Founder Mode

Kevin Henrikson and Jason Shafton

5.0 (4)
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.

2d ago

Was Yoda Right About AI? with JJ Zhuang

EPISODE 76 JJ Zhuang, co-founder and CEO of Pretty Good AI, returns to Founder Mode to answer for the predictions he made on the show over a year ago. Kevin and Jason had Claude grade all ten, and JJ defends his record on hiring generalists over specialists, how much code AI is really writing, why taste is the one thing you can't train into a model, and why slide decks are dead when you can just build the thing. He finishes 6.5 for 10, which beats the weatherman, and points to the release of Opus 4.6 as the moment things that used to not work suddenly started working. In the second half, JJ looks ahead: why Pretty Good AI is skipping the "sell the same widget a thousand times" playbook to become the AI team for healthcare practices, how to build guardrails around AI that's confidently wrong, why the human work that's left will be 100% hard work, how the team keeps protected patient data away from AI agents, and how a lean team can win a crowded healthcare AI market. CHAPTERS 00:00 – Cold Open: Why Not Just Solve All Your Problems? 00:31 – JJ Returns: Grading 10 Predictions One Year Later 01:58 – Generalists vs. Specialists: Who Should You Hire? 04:39 – Is AI Really Writing Half of All Code? 07:28 – Taste, Comprehension, and the Human Edge 09:58 – Instant Prototypes, Fast Software, and the Death of Slide Decks 12:39 – Directing AI and the Most Overhyped Buzzword 14:32 – Overhyped or Underestimated? The Opus 4.6 Moment 17:09 – The Scorecard: 6.5 for 10 18:00 – Pretty Good AI's Big Bet: Solve Every Problem 20:02 – What Success Looks Like: Becoming Your Customers' AI Team 20:39 – Designing Around AI That's Confidently Wrong 22:20 – Where the Line Between AI and Humans Moves Next 24:09 – Building on Models That Change Every Few Months 25:58 – Compliance When Your Team Is Agents 28:23 – What Patients Notice First 30:17 – How a Lean Team Wins a Crowded Market LINKS Connect with JJ Zhuang Pretty Good AI • LinkedIn • X/Twitter Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Sep 24

The $1 CRM Killer

EPISODE 75 Kevin and Jason go solo on the week AI stopped asking permission. Jason opens with a Claude Code session that sent a Slack message to a client's CEO instead of drafting it, complete with a "sent from Claude" tag at the bottom, then offered to file a bug report about itself. That kicks off a run through what founders are actually paying for now: Jason's $800-a-month HubSpot bill and his plan to swap it for Dharmesh Shah's $1-a-month USpot, levels.io running a multi-million-dollar business on hand-coded PHP and a single server, and why the "SaaSpocalypse" is more nuanced than Twitter thinks. Kevin traces the freemium playbook back to Zimbra, where 98% of users never paid and the top 2% funded the company, and asks the question that hangs over the whole episode: how do you build trust in a market where everything can be free? They also get into Jason's agentic agency experiment, why succession is really about handing off jobs rather than titles, why nobody has built a marketing agent with taste yet, and the biological age scores every app is suddenly handing out, each one conveniently favoring its own algorithm. CHAPTERS 00:00 – The Slack message Claude sent by itself 00:39 – A dozen AI tools in a single day 03:46 – $800 a month for a CRM 04:26 – Dharmesh's $1 CRM and the SaaSpocalypse 08:03 – Freemium after vibe coding: the Zimbra lesson 10:32 – Building an agentic agency 13:20 – Succession: hand off jobs, not titles 16:33 – What AI still can't do in marketing 19:18 – Biological age scores and walled-garden health data 22:22 – 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
Sep 17

