Founder Mode

EPISODE 50Kevin 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 behave. The conversation dives into the importance of guardrails, human-in-the-loop review, and treating AI like a junior employee rather than a perfect operator. They also cover the emerging dopamine loop of working with AI, how it’s changing the way people think and work, and why communication—not technical skill—is becoming the key differentiator in an AI-driven world.CHAPTERS00:00 – Why AI agents feel more broken than chatbots02:38 – Harness engineering, workflows, and expectations05:50 – AI agents as employees and human-in-the-loop systems07:25 – The dopamine loop and changing how we work13:54 – The future of work and communication as the edgeLINKSConnect with Kevin HenriksonWebsite • LinkedIn • X/TwitterStay Connected with Founder ModeStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 49Nima 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 durable software starts with requirements, how his team approaches PRD-driven development and scenario testing, why just-in-time mocking matters when automations touch live enterprise systems, and where natural-language software building is already working versus where full end-to-end autonomy is still not ready.CHAPTERS00:00 – The autonomy gap between demos and production03:15 – What robotics teaches AI builders about reliability07:32 – Why code generation is not the real bottleneck13:18 – How Durable turns operator workflows into production software26:32 – When natural language can actually replace writing codeLINKSConnect with Nima KeivanDurable • LinkedIn • X/TwitterStay Connected with Founder ModeStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 48Dennis 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 engineers or AI agents to succeed, how historical decisions buried in Slack, Jira, and docs shape production-safe software, where AI-generated code breaks down in legacy systems, what traits matter most when hiring in an AI-native era, and why the workflows teams rely on today, including pull requests, may look very different in the near future.CHAPTERS00:00 – Why AI coding tools fail without context04:03 – Building Unblocked to solve the missing layer in engineering12:11 – Where AI-generated code breaks in real production environments20:33 – Hiring for curiosity, ownership, and success in an AI-native world27:18 – Founder lessons from aviation, uncertainty, and staying groundedLINKSConnect with Dennis PilarinosUnblocked • LinkedIn • X/TwitterStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

They argue AI agents are becoming a new kind of workforce you can hire, coach, and replace. They explore AI-first workflows, agent failure modes, and where human oversight must remain. They debate agents acting autonomously in meetings and how to size tasks and coach agents. They examine hiring for agent-first skills, optimal small-team design, and how moats shift to data, workflows, and distribution.

EPISODE 46CrackBerry 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 breaks down Clicks’ strategy: validate demand with accessories first, frame Communicator as a purpose-built “people phone” category instead of a smartphone competitor, and use CES storytelling to create momentum months before launch. The conversation also digs into how Clicks approached fundraising without relying on traditional VC, leveraged community as both customers and megaphone, and avoided the classic Kickstarter trap by sequencing products, aligning supply-chain incentives, and refusing to overpromise on timelines.CHAPTERS00:00 – The “people phone” idea: why Communicator won’t compete with iPhone04:14 – From CrackBerry to builder: compounding reps and community advantage06:56 – Naming a category: Communicator as a purpose-built device, not a smartphone18:58 – CES momentum: how storytelling and launch mechanics are engineered early21:43 – Bootstrapping, community funding, and avoiding the Kickstarter failure loopLINKSConnect with CrackBerry KevinClicks • LinkedIn • X/TwitterStay Connected with Founder ModeStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 45Ronke 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 conversations safely, and why the hardest clauses, like spousal support and even pet custody, often end up strengthening relationships rather than undermining them. The conversation also expands beyond prenups into estate planning and the idea of Neptune as a “financial legal concierge” for couples, ending with Ronke’s vision for an AI-plus-humans future and a promo code for the Founder Mode audience.CHAPTERS00:00 – Why prenups can reduce the odds of divorce03:30 – From taboo to empowerment: modern money conversations in relationships05:42 – Neptune’s model: vertical AI plus human family-law experts12:06 – The clauses that matter most: spousal support, “what if” scenarios, and pet custody19:05 – Beyond prenups: estate planning, “financial legal concierge,” and the future of the categoryLINKSConnect with Ronke OyekunleNeptune • LinkedInPromo code: RONKE100 ($100 off any Neptune services)Stay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

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. The conversation explores designing with human-scale constraints borrowed from the physical world (like piles on a desk), why limits often produce better tools, and how 37signals stays independent to preserve optionality. They also discuss why 40 hours a week is enough, how founders can stay deeply involved without becoming bottlenecks, and Jason’s advice to new founders: keep your surface area small and start making something real as fast as possible. CHAPTERS 00:00 – Building software as objects you want to use every day 07:04 – Fizzy and a simpler, more joyful take on Kanban 12:21 – Piles, limits, and designing for human scale 22:03 – 40 hours is enough: founder involvement without micromanagement 43:22 – Undercomplicating year one: keep surface area small and start making LINKS Connect with Jason Fried 37signals.com • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter: gofoundermode.com Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

EPISODE 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 into the modern med spa operating stack, from CRM and automation to compensation structures that drive the right behaviors, and why the future of wellness will be defined by better data, smarter technology, and a careful balance between AI and human trust.CHAPTERS00:00 – People first, systems second: what breaks when you scale04:25 – Documentation, SOPs, and onboarding for multi-location consistency04:56 – Acquisition diligence: margins, concentration risk, and key-person dependency08:06 – Leading through crisis: transparency, trust, and cash discipline14:13 – The modern med spa playbook: systems, CRM, and incentivesLINKSConnect with Stephanie Joyce attunemedspa.com • LinkedInStay Connected with Founder ModeSubscribe to our newsletter: gofoundermode.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 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 depends on pairing that window with therapy and lifestyle medicine fundamentals like sleep, nutrition, movement, and stress management. They also cover the myths around expensive wellness biohacks, how AI could reduce administrative burden and expand patient access, and what Jay learned scaling from a one-person launch to multiple MindWell locations.CHAPTERS00:00 – Ketamine as a fast-acting “open window” for change00:50 – Health fundamentals that matter most: sleep, food, movement04:20 – Why Jay left anesthesiology: autonomy, loss, and control of time07:10 – Building MindWell: ketamine + therapy + lifestyle medicine19:10 – Scaling the clinic: cash-pay vs insurance, systems, and hiringLINKSConnect with Dr. Jay Motley mindwell.com • LinkedIn • Instagram • X/Twitter • Substack • FacebookStay Connected with Founder ModeSubscribe to our newsletter: gofoundermode.comConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 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 without clean data, perfect timing, or consensus.CHAPTERS00:00 – Why the same founder problems keep repeating01:01 – Go live is not the finish line01:42 – Teaching interpersonal skills too late02:34 – Adding AI before earning user trust03:17 – When users reject AI and features get rolled back03:57 – Why pricing complexity grows with mature markets04:34 – Busyness as avoidance for founders05:14 – Protecting thinking time before the business outgrows you05:55 – Turning user complaints into learning fast06:33 – Building a personal board of directors for health07:27 – AI as a problem-solving lever, not a starting point08:20 – Governance as the unlock for enterprise AI adoption08:20 – When “magic” becomes table stakes for customers09:10 – Why software being cheaper doesn’t make it easier09:59 – Hybrid aviation as a trust bridge to electrification10:51 – Measuring whether conference presence actually works11:38 – Why AI scribes exploded in healthcare adoption12:28 – Defaulting to venture capital and silent dilution12:28 – Designing products that force focus and community13:06 – Stress, judgment, and risk in aviation13:43 – Unlimited pricing as a math problem13:43 – Learning faster by removing safety nets14:31 – Making decisions when there is no right answerLINKSStay Connected with Founder ModeStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter