Venture Voice – interviews with entrepreneurs

Entertaining Entrepreneurship

Asking the Hard Questions

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I really enjoy hearing from listeners. The best comments are the ones that challenge us and make us think about how we run the show. Andrew Cheung recently sent one in using our nifty contact form and selected the “You may quote me on this” option, so I’m going to share his comment and respond to it here.

Andrew writes:

Hi Greg,

I very much enjoyed listening to the stories of David and Steve who you recently had on.

My main question to you is that when you interviewed these guys (and possibly other people too), is there are a particular reason why you tend to have a focus on the negative aspect of things? It just seems to me that your angle of questioning at times seems to be on the negative side of things. I guess its particularly pronounced when listening to these very inspiring guys and the negative line of questioning gets really emphasized.

Don’t get me wrong, I love to hear what problems these guys had to overcome to get where they are now. But it just seems at times you like to keep digging at the problems rather than focusing on how they found the solutions to their problems.

I thought David had so much passion and enthusiasm, it would’ve been great to hear more about why he is so fired up.

I guess I’m not sure exactly what your philosophy behind your interview technique is, but I just thought I’d give you my 2c worth. I think you have extremely high quality people on the show and hopefully we can all get inspired by them listening to your show.


Thanks Andrew,

It really means a lot that you’re taking the time to give me such specific feedback. I’ve learned a lot from my listeners.

I’m very deliberate in my style and it’s not because I’m trying to be negative. I’ve been an entrepreneur ever since I was 14, love entrepreneurship, and really enjoy talking to the people who I’m lucky enough to have on my show.

However, I started the show because I felt a lot of coverage out there on entrepreneurship is fluff and glosses over the hard issues that entrepreneurs deal with on a daily basis. Because of that, aspiring entrepreneurs get a skewed view of what they’re about to get into and are often unprepared. Worse, when entrepreneurs only talk about the positives (which might well be a good practice for sales), other entrepreneurs feel as though no one shares their problems.

Besides, the questions the entrepreneurs get from me are nothing compared to the skeptical questions they get on a daily basis from prospective customers, VCs and the traditional media. Great entrepreneurs don’t get discouraged easily.

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