Founder Mode

Kevin Henrikson and Jason Shafton

5.0 (3)
Entrepreneurship
Updated Weekly

Founder Mode is a podcast for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.

5d ago

You Are The Bottleneck

EPISODE 66 No guest this week, just Kevin and Jason locking the door to run a live diagnostic on their own companies. The prompt: name the single bottleneck that sets the speed for everything else, then rethink it from first principles instead of from inside the tools you already pay for. Across founder-led sales, high-ticket enterprise deals, AI video, and AI hiring, every constraint lands in the same neighborhood: trust, permission, and what people will actually accept. Along the way they dig into firing your "demon" customers, why product-market fit is becoming product-customer fit in the AI era, why frontline job applicants actually prefer AI interviews, the compliance walls slowing AI video for Fortune 500 brands, and why the only credential that survives AI is showing the work you did. CHAPTERS 00:36 – Bottlenecks and first principles: running the test live 01:32 – Founder-led sales: "the bottleneck is me" 05:35 – Trust, referrals, and firing your demon customers 09:31 – From product-market fit to product-customer fit 12:46 – Why job applicants actually like AI interviews 14:21 – AI video, avatars, and testing at scale 18:25 – Healthcare, trust, and what people will accept 22:47 – Hiring: show the work, not the resume BOOK MENTIONED Angel Customers and Demon Customers: Discover Which Is Which and Turbo-Charge Your Stock by Larry Selden and Geoff Colvin LINKS Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Jul 16

Default Alive Without VC Money

EPISODE 65 On this episode, hosts Kevin Henrikson and Jason Shafton flip to the other side of the ledger: the unsexy operational and financial decisions that actually determine what a founder walks away with. Instead of product and growth, they trade hard-won notes on cap tables and the operating agreement nobody reads, why the goal is to grow the pie rather than fight over the slice, and how to structure entities the right way from day zero, from Delaware LLCs and C corps to Stripe Atlas, QSBS, and 83(b) elections. From there they weigh selling versus compounding, make the case for building an acquisition-ready data room on day one, and dig into the mindset Kevin now optimizes for above all: optionality and staying default alive. They close on where you live and what state taxes are really worth, why relocating purely to save on taxes usually backfires, and what the money is ultimately for, including using a donor-advised fund to give before the windfall. No theory, just two founders comparing notes on decisions they're living through. Nothing in this episode is legal or tax advice. CHAPTERS 00:00 – Cold open: the freedom of optionality 01:26 – The operating agreement nobody reads 02:35 – Grow the pie, don't fight over the slice 04:25 – Delaware, LLCs, and Stripe Atlas 06:22 – QSBS and setting up for the exit 07:21 – Selling vs. compounding and your "number" 08:16 – Build the data room from day zero 10:29 – Optionality and staying default alive 12:23 – Where you live: state taxes and the "weather tax" 16:08 – What it's all for: giving before the windfall 19:07 – Founder Mode Top Five: Ownership Edition Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Jul 9

Better Or Just Busier?

EPISODE 64 In this guest-free Founder Mode episode, Kevin and Jason run through five stories from the last thirty days to answer one question: is AI actually making your company better, or just busier? They open on Anthropic's short-lived "Fable 5" model — released, jailbroken, and switched off within days — and use it to riff on why staying at the AI frontier matters. From there they get practical: how to use AI to make yourself smarter rather than drowning your team in unread 30-page docs, why "show me where I'm wrong" beats getting glazed by a model that always agrees with you, and where things stand in the AI layoff cycle now that a $200-a-month subscription can act like an employee. Jason lays out his four levels of AI adoption — from treating it like Google up to a swarm of agents working while you sleep — and predicts level five will split companies into two classes. They close with Jason's confession (an AI outbound campaign that booked meetings, recorded podcasts, and made zero dollars, while a warm referral closed in eight days), the case for consulting-as-SaaS, and the founder's real job: firing yourself from every role and figuring out which one you should actually be playing this week. The throughline — the best model doesn't win, the best-organized company does. CHAPTERS 00:00 – Intro: Better or Just Busier? 00:43 – The AI Anthropic Gave, Then Switched Off 02:56 – Using AI to Get Smarter, Not Just Busier 07:41 – The $200 Employee and the AI Layoff Cycle 12:02 – The Four Levels of AI Adoption 14:44 – Consulting as SaaS: Context Is the Unlock 17:38 – The Confession: Zero Dollars vs. a Referral in 8 Days 19:56 – Firing Yourself From Every Job 22:47 – Recap and the Founder Mode Top Five LINKS Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Jul 2

