Shows
Founder ModeScaling Multi-Location Businesses with Stephanie JoyceEPISODE 43Kevin 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...
2026-02-1125 min
Frank GrowthHow to Write Like a Human with Steve DennisEpisode #206: Steve Dennis — How to Write Like a Human in the Age of AIAI can generate endless copy. The new bar is making someone feel something.This episode is for founders, marketers, and anyone who writes for a living and wants their work to connect.Steve Dennis is a writer and ghostwriter who has shaped voices the world knows—including Andy Puddicombe at Headspace. Jason and Steve go back to the Headspace days, where Steve helped define the brand voice and coached writers (including Jason) on how to sound human on the page. In t...
2026-02-1020 min
Founder ModeFrom Doctor to Founder with Jay MotleyEPISODE 42Kevin 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...
2026-02-0525 min
Frank GrowthFrom Audience to Community with Jordan DiPietroEpisode #205: Jordan DiPietro — How to Turn an Audience Into a Community That Compounds GrowthMost companies stop at audience. This episode shows you how to build community that creates its own pipeline.For founders and operators who want retention, not just reach.Jordan DiPietro has built audience-to-community flywheels at The Motley Fool, The Hustle (inside HubSpot), and as CEO of Hampton. In this conversation, he breaks down the specific systems Hampton used to vet members—including raising the revenue threshold from $1M to $3M and personally reviewing every applicant video. He explains why trust comp...
2026-02-0315 min
Founder ModeBest of Founder Mode IIEPISODE 41After 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...
2026-01-2914 min
Frank GrowthI Hate Sales with John KennellyEpisode #204: John Kennelly — Founders who hate sales still have to sellIf sales feels intrusive, this episode reframes it as problem-solving.Built for founders avoiding sales calls, decks, and outreach.John Kennelly, Founder of I Hate Sales, works with founders who have never had a sales job and actively avoid selling. In this episode, he explains why sales fear is usually a mindset problem, not a skill gap, and why curiosity matters more than persuasion. The conversation covers running discovery without pitching, qualifying people out quickly, and why early founders slow themselves down by bu...
2026-01-2720 min
How to Scale an 8 Figure Agency 🚀AI for Agency Growth: Building a Marketing Holding Company with Automation & DiversificationUNLOCK THE 13 SYSTEMS EVERY AGENCY OWNER NEEDS TO REACH 8 FIGURES:https://bit.ly/41Sm05NIn this episode, Jordan Ross sits down with Jason Shafton, founder of Winston Francois, to unpack how to build a modern marketing agency holding company in the age of AI. From automating agency operations to diversifying revenue through holding structures, they break down what it takes to lead in a world where AI is no longer optional — it's the new baseline.Jason shares how he went from leading growth at Google to building a future-ready consultancy using AI-powered sy...
2026-01-2623 min
Founder ModeMove Fast & Brake Things with Allen BergEPISODE 40Recorded 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...
2026-01-2213 min
Frank GrowthAcquisitions and Inorganic Growth with Trevor HoughtonEpisode #203: Trevor Houghton — How to buy growth without risking cashHow founders use acquisitions to grow without betting the company.For operators considering their first inorganic deal.Trevor Houghton is CEO of Pass Galleries and a former private equity and corporate development operator. He breaks down how founders can use acquisitions to increase enterprise value without overextending capital. The conversation covers how deals actually get sourced, why most failed acquisitions start with the wrong premise, and how Trevor structures transactions using debt, seller notes, and earn-outs to reduce downside. He walks through a concrete ex...
2026-01-2010 min
Founder ModeUh-Oh Everything's Broken with Jonathan SturgeonEPISODE 39Jonathan 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...
2026-01-1528 min
Frank GrowthHow Investors Think About Growth with John ConnollyJohn Connolly - Make your growth story hold up in investor diligenceHow to present growth so it is defensible, measurable, and scalable.For founders raising and operators building board-ready growth reporting.John Connolly is a Managing Director at Spectrum Equity, and he explains what he expects to see when a company tells a growth story at the growth equity stage. He covers why founders often stop at simplified metrics instead of going deep on channels, cohorts, and what is actually repeatable. John breaks down two common issues he...
2026-01-1314 min
Founder ModeFrom Flight Deck to Front Line with Max TrescottEPISODE 38Recorded 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 t...
2026-01-0820 min
Frank GrowthBuilding Your Growth Operating System with Cait AndersonEpisode #201: Cait Anderson — Building trust into a repeatable growth systemTrust breaks faster than funnels.This episode is for operators trying to make growth predictable without killing speed.Cait Anderson is Chief Marketing Officer at Winston Francois. In this conversation, she and Jason unpack what actually makes a growth system sustainable: predictable returns, clear operating rhythm, and trust that compounds instead of resets. They walk through concrete examples, including a B2B SaaS company spending $1M/month in paid media, how experimentation budgets are set at different stages, and why breaking a...
