EPISODE 32
Founder Mode sits down with Natalie Kaminski of JetRockets to cut through AI hype in software development. Natalie shares findings from a five-month experiment using code assistants: top engineers see ~30% efficiency on tedious tasks, but AI can duplicate components, forget context, and mislead juniors who can’t evaluate output. She argues developers matter more than ever—AI augments, not replaces—while real value comes from problem definition, secure architecture, and disciplined human review. Tools help with migrations, boilerplate, and tests; judgment, clarity, and empathy still decide what ships.
CHAPTERS
00:00 – There’s no “I” in today’s AI
03:30 – Do developers still matter?
04:51 – AI as augmentation: the calculator analogy
06:41 – Workable AI: migrations, boilerplate, tests (~30% gain)
19:08 – Where AI breaks: duplication, lost context, human review
LINKS
Connect with Natalie Kaminski
jetrockets.com • LinkedIn • X/Twitter
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EPISODE 31
In this live Founder Mode episode recorded at Workshop in San Francisco, Jason and Kevin sit down with two of the most influential builders in modern tech — Max Mullen, Co-Founder of Instacart, and Andrew Ofstad, Co-Founder of Airtable. They share never-before-heard founding stories, from Instacart’s $20K Trader Joe’s hack to Airtable’s first prototype built entirely in local storage. The conversation spans early lessons in scrappy product development, balancing speed and craft, scaling company culture, leadership evolution, and founder burnout. They also dive into how AI is reshaping startup building, what makes SF’s comeback real, and their most contrarian lessons from a decade of creating category-defining companies.
CHAPTERS
0:00 – Welcome to Founder Mode Live
2:00 – Backing the Cybertruck into Workshop
4:25 – The $20K Trader Joe’s Story
9:45 – Building Instacart’s First Catalog
10:58 – Airtable’s Early Browser-Only MVP
15:32 – Speed vs. Craft: Product Tradeoffs
22:18 – Scaling Culture and Leadership
29:10 – Founders on AI, Product, and Speed
35:44 – Burnout, Balance, and Founder Longevity
42:36 – SF’s Comeback and Final Lessons
LINKS
Connect with Max Mullen
maxmullen.com • LinkedIn • X/Twitter
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EPISODE 30
Microsoft product leader Sangya Singh joins Jason and Kevin to unpack how to decide what to ship first in AI and automation. She shares a “strategy to win” playbook (fall in love with the problem, define the hypothesis, then hire and build), why agility must be daily not monthly, and how Microsoft balances agentic and deterministic systems—highlighting a risky-but-breakthrough bet on self-healing RPA. The crew contrasts outputs vs. outcomes, explores eval-driven prioritization, and talks scale mechanics inside Microsoft. Sangya closes with what’s next: voice-based AI surfaces that discover what to automate and “mech-interrupt” style safety tooling so enterprises can see, govern, and correct model behavior.
CHAPTERS
00:00 – Cold open: “Say no to great”
00:28 – MVPs and sequencing in the AI era
03:45 – Sangya’s path & “strategy to win”
10:40 – Self-healing RPA and outcomes over outputs
25:35 – What’s next: AI surfaces & safety
LINKS
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EPISODE 29
Private equity meets AI in a grounded, operator-first conversation with Jason Friedrichs of AEA Elevate. We cover why “no-regrets” initiatives and clear ROI gates beat hype cycles, how to build an AI-first value creation plan, and why team design—not just capital—drives repeatable growth. Jason shares his thoughts on where PE playbooks are shifting beyond spreadsheets, the small wins that compound across functions (GTM, support, back office), how to navigate macro shocks, and what sectors he believes are primed for outsized AI-enabled revenue and margin expansion.
CHAPTERS
00:00 – The “no-regrets” move
00:37 – Framing PE × AI: beyond hype to operating leverage
06:19 – ROI discipline, pilots, and budgeting for AI
15:20 – Beyond capital: the PE playbook & first 180 days
20:21 – Healthcare opportunity, macro shocks, and exits
LINKS
Connect with Jason Friedrichs
aeainvestors.com/elevate • LinkedIn
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EPISODE 28
Jason and Kevin dig into why health isn’t a solo sport—and how founders can extend their “work span” by prioritizing community, shared rituals, and better device hygiene. They cover replacing PR-chasing with longevity metrics, carving out weekly “sensorless” time to reset attention, and using an AI “board of directors” to stress-test health decisions (like peptides, CGMs, and more). Practical takeaways: find your people (gyms, classes, sauna/cold communities), schedule analog friction, and optimize for effective hours—not performative 80-hour weeks.
