Explore every episode of the podcast Founder Mode
| Title | Pub. Date | Duration | |
|---|---|---|---|
| Simple Design is Best with Austin Boer | 18 Dec 2025 | 00:20:03 | |
EPISODE 37 Kevin and Jason sit down with Austin Boer, co-founder of Sleke, to unpack what it takes to build a “dumb phone” that still supports modern life. Austin shares how a simple insight from the r/dumbphone subreddit shaped Sleke’s mission: people want fewer distractions, not less utility. The conversation covers founder-led customer discovery, why Sleke is built around intentional constraints like banning infinite scroll, and how the team balances privacy, usability, and real-world needs like QR codes, maps, and music. They also explore the bigger question of what replaces the phone by 2030 and why digital minimalism should be accessible to everyone, not a luxury product. CHAPTERS 00:00 – The dumb phone problem people actually have 03:50 – Why Austin built Sleke and what the product is 04:30 – Founder-led discovery: 200+ ICP calls and shifting ICP 08:20 – The “fatal flaw” of dumb phones and preventing app creep 16:30 – Digital minimalism shouldn’t be a luxury LINKS Connect with Austin Boer sleke.io • Instagram • X/Twitter Special Offer: Use code FOUNDERS5 for a discount on a Sleke device. Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Future of Fundraising with Tim Barnes | 11 Dec 2025 | 00:24:48 | |
EPISODE 36 Kevin and Jason sit down with Scout cofounder Tim Barnes to rethink how founders raise capital in an AI-first world. Tim breaks down why most startups overlook trillions in available non-dilutive funding, how AI can automate painful proposal and compliance workflows, and why grants should function as a continuous business development engine—not a last-minute scramble for runway. They explore how climate, deep-tech, and healthcare companies can reposition their work to match shifting federal priorities without losing their mission, how Scout is helping both startups and government agencies modernize the funding ecosystem, and why founders should pursue grants before equity to validate traction and retain ownership. Tim also shares how he thinks about defensibility as foundation models advance, when to integrate grants into a capital strategy, and what it takes to keep founders focused on building instead of pitching. CHAPTERS 00:00 – Why non-dilutive funding matters 01:00 – Rethinking fundraising and bootstrapping in an AI hype cycle 05:30 – How Scout uses AI to unlock and manage grants 10:00 – Packaging your mission for shifting policy without losing focus 16:00 – When to use grants vs equity and how Scout’s fit check works LINKS Connect with Tim Barnes Special Offer Direct message Tim on LinkedIn and mention Founder Mode for 20% off your first year of Scout. Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| From AI Prototype to Production with Ankur Goyal | 02 Oct 2025 | 00:30:30 | |
EPISODE 27 Ankur 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. CHAPTERS 07:53 – Why prototypes break in production 10:22 – Iteration environments and closing the loop 12:21 – LLMs are databases, not CPUs 14:48 – Beating eval fatigue with ruthless prioritization 21:15 – Observability as a driver of quality, not uptime 25:25 – What’s next for evals, agents, and AI infra LINKS Connect with Ankur Goyal usebraintrust.com • LinkedIn • X/Twitter SPECIAL OFFER Email ankur@braintrust.dev and mention Founder Mode to receive a special offer. Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| How Not to Run a Startup with Bobby Evans | 25 Sep 2025 | 00:30:45 | |
EPISODE 26 Bobby 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. CHAPTERS 00:00 – Think time over busy calendars 06:45 – Hard-earned lessons from crypto betting 12:01 – Growth tactics that backfire 18:43 – Red flags and credibility in the space 25:22 – Location, personal branding, and founder advice LINKS Connect with Bobby Evans Company X/Twitter • Personal X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Right-Price Your SaaS with Scott Woody | 18 Sep 2025 | 00:35:11 | |
EPISODE 25 In 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. CHAPTERS 00:00 – AI rewrites software’s value 04:05 – From Dropbox pain to Metronome 10:06 – Hybrid pricing that aligns incentives 14:35 – Early-stage: copy market, iterate, segment 26:30 – Pricing/packaging becomes the battleground LINKS Connect with Scott Woody metronome.com • LinkedIn • X/Twitter SPECIAL OFFER Email sales@metronome.com and mention Founder Mode to get a special offer. Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Best of Founder Mode I | 11 Sep 2025 | 00:19:02 | |
EPISODE 24 A special “best of” highlight reel from our first 20 episodes: we reframe luck as reps and compounding, warn founders about burnout’s hidden interest, and show how AI can supercharge solo building without replacing your voice. We dig into making clear asks and saying “no” to protect focus, why empathy is the real product moat, and how durable edges come from hardware + proprietary data and real-world feedback. You’ll hear scrappy GTM plays (like sub-50 sq ft kiosks and Kickstarter’s customer collision), safety-first execution from nuclear to drones, pre-LLM agents, the 80/20 (AI/human) rule for content, and why creators should monetize ownership—not just virality. CHAPTERS 00:00 – Manufactured luck & the burnout tax05:04 – Empathy is the moat (AI changes jobs)09:49 – Safety & simplicity: nuclear-ready drones13:52 – Fail-forward roadmaps (hypotheses over hype)16:18 – AI 80/20 and the creator long tail LINKS Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| From Stonks to AI for Everyone with John Hancock | 04 Sep 2025 | 00:30:38 | |
EPISODE 23 In 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. CHAPTERS 00:36 – The hype fades: AI as leverage + anyone-can-build moment 07:42 – From Stonks to walking away: the pivot and why it didn’t fit 10:31 – 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 founder LINKS Connect with John Hancock Special Offer Email 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 Thing Jason’s vibe-coded app Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Building Happiness with Anurag Agarwalla | 28 Aug 2025 | 00:35:35 | |
EPISODE 22 In 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. CHAPTERS 00:00 – From Uber to building for happiness 05:12 – Healing the healer: AI for therapists 09:27 – Privacy and ethics in mental health tech 14:06 – Designing systems for happiness and balance 23:37 – Building tools for healthier habits LINKS Connect with Anurag Agarwalla thinkhpy.com • LinkedIn • X/Twitter Connect with hpy LinkedIn • X/Twitter • Instagram Special Offer Do 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 Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| The Healthcare Innovation Bottleneck with Rebecca Shufeldt | 21 Aug 2025 | 00:27:25 | |
