AI for Founders with Ryan Estes

Episodios

• 800,000 Lives, 210 Engineers, One Bet: Inside Collective Health's AI Push 25.06.2026 53m

  The same artificial intelligence saved one insurer a billion dollars and cost another two billion. Same tool. Opposite outcomes. The only variable was who the machine was actually working for.That single tension is where this episode opens, and it turns out to be the question that quietly decides everything a founder builds. Gaurav Agrawal, Vice President of Engineering at Collective Health, has spent a career standing at the exact moment technology flips from impossible to inevitable. He was in the Apple atrium when Steve Jobs revealed the iPhone and watched the room's jaws hit the floor. He helped Reliance Jio connect 18,000 villages and vault India from 150th in the world for broadband penetration to first in a matter of months. Now he is pointing that same instinct at the most broken machine in America: healthcare.What makes this conversation land is that Gaurav refuses the easy framing. AI is not good or evil in healthcare, he argues. It is a mirror. Point it at margin and you get claim denials at machine speed. Point it at the member and you get a 24/7 companion that answers "why was my claim denied" in plain language, a copilot whispering the right answer into a service agent's ear so they can drop the robotic script and actually be human, and a roadmap that arrives in months instead of years. At Collective Health, the rule is blunt: every AI decision starts from "how does the customer benefit." If it also saves money, that is icing on the cake, never the recipe.The episode gets personal, and that is where it earns its rating. Gaurav's mother fell ill after moving to the US. The best healthcare system in the world, the one he trusted, failed her. He flew her back to India for care. She is no longer with us. That loss is the engine behind his work, and you can hear it. For founders, the practical payload is just as sharp: the benefits trap that springs the moment you hire your tenth person, the places AI absolutely should not go (claim rejections still pass through human eyes, every time), and how a lean team of around 210 engineers compresses an 18-to-24-month roadmap into six.https://collectivehealth.comhttps://aiforfounders.cohttps://inboxalchemy.co
• What It Do: First-Time Founders Build Product. He Built a Distribution Robot. 25.06.2026 30m

  Two founders sit down on a Friday with the World Cup playing in the background, and within ten minutes one of them casually reveals he has built a version of himself that works while he sleeps.That is the hook, and it is not hype. Jason Katz, co-founder of Kindling Solutions, walks through what he calls his personal content machine: a chain of Notion databases, AI agents, and approval triggers that takes a single spoken idea and turns it into finished video, social posts, and carousels, all before he sits down at a computer. The genius is not the automation. Plenty of people automate. The genius is that the output sounds exactly like Jason, because the system is engineered around authenticity instead of around shortcuts.Here is the part that should make every founder lean in. Jason does not let the AI write his ideas. He lets the AI interview him. He talks into his phone in the backyard with a coffee, an interviewer agent trained on the tactics of Joe Rogan, Oprah Winfrey, and Howard Stern pulls his real takes out of him across ten to twelve questions, and only then does the structuring begin. The words are his. The machine just gives them shape. As he puts it, the context truly does half the work, and that is the line nobody is saying out loud.Meanwhile Ryan turns the conversation into a masterclass on performance itself. After more than a thousand podcasts, he has reduced great content to a few unglamorous truths: sleep and caffeine are the real production stack, clarity beats cleverness, lead with a current event so your guest can find their feet, and tell yourself to speak ten percent slower so the ums take care of themselves. It is the kind of advice that sounds obvious until you realize almost nobody actually does it.Both threads land on the same destination. First-time founders obsess over product. Second-time founders obsess over distribution. Jason and Ryan are both, by their own admission, finally crossing that line, moving from "what is this business" to "let the world know what is up." The episode is the sound of two operators getting comfortable being the face of the thing they built.⁠⁠https://kindlingsolutions.com⁠⁠https://aiforfounders.co⁠⁠https://linkedin.com/in/jasonkatz99/⁠⁠https://linkedin.com/in/estesryan/⁠⁠
• AI Heart Doctor (And 150 Fortune 500s Are Buying) 22.06.2026 54m

