How to Stay Customer-Obsessed and Never Investor-Obsessed in Running Your Business with Rand Fishkin

How to Stay Customer-Obsessed and Never Investor-Obsessed in Running Your Business with Rand Fishkin

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.

Why Storytelling Is the Last Moat You Have Left, with Jenna Reback

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.

Why Gaming is 10x Better for Human Connection Than Social Media Ever Will Be | Sanjay Guruprasad

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 [http://joinrune.com].

The 2x YC-Backed PhD Founder Who Learned Why Great Technology Is NOT Enough | Andrea Mazzocchi

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!

10,000 Hours of Play: Stop Grinding, Start Playing | Yu-kai Chou

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.