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Ben Milne, CEO of Dwolla, speaks of Deals, Products and People

"I didn't start this having any idea what I was getting myself into, I really had no idea," Ben Milne, CEO of Dwolla, admitted. Milne is arguably one of Iowa's best known and most successful tech entrepreneurs. "However I got deep enough in and so close to personal bankruptcy that I had no choice but to make it work," Milne explained to Mike Colwell, Director of Entrepreneurial Initiatives for the Greater Des Moines Partnership, as well as long-time friend and mentor to Milne.

Fresh from the successful launch of Dwolla's partnership with BBVA Compass and on the heels of a week where Milne was one of two Greater Des Moines (DSM) founders to garner national TV coverage (Derian Baugh of Men's Style Lab being the other), Milne fielded questions from Colwell before a packed auditorium at the April edition of Startup Stories, a production of Square One DSM, formerly known as the Business Innovation Zone (BIZ).

The hour-long conversation, accented by questions from the 100 business, government and entrepreneurial types in attendance, was an opportunity for Milne to share insights acquired since that first transaction of his pioneer instant funds transfer network in December of 2010 until today when literally millions of dollars in transactions between consumers, businesses, governments and financial institutions take place daily in real time, avoiding the delays inherent in most money transfer systems that Milne notes are built upon forty plus year old technologies.

Key Event Takeaways


"They don't really start as deals, they start as beer," Milne said about the large-scale corporate deals such as BBVA, which began as an informal conversation at South by Southwest four years prior. "Not giving up is really the key to getting deals done," he offered, reflecting that it is essential to establish a clear business case for the client. "It's not what you want from them," he admonished, "it is what they want from you." He noted that when the client is a business or a financial institution they are likely to be looking for increased revenue and that is the need you must address to close the deal.

Emphasizing the importance of credibility and background in the markets in which you intend to sell or raise capital this youthful CEO spoke to the value of having "an old gray hair" sitting next to you in certain situations while arguing that as the company sales team grew, recruiting with an eye to experience and credibility was paramount.

"Dwolla's ecosystem is unique in that we serve consumers, but we also serve large financial institutions and the government," Milne said explaining that the conversations and needs are different and that presented Dwolla with a special learning curve. That curve has taken Milne to places he did not expect to go. "I never thought about futures and commodities when we started, didn't know anything about them," he admitted. Last fall when the CME, a merger of the Chicago Mercantile Exchange and the Chicago Board of Trade stepped forward with $9.7m in funding, it expanded the horizons of Dwolla's enterprise system.

Product Development

Reflecting on a myriad of product iterations, Milne identified several stages, "the first being does it work and not suck?" Beyond that, and very helpful as you head into funding rounds, is the stage "are customers using it?" Explaining that Dwolla has come a long way in its product development methodology, they now work on a strict six-week iteration cycle that is proceeded by a three-day planning session. "It's all about build it, measure it, and iterate," he contended adding that, "if you can't measure it, you should kill it. Some ideas are neat things at two in the morning when you can't sleep, but that doesn't mean they should go to production."


Now a company of more than 70 with offices in Des Moines, San Francisco, Kansas City and New York, "hiring really smart people and letting them do their job" is what Milne considers critical to Dwolla's continued success. Beyond smart, particularly in the early stages of a startup, people must be all-in. "At the early stage, it's the people who really care, the people that will get up at 2 a.m. when something breaks, the people that will sacrifice time with their family," he explained of the harsh realities of what it takes to ensure startup survival in the early stages.

Arguing against the idea that he, like many founders, has held onto too many responsibilities themselves for too long, Milne offers that the only thing at Dwolla that requires his unique skills is speaking for the organization. "There is humility in working on a project long enough to see all of your original work completely depreciated and replaced by better work," he told the audience with a smile while stressing again the importance of people, including in positions you might think you can fulfill yourself.

Admitting that he was initially reluctant to hire a professional recruiter, he credits Jenna Hogan with allowing Dwolla to find and hire smart people. Additionally he gave a nod to Kate Wagner, Executive Assistant to himself, and COO, Charise Flynn, as another hire he felt he could do without and now sees as essential to the businesses success. Of those types of hires he would argue, "Each time you don't hire a person like that, the opportunity costs of what you can't do because they're not there is a high beta."

Of course the right hire requires the right workforce to draw from and Milne's advice for Des Moines on that issue was simple, "The best thing we can do is build great sustainable companies that pay well." Toward that end, Milne and Dwolla are making their contribution.

Greater Des Moines Partnership

The Greater Des Moines Partnership is the economic and community development organization that serves Greater Des Moines (DSM), Iowa. Together with 24 Affiliate Chambers of Commerce, more than 6,500 Regional Business Members and more than 365 Investors, The Partnership drives economic growth with one voice, one mission and as one region. Through innovation, strategic planning and global collaboration, The Partnership grows opportunity, helps create jobs and promotes DSM as the best place to build a business, a career and a future. Learn more at DSMpartnership.com.