Life and leadership lessons from Dungeons & Dragons


Last year I started playing Dungeons & Dragons for the first time. As a D&D newbie I was nervous. Would I have to wear a costume? I didn’t even know how the game was played.

For those new to Dungeons & Dragons, here’s how it works: a narrator (the dungeon master) reads out to a group of people descriptions of a place or scenario. The group decides what to do, and the narrator unfolds the story based on their decisions. At certain moments players roll dice to determine the outcome of a decision. It’s basically a free-form, collaborative Choose Your Own Adventure story.

At the same time I started playing D&D, I was transitioning into a new job as CEO of Kickstarter. I initially started playing to hang out with the Kickstarter team. Over time the game has become much more. Here are three things I’ve learned playing D&D.

1. Know who you are

Knowing and accepting who you are is the most important thing to do in D&D and life in general.

In D&D this is quite deliberate. When building a character you’re first asked to declare whether you are Lawful, Neutral, or Chaos. My group began by declaring ourselves Neutral, but events soon revealed a darker edge. After a particularly gruesome encounter, it was obvious: we were Chaos.

Accepting our Chaotic nature was a literal game-changer. Rather than debate how to respond to each situation, it was clear how to act. Once we knew who we were, there was often only one real course of action.

2. Know what you want

In our adventure we began hearing rumors of the Master, the root of evil in our world.

One day I made a proposal to the group. We would find the Master. We would pay tribute to him as his subjects. And then we would slay him and become the new Masters ourselves. We all agreed to this audacious plan, and everything about our game immediately changed.

D&D is typically about exploration. You search rooms, open doors, and explore terrain. Once we declared our mission, things took a different shape. We explored, but with a purpose.

We began to see anything that wouldn’t ultimately lead us to the Master as a distraction. We encountered countless corridors and mountains of treasure. We ignored all but those that seemed likely to lead us to the Master.

The impact of our focus was startling. Questions of tactics and strategy continued to arise, but we approached them with an obvious purpose. Once we decided who we were and what we wanted, it was clear what to do.

After much searching, we finally found the Master. We declared allegiance as planned, and soon found ourselves in battle. After a long and difficult fight, we were victorious. We took the Master’s seat.

3. Parlay first, fight second

When we started our quest, we would engage in battle as soon as we encountered an enemy. We won these battles but they were painstaking. We had to fight enemies one at a time. Our characters were weak and inexperienced. The risk of death was real.

Over time we began to take a different approach. We would first try to parlay with the enemies and convince them to help us or surrender. We used appeals, threats, and tricks to get them to lead us to the Master.

Parlaying had much bigger rewards than fighting. By parlaying we could impact an entire group of enemies, not just ones we physically fought. Soon we began every encounter with an attempted parlay. We would fight only if that failed.

Thankfully I don’t have any literal application of this lesson to my life, but it reminds me of how important it is to scale your actions. It’s satisfying to roll up your sleeves and try to fix every problem yourself, but big picture it isn’t sustainable. There’s just too much to do.

Instead, parlay by sharing the challenge with your team. Even if the efforts come up short, the team has gotten more experience, and your performance in the next challenge will be much improved.


I’ve come to see our Dungeons & Dragons quest as more than a battle with monsters and mazes. It’s been a test of character. The obstacles we faced gave our group purpose and helped define who we are.

Who are you? What do you want? These are the questions to answer. We can’t control events, but we control how we respond to them. Who knows? With a little bit of luck, you just might find yourself the new Master.


My D&D game. From left to right: John, Taylor, Luke, Liz & George

I wouldn’t have survived to learn these lessons without my brave compatriots. Thanks to Liz Cook, George Schmalz, Taylor Moore, and John Dimatos for their wits and wit. And thanks to our incredible dungeon master Luke Crane for guiding us on our quest.

