51 Questions to Ask a Venture Capitalist

So you want to start a business. You have a great idea and you are ready to take the entrepreneurial plunge. But first, you need funding. One way to get funding is through venture capitalists (VCs).

But before you approach a VC, it’s important to do your homework. You need a solid business plan and you need to know your industry inside and out. And, just as important, you need to know what questions to ask VCs.

51 Questions to ask a venture capitalist:

  1. What does your ideal portfolio company look like?
  2. How much time do you spend with portfolio companies?
  3. What kind of businesses do you typically invest in?
  4. Do you have any industry preferences?
  5. Geographically, where do you prefer to invest?
  6. At what stage of development would you like to invest?
  7. How much money do you usually invest?
  8. What added value do you create beyond the capital?
  9. What does your investment process look like?
  10. What is your investment timeline?
  11. What is your investment philosophy?
  12. How quickly do you make investment decisions?
  13. Do you invest jointly with other companies?
  14. Do you prefer primary or secondary investments?
  15. What is your process for due diligence?
  16. How do you structure your investments?
  17. What are your thoughts on convertible bonds?
  18. How involved do you want to be in the companies you invest in?
  19. How many board seats do you typically take?
  20. How long does it usually take from the first pitch to the investment?
  21. What are some of the biggest challenges you have faced when investing in startups?
  22. What do you look for when considering investing in a start-up?
  23. What are some of the most successful investments you made?
  24. Have you ever invested in a company in my industry?
  25. What do you think are the main risks and challenges associated with my industry/business?
  26. Do you have any reservations about investing in my company?
  27. Do you have any suggestions on how I can mitigate these risks?
  28. How do you think my company will be valued in 3-5 years?
  29. What kind of exit do you envision for my company?
  30. When do you think we will be ready to raise our next round of financing?
  31. What are the biggest mistakes you have seen companies make?
  32. How do you add value to the companies you invest in?
  33. What are the red flags that make you hesitate to invest in a company?
  34. Can you give me an example where you passed on an opportunity? And why?
  35. How do you feel about risk in investing?
  36. What are the most common misconceptions about venture capitalists?
  37. How can I make my pitch stand out from others you have heard?
  38. Why did you decide to become a venture capitalist?
  39. How did you get into venture capital?
  40. What is your background and experience?
  41. Do you have any sector-specific expertise or knowledge?
  42. Are there any industries or types of businesses that you’re particularly interested in right now? And why?
  43. Do you know of other companies that are direct or indirect competitors of mine?
  44. How do you think my company compares to them?
  45. Can you introduce me to potential customers or partners?
  46. Do you have co-investors with whom you work regularly?
  47. Have you ever guided a company through a liquidity event? If so, how did it turn out?
  48. Have you ever taken a company through a major restructuring? If yes, how did it turn out?
  49. What do you think is the most important thing a startup CEO should focus on?
  50. Have you ever had a portfolio company go through something similar to what I’m experiencing now? If so, how did they overcome it?
  51. Do you have any advice for first-time entrepreneurs seeking VC funding?

Frequently Asked Questions

What challenges do venture capitalists face?

Venture capitalists often face the challenge of making a return on investment within a relatively short period. This can be difficult if the company is still in its early stages and has not yet generated significant revenue. Venture capitalists may also have difficulty assessing the potential success of a company, especially if it is in a new or rapidly changing industry.

How do you evaluate a venture capital firm?

When evaluating a venture capital firm, you must consider its track record and the types of companies they have funded in the past. You also need to consider the amount of money to invest and whether the firm will be able to provide the funding needed to grow your business.

What are the advantages and disadvantages of venture capital?

On one hand, venture capitalists can provide valuable resources such as money, advice, and connections to help young companies grow. On the downside, they can also demand a lot in return, such as a high percentage of the company’s shares and control over key decisions. This can be a risky proposition for young companies, especially if things do not go as planned.


When looking for a venture capitalist funding for your startup company, it is important to ask smart and informed questions. The above questions will help you ensure that the VC firm and investors you approach are right for your business.

Do your homework ahead of time, prepare, and always remember that no question is too small or insignificant. If you are well-informed and armed with the right questions, you are more likely to get the funding you need to make your business dream a reality.

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