At 26, Yusif Gurbanli has already worked at CERN, traded at J.P. Morgan, built aircraft for NASA, and finished a PhD reconstructing human knees with AI. Most people would call that scattered. Yusif calls it the whole strategy.

Yusif is the co-founder and CFO of AIdMD, a clinical AI platform tackling one of healthcare's most stubborn problems: the hours of documentation doctors take home every night, a habit so common that physicians have a name for it — pajama time. Before AIdMD, his path ran through a robotics world championship that got him recruited by NASA, a research project designing aircraft for Mars's near-nonexistent atmosphere, and a pivot into AI-driven bone reconstruction that became the seed of his company.

In this conversation, Yusif makes the case for the generalist: why range plus the ability to go deep on demand beats narrow expertise, especially now that AI has made depth-on-demand available to anyone willing to ask the right questions.

Highlights:

How a high school robotics championship led to a NASA recruitment offer

Why he turned down Cornell for a full ride at the University of Miami

The pivot from designing aircraft for Mars to reconstructing knees with AI

What 200+ physician interviews taught him about building healthcare software

The investor lesson that changed how he sees his own startup (call it "the ugly kid")

Why real founder confidence looks like a bridge across a canyon, not blind belief

The advice from a NASA director that got him through the hardest stretch of his PhD

Follow Founders & Empanadas for more conversations with founders who took the long way around. New episodes weekly on YouTube, Spotify, and Apple Podcasts. Connect with Yusif on LinkedIn or learn more about AIdMD at aidmdusa.com.

Hilary Mason was one of the most recognizable names in data science: chief scientist at bitly, founder of Fast Forward Labs, co-author of Ethics and Data Science. Then she walked away to build Hidden Door, a roleplaying platform where you step inside licensed story worlds with an AI narrator running the game. The catch? She calls herself a skeptic of most of the generative AI market, and she's building one of its most ambitious products.

Her resolution to that contradiction is the business model itself. Authors license their worlds directly, 30% of subscription revenue flows back to creators, and Hidden Door never trains models on their work. She founded the company the week before the pandemic and spent over five years building before charging a single player.

Host Joshua Eidelman sits down with Hilary over empanadas to get into ethics as strategy, why most AI products are designed wrong, and what it takes to win over authors and game developers who distrust the entire category.

In this episode:

Why she says ChatGPT is "the original sin of bad AI product design"

How aligning your business model with your principles has to happen on day one

The decision to route 30% of revenue back to the authors whose worlds power the platform

Why she runs a strongly synchronous remote team ("demos, dilemmas, and aspirationally, donuts")

The accidental pivot from a kids' product to grown-up fans

How Hidden Door moderates open-ended roleplay without an OpenAI model in the stack

Her one belief 99% of founders would disagree with

Subscribe for new episodes of Founders & Empanadas every week.
Watch on YouTube, listen on Spotify and Apple Podcasts.

Dr. Myra Ahmad graduated from medical school in 2022, looked at the system she'd just trained inside, called it dystopian, and decided to build something outside of it instead of starting a residency. Three years later, Mochi Health has served more than 500,000 patients across all 50 states.

In this episode of Founders & Empanadas, Myra and Joshua get into the strategy behind the build: why weight-loss medication was only ever a wedge into primary care, how she designed a three-sided marketplace where the best providers rise and the weakest wash out, and why she thinks the entire incentive structure of American medicine is broken.

She also shares a contrarian take that lands well beyond healthcare: in a post-AI company, stop hiring narrow specialists and hire generalists who can move between teams, because the tooling makes picking up new skills nearly free.

Highlights:

• Why GLP-1s were a go-to-market, not the actual business
• The post-AI hiring philosophy: generalists over specialists, and roles that aren't fixed
• Why doctors never get a raise, and what that taught her about incentive design
• How she draws the line between what AI handles and what only a provider should
• Why a $250 surprise bill is a symptom of healthcare's pricing black box
• How she reads marketplace reviews when everything defaults to five stars
• Building three software products at once without starving any side of the market

Subscribe to Founders & Empanadas for new founder conversations every week.

Rand Fishkin built Moz from a struggling web-design agency into a $60 million software company and watched venture capital quietly turn it from a business that served customers into one that served investors. His verdict, over pineapple empanadas: raising VC was the second-biggest mistake of his career. The biggest? Stepping down as CEO.