  Your blood pressure spikes the moment the cuff goes on. You are sitting on crinkly paper in a cold room, and the number on the screen has almost nothing to do with the life you actually live. This is the white coat problem, and it is a tidy little metaphor for everything broken about reactive healthcare: we measure people at the exact wrong moment, in the exact wrong place, and then we wonder why outcomes lag.Amir from Hello Heart spends his days inside that gap. Hello Heart is a preventive heart health platform built around a connected blood pressure monitor, a smart pill box, and a mobile app, and it is trusted by more than 150 Fortune 500 and government employers. The newest piece is Nia, which the company launched in October 2025 as the world's first AI heart health assistant. This episode is the rare founder conversation that hands you the blueprint instead of the brochure. If you are building vertical AI, health tech, or any agent where a wrong answer carries real consequences, this is the one to study.The throughline is trust. Amir keeps returning to a simple idea: humans were never meant to be the data layer. The job of AI here is not to replace the doctor. It is to absorb the 90% of a visit that is administrative friction so the 2% that is actually human, the fear, the reassurance, the "how does this fit your life," can finally breathe. He calls it the shift from reactive to preventive, and he is blunt that the only way to earn it is to build guardrails most teams skip.https://www.helloheart.comhttps://www.linkedin.com/in/amir-dolev-b5618421/https://www.helloheart.com/press/hello-heart-launches-the-worlds-first-ai-heart-health-assistant-niahttps://ainativestudent.com⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠https://inboxalchemy.co/
• The Self-Driving Car Of Men's Fashion 19.06.2026 43m

  A stranger gives you ten seconds. Before you open your mouth, before the pitch, before the handshake, they have already read your shirt and filed you away. Zoher Karu thinks that ten seconds is a data problem, and he left one of the biggest data jobs in tech to go solve it.Zoher spent years as Global Chief Data Officer at eBay and Chief Data and Analytics Officer at Blue Shield of California. Now he is Head of AI at Taelor, the AI-powered menswear rental subscription founded by Anya Cheng and Phoebe Tan. The premise is simple and a little radical: most men do not have the time, the skills, or the desire to shop, yet they still want the outcome of looking sharp. So Taelor sends you a box, you wear it, you keep what hits, you mail back the rest, and no one ever folds laundry or guesses at the mall again.Underneath the box is the hard part. Zoher calls it the matching problem. Picture Ryan, 30,000 pieces of inventory, and the question "which six go in the box." Basic rules thin the herd, no wrong sizes, no shirts you would hate. After that, you need to capture something almost nobody can write down: why a person on the street simply looks put together. Ask a great stylist to explain the rule and they cannot, the same way a driver cannot list every reason they tap the brake. Taelor's job is to bottle that instinct and run it at scale, with human stylists in the loop and the machine learning from every piece of feedback.The twist that should make founders sit up is the second business hiding inside the first. Every rental generates a signal about what real men actually like on real bodies in real contexts. Brands today buy on gut, betting that yellow is big this year. Taelor is building the feedback layer that turns a B2C rental into a B2B data product for the brands themselves, with sustainability as the upside, since roughly 30% of clothing reportedly reaches the landfill never having been worn.This one is for the founder who spent on the camera and the mic and still shows up in a college shirt. Your product may be great. In the first ten seconds, you are the product.https://taelor.style/https://taelor.style/pages/membershiphttps://www.linkedin.com/in/zzkaru/⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠https://inboxalchemy.co/ https://ainativestudent.com/
• 40,000 Models, One API Key, And A $25M Bet On Open Source 18.06.2026 1h 2m

  Every month your inference bill climbs, and you tell yourself it is the cost of doing business. What if it is actually a tax on what you do not know? In this episode, the founder of Featherless makes a blunt case: the best model for most of what your startup does is open source, often runs for basically peanuts, and is frequently built in China. He has put real money behind that thesis, about $25M across a seed and a Series A led by AMD Ventures and Airbus Ventures, and a platform that holds tens of thousands of open models online at once through a single API key.The throughline is freedom. Eugene's grandmother speaks seven languages and none of them are English or Chinese, which is roughly half the planet that the closed, English-and-Chinese-first future would leave behind. Open source, he argues, is not just free as in money. It is free as in freedom: when the model runs on your terms, nobody can ever take it away from you. He walks through why the database wars of the past, Oracle and Microsoft and IBM, then MySQL and Postgres, are replaying in AI at ten times the speed, why "lazy" models are really just a mirror of us, and why the labs chasing superintelligence may be solving the wrong problem while businesses quietly beg for one thing: reliability.⁠⁠https://www.featherless.ai⁠⁠https://www.x.com/picocreator (Eugene on X)⁠⁠https://www.techtalkcto.substack.com (his Substack, Tech Talk CTO)⁠⁠https://www.wiki.rwkv.com (RWKV, Linux Foundation)⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠https://inboxalchemy.co/ https://ainativestudent.com/
• He Analyzed Millions of Calls. The Move That Closed Deals Was a Laugh. 17.06.2026 54m