2026-01-0618 min
Founder ModeSimple Design is Best with Austin BoerEPISODE 37Kevin 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 minima...
2025-12-1820 min
Founder ModeFuture of Fundraising with Tim BarnesEPISODE 36Kevin 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 pu...
2025-12-1124 min
Founder ModeAI, Health & Home with Max DrescherEPISODE 35Kevin 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 th...
2025-12-0428 min
Founder ModeWhen Founders Show UpEPISODE 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 Va...
2025-11-2031 min
Founder ModeElectrifying Aviation with Kevin NoertkerEPISODE 33Kevin 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 d...
2025-11-1335 min
Founder ModeWill AI Replace Developers with Natalie KaminskiEPISODE 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...
2025-11-0623 min
Founder ModeFounder Mode Live at San Francisco Tech Week with Max Mullen (Instacart) & Andrew Ofstad (Airtable)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 r...
2025-10-3046 min
Founder ModeAI + Automation: What to Ship First with Sangya SinghEPISODE 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 tooli...
2025-10-2330 min
Founder ModePrivate Equity + AI with Jason FriedrichsEPISODE 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”...
2025-10-1626 min
Founder ModeHealth Is a Team SportEPISODE 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 c...
2025-10-0923 min
Founder ModeFrom AI Prototype to Production with Ankur GoyalEPISODE 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....
2025-10-0230 min
Founder ModeHow Not to Run a Startup with Bobby EvansEPISODE 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 th...
2025-09-2530 min
Founder ModeRight-Price Your SaaS with Scott WoodyEPISODE 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 s...
2025-09-1835 min
Founder ModeBest of Founder Mode IEPISODE 24A 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 w...
2025-09-1119 min
Founder ModeFrom Stonks to AI for Everyone with John HancockEPISODE 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 thinki...
2025-09-0430 min
Founder ModeBuilding Happiness with Anurag AgarwallaEPISODE 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.
2025-08-2835 min
Founder ModeThe Healthcare Innovation Bottleneck with Rebecca ShufeldtEPISODE 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 “turnk...
2025-08-2127 min
Founder ModeThe Creator CEO with Ahad KhanEPISODE 20In 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 t...
2025-08-1433 min
Founder ModeThe Founder’s Unfair Advantage with Chris WinfieldEPISODE 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...
2025-08-0724 min
Founder ModePerfect Days With Your Ride-Or-DiesEPISODE 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...
2025-07-3122 min
Founder ModeWater, The Next Frontier with Ravi KuraniEPISODE 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 origi...
2025-07-2424 min
Founder ModeFail Forward with Angus LoganEPISODE 16From 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.CHAPTERS00:00 – Wh...
2025-07-1724 min
Founder ModeOnshore to Offshore to AI with Shuja KeenEPISODE 15AI 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”...
2025-07-1024 min
Founder Mode15-Minute Workout with Lou PerrottaEPISODE 14In 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.CHAPTERS00:00 – Why Every Founder Needs a Coach0...
2025-07-0314 min
Founder ModeBuilding AI Before It Was Cool with Dennis MortensenEPISODE 13Kevin 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...
2025-06-2631 min
Founder ModeFrom Hollywood to High-Rises: Making Robots with Asa HammondEPISODE 12From 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 t...
2025-06-1123 min
Founder ModeThe Future of Commerce: Product Design & Logistics with Samantha RoseEPISODE 11From 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...
2025-06-0325 min
Founder ModeHow to Bootstrap Your Tech Team Using AI with JJ ZhuangEPISODE 10Serial 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 founder...
2025-05-2727 min
Founder ModeDe-Risking Brick-and-Mortar for DTC Brands with Megan BerryEPISODE 9Megan 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.CHAPTERS00:00 – Permit Hack & Pop...
2025-05-2030 min
Founder ModeAI-First Product Design with Ritwik PavanEPISODE 8In 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.CHAPTERS00:34 – What It Means to Build AI-First03:53 – Ritwik’s Journey and AI Consumer Innovations08:41 – Smart Cities...
2025-05-1328 min
Founder ModeZero-to-One Marketing with Peter FaragoEPISODE 7In 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.