Rand co-founded SparkToro after Moz and now builds "customer-shaped" companies funded by friends, not funds, including a brand-monitoring tool with no AI in its marketing and a 1960s-Italy video game. He's candid about founder depression, the gap between promised and delivered equity, and why he once wrote $700,000 in personal checks to his former employees.

This is a founder-to-founder conversation about doing it differently and why that might be the only honest way left.

What you'll take away:

• Why Rand calls stepping down as CEO his single biggest career mistake and what he'd do instead

• How VC funding shifted 80% of his energy from product to pitching

• The "true lifetime value" math VCs ignore (and how it warps what you build)

• Why he wrote $700K in personal checks when Moz finally sold

• The SparkToro clickstream data showing search still outgrowing AI

• His low-risk, friends-as-investors funding model that repaid backers in 5 years

• The belief 99% of founders would disagree with and how it changes how he runs companies

Subscribe to Founders & Empanadas for candid, founder-to-founder stories. Watch on YouTube, listen on Spotify and Apple Podcasts.

Jenna Reback can taste words. Her own name tastes like blueberries, which is why she named her company Blueberry. She has synesthesia, a rare neuro-sensory condition that made childhood disorienting and lonely, and forced her to become obsessed with one question: how do you make someone else understand something they've never experienced? That question led her to Hollywood, then to Silicon Valley, and eventually to building a brand messaging agency that works with founders at every stage.

On this episode, Jenna joins Joshua for empanadas to make the case that in the age of AI, storytelling is the last moat standing. She shares the three-question framework she developed in TV writers rooms, explains why the thing founders are most tempted to sand off is usually their best asset, and delivers a genuinely contrarian take on Silicon Valley's obsession with biohacking and optimization culture.

What you'll hear:

• Why Jenna has never lost a pitch, and the TV writers room framework behind it

• The three questions that every founder's story needs to answer

• How she helped a fintech founder win over VCs and restaurateurs at the same time (using the same story)

• Why great products no longer sell themselves, and why great stories still do

• Her hot take: how you do one thing is NOT how you do everything and why the ruthless optimization culture is "soulless"

• Why AI is making storytelling more valuable, not less

Subscribe to Founders & Empanadas on YouTube, Spotify, and Apple.

Most social apps were built to make you feel connected without requiring you to actually be. Sanjay Guruprasad has been building against that assumption for eight years. His thesis: the only online interaction that replicates the way humans have always built real relationships is playing games together.

Sanjay is the founder of Rune AI, a multiplayer game platform and engine that's been processing two billion minutes of voice chat and, now thanks to AI, lets anyone build a full multiplayer game in under an hour. He did his PhD at MIT's Media Lab studying social networks, then spent a decade learning everything the research got wrong when it met the real world.

This conversation covers the pivot that ended a half-million-user product, what Among Us teaches us about quality, and why Sanjay is actively hiring fresh grads while the rest of the tech industry isn't.

Highlights:

• How Rune solved the 45-second drop-off problem and why it changes everything in consumer social apps

• Why shutting down a product with 500,000 monthly active users was the right call, and what Sanjay looked for before pulling the trigger

• The platform shift Rune had been waiting eight years for, and what happened when they released an MCP the day AI got good enough

• Why games are the only online medium that actually deepens a friendship over time

• The Among Us lesson: what the most elegant game of the last decade teaches about quality in an era of AI-generated slop

• Why Sanjay is hiring fresh grads, and the specific mindset he looks for that experienced engineers often lose

Follow Founders & Empanadas on [YouTube / Spotify / Apple Podcasts]. Find Sanjay at @sanjaypojo on LinkedIn and Twitter, and explore Rune at joinrune.com.

Andrea Mazzocchi defended her PhD, applied to Y Combinator, and watched the country shut down for COVID all on the same weekend. That was May 2020. By the end of the year, she had a wet lab running, a seed round closing, and a company called Known Medicine using 3D tumor organoids to predict which cancer drugs would actually work for individual patients.

Three years later, she sold it. Then started over.

In this episode, Joshua sits down with Andrea, Co-Founder and CEO of Play Health (YC F25), to talk about what it really took to build two YC-backed companies from scratch, what she learned selling the first one, and the single most uncomfortable thing a technical founder has to face: great technology is not a business strategy.

In this episode:

• Starting a company the weekend COVID shut everything down

• What it actually feels like to go from founder to babysitter after an acquisition, and why she left

• The mistake technical founders keep making at the intersection of science and business

• Why founder-led is almost always better than bringing in the resume

• Radical prioritization: why if ten things are a priority, nothing is

• Her hot take on wearables and personal health data (you're probably not using 70% of it either)

• Building a 4-person team that punches above its weight

Subscribe and listen to this episode of Founders & Empanadas with Andrea everywhere you get your podcasts!