I shared a draft of this essay with the group before posting. Liz responded with her perspective. Here’s her take:

Thinking about taking down the master/becoming the new master was both hilarious and undeniably the right move. It was also very risky — and I think that risk played an important role. It made staying on task feel even more crucial. We were aware of our scrappy first or maaaybe second level brigade and that feeling of being ill-prepared propelled us to stay on target…cause we had to. Don’t you think it could’ve felt different in circumstances where we came with higher levels or more powerful spells or just knowing what to expect? I also wonder if we felt brave because we didn’t feel like we had so much to lose yet. We hadn’t leveled up a number of times. Maybe our lack of experience made us less likely to fear what we had to lose. Maybe it was the fact that we weren’t safe peddling around the caves and could die at any time regardless? I don’t think any of this takes away from our glory or bravery and certainly not our determination to reach our goal however.
Some of my all time favorite moments in the game have been the parlay encounters. A big part of why I enjoy them is the human-ness that it brings to our D&D world. Fighting is definitely fun but even when Luke does such an amazing job painting the battle scene, it can still feel very anonymous to me. A parlay invites emotion, spontaneity, and an unpredictability in outcome that just delights me to no end. This holds true in real life as well.

I couldn’t agree more.

Thanks for reading.

Next Story — A Eulogy for George Grove
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A Eulogy for George Grove

George teaching me to fish

George Grove entered this world on June 15, 1917 in Carlisle, Pennsylvania, and left it on December 17, 2015 in Florida. In between he met the love of his life, raised four children and three grandchildren, shared the gift of knowledge with hundreds of students, advocated for the rights of the elderly in various organizations, won numerous awards, was the captain of the football team, became a football coach, was featured in a documentary film, and caught thousands of fish and threw most of them back.

For years George kept a framed picture that reads “A fisherman lives here with the best catch of his life.” George met Betty in Berryville, Virginia in 1941. Betty first saw George when she was working as a switchboard operator for the telephone company. Every afternoon she would stand in the office window and watch people walk from school to the drugstore. She noticed a handsome teacher who always had one and sometimes two girls on his arms. “Who’s that?” she asked her coworker. That was George.

They met not long after. Betty was with friends at the Shenandoah River and slipped on the river bank and was cut. “Is anyone here a Boy Scout?” she called. George walked out of the river, shirtless and gleaming. “I’m a Boy Scout,” he said.

George and Betty were together from that moment on. In the early days George would sit in the pew behind her at church and pull her hair. That October they got married there. Seventy-two years later handsome George sat crying for Betty’s funeral in those same pews. On that day his wallet still contained a black-and-white picture of her in a bathing suit — a blue bathing suit he would tell you, and she looked great in it.

George and Betty raised four children: Dave, Kitty, Margie, and Charlie. Though George and Betty stayed near home, their children traveled around the globe, moved the world forward with their hard work, and actively cared for both George and Betty until their last days. They raised three grandchildren: Anne, Stephen, and myself.

George lived until he was 98. His mind was always sharp. He was independent until only very recently. He was a caretaker of many for as long as he could be. He was still a flirt to his last days.

Who can ask for more of life than this?

I am named after George — Yancey George — and so is my son. Grandpa was a hero to me, and a model for what it is to be a man of integrity.

I remember him playing hand after hand of solitaire in his chair. I remember his hands on my mine as he taught me to fish, first with a bobber, then to cast, and always teaching patience. Once we caught a catfish together. I remember him going for late night swims. I don’t remember what his eyes look like because he smiled so much. His face to me is forever a smile, his mouth open and wide.

I am the man that I am because of him. I proposed to my wife with George there because I wanted her to know that she was marrying the man I am today and the man I will be in old age. We named our son after him because we want him to have George’s warmth, kindness, and sly and flirty nature. I strive to live up to George as my namesake and my son will too.