CHAPTERS
00:00 – Work span > hours: redefining “hard work”
00:33 – Health as community, not willpower
04:32 – Built-in community: gyms, classes, rituals
10:18 – Going “sensorless”: the off-grid reset
19:37 – An AI board of directors for your health
LINKS
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SYSTEM PROMPT
HEALTH & LONGEVITY BOARD OF DIRECTORS
A pragmatic, evidence-labeled council for healthspan, performance, and physical well‑being.
[Consensus]
[Promising]
[Speculative]
Purpose
You are a council of expert advisors serving as a personal “Board of Directors” for healthspan, performance, and physical well‑being. Each advisor is an AI persona modeled on leaders in the field (fictionalized, evidence‑based, pragmatic).
Operating Principles
Profile (Example Template)
Board Composition — Core (Always Respond)
Moderator / Systems Integrator
Synthesizes advice; resolves trade‑offs; produces unified plan & metrics.
Longevity & Preventive Medicine Physician
Focus: risk stratification, screening, lab strategy, lifespan vs healthspan trade‑offs.
Cardiometabolic & Lipid Specialist
Focus: ASCVD risk, apoB/LDL/Lp(a), CAC use, BP targets, exercise cardiology.
Endocrinology & Men’s Health
Focus: thyroid axis, insulin sensitivity, testosterone, bone density, prostate screening.
Sleep Medicine Physician
Focus: OSA screening, circadian rhythm, travel protocols, insomnia differentials.
Neuroscience & Behavior Change Advisor
Focus: habit formation, motivation, stress tools, light and temperature timing.
Performance Physiology & Strength Coach
Focus: program design, block periodization, load/volume balance, recovery rules.
EPISODE 27
Ankur Goyal joins Founder Mode to show how real teams get from AI prototype to production: build a two-click loop from user complaint to eval, treat observability as a driver of quality, and design iteration environments that connect production logs back to tests. Ankur explains why LLMs behave more like databases than CPUs, how to avoid eval fatigue by curating the 5–10 examples that matter, and why top teams re-evaluate model choices monthly. He also looks ahead to agents that can review and improve other models’ work, turning today’s manual feedback loops into scalable systems.
CHAPTERS
07:53 – Why prototypes break in production
10:22 – Iteration environments and closing the loop
12:21 – LLMs are databases, not CPUs
14:48 – Beating eval fatigue with ruthless prioritization
21:15 – Observability as a driver of quality, not uptime
25:25 – What’s next for evals, agents, and AI infra
LINKS
Connect with Ankur Goyal
usebraintrust.com • LinkedIn • X/Twitter
SPECIAL OFFER
Email ankur@braintrust.dev and mention Founder Mode to receive a special offer.
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EPISODE 26
Bobby Evans goes inversion-first on startup failure modes—from overhiring and bonus wars to vanity metrics, misaligned influencers, and shipping the wrong features. We dig into crypto betting’s realities, why credibility and payouts matter more than hype, the cost of public financialization, and how to protect thinking time, delegate, and avoid perfectionism that delays MVPs. Evans closes with location and personal-brand lessons: build where the network is and productize the founder early.
CHAPTERS
00:00 – Think time over busy calendars
06:45 – Hard-earned lessons from crypto betting
12:01 – Growth tactics that backfire
18:43 – Red flags and credibility in the space
25:22 – Location, personal branding, and founder advice
LINKS
Connect with Bobby Evans
Company X/Twitter • Personal X/Twitter
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EPISODE 25
In this episode, Metronome CEO Scott Woody breaks down how AI is rewriting the value of software—from “seats and subscriptions” to agents that do work—and why modern pricing must blend stability with upside. We cover where seat-based models break, how to design hybrid packages that align incentives (platform fee + usage/outcome), why early founders should copy the market and iterate fast, and how smart packaging reveals your ICP. Scott also looks ahead to a future where pricing and packaging become the competitive battleground across SaaS.
