We Thought It Would Be Easy

Jordan Weisman & Jonathan Grant•www.wethoughtitwouldbeeasy.com

It’s all fun and games until someone loses an eye ... or millions of dollars. This podcast drags mad geniuses and bold creators from every corner of interactive entertainment out of their comfort zones to answer the question, 'What the f**k were you thinking?' Expect brutally honest stories, creative courage under fire, and practical insights that’ll inspire (or warn) anyone daring enough to chase magic.

Last refreshed: August 15th, 2025 at 5:22 PM ⓘ

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Episodes

Ed Fries: The Father of the Xbox is Really a Hacker at Heart

Ed Fries joins hosts Jordan Weisman and Jonathan Grant to show how a teenage arcade hacker became the exec who helped turn Microsoft into a gaming powerhouse. Curiosity first, constraints as fuel, and a ruthless respect for shipping, that hacker ethos still drives how he works & builds things today. Check out Ed's venture fund 1Up Ventures - where he's building a community of the most talented, experienced, and creative independent game developers in the world. https://1upfund.com/ Don't for...

Aug 14, 2025•1 hr 38 min•Ep. 6

Daniel Dociu: From Guild Wars to The Expanse, Making Art That Serves Story First

Art Director & visual powerhouse Daniel Dociu joins Jordan Weisman and Jonathan Grant to torch “style bibles,” praise imperfections, and argue that art should grow like aged cheese - slow, organic, story-first. He recalls sketching Crimson Skies, turning Guild Wars into a “playable painting,” and painting The Expanse covers with zero notes. The trio spar over rapid prototyping, AI’s coming shake-up, and how small, gutsy teams can still out-create lumbering megaprojects. Check out Daniel's IN...

Jul 31, 2025•1 hr 16 min•Ep. 5

Mitch Gitelman: On Building MechCommander, Shadowrun, Battletech - and Why Kindness Wins

Mitch Gitelman: Building MechCommander, Shadowrun, Battletech - And Why Kindness Wins Game-making maestro Mitch Gitelman sits down with Jordan and Jonathan to spill the wild origin story of how “a kid who didn’t know what a pixel was” bluffed his way into Sony - and then built classics like MechCommander, Shadowrun Returns, and BattleTech. From goat-pasture negotiations and Microsoft war stories to why “improvise, adapt, overcome” (and a lot of kindness) still beat crunch and corporate ego, this...

Jul 24, 2025•1 hr 26 min•Ep. 4

Kevin Konrad Hanna: From Game Developer to Directing the Hit Hellboy Documentary and Taking Home Film Awards

Our guest this week is Kevin Hanna - who started as a scrappy game developer before making an unlikely leap into directing documentaries, including the acclaimed film about Hellboy creator Mike Mignola. He joins Jordan and Jonathan to share candid insights about the creative hustle, turning lunch-table dreams into award-winning reality, and why true creativity means making your own luck, even when the odds are against you. Watch Mike Mignola: Drawing Monsters on Amazon Prime: https://amzn.to/4df...

Jul 16, 2025•59 min•Ep. 3

Chris Taylor: Creator of Total Annihilation on Big Risks and Never Asking Permission

In this episode, storied game designer Chris Taylor (Total Annihilation, Supreme Commander) joins Jordan Weisman and Jonathan Grant for a candid conversation about fearless creativity, costly mistakes, and why groundbreaking games often mean never waiting for permission. From pioneering real-time strategy to surviving the brutal highs and lows of independent studio life, Chris shares his boldest bets - and what it truly takes to deliver on ambitious game-design dreams. Check out Chris' web‑based...

Jul 08, 2025•1 hr 31 min•Ep. 2

Justin Gary: Creator of Ascension & SolForge on Crafting Games and Taking Chances

In this episode, Jordan Weisman and Jonathan Grant talk with renowned game designer Justin Gary, discussing his journey from winning Magic: The Gathering championships to creating successful games like Ascension and SolForge Fusion. They explore the evolution of game design, the importance of creativity, the challenges of crowdfunding, and the impact of AI on the industry. Justin shares insights on navigating risks, the creative process, and the significance of building a community around game d...

Jul 01, 2025•1 hr 8 min•Ep. 1

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