Questions Guy Kawasaki Wants to Ask Entrepreneurs

I saw that Guy Kawasaki tweeted about an interview that he did about ghost tweeting. The fact that Guy ghost tweets really bothers some of my friends and it seems to bother Shaq too, who is quoted in this NYT article as saying:

As for the temptation to rely on a team to supply his words, he said: “It’s 140 characters. It’s so few characters. If you need a ghostwriter for that, I feel sorry for you.”

But I don’t care. I really don’t. But I read the article and I came across this interesting section where the interviewer asks Guy what he would ask entrepreneurs. It’s towards the end of the interview, so I will quote it here:

IamPaddy: You have conducted countless interviews and surely get asked all the time ‘What advice would you give to entrepreneurs?’. Instead I want to know if there’s anything you would like to ask the world of entrepreneurs? Anything you are struggling with or can’t wrap your head around?

Guy Kawasaki: This is an excellent question. Here’s a list of things I’d like to ask entrepreneurs:

1. Why do you think venture capitalists will sign non-disclosure agreements?
2. Why do you try to use sixty PowerPoint slides in a one-hour meeting?
3. Do you really believe that venture capitalists can add value to your company?
4. Why do every one of you think your business is “revolutionary”?
5. Why do you believe that the wireframes and prototype that you cobbled together is better architected than Amazon, Oracle, Microsoft, and Apple (pick any big company)?
6. Do you really believe beta sites when they tell you that they “love” your product?
7. How can you create a forecast that shows you will generate more sales in the first five years of operation than any other company in the history of man?
8. Why do you believe you and your co-founders are “proven entrepreneurs” when you’ve never been successful as an entrepreneur?

These questions made me laugh in an obnoxious way. I was thinking to myself, “Oh man. People who do that are so dumb.” And then I realized that I have probably made every mistake on that list (to be honest, I don’t understand question #6 — if you do, please explain it to me). So I finished laughing at how stupid entrepreneurs are and I came up with a list of questions that I would like to ask venture capitalists / investors. Here’s my list:

1. Why don’t you use your website to educate entrepreneurs about how to pitch to your firm? I know that some of you do and I think it’s great, but too many of you have some of the lamest websites I have ever seen and you just assume that somehow an entrepreneur who is busy trying to build a business will somehow magically figure out how you like to be pitched. Why not include a frequently asked questions section that explains why you don’t (can’t) sign an NDA?
2. Why don’t you figure out ways to add value to your portfolio companies that extend beyond giving them money? Again, some of you do, but too many of you don’t. Rather than asking the entrepreneur how she thinks you can add value, why not tell her? Or at least enter into a dialogue about how the partnership would work and the value that could be added.
3. Why do you think that just because a company is in your portfolio, it will be a great strategic partner for the companies that are pitching you? I’m sure there are scenarios where one of your portfolio companies will be the best strategic partner for another portfolio company, but I’m guessing that those would be some long odds.
4. Why do you think every one of your portfolio companies is revolutionary? Maybe the reason entrepreneurs think their businesses are revolutionary is that they have been told that your portfolio is revolutionary when it seems pretty ordinary. If you set the bar low, we’ll step over it.
5. Why do you insist on asking “What stops Google from doing this?” Can’t we just say, “Nothing. Absolutely nothing.” Because that’s the truth, isn’t it?
6. Why do you require that we create forecasts that show that we will generate more sales in the first five years of operation than any other company in the history of man in order to get a term sheet? Guess how I got laughed out of my first VC pitch? I actually showed 4 years of achievable sales. Sometimes it feels like VCs don’t want to invest in achievable. Achievable is boring.
7. As for the last question, good point. If you aren’t a proven entrepreneur, don’t say you are.

I’m not anti-venture capital by any means. There are investors in my community who are devoted to educating entrepreneurs and I respect that. Despite my criticism of Guy’s questions, he has actually done a lot to help entrepreneurs hone their pitches. I know that I have used many of the rules in Guy’s 10/20/30 Rule of PowerPoint and you should too. A lot of VCs and angels do a lot to prepare entrepreneurs. After all, these guys keep us entrepreneurs in business.

At the same time, I think it is relatively easy for an investor to get stuck in an ivory tower and assume that entrepreneurs are dumb because they bring an NDA with them. Maybe what it really means is that your VC corporate website sucks.