Founder Mode

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
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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

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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

LINKS
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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

LINKS
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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

Connect with Jason Cohen
asmartbear.com • LinkedIn • X/Twitter

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