  There is thirty billion dollars a year in lost rent sitting in empty units across America, and that vacancy quietly erases roughly half a trillion dollars of property value. Everyone assumed the fix was price, amenities, or a slicker chatbot. Then Nick Deveau and his co-founder Ben Epstein got their hands on millions of real leasing calls from one of the largest apartment owners in the country, pointed a team of machine learning engineers at the data, and found something nobody scripted for. The single strongest predictor of a signed lease was not the special, not the square footage, not a scarcity tactic. It was whether the leasing agent laughed on the phone. The second strongest was whether they asked a genuinely curious question.So Grotto AI did the counterintuitive thing. While most of the industry raced to replace humans with voice agents, Grotto built a tool to make humans better at the one thing only humans can do: build rapport. A leasing agent gets a push notification fifteen minutes before a tour telling them the prospect has a dog named Fido, loves natural light, and drives a Subaru. They record the tour on a small clip-on mic, get instant feedback on what they crushed and what they missed, and Grotto drafts the personalized follow-up, catches the special they forgot to mention, and quietly does the CRM grunt work. Nick calls it targeted advertising for the real world. Ryan called it a second brain for the field. Both are right.This episode is the clearest case study going for vertical AI: pick one painful, measurable leak, capture data nobody else has, and sell revenue instead of cost cuts.https://grotto.aihttps://www.linkedin.com/in/nick-deveau-a6241379/https://www.linkedin.com/in/estesryan/https://aiforfounders.cohttps://inboxalchemy.cohttps://robinhood.org
• AI Law Firm: The Logan Brown Playbook 16.06.2026 56m

  Time kills deals. So does the fine print you never read.James Charles sold the fastest-moving makeup palette in history, did a reported $100 million in revenue, and reportedly walked with around $2 million, because somewhere in a contract he did not read, the math got decided for him. That is the horror story Logan Brown tells founders to wake them up. Then she hands them the antidote.Logan walked into the Douglas County District Attorney's office in Lawrence, Kansas at twelve years old and asked for a job. A secretary named Dolores made her a personal intern, and Logan spent her summers filing, dusting, and sitting in on hearings she had no business sitting in on. Vanderbilt valedictorian. Harvard Law. A machine-washable pantsuit company called Spencer Jane that she still runs out of her parents' basement. Two and a half years at Cooley billing $900 an hour to the founders she could not stop admiring. And then, when she watched ChatGPT and Claude crack open legal work, she did the unthinkable: she left to build the thing that competes with the very rates she used to charge.Soxton is an AI-powered outside general counsel for early-stage companies. You make a request on the site in plain English, AI takes the first pass, a startup lawyer with real experience reviews every single output, and you get your document back in 24 hours for $100. Form a Delaware C Corp for free through a banking partner. Get your influencer or advisor agreement papered for a hundred bucks. Run a priced round for $10,000 instead of the $50,000 to $100,000 Big Law charges. Logan is blunt about who she is fighting: her competition is not Cooley, it is Claude and ChatGPT, and her edge is the human in the loop plus the market data from thousands of deals that tells you when a provision is one you should never sign.This one is for the founder who keeps saying "I'll deal with legal later." Later just got a lot cheaper.https://www.soxton.ai/https://x.com/loganbrown799https://www.linkedin.com/in/logan-brown-03765552⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠https://inboxalchemy.co/ https://ainativestudent.com/
• America Spends $5 Trillion On Health. This Is Where It Leaks. 13.06.2026 57m

  The real villain in American healthcare is not the insurance company. It is the hold music.The United States burns an estimated $350 billion a year on administrative waste, $266 billion of it from sheer complexity and $84 billion from fraud and abuse, and that sits inside a healthcare economy so large that if you sliced it off on its own it would rank as roughly the fourth biggest economy on earth. Patients lose their patience before they ever lose their health, and the industry has spent years selling a false binary: hire more humans who burn out, or unleash bots that collapse the moment a call actually matters.Frederik Mueller, Timm Schneider, and their team built Third Way Health on a different premise. Pair AI agents with embedded human operators, let the machines crush the repetitive volume, and free real people for the conversations that need a heartbeat. The company started before ChatGPT made AI a dinner-table word, which is why the name carries a double meaning: there was always a third way between low-tech service vendors and high-friction software, and there is now a third way between full automation and full staffing. Jamie Reddick, COO of Graybill Medical Group, lived the payoff. Over a two-year partnership, North San Diego County's largest independent multi-specialty group cut front-office costs by roughly $3 million, about 50%, while making patients feel less like a ticket number and more like a person.This episode is a clinic on building in a broken market without pretending the brokenness will disappear if you throw enough technology at it.https://thirdway.healthhttps://www.linkedin.com/in/frederik-mueller-53198a17/https://www.linkedin.com/in/timm-schneider-463a2683/https://www.linkedin.com/in/jamie-reddick-586691249/https://podcasts.apple.com/us/podcast/healthcare-ops-wave/id1774334723https://aiforfounders.cohttps://inboxalchemy.cohttps://ainativestudent.comhttps://www.linkedin.com/in/estesryan/
• "We're AI-First!" No You're Not. Here's the Test. 12.06.2026 55m

