We raise growth capital for tech companies, so I spend a lot of time with CEOs trying to choose between Firm A and Firm B as an investor. I wrote an initial post on questions a CEO should be asking directly of a General Partner wanting to invest in the company. In this follow-up I share some questions to be asked when talking with external references.
The most valuable source of discovery is discussions with CEOs where your prospective boss has been an investor / Director. Request a few references. Any reputable investor will have them at the ready. Most will be surprised and disappointed if you do not ask.
Pursue the offered conversations, but also dig around on your own to find references not offered. A LinkedIn or Crunchbase search of current and former portfolio companies will turn up a few former senior executives. You may even find executives who were fired by the investor. Some references will share complaints over issues they brought on themselves, but you can usually filter the feedback and learn from it.
A few good questions for portfolio executives regarding how your prospective investor behaved include:
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