Founder Mode

EPISODE 70

Kevin and Jason go guest-free for a wide-ranging conversation about what happens when AI starts sounding like you, posting for you, and filling up your inbox. They open by admitting they ran this very episode through an AI video podcast generator and got back a 31-minute clip where neither of them blinked once, then dig into the dead internet theory and why Kevin's real objection isn't that the internet is dead but that it was never trustworthy to begin with — including the moment he discovered more than half of what Perplexity was feeding his research agent came from scraper sites. From there they get practical: why founder thought leadership almost always fails on time rather than talent, the four ways to run it without writing every post yourself, why going viral off a Sam Altman hook produces friends texting you instead of pipeline, and the uncomfortable truth that your actual buyer may be a physician standing at a hot desk logged in under somebody else's name. The back half turns to the mess AI leaves behind — the rise of the "agent inbox," an agent that apologized for taking the weekend off, and why both of them default to the most expensive model available and treat the bill as tuition rather than overhead.

CHAPTERS

00:00 – The $200 brain

00:40 – We made an AI version of this podcast

02:39 – The dead internet theory

04:39 – When Perplexity poisons your own research

05:49 – Watermarks, fingerprints, and who owns your writing

06:55 – Founder thought leadership: worth the time?

09:26 – Four ways to do it without doing it all yourself

12:00 – The rise of the course boi

14:31 – Fish where the fish are

17:11 – The agent inbox

20:49 – Token maxing

25:01 – Founder Mode top five

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EPISODE 70

Kevin and Jason go guest-free for a wide-ranging conversation about what happens when AI starts sounding like you, posting for you, and filling up your inbox. They open by admitting they ran this very episode through an AI video podcast generator and got back a 31-minute clip where neither of them blinked once, then dig into the dead internet theory and why Kevin's real objection isn't that the internet is dead but that it was never trustworthy to begin with — including the moment he discovered more than half of what Perplexity was feeding his research agent came from scraper sites. From there they get practical: why founder thought leadership almost always fails on time rather than talent, the four ways to run it without writing every post yourself, why going viral off a Sam Altman hook produces friends texting you instead of pipeline, and the uncomfortable truth that your actual buyer may be a physician standing at a hot desk logged in under somebody else's name. The back half turns to the mess AI leaves behind — the rise of the "agent inbox," an agent that apologized for taking the weekend off, and why both of them default to the most expensive model available and treat the bill as tuition rather than overhead.

CHAPTERS

00:00 – The $200 brain

00:40 – We made an AI version of this podcast

02:39 – The dead internet theory

04:39 – When Perplexity poisons your own research

05:49 – Watermarks, fingerprints, and who owns your writing

06:55 – Founder thought leadership: worth the time?

09:26 – Four ways to do it without doing it all yourself

12:00 – The rise of the course boi

14:31 – Fish where the fish are

17:11 – The agent inbox

20:49 – Token maxing

25:01 – Founder Mode top five

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EPISODE 69

Kevin and Jason go solo for an episode that started as a walk-and-talk and turned into a working session on leverage. Kevin opens with the "subject line trick," his habit of dropping an email subject into Claude and letting it read the whole thread before drafting a reply, and walks through three real uses of it: auditing a contractor's invoice line by line, catching two billing errors his accounting team missed, and generating a negotiation email so aggressive he hesitated to send it on a $20,000 lead gen deal. From there, the conversation turns to the new break-even math. Software is nearly free to build now, so Kevin argues founders should stop raising money to prove something they can prove themselves for $200 a month and a basic laptop, and stop advertising contracted ARR that never reaches the bank. Jason breaks down the week he blocked off for a Bill Gates-style think week and ended up shipping instead, including an iOS app built in a day and a new operating model he calls the forward-deployed marketing engineer, a marketer who builds a campaign end-to-end in Claude or Cursor and submits a PR the engineering team just reviews and ships. They close on team mechanics, Feelings Friday, and whether you can actually have it all, with a story about three generations waiting in a car outside a college dorm.

CHAPTERS

00:00 – Cold open: you're not even willing to bet on yourself

01:35 – The subject line trick

02:12 – Three real examples: invoices, billing errors, and a $20K negotiation

06:00 – The new break-even math: why raise if software is nearly free?

08:40 – The VC anti-pattern and contracted ARR fantasy math

12:24 – Break-even math in services

15:06 – The think week that became a ship week

17:03 – The forward-deployed marketing engineer

19:29 – Year zero to Fortune 50 with AI video

21:09 – Your best people are still smarter than AI

23:19 – Feelings Friday and how to run the team meeting

25:33 – Can you have it all?

31:25 – Top five Founder Mode takeaways

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EPISODE 68

Jason Cohen has spent decades building companies including WP Engine, and nearly 20 years writing practical advice for founders at A Smart Bear. In this episode, he joins Kevin and Jason to unpack his new book, Hidden Multipliers, out August 10th, and the case that growth comes from a few well-chosen moves rather than more hustle. He explains why most things are going poorly most of the time even when a company is winning, and how a handful of small pricing and packaging changes at WP Engine in January 2012 took the business from one million to five million in ARR in a single year. He walks through the profit whale, the shape that shows why a small slice of customers drives most of your profit and why you can afford to spend twenty times more to acquire them, and he reframes the unprofitable tail as a product problem rather than a customer problem. He pushes back hard on the idea that people cancel over price, argues that churn sets a hard mathematical ceiling on how big any company can get, and lays out exactly how to run customer interviews that produce real answers instead of confirmation. The conversation closes on why he has no funnel, no cohort, and no master class, and why the work is better because it never had to make money.

CHAPTERS

00:00 – It can't be the price

00:44 – Hidden multipliers and the case for leverage

01:38 – Why founders reach for paid ads too early

03:28 – Confusing effort with progress

06:07 – The camera comes into focus: WP Engine's pricing change

08:25 – The profit whale and your most valuable customers

11:47 – Every support call is a gift

13:44 – What your champion actually wants

15:25 – Inciting events and the real shape of a market

18:49 – The red herring of price and the growth ceiling

22:01 – How to interview customers without leading the witness

24:15 – It's not a funnel, it's a craft

26:54 – Where to find the book

LINKS

Get the book, out August 10th

Hidden Multipliers • Free AI Skills

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EPISODE 67

Anthony Ng Monica built and exited a global retail-tech company operating in forty countries, and in this episode he tells Kevin and Jason what that decade cost him and what he learned fixing it. He walks through the scrappy tactics that won his first enterprise clients with no network or funding, including a baby-sized football shirt that got him a meeting with John Lewis, then opens up about the breaking point: letting go of three co-founders, firing twenty people, and relocating countries in twenty-four hours, followed by nine months of seven-day weeks that ended with an empty barbell giving him an instant headache and an MRI that came back clean. From there the conversation becomes a practical playbook for founders who treat health as an afterthought, covering why he calls health rent rather than equity, why fitness was a genuine competitive advantage when only his fittest employees were left standing after thirty-six-hour Black Friday shifts, why you should buy a great bed before another tracker, and his gearing system for staying consistent instead of chasing the perfect plan and repeatedly falling back to Plan F.

CHAPTERS

00:00 – The breaking point: an empty barbell and a clean MRI

03:32 – Winning first customers with no network or funding

06:22 – Why health is rent, not equity

09:55 – Buy a bed, not another tracker

12:22 – Fitness as a founder's competitive advantage

14:56 – Stop chasing Plan A, stop falling to Plan F

18:12 – The gearing system: dialing effort one to five

19:34 – Simple systems to start this week

LINKS

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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

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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

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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

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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

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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

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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

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