Founder Mode

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

EPISODE 22In this episode of Founder Mode, Anurag Agarwalla shares his journey from leading fast-moving engineering teams at Uber to building hpy, an AI-powered platform designed to support therapists and patients in achieving better outcomes. He explains why emotional systems matter as much as technical ones, how to design for happiness without burning out, and why privacy and empathy must be foundational in mental health tech. The conversation dives into emotional intelligence, daily habits, and how AI can serve as a companion tool without replacing the human connection at the core of therapy.CHAPTERS00:00 – From Uber to building for happiness05:12 – Healing the healer: AI for therapists09:27 – Privacy and ethics in mental health tech14:06 – Designing systems for happiness and balance23:37 – Building tools for healthier habitsLINKSConnect with Anurag Agarwallathinkhpy.com • LinkedIn • X/TwitterConnect with hpyLinkedIn • X/Twitter • InstagramSpecial OfferDo you go to therapy? Your next therapy session is on us. With hpy, we help clinicians help YOU reach your goals faster with better outcomes, tracking and progress. Introduce us to your therapist and if they sign up for hpy, your next session is on us. Email sales@thinkhpy.com to get started and mention Founder Mode. Are you a mental health professional and want to automate all of your admin? With hpy Pro, the first AI assistant designed specially for therapy, save up to 20 hours a week. We’re offering Founder Mode listeners an exclusive—refer a colleague and get an entire YEAR of hpy Pro free. To get registered, email sales@thinkhpy.com and mention Founder Mode.Stay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 21Hosts Kevin Henrikson and Jason Shafton go beyond the headlines to unpack the real bottlenecks that stall healthcare—and how to fix them—with consultant and operator Rebecca Shufeldt, founder of Ignite Healthcare Solutions. Drawing on her path from urgent care ops to EHR/revenue cycle leadership, Rebecca explains why go‑live is “day zero,” how her evolving “Silver Bullet” project plan keeps Athenahealth implementations aligned to payer/CMS changes, and where AI—voice intake, scheduling, eligibility, authorizations and referrals—removes administrative drag, reduces denials, and lifts patient and clinician satisfaction. The group digs into tailoring EHRs beyond “turnkey,” building clinician buy‑in, upskilling staff instead of replacing them (“Betty”), and how a flexible, female‑led team model helps practices scale without burnout while improving revenue.CHAPTERS00:00 – Setting the stakes: healthcare’s hidden blockers + Jason’s Heal story02:00 – AI as a wedge: voice, eligibility & EHR‑integrated routing05:03 – Meet Rebecca Shufeldt & Athenahealth optimization10:19 – The “Silver Bullet” plan: go‑live is day zero12:55 – Revenue cycle pitfalls, authorizations & upskilling the teamCONNECT WITH REBECCAWebsite • LinkedInSPECIAL OFFERIgnite Healthcare Solutions is offering a complimentary 30-minute athenahealth optimization review with our CEO for Founder Mode listeners. We’ll assess your current use of the platform, highlight quick-win opportunities to improve efficiency and revenue, and share proven strategies tailored to your organization’s goals—whether you’re a start-up, an established practice, or an MSO.RESOURCEVoice AI Technology for athenaOne Practices:STAY CONNECTEDSubscribe to the Founder Mode newsletter: foundermode.kit.comCONNECT WITH KEVINLinkedIn • X/TwitterCONNECT WITH JASONLinkedIn • X/Twitter

Ahad Khan, CEO of Kajabi, empowers creators to build sustainable businesses through monetization. He emphasizes shifting focus from virality to long-term ownership, discussing actionable strategies for pricing and achieving content market fit. Ahad also shares insights on integrating AI while preserving personal connections, the critical role of post-founder leadership, and how creators can validate their ideas through audience engagement. His vision for the creator economy highlights the importance of entrepreneurial creators and customer obsession.

EPISODE 19Visibility isn't a vibe—it's a system. In this episode, Jason and Kevin sit down with Chris Winfield, creator, connector, and coach, to break down how founders can build an unfair advantage in an AI-saturated world. Chris shares his 80/20 rule for AI usage, why content strategy is non-negotiable in 2025, and how personal connection still beats automation. Learn how to become the go-to expert in your niche, simplify your message like Steve Jobs, and avoid falling into the “Slopbot” trap of over-AI'd content.CHAPTERS00:00 – The 80/20 Rule for Using AI06:26 – Visibility Through Content and Connection12:11 – Build Real Relationships in a Noisy Digital World15:28 – Marketing Trends That Actually Matter in 202519:37 – The Real Unfair Advantage for FoundersLINKSConnect with ChrisInstagram • LinkedInSpecial OfferDM Chris on Instagram @chriswinfield and mention Kevin & Jason to get a special offer.Stay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter