EPISODE 72

No guest and no notes on Jason's side, so Kevin runs the board for once. The two dig into the question underneath every pricing decision: what unit of value are you actually selling? Jason retraces underpricing his agency in the early days and the shift from billing hours to building productized services with near-zero marginal cost, while Kevin walks through losing a deal to a competitor selling raw phone minutes, where the buyer admitted the product was worse and bought it anyway. From there they get into using AI to reconcile invoices against vendor spend down to the penny, a sweep that turned up 23 fraudulent charges and an education in BIN enumeration. They cover the strange state of the market, where a public company doing $275M gets taken private at 2x forward revenue while venture-backed startups raise at 100x. And they close on the AI back office: Kevin's 76 scheduled agents, the 13 supervisor agents he built to watch them, and the eight days of automations that reported success, success, success while quietly writing results to a directory that didn't exist.

CHAPTERS

00:32 – No guest, no notes: a solo episode

00:51 – What unit of value are you actually selling?

02:24 – "I did what most people do and I underpriced"

04:26 – Losing a deal to phone minutes

08:50 – Letting AI reconcile your invoices and vendor spend

12:41 – 23 fraud charges and BIN enumeration

15:02 – Weave goes private: 2x revenue vs. 100x rounds

17:09 – The private and public markets dance

19:21 – 76 agents, 13 supervisors, and "successfully failing"

21:57 – Most people are bad managers

25:34 – DHH's Linux distro and talking to your OS

26:50 – 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 71

Jess Chan built Longplay from an email and SMS agency into a strategic growth partner that has helped more than a hundred e-commerce brands generate hundreds of millions in revenue, and then she handed over the CEO title. In this episode she explains why, and makes the case that the hardest decisions in business are the ones nobody claps for. She talks about letting lucrative client relationships drift on purpose, taking pay cuts, and flatlining revenue for two years to fix the foundations, because a hockey stick for one year often means out of business in three. She breaks down her diagnostic approach to lifecycle marketing and why most people are solving the wrong problem extremely fast and extremely well, describes what she learned building a seven figure agency during the least profitable stretch of her business, and shares the moment she realized a company is like a kid who eventually has to stand on its own. Kevin and Jason open with Kevin's first startup, an embroidery business run out of a one bedroom apartment near UCLA, and the navel gazing loop every early founder falls into. Jess also gets into why she thinks she is better off than Elon Musk, why hurt people hurt people applies to founders more than anyone, the real trade-offs between agency and SaaS after building both, and how she uses AI to buy back space instead of running yesterday's playbook faster.

CHAPTERS

00:00 – Cold open: the founders whose companies become their jobs

01:05 – Henriksen Embroidery, LLC and the navel gazing trap

04:46 – What playing the long game actually means

06:26 – Turning down money on purpose

07:54 – Handing over the CEO title

10:52 – Why email was never the real problem

12:55 – Most people are solving the wrong problem

14:34 – The seven figure agency that wasn't profitable

17:04 – Success, balance, and why Elon sounds miserable

18:35 – Hurt people, hurt people, and that includes founders

20:15 – Agency vs SaaS: choose your hard

23:03 – What AI is great at and what still needs humans

25:37 – Using AI to buy back space

27:46 – The Founder Mode Top Five

LINKS

Connect with Jess Chan

Longplay • 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 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

STAY CONNECTED

Subscribe to the Founder Mode newsletter

CONNECT WITH KEVIN

LinkedIn • X/Twitter

CONNECT WITH JASON

LinkedIn • X/Twitter

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