The Technology Association of Iowa hosts a “TechBrew AM” networking event each month in communities across Iowa.
The Technology Association of Iowa is celebrating its 20th anniversary and Waller said to celebrate, he wasn’t sure how to approach this interview.
“We really wanted to focus on the future and I think you embody the future of the technology industry in the state of Iowa,” Waller told Milne.
Waller would ask Milne about his childhood, career, future plans and favorite curse word during a 20-minute question and answer session.
The interview has been condensed and posted below. The questions are in bold.
Hometown and high school?
Ben Milne: I went to Cedar Falls High School in Cedar Falls.
Talk about leaving Cedar Falls and take us through your different roles in the tech industry prior to starting Dwolla.
BPM: I liked computers, and apparently computers are the tech industry. I owned a manufacturing company that basically I found customers through the computer and designed products on the computer. I sold that and started working on finance technology and realized what venture capital was. I realized what that was because I didn’t have enough money to pull off what I wanted to do.
Through that I kind of found myself in tech but it was definitely not an intentional path. I’m very grateful for it and for many people in this room and many who aren’t, for helping me understand how this whole thing can work.
What was nine-year-old Ben Milne interested in as a kid?
BPM: Army shit. I’m pretty sure I really liked camo things.
At 9, we had moved out into the country so I spent a lot of time in the woods, I remember losing my dads hatchet which was a big deal. But I was just a normal kid, I ran around a lot outside when my parents told me to get off the computer. That was also around the point in time when we got our first internet connection.
So being a kid in Cedar Falls with an internet connection out in the country, that opened up my world. Which is also where all my money started going, and still does.
Talk about what Dwolla is?
BPM: Dwolla is the ideal API to move money. We connect businesses software to banking infrastructure, so their software can move money.
So why start it?
BPM: I started it initially because in my previous company, we took all of our money in through credit cards which have high fees. And still today, the ATM has charges, when the merchant swipes a card they have to pay a charge. So basically the thesis wasn’t really that magical. It was designed to use the internet to bypass a lot of that older tech and make it less expensive.
A lot of the early technology, myself and another individual named Shane (Neuerburg) worked on it. It took us a couple of years to stand it up and get it running then we figured out we had a legal problem so it took us a couple years to solve that and get it to market. The first product was a consumer product that anybody could download or sign into to send money.
So you started this, and now you are starting to attract investors. Talk about some of those early investors that came in and gave you validation, then talk about the story that you are sitting in Cedar Rapids pitching to Ashton Kutcher where he becomes an investor.
BPM: One of those is way more interesting than the other.
My first outside investor was also my attorney. This guy had my back and at one point I went to him and said this was something I am thinking about doing, do you think that I am going to end up in jail? I’m joking a little of course but he had a background in law and banking. Above all else, I trusted him and appreciated his guidance.
He encouraged me to do it. That was my first outside investor, and I decided to put up as much money as he did. He had some friends who also joined in, so it really was just family and friends who didn’t know if it would work but just gave me a shot. I’m really grateful for those guys. They consequently changed my entire life.
And Ashton, I met him through a friend and to be honest, I didn’t really want to take the call because I didn’t know Ashton, life was weird at that time. We’re in a smelly room in the Midland Building trying to keep our servers online. Then somebody calls and says there’s this person I think you should meet, I didn’t want to take the call because at the time I was just thinking “I got customers to take care of.” The first time I talked to him we talked about PBR as a business, the second time I talked to him, he signed up for the system and it worked. He ended up investing like a number of other people. What always impressed me about Ashton was his product skills. He’s someone I’ve really enjoyed working with over the years albeit in a far different capacity today than back then.
For me if I look back, Dwolla’s success there was a big part of Des Moines success. A lot of investors came in and you had a pull to go to the Bay Area. What was that strategy?
BPM: We had a hard time building a leadership team the first time around. All the bigger businesses had a strong director level, VP level and C-level suite. These are specialized roles and many deal with hyper-complex issues that are difficult to hire for, especially as a startup company.