Starting in 2003, years before anyone was using the term, Yu-kai Chou began developing what would become the Octalysis Framework: a model of human motivation built around 8 core drives that influence every decision we make. He gamified his own life first. Then his companies. Then Fortune 500s. Then governments.

Now he's one of the most sought-after behavioral designers on the planet. He's been to Ukraine (during the war) to advise on gamification strategies for the country. He's the author of Actionable Gamification and 10,000 Hours of Play, his reframe of Malcolm Gladwell's famous concept. His clients include Google, Duolingo, and national governments.

In this episode of Founders & Empanadas, we get into:

• Why he tells founders to "optimize for failure" and why it might be the most counterintuitive success strategy you'll hear

• The VC pattern he experienced 4-5 times: being called "crazy" and "stupid" before the world finally caught up

• Why older generations actually respond better to gamification than younger ones, and what that means for product design

• The dark side of gamification: how Black Hat mechanics tap into your survival instincts and trap users into addiction

• What 10,000 Hours of Play really means and how to apply it to your work and life right now

• What happens every time a big company acquires a startup and why it ends the same way almost every time

• How he went from a kid struggling in a Taiwanese school to advising the president of a country at war

Yu-kai is sharp, funny, and genuinely one of the most interesting people I've sat down with. This one will change how you think about your time.

🎙️ Listen on Spotify, Apple Podcasts, or wherever you get your podcasts.

📺 Watch on YouTube.

Jessica Murrey won a Regional Emmy at 24 for an anti-child abuse campaign, then spent seven years training young activists and former extremists in countries recovering from genocide and civil war: Myanmar, Burundi, Nigeria, Colombia. She came home asking: how do you scale this?

The answer was a video game.

Jessica co-founded Wicked Saints Studios with a behavioral scientist and a former senior Pokémon GO engineer. They raised $5M+ from Riot Games, Precursor Ventures, and Reid Hoffman, putting Jessica among fewer than 100 Black women in history to cross the $1M venture threshold. Their game, World Reborn, runs on one mechanic no other game uses: you can't buy progress. You earn it by doing real things in the real world. Brands like e.l.f. Beauty and Discord are integrated not as ads, but as quests. In an industry where brand click-through rates average under 1%, World Reborn is hitting 31%.

In this episode:

• Why peacebuilding in conflict zones and mobile gaming for Gen Z are solving the same problem

• What the "Tattoo Method" is and why it works when traditional behavior change doesn't

• The fundraising reality of being a Black woman founder (0.3% of VC went to Black women in 2023)

• How World Reborn broke the brand ROI model that's stumped the rest of the gaming industry

• The question about startup culture she never gets asked: does "more money and more power" actually make your life better?

• A three-step conflict framework from the warzones, built for co-founder disputes, fractured teams, and difficult investors

One of the most unusual founder backgrounds Joshua has ever encountered on this show. Worth every minute.

🎙️ Listen on Spotify, Apple Podcasts, or wherever you get your podcasts.

📺 Watch on YouTube.

Sahin Boydas moved from Turkey to San Francisco in 2012 with no network, no warm intros, and a conviction that remote work was going to change everything, about a decade before COVID made it unavoidable.

What followed was four companies, two exits (MovieLaLa to Gfycat, RemoteTeam.com to Gusto in 2021), 180+ angel investments including Anthropic and OpenAI, and a ranking as the #1 Most Active Angel Investor in 2024. He's now building Levy, an AI-native neobank for startups and he has zero interest in giving you soft takes.

What we covered:

• How he sold RemoteTeam.com to Gusto and what actually kept him there for 3.5 years after the deal closed

• Why post-exit founders are the single most reliable predictor of building a unicorn (the Super Founders data is wild)

• Why he thinks 90% of desk jobs are gone and why he's weirdly optimistic about it

• His rule: if an employee says AI doesn't give them good results, fire them immediately

• Why empathy (not hustle, not grit) is the #1 skill every founder actually needs

• How AI just handed every founder outside Silicon Valley access to the knowledge the Valley spent decades hoarding

• Why founders who ask for permission to go to the dentist have already missed the point

If you're building something, this episode of Founders & Empanadas is worth your full attention. Subscribe wherever you get your podcasts!