EPISODE 21 Hosts 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. CHAPTERS 00:00 – Setting the stakes: healthcare’s hidden blockers + Jason’s Heal story 02:00 – AI as a wedge: voice, eligibility & EHR‑integrated routing 05:03 – Meet Rebecca Shufeldt & Athenahealth optimization 10:19 – The “Silver Bullet” plan: go‑live is day zero 12:55 – Revenue cycle pitfalls, authorizations & upskilling the team CONNECT WITH REBECCA SPECIAL OFFER Ignite 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. RESOURCE Voice AI Technology for athenaOne Practices: STAY CONNECTED Subscribe to the Founder Mode newsletter: foundermode.kit.com CONNECT WITH KEVIN CONNECT WITH JASON | |||
| The Creator CEO with Ahad Khan | 14 Aug 2025 | 00:33:35 | |
EPISODE 20 In this episode of Founder Mode, Kevin and Jason sit down with Ahad Khan, CEO of Kajabi, to unpack what it really means to be a “creator CEO” in 2025. From shifting creators’ mindsets beyond virality toward sustainable, owner-operated businesses, to finding content market fit before building products, Ahad shares actionable strategies for monetization, pricing, and using AI without losing the human touch. He also opens up about leading a global team as a post-founder CEO, honoring Kajabi’s customer-obsessed roots while implementing his own leadership cadence, and why the future belongs to entrepreneurial creators who build brands their audiences truly value. CHAPTERS 00:00 – Why “Creator CEO” is the Future of the Creator Economy 06:51 – Building for Everyday People and Customer Obsession at Kajabi 12:55 – Content Market Fit and Monetizing Beyond Virality 17:36 – Using AI to Scale Without Losing the Human Touch 25:07 – Leadership Cadence and Work-Life Integration as a Post-Founder CEO LINKS Connect with Ahad Khan SPECIAL OFFER Email ahad [at] kajabi.com for a special offer when you sign up for Kajabi. Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| The Founder’s Unfair Advantage with Chris Winfield | 07 Aug 2025 | 00:24:53 | |
EPISODE 19 Visibility 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. CHAPTERS 00:00 – The 80/20 Rule for Using AI 06:26 – Visibility Through Content and Connection 12:11 – Build Real Relationships in a Noisy Digital World 15:28 – Marketing Trends That Actually Matter in 2025 19:37 – The Real Unfair Advantage for Founders LINKS Connect with Chris Special Offer DM Chris on Instagram @chriswinfield and mention Kevin & Jason to get a special offer. Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Perfect Days With Your Ride-Or-Dies | 31 Jul 2025 | 00:22:47 | |
EPISODE 18 In this candid, fast-paced solo episode, Jason and Kevin unpack the systems behind their ideal weeks, why founders should prioritize health like a product launch, and how to build a ride-or-die team that spans multiple startups. From hiding jets from repo men to wearing smart glasses on the beach, they share war stories, personal rituals, and the mindset that separates cautious operators from calculated risk-takers. CHAPTERS 00:00 – The Casino Story That Saved FedEx 01:04 – Building Your Perfect Week 05:14 – Big Company Constraints Are (Mostly) Self-Imposed 10:00 – Health Is Your Only Asset 16:08 – Boomerangs vs. Boomer Rides LINKS Connect with Kevin Connect with Jason RESOURCES | |||
| AI, Health & Home with Max Drescher | 04 Dec 2025 | 00:28:04 | |
EPISODE 35 Kevin and Jason sit down with Healthcare AI Guy founder Max Drescher to unpack how AI is actually changing healthcare, from front-desk voice automation and AI scribes to clinical decision tools and consumer apps that give people more ownership of their data. Max shares how a habit of writing internal M&A news briefs at UnitedHealth turned into a fast-growing newsletter and community, why distribution has become one of the most important forms of founder leverage, and what separates real impact from hype in today’s healthcare AI boom. They dig into the rise of tools that reduce burnout and administrative friction, explore longevity, Blueprint-style protocols, and digital twins, and look ahead to a near future where AI-powered biology and smarter clinical support reshape medicine long before fully autonomous AI doctors arrive. CHAPTERS 00:00 – Why AI + health now 06:30 – Max’s path from M&A to Healthcare AI Guy and the power of distribution 12:10 – What’s real vs hype in healthcare AI for providers and patients 18:30 – Longevity, Blueprint, and founders getting serious about sleep 22:00 – The next five years of AI in health and where it’s all headed LINKS Connect with Max Drescher Healthcare AI Guy • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Water, The Next Frontier with Ravi Kurani | 24 Jul 2025 | 00:24:54 | |
EPISODE 17 Water‑tech pioneer Ravi Kurani explains how a floating pool‑chemistry robot became the ultimate hardware moat, why proprietary water data unlocks service marketplaces, and where trillion‑dollar opportunities lie at the water‑energy nexus. He recounts two years on Shenzhen factory floors perfecting Sutro, selling the startup before mass production, and now plotting to buy it back to tackle agriculture, cooling towers, and AI data centers. Hosts Jason Shafton and Kevin Henrikson unpack story‑driven design, founder persistence, and the future of “smart” water. CHAPTERS 00:00 – From Pools to Robotics: Ravi’s origin story 03:44 – Hardware Moats & Proprietary Water Data 07:11 – Sutro as the “Nest Cam” for Your Pool 09:01 – Water as Tech’s Next Trillion‑Dollar Frontier 16:36 – Founder Mode in China: Two Years on the Factory Floor LINKS Connect with Ravi Sutro • Liquid Assets Podcast • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Fail Forward with Angus Logan | 17 Jul 2025 | 00:24:02 | |
EPISODE 16 From living two years out of a suitcase to shipping AI products at Microsoft-scale, Angus Logan joins Kevin and Jason to unpack how “failing forward” accelerates learning. He explains why product teams should break things early each morning, how to shield a fast-moving startup culture inside a corporate giant, and the importance of weekly shipping cadences. Angus also shares his “LifeOps” playbook—100 travel-buddy rules, zero checked bags, and decision templates that free up brainpower—plus how culture-soaking trips and five-year-old Android phones keep him designing for real-world users everywhere. CHAPTERS 00:00 – Why failure is fuel 03:34 – Angus on rapid AI experimentation 06:50 – Integrating startups into Microsoft 10:58 – LifeOps: travel hacking & decision systems 18:47 – Global perspective and takeaways LINKS Connect with Angus Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Onshore to Offshore to AI with Shuja Keen | 10 Jul 2025 | 00:24:10 | |