CHAPTERS
00:00 – AI rewrites software’s value
04:05 – From Dropbox pain to Metronome
10:06 – Hybrid pricing that aligns incentives
14:35 – Early-stage: copy market, iterate, segment
26:30 – Pricing/packaging becomes the battleground
LINKS
Connect with Scott Woody
metronome.com • LinkedIn • X/Twitter
SPECIAL OFFER
Email sales@metronome.com and mention Founder Mode to get a special offer.
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EPISODE 24
A special “best of” highlight reel from our first 20 episodes: we reframe luck as reps and compounding, warn founders about burnout’s hidden interest, and show how AI can supercharge solo building without replacing your voice. We dig into making clear asks and saying “no” to protect focus, why empathy is the real product moat, and how durable edges come from hardware + proprietary data and real-world feedback. You’ll hear scrappy GTM plays (like sub-50 sq ft kiosks and Kickstarter’s customer collision), safety-first execution from nuclear to drones, pre-LLM agents, the 80/20 (AI/human) rule for content, and why creators should monetize ownership—not just virality.
CHAPTERS
00:00 – Luck is manufactured, not given
04:30 – Anxiety as fuel, not a flaw
08:15 – Empathy as the ultimate moat
13:20 – Hacking permits to scale retail
17:45 – The 80/20 rule for AI & creators
LINKS
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EPISODE 23
In this episode of Founder Mode, John Hancock joins us to break down the gap between startup hype and reality. From building Stonks—the largest angel syndication platform on AngelList—to walking away when the mission no longer fit, John shares what he’s learned about fundraising, pivots, and rebuilding with first principles. He introduces Validate, a tool designed to help founders and “idea people” kill bad ideas fast before wasting time or money, and explains why most AI features are “better shoes, not wings.” The conversation dives into validating ideas, writing as a way to sharpen thinking, and the most common founder mistake—stopping customer conversations. John closes with the raw truth: most people shouldn’t be founders, and that’s okay.
CHAPTERS
00:36 – The hype fades: AI as leverage + anyone-can-build moment
07:42 – From Stonks to walking away: the pivot and why it didn’t fit
10:31 – Validate: kill bad ideas fast (landing pages, plans, comps)
13:46 – Don’t bolt on AI no one wants (“better shoes, not wings”)
27:07 – The uncomfortable truth about being a founder
LINKS
Connect with John Hancock
Special Offer
Email john.hancock@hey.com to get Validate free forever. John is offering this exclusive deal to Founder Mode listeners—validate your ideas quickly, save time, and avoid building what no one wants.
Cool Thing
Jason’s vibe-coded app
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EPISODE 22
In this episode of Founder Mode, Anurag Agarwalla shares his journey from leading fast-moving engineering teams at Uber to building hpy, an AI-powered platform designed to support therapists and patients in achieving better outcomes. He explains why emotional systems matter as much as technical ones, how to design for happiness without burning out, and why privacy and empathy must be foundational in mental health tech. The conversation dives into emotional intelligence, daily habits, and how AI can serve as a companion tool without replacing the human connection at the core of therapy.
CHAPTERS
00:00 – From Uber to building for happiness
05:12 – Healing the healer: AI for therapists
09:27 – Privacy and ethics in mental health tech
14:06 – Designing systems for happiness and balance
23:37 – Building tools for healthier habits
LINKS
Connect with Anurag Agarwalla
thinkhpy.com • LinkedIn • X/Twitter
Connect with hpy
LinkedIn • X/Twitter • Instagram
Special Offer
Do you go to therapy? Your next therapy session is on us. With hpy, we help clinicians help YOU reach your goals faster with better outcomes, tracking and progress. Introduce us to your therapist and if they sign up for hpy, your next session is on us. Email sales@thinkhpy.com to get started and mention Founder Mode. Are you a mental health professional and want to automate all of your admin? With hpy Pro, the first AI assistant designed specially for therapy, save up to 20 hours a week. We’re offering Founder Mode listeners an exclusive—refer a colleague and get an entire YEAR of hpy Pro free. To get registered, email sales@thinkhpy.com and mention Founder Mode.
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EPISODE 21
Hosts Kevin Henrikson and Jason Shafton go beyond the headlines to unpack the real bottlenecks that stall healthcare—and how to fix them—with consultant and operator Rebecca Shufeldt, founder of Ignite Healthcare Solutions. Drawing on her path from urgent care ops to EHR/revenue cycle leadership, Rebecca explains why go‑live is “day zero,” how her evolving “Silver Bullet” project plan keeps Athenahealth implementations aligned to payer/CMS changes, and where AI—voice intake, scheduling, eligibility, authorizations and referrals—removes administrative drag, reduces denials, and lifts patient and clinician satisfaction. The group digs into tailoring EHRs beyond “turnkey,” building clinician buy‑in, upskilling staff instead of replacing them (“Betty”), and how a flexible, female‑led team model helps practices scale without burnout while improving revenue.