  A CEO told Justin Watt his company was ready for AI. "We've got our data architecture together," he said, giddy. Justin asked to see it. The guy pulled up an Excel file. The filename? Data Lake.That moment is the whole episode in miniature. Justin Watt, co-founder of Switchboard, studied psychology, not computer science, and that turns out to be his unfair advantage. After stints at IBM and MetaLab (where his teams built products for Uber and Amazon and helped design Slack), Justin realized the hardest part of every technology project is never the technology. It's the humans. Every business challenge is a human challenge wearing a software costume.Switchboard works with mid-market companies, the $50 million to $500 million crowd, the businesses old enough to have 40 years of legacy process and young enough to actually change. These companies think they're AI-enabled because they bought everyone a Claude license. Meanwhile, month-end close runs through one person's spreadsheet that nobody else can read, and if that person quits, the business forgets how it works.Justin's fix is unglamorous and devastatingly effective: map the real workflow, not the org-chart version. Find where humans are doing machine work. Inject AI at the steps where it actually moves the needle. Keep humans in the loop everywhere else. The result isn't layoffs, it's smart people finally doing smart work. In Justin's experience, less than 5% of leadership conversations are about cutting headcount. The conversation is always about the endless pile of work standing between the company and its goals.Along the way, Ryan and Justin cover the AI washing epidemic (blaming layoffs on AI to cover up old hiring mistakes), why frontier lab doom marketing blew up in everyone's faces, the death of "bring your whole self to work," quiet quitting as cowardice, Garth Brooks selling his catalog for a rumored $2 billion, ravens that speak English, and the most surreal government website in existence.https://withswitchboard.comhttps://www.linkedin.com/in/wattjustin/https://aiforfounders.cohttps://inboxalchemy.cohttps://spcai.orghttps://www.war.gov/ufo (referenced as war.gov/ufo)https://suno.com (Suno, the AI music generator discussed)
• Agent Memory Is the Next Great Moat 12.06.2026 47m

  What if the dumbest thing your startup does this year is hire?In Zurich, a six-person company is serving Fortune 500 clients with a rule that sounds like heresy: no human in the company can be assigned a task. The software literally locks them out. Every task goes to an agent first, and the agent decides when a human's judgment is actually worth the interruption.That company is Salfati Group, and its founder is Elon Salfati. Yes, Elon. No, not that one. This Elon is a former Israeli intelligence engineer, ex R&D Director at web security firm Reblaze, co-founder of RELE.AI, founder of intelligent testing startup Metiss, and now a PhD researcher in AI security. He has spent his career deleting more code than he writes, and now he is deleting org charts.The episode opens with a ripped-from-the-headlines jump off: Microsoft's Build 2026 announcement of Autopilots, always-on agents with their own identity that act on your behalf. Ryan asks the uncomfortable question: if 10,000 enterprises flip on the same agents, does diversity of thought dissolve into a hive mind? Elon's answer reframes the whole AI transformation conversation. Most companies are stuck sprinkling AI to please the board or deploying point solutions on annoying spreadsheets. The real unlock is flipping the entire model from "a human with an army of agents" to "an army of agents with a human."From there the conversation gets practical, then philosophical, then back again. Elon walks through a real client engagement: a service marketplace with a 51-step quote-to-cash process bleeding retention, and how color coding every step revealed exactly where humans add value and where they were just hands on keyboard. Then Ryan, a lifelong meditator and self-described student of human consciousness, pulls Elon into the deep end: what does it mean that Salfati Group calls its agents sentient? Elon's answer centers on memory, causality, and temporal understanding, and why he believes agent memory is the next great moat. Plants, cats, the Library of Alexandria, and Mr. Bridgewater the Denver farrier all make appearances. It is that kind of episode.salfati.groupaiforfounders.coinboxalchemy.coElon Salfati on LinkedIn: linkedin.com/in/elonsalfatiRyan Estes on LinkedIn: linkedin.com/in/estesryan
• What it do!? The Jujitsu Secret That Scales Companies Without Force 08.06.2026 38m

