10 Questions to Ask a VC

After serving as the chief operating officer of Great Harvest Bread Co. (and writing a book about his experiences), Tom McMakin spent the last four years learning about the private equity business from the inside.  He had stints as an operating affiliate of McCown DeLeeuw and Shansby and subsequently set out to raise his own fund to pursue a "patient capital" investment thesis.

Recently, Tom shared his list of questions every entrepreneur should ask of a prospective venture capital or private equity firm.  I've added my annotations in italics.

1. How big is your fund?
   There is no point trying to raise $1 million from a $1 billion fund.
2. How much is left in the fund after commitments and reserves for follow-ons are accounted for?
   Is there enough "dry powder" in the fund to support your company's needs over time?
3. When do you intend to go out fundraising?
   In other words, are you going to disappear for six to 12 months immediately after making an investment in my company and joining my board of directors?
4. When you fundraise and tell the story of your three most successful investments, how will you describe how value was created for LPs?
   The answer to this question will give you some insight regarding how you might be expected to create value.  For example, if the firm's biggest success came as a result of increasing valuation multiples through the consolidation of a fragmented industry, your company's strategy of creating value through innovation and organic growth might not be a great fit.
5. Who is on your firm's investment committee?
   Depending on the firm, your primary contact may not be among the small group of founding partners who may be making key investment decisions.
6. What was your firm's advertised IRR when you raised your last fund?
   If the firm raised its most recent fund based on an advertised trackrecord of, say, a 60% internal rate of return, you might want to question whether your plan's forecast of, for instance, a 30% IRR is really going to maintain your investor's interest over time.
7. May I get a copy of the "book" you sent around when you raised this fund?
   What promises did the general partners make to their limited partners when they raised their last fund?  How might those promises impact the fund's relationship with your company?
8. What do you think the exit will be on this investment?  Do you think it will be a financial buyer or a strategic buyer?
   You are going to be asked this question.  It's only appropriate that you find out up front what the expectations of your investors are regarding this critical issue.
9. As you think about how to shape the company so that it is optimally positioned for that exit, what three things do you think need to be done in my company?
   The general partners are measured against their ability to deliver value to their investors.  By what metrics will you be judged?
10. What was your firm's biggest disaster as an investor?  How did the investment go sideways?
    There is a difference between a bad result and a bad investment.  Does the investor know the difference?  How did they behave?