CHAPTERS
00:00 – Setting the stakes: healthcare’s hidden blockers + Jason’s Heal story
02:00 – AI as a wedge: voice, eligibility & EHR‑integrated routing
05:03 – Meet Rebecca Shufeldt & Athenahealth optimization
10:19 – The “Silver Bullet” plan: go‑live is day zero
12:55 – Revenue cycle pitfalls, authorizations & upskilling the team
CONNECT WITH REBECCA
SPECIAL OFFER
Ignite Healthcare Solutions is offering a complimentary 30-minute athenahealth optimization review with our CEO for Founder Mode listeners. We’ll assess your current use of the platform, highlight quick-win opportunities to improve efficiency and revenue, and share proven strategies tailored to your organization’s goals—whether you’re a start-up, an established practice, or an MSO.: calendly.com/ignitehs/complimentary-review
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EPISODE 20
In this episode of Founder Mode, Kevin and Jason sit down with Ahad Khan, CEO of Kajabi, to unpack what it really means to be a “creator CEO” in 2025. From shifting creators’ mindsets beyond virality toward sustainable, owner-operated businesses, to finding content market fit before building products, Ahad shares actionable strategies for monetization, pricing, and using AI without losing the human touch. He also opens up about leading a global team as a post-founder CEO, honoring Kajabi’s customer-obsessed roots while implementing his own leadership cadence, and why the future belongs to entrepreneurial creators who build brands their audiences truly value.
CHAPTERS
00:00 – Why “Creator CEO” is the Future of the Creator Economy
06:51 – Building for Everyday People and Customer Obsession at Kajabi
12:55 – Content Market Fit and Monetizing Beyond Virality
17:36 – Using AI to Scale Without Losing the Human Touch
25:07 – Leadership Cadence and Work-Life Integration as a Post-Founder CEO
LINKS
Connect with Ahad Khan
SPECIAL OFFER
Email ahad [at] kajabi.com for a special offer when you sign up for Kajabi.
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EPISODE 19
Visibility isn't a vibe—it's a system. In this episode, Jason and Kevin sit down with Chris Winfield, creator, connector, and coach, to break down how founders can build an unfair advantage in an AI-saturated world. Chris shares his 80/20 rule for AI usage, why content strategy is non-negotiable in 2025, and how personal connection still beats automation. Learn how to become the go-to expert in your niche, simplify your message like Steve Jobs, and avoid falling into the “Slopbot” trap of over-AI'd content.
CHAPTERS
00:00 – The 80/20 Rule for Using AI
06:26 – Visibility Through Content and Connection
12:11 – Build Real Relationships in a Noisy Digital World
15:28 – Marketing Trends That Actually Matter in 2025
19:37 – The Real Unfair Advantage for Founders
LINKS
Connect with Chris
Special Offer
DM Chris on Instagram @chriswinfield and mention Kevin & Jason to get a special offer.
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EPISODE 18
In this candid, fast-paced solo episode, Jason and Kevin unpack the systems behind their ideal weeks, why founders should prioritize health like a product launch, and how to build a ride-or-die team that spans multiple startups. From hiding jets from repo men to wearing smart glasses on the beach, they share war stories, personal rituals, and the mindset that separates cautious operators from calculated risk-takers.
CHAPTERS
00:00 – The Casino Story That Saved FedEx
01:04 – Building Your Perfect Week
05:14 – Big Company Constraints Are (Mostly) Self-Imposed
10:00 – Health Is Your Only Asset
16:08 – Boomerangs vs. Boomer Rides
LINKS
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RESOURCES
EPISODE 17
Water‑tech pioneer Ravi Kurani explains how a floating pool‑chemistry robot became the ultimate hardware moat, why proprietary water data unlocks service marketplaces, and where trillion‑dollar opportunities lie at the water‑energy nexus. He recounts two years on Shenzhen factory floors perfecting Sutro, selling the startup before mass production, and now plotting to buy it back to tackle agriculture, cooling towers, and AI data centers. Hosts Jason Shafton and Kevin Henrikson unpack story‑driven design, founder persistence, and the future of “smart” water.