The Fursuit of Happiness with Kiko Zang

EPISODE 74 Kiko Zang spent more than half her life pretending to be someone else — born in China, sent alone to boarding school in New Zealand at 12, then to USC at 17, then back to China as the Chinese-looking person who couldn't hold an adult conversation in Chinese. Pretending, as she puts it, was a survival instinct that became one of her strongest skills. In this episode she traces that pattern from the classroom in China where she refused to rehearse a fake PTA lesson, through the years of self-censoring at work, to the full head-to-toe mascot costume she wore around crypto conferences — where, strangely, the expectations placed on a female founder vanished and she got to be more herself than she was without it. Now CEO of Chomp, she's building an app around the gap between what people say in public and what they actually believe in private, and she brings the receipts: 50,000 users, two million answers, and a question about saying "I love you" in the first month of dating that came back 93% green flag when nobody was watching — while every single player assumed it would be a coin flip. Kevin and Jason play a live pack on air, and the conversation moves into why honest human opinion may be the most valuable data set of the AI era, why there's no durable moat in consumer, and what Kiko learned after a co-founder breakup when her own team had to tell her she'd been muting herself in meetings. Her conclusion: the fear felt true not because it was real, but because she believed it was. CHAPTERS 00:00 – More herself inside the suit 00:40 – Know your audience or know yourself 04:07 – Half a life spent pretending 06:14 – The PTA rehearsal that got her sent abroad 08:34 – The reluctant founder 11:44 – The fursuit and who gets assumed to be the founder 14:05 – Anonymity, honesty, and shared reality 16:12 – Playing Chomp live 19:24 – 93% green flag and the perception gap 22:20 – Pluralistic ignorance and why consumer has no moat 24:31 – Honest opinion as the data of the AI era 27:50 – The co-founder breakup and fears that aren't real 30:06 – Where to find Chomp LINKS Connect with Kiko Zang chomp.fyi • LinkedIn • X/Twitter Download Chomp Redeem the Founder Mode listener offer Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Sep 10

The Accountant vs. QuickBooks Test with Mohammad Moahid

EPISODE 73 Mohammad Moahid has operated multiple companies across e-commerce, consumer electronics distribution, and real estate, and competed for Team Canada as an equestrian. He argues the gap between companies talking about AI and companies actually running on it comes down to ops, not technology. In this episode he explains why leaders are structurally cut off from on-ground reality, why a 5,000-person firm is still managing a hundred active projects out of email threads while million-dollar invoices get written by hand, and where the MIT Nanda study's 95% failure rate really comes from (hint: it's the people layer, not the software). He walks through the "chief agent officer" model, an AI chief of staff coordinating specialist agents across zoning, leasing, acquisitions, and legal. He covers the four pillars he uses to diagnose any business, and the pricing thesis behind what his team calls outcome as a service: you don't pay an accountant for software, you pay so you never think about your books again. Plus what happens to agencies and professional services firms when outcomes get cheaper, and the one thing Mo says humans have to keep owning completely. CHAPTERS 00:35 – AI as the operating system, not another tool 04:37 – What competing for Team Canada taught Mo about execution 05:23 – Why leaders are always removed from on-ground reality 07:26 – Million-dollar invoices, still written by hand 08:33 – Being his own first customer 09:49 – Why 95% of AI implementations fail 10:45 – The command brief and the four pillars 12:49 – The chief agent officer and the 80/20 rule 14:57 – Outcome as a service: accountant vs. QuickBooks 19:05 – Employee fear, and why agencies should be worried 21:17 – What humans still have to own completely 22:41 – Building your own harness LINKS Connect with Mohammad Moahid zerotoagent.com • LinkedIn • Instagram Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Sep 3

13 Agents Watching 76 Agents

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
Aug 27

SaaS Made Her Love Services with Jess Chan

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
Aug 20

The Internet Isn't Dead

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 Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter 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 Stay Connected with Founder Mode Subscribe to our newsletter Connect with Kevin LinkedIn • X/Twitter Connect with Jason LinkedIn • X/Twitter
Aug 13

Think Week is Now Build Week

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

5

out of 5

4 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

76
Rating

Explicit
Copyright

© Kevin Henrikson and Jason Shafton
Show Website

Founder Mode