About Ivan Van Norman

Ivan Van Norman is a true powerhouse of indie tabletop publishing and media innovation, bringing over 15 years of deep industry expertise to the table. Our paths cross all the way back to the very first year Gen Con introduced Entrepreneur’s Alley, where our tiny 10x10 booths were literally shoved into the back corner of the convention hall, facing a wall right next to the food court. While I was out there hawking the first print run of Ascension, Ivan was launching Hunters Entertainment. Since then, Ivan has carved out an incredible track record, serving as an executive producer and host at Geek & Sundry during the wild dawn of the web-streaming boom, helping lay the early foundational blocks for massive cultural phenomena like Critical Role, and co-owning Hunters Entertainment. He’s the publisher behind brilliant, boundary-pushing projects like the silent, text-messaging RPG Alice Is Missing. In this episode, we discuss the brutal realities of transitioning from a broke creator to a successful studio owner, how shifting mediums completely transform the mechanics of storytelling, and why your graveyard of discarded ideas is secretly your greatest design asset.

Ah-ha! Justin’s Takeaways

* Everybody Prepares You for Failure, Nobody Prepares You for Success: When you’re broke and just starting out, you are completely free to take massive risks because you have absolutely nothing to lose. However, the moment an indie project hits it big, the landscape completely flips. Ivan shares a wild reality check about running his first hit Kickstarter as a sole proprietor and suddenly getting hit with a massive personal tax bill he didn’t see coming. Success brings structural obligations to payroll, to investors, and to an audience that wants you to repeat your tricks.

* The Medium is the Mechanic: If you want your creative stories to break through the modern cultural noise, you have to design explicitly for the technology where your audience actually lives. Felicia Day and Geek & Sundry did it by leveraging the wild west of early YouTube and Twitch to unlock long-form TTRPG streaming. Alice Is Missing did it by turning a standard smartphone group text into an intensely emotional narrative engine. During our chat, Ivan’s insights actually inspired me start work on a brand-new design concept right at the table: how to build an ultra-short-form video RPG engineered entirely for Shorts, Reels, and Twitch.

* Less Money Equals More Radical Execution: Starting out broke right out of college gives you a massive, counterintuitive edge, because without a cash cushion, you are forced into a level of radical execution you just can't fake. Ivan and I launched right in a brutal recession, building display tables out of inventory boxes and dragging ammo cans down the hot streets of Indianapolis. That said, the real secret to surviving over the long haul as a serial entrepreneur is a beautiful touch of amnesia. We are naturally wired to avoid pain, and if you perfectly remembered the bone-deep exhaustion and near-failures of a launch, you'd never take a big risk again. You need that selective memory loss to trick yourself into thinking "this next launch will be smooth" just to find the sheer audacity to stand at the starting line again. It acts as a psychological shock absorber, wiping away the baggage of past failures so you can always approach a blank sheet of paper with total confidence.

About Zvi

My history with Zvi Mowshowitz goes back over 20 years to our days as teammates on the Magic Pro Tour, where we won a Grand Prix and top-8ed a Pro Tour together. After his competitive gaming career and a stint designing games at Wizards of the Coast and heading up a Cyberpunk TCG design team in Denver, Zvi took his unique systems-thinking mind into high-stakes finance. He managed risk as a professional bookmaker in sports betting, traded crypto for a hedge fund, and worked quantitative trading desks at firms like Jane Street. Today, he’s focused his incredible intellect on the world of artificial intelligence, writing five times a week at his blog, Don’t Worry About the Vase, tracking the breakneck evolution of large language models and the critical safety challenge of AI alignment. In this episode, we dive deep into the math of pattern recognition, our wild days on the Pro Tour, the high-stress realities of trading, and how to navigate the massive societal shifts coming with AI. Zvi delivers insights on rationality and adaptability that will resonate with anyone trying to think clearly in a rapidly changing world.

About Nate Heiss

Nate Heiss is a true game design chameleon. His 25-plus year career spans from competitive Magic: The Gathering play to designing iconic cards like Goblin Guide at Wizards of the Coast. He then took those skills into the AAA video game world, working as a designer and creative director at studios like LucasArts and PopCap on massive mobile hits like Plants vs. Zombies Heroes. Nate and I have been geeking out about game design since we met on the Magic Pro Tour in the late 90s, and now we’re finally teaming up on Gundam Assemble, an upcoming tabletop skirmish miniatures game. In this episode, we dive deep into the differences between physical and digital design, the ethics and realities of free-to-play business models, and how to capture the elusive magic of discovery in an internet age. Nate delivers profound insights that will resonate with anyone building games or trying to navigate a creative career.

Justin’s Ah-Ha! Moments

* The Shift From Player to Designer Mindset: Nate and I discuss a classic trap many pro players fall into when they start designing: trying to "beat" the players. It's easy to bring a competitive ego into R&D and focus on squashing dominant strategies to prove how smart you are. But great design isn't about winning; it's about crafting a fun experience. Once you soften that competitive edge, you realize your true goal is to empower players to make their own discoveries.

* The Economics of Free-to-Play Dictate Design: We tackle the controversial topic of free-to-play games. Nate points out that companies succeeding in this space aren't necessarily making "better" games; they are mastering live service and content costs. If a studio can "turn the crank" and produce engaging content at a fraction of the cost, they gain a massive competitive advantage. It shifts the design problem from just making an great game (which is table stakes) to efficiently delivering ongoing value over time.

* Roguelikes are the Modern Gold Rush: I've always wanted to recreate the feeling of opening an early Magic pack—when nobody knew the optimal strategies and everything felt like an untamed frontier. Nate brilliantly identifies that roguelikes are where this feeling lives today. By taking a core loop and exploding it into a massive, randomized possibility space on every run, roguelikes force players to adapt and experiment, capturing that communal feeling of discovery over and over again.