Venture Plan Competition Winner Ostrich Looks to Gamify the Personal Finance Industry

Ostrich, founded by William Glass ’14 and Andrew Holliday ’13, leverages social networks and gamification to teach users good money habits.

By Laura J. Cole ’04 ’08MLS

Ostrich—a financial literacy app that leverages community and gamification to help users reach personal-finance goals—plans to leverage its 2022 win at the annual Crummer Venture Plan Competition to expand its offerings, refine its product, forge new partnerships, and gain more investors.

As the first-place winners, Ostrich received $50,000 in cash prize money, as part of a total prize pack of in-kind services valued at well over $100,000. They also have the opportunity to qualify for $25,000 in a convertible note on successful completion and due diligence. The competition’s main sponsor in this year was the Orange County Government, who are making a commitment to supporting small-business and entrepreneurs in the Central Florida area.

Based in New York, the company was founded in 2019 by Rollins alumni William Glass ’14 and Andrew Holliday ’13 to help fill the gap in financial literacy that they feel is lacking in the education system, so people can start improving their finances and live happy and productive lives. Their app, which went live on iOS in late February and will soon launch for Android, is built around the successful model of fitness and weight-loss industry apps, which combine social accountability and community with approachable goals to help users figure out how to do everything from saving for retirement to buying a house for the first time.

“We use the best of behavioral economics to actually encourage people to take action,” Glass said. “It’s just like when we think about regular literacy. You don’t start with The Odyssey, right? You start with Dr. Seuss. I think part of the challenge is that everyone thinks that you have to know everything before you can start making progress, but our approach is simplifying so you can start where you are.”

For Glass, the company’s mission is personal.

“The genesis for Ostrich came from my own experiences as a kid,” he said. “My parents got divorced because of money. They couldn’t agree on financial goals. Ultimately, the stress was too much and our family fell apart. To this day, they’re still kind of picking up the pieces.”

He doesn’t want other families to experience the same fate as a result of not having learned something as simple as how to budget, save, and establish an emergency fund. For Glass, doing so has garnered him the freedom to control his own destiny and to learn how to separate his intrinsic worth from his net worth.

Both are lessons he learned and prepared for while working in corporate America. While selling software, he saw how much money he made the company and knew he would rather put his energy into making money for himself and gaining financial independence. But when he financially reached the point where he could do that and focus full-time on Ostrich, he had to learn to stop relying on the stability that comes from having a consistent paycheck deposited directly into a bank account twice a month.

“But that’s what having a strong financial foundation allows you to do,” Glass said. “If I had been crushed under credit card debt or something else, I wouldn’t have been able to quit my job and start Ostrich.”

It’s the small decisions he made over the years that allowed him to reach this point. As with setting yourself up for financial success, Glass wants everyone to know that Ostrich’s success—even winning this year’s Venture Plan Competition—isn’t something that just happened overnight.

In fact, the company was the in the running for last year’s Venture Plan Competition but only advanced to the semi-finals. The team used that opportunity to continue to build. During the year between, they worked to refine their message and find other companies to partner with, including AARP and Rollins, which will be launching a financial wellness challenge for the campus community in April.

“I feel like so often we only see the highlight reel of successes and wins, but there are often losses,” Glass said. “What people won’t see are the three years of work that went into getting where we are. Three years of not paying ourselves. All the bootstrapping and risks and failures that have allowed us to learn and get better. It’s the same thing when you’re trying to build better money habits. Putting in the time to create a strong financial foundation allows you to better navigate setbacks and bounce back faster.”

Ostrich was one of more than 50 startups who competed in this year’s Venture Plan Competition, which marked the eighth year of the premier plan and pitch competition for regional startup companies seeking exposure and funding. The Kinnect Company, which provides a central, secure database to share information about estate management with those who matter most, won 2nd place and $25,000. And Connectthedocks, the AirBNB of private dock rentals, took 3rd place and received $10,000.

“The Central Florida entrepreneurship community is more energetic and dynamic than ever. Each of the finalists of the 2022 Venture Plan Competition epitomize that with their tremendous growth potential, and we are excited to see how they can use this competition as a springboard to becoming another Venture Plan success story,” said Dr. Pete McAlindon, Executive Director of the Center for Advanced Entrepreneurship at the Crummer Graduate School of Business.”