Sleep, Listen, Say No

Why AI Loves Reddit Most with Brent Csutoras

EPISODE 57 Brent Csutoras has spent nearly two decades inside Reddit, Digg, and the message-board underbelly of the internet - and he joins Kevin and Jason to explain why the human voice is now the most valuable thing in marketing. Brent breaks down why Reddit shows up everywhere in AI answers, the biggest mistakes brands make when they enter online communities, and how his team flipped Asurion from a toxic, "scam"-labeled brand into one that controls its narrative across every LLM. He shares the TikTok campaign that pulled in 300 death threats in 30 minutes (and still won the room), why owning the small negatives gives you control of the big ones, and why the next 12 months are a Reddit-and-AI land grab on the scale of short domains and links 20 years ago. If your brand is afraid to show up in the rooms where customers are actually talking, this episode is for you. CHAPTERS 00:00 - The next 12 months is the land grab 00:45 - Marketing in a world where attention is harder to earn 04:01 - Welcome Brent: two decades inside the most misunderstood platform 06:39 - The biggest mistake brands make on Reddit 09:18 - How to reverse a toxic community (TikTok and Asurion) 13:15 - Why Reddit shows up everywhere in AI answers 17:40 - Stop selling features, start solving the real problem 21:24 - What every marketer should stop doing immediately 25:10 - The Reddit land grab and the brands sleeping on it 26:18 - The Asurion turnaround: owning the negative 31:02 - How to show up in AI answers beyond Reddit LINKS Connect with Brent Csutoras OGS Media [https://ogsmedia.com] • LinkedIn [https://www.linkedin.com/in/brentcsutoras/] Stay Connected with Founder Mode Subscribe to our newsletter [https://gofoundermode.com/subscribe] Connect with Kevin LinkedIn [https://www.linkedin.com/in/kevinhenrikson/] • X/Twitter [https://twitter.com/KevinHenrikson] Connect with Jason LinkedIn [https://www.linkedin.com/in/jasonshafton/] • X/Twitter [https://twitter.com/jasonshafton]

Hire Attitude, Not Experience with Jose Li

EPISODE 56 Jose Li, founder and CEO of 71lbs, joins Kevin and Jason to break down how he turned a frustration most companies tolerate, opaque and overcharged shipping invoices, into a 14-year-old business that has saved 5,000 customers more than $80 million. After running FedEx's retail and e-commerce practice, Jose left to tackle the two biggest pain points companies face with carriers: saving money and understanding what they're actually paying. He explains the little-known money-back guarantee policy that leaves $2 billion unclaimed every year, how COVID nearly killed the business and forced a pivot into contract negotiations (now 50%+ of revenue), and why trade shows and in-house cold calling still outperform almost everything else. Jose also shares his vision for layering weather and third-party data on top of shipping decisions, the hiring mistakes that taught him perfect FedEx résumés don't translate, and the chip on his shoulder from 800+ investor rejections that still fuels him today. CHAPTERS 00:00 / Cold Open: $2 Billion in Unclaimed Refunds 03:30 / Meet Jose Li, Founder of 71lbs 03:43 / Spotting the Gap: Two Pain Points Nobody Was Solving 07:14 / From an IP Address to a Real Business 08:30 / The Money-Back Guarantee Most Companies Don't Know About 11:50 / How COVID Almost Killed the Business 12:58 / AI, Weather Data, and the Future of Shipping Decisions 15:10 / Getting the First 10 Customers and Building a Sales Machine 23:52 / Why Trade Shows Are Still the Best Channel 26:47 / The Chip on the Shoulder That Keeps Him Going 30:16 / Founder Mode Top 5 Takeaways LINKS Connect with Jose Li 71lbs.com [https://71lbs.com] • LinkedIn [https://www.linkedin.com/in/josemli/] • X/Twitter [https://twitter.com/71lbs] Stay Connected with Founder Mode Stay Connected with Founder Mode Subscribe to our newsletter [https://gofoundermode.com/subscribe] Connect with Kevin LinkedIn [https://www.linkedin.com/in/kevinhenrikson/] • X/Twitter [https://twitter.com/KevinHenrikson] Connect with Jason LinkedIn [https://www.linkedin.com/in/jasonshafton/] • X/Twitter [https://twitter.com/jasonshafton]

