Founder Mode

Kevin Henrikson and Jason Shafton
  • 5.0 (3)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Founder Mode is a podcast for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.

  1. When AI Agents Go Rogue

    2D AGO

    When AI Agents Go Rogue

    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 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. CHAPTERS 00:00 – Why AI agents feel more broken than chatbots 02:38 – Harness engineering, workflows, and expectations 05:50 – AI agents as employees and human-in-the-loop systems 07:25 – The dopamine loop and changing how we work 13:54 – The future of work and communication as the edge LINKS Connect with Kevin Henrikson Website • LinkedIn • X/Twitter Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

    19 min
  2. The Future of AI-Built Software with Nima Keivan

    MAR 26

    The Future of AI-Built Software with Nima Keivan

    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 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. CHAPTERS 00:00 – The autonomy gap between demos and production 03:15 – What robotics teaches AI builders about reliability 07:32 – Why code generation is not the real bottleneck 13:18 – How Durable turns operator workflows into production software 26:32 – When natural language can actually replace writing code LINKS Connect with Nima Keivan Durable • LinkedIn • X/Twitter Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

    32 min
  3. The End of Prompt Engineering with Dennis Pilarinos

    MAR 19

    The End of Prompt Engineering with Dennis Pilarinos

    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 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. CHAPTERS 00:00 – Why AI coding tools fail without context 04:03 – Building Unblocked to solve the missing layer in engineering 12:11 – Where AI-generated code breaks in real production environments 20:33 – Hiring for curiosity, ownership, and success in an AI-native world 27:18 – Founder lessons from aviation, uncertainty, and staying grounded LINKS Connect with Dennis Pilarinos Unblocked • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

    33 min
  4. AI Agents Are the New Employees

    MAR 12

    AI Agents Are the New Employees

    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 require human trust, taste, and strategic thinking. Along the way, they discuss AI-first operating habits, what this means for hiring and team design, why small teams may become dramatically more powerful, where human oversight still matters most, and why the real moat in an AI-native world is not the agents themselves but distribution, proprietary workflows, and unique data. CHAPTERS 00:00 – The founder’s job has changed 00:32 – AI agents as a new staffing model 06:29 – What AI-first workflows look like in practice 16:48 – Hiring and scaling in the age of agents 24:06 – The new moat: data, workflows, and distribution LINKS Connect with Founder Mode Founder Mode Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

    27 min
  5. Bring Back BlackBerry with Kevin Michaluk

    MAR 5

    Bring Back BlackBerry with Kevin Michaluk

    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 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. CHAPTERS 00:00 – The “people phone” idea: why Communicator won’t compete with iPhone 04:14 – From CrackBerry to builder: compounding reps and community advantage 06:56 – Naming a category: Communicator as a purpose-built device, not a smartphone 18:58 – CES momentum: how storytelling and launch mechanics are engineered early 21:43 – Bootstrapping, community funding, and avoiding the Kickstarter failure loop LINKS Connect with CrackBerry Kevin Clicks • LinkedIn • X/Twitter Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

    36 min
  6. Modernizing Prenups with Ronke Oyekunle

    FEB 26

    Modernizing Prenups with Ronke Oyekunle

    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 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. CHAPTERS 00:00 – Why prenups can reduce the odds of divorce 03:30 – From taboo to empowerment: modern money conversations in relationships 05:42 – Neptune’s model: vertical AI plus human family-law experts 12:06 – The clauses that matter most: spousal support, “what if” scenarios, and pet custody 19:05 – Beyond prenups: estate planning, “financial legal concierge,” and the future of the category LINKS Connect with Ronke Oyekunle Neptune • LinkedIn Promo code: RONKE100 ($100 off any Neptune services) Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

    26 min
  7. When Enough is Enough with Jason Fried

    FEB 19

    When Enough is Enough with Jason Fried

    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

    49 min
  8. Scaling Multi-Location Businesses with Stephanie Joyce

    FEB 11

    Scaling Multi-Location Businesses with Stephanie Joyce

    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 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. CHAPTERS 00:00 – People first, systems second: what breaks when you scale 04:25 – Documentation, SOPs, and onboarding for multi-location consistency 04:56 – Acquisition diligence: margins, concentration risk, and key-person dependency 08:06 – Leading through crisis: transparency, trust, and cash discipline 14:13 – The modern med spa playbook: systems, CRM, and incentives LINKS Connect with Stephanie Joyce attunemedspa.com • LinkedIn Stay Connected with Founder Mode Subscribe to our newsletter: gofoundermode.com Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

    25 min
See All (50)

Ratings & Reviews

5
out of 5
3 Ratings

About

Founder Mode is a podcast for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.

Information

  • Creator
    Kevin Henrikson and Jason Shafton
  • Years Active
    2025 - 2026
  • Episodes
    50
  • Rating
    Clean
  • Copyright
    © Kevin Henrikson and Jason Shafton
  • Show Website
    Founder Mode

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