• Heartful Academy

Investing in the best vision for our future

Ollen Douglass is the Managing Director of the 150 million USD venture capital fund, Motley Fool Ventures. That sounds like serious business, right? Now hear this: the mother company, The Motley Fool, started as a prank.


In 1994, the two founders and brothers, David Gardner and Tom Gardner, published a series of messages online promoting a nonexistent sewage-disposal company. The messages were meant as an April Fool’s joke, but garnered widespread attention and ended up in an article in The Wall Street Journal. The company name “Motley Fool” is taken from Shakespeare’s comedy “As You Like It”. It references the one character — the court jester — who could speak the truth to the Duke without having his head chopped off. Clearly a sense of humour existed from day one in this company, in addition to the courage to not hide it.


In 2001, Ollen joined The Motley Fool and was promoted to CFO in 2003. He started his career as an auditor at KPMG for 4 years, followed by 5 years in the banking industry before finding “The Fool.” Over the years, this was a choice he has definitely not regretted!


The Motley Fool has since then become a household name among investors in the US as well as many more countries. The purpose has stayed the same: “Making the world smarter, happier and richer”. Their core service was to help investors pick the right stocks, and from there they have diversified into advice on wealth management, real estate investments, retirement planning, and personal finance products. They are also launching a nonprofit foundation to further promote financial freedom for all.


Today, the company has more than 300 employees, stellar reviews on Glassdoor, as well as several Best Place to Work awards. The culture created in the early days is still unique - and highly appreciated by the team members. The Motley Fool was celebrated in professor Raj Sisodia’s iconic book Firms of Endearment, and is a recognised exemplar of the Conscious Capitalism movement.


With the co-founders wearing jester hats on the front of the About web page, it is clear that The Motley Fool is still a humorous place. But don’t be mistaken, when it comes to a positive impact in the world, they mean business! According to the headline on their website, it is just themselves that they don’t take too seriously. We find this both refreshing and inspiring.


When the time came in 2018 to set up Motley Fool Ventures, Ollen was the natural choice to lead it, and he and his team went on to raise $150 million for their first fund. It is one of a very small number of $100M+ venture funds run by a Black person, and just recently, Motley Fool Ventures was awarded the Deal Team of the Year by the National Chapter of the Association for Corporate Growth.


In addition to the many years as CFO, Ollen had also immersed himself in the startup ecosystem. In fact, this is how we got to know him. When Cosmina worked as co-founder at the Conscious Venture Lab, Ollen Douglass was a highly treasured mentor for the startups in their accelerator program. Always warm, smiling and insightful it was a good day, both for the accelerator team and for the startup founders, when Ollen paid a visit. Not only is Ollen extremely professional and skilled at what he does, he also has his heart in it. He seeks to make investments that have a positive impact for People & Planet, especially when it comes to putting an end to inequities. On Motley Fool Ventures’ website it reads:


"Motley Fool Ventures chose as its North Star the following quote from David Gardner. We use it to guide our investment choices, but it is also a roadmap for constructive change in a larger context.

Make your portfolio reflect your best vision for our future. Always be thinking ahead, be optimistic, think about the world that you want to create. Because sure enough, your dollars and mine, our capital, is helping shape the world. Truly we are shaping the world every day with our financial decisions. And the future matters so very deeply.

— David Gardner, Co-Founder, The Motley Fool"


We are genuinely excited and grateful to have shared this open hearted conversation with Ollen Douglass about how the world of investing can be a beacon of hope and light in a world that is so challenged as it is today.