CHAPTERS
00:00 – From Pools to Robotics: Ravi’s origin story
03:44 – Hardware Moats & Proprietary Water Data
07:11 – Sutro as the “Nest Cam” for Your Pool
09:01 – Water as Tech’s Next Trillion‑Dollar Frontier
16:36 – Founder Mode in China: Two Years on the Factory Floor
LINKS
Connect with Ravi
Sutro • Liquid Assets Podcast • LinkedIn • X/Twitter
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EPISODE 16
From living two years out of a suitcase to shipping AI products at Microsoft-scale, Angus Logan joins Kevin and Jason to unpack how “failing forward” accelerates learning. He explains why product teams should break things early each morning, how to shield a fast-moving startup culture inside a corporate giant, and the importance of weekly shipping cadences. Angus also shares his “LifeOps” playbook—100 travel-buddy rules, zero checked bags, and decision templates that free up brainpower—plus how culture-soaking trips and five-year-old Android phones keep him designing for real-world users everywhere.
CHAPTERS
00:00 – Why failure is fuel
03:34 – Angus on rapid AI experimentation
06:50 – Integrating startups into Microsoft
10:58 – LifeOps: travel hacking & decision systems
18:47 – Global perspective and takeaways
LINKS
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EPISODE 15
AI builder Shuja Keen joins Kevin and Jason to trace his 20-year journey from building offshore labor forces to AI-native operations. He explains how falling bandwidth costs kicked off globalization, why today’s custom LLM agents are ready while people and processes lag, and how an abundance mindset lets founders redesign workflows instead of bolting AI onto old playbooks. Using metaphors like orthotics that adapt to your feet, Shuja shows how bespoke software, not one-size-fits-all packages, will unlock personalization in healthcare, education, and beyond—and urges founders to stop selling car parts and deliver the full “Uber” experience.
CHAPTERS
00:00 – Outcomes Over Tools: The Uber Analogy
04:31 – Onshore → Offshore → AI: Shuja’s 20-Year Lens
11:32 – Custom Software & the Abundance Mindset
17:06 – AI’s Impact on Healthcare, Education & Inclusion
21:02 – Founder Playbook for 2025
LINKS
Connect with Shuja Keen
786 Ventures • LinkedIn • X/Twitter
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EPISODE 14
In this episode of Founder Mode, we hit the gym with legendary trainer Coach Lou Perrotta—who's spent decades working with elite entrepreneurs, celebrities, and top performers. Coach Lou shares how fitness, mindset, and consistency create compounding results—both in the gym and in business. From towel pull-ups in hotel rooms to 15-minute daily routines, Kevin, Jason, and Coach Lou talk about building mental resilience, breaking plateaus, and why the best founders train their bodies as relentlessly as they train their minds.
CHAPTERS
00:00 – Why Every Founder Needs a Coach
01:05 – Coach Lou’s Origin Story
03:38 – Health is the First Investment
05:21 – Use What You Have
08:20 – Focus, Transformation, and Final Lessons
LINKS
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EPISODE 13
Kevin Henrikson and Jason Shafton sit down with serial entrepreneur Dennis Mortensen (IndexTools, Visual Revenue, x.ai, and now LaunchBrightly) to unpack what it was really like to build an AI company years before large-language models existed. Dennis recounts owning the x.ai domain before Elon Musk, hand-labeling 32 million emails to train an early scheduling agent, and the costly product-design decisions that followed. He shares hard-won lessons on focusing on pain over technology, reverse-engineering post-acquisition goals, and why parenting teenagers is the ultimate sales boot camp. Dennis then introduces LaunchBrightly, his new platform that automates every product screenshot in your help center—and he caps the chat with an exclusive free-setup offer for Founder Mode listeners.
CHAPTERS
00:00 – x.ai Before Elon
01:34 – Hand-Labeling 32 Million Emails
05:45 – Product Design > Prediction Precision
14:45 – Birth of LaunchBrightly
29:56 – Special Offer & Next Steps
OFFER
Mention “Founder Mode” when you connect with LaunchBrightly to get your first batch of up to 1,000 automated screenshot-update recipes created for free.
Connect with Dennis
LaunchBrightly • LinkedIn • X/Twitter
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