  Two purple belts walk back onto the mat after years away, and the guy who is slow, mindful, and refuses to break a sweat starts sweeping and submitting the meatheads who are gassing out around him. That is not a jujitsu story. That is the whole episode.This week Ryan Estes and Jason Katz, co-founder of Kindling Solutions, skip the warmup and go straight into the thing every founder feels but rarely says out loud: the ground is moving under all of us, the tools are getting absurdly good, and the people winning are not the fastest or the strongest. They are the ones with stillness, leverage, and an authentic voice that no model can fake.Jason walks through the operating system he is quietly building around himself. A morning brief that reads his Slack, his Teams, yesterday's calls, today's calendar, and his open tasks, then hands him a five-line executive summary before he has even left the porch. A content pipeline that researches ideas, scores them, then interviews him in his own voice like Joe Rogan would, so the output is actually him and not another pile of generated mush. Then the conversation turns to the uncomfortable truth he calls his thorn: everyone is an AI consultant now, the way everyone in Colorado had a grow in 2009, and the single-workflow microservices people are productizing today will cost three dollars on a phone very soon. The question is not whether you can automate something. The question is where your margin lives once the press-a-button version arrives.Ryan counters with the optimist's case. The bigger the frontier models get, the wider the gap between AI-native founders and everyone else, and the more demand there is for people who can actually integrate this stuff with taste. His own proof: web traffic, newsletters, and podcasting, the three compounding channels he believes are the only distribution worth grinding for, because you own them and no single algorithm can switch them off overnight.It is fast, funny, and genuinely useful, with a side of hair powder and an au pair from South Africa. Pull up a chair.https://kindlingsolutions.com (relaunching, was not live at recording)https://www.linkedin.com/in/jasonkatz99/https://www.headset.iohttps://www.anthropic.comhttps://search.google.com/search-consolehttps://www.eastonbjj.comhttps://trynina.cohttps://aiforfounders.cohttps://inboxalchemy.cohttps://www.linkedin.com/in/estesryan/https://trynina.cohttps://ainativestudent.com
• The $18 Billion Backdoor: How One Aussie Founder Plans to Eat LinkedIn Alive 08.06.2026 58m

  The inbox is dead, and the people who keep emailing it the hardest are the ones killing it fastest.David Connors has watched this happen up close. He sold his recruiting automation startup, Automately, to Sequoia Capital, spent two years inside the firm building tools so its investors and founders could answer one maddening question, "who do we actually know at company X," and walked out with a conviction that turned into a company. That company is The Swarm, the relationship intelligence platform he now runs as Co-Founder and CEO, and this is his second time on the show. In the twelve months since his last visit, the world sped up, the spam cannons got louder, and David got quieter, more grounded, and 35 pounds lighter. The throughline of this episode is simple and a little uncomfortable: AI made it trivially easy to write the perfect cold message, which means the perfect cold message is now worth almost nothing. What it cannot fake is trust. And trust, David argues, is the only currency left.The conversation moves from the personal to the tactical and back again. David opens up about how he protects his attention as a father of two with a third on the way, why he treats work like a sprinter treats a race rather than a marathoner who never stops, and why running yourself into the ground produces expensive decisions you pay for twice. Then Ryan steers into the meat: how The Swarm passively maps the network sitting around your entire company, not just your personal Rolodex, and turns it into a third sales channel that is neither inbound nor outbound. The numbers do the talking. A warm intro converts ten to twenty times better than cold. Google and Microsoft are now filtering out senders you do not recognize. The motion that used to eat ten to 15 hours a week of someone's time now takes ten minutes with agents. And the whole thing compounds, because every customer you close maps a new network you can map next.There is a bigger swing underneath all of it. David is not trying to be a $10 million enrichment-data business. He wants to carve into LinkedIn's roughly $18 billion revenue run rate by building the relationship graph that agents can actually use, the thing LinkedIn built for the SaaS era but will never open up. Whether you buy the vision or not, the practical takeaway lands either way: map your network, treat it like an asset, batch your asks, close the loop, and never become the neighbor who only knocks when they need an egg.https://www.theswarm.comhttps://www.linkedin.com/in/connorsdavid/⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠https://inboxalchemy.co/ https://trynina.co/ https://ainativestudent.com/https://www.ymcasf.org
• Stop Getting Paid for Hours. Start Getting Paid for Outcomes. 06.06.2026 51m