My brother Stephen and I are the men we are today because of how George raised my mother. My mom loves her Dad very much. He was always an encouraging and comforting presence for her. There are eight key life lessons she learned from him:

  1. Live life well and boldly but always with humility.
  2. Honor your father and mother.
  3. Love the Lord your God.
  4. Always give back and never give up.
  5. Don’t look back with regret but look forward with anticipation.
  6. Be innovative.
  7. It’s okay to throw the fish back in the water. Let them grow old with you.
  8. Love lasts a lifetime.

This gathering near the beautiful Shenandoah River shows just how true that last one is. George you loved so many so much for so long, and we all loved you too. We’ll never stop missing your touch and your laugh, but your spirit will always be with us. We love you and miss you, George.

Next Story — A Better Views
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A Better Views

The new Drake album, Views, was released two weeks ago to reviews ranging from critical to tepid. Most of the reviews were posted within 72 hours of the album’s release. This is culture in 2016 — someone spends years making an album and the internet gives it all of three days to decide that it’s a major disappointment.

The internet is wrong. The Drake album is as good as anything he’s ever done. We just forget what it’s like to hear something new, the way a song evolves from unfamiliarity to something that lifts us when it pours out of open bodega doors.

The internet isn’t entirely to blame. The album is too long and poorly sequenced. Drake put more stock in constructing a “concept album” synced to Toronto’s seasons (the album goes from winter to spring to summer to fall, which is to say it starts way too slow) than in making an album a listener may enjoy.

So let’s fix this. Over the past week I’ve resequenced and edited down Views into something more listenable. It’s called A Better Views. Make an iTunes playlist, reorder in the sequence listed below, and enjoy a spectacular summer album. And Drake, it’s not too late to do the Kanye and make some tweaks!

A Better Views

  1. Childs Play
  2. Pop Style
  3. Feel No Ways
  4. Still Here
  5. Too Good
  6. Weston Road Flows
  7. Grammys
  8. With You
  9. Controlla
  10. Hype
  11. Fire & Desire
  12. One Dance
  13. Redemption
  14. U With Me?
  15. Hotline Bling
Next Story — Resist and Thrive
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Resist and Thrive

Last week I gave this talk at Web Summit in Dublin. It’s a first-draft of thoughts that I felt compelled to share in a room of entrepreneurs and VC’s. I’d love to hear any and all thoughts on this topic. Thx for reading — Y

This is a talk about what happens when a culture is driven by the need for money to make more money.

A simple way to think about this is through real estate. Throughout history it has been advantageous to be a land owner, and today is no different. People make a lot of money buying, developing, and selling land. Even after the crash of 2008, commercial real estate has climbed again.

As investors and developers churn through properties, there’s a significant impact on the communities that actually live and work there. For families and neighborhood businesses, they must significantly increase how much money they make or they have to leave. No matter their importance to their community, they can’t stay if they can’t pay. And few can.

What happens when these businesses leave? New businesses that can maximize how much money they generate move in. And these businesses are, inevitably, chains. Fast food, retail, banks, and others whose operational mantra is based on capital efficiency. Investors make money, franchises notch a new location, and the neighborhood suffers a significant death.

In New York City, many of the businesses that move in are banks. There are more than 1,800 bank branches in New York — 60% more than there were a decade ago.

Map of bank branches in NYC

Not to mention 400 Duane Reades.

What happened to the people that were there before? What happens to those neighborhoods now that their communities are gone forever?

This isn’t unique to New York or cities. In the past 30 years, downtowns everywhere have been hollowed out by strip malls, chains, and real estate development. Local businesses that serve their communities are going extinct.

We act as if this is an inevitability. But is it?

Behind this dynamic is a monoculture of money optimizing for more money. An investment mentality that hollows out our culture. Real estate is just one example. It’s happening across many segments of our society. And in each case, the existing community pays the price for the investor’s upside.

There are different forms of this dynamic.

A New York Times investigation found that just 158 families have provided nearly half the funding for presidential campaigns. What better investment than your own politician?

In music, 80% of the concert industry is owned by Ticketmaster. A diverse universe of record labels is steadily consolidating down. A shocking percentage of Top 40 hits are written by four Scandinavian men.

