Questions from VC investors

Rory Eakin -

This week, I gave a talk about CircleUp's journey.  It gave me a chance to look through old files, including around our fundraising processes.  CircleUp has raised five rounds of capital from professional VC firms (so far). I had a habit during each of those fundraises of sending myself a short email after meetings with the questions we received.

I made the notes to help remember the discussion, but also as a learning mechanism for future calls.  These are not the formal diligence questions submitted in writing that we also had to answer.  These questions came real-time, and needed a thoughtful reply in the moment, which we sometimes did, and sometimes did not.  

Looking back at these now, a whole lot of memories came back.  I thought they may be helpful to share for others.

During our seed / initial institutional fundraise

  • What is your vision and strategy to get there?
  • Why now?
  • What traction do you have?
  • Why are you excited about this problem?

During our series A

  • What is your vision and strategy to get there?
  • What are the knobs and dials?
  • How do we measure success?
  • How do we think about running the business?
  • What is on our worry list?
  • What network effects do you think can exist around the data you are collecting?

During later rounds

  • What is your vision and strategy to get there?
  • What are the most important metrics you look at in the business?
  • What are you seeing in XX [a well known successful private company in our space, but not a direct competitor] that you should learn from?
  • What are your blindspots today in running the business?
  • LOTs of questions on Helio (our internally developed technology) - how it works, why we felt the need to build it, product roadmap, barriers to entry

I'm sure the market has changed somewhat over the past few years, but also believe many of these questions are timeless.  Vision and strategy will probably always come up. The questions are intentionally broad and open ended questions, in part to test your ability to narrow to a compelling story succinctly.  

I love the worry list question.  It puts pressure on you to see how honest you will be - every founder has worries, which do you pick and why?   A good reply will build trust and confidence at the same time; a bad reply will create distance.

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