Founder Mode

Kevin Henrikson and Jason Shafton
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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.

  1. vor 5 Tagen

    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

    13 Agents Watching 76 Agents

  2. 27. Aug.

    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

    SaaS Made Her Love Services with Jess Chan

  3. 20. Aug.

    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

    The Internet Isn't Dead

  4. 13. Aug.

    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

    Think Week is Now Build Week

  5. 6. Aug.

    The Profit Whale with Jason Cohen

    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

    The Profit Whale with Jason Cohen

  6. 30. Juli

    Stop Chasing Plan A with Anthony Ng Monica

    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

    Stop Chasing Plan A with Anthony Ng Monica

  7. 23. Juli

    You Are The Bottleneck

    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

    You Are The Bottleneck

  8. 16. Juli

    Default Alive Without VC Money

    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

    Default Alive Without VC Money
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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.

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  • Erstellt von
    Kevin Henrikson and Jason Shafton
  • Jahre aktiv
    2025 - 2026
  • Folgen
    72
  • Bewertung
    Anstößig
  • Copyright
    © Kevin Henrikson and Jason Shafton
  • Sendungswebsite
    Founder Mode

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