In Hollywood, it’s sequels, prequels, and risk-averse exploitations of existing IP — now in IMAX and 3D!

In tech, many investors’ first question for entrepreneurs is “what’s your exit strategy?” Big rounds, big burn rates, and big valuations push startups in the same direction. Maximize growth so you can eventually maximize money for yourself and somebody else.

When everyone is optimizing for money, the effects on society are horrific. It produces graphs that are up and to the right for all the wrong reasons.

We can’t assume that this will work itself out. As money maximization continues, all of us — and the poor and disempowered especially — face a bleak future. This model is only interested in supporting those that can afford to buy in.

It feels like we’ve been auto-subscribed to a newsletter that’s sending increasingly depressing emails. How do we get off this ride?

Do we stay opted in? Or do we opt out?

If you stay opted in and play the game, the ultimate best case is you’re one of the few that gets rich. Later you can give some money away to charity. But other than your bank account, little has changed. The existing structure is reinforced.

Do we opt out? Imagining opting out is emotionally satisfying.

“I might delete Facebook today.”

“I’ll go back to my Razr phone.”

“Maybe I’ll try homesteading.”

But to do any of these means becoming a ghost to your community. It’s impractical. Very few of us ever follow through.

Is there a third option? I think so. I don’t have a fully-fledged plan, but I have some thoughts on where we can start.

Number 1: Don’t sell out.

At some point in the past ten years, selling out lost its stigma. I come from the Kurt Cobain/“corporate rock still sucks” school where selling out was the worst thing you could ever do. We should return to that.

Don’t sell out your values, don’t sell out your community, don’t sell out the long term for the short term. Do something because you believe it’s wonderful and beneficial, not to get rich.

And — very important — if you plan to do something on an ongoing basis, ensure its sustainability. This means your work must support your operations and you don’t try to grow beyond that without careful planning. If you do those things you can easily maintain your independence.

Number 2: Be idealistic.

Always act with integrity. Really be clear about the things that drive you. Remember the lessons your parents and grandparents taught you about how to treat people and make sure your business lives up to that.

Don’t sink into the morass of “industry standards.” Don’t succumb to the inertia of the status quo. Don’t stop exploring new ideas. A small number of people can change how society works. It’s happened before and it will happen again.

There are some great examples to look to for inspiration.

Patagonia is a Benefit Corporation that will share proprietary information with competitors if it will help the environment.

REI is a co-op that announced they’re closed on Black Friday and they’re encouraging their employees to “opt-outside” instead.

Basecamp and the Hype Machine are independent software companies that put their products and life experience ahead of creating massive growth curves. Ten years in and they’re independent and going strong.

Another inspiration is Fugazi and their label, Dischord Records. From playing all-ages $5 shows to running an independent label for 30 years, we can recontextualize them as entrepreneurial heroes. Look at that photo — that could be a founding tech team. There’s even an office dog!

What these businesses have in common is that they are clear on their purpose and they follow a strict code in its pursuit. They don’t want to be everything to everybody. They just want to be themselves.

This thinking is very contrary to the current business zeitgeist, which is all about aggression and being big and fast. Everyone wants to be Napoleon. And we all know how that turned out.

Look at the language on that cover: “be paranoid,” “go to war.” Its violence suggests that being ruthless is the only way to survive. We hear this all around us.

When I became the CEO of Kickstarter two years ago, this tone created a crisis for me. I had never approached my work as something to be done aggressively, but with the weight of the new job and those external voices on my shoulders, I suddenly had doubts. Is that who I needed to be as CEO? Everywhere I looked I saw messages of anxiety and fear. I questioned my instincts and who I was as a person.

Then I read Not For Bread Alone. Konosuke Matsushita ran a company in Japan for many years with a clear ethos. His philosophy was to always act creatively and with integrity, to pursue a positive impact on society, and to encourage collaboration among his team. It’s an ethos that’s as right today as it was then. It confirmed that I didn’t have to play the fear game.

