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

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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

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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

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

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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

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Aviation News Talk • LinkedIn • X/Twitter

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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

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sleke.io • Instagram • X/Twitter

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EPISODE 36

Kevin and Jason sit down with Scout cofounder Tim Barnes to rethink how founders raise capital in an AI-first world. Tim breaks down why most startups overlook trillions in available non-dilutive funding, how AI can automate painful proposal and compliance workflows, and why grants should function as a continuous business development engine—not a last-minute scramble for runway. They explore how climate, deep-tech, and healthcare companies can reposition their work to match shifting federal priorities without losing their mission, how Scout is helping both startups and government agencies modernize the funding ecosystem, and why founders should pursue grants before equity to validate traction and retain ownership. Tim also shares how he thinks about defensibility as foundation models advance, when to integrate grants into a capital strategy, and what it takes to keep founders focused on building instead of pitching.

CHAPTERS

00:00 – Why non-dilutive funding matters

01:00 – Rethinking fundraising and bootstrapping in an AI hype cycle

05:30 – How Scout uses AI to unlock and manage grants

10:00 – Packaging your mission for shifting policy without losing focus

16:00 – When to use grants vs equity and how Scout’s fit check works

LINKS

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Scout • LinkedIn • X/Twitter

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EPISODE 35

Kevin and Jason sit down with Healthcare AI Guy founder Max Drescher to unpack how AI is actually changing healthcare, from front-desk voice automation and AI scribes to clinical decision tools and consumer apps that give people more ownership of their data. Max shares how a habit of writing internal M&A news briefs at UnitedHealth turned into a fast-growing newsletter and community, why distribution has become one of the most important forms of founder leverage, and what separates real impact from hype in today’s healthcare AI boom. They dig into the rise of tools that reduce burnout and administrative friction, explore longevity, Blueprint-style protocols, and digital twins, and look ahead to a near future where AI-powered biology and smarter clinical support reshape medicine long before fully autonomous AI doctors arrive.

CHAPTERS

00:00 – Why AI + health now

06:30 – Max’s path from M&A to Healthcare AI Guy and the power of distribution

12:10 – What’s real vs hype in healthcare AI for providers and patients

18:30 – Longevity, Blueprint, and founders getting serious about sleep

22:00 – The next five years of AI in health and where it’s all headed

LINKS

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Healthcare AI Guy • LinkedIn • X/Twitter

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EPISODE 34

In this episode, Kevin and Jason break down how founders can turn conferences from low-ROI distractions into high-leverage growth engines. Fresh off a major healthcare event in Nashville, they unpack why most networking fails, how Pretty Good AI turned a platinum sponsorship into a full activation with mini-golf and meeting pods, and the systems that converted casual foot traffic into hundreds of real customer conversations. They dig into founder-mode presence, team ownership, pre-work, follow-up, and the small details that make an event actually move the business forward.

CHAPTERS

00:00 – The Value of Networking Events

01:25 – Challenges of Traditional Networking

02:47 – Reevaluating Event Participation

03:27 – Executing a Successful Conference Strategy

04:24 – Planning for a Major Conference

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