EPISODE 15 AI builder Shuja Keen joins Kevin and Jason to trace his 20-year journey from building offshore labor forces to AI-native operations. He explains how falling bandwidth costs kicked off globalization, why today’s custom LLM agents are ready while people and processes lag, and how an abundance mindset lets founders redesign workflows instead of bolting AI onto old playbooks. Using metaphors like orthotics that adapt to your feet, Shuja shows how bespoke software, not one-size-fits-all packages, will unlock personalization in healthcare, education, and beyond—and urges founders to stop selling car parts and deliver the full “Uber” experience. CHAPTERS 00:00 – Outcomes Over Tools: The Uber Analogy 04:31 – Onshore → Offshore → AI: Shuja’s 20-Year Lens 11:32 – Custom Software & the Abundance Mindset 17:06 – AI’s Impact on Healthcare, Education & Inclusion 21:02 – Founder Playbook for 2025 LINKS Connect with Shuja Keen 786 Ventures • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| 15-Minute Workout with Lou Perrotta | 03 Jul 2025 | 00:14:30 | |
EPISODE 14 In this episode of Founder Mode, we hit the gym with legendary trainer Coach Lou Perrotta—who's spent decades working with elite entrepreneurs, celebrities, and top performers. Coach Lou shares how fitness, mindset, and consistency create compounding results—both in the gym and in business. From towel pull-ups in hotel rooms to 15-minute daily routines, Kevin, Jason, and Coach Lou talk about building mental resilience, breaking plateaus, and why the best founders train their bodies as relentlessly as they train their minds. CHAPTERS 00:00 – Why Every Founder Needs a Coach 01:05 – Coach Lou’s Origin Story 03:38 – Health is the First Investment 05:21 – Use What You Have 08:20 – Focus, Transformation, and Final Lessons LINKS Connect with Coach Lou Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Building AI Before It Was Cool with Dennis Mortensen | 26 Jun 2025 | 00:31:36 | |
EPISODE 13 Kevin Henrikson and Jason Shafton sit down with serial entrepreneur Dennis Mortensen (IndexTools, Visual Revenue, x.ai, and now LaunchBrightly) to unpack what it was really like to build an AI company years before large-language models existed. Dennis recounts owning the x.ai domain before Elon Musk, hand-labeling 32 million emails to train an early scheduling agent, and the costly product-design decisions that followed. He shares hard-won lessons on focusing on pain over technology, reverse-engineering post-acquisition goals, and why parenting teenagers is the ultimate sales boot camp. Dennis then introduces LaunchBrightly, his new platform that automates every product screenshot in your help center—and he caps the chat with an exclusive free-setup offer for Founder Mode listeners. CHAPTERS 00:00 – x.ai Before Elon 01:34 – Hand-Labeling 32 Million Emails 05:45 – Product Design > Prediction Precision 14:45 – Birth of LaunchBrightly 29:56 – Special Offer & Next Steps OFFER Connect with Dennis Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| From Hollywood to High-Rises: Making Robots with Asa Hammond | 11 Jun 2025 | 00:23:23 | |
EPISODE 12 From building gravity-defying camera rigs for Alfonso Cuarón’s Gravity to sending drones into live nuclear reactors and, most recently, designing job-site robots that can survive the dust and chaos of construction, Asa Hammond’s career shows how precision engineering and artistic vision can coexist. In this conversation, Asa explains how the exacting pixel-perfect discipline of Hollywood VFX became the blueprint for ultra-reliable industrial robotics, why safety and repeatability always come before flashy features, and how new UX layers—voice, LLMs, demonstration learning—are finally making complex machines feel like familiar tools. Along the way, we hear tales of full-scale “stunt-double” reactors, the reality of folding-laundry robots, and what it takes to assemble a world-class, T-shaped engineering team that thrives at the edge of possibility. CHAPTERS 00:29 – From Film Sets to Founders: Show Intro 02:12 – Asa’s Hollywood-to-Hard-Hats Origin Story 05:57 – Engineering Robots for Gravity 09:05 – Reinventing Construction with Industrial Arms 15:56 – Flying Drones Inside Nuclear Reactors LINKS Connect with Asa Hammond Website • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| The Future of Commerce: Product Design & Logistics with Samantha Rose | 03 Jun 2025 | 00:25:57 | |
EPISODE 11 From hand-carving a single silicone spatula in her kitchen to running a portfolio of revived consumer brands, Sam Rose walks Kevin and Jason through the through-line of her career: obsess over the customer, build a brand (not just a product), and make logistics as lovable as design. She explains how a “collision with the customer” on Kickstarter forced her into customer-service mode before she even had inventory, why color stories beat strict SKU rationalization, what the GIR sale to Pattern taught her about single-channel risk, and how vertical integration led to Manifest’s 3PL and the launch of Endless Commerce. Sam also breaks down AI’s role in just-in-time inventory, predicts an LLM-powered shopping future that both excites and unnerves her, and offers two free months of her commerce OS to fellow founders. CHAPTERS 00:00 – Collision with the Customer & Kickstarter Lessons 02:44 – Scaling GIR: Color Stories vs. SKU Discipline 07:32 – Acquisition Insights: Building a Balanced Brand Portfolio 09:54 – Manifest & the Cost of Learning Curves 13:03 – Endless Commerce and AI-Driven Supply Chains OFFER Get two months free on any tier and free onboarding to Endless Commerce when you mention the Founder Mode podcast or that Jason & Kevin sent you! LINKS Connect with Samantha Rose endlesscommerce.com • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| How to Bootstrap Your Tech Team Using AI with JJ Zhuang | 27 May 2025 | 00:27:05 | |
EPISODE 10 Serial CTO and Acompli co-founder JJ Zhuang joins Kevin and Jason to explain why the next generation of great products will be built by tiny, AI-super-powered teams. He unpacks lessons from taking Acompli’s first line of code to a $200 million Microsoft exit, steering Instacart through pandemic hyper-growth, and relearning to code with tools like GitHub Copilot, Cursor and Devin now writing the majority of his team’s code. Along the way JJ outlines the shift from hiring stack specialists to adaptable generalists, the rise of agentic “AI teammates,” and his mantra of “fast software” that lets founders prototype, test and ship at the speed of imagination—while still cutting through the 2025 hype cycle around agents and other buzzwords. CHAPTERS 00:00 – Shots Fired: Surprising Start & Show Kick-off 01:52 – From Acompli to Outlook: Building All-Star Teams 06:11 – Instacart’s Pandemic Sprint & Early AI Adoption 11:50 – Pair-Programming vs. Agentic Devs: Devin, Cursor & More 22:12 – Fast Software & Filtering the 2025 AI Hype LINKS Connect with JJ Zhuang Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason RESOURCES | |||
| De-Risking Brick-and-Mortar for DTC Brands with Megan Berry | 20 May 2025 | 00:30:38 | |
