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 closes with location and personal-brand ...

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 y...

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...

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 bef...

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. Th...

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 al...

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...

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 m...

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.

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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 ...

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, ...

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...

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, br...

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. ...

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...

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 colo...

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...

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...

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 publ...