode, John Hancock joins us to break down the gap between startup hype and reality. From building Stonks—the largest angel syndication platform on AngelList—to walking away when the mission no longer fit, John shares what he’s learned about fundraising, pivots, and rebuilding with first principles. He introduces Validate, a tool designed to help founders and “idea people” kill bad ideas fast before wasting time or money, and explains why most AI features are “better shoes, not wings.” The conversation dives into validating ideas, writing as a way to sharpen thinking, and the most common founder mistake—stopping customer conversations. John closes with the raw truth: most people shouldn’t be founders, and that’s okay.CHAPTERS00:36 – The hype fades: AI as leverage + anyone-can-build moment07:42 – From Stonks to walking away: the pivot and why it didn’t fit10:31 – Validate: kill bad ideas fast (landing pages, plans, comps)13:46 – Don’t bolt on AI no one wants (“better shoes, not wings”)27:07 – The uncomfortable truth about being a founderLINKSConnect with John Hancockvldt.ai • X/TwitterSpecial OfferEmail john.hancock@hey.com to get Validate free forever. John is offering this exclusive deal to Founder Mode listeners—validate your ideas quickly, save time, and avoid building what no one wants.Cool ThingJason’s vibe-coded appStay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter