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

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LinkedIn • X/Twitter

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LinkedIn • X/Twitter

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

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LinkedIn • X/Twitter

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LinkedIn • X/Twitter

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 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.

CHAPTERS

00:00 – Ketamine as a fast-acting “open window” for change

00:50 – Health fundamentals that matter most: sleep, food, movement

04:20 – Why Jay left anesthesiology: autonomy, loss, and control of time

07:10 – Building MindWell: ketamine + therapy + lifestyle medicine

19:10 – Scaling the clinic: cash-pay vs insurance, systems, and hiring

LINKS

Connect with Dr. Jay Motley

mindwell.com • LinkedIn • Instagram • X/Twitter • Substack • Facebook

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LinkedIn • X/Twitter

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LinkedIn • X/Twitter

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 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.

CHAPTERS

00:00 – Why the same founder problems keep repeating

01:01 – Go live is not the finish line

01:42 – Teaching interpersonal skills too late

02:34 – Adding AI before earning user trust

03:17 – When users reject AI and features get rolled back

03:57 – Why pricing complexity grows with mature markets

04:34 – Busyness as avoidance for founders

05:14 – Protecting thinking time before the business outgrows you

05:55 – Turning user complaints into learning fast

06:33 – Building a personal board of directors for health

07:27 – AI as a problem-solving lever, not a starting point

08:20 – Governance as the unlock for enterprise AI adoption

08:20 – When “magic” becomes table stakes for customers

09:10 – Why software being cheaper doesn’t make it easier

09:59 – Hybrid aviation as a trust bridge to electrification

10:51 – Measuring whether conference presence actually works

11:38 – Why AI scribes exploded in healthcare adoption

12:28 – Defaulting to venture capital and silent dilution

12:28 – Designing products that force focus and community

13:06 – Stress, judgment, and risk in aviation

13:43 – Unlimited pricing as a math problem

13:43 – Learning faster by removing safety nets

14:31 – Making decisions when there is no right answer

LINKS

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LinkedIn • X/Twitter

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LinkedIn • X/Twitter

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 platform, and how racing schools function as the entry point to professional motorsport. The conversation draws clear parallels between racing and building companies: managing risk without automation, carrying momentum through corners, and knowing where the limits actually are.

CHAPTERS

00:00 – Growing up with racing and early influences

01:05 – Driving formula cars at Laguna Seca

02:52 – Racing as a model for building companies

05:40 – Building and operating a racing school

09:44 – Advice for founders building niche businesses

LINKS

Connect with Allen Berg

Allen Berg Racing Schools • LinkedIn

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LinkedIn • X/Twitter

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LinkedIn • X/Twitter

EPISODE 39

Jonathan Sturgeon joins Founder Mode to explain how he built multiple eight-figure businesses without chasing an audience, a personal brand, or social media validation. He breaks down his deliberately anti-influencer posture, why cold calling still outperforms content for high-intent sales, and how his companies Dingus & Zazzy and Uh Oh scale through systems, scripts, and trust rather than hype. The conversation moves from trolling internet fame culture to designing a radically simple IT business with a free trial and pay-what-you-want pricing, and ends with Jonathan’s view that not every project needs to optimize for returns—some are worth doing because they’re fun.

CHAPTERS

00:00 – Building businesses without social media or an audience

03:45 – The anti-influencer mindset and trolling internet fame

11:45 – Cold calling, scripts, and why outbound still works

15:30 – Uh Oh: free-trial IT, pay-what-you-want pricing, and trust

24:00 – Art over profit and building businesses for enjoyment

LINKS

Connect with Jonathan Sturgeon

Uh Oh • Dingus & Zazzy • LinkedIn • X/Twitter

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LinkedIn • X/Twitter

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LinkedIn • X/Twitter

EPISODE 38

Recorded mid-flight in Kevin’s Vision Jet en route to Monterey, Kevin and Jason talk with veteran pilot and aviation podcaster Max Trescott about why flying can feel like a flow-state reset, and how the discipline of aviation maps to building companies. Kevin shares his path from earning a pilot’s license in college to taking a long break, then returning to aviation with structured training, checklists, and the calm that comes from repetition. Together they unpack why “it’s not hard, it’s a lot of effort,” why SOPs and emergency prep matter when things break, and the real key to learning: consistent time in the seat, the right instructor, and a focus on proficiency over deadlines.

CHAPTERS

00:00 – Flying as a stress reset and the “are you ready?” check

00:48 – Welcome to Founder Mode from the Vision Jet

02:55 – Kevin’s pilot journey: college license to getting hooked on the Vision Jet

05:23 – The founder/pilot overlap: effort, SOPs, and staying calm when things change

13:09 – Buying (and upgrading) a jet: the sales cycle, timing, and “right message, right moment”

LINKS

Connect with Max Trescott

Aviation News Talk • LinkedIn • X/Twitter

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LinkedIn • X/Twitter

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LinkedIn • X/Twitter

EPISODE 37

Kevin and Jason sit down with Austin Boer, co-founder of Sleke, to unpack what it takes to build a “dumb phone” that still supports modern life. Austin shares how a simple insight from the r/dumbphone subreddit shaped Sleke’s mission: people want fewer distractions, not less utility. The conversation covers founder-led customer discovery, why Sleke is built around intentional constraints like banning infinite scroll, and how the team balances privacy, usability, and real-world needs like QR codes, maps, and music. They also explore the bigger question of what replaces the phone by 2030 and why digital minimalism should be accessible to everyone, not a luxury product.

CHAPTERS

00:00 – The dumb phone problem people actually have

03:50 – Why Austin built Sleke and what the product is

04:30 – Founder-led discovery: 200+ ICP calls and shifting ICP

08:20 – The “fatal flaw” of dumb phones and preventing app creep

16:30 – Digital minimalism shouldn’t be a luxury

LINKS

Connect with Austin Boer

sleke.io • Instagram • X/Twitter

Special Offer: Use code FOUNDERS5 for a discount on a Sleke device.

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LinkedIn • X/Twitter

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LinkedIn • X/Twitter