EPISODE 9 Megan Berry—architect, pop-up pioneer, and Mentors Fund partner—shows DTC founders how to move from clicks to bricks without torching cash. She explains her 8-foot-by-50-square-foot kiosk “permit hack,” the KPIs (unaided brand awareness, repeat engagement, dwell-time hot spots) that justify a multimillion-dollar flagship, and why post-COVID stores should feel like friction-free showrooms, not inventory caves. The talk digs into festival activations, cadence-matched merchandising, omni-channel partnerships that now include hotels and Pilates studios, AI-powered journey tracking, and practical founder advice on conserving runway while staying crazy-creative. CHAPTERS 00:00 – Permit Hack & Pop-Up Spark 06:46 – KPIs That Green-Light a Flagship 12:51 – Post-COVID, Low-Friction Store Design 19:17 – Omnichannel Expansion & Partnerships 26:25 – AI, Cash Efficiency & Founder Advice LINKS Connect with Megan Berry Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| AI-First Product Design with Ritwik Pavan | 13 May 2025 | 00:28:15 | |
EPISODE 8 In this episode, serial entrepreneur Ritwik Pavan joins Kevin Henrikson and Jason Shafton to explore the rise of AI-first product design and its profound implications on consumer hardware, smart cities, and modular construction. They discuss the essential strategies founders need to adopt, including the importance of hyper-personalization, overcoming challenges in training data, untapped opportunities in lifestyle and public safety sectors, and why AI is turning hardware into recurring revenue businesses. CHAPTERS 00:34 – What It Means to Build AI-First 03:53 – Ritwik’s Journey and AI Consumer Innovations 08:41 – Smart Cities, AI, and the Future of Urban Life 17:08 – Modular Construction and AI’s Role in Housing 22:20 – Underrated Opportunities: Lifestyle and Public Safety LINKS Connect with Ritwik Pavan Hardware Herald • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| When Founders Show Up | 20 Nov 2025 | 00:31:48 | |
EPISODE 34 In this episode, Kevin and Jason break down how founders can turn conferences from low-ROI distractions into high-leverage growth engines. Fresh off a major healthcare event in Nashville, they unpack why most networking fails, how Pretty Good AI turned a platinum sponsorship into a full activation with mini-golf and meeting pods, and the systems that converted casual foot traffic into hundreds of real customer conversations. They dig into founder-mode presence, team ownership, pre-work, follow-up, and the small details that make an event actually move the business forward. CHAPTERS 00:00 – The Value of Networking Events 01:25 – Challenges of Traditional Networking 02:47 – Reevaluating Event Participation 03:27 – Executing a Successful Conference Strategy 04:24 – Planning for a Major Conference Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Zero-to-One Marketing with Peter Farago | 06 May 2025 | 00:31:57 | |
EPISODE 7 In this episode, seasoned marketing leader Peter Farago shares zero-to-one marketing insights for early-stage startups, emphasizing empathy, iterative messaging, and organic inbound strategies. Drawing on experiences from Flurry, Acompli, and RunLLM, Peter highlights the importance of a clear value proposition, building brand credibility, and leveraging customer feedback loops. He also addresses AI’s evolving role in marketing, reassuring listeners that AI won’t replace jobs but will reshape how marketers operate. Packed with tangible advice, this conversation offers a roadmap for founders seeking to refine their product, storytelling, and growth approach in crowded markets. CHAPTERS 00:00 – Introducing Peter Farago and the Power of Empathy 01:34 – Zero-to-One Marketing Fundamentals 08:03 – Lessons from Acompli’s Early Growth 16:42 – Leveraging Customer Feedback and Iteration 29:04 – AI’s Evolving Role in Marketing LINKS Connect with Peter Farago runllm.com • LinkedIn • X/Twitter • Podcast Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Remote Boundaries – Saying No Without Burning Bridges with Viktor Petersson | 29 Apr 2025 | 00:28:03 | |
EPISODE 6 In this episode, Viktor Petersson shares how saying “no” can be a superpower for founders managing remote teams. He discusses practical strategies for email triage, boundary-setting to avoid burnout, and why in-person retreats are key to trust and alignment. Learn how Viktor’s approach to documentation, intrinsic motivation, and selective communication helps him preserve energy for what matters most—while still leaving the door open for valuable opportunities. CHAPTERS 00:00 – Why Saying No Matters for Remote Teams 02:23 – Setting Boundaries and Avoiding Burnout 09:12 – Remote Work Fundamentals & Hiring 15:18 – Onboarding & Team Summits 22:21 – Building Trust Through Retreats & Face-to-Face Time LINKS Connect with Viktor Petersson Screenly: https://www.screenly.io/ sbomify: https://sbomify.com/ Podcast: https://vpetersson.com/podcast LIinkedIn: https://www.linkedin.com/in/vpetersson/ X/Twitter: https://mobile.x.com/vpetersson Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| The Power of Asking with Andreas Homer | 22 Apr 2025 | 00:29:39 | |
EPISODE 5 In this episode of Founder Mode, Jason and Kevin sit down with Andreas Homer—startup founder, former BD leader at Microsoft, and now Head of Product Partnerships at Shopify—to explore the underrated superpower of asking. They unpack how a single well-phrased request can unlock jobs, capital, and high-leverage relationships. Andreas shares how he’s built a career by asking with clarity, fairness, and authenticity—whether it's securing investor intros, landing competitive roles, or hiring top-tier talent. The episode also dives into how to ask differently depending on your audience—investors, users, or team members—and why being yourself beats mimicking someone else’s style. The key lesson: Asking isn’t about pressure or persuasion—it’s about being clear, human, and real. CHAPTERS 0:00 — Why Asking Is a Founder Superpower 5:18 — How Andreas Landed Jobs by Asking the Right Way 11:02 — Fundraising: Clarity, Conviction & Handling Rejection 18:05 — Hiring: Framing Startups as Growth Opportunities 26:11 — Final Takeaway: Ask Authentically LINKS Connect with Andreas Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Anxiety is a Superpower if You Channel It with Slobodan "Sani" Manić | 08 Apr 2025 | 00:27:40 | |
Episode 4: In this episode of Founder Mode, Jason and Kevin kick things off with an unexpected Bill Russell story—revealing how the legendary NBA center threw up before every single game, including the easiest matchups. It becomes a perfect parallel for founders grappling with anxieties that simply won’t go away. They argue that anxiety, if handled properly, can be the secret sauce of drive and resilience. Special guest Slobodan “Sani” Manic, host of the No Hacks podcast and founder of PodPacer, discusses turning nerves into productive energy, the importance of building culture with real integrity (no shortcuts!), and why data should inform but never completely override your gut. They wrap by emphasizing old-school personal values in a world of AI-driven quick fixes—reminding us that nothing beats honesty and consistent effort when building a sustainable, founder-led venture. CHAPTERS 0:00 — Bill Russell & The Anxiety Factor 0:35 — Episode Intro: Anxiety as a Founder’s Superpower 1:08 — Overcoming Founder Anxiety & People Challenges 7:21 — Interview with Slobodan (No Hacks, PodPacer) 25:45 — Recap & Closing Thoughts LINKS Check Out Slobodan No Hacks Podcast • PodPacer • LinkedIn Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| AI & The Future of SaaS with Alex Finn | 01 Apr 2025 | 00:29:56 | |
