AI for Founders with Ryan Estes

A 6-person team just built in 3 months what took 18 months and $2 million the last time around. That's not a productivity story. That's a story about the ground shifting under an entire trillion-dollar industry. Tim Lidman knows consulting from the inside. He grew up in the collaboration industry: Webex before Cisco bought it, SuccessFactors before SAP bought it, then a decade helping run...

Jason Katz popped his LCL three weeks ago scrambling out of a leg entanglement, and honestly, that injury is the whole episode in miniature. You get excited, you move fast, you stand up into a hold you did not see, and something structural gives. In this What It Do check-in, Jason (co-founder of Kindling Solutions, back for another round) and Ryan trade war stories from the two weeks that turned b...

Most founders think the endgame is IPO or bust. Todd Furniss built a company that offers a third door: sell to someone who keeps your entire team, hands leadership three to five year employment agreements, and then drops patented AI into your operations like a turbocharger into a truck that's been stuck in third gear for a decade. Todd is the CEO and co-founder of AI Squared, formally AIAI Hol...

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...

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 th...

Your blood pressure spikes the moment the cuff goes on. You're sitting on crinkly paper in a cold exam room, and the number on the screen may say more about the moment than your everyday life. It's the classic "white coat effect," and it doubles as a metaphor for one of healthcare's biggest challenges: we often measure people at isolated moments instead of continuously, then...

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...

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...

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, po...

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 walk...

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 eart...

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...

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...

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 rare...

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 ou...

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...

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 s...

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...

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....

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....

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 f...

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 i...

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...

Your IT team is drowning. Every "how do I get access to..." Slack message you fire off is making it worse. And while everyone in 2026 is busy debating whether AI is coming for the C-suite, Tom Bachant has spent the last four years quietly automating the layer of work that actually keeps companies running. The help desk. The ticket queue. The Jira dashboard you've been ignoring for th...

Picture St. Louis, 1849. Two men with a bottle of champagne and a brutal choice: go north for beaver pelts, or go south chasing gold in California. Joris Delanoue does not even blink. He picks the gold. Not for the metal. For the belief. That single line tells you everything about this conversation. Joris, co-founder and co-CEO of Fairmint, has spent the better part of two decades pushing into fro...