AI for Founders with Ryan Estes

There is a moment in every founder's journey where they realize the bottleneck in their pipeline is not their product, not their pricing, and not their pitch. It is time. Specifically, the time between when a prospect raises their hand and when someone, or something, responds.

Will Del Principe discovered this the hard way. At 16, he was a solar sales rep dialing through a list of thousands of warm leads on an iPad, burning out after five or six calls, leaving a fortune in uncontacted interest sitting in a CRM. A decade later, he is the head of growth at Thoughtly, an AI voice agent platform that calls those same kinds of leads within 10 seconds of form submission, runs 13,000 calls a month for a single client, and once had to be reprogrammed after one of its agents agreed to go get coffee with a prospect.

This episode is about what happens when you stop asking humans to do what machines can do endlessly, and start letting your best salesperson work around the clock without ever needing a break.

https://www.thoughtly.com/

https://www.linkedin.com/in/will-del-principe-57b18b2a5/

⁠https://www.linkedin.com/in/estesryan/⁠

⁠https://aiforfounders.co⁠

⁠⁠https://kitcaster.com/application ⁠⁠

⁠⁠https://ryanestes.info⁠⁠

Guest: David Karandish, CEO and Co-Founder of Capacity.com

In December 2016, the top-selling product on Amazon was not a toy, a book, or a video game. It was Amazon's Alexa. For most people, that was a holiday novelty. For David Karandish, it was a starting gun.

David had just finished one of the most successful runs in the history of vertical search. He built Announced Media, acquired answers.com, merged the two companies, scaled them into a powerhouse, and sold the whole thing for $900 million. He took five months off. He made his laundry list of what to do next, somewhere around 50 ideas. Forty were terrible. A handful were decent. One made him feel like he would regret skipping it for the rest of his life.

That one became Capacity.

He founded it in early 2017, before the world understood what AI was about to become. Blockchain was the darling. AR and VR were getting the hype cycles. AI was maybe fourth on the list of things people were excited about. David bet on fourth place, and he was right.

But here is where the real story starts. Because building Capacity was not a straight line. In the early days, the product worked better for some customers than others, and the market was sending a confusing signal. Small companies had the problem but not the budget. Enterprise companies had the budget but needed security certifications, compliance frameworks, and infrastructure that a scrappy startup did not yet have. David built those things. SOC 2. HIPAA compliance. Role-based access controls. And while he was building the enterprise credibility, something else was happening: his customers kept asking for more.

Not more features inside one product. More products that actually talked to each other.

Over and over, David kept hearing the same thing. "We are so tired of duct-taping solutions together. We don't want five vendors. We want one platform that works." He heard it a dozen times before he finally went to his executive team and said, "I think I know what we need to build." They looked at him like he had three heads.

He built it anyway.

Today, Capacity serves 20,000 customers, including T-Mobile, Verizon, Nike, and American Express. Annual revenue has surged past $50 million. And the strategy behind all of it is something David calls the Compound Startup.

https://capacity.com/

https://www.linkedin.com/in/davidkarandish/

https://www.linkedin.com/in/estesryan/⁠

⁠https://aiforfounders.co⁠

⁠⁠https://kitcaster.com/application ⁠⁠

⁠⁠https://ryanestes.info⁠⁠

There is a moment in every founder's journey where they realize the map they were given was wrong. The old map said: have an idea, find a developer, wait months, launch, iterate. David Alonso, co-founder of Bloom and ETH Zurich robotics graduate turned mobile app revolutionary, is handing founders a new map. One where the distance between idea and working product is measured in minutes, not months.

David didn't plan to build Bloom. He planned to build robots. But somewhere between reinforcement learning research and quadrupeds, he fell in love with the tight feedback loop of app development, met a world-class design engineer in his co-founder, and the two of them started following an obsession that eventually led them through Y Combinator, a $3.5 million raise closed before Demo Day, and a product that left investors texting their friends mid-demo saying it was the best tech demo they had ever seen.

This episode is the story of what happens when you decide the bottleneck is not code. It is imagination.

The Core Problem Bloom Is Solving

Building a mobile app used to take David and his co-founder four months from idea to having it on someone else's phone. Four months. And that was with two technical co-founders who knew exactly what they were doing. For a non-technical founder, the timeline was effectively infinite. Bloom collapses that timeline to minutes by combining three opinionated technology choices into a single agentic coding experience:

• Expo as the front-end framework, enabling one codebase to deploy to web, iOS, and Android simultaneously
• Convex as the backend, providing real-time sync between devices out of the box, full type safety, and a database that just works without configuration
• App Clips as the distribution layer, an underutilized Apple feature that lets anyone open a fully native app from a single link without visiting the App Store, downloading TestFlight, or entering an invite code

https://bloom.diy/

https://www.linkedin.com/in/david-oort-alonso/

⁠https://www.linkedin.com/in/estesryan/⁠

⁠https://aiforfounders.co⁠

⁠⁠https://kitcaster.com/application ⁠⁠

⁠⁠https://ryanestes.info⁠⁠

Jesse Marble did not set out to build a typical VC firm. Growing up steeped in Colorado culture, watching people chase outdoor adventure, physical health, and something resembling a meaningful life, he kept noticing a gap. We have more technology in our pockets than it took to land Americans on the moon. And yet, by almost every subjective measure, people are not thriving more. They are thriving less.