  She didn't get maternity leave. So she rewired the entire way she worked, and accidentally redrew the map of what her career was worth. In 2020, Ashley Gross was just another marketer pulling 80 hours inside a 40-hour job, operating on the oldest visibility hack in the book: be the first one in, be the last one out. Then she became a mom with no leave on the table, and the math stopped working. So she started teaching AI to do her busywork, not to impress anyone, but to claw back time with her newborn.What happened next is the real story. The automation didn't free her. It exposed her. All the work she clawed back came flooding right back in, because she was the comfort person, the human Google, the one who knew where every document lived. Knowledgeable, indispensable, and quietly underpaid. That gap, between the work you do and the work people can see, became her whole thesis.She walked into the CMO's office, handed over her playbook, and built her own unpaid internal AI champion role to test one question: does this knowledge transfer to other humans? Within three months, the answer was a $25 million pipeline overachievement. That was the moment the imposter syndrome died. Then came the newsletter, zero to over 5,000 in two months of cringey, daily, ego-at-the-door posting. Then a Maven waitlist of more than a thousand people telling her they would pay. Only then did she jump, never risking the paycheck that fed her family until the runway was already built.Today AI Workforce Alliance runs on a team of twelve full-timers, ten-plus part-timers, freelancers, and a few agents quietly handling the admin in between. Notion is the centralized brain. Claude and MCP connectors do the talking. The tech stack went from sprawling to five tools. The plan for 2026 is to 10X through partnerships. And she still hates social media, which is exactly why you should trust her when she says you have to do it anyway.https://aiworkforcealliance.comhttps://www.linkedin.com/in/theashleygrossThe AI Work Week (Wiley), pre-order on Amazon and https://www.barnesandnoble.comhttps://tgpdenver.org (The Gathering Place, Denver)⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠https://inboxalchemy.co/ https://trynina.co/ https://ainativestudent.com/
• 35x More Profitable Than Marketing | JP Grace from Endear 04.06.2026 50m

  The salesperson of the future never forgets you. The only question is whether that feels like care or surveillance.JP Grace has worked the floor. Publix bag boy, Breckenridge coffee shop, the whole tour. Now he's the CTO of Endear, the retail-first CRM powering one-on-one selling for brands like Reformation, Untuckit, Jones Road Beauty, AG Jeans, and Boll & Branch across more than 2,000 stores in 19 countries. And he's on a mission to give brick-and-mortar sales associates what B2B reps have had for decades: a system that actually remembers the customer.Here's the problem Endear attacks. A sales associate gets maybe fifteen minutes at the start of a shift to message VIPs. Finding the right person, drafting the right note, picking the right template: it's all friction. So most outreach never happens, and the customer who walked away from out-of-stock shoes last Tuesday just disappears forever. Endear's brand-new AI Opportunity Engine, launched the day after this recording, flips that. It surfaces the five to ten biggest opportunities for each associate every morning, pre-drafts the message, and lets them review and send in seconds. Early results: 6x more outreach in six weeks and a 35x return on delivered messages.JP's career arc is its own masterclass. He helped take LiveIntent from zero revenue to a valuation in the hundreds of millions, coached startup CTOs at AB InBev's ZX Ventures, and joined founders Leigh Sevin and Jinesh Shah after they'd spent years pivoting in stealth before catching their inflection point in March 2020, when the world went inside and brands scrambled for ways to keep selling without foot traffic.Meanwhile, Ryan relives his entire retail past, from selling 30 electronic drum kits to Colorado Springs mega churches at Guitar Center, to leading the nation in Finding Nemo pre-sales, to a return-counter horror story at Nordstrom you will not forget. Underneath the laughs is a serious thesis: the companies that win the next decade won't have the best products. They'll be the ones who remember you the warmest.https://endearhq.com/https://www.linkedin.com/in/josephpgrace/⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠https://inboxalchemy.co/ https://trynina.co/ https://ainativestudent.com/
• "Intensity Is a Bulldozer" The Leadership Trait Everyone Praises and Nobody Survives 02.06.2026 50m

  The wall you built to protect yourself is the same wall your team can't get past.Most founder advice is about adding. Add a growth loop. Add a framework. Add another seven habits. Tyler Dickerhoof showed up to AI for Founders to argue the opposite. The thing standing between you and the company you want is usually something you are spending enormous energy to keep hidden.Tyler is the founder of the Impact Driven Leader community, host of The Tyler Dickerhoof Show, a Cornell graduate, and the author of a new book called The Things We Hide. He has generated more than $700 million in business sales across a career that started, of all places, as a nutritionist for dairy cows in Ohio. He is not a guru who floated in from a TED stage. He is a farm kid who got told farm kids were not smart, spent decades proving his worth through intelligence and intensity, and watched that same intensity push away the people he cared about most.The conversation opens with a story he did not tell anyone for years. At 14, in a farming accident, Tyler drove over his three year old brother, who died. Sitting on the hood of a sheriff's car being questioned, a teenage Tyler hardened into a posture that would quietly run his leadership for the next 25 years. Get in line or get out. It took a normal employee dispute at a gym he owned, almost three decades later, to snap him back to that moment and realize, "Oh. That's how I deal with things."From there the episode becomes a working manual for founders on how fears and insecurities leak into leadership, tone, relationships, and revenue, and what to do about it. Tyler and Ryan trade their own defense mechanisms, intensity and anger and humor, and land on a hard truth every operator needs. The scariest part about leading with intensity is not that it fails. It is that it works, in the short term, which is exactly why founders double down on it until the carnage piles up.https://www.tylerdickerhoof.com/book⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠/https://inboxalchemy.co/ https://trynina.co/
• What It Do: 6 Parameters That Separate Cinematic AI From Total Slop 01.06.2026 34m

