Answer These Important Questions Before Fundraising

Here are 50 guiding questions that prompt founders to think critically and creatively before taking their first fundraising call

At Rough Draft Ventures we work with hundreds of first-time founders at the earliest stage. We’re often their first supporters, backing them with raw products and an inspiring vision. Our goal is to accelerate them to the next stage — one where they have the traction and infrastructure that deserves additional funding.

Over the past four years, we’ve backed nearly 100 student-founded startups that have raised additional funding from leading seed stage firms including Founder Collective, Box Group, First Round Capital, Slow Ventures, and Lerer Hippeau Ventures.

As first-time-raisers, our founders often turn to us for advice on how to navigate the complicated world of fundraising. Throughout these conversations, we’ve identified a set of questions that encourage our founders to think critically about why they’re fundraising, help them articulate a strong narrative, position their current story within the broader narrative of the company, and illuminate areas of improvement.

Before taking your first fundraising meeting, be sure you have an original and thoughtful answer to these 50 questions.

Source: Giphy

Remember: VCs meet with hundreds of companies, meaning they’ve heard hundreds of answers to these questions. When talking about market size, for example, don’t just list the number of smartphone users or snake people. Make your story memorable!

  1. What moment inspired you to pursue this full time?
  2. Who does what on your team?
  3. How do your backgrounds prepare you for this startup?
  4. Who are your next two hires and why?
  5. Who are your closest mentors?
  6. What’s your favorite book?

7. What problem are you addressing?

8. Is this really that problematic?

9. Who is your target consumer?

10. How big is the market?

11. Let me ask that again. How big is the market really?

12. Can you send me one or two articles to help me better understand this market?

13. Why does this deserve to be a standalone company rather than a feature of an existing product?

14. If you could add two features to your product right now, what would they be?

15. How technically challenging is this product?

16. Is this product easily adoptable?

17. What’s defensible about your product/model?

18. How many customers do you have?

19. How engaged are your users?

20. What are your milestones to date?

21. What has been the highlight of your last month?

22. What has driven your growth to date?

23. What’s one thing you’ve learned from your early customers or pilots?

24. Can you share any testimonials?

25. How do you acquire customers?

26. What’s the sales cycle like?

27. What are your unit economics? Do they improve with scale?

28. What’s the path to profitability?

29. What could go wrong with this approach?

30. Can you walk me through the supply chain? How does this optimize with scale?

31. Who are your closest competitors?

32. What makes you unique among the competition (ie price, product, etc)?

33. Why should a startup, rather than an incumbent tech company, solve this problem?

34. Has anyone tried to solve this? Why hasn’t it worked before, and why will it now?

35. What company do you look up to the most?

36. Are there potential network effects with scale?

37. Does it make sense to focus on large, mainstream audience or a concentrated community of power users? Why?

38. Does this company go public?

39. What would have to happen for you to say “okay, we did it. We did what we set out to do” ?

40. How big does this get beyond that?

41. What regulatory hurdles do you face?

42. Have you filed a patent?

43. What makes this defensible?

44. What’s the biggest regulatory risk?

45. Why are you fundraising now?

46. What does your traction to date prove?

47. What are you fundraising for?

48. What is the timeline for this round?

49. What are one or two companies you look up to?

50. Who are 3 Angels and 5 VCs you’d like to participate?


If you’re a student looking to take your startup, company, or project to the next-level, drop us a line & let’s explore what we can build together.
Icon credits: “Creative Team,” “Market Share,” and “Piggy Bank” by Delwar Hossain, “Gift” by Alberto Oliva Vilches, “Cog” by Eric Bergholz, “Scale” by Edward Boatman, “Analytics” by DesignNex, “Podium” by Miguel C Balandrano, and “Rules” by Arthur Shlain from the Noun Project