Founder Mode

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 clos...

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 fas...

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...

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 “...

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 fo...

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 k...

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 losi...

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 e...

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 operator...

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 tack...

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 “LifeOp...

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 metapho...

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...

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 prod...

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 Hollywoo...

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 bef...

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 wri...

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...

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...

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 a...

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...

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, f...

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 re...

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 highligh...

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...