  Everyone thinks the magic is in the prompt. It is not. The magic is in everything you build around the prompt.That is the thread running through this build in public session, where the conversation goes deep on what it actually takes to make AI video that looks like a real person, sounds like a real person, and does not collapse into that plastic, uncanny mush we have all learned to scroll past. The answer is not a better sentence typed into a box. It is a system. A founder who spent nine months in trial and error walks through the exact chain of models, references, and approvals that turns a single orange hoodie character into a living, transforming short film. Along the way you get the unglamorous truths nobody puts in a launch video: the order you stitch voice and visuals in matters, your characters have to be locked before they are useful, and the cheapest thing in the entire pipeline is the thing that holds it all together.There is also a quieter story underneath the tooling. It is about why a founder builds anything as a system in the first place, the pull between shipping at scale and being present in your own life, and the strange new normal where your face and your voice can be reproduced from a phone full of selfies.https://www.linkedin.com/in/jasonkatz99/⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠https://inboxalchemy.co/ https://trynina.co/
• Ship A Full App In 5 Minutes, Not 5 Weekends 31.05.2026 57m

  Every founder has a graveyard. Half-finished apps, abandoned prototypes, that "killer tool" you vibe-coded over a weekend and never touched again. Mariam Hakobyan, Co-Founder and CEO of Softr, thinks she knows exactly why those projects keep dying, and it is not your discipline. It is the chains. AI handed everyone a hammer and called them a carpenter, but it never removed the hard part. It just moved the complexity onto you: the authentication, the permissions, the security, the thousand boring edge cases that make a toy into a tool people can actually log into.Mariam is an engineer turned entrepreneur who led product and engineering teams of forty-plus people before walking away from a six-figure job to build something of her own. She and her husband Artur Mkrtchyan started Softr in 2019 with one stubborn belief: 80% of every business app is the same repetitive plumbing, and nobody should have to rebuild it from scratch ever again. They call it Lego for software. Connect your data, snap the blocks together, and a non-technical operator ships a full, secure, working app in about five minutes.The numbers tell a quiet, brutal story. A $2.2M seed they did not even plan to raise. A $13.5M Series A from FirstMark. Then a hard stop on fundraising, because the thing was already profitable. Today Softr runs eight-figure revenue with a lean team of fifty across fifteen countries, no traditional sales team, and growth that came almost entirely from a Product Hunt launch and word of mouth. Oh, and investors told a husband-and-wife founding team it would never work. Mariam's reply: they had a decade of conflict-resolution experience before they ever incorporated.This episode is for the founder who keeps starting and never shipping, the operator drowning in spreadsheets, and anyone trying to figure out when to reach for Claude Code and when to put the terminal down.https://www.softr.io/pricinghttps://www.linkedin.com/in/mariamhakobyan/⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠ https://trynina.co/
• "We Don't Use AI" Will Be the Flex of 2026 30.05.2026 59m

  Two fifteen-year-old rock climbing buddies from Long Island made a pact in a surf lineup: build one-of-a-kind experiences for causes they cared about. That idea died. So did the loyalty app before it, and the apparel company after it. What survived was the thing nobody planned, an agency born from following opportunity instead of forcing a vision.Justin Abrams and Mike Rispoli have been failing forward together for twenty years, and Cause of a Kind is the compounding result. The deal that let them quit their jobs was the Hospital for Special Surgery in New York, their first real foray into medical software and the moment Justin took out a half million dollar SBA loan and burned the boats. Today they build and modernize software for small and mid-sized businesses on a flat monthly model, no offshore handoffs, no surprise invoices.This conversation is a gut check for every founder currently drowning in shiny object syndrome. Mike has the scars of the Web3 era and sees the exact same pattern repeating with AI: companies slapping an "AI native" label on a context call to ChatGPT, then wondering why three competitors clone them in a month. His thesis is sharp and survivable. The magic is not AI. The magic is AI plus workflow plus deep domain knowledge, the combination that cannot be knocked off because you had to be the person on the inside to build it.Then there is the distribution story, which is the part founders will rewatch. Cause of a Kind went from roughly 7,000 to 160,000 plus YouTube subscribers in five months by doing one unglamorous thing relentlessly: they ship every single day. No filter, no precious production cycle, just two fast-talking Long Islanders who treat their business as a media house and treat publishing as the cheapest sales conversation on earth.https://www.causeofakind.com/https://www.linkedin.com/in/cuzzinjustin/https://www.linkedin.com/in/michael-rispoli-cto/https://www.youtube.com/channel/UCWAstEyCK6YsKVTTRsQr37w⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠https://trynina.co/
• The Physicist Building a Compiler for the Real World | Hugo Nordell, Encube 29.05.2026 1h 3m

  Some of the smartest engineers alive are designing the physical world with software older than their interns. Brake discs, axles, medical devices, aircraft, all built on tools that can take twenty minutes just to open a file, and a knowledge base that walked out the door when the industry shipped its expertise overseas. Hugo Nordell saw this up close. Trained as a theoretical physicist, seasoned in Silicon Valley's drone and autonomous driving years, then a digital transformation executive at Sandvik and Aker, he kept watching brilliant hardware teams fight their own tooling on a daily basis while production costs quietly ballooned.So he built the thing he wished he had. Encube is a browser based, collaborative design platform that sits between your CAD system and your release management, then layers AI on top of a foundation almost nobody else is building: a deterministic engine that actually understands manufacturability. Think of it as a FigJam board on steroids, where complex CAD models and heavy engineering drawings become first class citizens, loading in two to three seconds on a run of the mill laptop with no expensive graphics card required. People thought he was cheating. He was not.The deeper insight is the one founders in every category should tattoo somewhere visible. Generative AI is rewriting software engineering because software has forty years of validation infrastructure: compilers, linters, unit tests, CI/CD, stack traces that let an agent self correct. Hardware has none of that. There is no compiler for atoms. So Encube is building one, on the GPU, blazingly fast, deterministic where it must be, with large language models bolted on only at the edges where stochastic answers are safe. Get that order right, and you could reimagine hardware design the way Lovable, Bolt, and Claude Code reimagined software. Get it wrong, and you ship slop into the one place slop kills people.https://www.getencube.comhttps://www.linkedin.com/in/hugonordell/⁠⁠https://www.linkedin.com/in/estesryan/⁠⁠⁠⁠https://aiforfounders.co⁠⁠https://trynina.co/
• Why Posting on LinkedIn Is Dead (And What Top Founders Do Instead) 28.05.2026 51m

  That is the dirty secret of LinkedIn for most founders. You scroll, you cringe at the textbook-perfect ChatGPT posts, you maybe drop a like, and you log off feeling exactly as broke as when you opened the app. Ali Hafizji, founder and CEO of Wednesday Solutions and the builder behind Chime at getchime.co, has been quietly running a different playbook. He went from under 5,000 LinkedIn followers to 12,000 without leaning on a content engine. The trick was not posting more. It was commenting smarter, on the right posts, in front of the right tribe, every single day.In this episode, Ali breaks down why the comment section is the most underutilized lever in B2B SaaS, why your ICP does not want to be educated by you, and how he built an AI agent that does the soul-crushing work of finding the right LinkedIn conversations so you can show up, drop one human comment, and close the laptop in ten minutes. He also walks through the design partner pricing, the rare anti-predatory SaaS model where the price goes down as the user base grows, and the curation logic behind Chime's 40,000-influencer database. If you have ever felt invisible on LinkedIn while watching your competitors print pipeline, this one is for you.The Interest Graph Engagement LoopEngage on posts that match your expertise.Show up in the feed of your ICP automatically, because LinkedIn is an interest graph, not a follower graph.Get DMs and conversations started by people who already trust your thinking.Skip the cold outreach phase entirely.The Comment Quality BarNo teaching, no textbook tone, no "ChatGPT wrote this for me" energy.Lead with contrarian views framed without picking a fight.Add wordplay, wit, or one personal anecdote.Keep it to two or three lines.Always ask the author a question.The Post-Comment DM LoopDM the author of the post you commented on.DM other people who engaged in the comments.No agenda, just "coffee chat" energy.Invite them to your newsletter once trust is built.Send referrals their way and watch the favor return.The Anti-Predatory SaaS Pricing ModelLock in $39/month forever for the first 25 design partners.Add new data sources (Reddit, X) without raising the base price.Pass cost savings down to customers as the user base grows, not up.https://getchime.cohttps://aiforfounders.cohttps://linkedin.com/in/alihafizji/https://linkedin.com/in/estesryan/