Real Talk: 10 Important Questions For Founders

Dorm Room Fund
Feb 10 · 2 min read

Throughout my time at Dorm Room Fund, I’ve had the opportunity to learn from some of the best venture capitalists in the industry and to observe and conduct countless diligence meetings. As venture capitalists, a large part of our time is spent talking to founders. After many conversations and much experimentation, I’ve created a list of 10 questions that I’ve found to be effective at maximizing time spent with founders. This is important to the team at Dorm Room Fund, because we’re passionate about providing resources to early-stage founders and aspiring venture capitalists. We hope that reflecting on the following questions will help founders more effectively convey the “who, why, and how” of their company while enabling investors to ask better questions, get better answers, and make better investments.

Note: The order of these questions may vary based on the natural flow of conversation with a founder.

Photo by Randy Tarampi on Unsplash

1. What Do You Understand About This Problem That Nobody Else Does?

This question should allow you to identify the founder’s unique insight into the problem they are solving. They don’t need to have experienced the problem first hand, but they need to have an earned secret. A founder who cites third-party research when talking about the market for eldercare has a much different level of insight than a founder that spent three months residing in an assisted living community. Unique insight is valuable because it can allow for sustainable differentiation. This question should also help determine if this founder is the best person to solve this particular problem and if they can succeed where others may have failed before. Without a unique insight, it will be hard to win a market.

Want to read the rest? Check out the full-length article on our new blog.


Written by Justine Humenansky, DRF Investment Partner (SF). Follow her on Twitter and Medium.

These ideas were developed as the result of conversations with or talks given by Phin Barnes, Hayley Barna, Brett Berson, Chauncey Hamilton, Ann Muira-Ko, Gus Warren, and Larsen Jensen. Thanks to Shohini Gupta for additional feedback.

Get more Dorm Room Fund news and updates on Twitter and learn more on our website. Ready to take your startup to the next level? Apply here to be considered for an investment from Dorm Room Fund. Until next time! 🚀

Dorm Room Fund

Written by

Built by students and powered by @FirstRound, we provide our founders with a strong network of investors, access to world-class mentors, and a $20,000 check.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade