Ollen Douglass, Managing Director, Motley Fool Ventures Motley Fool Ventures is an early stage, technology-focused venture fund focused on Series A companies.Ollen Douglass, Managing Director, Motley Fool Ventures
Motley Fool Ventures is an early stage, technology-focused venture fund focused on Series A companies.

Motley Fool Ventures Logo


Prior to joining the Fund, Ollen was CFO of The Motley Fool Holdings, Inc. for 14 years. During that time, he was responsible for the overall financial health of The Fool and helped guide the company through periods of major growth, contraction, and market volatility. Ollen’s oversight duties included The Fool’s finance and accounting groups as well as legal, benefits, sales, business development, real estate, business intelligence, international and asset management. His financing experience spans the full spectrum from bank financing to venture financing. During Ollen’s management of the pilot program, Motley Venture Partners, he and the team compiled a portfolio of private companies that will be contributed to the Fund. Today, Ollen serves on the board of Eyrus, InHerSight, and Young Artists of America. He has been a recipient of the Motley Fool Founders’ award and Favorite Fool award. He was twice nominated for Greater Washington CFO of the Year and is a member of the 2019 class of Greater Washington Minority Business Leaders. Prior to joining The Fool, Ollen worked in mortgage banking, focusing on mortgage servicing, fair lending and risk management. He was also an auditor for KPMG and is a CPA (inactive). Ollen graduated from the University of Baltimore with a bachelor’s degree in accounting and lives in the Washington area with his wife and three sons.

CEOC: What recent success are you most proud of?
OD: I’m most proud of the launch of The Motley Fool’s inaugural venture fund. We made a conscious decision to turn the typical venture capital playbook upside down, and instead of courting large investments from a few institutions, we leveraged The Motley Fool community to raise relatively smaller amounts from a large number of retail investors. Launched in 2018, Motley Fool Ventures went on to raise $150 million from over 800 investors (or “Limited Partners”/”LPs”) in approximately eight months. The fund exceeded its $100M target by 50%, was over 80% larger than the median new fund in 2018, and was raised 40% faster than the average fund. We have LPs in 45 of 50 states and have close to 200 women LPs. Motley Fool Ventures is believed to be the largest debut fund ever that was led by an African American.

CEOC: What’s your motto?
OD: At The Motley Fool, we have six core values. The first five are the same for everyone: collaborative, innovative, fun, honest, and competitive. The last is “Motley,” and each employee is encouraged to choose their own as a way to personalize the core values. Mine is “purpose and profit.” I am energized by seeking to do good and do well, without compromising either.

CEOC: How do you keep your company in front of trends, customer needs, and your competitors?
OD: Motley Fool Ventures is a strong believer in community and interacts with our customers through regular digital communications, surveys, and live events. With a stakeholder approach, we focus on collaboration and building win-win relationships with our customers, employees, business partners, and shareholders. That approach exposes us to a wide spectrum of priorities and perspectives. We believe there is room for many in our space, which diffuses the need to focus on companies as competitors—there can be many winners.

CEOC: Is M&A part of your innovation plan?
OD: As a new and lean organization, Motley Fool Ventures is very open to an objective view on build versus buy decisions. We are more likely to acquire technologies to accelerate growth than to acquire fund assets. One of the many benefits of operating in the startup world is being surrounded by innovation, which makes the difficult seem doable and the “never been done” feel like the next logical step.

Join CEOs like Ollen at the 2020 Convention to discuss this and other pressing topics.