Kickstarter’s co-founder Yancey Strickler on how to build a more generous world

Yancey Strickler never intended to go into business. The ruminative idealist wanted to be a writer—a dream he chased for 10 years in New York City. Then Kickstarter happened.

In 2009, Strickler, Perry Chen, and Charles Adler launched the online platform that would change the way creative projects and startups were funded. Kickstarter helped pioneer the concept of crowdfunding, a way of raising money online. The Brooklyn-based company raised over $4.6 billion from more than 17 million people during its first 10 years, and successfully backed over 170,000 projects. 

From the beginning, Kickstarter stayed true to its values of elevating creatives from the bottom-up. The company publicly declared that it would never go public. In 2015, Kickstarter became a Public Benefit Corporation, explicitly stating that it would hold itself to higher standards for its conduct and impact. Kickstarter is legally obligated to balance shareholder interests with generating a positive benefit for society. 

After 12 years of working on Kickstarter in many different roles—most recently as CEO—Strickler stepped down in 2017. The time felt right to try something else, like return to his first love.

Kickstarter provided a unique window into how ideas work. At first, no one understood the idea of this new thing called crowdfunding. Strickler and his co-founders learned how to describe the idea in a way people understand and get excited about.

As Strickler pointed out, the Beatles were turned down by nearly every record label they auditioned for. George Lucas couldn’t get funding for Star Wars. The list goes on. Good ideas often go unrecognized by the judgement system in place to evaluate them. Maybe it was worth considering that our judgement system is outdated.

“The status quo view of what’s possible was too limited,” Strickler writes in his new book, This Could Be Our Future. “It often is.”

The status quo persists because people continue to subscribe to these ideas. Or they’re so entrenched in our line of thinking, we don’t even acknowledge them as ideas anymore.  

With this social construction in mind, This Could Be Our Future describes itself as “a manifesto for a more generous world.” Strickler examines the ways our value system has oversimplified to money obsession. Through studying trends ranging from the consolidation of media to the death of mom-and-pop retail to growing wealth disparity, Strickler shows how this economy falls short.

Strickler argues that the West is trapped by three assumptions: that the point of life is to prioritize your self-interest and wealth; that it’s each of us against the world; and that this system is deeply embedded into individuals, institutions, and society at large. 

We need a new system, Strickler argues, calling for a paradigm shift that broadens our best interests from simply present day self-interest to a more holistic view that includes the world around us. To do this, Strickler created a decision-making framework. He calls it Bentoism. Based on the Japanese food box, which separates foods into compartments, Bentoism presents four quadrants people should consider for any given situation. The quadrants are present-day self interest (Now Me), how we engage with those around us (Now Us), the person you want to be in the future (Future Me), and the world you want to see in the future (Future Us). This methodology can help guide us toward a value system that balances security, pleasure, autonomy, knowledge, and purpose.

Dropbox caught up with Strickler to ask about how he developed Bentoism, the relationship between values and time, and what we can all do to rectify conflicting values swirling in our heads.

This Could be Our Future calls for a paradigm shift in values for both businesses and individuals. When did you cultivate this mindset?

I've always had this same instinct. I'm a child of punk rock and indie rock, like Nirvana. Don't sell out. Meaning is about doing it forever. It's about playing an all ages show for five bucks, and the joys of doing that. It's not like going home to your pool afterwards. Those are things that are just facts to me. 

When I started working in business and having management jobs, I initially felt really guilty about it because I was a writer, I was a music person. I'm a creative person. What does it mean for me to succeed in a corporate context? Am I a class traitor for being good in this eight person meeting? It's a funny feeling of I didn't intend this, but I have an aptitude for this.

I found the business world interesting, so I embraced it even though I felt alienated from it. And then I brought the indie rock version of myself to the business world. I had this amazing experience of being a part of creating Kickstarter, something that succeeded on its own terms that lines up directly with these same sort of values that I believe in.

I wasn’t even explicitly thinking about bringing my values to life when I started writing this book. It's only now when I look back that I can see a narrative here. Throughout my career, I was just doing what felt natural, what's been interesting, and responding to opportunities that appeared. It's resulted in a lot of my career being in a flow state of just being able to do things that feel natural. What a gift that is when we have those moments.