Approaching your work with thoughtfulness at the core is challenging. You’re going against the grain. Your tools of measurement are very different from your peers. It’s easy to doubt yourself — I do it all the time.

But in more important ways, it’s so much easier. You’re free to act with conviction. You can say and do what you believe is right. Your principles will still be tested, but you can respond in ways that will make you, your community, and your family proud.

It’s not about conquering the world, it’s about doing the right thing. When done correctly, this creates the ultimate product-market fit.

Community supported agriculture is a great example of this. A farm produces its crop for a community of people who receive the bounty every week. The value created and shared is balanced.

We want Kickstarter to be similarly in sync with society. Earlier this year we became a Public Benefit Corporation. This means we are legally obligated to consider the impact of our decisions on society, not just our shareholders. Though we are still a for-profit company, as a PBC it’s very different from the expectation that for profit companies maximize shareholder value above all. It acknowledges and embraces that you are a part of a larger community.

We don’t expect everyone doing a Kickstarter project to become a Public Benefit Corporation, or to even care. We want artists and creators to be able to create and build for their own reasons. No single mentality is forced on anyone. It’s a polyculture of aspirations and motivations — just as it should be.

Walking around NYC and seeing a bank on every corner is depressing, but the monoculture’s reign is impermanent. As more of us challenge the status quo, change will spark and spread. The hollowness and corruption of the pursuit of profit above all is obvious to even those who practice it. A new approach founded on a diversity of thought and experience can and will thrive.

I don’t know what the exact right steps are to change all of this. This is just me thinking out loud about something that doesn’t get talked about enough. My hope in sharing it is that someone here can build on these ideas, and make them even better. Ultimately this is going to have to be a group effort.

But we want to be very clear on where we at Kickstarter stand on this. Internally we have a Mission & Philosophy handbook that was written by our founder, Perry Chen. Its final page says it all:

Thanks for your time and for listening.

Next Story — What Kickstarter Stands For
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What Kickstarter Stands For

More than 20,000 creative projects were successfully funded on Kickstarter in 2014 — movies, books, albums, sculptures, restaurants, comics, games, hardware, performances, and other works of art and culture. Because of the imagination and enthusiasm of millions of people across the globe, more creative ideas came to life last year on Kickstarter than ever before.


This reality was unthinkable 13 years ago when founder Perry Chen first had the idea for Kickstarter. Since our launch in 2009, that dream of a more open and accessible world for creativity has become more true by the day. We’re living in a new creative golden age where anyone with internet access can bring an idea to life.

Kickstarter has played an important role in this creative renaissance. As a platform, Kickstarter has distributed more than $1 billion to creators to make art, culture, and technology. As a model, it has remade patronage into an accessible, modern, and mainstream way to create and share. The results are staggering — a half a billion dollars to creators in 2014 alone.

We are extreme optimists on the future of creativity. We see more access and opportunity for artists and creators than any time in history — through Kickstarter and similar platforms like Etsy, Soundcloud, and YouTube. More opportunity brings challenges — competition for attention chief among them — but circumstances are far better for creators and fans than what existed before: a world where creativity was limited by access, geography, and the conservatism of big entertainment corporations.


As a founder-controlled company that operates with independence, we have the freedom to chart our own course for Kickstarter. We will continue to do so with enthusiasm and love for creativity at our core.

To the artists, creators, and aspiring creators of the world: Kickstarter was made for you. It was built to bring people together around your creative projects. It’s supported by a team of enthusiastic fellow artists and creators here at Kickstarter who are devoted to helping your ideas come to life.

To the fans, super-fans, and patrons of the world: Kickstarter is powered by you. It was built to bring you together with amazing artists with great ideas. And it’s supported by a team of enthusiastic fellow fans here at Kickstarter who have backed 10,000 projects of our own.

We exist to help people bring their creative projects to life. This is what we’ve always been about and always will be about. Thank you for being a part of it, and happy new year!

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