2025-05-0631 min
Predictable B2B SuccessB2B Growth Marketing: The Ultimate CEO Playbook for Building Resilient, High-Performing Tech BrandsIn this episode of Predictable B2B Success, we dive into the mind of a true growth marketing maestro, Jason Shafton. With over two decades of experience scaling giants like Google, Paramount, and Headspace, Jason reveals the secrets behind crafting killer marketing strategies that defy the status quo. From his journey of personal resilience, including the poignant stories of overcoming profound personal challenges, Jason shares how authenticity and vulnerability can transform business narratives and inspire teams to achieve the impossible.
We explore how brutal honesty, balanced with empathy, can foster environments where teams thrive and deliver exceptional...
2025-04-3046 min
Founder ModeRemote Boundaries – Saying No Without Burning Bridges with Viktor PeterssonEPISODE 6In 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.CHAPTERS00:00 – Why Saying No Matters for Remote Teams02:23 – Setting Boundaries and Avoiding Burnout09:12 – Remote Work Fundamentals & Hiring15:18 – O...
2025-04-2928 min
Founder ModeThe Power of Asking with Andreas HomerEPISODE 5In 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 yo...
2025-04-2229 min
Founder ModeAnxiety is a Superpower if You Channel It with Slobodan "Sani" ManićEpisode 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...
2025-04-0827 min
Founder ModeAI & The Future of SaaS with Alex FinnEpisode 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 ex...
2025-04-0129 min
Slow Down To Speed Up#019: Saying No When Everyone Needs You [Jason Shafton]Jason Shafton, founder and CEO of Winston Francois, wrestles with the challenge every entrepreneur-parent knows too well: how to build a thriving business while being fully present for family. After experiencing a profound personal loss, Jason's perspective on work transformed, yet he still struggles with the "always on" mentality. In this coaching session, we explore how perfectionism and the need to be needed keep notifications perpetually active, preventing true presence anywhere. Discover practical steps toward becoming "dad by default" instead of "working by default."Enjoyed this episode? Ready to take your leadership and personal growth t...
2025-03-3146 min
Founder ModeThe Hard Truth About Health & Hustle: You Can't Have it AllEpisode 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...
2025-03-2530 min
Founder ModeLuck is a Skill - You Can Manufacture ItEpisode 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 le...
2025-03-1446 min
The First CustomerThe First Customer - Marketing, Momentum, and Making It Work with CEO and Founder Jason ShaftonIn this episode, I was lucky enough to interview Jason Shafton, CEO and founder of Winston Francois.Jason shares his journey from growing up in a family of entrepreneurs in Chicago to becoming a growth and marketing consultant for tech startups. Inspired by his parents’ business ventures in high-end audio equipment, Jason developed an early passion for business, launching a small airplane-selling stand as a child and later a record label in high school. His career took him from Google to leadership roles at Comedy Central, Headspace, and various startups before organically transitioning into consulting. What began as...
2025-02-1919 min
Voices of Search // A Search Engine Optimization (SEO) & Content Marketing PodcastThe best ways to effectively measure SEOJason Shafton, Founder and CEO of Winston Francois, delves into SEO for growth marketing. Measuring SEO’s effectiveness can be a challenge for growth marketers. Unlike other marketing channels with clear-cut key performance indicators (KPIs), SEO's impact is multifaceted and its results often require patience and time to bear fruit. Today Jason discusses the best ways to effectively measure SEO. Connect With: Jason Shafton: Website // LinkedInThe Voices of Search Podcast: Email // LinkedIn // TwitterBenjamin Shapiro: Website // LinkedIn // TwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
2025-02-1116 minVoices of Search // A Search Engine Optimization (SEO) & Content Marketing Podcast5 things growth marketers need to understand about SEOJason Shafton, Founder and CEO of Winston Francois, delves into SEO for growth marketing. Effective growth marketing strategies leverage multiple channels, and SEO and content marketing are two levers that growth marketers can pull to achieve scale. However, understanding SEO's unique qualities is key to leveraging its potential. Today Jason discusses five things growth marketers need to understand about SEO.Connect With: Jason Shafton: Website // LinkedInThe Voices of Search Podcast: Email // LinkedIn // TwitterBenjamin Shapiro: Website // LinkedIn // TwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
2025-02-1021 min
Experts SpeakGrowing Your Business and Family with Jason ShaftonJason Shafton is an expert at growth for tech companies. Listen to this insightful interview and you will understand how you can apply those same principles to your company. Jason and I also touch on the importance of building a strong family as you were building your business. This is a really good interview that you should listen to Learn more about Jason at his website.