Fake AI vs Real AI

EPISODE 63 Kevin and Jason go solo for a no-guest, no-filter breakdown of everything that happened to them in the past week. Kevin recaps the call center conference where one simple question, "What's your stack?", exposed an industry of companies bolting AI onto decades-old businesses, including one whose "AI" turned out to be an outsourced team manually shipping WAV files back and forth. From there they get to the real thesis: the money in AI isn't in building the brain (the foundation models) but in building the nervous system that wires that intelligence into unglamorous, real-world businesses. They dig into why taste and error correction are the durable moat, two practical on-ramps for any company trying to go AI-native, pointing agents directly at business KPIs, and Jason's full stack for turning client calls into interactive proposals. They close on the strange new category of "renting humans," why the marginal cost of everything is heading toward zero, and why the human premium, like live shows, real conversations, and white-glove service, only goes up from here. CHAPTERS 00:54 – "What's your stack?" The conference that exposed fake AI 04:16 – Build the nervous system, not the brain 07:24 – Why taste and error correction are the real moat 10:08 – How to go AI-native (or credibly bolt it on) 15:38 – Pointing AI agents at your KPIs 17:03 – Jason's full AI proposal stack 21:43 – Renting humans and the new AI category 23:55 – Abundance, robots, and the rising human premium 28:39 – The Founder Mode Top Five LINKS Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Jun 25

Be A Cockroach, Not A Unicorn with Sahib Anandsongvit

EPISODE 62 Sahib has built from zero, survived chaos, and lived to tell the unvarnished version. In this episode he traces a path from hosting Airbnb guests at his family hotel to building a multi-million-dollar services marketplace in Thailand, then pivoting through Web3 and into AI. He explains the "cockroach mindset" — why chasing unicorn status is the biggest myth and mistake a founder can make, and why the ability to get beaten to the ground and wake up to fight another day matters more than any valuation. Along the way he shares how he landed his first customers with no product (a makeup artist sourced from his girlfriend's contacts, a housekeeper in a borrowed black t-shirt), why the supply side is the hard part of any marketplace, how the company survived COVID and reached an exit on roughly $400K raised while better-funded competitors raised millions and died, and why distribution, narrative, and radical honesty about your losses are the real moats today. It's a refreshingly direct take on resilience over hype. CHAPTERS 00:00 – The unicorn myth vs. the cockroach mindset 06:12 – From hotel rooms to a services marketplace 09:04 – Landing your first ten customers with no product 12:39 – What the cockroach mindset means in practice 16:26 – Surviving COVID and reaching the exit 17:55 – The pivot into Web3 and crypto 20:25 – Why distribution, narrative, and community win now 23:04 – Being real: owning your losses, not just your wins 27:08 – The VC trap and the mismanagement of funding LINKS Connect with Sahib Website • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Jun 18

Don't Build On Rented Land with Joe Speiser

EPISODE 61 In this episode, Hampton co-founder and co-CEO Joe Speiser joins Kevin and Jason to unpack the lessons behind a career of 10-plus startups — including the one that cost him a hundred-million-dollar outcome almost overnight when Facebook changed its news feed. Joe explains why every business comes down to finding the arbitrage, why "building on rented land" without a strong brand is the trap that still keeps him up at night, and how he turned a single ICP tweak — a community built only for young, high-growth tech founders — into an entirely new business. He also opens up on the human side of running Hampton ("we just organize humans"), why he caps growth and turns away revenue to protect quality, and how he rolled AI agents out across his 25-person team after his own vibe-coded version "just sucked." The throughline: stop building outside your core competency, treat AI like your smartest friend, and bet on the arbitrage nobody else is looking at. CHAPTERS 03:36 – Find the arbitrage: why every business has one 05:16 – The $100M loss and "building on rented land" 07:52 – "We just organize humans": Hampton as a human business 09:45 – Selling betterment and keeping bad actors out 14:55 – The single ICP tweak that created a new business 18:23 – Going deep on AI agents (and why his own build failed) 22:50 – Getting non-technical teams to actually adopt AI 27:09 – The solo-founder, billion-dollar company myth LINKS Connect with Joe Speiser Hampton • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Jun 11