That tension became Wildwood Ventures, a Denver-based early-stage VC firm with a deceptively simple thesis: invest in human flourishing through technology. Not hiking apps. Not yoga trackers. The whole sprawling category of what it actually means to be healthy, connected, and alive in the modern world.

What Jesse brought to this episode was not a polished fund deck or a rehearsed pitch. It was something rarer: a practitioner's honest account of what he sees every week sitting across from founders, scoring pitches in real time, and asking himself whether he would put his own money on the line.

The answer, he admits, is increasingly complicated.

https://wildwood.vc/

https://www.linkedin.com/in/jessemarble/

⁠https://www.linkedin.com/in/estesryan/⁠

⁠https://aiforfounders.co⁠

⁠⁠https://kitcaster.com/application ⁠⁠

⁠⁠https://ryanestes.info⁠⁠

There's a moment in every founder's journey where the market stops being theoretical and becomes deeply personal. For Lucas Consoli, co-founder of EmpathEQ, that moment happened in a hospital room, watching his mother in an induced coma for two weeks, his emotional state entirely at the mercy of whichever nurse happened to be on shift. Some had zero empathy. Some brought calm into chaos. That gap, that wildly inconsistent human experience inside one of the most high-stakes environments on earth, became the foundation for everything EmpathEQ is building.

Lucas grew up in Argentina, a country he describes as one that forges entrepreneurs not through comfort but through necessity. When institutions can't be trusted, you build your own moral compass. You develop a muscle for solving problems that most people would walk away from. He took that muscle to Berlin, co-founded two companies without speaking German, met his American wife, and eventually landed in Cincinnati with a green card, a vision, and a co-founder, Alex, who had five exits to his name and the capital to fund the first six months of the dream.

The problem EmpathEQ is solving is enormous. Nursing burnout is at crisis levels. A significant portion of the workforce is leaving the profession. And the root cause isn't clinical incompetence. It's emotional overload from interactions that nobody ever trained them to handle. Angry family members. Anxious patients. Charged situations that escalate in seconds. The traditional solution has been to hire an actor, schedule 200 students, give each of them three minutes of practice once a year, and hope it sticks. EmpathEQ blew that model up entirely.

Their platform puts nurses inside AI-powered simulations where a digital patient or family member reacts in real time to the nurse's verbal language, tone, facial expressions, and body posture. The AI orchestrator reads all of those signals and selects the next scene from a library of pre-rendered cinematic moments, choosing the response the patient would realistically give based on how the nurse is showing up. Afterwards, the nurse gets a full feedback report. Where they looked. How they sounded. Whether they validated emotions or bulldozed through them. It's a driving range for human connection.

The tech stack is a hybrid of AI and cinematography because fully generative real-time video isn't there yet. Rather than wait for the technology to catch up, Lucas and his team engineered around the constraint, and the result is something hospitals and nursing schools are lining up to use. Sixteen institutions are already collaborating. None have said no. The next step is getting them to pay, and the pre-seed round of $600K is still open for one strategic partner, ideally from health systems, nursing staffing agencies, or higher education.

The conversation also went deep on the philosophy of building, the danger of chasing exits without passion, the cognitive overload epidemic in the founder community, and why studying sociology or psychology might be the single smartest move a college freshman could make in the age of AI.

Lucas isn't just building a company. He's building a case that empathy is a trainable skill, that soft skills deserve hard infrastructure, and that the healthcare system's most urgent problem isn't a drug or a device. It's the conversation in the hallway.

https://empatheq.ai/

https://www.linkedin.com/in/lucas-donato-consoli/

⁠https://www.linkedin.com/in/estesryan/⁠

⁠https://aiforfounders.co⁠

⁠⁠https://kitcaster.com/application ⁠⁠

⁠⁠https://ryanestes.info⁠⁠

When the Market Is a WhatsApp Group, That's Your Opportunity

Some of the best startup ideas don't come from pitch decks. They come from watching thousands of people make high-stakes decisions inside a Facebook group, realizing there is no trusted infrastructure, and deciding to build it yourself.

