Inno Under 25: Dilene Upendra, Motley Fool Ventures

Editor's note: Each year, DC Inno and the Washington Business Journal spotlight some of the region’s top young innovators under the age of 25, and this year we’re featuring a diverse group of nine disruptors, philanthropists and venture capital enthusiasts determined to shake up the status quo. Click here to read the other profiles.

Dilene Upendra, associate, Motley Fool Ventures

What is your role at Motley Fool? I’m on the investing team at Motley Fool Ventures, a sister company of The Motley Fool. I’m primarily focused on sourcing deals, financial modeling and portfolio company monitoring. That being said, we’re a lean team, so we all wear multiple hats. Our team is currently focused on fundraising on top of regular investment activity.

You started as an intern. How did you get to where you are now? I interned for MFV for two summers while I was finishing up grad school. Both internships were during the pandemic, so the role was fully remote. As soon as I joined the team, I made sure to set up one-on-one coffee chats to start building connections that would normally form around the water cooler. I learned what everyone was working on, and offered to help plug into everything. I asked for book and podcast recommendations. I viewed everything as an opportunity to learn, and worked my butt off to catch up on how VC works, jargon and all. As a result, I was able to work on a live deal throughout the entirety of its life cycle during my first internship. At the end of my first internship, I sent thank you notes to everyone on my team and expressed interest in returning. I kept the connections warm throughout my school semesters, and eventually landed a full-time position as I was finishing up my master’s.

What inspired you to pursue a career in venture capital? I was drawn to venture capital because of the potential to directly uplift my community, both in terms of working toward boosting investment activity in the DMV and working with underrepresented founders who haven’t had the same access to capital as their counterparts.

Were you always entrepreneurial? I’ve always had a business-oriented mind. When I was in elementary school, I really enjoyed craft-making with my mom. One summer, I noticed the other girls in school starting to wear a certain kind of bracelet — one that was overpriced and that my family couldn’t afford. I remembered seeing similar materials during my last Michael’s trip and came up with the idea to make my own jewelry and sell it. Luckily, my school’s mini-market for students to sell products was coming up. I spent that entire time period making bracelets, and sold every single one at the market later that year.

Are you involved with any startups in the DMV? I’ve gotten really involved in the DMV ecosystem in the last few years. I’m a mentor for the Techstars Washington DC Powered by J.P. Morgan Accelerator, which is primarily focused on supporting underrepresented founders, and I’m on the board for VC in D.C., a networking group of over 250 VCs in the D.C. area. Additionally. I’m a member of the D.C. chapter of All Raise, a networking group that connects women founders and funders.

Where do you see yourself in five years? I hope to be a VP at a fund. I’d like to run my own fund one day, but that’s definitely farther than five years down the line. I also see myself being ingrained in the D.C. venture ecosystem even more. D.C. doesn’t get the credit it deserves as a tech hub. 

Favorite book? Picking just one book is so difficult! I’d have to say one of my current favorites is “The Seven Husbands of Evelyn Hugo,” by Taylor Jenkins Reid. 

How do you unwind? Basketball was always my favorite (despite my height). On days when I feel overwhelmed, I find myself on a basketball court shooting hoops by myself.