Episode 3: In this episode of Founder Mode, Jason and Kevin dive into how AI is transforming startup life—from supercharging everyday workflows to enabling solo entrepreneurs to build fully functional SaaS products in record time. They share personal anecdotes on using AI tools for email summarization, research, marketing campaigns, and even multimillion-dollar licensing negotiations. The highlight is an interview with Alex Finn, founder of CreatorBuddy, who reveals how he leveraged AI coding to singlehandedly create a six-figure ARR content platform for X (formerly Twitter). Alex emphasizes the value of empowering individuals to act as independent entrepreneurs within organizations and explains why forming and expressing strong opinions is essential in a noisy tech landscape. The takeaway: AI can handle grunt work at lightning speed, but human insight, creativity, and leadership remain the driving forces behind true innovation. Chapters
Connect with Alex: X/Twitter Stay Connected Subscribe to the Founder Mode newsletter
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| The Hard Truth About Health & Hustle: You Can't Have it All | 25 Mar 2025 | 00:30:54 | |
Episode 2: In this episode, Jason Shafton and Kevin Henrikson discuss balancing health and hustle as a founder, exploring why many entrepreneurs struggle to maintain their health and relationships while building businesses. They highlight the importance of recognizing the phase you're in, using tools and AI to simplify health management, and proactively communicating with family and colleagues to protect essential relationships. Kevin shares insights from his extensive tracking of health data and how he leverages technology, while Jason provides candid reflections on managing family life amidst intense work commitments. The conversation emphasizes sustainable practices and prioritizing impactful actions over mere busyness. 00:00 - Intro: Crawl, Walk, Run Subscribe to the Founder Mode newsletter | |||
| Luck is a Skill - You Can Manufacture It | 14 Mar 2025 | 00:46:35 | |
Episode 1: In this first episode of Founder Mode, hosts Jason Shafton (Google, Headspace) and Kevin Henrikson (Acompli, Outlook, Instacart) break down the idea that luck isn't random—it's a skill you can manufacture. Through candid stories from their experiences at Google, Microsoft, and early-stage startups, Jason and Kevin reveal how successful founders intentionally create their own opportunities by taking risks, building strategic relationships, and rapidly experimenting. The conversation highlights the true essence of "founder mode," emphasizing a relentless bias for action, deep customer focus, and the growing importance of AI tools for entrepreneurs. Whether you're just starting out or leading at scale, this episode delivers actionable insights and inspiration to help you shift into founder mode and start making your own luck. 0:27 – What Is Founder Mode? Subscribe to Founder Mode newsletter: https://foundermode.kit.com/ Connect with Kevin: https://www.linkedin.com/in/kevinhenrikson/ https://twitter.com/KevinHenrikson Connect with Jason: https://www.linkedin.com/in/jasonshafton/ https://twitter.com/jasonshafton | |||
| Electrifying Aviation with Kevin Noertker | 13 Nov 2025 | 00:35:40 | |
EPISODE 33 Kevin Noertker, co-founder and CEO of Ampaire, is leading the charge toward sustainable aviation by electrifying the skies. In this episode, Kevin Henrikson and Jason Shafton visit Ampaire’s Long Beach hangar to talk about hybrid-electric aircraft, scaling innovation in a century-old industry, and why “hybrid isn’t the compromise—it’s the bridge.” Kevin shares how Ampaire is retrofitting existing planes to fly cleaner, safer, and farther using hybrid-electric propulsion, the challenges of certification and infrastructure, and the roadmap to fully electric flight. It’s a masterclass in pragmatic innovation—one that proves hardware can move fast when driven by purpose. CHAPTERS 00:00 – Expanding Horizons of Hybrid Aviation 05:00 – From Aerospace Giant to Startup Founder 12:30 – Why Hybrid Beats Fully Electric (for Now) 20:00 – Capital Efficiency and Government Partnerships 27:45 – The Future of Flight: Hybrid as the Bridge LINKS Connect with Kevin Noertker Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Will AI Replace Developers with Natalie Kaminski | 06 Nov 2025 | 00:23:49 | |
EPISODE 32 Founder 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. CHAPTERS 00:00 – There’s no “I” in today’s AI 03:30 – Do developers still matter? 04:51 – AI as augmentation: the calculator analogy 06:41 – Workable AI: migrations, boilerplate, tests (~30% gain) 19:08 – Where AI breaks: duplication, lost context, human review LINKS Connect with Natalie Kaminski jetrockets.com • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Founder Mode Live at San Francisco Tech Week with Max Mullen (Instacart) & Andrew Ofstad (Airtable) | 30 Oct 2025 | 00:46:23 | |
EPISODE 31 In 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. CHAPTERS 0:00 – Welcome to Founder Mode Live 2:00 – Backing the Cybertruck into Workshop 4:25 – The $20K Trader Joe’s Story 9:45 – Building Instacart’s First Catalog 10:58 – Airtable’s Early Browser-Only MVP 15:32 – Speed vs. Craft: Product Tradeoffs 22:18 – Scaling Culture and Leadership 29:10 – Founders on AI, Product, and Speed 35:44 – Burnout, Balance, and Founder Longevity 42:36 – SF’s Comeback and Final Lessons LINKS Connect with Max Mullen maxmullen.com • LinkedIn • X/Twitter Connect with Andrew Ofstad Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| AI + Automation: What to Ship First with Sangya Singh | 23 Oct 2025 | 00:30:13 | |
EPISODE 30 Microsoft 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. CHAPTERS 00:00 – Cold open: “Say no to great” 00:28 – MVPs and sequencing in the AI era 03:45 – Sangya’s path & “strategy to win” 10:40 – Self-healing RPA and outcomes over outputs 25:35 – What’s next: AI surfaces & safety LINKS Connect with Sangya Singh Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Private Equity + AI with Jason Friedrichs | 16 Oct 2025 | 00:26:51 | |
