Founder Mode

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

Connect with Andrew Ofstad

LinkedIn • X/Twitter

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Connect with Kevin

LinkedIn • X/Twitter

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LinkedIn • X/Twitter

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

Connect with Sangya Singh

LinkedIn • X/Twitter

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LinkedIn • X/Twitter

Connect with Jason

LinkedIn • X/Twitter

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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Connect with Kevin

LinkedIn • X/Twitter

Connect with Jason

LinkedIn • X/Twitter

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

Stay Connected with Founder Mode

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Connect with Kevin

LinkedIn • X/Twitter

Connect with Jason

LinkedIn • X/Twitter

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

• Clarity first: short, specific bullets; quantify when possible.
• Evidence labels: [Consensus] [Promising] [Speculative]. State assumptions & uncertainty.
• Risk triage: flag red‑flags & when to escalate to in‑person care.
• Iterative: smallest high‑ROI next step; define metric & timebox experiments.
• Personalization: use known profile; if missing data, note assumptions.
• Quarterly cadence: prompt refresh of goals / labs / constraints.

Profile (Example Template)

• Demographics: adult male.
• Body composition: mid‑teens % body fat.
• Goals: reduce body fat to ~12–15%; visible abs; strong back & shoulders; high energy & sleep quality; sustainable fitness under reasonable weekly time budget.
• Cardio/Metabolic: moderate VO2 max; uses CGM for tight glucose control.
• Training: brief daily strength sessions; occasional joint/back tightness.
• Lifestyle: frequent travel; values minimalism, precision, and clear instructions.

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 [email protected] and mention Founder Mode to receive a special offer.

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Connect with Kevin

LinkedIn • X/Twitter

Connect with Jason

LinkedIn • X/Twitter

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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Connect with Kevin

LinkedIn • X/Twitter

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LinkedIn • X/Twitter

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 [email protected] and mention Founder Mode to get a special offer.

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Connect with Kevin

LinkedIn • X/Twitter

Connect with Jason

LinkedIn • X/Twitter

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 – Manufactured luck & the burnout tax05:04 – Empathy is the moat (AI changes jobs)09:49 – Safety & simplicity: nuclear-ready drones13:52 – Fail-forward roadmaps (hypotheses over hype)16:18 – AI 80/20 and the creator long tail

LINKS

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Connect with Kevin

LinkedIn • X/Twitter

Connect with Jason

LinkedIn • X/Twitter

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

vldt.ai • X/Twitter

Special Offer

Email [email protected] 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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Connect with Kevin

LinkedIn • X/Twitter

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LinkedIn • X/Twitter

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 [email protected] 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 [email protected] and mention Founder Mode.

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Connect with Kevin

LinkedIn • X/Twitter

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LinkedIn • X/Twitter