What’s Milwaukee got that Seattle doesn’t? If you are Aaron Gregory, the answer is in-laws. The serial entrepreneur packed up his family of six and headed to Cream City during the pandemic to be closer to his wife, Katherine’s, family, but the well-established pair weren’t ready to give up their careers and connections in the Emerald City.
Fortunately, they never had to.
Both Gregory and his wife continued to work remotely for Seattle startups from their Milwaukee IP address. According to Gregory, the family netted big gains, improving the quality of their lives and the family’s finances — Milwaukee real estate costs are just a fraction of what they are in Seattle — all while staying engaged and connected in their West Coast-based careers.
Then Gregory decided to build a business here, too.
Gregory spent the last six years as general counsel for the money transfer company, Remitly. When the company went public on September 23, 2021, the lawyer with a passion for fintech decided it was time for him to launch his own startup company. Established earlier this year, Upwardli looks to serve some of the same customers who use Remitly: people residing in the United States who are not yet a part of the American banking system.
Founder Gregory calls these clients “newcomers;” they are immigrants, guest workers, students studying abroad, and any other person who finds themselves in need of banking service, but is struggling to secure those services due to lack of information and the absence of a credit history. Users enter basic financial information into Upwardli’s app and then are matched with banking providers willing to serve this, as of now, untapped market.
This pre-seed round company is getting local support from the MKE Tech Hub Coalition. Gregory praised leader Kathy Henrich for getting the business founder settled in Milwaukee, and helping to connect him to investors for Upwardli’s seed funding round. The company plans to conduct a nationwide search for funding, a process Gregory says became easier after video calls largely replaced face-to-face meetings during the pandemic.
“It’s easier than ever to have a (funding) meeting,” he said. “You know, it used to be that you’d go to Sand Hill Road in the Bay Area and have 10 meetings in a row, going from office to office at VC firms in person. Now you can do that same thing in a day from your desk here in Milwaukee and those meetings can be with a firm in New York, and a firm in Georgia, then California. Those physical limitations no longer exist.”
With a passion for fintech that is guided by a dedication to social justice, Gregory is ready to lead Upwardli into a market filled with people who need access to banking to begin living their American dream. In the future, Gregory has plans to expand the service to offer those with credit challenges a pathway back into the traditional banking system. With funding, Upwardli plans to fulfill many dreams, for both their clients and its founder.
To follow Upwardli’s growth, connect with them here.
[…] learn more about Upwardli and serial entrepreneur Gregory, read our December 2021 interview with the CEO. Follow the progress of this Milwaukee-based fintech company […]