The first time around I just did not have the aptitude to hire those people here. The investor we ended up working with was largely because of their reputation and experience recruiters as well as their in house team. They did exactly what we moved out there to do with us, which was to build out a leadership team. And successfully so. The business itself changed a lot but this time around we’re making a different bet that we’ve learned a lot and can do it here.
I certainly got an education while I was in the bay area. I’m still getting one.
So talk about this time around, what did you learn?
BPM: We realized that we have world-class technology and started selling it to businesses in a white label environment where they loved our tech, but didn’t want our name on it. That fairly simple nuance changed the business, which meant we were a business-to- business company. We sell our products to companies not to consumers and that wasn’t what all of our investors signed up for in the first business. Anytime you take on investment it’s normally with a thesis, and if that changes, your investors may choose to support you differently.
And as one told me coming out of that change, I’ll support you socially but not financially.
What does Dwolla look like in five years?
BPM: The company is a growth company again. I think we all know that our businesses do need to make money and searching for that gold mind is, for many companies, a completely thankless job. But then when you find it, your job is just to mine. We’re in a mining phase.
Shut up, and do the work. It’s not sexy. Recruit, do the work, earn customers, build a funnel, rinse and repeat. That’s really what we are focused on now. If we stay focused, I don’t know how big and far we can build this business, but I do know that the market is tremendous and we have a lot of hiring to do. So if we hire the right people and do the work well, then it could be really impactful.
Over the last decade you’ve traveled on behalf of Dwolla. Talk about those experiences and conversations from people you’ve met across the world.
BPM: Smart people are everywhere and traveling has certainly given me a good context for there are super smart people here, we don’t need to keep opening offices. We have two and we will focus on those. We should keep recruiting here, keep our head down and do the work. And not be shy about wanting to do it here.
It’s amazing even when I leave how much credibility the business ends up getting for building in Des Moines. I’m the guy from Iowa in almost every room when I leave, which is ok.
What is the state of the Des Moines and Iowa startup ecosystem?
BPM: It’s good and it’s growing but we have work to do. Thank god for Workiva, it was started here and built here. And while I recognize it has other offices, the act of taking a company public from this region has a huge economic impact.
Beyond that, it also has an intellectual and cultural impact, showing it’s possible therefore more people put their money into things. That in itself has been a major pivotal change since I left and came back. But, we still have work to do.
Our connection from Seed to Series D is still disconnected, you can’t do all that here. The investor base we feel certain segments of it, but not all of it end to end. That will get better over time.
Give advice to 18 year-old Ben Milne
BPM: Don’t go to college.
Is that the advice you would give your kids?
BPM: Depending on the kid. I didn’t last long in college, it was a waste of my parents money and it’s not how I learn. Contrary to a lot of people’s experience, I lost six to nine months in college and I wish I had it back.
So depending on the kid, we will see. Given, I am saving for their college and if it’s between MIT and Stanford, I will push them to MIT. But if they decide not to go and want to make art, they can do that.
Star Wars or Star Trek?
BPM: Star Wars for sure
Favorite curse word?
BPM: There’s so many good ones. I can’t pick, I’ll just keep using them.
Favorite caffeinated beverage?
You are out of town, crashing at a friends house or staying at a hotel?
BPM: I’ve never been asked that question.
What is your least favorite word?
BPM: It’s not one word, but “I can’t.” There’s just a hot mess behind that.
Comedy club or dance club?
BPM: Can I pick another one? How about just live music.
What profession would you never want to try?
BPM: I would never want to be a dentist. Their job is so stressful.
If heaven exists, what would you like to hear God say when you arrive?
BPM: This may sound totally stupid depending on what you believe, but when I die I’m not looking for God I’m looking for a good memory. And I hope I see my kids.
Clay & Milk Extra: If Des Moines could do something to help you or Dwolla what would it be?
BPM: Please refer people to us! We’re hiring heavily in our Des Moines office and we’re looking for exceptional people to join the team.