Founder Mode

EPISODE 64 In this guest-free Founder Mode episode, Kevin and Jason run through five stories from the last thirty days to answer one question: is AI actually making your company better, or just busier? They open on Anthropic's short-lived "Fable 5" model — released, jailbroken, and switched off within days — and use it to riff on why staying at the AI frontier matters. From there the...

EPISODE 63 Kevin and Jason go solo for a no-guest, no-filter breakdown of everything that happened to them in the past week. Kevin recaps the call center conference where one simple question, "What's your stack?", exposed an industry of companies bolting AI onto decades-old businesses, including one whose "AI" turned out to be an outsourced team manually shipping WAV files back and forth. From the...

EPISODE 62 Sahib has built from zero, survived chaos, and lived to tell the unvarnished version. In this episode he traces a path from hosting Airbnb guests at his family hotel to building a multi-million-dollar services marketplace in Thailand, then pivoting through Web3 and into AI. He explains the "cockroach mindset" — why chasing unicorn status is the biggest myth and mistake a found...

EPISODE 61 In this episode, Hampton co-founder and co-CEO Joe Speiser joins Kevin and Jason to unpack the lessons behind a career of 10-plus startups — including the one that cost him a hundred-million-dollar outcome almost overnight when Facebook changed its news feed. Joe explains why every business comes down to finding the arbitrage, why "building on rented land" without a strong brand is the...

EPISODE 60 In this Best Of compilation, Kevin and Jason revisit the standout moments from the last 20 or so episodes of Founder Mode and surface a clear pattern: the founders breaking through aren't chasing the shiny new thing, they're doubling down on fundamentals like trust, services, and picking up the phone, then using AI to do more of it. From Jay reframing how ketamine works in modern mental...

EPISODE 59 Scott Francis spent nearly two decades building BP3 across mobile, cloud, automation, and now AI before stepping back to help other founders navigate the same path. In this episode, Scott unpacks why process outlasts every tech wave, even at companies like Google, and breaks down the "Turing Trap" that's fooling founders who mistake fluent AI output for actual understandin...

EPISODE 58 Eric Ries, creator of the Lean Startup methodology and author of the new book Incorruptible, joins Kevin and Jason for a conversation about what happens after a company starts working — and why success makes you a target, not safer. Eric explains why 80% of founders are no longer CEO three years after IPO, walks through the Saul Price story behind FedMart and Costco as a real A/B test i...

EPISODE 57 Brent Csutoras has spent nearly two decades inside Reddit, Digg, and the message-board underbelly of the internet - and he joins Kevin and Jason to explain why the human voice is now the most valuable thing in marketing. Brent breaks down why Reddit shows up everywhere in AI answers, the biggest mistakes brands make when they enter online communities, and how his team flipped Asurion fr...

EPISODE 56 Jose Li, founder and CEO of 71lbs, joins Kevin and Jason to break down how he turned a frustration most companies tolerate, opaque and overcharged shipping invoices, into a 14-year-old business that has saved 5,000 customers more than $80 million. After running FedEx's retail and e-commerce practice, Jose left to tackle the two biggest pain points companies face with carriers: saving mo...

EPISODE 55 Kevin and Jason tackle the three things every founder pretends they have under control: sleep, the first 90 days of taking over a company, and the say-no muscle. Kevin explains why sleep is the ultimate performance enhancing drug, then unpacks his contrarian take on the first 90 days — by week three you better have an opinion or people start writing you off. He walks through his recent...

EPISODE 54 Kevin and Jason break down why Anthropic is out of compute, why that's actually a strategy, and what it means for everyone using Claude right now. They dig into the Mythos model as the best marketing moment in AI, why artificial scarcity works, and why $200/month for Claude Max is the cheapest hire you'll ever make. Then they shift to AI in the enterprise — why one "AI Week" won't rewir...

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 age...

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 t...

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 commu...

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...

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 dura...

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 e...

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 req...

EPISODE 46 CrackBerry Kevin, founder of Clicks, explains why building hardware in a software-obsessed world is suddenly the opportunity again and how “intentional tech” is creating room for focused devices that complement, not replace, your iPhone. He shares the arc from launching CrackBerry.com and Mobile Nations to turning years of product coverage into an unfair advantage for building, then bre...

EPISODE 45 Ronke Oyekunle, co-founder of Neptune, explains how modern prenups have evolved from taboo paperwork into a structured process that helps couples talk honestly about money, values, and “what if” scenarios before marriage. She shares why millennials and Gen Z are approaching financial planning differently, how Neptune combines vertical AI with top family-law experts to guide difficult co...

EPISODE 44 Kevin Henrikson and Jason Shafton sit down with Jason Fried, co-founder of 37signals, to unpack what it means to build software that feels less like “software” and more like a physical object you actually want to use every day. Jason explains the philosophy behind Fizzy, 37signals’ fresh take on Kanban, and why speed, fluidity, and visual joy aren’t polish but core product decisions. Th...

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 am...

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 ge...

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...

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 plat...