Founder Mode

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

EPISODE 18In 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.CHAPTERS00:00 – The Casino Story That Saved FedEx01:04 – Building Your Perfect Week05:14 – Big Company Constraints Are (Mostly) Self-Imposed10:00 – Health Is Your Only Asset16:08 – Boomerangs vs. Boomer RidesLINKSConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/TwitterRESOURCESMeta Ray Ban WayfarerTune Up FitnessMyo

EPISODE 17Water‑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.CHAPTERS00:00 – From Pools to Robotics: Ravi’s origin story03:44 – Hardware Moats & Proprietary Water Data07:11 – Sutro as the “Nest Cam” for Your Pool09:01 – Water as Tech’s Next Trillion‑Dollar Frontier16:36 – Founder Mode in China: Two Years on the Factory FloorLINKSConnect with RaviSutro • Liquid Assets Podcast • LinkedIn • X/TwitterStay Connected with Founder ModeSubscribe to our newsletter: foundermode.kit.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter