Photo of Ryan Cummins and Liz Armistead at The Gathering

Work Culture

Q&A with Ryan Cummins of Omaze: How storytelling can transform lives


Published on March 21, 2018

Last month, we traveled to Banff, Canada for The Gathering to talk with marketing leaders from the world’s most-coveted brands.

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We wanted to find out what it takes to create a cult brand, what elevates a brand from “respected” to “iconic”—and how do you stay there?

While we were there, we had a chance to chat with these leaders to get their insights on creativity and collaboration.

Liz Armistead, Head of Brand and Influencer Partnerships at Dropbox, spoke with Ryan Cummins, Co-Founder and Vice Chairman of Omaze, to learn more about this online fundraising platform that supports causes through experiences.

Omaze makes it possible to do anything from drinking tea with Benedict Cumberbatch, to supporting female entrepreneurs in Africa, to living under Stephen Colbert's desk at a taping of the Late Show.

Liz: How important is collaboration to you in your line of work?

Ryan: It's extremely important. We have 85 people in our organization now. That's grown fairly rapidly over the past five years. In 2015, we ran 95 campaigns, these were once-in-a-lifetime experience campaigns. In 2016, we ran 95, in 2017, we ran 198. This year, we're looking to do double that and run nearly 400.

When you're running these campaigns that require content and social media and emailing and messaging and donor awards... When you donate at higher levels, you get physical goods. It's really critical that the entire team's able to collaborate, as well as for just the entertainment of it. We're creating these once-in-a-lifetime experiences, and so it's a lot of creativity and lot of fun ideas that have to come together that really make these exciting and speak to the world at large. It's critical and it's something that we really pride ourselves in.

Photo of Ryan Cummins of Omaze
Ryan Cummins of Omaze

Awesome. What was your favorite campaign you’ve ever done? Oh man, there's so many favorites. It depends what dimension. When we put together these once-in-a-lifetime experiences, it usually is with a talent partner or brand. We'll do anything from the chance to have John Legend perform at your wedding, or play tennis against Serena Williams, or go wine tasting with Jennifer Lawrence, or the chance to be in Star Wars.

And then each one of those talent partners has a charity partner that they're extremely passionate about that they're supporting. It could be anything from After-School All-Stars, which focuses on kids' education, to Mission Continues, which focuses on veterans coming back from abroad who are looking to continue serving and using the skills to help the world, to health, to education, to welfare, whatever it may be. Then lastly, there's the community and the donors that come on.

With every one of those campaigns, when I talk about my favorites, I have a different story for each one of those verticals. We have stories about winners. One winner who won the Lady Gaga Experience got to hangout backstage with Lady Gaga in Costa Rica. I was standing there when he got to tell her that he came out to his family because of her.

You couldn't imagine a more emotional setting than this person actually finally meeting his icon and telling her that she was the reason that he was able to actually continue living an authentic life with his parents. We had a veteran who came back and had PTSD. And he was sitting there with a comedian, and her name's Whitney Cummings... He was saying, "You're one of the primary ways I was able to cope with my depression when I got back."

So you have these experiences where these winners who donated money end up having these incredible stories themselves, above and beyond the experience. Then you see the talent partners almost get emotional and break down when they're meeting them.

Then, of course, the identifiable beneficiaries at these charities who then get to have a more equitable life because of the money raised. There's some incredible stories there, too. They're all my favorite, it just depends on which dimension you're talking about on any given day.

“You have these experiences where these winners who donated money end up having these incredible stories themselves, above and beyond the experience.”—Ryan Cummins
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At Dropbox, we talk a lot about fueling creative energy. What does that mean to you and your work at Omaze?

I think one of the most important things for any organization to scale, is empowering other people to be as creative as possible and just get the heck out of their way. So I think earlier on in my career, creative energy was about a thousand ideas a minute and trying to figure out which one of those you're gonna get out there, and just totally putting on the blinders and running with those.

But that's really nice for a single person. That's really difficult when you're creating an organization or even a movement. So creative energy is trying to figure out not how to tell people what to do, but why you're trying to do something…then giving them the complete reins to be able to go get that done, however they wanna creatively come up with it.

What we do it at Omaze is, we came up with this higher purpose well before we started the company; my co-partner Matt and I, which was to serve world-changers. We said, "Look, our north star is that we're gonna try and serve world-changers. Our mission is that we're going to leverage the power of storytelling and technology to transform lives."

Then we've amassed this team of super energetic, very idealistic, very bright, intelligent people who come to the office every single day with that mission and that higher purpose. Then the creative energy comes from them. It's not even us any more. We just get the heck out of the way.

“Our north star is that we're gonna try and serve world-changers. Our mission is that we're going to leverage the power of storytelling and technology to transform lives.”—Ryan Cummins

That's amazing. What are some examples of Omaze being innovative out in the world?

