Rolling for Innovation: What D&D has taught me about embarking on a startup quest

Liz Dennett, PhD
5 min readNov 17, 2023

By Liz Dennett, CEO of Endolith and a Level 20 D&D Enthusiast

A typical table layout during a D&D day in my house. Paper charachter sheets forever ❤

Embarking on a Startup Quest

Hello, fellow startup adventurers and corporate dungeon masters! I’m Liz, CEO of Endolith where by day I’m focused on steering a ship through the tumultuous seas of a heavy technology startup working to set our eyes on a cleaner energy future. In this journey, I’ve managed to survive some death saves, earn some feats, and have more than my fair share of rolls for initiative. In the spirit of sharing these entertaining tales, I wanted to pull together some of the most impactful lessons where the venn diagram of “things that are crucial for Dungeons & Dragons (D&D)” overlaps with “things that I learned navigating the challenging world of startups.”

Making your roll is key to getting in on the action. And yes, I need *all* of these dice

Rolling for Initiative: The Startup’s First Bold Move

In D&D, rolling for initiative is about seizing the moment with courage. It’s also about rolling that D20 to see when you get to make your move in combat. In the startup world, this translates to making that first bold move into the market. Imagine unveiling a disruptive product in a crowded space — it’s like a wizard casting a spell (ahem…Fireball) in a crowded tavern. This initial leap requires tenacity and belief in your vision, much like a Paladin’s unwavering faith. It’s about identifying a gap, like a hidden trapdoor in a dungeon, or the ability of microbes to fundamentally shift the amount of copper we have in the global energy transition, and diving in with the agility of an Elven Rogue with sneak attacks.

Eldritch Blast: Innovation as Your Arcane Weapon

Spoiler alert, I have a hidden soft spot for Eldritch Blast. I’ve been known to multi-class or take on a feat just to have this cantrip. If you don’t know what that means, don’t worry: Eldritch Blast is a powerful attack that scales as you do. It also symbolizes the power of innovative thinking in a startup.

Think of it as your startup’s unique offering, a spell that sets you apart. When faced with a competitive market, unleashing your ‘Eldritch Blast’ — be it a unique technology, a novel business model, or an unconventional marketing strategy — can disrupt the status quo, much like how a well-placed spell disrupts a goblin ambush. It’s about channeling your inner wizard to conjure solutions that are both creative and impactful, and that you can use even if you’re out of spell slots.

Chaotic Good: Ethical Agility in the Face of Challenges

‘Chaotic Good’ in D&D represents doing the right thing, even if it means bending the rules. In startup culture, this means navigating ethical dilemmas with agility and integrity. When resources are scarce, and the pressure is high, making decisions that are both ethical and beneficial for your startup can feel like a rogue making a tough call in a high-stakes heist. It’s about maintaining your moral compass, even when the path forward is as murky as a fog-filled forest.

Assembling Your Party: Building a Team of Diverse Heroes

Just like in D&D, a startup needs a well-rounded team to succeed. Imagine assembling a party for your epic quest — you need a mix of skills, personalities, and talents. From the visionary ‘Wizard’ with powers and an academic focus, to the ‘Fighter’ who tackles operational challenges head-on, and the ‘Bard’ who weaves stories to charm investors and customers, building a diverse and complementary team is crucial. It’s about recognizing that each member, like a character in a campaign, brings their own unique strengths to the table. Conversely, each member has a way in which they recharge and continue to contribute. Some need short rests, and some need to unplug to do their best thinking.

Leveling Up: Embracing Challenges for Growth

In D&D, characters grow stronger with each challenge as they gain experience points and literally level up gaining new skills, spells, and abilities. In the startup world, each obstacle is an opportunity to level up. Facing a funding drought? It’s like a party running low on resources while exploring a dungeon. You learn to be resourceful, to pivot, and to find new paths. This resilience and adaptability are what transform startups from fledgling ventures into market leaders. Each challenge faced is a step closer to your ultimate goal, much like a D&D character’s journey to higher levels. Framing these interim challenges as leveling up opportunities is a much more fun way to keep morale up.

The Dragon’s Hoard: Cultivating a Culture of Recognition and Reward

In D&D, sharing loot strengthens bonds and morale. In a startup, recognizing and rewarding contributions is vital for team spirit. Implementing a culture of appreciation — be it with equity, acknowledgments, or team celebrations — is akin to distributing treasure after a successful quest. It fosters a sense of belonging and loyalty, crucial for a startup’s journey, but also ensures that as you’re keeping watch night and day, you’re reminded that you’re all sharing the risks and rewards.

The Final Boss: Tackling Big Challenges with Strategy and Teamwork

Facing the ‘Big Bad Evil Guy’ in D&D is a test of strategy, skill, and teamwork. In the startup world, this is akin to major challenges like securing a crucial funding round or landing a key client. It requires a unified front, strategic thinking, and unwavering resolve. It can take weeks to months to years of planning and preparation, and sometimes be privy to luck and chance.

Think of it as rallying your party for the final showdown, where every member’s contribution is critical for victory. You need to do what you can to plan the tactics and strategy, but at the same time, the natural elements and inherit stochasticity will also play a role, being mindful of what you’re up against will be key once it comes time to actually roll for initiative.

My favorite travel uniform. This photo was taken in 2021 when I first proudly made peace with my D&D nerdiness in public

Harnessing Your Inner Nerd for Startup Success

The lessons from D&D are a parallel for a startup journey. Whether it’s making bold moves, innovating with flair, navigating ethical dilemmas, building dynamic teams, overcoming challenges, or celebrating successes, these principles from the fantasy realm are profoundly applicable in the startup universe, especially when the prize is something that can change the world for all of us. So, unabashedly embrace your inner nerd and lead your startup to victory, armed with the wisdom of wizards and the courage of warriors.

Onward to success, brave startup heroes!

This article is dedicated to every leader who’s ever thought, “This meeting could really use a round of initiative rolls.”

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Liz Dennett, PhD

Growing up I wanted to be the Pink Power Ranger, these days I'm CEO of Endolith where we harness microbes to fuel the energy transition