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

Connect with Jason Cohen

asmartbear.com • LinkedIn • X/Twitter

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

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

Connect with Anthony Ng Monica

Website • LinkedIn • Instagram

Special offer for Founder Mode listeners

Stay Connected with Founder Mode

Subscribe to our newsletter

Connect with Kevin

LinkedIn • X/Twitter

Connect with Jason

LinkedIn • X/Twitter

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

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

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

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

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

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

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

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