That's exactly what Francesco Hayes did. As co-founder and CTO of Luxxera, he spotted one of the messiest, most fragmented, and most consequential markets on earth: medical tourism. Specifically, the booming industry of people flying abroad to get cosmetic procedures done at a fraction of US prices. Hair transplants that cost $50,000 stateside can be had in Turkey or Greece for $2,500 to $5,000. IVF that runs $70,000 in the US costs roughly $5,000 at a top Greek hospital. The demand is massive. The information infrastructure is basically nonexistent.

Francesco and his co-founder Nick didn't just see a gap. They walked into it, sometimes literally posing as patients to vet clinics before revealing who they were. What they built is part marketplace, part knowledge base, part concierge service, and 100% founder-brained.

The Dual-Sided Marketplace Framework

Running a two-sided marketplace means you are always solving two problems at once. Francesco broke down how Luxxera manages the tension between supply and demand.

On the clinic side:

• Free onboarding, no upfront cost to the clinic
• Luxxera provides booking systems, payment processing, and CRM infrastructure
• Most clinics currently run operations entirely through WhatsApp, so even basic tooling is a massive upgrade
• Clinic quality is validated through peer-review surgical organizations like ISHRS and FUE Europe, plus in-person site visits by the Luxxera team

On the patient side:

• A structured intake assessment narrows recommendations to two of five vetted clinics
• Transparent, itemized pricing with a 10 to 15% fee added on top of the clinic's quote
• Full concierge support throughout the entire patient journey
• Surge pricing planned for seasonal demand shifts, like winter being the peak season for hair transplants

https://luxxera.com

https://www.linkedin.com/in/francescohayes/

⁠https://www.linkedin.com/in/estesryan/⁠

⁠https://aiforfounders.co⁠

⁠⁠https://kitcaster.com/application ⁠⁠

⁠⁠https://ryanestes.info⁠⁠

There is a certain kind of founder who, after building and exiting a company, does not slow down. They just get quieter about it. Colin McIntosh is that founder. He sold Sheets and Giggles, the irreverently named sustainable bedding brand he bootstrapped into a multi-million dollar e-commerce operation, and then he did what most founders say they will do and almost never do: he kept building, but only the things he actually cared about.

This conversation covers the real state of the 2026 job market, the counterintuitive content strategy that put SheetsResume.com at the top of Google without a single AI-generated word, and the framework Colin uses to decide which ideas are worth his time. Along the way, it takes a detour through Babylonian flood myths, float tanks, and a giraffe-shaped carafe business that may or may not be a real thing.

WHY THE JOBS REPORT ISN'T TELLING THE WHOLE STORY

Colin breaks down the 2025 labor market with the clarity of someone who has seen thousands of resumes and placed hundreds of executives. The headline numbers look stable, but the underlying picture is messier.

• The US lost jobs in 2025 outside of healthcare, with healthcare accounting for roughly 90% of all new job creation
• Monthly job creation averaged a fraction of 2024's pace, with 2024 sitting around 149,000 jobs added per month
• AI is manifesting primarily as a payroll freeze, not mass layoffs, as companies wait to understand what they can automate before committing to new headcount
• Geopolitical instability, on-again-off-again tariffs affecting retail and its roughly $7 to $8 trillion slice of the US economy, a 40% drop in international tourism, and 300,000 government workers flooding the private job market are all compounding the pressure
• The people suffering most are those laid off in 2025 who cannot find work after six, twelve, or eighteen months of searching

https://sheetsresume.com/

https://readynda.com/

https://www.rivierapartners.com/

https://www.linkedin.com/in/colindmcintosh/

⁠https://www.linkedin.com/in/estesryan/⁠

⁠https://aiforfounders.co⁠

⁠⁠https://kitcaster.com/application ⁠⁠

⁠⁠https://ryanestes.info⁠⁠

There's a place in Denver, inside a buzzing AI builder clubhouse, where the future gets stress-tested out loud every Wednesday night. That's where this conversation happened, and it did not go the direction you'd expect.

Carson Vest is an investment associate at Denver Ventures, a generalist fund covering pre-seed all the way to Series B. She sees everything. Hundreds of founders, hundreds of pitches, hundreds of ideas competing for the same finite pool of attention and capital. And yet the most radical thing she said had nothing to do with a hot deal. It was this: you might not need us.

That single idea runs like a thread through this entire conversation, pulling at the assumptions most founders carry into every investor meeting without even realizing it.

The Frameworks You Need to Steal

The Founder DNA Thesis: Why the person always comes before the product

• Denver Ventures bets on founders first, especially at pre-seed and seed
• Prior company experience, big tech background, or deep channel relationships signal real distribution potential
• If you can't sell the vision to an investor in a casual conversation, how will you sell it to a team, a customer, or a market?

The Distribution Co-Founder Gap: The missing piece on most cap tables

• Most founders plan to hire for distribution after raising, but bringing that person in as a co-founder from day one dramatically increases investability
• The strongest founding teams Carson sees came up together, school friends, former colleagues, people who already trust each other under pressure
• Distribution is not a marketing problem. It is a survival problem.

