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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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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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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