THE TOP 50 HARD QUESTIONS INVESTORS WILL ASK YOU

Are you looking to pitch your startup but don’t know what to expect or how to prepare for when you meet with your potential investor? We’re here to help!

Over the past 7 years, we have met hundreds of startup founders just like you! During their fundraising journey, they have come to Silicon Valley and stayed at Startup Basecamp to find more opportunities, such as meeting with investors and pitching their startups. Taking part in dozens of pitch nights and hearing from hundreds of founders about their investor’s meetings, we noticed that one of their major struggles was being completely prepared for tough questions! Knowing this, we decided to gather all these experiences from our founders and investors network to prepare the ultimate list to help you to prepare. 

So, before you go ahead and pitch your deck, here are the top 50 questions you will be asked:

A: Who you are | Team, Competition

#1 Who are you and who are your team members?

#2 What relevant domain experience does the team have?

#3 What motivates you and your team?

#4 Why won’t a huge corporation build something like this and use their existing customer base and capital to capture market share?

#5 How do you plan to scale the team in the next 12 months?

#6 Who are the company’s competitors, and what gives you a competitive advantage?

#7 What advantages does your competition have over you?

#8 What are your company’s weaknesses?

#9 How big can your company grow?

#10 How are you different from similar companies?

#11 How can you prove that you have a truly unique value proposition? 

#12 How is your company a good fit for a VC fund?

B: What problem you’re solving | Solution, products, and services

#13 What problem are you solving?

#14 Why did you choose this problem to solve?

#15 Why do users care about your product or service?

#16 Why do you think this hasn’t worked in the past?

#17 What are the major product milestones?

#18 What are the key -features of your product or service?

#19 Can you provide a demonstration of the product or service?

#20 Does the Company Have Differentiated Technology?

#21 What traction have you made?

C: Who is benefitted from your solution | Market, Audience. 

#22 How does the company market its products or services?

#23 What is the company’s PR and social media strategy?

#24 What is the cost of customer acquisition?

#25 What is the projected lifetime value of a customer?

D: What the risks are

#26 What do you see are the principal risks to the business?

#27 What legal and/or regulatory risks do you have?

#28 Are there any product liability risks?

#29 What aspect of the business is giving you the most trouble now?

E: What your financial plan is

#30 What are the company’s short term and long term projections?

#31 How much equity and debt has the company raised?

#32 What future equity or debt financing will be necessary?

#33 When will the company get to profitability?

#34 How much burn will occur until the company gets to profitability?

#35 How much is being raised in this round?

#36 Will existing investors participate in the round?

#37 What is the planned use of proceeds from this round?

#38 What milestones will the financing get you to?

#39 Are your financial projections realistic?

#40 When are you going to run out of funding?

#41 How will I make money from investing in your startup?

F: Personal and COVID-situation related questions

#42 Who were you referred by?

#43 Why did you pick us/me to pitch to?

#44 How did you come up with your startup idea?

#45 Who else have you pitched to and who is interested?

#46 What have you learned about yourself during the pandemic?

#47 Were you prepared for an emergency like this?

#48 What would you do differently if you could?

#49 Can you do the job while working from home?

#50 How did the pandemic impacted you and your startup?

*This list is also helpful for investors that want to prepare better for their meetings with startup founders! This information was put together from interviews with expert VCs and articles with speakers and founders, such as: Eric Koester, Founder at Zaarly, David Ehrenberg, Chief Financial Officer at Early Growth Financial Services, Doug Bend, Founder/Small Business and Startup Attorney at Bend Law Group, PC, Ak Kurji, Chairman & CEO at Gennex Group, Matt Wilson, Co-founder at Under30Media, Tim Berry is the founder and chairman of Palo Alto Software Richard D. Harroch, Managing Director and Global Head of M&A at VantagePoint Capital Partners, Larry Kane, corporate partner at the San Francisco office of Orrick, Herrington & Sutcliffe LLP, Glenn Curtis, Vice President of Market Intelligence for Citi, Suresh Rajan, CEO, LCR Capital Partners, Nathan Lustig, entrepreneur and Managing Partner at Magma Partners.

Hopefully, you benefit from this list. Let me know if you do!

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