If Your Potential Investor Can’t Take the Tough Questions, Then Walk Away

What should you set as your priorities for raising a larger round and what should you seek and demand from your VCs?

This post about Zach Sims of Code Academy inspired me to think about what I’ve learned over the years about the process. In this case, Zach had a great deal of interest in the round, so he could make demands and ask the tough questions, but can you when you are just trying to prove your model or technology could be a success?

The real question you need to ask though, is can you afford not too. We all believe, that we can make it happen if we just get the cash, but the fact is that being willing to aggressively question and check on the folks that seem willing, can be the best thing you can do.

  1. It proves you are serious about your success. If you aren’t willing to treat your VC as a potential partner and understand their value beyond money, then why bother? You think you know everything you need to know for success, but usually, what you think is going to work will not and you will need a partner that is going to help you get through the bad times and the re-evalution of your strategy. Do you want a partner that wants you to feed them bullshit and praise or do you want a partner that will appreciate your good business sense. This isn’t to say that you have to be a jerk or be cocky during the process, but you do need to be willing to ask what is important to the success of the business which is your common motivation. 
  2. Are you going to find out now that your partner is good or bad or are you going to hope they are positive and then find out later they suck.
  3. What kind of partner wouldn’t want you to ask the tough questions? The kind of person that thinks they are above being grilled about their value should never be the kind of person with whom you want to partner. They should walk away if you don’t have the sense to ask them in a respectful tone the questions that are important to your success.

There are a lot of great ideas in this post. Be sure to read through and learn a great deal about how to position yourself.

Zach Sims of Codecademy on lessons in raising $12.5 million for the first time.

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