2024-12-0423 min
Legends N LeadersJason Shafton, CEO of Winston Francois, on the right techniques for brands to market today!Jason has held major marketing roles at Google, Headspace, Comedy Central, Soothe, and more and decided to build his own venture to help brands truly realize their marketing potential! Winston Francois was born and has now helped so many companies tell their stories in a manner that can get major traction while being authentic in nature.
Jason discusses how his passion for marketing began, what he learned most in the world of tech company marketing, and when it was the right time to venture out on his own! He also discusses the best techniques to communication as...
2024-10-2220 min
2024-10-1319 min
YES, BRAND with Hersh RephunJason Shafton on Growth Strategies, Comedy, and Work-Life Balance
Hersh's guest today is Jason Shafton, Founder & CEO of growth, product and marketing firm Winston Francois. His spirited journey spans Google, Headspace, Paramount, dozens of startups...and the comedy world. His hand in life includes incredible ups and downs, losses and blessing, and he generously shares his story with us on the show.
Jason Shafton is a 20+ year veteran in growth, where he built billion-dollar businesses at Google, Paramount, and DaVita and scaled startups like Headspace, Soothe, and Heal (acquired by Humana). At Google, he scaled the Google Ads platform and launched Google Music and Google Play. He also...
2024-09-0525 min
YES, BRAND with Hersh RephunJason Shafton on Growth Strategies, Comedy, and Work-Life BalanceHersh's guest today is Jason Shafton, Founder & CEO of growth, product and marketing firm Winston Francois. His spirited journey spans Google, Headspace, Paramount, dozens of startups...and the comedy world. His hand in life includes incredible ups and downs, losses and blessing, and he generously shares his story with us on the show.
Jason Shafton is a 20+ year veteran in growth, where he built billion-dollar businesses at Google, Paramount, and DaVita and scaled startups like Headspace, Soothe, and Heal (acquired by Humana). At Google, he scaled the Google Ads platform and launched Google Music and Google Play. He also...
2024-09-0525 min
Frank GrowthHow to Fix Healthcare and Other Bad WordsWelcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they interview Hank and Carly Schlissberg. Hank is the CEO of Evio Pharmacy Solutions, and Carly is a stay-at-home mom to their three daughters. Hank and Carly discuss their experiences as parents and entrepreneurs, sharing insights on managing time, setting priorities, and finding balance. They emphasize the importance of hiring exceptional people and prioritizing what truly makes a difference. Hank discusses how aligning incentives in the healthcare industry is key to growing...
2024-08-3047 min
Remarkable Marketing PodcastHow to Create a Category-Leading BrandUnlock the secrets to transforming a struggling business into a category-leading brand with our special guest, Jason Shafton, head of the growth consultancy Winston-Francois. Jason takes us through his impressive journey of revitalizing a European e-commerce company from a seven-figure monthly loss to profitability by meticulously optimizing marketing channels and operations. Learn how identifying inefficiencies and implementing best practices can drive exponential growth. Jason also shares a pivotal moment from his career at Google, where he played a key role in launching Google Music, underscoring the necessity of robust products and structured growth experimentation for effective marketing....
2024-08-1514 min
Lets Have This ConversationBuilder and Storyteller for Products Which Improve People’s Lives with Jason Shafton
Having vision and discipline in business means having a game
plan for acceleration and the patience to see it through. When you have the
ambition to start a startup business, establishing clarity is key. According to
the Center for American Progress, the number of startups—firms that are under 1
year old—increased by 16 percent between 2019 and 2023, which is more than 2
1/2 times the 2015–2019 growth rate of 6 percent. Importantly, the number did
not fall noticeably in 2020 and 2021, so the surge is not simply making up for
pandemic-era losses. Jason Shafton is a 20+ year veteran in growth, where he
buil...
2024-08-0230 min
Tech Bytes - Software Growth & StrategiesEp. 380: Growth Marketing Like the Big Boys - with Jason ShaftonJason Shafton is a 20+ year veteran in growth, where he built billion-dollar businesses at Google, Paramount, and DaVita and scaled startups like Headspace, Soothe, and Heal (acquired by Humana). At Google, he scaled the Google Ads platform and launched Google Music and Google Play. He also spent time leading marketing at Comedy Central, where he launched new seasons of South Park and The Daily Show as well as new franchises Broad City, Drunk History and Inside Amy Schumer.
In this episode, we dive deep into the world of growth marketing with industry expert Jason Shaftin, founder of...
2024-07-2929 min
Frank GrowthUp All Night To Get LuckyWelcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they interview Brian and Sam Rose, husband and wife duo and partners in Mvnifest, a single platform to manage your commerce operations, from concept to customer. Brian and Sam met in college and have been growing businesses and people together for nearly 20 years. They share their approach to parenting, business, and creating an environment of fun and generosity of spirit. They are no strangers to a late night and have created their...