EPISODE 29 Private 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. CHAPTERS 00:00 – The “no-regrets” move 00:37 – Framing PE × AI: beyond hype to operating leverage 06:19 – ROI discipline, pilots, and budgeting for AI 15:20 – Beyond capital: the PE playbook & first 180 days 20:21 – Healthcare opportunity, macro shocks, and exits LINKS Connect with Jason Friedrichs aeainvestors.com/elevate • LinkedIn Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Health Is a Team Sport | 09 Oct 2025 | 00:23:54 | |
EPISODE 28 Jason 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. CHAPTERS 00:00 – Work span > hours: redefining “hard work” 00:33 – Health as community, not willpower 04:32 – Built-in community: gyms, classes, rituals 10:18 – Going “sensorless”: the off-grid reset 19:37 – An AI board of directors for your health LINKS Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason SYSTEM PROMPT HEALTH & LONGEVITY BOARD OF DIRECTORS A pragmatic, evidence-labeled council for healthspan, performance, and physical well‑being. [Consensus] [Promising] [Speculative] Purpose You 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 Principles
Profile (Example Template)
Board Composition — Core (Always Respond) Moderator / Systems Integrator Synthesizes advice; resolves trade‑offs; produces unified plan & metrics. Longevity & Preventive Medicine Physician Focus: risk stratification, screening, lab strategy, lifespan vs healthspan trade‑offs. Cardiometabolic & Lipid Specialist Focus: ASCVD risk, apoB/LDL/Lp(a), CAC use, BP targets, exercise cardiology. Endocrinology & Men’s Health Focus: thyroid axis, insulin sensitivity, testosterone, bone density, prostate screening. Sleep Medicine Physician Focus: OSA screening, circadian rhythm, travel protocols, insomnia differentials. Neuroscience & Behavior Change Advisor Focus: habit formation, motivation, stress tools, light and temperature timing. Performance Physiology & Strength Coach Focus: program design, block periodization, load/volume balance, recovery rules. | |||
| AI as a Financial Co-Pilot with Shain Noor | 23 Apr 2026 | 00:22:42 | |
EPISODE 53 In this episode, Kevin and Jason sit down with Shain Noor, co-founder of Silvia, an AI-powered personal CFO built to help people reason through financial decisions, not just track them. Shain explains why the entire history of personal finance apps has focused on clicking and aggregating data rather than helping users actually decide what to do, and how Silvia uses Anthropic-powered agents with a verification layer to deliver trustworthy, personalized financial guidance. The conversation covers the co-pilot vs. autopilot distinction, the surprising discovery that users ask Silvia things they'd never tell their human financial advisor, how proactive alerts like the daily summary email drove retention, and why building the reasoning layer first, before adding any execution or action capabilities, is the right foundation for trust. CHAPTERS 00:00 - The judgment-free financial advisor 02:38 - Introducing Shain Noor and Silvia 03:51 - Why finance apps have always missed the reasoning layer 05:51 - Co-pilot vs. autopilot: trust, transparency, and guardrails 08:29 - What surprised Shain: users sharing what they hide from their advisors 12:42 - Measuring retention and the proactive alerts breakthrough 17:02 - Team size, the ProCap merger, and competing with legacy finance 19:41 - The future: everyone becomes a manager of AI agents LINKS Connect with Shain Noor Stay Connected with Founder Mode Connect with Kevin Connect with Jason | |||
| Grab A Shovel | 16 Apr 2026 | 00:27:23 | |
EPISODE 52 Jason Shafton and Kevin Henrikson unpack where AI is genuinely useful and where it starts to create more noise than leverage, using examples from AI email triage, long chat memory drift, and agentic workflows. Kevin explains how memory can become polluted when models start treating their own prior inferences as fact, including a prompt he used to compare what an AI thought was “ground truth” against what he had actually told it. From there, the conversation shifts into a practical framework for building AI systems and human teams the same way: define the job, provide the right tools and access, layer in review and guardrails, and judge success by whether time spent together compounds into more output. They close by connecting startup hiring, high-agency operators, and founder-led culture back to the same core test they use for AI: does this person or tool create leverage, or does it create drag? CHAPTERS 00:00 – AI memory drift and false “ground truth” 01:24 – Testing AI email triage and the risks of over-filtering 03:13 – Good AI versus bad AI in real workflows 05:31 – Why controlled memory leads to more consistent AI outputs 08:29 – How to apply AI to workflows that currently rely on humans 11:12 – Building multi-agent content systems with clear roles and QA 13:40 – Hiring high-agency people for early-stage teams 16:01 – The “pick up the shovel” standard for startup operators 22:36 – The real test for both employees and AI: leverage or drag 26:16 – Founder Mode Top 5 Takeaways LINKS Connect with Kevin Henrikson Stay Connected with Founder Mode Connect with Kevin Connect with Jason | |||
| Scaling Multi-Location Businesses with Stephanie Joyce | 11 Feb 2026 | 00:25:26 | |
EPISODE 43 Kevin Henrikson and Jason Shafton sit down with Stephanie Joyce, founder and operator of Attune, to unpack what it really takes to scale multi-location service businesses without losing control of culture, operations, or margins. Drawing from years of leading growth, acquisitions, and crisis turnarounds, Stephanie explains why people come first, systems second, and how scaling simply amplifies whatever you already tolerate. The conversation covers documentation and onboarding as prerequisites for consistency, how to diligence acquisitions beyond surface-level financials, and what it means to lead with clarity and integrity when everything is on fire. They also dive into the modern med spa operating stack, from CRM and automation to compensation structures that drive the right behaviors, and why the future of wellness will be defined by better data, smarter technology, and a careful balance between AI and human trust. CHAPTERS 00:00 – People first, systems second: what breaks when you scale 04:25 – Documentation, SOPs, and onboarding for multi-location consistency 04:56 – Acquisition diligence: margins, concentration risk, and key-person dependency 08:06 – Leading through crisis: transparency, trust, and cash discipline 14:13 – The modern med spa playbook: systems, CRM, and incentives LINKS Connect with Stephanie Joyce Stay Connected with Founder Mode Subscribe to our newsletter: gofoundermode.com Connect with Kevin Connect with Jason | |||
| From Doctor to Founder with Jay Motley | 05 Feb 2026 | 00:25:17 | |