You write about the social construction of reality. With that in mind, I was struck by your decision to use the Bento framework for decision-making. Can you explain why you chose this compartmentalized framework, versus one that looks at issues more holistically?

The decision to use the Bento was very organic. I was writing a book that argues that what's rationally valuable is bigger than we think. Rather than convince someone for moral reasons, I wanted to convince someone that it produces the outcomes that we know are important.

Before I was going to begin the second half of the book, which was going to be the solution, I still didn't have the metaphor that I was going to use. I did a lot of reading and drawing. I tried to storyboard the book, drawing the basic pictures of the story and just trying to approach it in different ways just to see what came out. I genuinely had this moment that I write about in the book of seeing that these lines [of time and self-interest] extended.

Suddenly I realized, "Oh, I could draw quadrants there." After that, I wanted to describe the picture I had drawn and I thought, "What is this picture of?" I wrote “beyond near term orientation” and I suddenly realized that was an acronym for “Bento.”

A week earlier my wife showed me a book she was reading about Ikigai, the Japanese idea of life purpose. There was a section about the Bento and about the idea of hara hachi, of [eating only until you are] 80% full. When I was drawing a week later, I had this strange moment of realizing, "Oh, this is a Bento and this is this structure that I can use."

The fact that my solution is sort of bastardizing the classic "two by two” business structure and using it to argue that the assumptions of business are wrong, feels kind of perfect and was unintentional.

How would you explain the Bento to someone in a corporate leadership role?

I think of the Bento for a company as a compass. If you really define what you're about in each of those spaces, that can be so helpful with decision-making. It's a way that every executive can operate from a similar playbook, but the whole company can be empowered to know what a good decision or a right decision is, to know what the goals are. 

For a company, I think the Future Me voice is about their values. The Now Us voice is about what is it they're really offering to their customers. What do people depend on them for? What is that promise? Everyone's Now Me is the same. Every company is trying to grow. Every company is trying to succeed. But what creates real success? What creates meaning? What creates lasting success is by combining the desires for survival with a product that matters to other human beings with a set of values, a story that has meaning. And through that you create an institution. You create something that matters.

So I would say, you probably have your operations of your company on lock, but knowing where it's supposed to go, creating meaning for it, making decisions always in line with what's important to you, that's the hard stuff. And the Bento is a compass that'll let you do that. And this is also a way that we can assess your operations. Are you actually creating value for the future? Are you actually living up to your ideals in a meaningful way? What are you actually doing? Let's map out all your operations and let's see where they live and are you doing anything that isn't about just you?

Or maybe a company discovers there is one thing they do that's not Now Me focused. It's this weird success and they think, “Yeah, maybe we should learn from that and build on that." So the Bento is a way to assess and see where you are now. And then it's a way to make decisions moving forward that are self-coherent, the idea of acting in integrity with yourself. That's what a real flow state is, when everything you're doing is just naturally extending from who you are and that's possible in a corporate context, too. And that's when these institutions  are at their best.

You give examples in the book when you ask the Bento a question, and the boxes give conflicting answers. Is self-coherence what helps guide decision making when this happens?

I came up with the phrase “self-coherence” after writing the book while doing workshops. When I ask my Bento these questions, I will get a variety of answers. And a right answer is generally not just picking one. The right answer is there's some fifth option that's a synthesis. One thing I often find is, the answer might be like your Future Me and your Future Us and all those things say, "Yes, you should do this,” but your Now Me says no. So, then the answer is actually, "Yes, but not yet." And then the question becomes, "Okay, well when?" Then you can hone in and say, Okay, for your Now Me, "what do I need to be satisfied to say that I can do this?" For me it's allowed me to be more specific in those kinds of ways.