Sleep, Listen, Say No

EPISODE 55 Kevin and Jason tackle the three things every founder pretends they have under control: sleep, the first 90 days of taking over a company, and the say-no muscle. Kevin explains why sleep is the ultimate performance enhancing drug, then unpacks his contrarian take on the first 90 days — by week three you better have an opinion or people start writing you off. He walks through his recent takeover of Search Engine Journal, including the five-question email that stack-ranked his team, the day-zero move to close every credit card and reissue them through Mercury with a named human owner, and the surprise that 15-20% of expenses simply never came back. They close on the say-no muscle, the 14-hour flight test for shutting work off, and how AI tools are creating new leverage to delegate the work you'd otherwise feel obligated to do yourself. CHAPTERS 00:00 – Cold open: Sleep is the ultimate PED 00:51 – Welcome and the three topics 01:00 – The founder sleep crisis 03:52 – Topic two: Taking over a new company 04:00 – Why consultants get more leverage than FTEs 07:09 – Getting acquired and the listening tour 09:02 – The week three framework (not day 90) 12:13 – Search Engine Journal takeover and the five-question email 16:03 – Closing every credit card on day zero 20:17 – Topic three: Building the say-no muscle 24:31 – The 14-hour flight test 26:25 – Five key takeaways LINKS Sleep masks Kevin recommends Alaska Bear [https://a.co/d/09PgkPQ8] • WAOW [https://a.co/d/0514QSW1] Stay Connected with Founder Mode Subscribe to our newsletter [https://gofoundermode.com/subscribe] Connect with Kevin LinkedIn [https://www.linkedin.com/in/kevinhenrikson/] • X/Twitter [https://twitter.com/KevinHenrikson] Connect with Jason LinkedIn [https://www.linkedin.com/in/jasonshafton/] • X/Twitter [https://twitter.com/jasonshafton]

Fire Your Worst Customers

EPISODE 54 Kevin and Jason break down why Anthropic is out of compute, why that's actually a strategy, and what it means for everyone using Claude right now. They dig into the Mythos model as the best marketing moment in AI, why artificial scarcity works, and why $200/month for Claude Max is the cheapest hire you'll ever make. Then they shift to AI in the enterprise — why one "AI Week" won't rewire your company, why Anthropic's one-person growth marketing team is the new bar, and the playbook for founders selling into big companies: pick a hard enough wedge, stop selling the product, and sell transformation instead. CHAPTERS 00:00 – Cold Open: The Mythos Model Is Too Good To Release 00:35 – Welcome to Founder Mode 00:59 – Why Anthropic Is Out of Compute 02:28 – Good Customer, Bad Customer: Who's to Blame? 04:00 – $200/Month Is the Cheapest Hire You'll Ever Get 05:31 – Token Maxing and the New Scarcity 07:01 – How to Fire Bad Customers (And Why Anthropic Is Doing It Wrong) 10:50 – The Mythos Model: The Best Marketing Moment in AI 13:19 – AI in the Enterprise: Why One AI Week Isn't Enough 18:25 – The "One More Prompt" Flow State 19:57 – Selling Into Enterprise: Pick a Hard Wedge, Sell Transformation 22:48 – Closing Takeaways and Top Five LINKS Stay Connected with Founder Mode Subscribe to our newsletter [https://gofoundermode.com/subscribe] Connect with Kevin LinkedIn [https://www.linkedin.com/in/kevinhenrikson/] • X/Twitter [https://twitter.com/KevinHenrikson] Connect with Jason LinkedIn [https://www.linkedin.com/in/jasonshafton/] • X/Twitter [https://twitter.com/jasonshafton]

AI as a Financial Co-Pilot with Shain Noor

EPISODE 53 In this episode, Kevin and Jason sit down with Shain Noor, co-founder of Silvia, an AI-powered personal CFO built to help people reason through financial decisions, not just track them. Shain explains why the entire history of personal finance apps has focused on clicking and aggregating data rather than helping users actually decide what to do, and how Silvia uses Anthropic-powered agents with a verification layer to deliver trustworthy, personalized financial guidance. The conversation covers the co-pilot vs. autopilot distinction, the surprising discovery that users ask Silvia things they'd never tell their human financial advisor, how proactive alerts like the daily summary email drove retention, and why building the reasoning layer first, before adding any execution or action capabilities, is the right foundation for trust. CHAPTERS 00:00 - The judgment-free financial advisor 02:38 - Introducing Shain Noor and Silvia 03:51 - Why finance apps have always missed the reasoning layer 05:51 - Co-pilot vs. autopilot: trust, transparency, and guardrails 08:29 - What surprised Shain: users sharing what they hide from their advisors 12:42 - Measuring retention and the proactive alerts breakthrough 17:02 - Team size, the ProCap merger, and competing with legacy finance 19:41 - The future: everyone becomes a manager of AI agents LINKS Connect with Shain Noor Silvia [https://cfosilvia.com] • LinkedIn [https://www.linkedin.com/in/shainnoor/] • X/Twitter [https://twitter.com/ShainCodes] Stay Connected with Founder Mode Subscribe to our newsletter [https://gofoundermode.com/subscribe] Connect with Kevin LinkedIn [https://www.linkedin.com/in/kevinhenrikson/] • X/Twitter [https://twitter.com/KevinHenrikson] Connect with Jason LinkedIn [https://www.linkedin.com/in/jasonshafton/] • X/Twitter [https://twitter.com/jasonshafton]