EPISODE 42 Kevin Henrikson and Jason Shafton sit down with Dr. Jay Motley, founder of MindWell Health, to explore what it takes to leave a long career in anesthesiology and build a modern mental health clinic. Jay shares how losing autonomy after his private practice was absorbed by a hospital system paired with the life-altering loss of his first wife pushed him to rethink time, care, and what getting better really means. The conversation dives into ketamine therapy as a fast-acting tool that can open a window for patients who have failed traditional treatments, and why lasting improvement depends on pairing that window with therapy and lifestyle medicine fundamentals like sleep, nutrition, movement, and stress management. They also cover the myths around expensive wellness biohacks, how AI could reduce administrative burden and expand patient access, and what Jay learned scaling from a one-person launch to multiple MindWell locations. CHAPTERS 00:00 – Ketamine as a fast-acting “open window” for change 00:50 – Health fundamentals that matter most: sleep, food, movement 04:20 – Why Jay left anesthesiology: autonomy, loss, and control of time 07:10 – Building MindWell: ketamine + therapy + lifestyle medicine 19:10 – Scaling the clinic: cash-pay vs insurance, systems, and hiring LINKS Connect with Dr. Jay Motley mindwell.com • LinkedIn • Instagram • X/Twitter • Substack • Facebook Stay Connected with Founder Mode Subscribe to our newsletter: gofoundermode.com Connect with Kevin Connect with Jason | |||
| Best of Founder Mode II | 29 Jan 2026 | 00:14:59 | |
EPISODE 41 After forty episodes, Founder Mode pauses to look at the decisions founders actually struggle with once the playbooks stop working. This episode stitches together clips across healthcare, AI, pricing, capital, aviation, and personal health to show how judgment forms under pressure. You hear why go-live is the start of real work, how trust gets broken when tools ship before problems are understood, why usage outlasts any value narrative, and how busyness becomes a substitute for thinking. Across every domain, the pattern is consistent: systems fail quietly, discipline erodes downstream, and founders are forced to make calls without clean data, perfect timing, or consensus. CHAPTERS 00:00 – Why the same founder problems keep repeating 01:01 – Go live is not the finish line 01:42 – Teaching interpersonal skills too late 02:34 – Adding AI before earning user trust 03:17 – When users reject AI and features get rolled back 03:57 – Why pricing complexity grows with mature markets 04:34 – Busyness as avoidance for founders 05:14 – Protecting thinking time before the business outgrows you 05:55 – Turning user complaints into learning fast 06:33 – Building a personal board of directors for health 07:27 – AI as a problem-solving lever, not a starting point 08:20 – Governance as the unlock for enterprise AI adoption 08:20 – When “magic” becomes table stakes for customers 09:10 – Why software being cheaper doesn’t make it easier 09:59 – Hybrid aviation as a trust bridge to electrification 10:51 – Measuring whether conference presence actually works 11:38 – Why AI scribes exploded in healthcare adoption 12:28 – Defaulting to venture capital and silent dilution 12:28 – Designing products that force focus and community 13:06 – Stress, judgment, and risk in aviation 13:43 – Unlimited pricing as a math problem 13:43 – Learning faster by removing safety nets 14:31 – Making decisions when there is no right answer LINKS Stay Connected with Founder Mode Stay Connected with Founder Mode Connect with Kevin Connect with Jason | |||
| Move Fast & Brake Things with Allen Berg | 22 Jan 2026 | 00:13:39 | |
EPISODE 40 Recorded at Laguna Seca Raceway, this episode takes Founder Mode out of the studio and onto the track. Jason and Kevin spend the day driving open-wheel formula cars and sit down with Allen Berg, founder of Allen Berg Racing Schools, to talk about learning through feel, momentum, and control. Berg walks through his path into racing, what makes formula cars such an effective teaching platform, and how racing schools function as the entry point to professional motorsport. The conversation draws clear parallels between racing and building companies: managing risk without automation, carrying momentum through corners, and knowing where the limits actually are. CHAPTERS 00:00 – Growing up with racing and early influences 01:05 – Driving formula cars at Laguna Seca 02:52 – Racing as a model for building companies 05:40 – Building and operating a racing school 09:44 – Advice for founders building niche businesses LINKS Connect with Allen Berg Allen Berg Racing Schools • LinkedIn Stay Connected with Founder Mode Connect with Kevin Connect with Jason | |||
| Uh-Oh Everything's Broken with Jonathan Sturgeon | 15 Jan 2026 | 00:28:18 | |
EPISODE 39 Jonathan Sturgeon joins Founder Mode to explain how he built multiple eight-figure businesses without chasing an audience, a personal brand, or social media validation. He breaks down his deliberately anti-influencer posture, why cold calling still outperforms content for high-intent sales, and how his companies Dingus & Zazzy and Uh Oh scale through systems, scripts, and trust rather than hype. The conversation moves from trolling internet fame culture to designing a radically simple IT business with a free trial and pay-what-you-want pricing, and ends with Jonathan’s view that not every project needs to optimize for returns—some are worth doing because they’re fun. CHAPTERS 00:00 – Building businesses without social media or an audience 03:45 – The anti-influencer mindset and trolling internet fame 11:45 – Cold calling, scripts, and why outbound still works 15:30 – Uh Oh: free-trial IT, pay-what-you-want pricing, and trust 24:00 – Art over profit and building businesses for enjoyment LINKS Connect with Jonathan Sturgeon Uh Oh • Dingus & Zazzy • LinkedIn • X/Twitter Stay Connected with Founder Mode Connect with Kevin Connect with Jason | |||
| From Flight Deck to Front Line with Max Trescott | 08 Jan 2026 | 00:20:29 | |
EPISODE 38 Recorded mid-flight in Kevin’s Vision Jet en route to Monterey, Kevin and Jason talk with veteran pilot and aviation podcaster Max Trescott about why flying can feel like a flow-state reset, and how the discipline of aviation maps to building companies. Kevin shares his path from earning a pilot’s license in college to taking a long break, then returning to aviation with structured training, checklists, and the calm that comes from repetition. Together they unpack why “it’s not hard, it’s a lot of effort,” why SOPs and emergency prep matter when things break, and the real key to learning: consistent time in the seat, the right instructor, and a focus on proficiency over deadlines. CHAPTERS 00:00 – Flying as a stress reset and the “are you ready?” check 00:48 – Welcome to Founder Mode from the Vision Jet 02:55 – Kevin’s pilot journey: college license to getting hooked on the Vision Jet 05:23 – The founder/pilot overlap: effort, SOPs, and staying calm when things change 13:09 – Buying (and upgrading) a jet: the sales cycle, timing, and “right message, right moment” LINKS Connect with Max Trescott Aviation News Talk • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter: foundermode.kit.com Connect with Kevin Connect with Jason | |||