Recently in a workshop, I had someone volunteer to build their Bento with me. A woman who runs a creative agency wondered if her agency should work with big corporate clients that pay the bills or if they should work with little startups that are most meaningful to them. We asked the Bento. Her Now Me, which was concerned with survival, said “work with the big companies.” But her Future Me was about working with the small companies because her Future Me wanted to be virtuous. But the most interesting thing in her Bento is that when we discussed her Now Us values, I asked, "What's at the heart of your friendships, your relationships?" Her answer was that she's the truth teller. She's the friend that tells you what you need to know and will do it with love. She's not afraid to confront and say what's real. So the answer to her question for the Bento ended up being, "You need to bring your Now Us self, that truth teller self, into your pitches. You should pitch big companies, but you should pitch them in the way that's true to your values. And you should be the truth teller, but the right answer, the self-coherent answer for your organization, is to be true to that and use it still to maximize impact.”

The answer wasn't just one of those options. It was, how do you bring yourself together? We're so used to the paradigm that we make a choice as a consumer that's bad for us as a person, or make a choice for work that's bad for our family, or we make a choice in our eating that's bad for our health. We compartmentalize all these different parts of ourselves, try to act like they don't impact each other, and we're constantly self-compromising. The goal to me is about not having to do that. The goal is living in coherence.

And that doesn't mean you always get to do what you want, or you always get what you want, but can you consciously act in a way that you know you're being true to you while also being real about the situation at hand. To me, that's the flow state. We know what it is to have a flow state creatively. We know going to see music or having a great time or something, being in that flow. But learning how to be in a flow state on a Tuesday and knowing what that is, is a different story. That’s the ultimate potential with this. I still have plenty of struggles, but it's something that I've repeatedly been able to turn to and reset, to get clarity.

The beauty of the form is that it's an easy and repeatable way to ask yourself those questions, to force that kind of awareness. Because all these voices are alive in each of us. We are listening to them all the time, but they're disorganized. They're discordant. It's hard to make sense of. The Bento is a very simple tool that gives you a little bit more of a handle on what's going on inside yourself.

The Bento framework is constructed around the concept of time. You weigh present values against future ones. Why did you choose time as the variable?

As a progressive optimist, I am inclined to think about the future because I'm projecting that the future is better in some way. For someone who's more conservative, their relationship to time is more looking at the past in terms of why can't we go back to that. I really wanted the book to be practical. And to be practical, there needs to be a plan. You can't have a plan without a timeline. Because if I wrote this book and was just like, "Okay now, let's just all go do it tomorrow," nothing would happen.

I think of time as a friend. It creates possibility. A lot of signals are pointing in the right direction and time can reveal them.

Along those lines, you talk about how change often happens generationally. Are there steps the workforce generations can take to help shift and expand our values?

There's been a lot of work that's happened in the last 10 years to shift the values perspective in business. Kickstarter has been an example of that. We represent the older version of this younger generation shifting things. It’s happening. When I speak at schools and universities, I try to make the case to the next generation, "Hey, don't just take the financial maximizing job at the big company where you're just helping them squeeze their market more. Instead, get on this train of defining new values. It's like the new moral railroad that will allow every generation after us to make better choices." 

We can be honest about the fact that it's difficult to sacrifice, to think about the long term. It's easier to do these other things. Rather than say this is how it has to be, we can ask ourselves how we can provide tools to make it less difficult to make those kinds of choices. I don't think we can say it's easy, but can we make it less difficult?

The people working on this problem over the next several decades are really laying the foundation that every generation afterwards will be building on. And that opens up significant possibilities. So, that's their role in the relay. I feel quite confident that's going to happen.

What is the role of leadership in making this change? When Milton Friedman wrote his Op-Ed in the New York Times, it resonated with leadership. It was in their best interests. Do you have tools that leaders today can implement to help with the shift? 

The two structures that are meaningful are the PBC structure for a corporate classification of dual financial, nonfinancial purpose. The Bento is another structure that's intended to be a helpful tool like that.

I write in the book about how there was this opportunity for Milton Friedman, brilliant person, to define social responsibility. He scoffed at it. So can we get some of our great economic minds who are around us today to think about that? Those calls coming from inside the house are far preferable. I think that the Business Roundtable's announcement about companies benefiting all stakeholders earlier this year, they recognize that if they don't self-regulate, that external regulation will come to change what capitalism has turned into.

So this type of thinking exists. I hope that as an ex-CEO—as someone that doesn’t come from this world but I've been in that world and have great respect for the work in it—that I can be a good ambassador. I hope I can be listened to and be seen as nonpolitical, as someone trying to figure these things out.