Ben Milne

on brand development, fostering creativity & leaving a net positive impact


Ben Milne is a little bit of everywhere.

As the founder of Dwolla, the revolutionary payment platform, Ben now splits his time between offices in San Francisco and Des Moines. Their offices are quintessential startup equipped with large windows, ping pong table, foosball, ice cream and espresso makers as well as a few fridges filled with beers. There aren't any cubicles to be found, and everyone is family.

I've known Ben for a few years now, so it was great to catch-up and hear some of his story.


Where did the name Dwolla come from?

The name itself is just the words ‘Web’ and ‘dollar’ slammed together. Pretty incorrectly actually. The reality is I had a pitch meeting the next morning and I didn't have a name, so I bought a six-pack and wandered around, came up with the name and wrote it down. It stuck and we never changed it.

As a new financial solution, what steps do you take to build trust with your customer?

Trust is one of those things that as soon as you have to say to someone “you can trust me,” you've already lost their trust. In our case, our perception has always been that we've never had a big brand name to piggyback on, so we just had to not screw up with the customers we earned up to that point.

Don't lie to people. Don’t abuse their information and basically do things the way you would want other people to do them. When we got started there were a lot of things we didn't know and looking back on it, it's amazing how foolish I feel for the way we structured things initially.

At the end of the day the more good you do for more people, the more people will trust you.

If someone hands you a hundred bucks, don't steal it. That's pretty much our job. We need to do that really well and everything else, we just need to get out of the way.

Financial institutions that were behaving poorly gave all financial institutions a bad reputation. The perception is that all financial institutions don't take care of their customers, or they're looking for every opportunity to pull the wool over their customer’s eyes. In actuality, most institutions don't work like that. They just do good work for a lot of people. There is a new heightened level of distrust, especially around all that was going around Wall Street the past couple of years, but if you don't do anything to lose trust in people, then they'll continue to trust you. We had trust at the beginning and we've never lost it. We just have to do what we say we’re going to do.

Ben Milne of Dwolla in his Des Moines Office

You all have been doing videos that seem to be resonating on Twitter. What does that creative process look like?

I'm not really part of it. If we are talking about payment systems, I can be that creative process. Garret (our video guy) has really good taste, and our job is not to tell him how to share what he produces. He just needs autonomy to tell the story, and that whole relationship was built around Garret having an idea.

I think one of the worst things for an artist is when they have an editor.

Then he comes back with the videos when he finishes them. We don't look at them until he drops them off. We may have a little feedback around maybe some of our logo in the next video or something like that.

When you normally think of financial institutions, there are few that you'd want to be associated with. Dwolla seems to be a brand that people want to be associated with.

Yeah. It's not too common that you want to be going around rocking a Bank of America t-shirt. Our branding wasn't really intentional. The people you're around and work with end up marinating your life, and at the time I met creatives like Garett, Anna, Van, Eight Seven Central and Phillip. We wanted to do something that was different. I think the first time we printed shirts we did a run of 50. Since then we've printed thousands through them. If everyone is going right, why would you be afraid to go left? It's much easier to stick out as long as you're not being disrespectful about the way you do it. Just because something is being done one specific way, doesn't mean you have to do it that way.

I don't know if it's taste because some people might not dig that we've got dead presidents with Dwolla chains on. At the end of the day, there has got to be some kind of creative process because the design at Dwolla is similar since the same creative people are still here. If those people cease to exist, maybe that will change a little bit. To me it's because those people are still here and they've been such a heart beat of the company that it will continue this way.

Who has the final creative say?

Just a few people. If they get really jazzed about something good or bad, it's probably going to change. One is the person who runs product, Brent and the ones who run design, Brandon and Nick and I stay pretty close to a lot of it. There isn't one person who is going to say we are going to do it this way. There is a group of people that are working closely with each other, and we're making good decisions. Ultimately if someone doesn't like something or on the other hand, really falls in love with something, we have enough respect for each other that any one of us could probably help sway any of the others in a different direction.

I mean, the t-shirts have always been my thing. I'm kind of infatuated with it. I'm thinking of one right now that's similar to the Rage Against The Machine's nuns with guns t-shirt, but all their heads would be stamped with dead presidents. I don't know if we'll get to it, but I really want to do that next.

What do you think the purpose of the t-shirts are, other than just liking t-shirts?

I need clothing to wear, honestly. I've been in Iowa for the past three weeks. I brought two backpacks with me. One was full of computers and the other had Christmas presents in it, so I had two shirts and my girlfriend, Jami, was amazing and had a few others for me. Really I kind of live out of those t-shirt boxes a lot of time, so when it's time to wear something new, it's time to get those t-shirts printed.

Dwolla T-shirt

What does your day-to-day look like?

There is the ideal, and there is the reality. Reality most of the time is your kind of putting out fires. Trying to figure out what is the thing that if it doesn't get solved everybody’s life might get better or it might get worse. As the company has grown, we're right about 60 now, there is always something like that going on. Some of it you pass off, some of it you choose not to. In an ideal world my schedule looks like this:

From the time I wake-up until 10 or noon, depending on what time zone I'm in, I'll work on product meetings. After that, I'll take a couple of hours to eat lunch and have creative time. I might read or I might draw or do something that's just a separation. Then the afternoons are based on themes. One day I'll do marketing, product, legal, recurring. It doesn't always pan out, but the distraction is just having life happen, like every other job, but I try my best to put themes throughout the day.

What do you do creatively outside of the financial industry?

There is probably a little interesting trick there for me because a lot of the things I enjoy doing, I'm not good at. I love writing code, but I am a bad engineer. I love creating things with my hands, but I'm not a very good craftsman. I love to draw, but I am not that good. I really like writing, but anyone that has ever read my writing will tell you that everything that I do is completely wrong. I put everything in the wrong place, and I can’t spell. Those are all things I really enjoy doing, but I am not great at them. I think the benefit is that I can at least appreciate a lot of what other people produce even though I'm not as good at it, but I know it makes me happy.

Do you act that way with business ideas as well? I'm sure you have 900 ideas floating around somewhere.

You have to. You're going to be wrong way more than you're right, but once you put your time behind one you're going to need to be right way more than you're wrong. The purpose of business is to earn and keep clientele, to earn and build a customer base, to earn and build the right to earn and build more. If nothing ever works, you can't ever build anything, so if you're not sharing and you're not prepared and you’re not shipping things and you don't get a return that allows you to keep doing it then (it sounds bad) you might as well go live on the street.

It's not all about money, but organizations have to live, they have to eat. Inside this company, I can't even count how many dozens of kids that it supports. My job now is less about trying to ship everything I come up with just because I think it might work, but it is more trying to optimize the things we do put out the door and making sure it has the net return it is supposed to have.

What legacy do you want to leave?

If the people I love can say that me being a part of their life was a net positive for them, that's enough for me. Most things are bullsh*t... good people aren't one of those things and if I've impacted their life in a positive way I've got no regrets.

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