Best of Founder Mode III

EPISODE 60 In this Best Of compilation, Kevin and Jason revisit the standout moments from the last 20 or so episodes of Founder Mode and surface a clear pattern: the founders breaking through aren't chasing the shiny new thing, they're doubling down on fundamentals like trust, services, and picking up the phone, then using AI to do more of it. From Jay reframing how ketamine works in modern mental health care, to Jason Fried's 26-year run of profitability without a board seat, to Jose building a business by cold-calling his Carnegie Mellon alumni network, to Brent calling the next 12 months a land grab on LLM-driven discovery, to Eric Ries naming the force he spent his career fighting in Incorruptible, this batch of conversations makes the case that AI didn't replace the work, it just made it harder for the people doing it to hide. If you've been feeling like the playbook flipped upside down this year, this episode is the reset. CHAPTERS 00:00 – Welcome Back and Why This Best Of Hits Different 00:29 – Mental Health, Ketamine, and the Window of Opportunity 02:18 – Jason Fried on 26 Years of Profitability Without a Board 05:41 – Vertical AI for Couples and Where Generic AI Fails 07:05 – Bring Back Blackberry and Validating With a Landing Page 08:23 – Where Engineering Knowledge Actually Lives 11:28 – Treat AI Like an Intern, Not an Employee 14:04 – Building an Orchestrated Team of AI Agents 15:45 – Co-Pilot vs. Autopilot and the Trust Line 18:20 – The 90-Day Myth and the Chocolate Milk Signal 20:08 – How Jose Got His First 10 Customers 21:39 – The LLM and Reddit Land Grab 23:05 – Eric Ries on Incorruptible 24:11 – Why Services Revenue Is a Positive Signal 25:40 – The Pattern Across 20 Episodes LINKS Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Jun 4

AI Can't Explain What It Did with Scott Francis

EPISODE 59 Scott Francis spent nearly two decades building BP3 across mobile, cloud, automation, and now AI before stepping back to help other founders navigate the same path. In this episode, Scott unpacks why process outlasts every tech wave, even at companies like Google, and breaks down the "Turing Trap" that's fooling founders who mistake fluent AI output for actual understanding. He shares why the rebranded "forward deployed engineer" matters more than ever, why services can be a positive signal for transformative tech, and how to hire multipliers instead of black holes in the AI era. Plus, the $25K test that separates real deals from time-wasters, and what founders need to know before selling to private equity. CHAPTERS 00:00 – Cold Open: The Turing Trap 00:41 – Intro: Building Companies That Last 03:31 – Welcome Scott Francis 04:25 – Why Process Outlasts Every Tech Cycle 06:16 – Even Google Has Process Problems 09:02 – Signals It's Time to Step Away 11:05 – The Turing Trap and AI Estimation 17:35 – The Forward Deployed Engineer Rebrand 20:16 – Hiring Multipliers in the AI Era 21:30 – Why Services Is a Positive Signal 24:02 – The $25K Test for Real Deals 28:42 – What Founders Should Pay Attention To 32:07 – Advising Founders and PE Debt Overhang 35:56 – Founder Mode Top Five LINKS Connect with Scott Francis Westslope Advisors • LinkedIn • Substack Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter

5

out of 5

3 Ratings

Founder Mode is a podcast for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.

Creator

Kevin Henrikson and Jason Shafton
Years Active

2025 - 2026
Episodes

66
Rating

Explicit
Copyright

© Kevin Henrikson and Jason Shafton
Show Website

Founder Mode

Management

Management

Updated Weekly