The Moat Has Moved: Why code is no longer defensible

• An MVP that cost $320,000 and 18 months in 2022 now costs $20 and a week
• If your only edge is the technology, someone with a Claude account can clone you by Friday
• The new moats: proprietary data, founder network, channel relationships, and obsessive domain expertise

The VC Gut Check: The question every founder should answer honestly

• Carson asks founders point blank: why do you actually want VC money?
• Many founders admit they just assumed it was the next step
• Bootstrapping to $500k or even $1M ARR may give you more leverage, more equity, and more freedom than a seed round ever could

The Retention Signal VCs Actually Watch

• High AI margins look great on paper, but paradoxically can signal low usage
• Investors want to see high inference costs because that means users are actually on your platform
• Retention is the metric that separates a product people want from a product people try once and forget

The Agentic Shift: Where the smart money is moving post-ChatGPT

• The infrastructure layer, models, GPUs, wrappers, is maturing
• The next wave is workflow automation and vertical AI that disappears into the background
• The winner is not the best chatbot. It is the tool that makes the task vanish entirely.




https://denverventures.co/

https://www.linkedin.com/in/carson-janae-vest/

⁠https://www.linkedin.com/in/estesryan/⁠

⁠https://aiforfounders.co⁠

⁠⁠https://kitcaster.com/application ⁠⁠

⁠⁠https://ryanestes.info⁠⁠

Josh Gilmer on AI video journaling, founder self-awareness, searchable memory, and the future of personal growth

Most founders say they want self-awareness.
What they usually mean is they want a cleaner notes app.

In this episode of AI for Founders, Ryan Estes sits down with Josh Gilmer, founder of Historic, to explore a wild and increasingly relevant idea: what if the most valuable founder data is not in your CRM, your calendar, or your analytics dashboard, but in the raw, unfiltered way you talk when nobody is grading the performance?

Josh argues that handwritten journaling and polished note-taking often miss the point. By the time a thought hits the page, it has already been edited, softened, and made presentable. Historic takes the opposite path. It uses video journaling plus AI to capture tone, posture, energy, hesitation, and emotional context, then turns that into searchable, structured memory.

The conversation starts with founder productivity and quickly opens into something bigger: burnout detection, AI coaching, parenting, second brains, the future of memory, and whether technology will help humans reconnect or just become even more insulated.

This one is for founders building hard, thinking fast, and wondering whether the biggest blind spot in the company might be the person running it.

What you’ll learn

• Why written journaling often captures polished thoughts instead of real thoughts

• How video journaling can reveal emotional and cognitive patterns text misses

• Why searchable personal memory may become a founder advantage

• How AI could eventually detect burnout, mood shifts, and recurring decision patterns

• Why productivity might shift from doing more to remembering better

• How Historic is being built and positioned for founder adoption

• Why Josh believes AI should strengthen human relationships, not replace them

https://historic.app/

https://www.linkedin.com/in/joshuagilmer/

⁠https://www.linkedin.com/in/estesryan/⁠

⁠https://aiforfounders.co⁠

⁠⁠https://kitcaster.com/application ⁠⁠

⁠⁠https://ryanestes.info⁠⁠

This conversation starts with a blunt idea: most AI companies are moving fast enough to impress people, but not carefully enough to survive themselves. What looks like momentum from the outside can be chaos on the inside, and James Everingham makes the case that the next real layer of AI infrastructure will not be another flashy model. It will be the systems that govern, audit, orchestrate, and preserve what those models and agents actually do.

From there, the story widens. James pulls from years inside Meta, where he worked on developer infrastructure and saw firsthand what happens when agentic systems start touching real enterprise environments. The lesson was not that agents are weak. It was that they are powerful enough to require governance, access controls, traceability, and compliance like any serious employee or internal system.

The conversation then moves into a bigger historical frame. Browsers, spreadsheets, infrastructure shifts, platform wars, and the collapse in the cost of intelligence all become part of the lens. James argues that we are not just watching better tools arrive. We are watching corporate infrastructure reorganize around agents, much like the internet reorganized business around the browser. The winners may not be the companies with the loudest demos, but the ones that can make their systems stable, reusable, secure, and multiplayer.

It also gets personal. James talks about building again after a successful career, the difference between burnout and lack of inspiration, why network matters more than people admit, and why founders should not start companies just to start companies. They should wait for the idea they cannot ignore.

https://guild.ai

https://www.linkedin.com/in/jevering/

⁠https://www.linkedin.com/in/estesryan/⁠

⁠https://aiforfounders.co⁠

⁠⁠https://kitcaster.com/application ⁠⁠

⁠⁠https://ryanestes.info⁠⁠