We're a non-partisan organization, but what we do care about is creating tangible impact in the world. And usually that's been through traditional 501 [c] [3] s across all of those verticals that I've just discussed. Following last year's election in the US, there are obviously a lot of people on both sides that are very passionate right now, just about the state of the world and about what they believe in, and the future world that they wanna see come into existence.

So we just did a campaign recently that was a chance to go wine tasting with Jennifer Lawrence. Here's an incredibly intelligent talent partner who cares very deeply about the world. But for the most part, everyone has known Jennifer Lawrence as someone who's just sort of fun... Incredibly talented actress, but also fun and goofy a little bit. And she likes to sort of play that. She took on ending corruption in politics. It was the first campaign that we ran with an organization called Represent.Us. They're a 501 [c] [4]. She took it on because she cares very deeply about ending corruption in politics.

For me, that's an incredibly innovative approach to the social fabric of America, to dealing with sort of the tension that we're experiencing right now, and to empowering an entire generation of younger Millennials and Gen Z-ers to basically see that here's this iconic actress who's not just talking about what's going on in sort of the social life of the world, but what's going on in all of our lives. I thought that was really innovative.

Could you tell me a little bit about a time when you were most in flow?

When I think about flow, if you've read Chizmensky's flow, and sort of this idea of when your brain gets into that place where if it's a day, a week, a month, a year later, you don't even realize that you've been doing whatever you've been doing 'cause it just felt so good. I think for me, that comes a lot from ritual.

A couple years ago, I started a daily practice... There's this statement I love, "If you win your morning, you win your day." I really practice every single morning waking up, and I do this thing where I spend 10 minutes writing down my wins from the day before, 10 to 20 minutes reading something that's inspirational, and then about 10 minutes just doing short texts of gratitude to people in my community, my closest family members and friends.

What I've found is doing that puts me in a place where then suddenly I can approach the day with a stronger base, with a foundation. I feel as though I am more in flow every single day as a result of feeling connected to my family, my community, and the people that I love the most. I try and do that every single day.

I think for our team, one of the things that I personally started doing in this last year was actually doing a mentorship class, where we sit down once a week and we spend an hour talking about exactly that. It's called Wins, Wisdom, and Gratitude.

We talk about what are the things that we feel we're winning in our life at this moment? What are the inspiring pieces that we can share and read? That's anything from Brene Brown, who has spoken a lot about the power of vulnerability... to different historical athletes who've achieved something amazing, or CEOs who've done something great, or ordinary people that achieved the extraordinary.

Then we wrap that with gratitude. We started this practice where oftentimes we'll select something in our lives that unexpectedly we realize we benefit from because of someone else. Then we'll write a letter of gratitude to that person. That's something that we do once a week.

How has technology influenced your creative process? Sometimes for the better, sometimes for the worst. I think when it's helping the creative process, a lot of it's initially just with ideas. Any of us think about what happened. Most of us have grown up at least in the last 20 years with search being readily available to us.

I can remember when I was in my early pre-teens, and teens where my family had a large encyclopedia. A lot of the creative process then required finding a volume. A and M were the thickest, and you were to open it up. Halfway through looking for something you found something else. Your creative process was a lot more narrow. It was in your head, and then in the things that you could find. But the process of finding things was much more rigorous.

Nowadays, the process of finding ideas is as simple as these phones that we hold in our hand. The creative process begins with just opening yourself up to as much cross (pollination) of as many ideas as possible from as many different areas as possible. I really try and make sure that I'm exposing myself to different magazines, to different demographics, populations, ages; and that I'm staying out of sort of that trap people can get in when their Facebook is just their closest friends, and they're not really getting exposed to any ideas outside of that.

That's sort of a sideways answer to leveraging technology to be exposed to as many ideas as possible, while at the same time making sure that they're not the same ideas; that it's a wide variety of ideas. Then whatever the project may be, finding out what's the tool that's gonna help us. Maybe it's Dropbox, maybe it's collaboration... I've got a text chain going right now with a group of friends that are all doing exercises together. Maybe it's as simple as text.

Whatever it may be, so long as it leaves you with more energy than you had when you started using that technology, I think it's a great thing.

How can people get involved with Omaze?

We're a digital marketplace that offers the chance in once-in-a-lifetime experiences to benefit charity. That means that for as little as $10, anybody can have a chance to win one of those experiences. You know that your money is going toward an incredible cause. Right now, we have some great ones on the site. Like you said, tea with Benedict Cumberbatch.

You could also enter for the chance to win a Tesla—Kimbal Musk, Elon's brother, just launched that one—which is to benefit organic farming, farm-to-table, and changing sort of the process of food in America. We have a handful of those. If you want to go to, check them out. That's the way to get involved.

Learn how Dropbox Business can help keep your marketing team in sync and integrate your workflows to enhance collaboration.