2024-07-2654 min
The WLD ShowJason Shafton: Building Growth Consulting Firm Winston Francois to Help Founders with Growth and Marketing | #134Jason Shafton is the founder of Winston Francois, a growth consulting firm. Winston Francois helps helps founders, executives, and investors with growth, product, and marketing. Prior to Winston Francois, Jason was the VP at Vively Health, VP of Marketing at Headspace, and Chief Marketing Officer at Soothe. Jason was also the co-founder of Heal, providing access to primary care doctors through a simple app. In this episode, we talk about Jason's career and gave him the perfect experience to build a growth consulting firm for founders.
2024-07-2559 min
Frank GrowthFrom Vegas to HomeLifeWelcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they interview Jessica and Marshall Morris, husband and wife duo and partners in HomeLife brands. They discuss the importance of relationships in business and parenting and the need to understand and support individuality. They also share their approach to parenting, which involves following their children's passions and providing guidance without stifling their creativity and independence. Jessica and Marshall Morris also share their resilience journey and how they have built businesses with impact...
2024-06-2827 min
Frank GrowthFather's Day Special: Uncommon Dad TruthsWelcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this special Father’s Day episode, Jason flies solo and interviews Nick Aubin, the co-founder and CEO of Commons Clinic, about his experience as a dad and an entrepreneur. They discuss the challenges of balancing work and family life, the importance of being present and proactive as a parent, and the joy of watching their children grow and succeed. Nick shares his insights on the healthcare industry and the mission of Commons Clinic to pr...
2024-06-1438 min
Frank GrowthTake a Trip on the OthershipWelcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox explore the intricacies of business and personal growth. In this episode, they engage in a fascinating conversation with Robbie and Emily Bent, the visionary co-founders of Othership. Othership is not just a platform, it's a transformative concept that combines a physical space and a mobile app. It's a solution to the pervasive issue of loneliness, offering a path to improved individual and collective health. Othership's unique approach fosters a sense of awe, belonging, and interconnectivity, enriching the human experience and leading to a...
2024-05-311h 04
Frank GrowthGrowing a Business and PeopleWelcome to Frank Growth, the podcast where husband and wife duo Jason Shafton and Alyssa Fox delve deep into the complexities of business and personal growth. In episode one, Jason and Alyssa open up about the intricacies of balancing work, life, and parenthood. They talk about some of the advice they have gotten that was “total bullshit,” and share the unique and creative way they decided to celebrate the birth of their second child. It may have involved a 20-person shoot, and burgers being thrown in people’s faces. Watch Motherhood is Hot! Youtube @WinstonFrancois.
2024-04-3024 minVoices of Search // A Search Engine Optimization (SEO) & Content Marketing PodcastThe Best Ways To Effectively Measure SEOJason Shafton, Founder and CEO of Winston Francois, delves into SEO for growth marketing. Measuring SEO’s effectiveness can be a challenge for growth marketers. Unlike other marketing channels with clear-cut key performance indicators (KPIs), SEO's impact is multifaceted and its results often require patience and time to bear fruit. Today Jason discusses the best ways to effectively measure SEO. Connect With: Jason Shafton: Website // LinkedInThe Voices of Search Podcast: Email // LinkedIn // TwitterBenjamin Shapiro: Website // LinkedIn // TwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
2024-04-1816 minVoices of Search // A Search Engine Optimization (SEO) & Content Marketing Podcast5 Things Growth Marketers Need To Understand About SEOJason Shafton, Founder and CEO of Winston Francois, delves into SEO for growth marketing. Effective growth marketing strategies leverage multiple channels, and SEO and content marketing are two levers that growth marketers can pull to achieve scale. However, understanding SEO's unique qualities is key to leveraging its potential. Today Jason discusses five things growth marketers need to understand about SEO.Connect With: Jason Shafton: Website // LinkedInThe Voices of Search Podcast: Email // LinkedIn // TwitterBenjamin Shapiro: Website // LinkedIn // TwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
2024-04-1721 min
Consulting Success PodcastThe Simple Method For Growing Your Consulting Business With Jason Shafton: Podcast #305
Growing your business may not be easy but you can look at the successful people around you and learn from them. One of those that you’ll find invaluable is this episode’s guest, Jason Shafton, the Founder of Winston Francois. Drawing not only from his experience and expertise but also insights learned from the amazing people around him, Jason shares the simple method for growth in your consulting business. He dives deep into the value of getting referrals and how to get them without directly asking for them, the secret to winning new clients (and no, it’s not your...
2023-08-2844 min