| Turning Audiences Into Businesses with Courtney Spritzer | 09 Apr 2026 | 00:25:58 | |
EPISODE 51 Courtney Spritzer breaks down how she built, scaled, and monetized a community-first business by starting with conversations instead of a business model, and why most founders confuse audiences with real communities. Drawing on her journey from launching a social media agency to co-founding Entreprenista, she explains how trust and engagement—not follower count—determine whether a community actually works, and how to measure that through real outcomes like connections, clients, and visibility. The conversation covers practical approaches to monetization through membership tiers, founder-led power groups, and events, as well as why IRL experiences are a powerful growth engine. Courtney also shares how she evaluates opportunities as an investor, how she maintains authenticity while scaling, and why founders should build around their strengths rather than chase trends like AI. CHAPTERS 00:00 – Following vs. community: the core distinction 04:49 – From agency to Entreprenista: turning audience into business 08:23 – How to measure if a community is actually working 10:56 – Monetization: tiers, power groups, and testing models 13:15 – Transitioning post-exit and doubling down on community 14:22 – IRL events as a growth and engagement engine 17:50 – Investing and evaluating founder-led opportunities 20:25 – Building in the AI era vs. staying human-first LINKS Connect with Courtney Spritzer Entreprenista • Entreprenista LinkedIn • X/Twitter • LinkedIn • Instagram Stay Connected with Founder Mode Connect with Kevin Connect with Jason | |||
| When AI Agents Go Rogue | 02 Apr 2026 | 00:18:57 | |
EPISODE 50 Kevin Henrikson and Jason Shafton unpack the reality of working with AI agents, why they feel more “broken” than chatbots when they fail, and what it actually takes to make them useful in real workflows. They explore the shift from prompt-based interactions to autonomous systems with memory, triggers, and recurring tasks, and why expectations are often misaligned with how these systems behave. The conversation dives into the importance of guardrails, human-in-the-loop review, and treating AI like a junior employee rather than a perfect operator. They also cover the emerging dopamine loop of working with AI, how it’s changing the way people think and work, and why communication—not technical skill—is becoming the key differentiator in an AI-driven world. CHAPTERS 00:00 – Why AI agents feel more broken than chatbots 02:38 – Harness engineering, workflows, and expectations 05:50 – AI agents as employees and human-in-the-loop systems 07:25 – The dopamine loop and changing how we work 13:54 – The future of work and communication as the edge LINKS Connect with Kevin Henrikson Website • LinkedIn • X/Twitter Stay Connected with Founder Mode Stay Connected with Founder Mode Connect with Kevin Connect with Jason | |||
| The Future of AI-Built Software with Nima Keivan | 26 Mar 2026 | 00:31:32 | |
EPISODE 49 Nima Keivan joins Kevin Henrikson and Jason Shafton to break down what it takes to move AI-built software from demos into production. Drawing on his background in robotics and autonomy, Nima explains why the real challenge is not generating code but closing the “autonomy gap” between what a system can do reliably and the messy corner cases humans still have to carry. He unpacks why durable software starts with requirements, how his team approaches PRD-driven development and scenario testing, why just-in-time mocking matters when automations touch live enterprise systems, and where natural-language software building is already working versus where full end-to-end autonomy is still not ready. CHAPTERS 00:00 – The autonomy gap between demos and production 03:15 – What robotics teaches AI builders about reliability 07:32 – Why code generation is not the real bottleneck 13:18 – How Durable turns operator workflows into production software 26:32 – When natural language can actually replace writing code LINKS Connect with Nima Keivan Durable • LinkedIn • X/Twitter Stay Connected with Founder Mode Stay Connected with Founder Mode Connect with Kevin Connect with Jason | |||
| The End of Prompt Engineering with Dennis Pilarinos | 19 Mar 2026 | 00:33:03 | |
EPISODE 48 Dennis Pilarinos joins Kevin Henrikson and Jason Shafton to unpack what AI in software development actually looks like beyond the demos, arguing that the real bottleneck is not code generation but context. Drawing on his experience building Buddybuild, working inside Apple, Amazon, and Microsoft, and now leading Unblocked, Dennis explains why source code alone is not enough for either engineers or AI agents to succeed, how historical decisions buried in Slack, Jira, and docs shape production-safe software, where AI-generated code breaks down in legacy systems, what traits matter most when hiring in an AI-native era, and why the workflows teams rely on today, including pull requests, may look very different in the near future. CHAPTERS 00:00 – Why AI coding tools fail without context 04:03 – Building Unblocked to solve the missing layer in engineering 12:11 – Where AI-generated code breaks in real production environments 20:33 – Hiring for curiosity, ownership, and success in an AI-native world 27:18 – Founder lessons from aviation, uncertainty, and staying grounded LINKS Connect with Dennis Pilarinos Unblocked • LinkedIn • X/Twitter Stay Connected with Founder Mode Connect with Kevin Connect with Jason | |||
| AI Agents Are the New Employees | 12 Mar 2026 | 00:27:22 | |
EPISODE 47 In Episode 47 of Founder Mode, Kevin Henrikson and Jason Shafton unpack why AI agents should no longer be thought of as simple tools, but as a new kind of workforce that founders can hire, coach, evaluate, and orchestrate. They explore how the founder role is shifting from building and doing toward designing systems, managing agent workflows, and making the judgment calls that still require human trust, taste, and strategic thinking. Along the way, they discuss AI-first operating habits, what this means for hiring and team design, why small teams may become dramatically more powerful, where human oversight still matters most, and why the real moat in an AI-native world is not the agents themselves but distribution, proprietary workflows, and unique data. CHAPTERS 00:00 – The founder’s job has changed 00:32 – AI agents as a new staffing model 06:29 – What AI-first workflows look like in practice 16:48 – Hiring and scaling in the age of agents 24:06 – The new moat: data, workflows, and distribution LINKS Connect with Founder Mode Stay Connected with Founder Mode Stay Connected with Founder Mode Connect with Kevin Connect with Jason | |||