Why Mentoring is Dream Killing (Most of the Time)

As a startup entrepreneur, and not yet a very successful one (if you measure success by how many exits one has had), I am honored and privileged to be invited time and time again to mentor in my local startup ecosystem. Most recently I was asked to present about my startup journey to a wonderful group of female Palestinian entrepreneurs from Ramallah. It was truly one of the most humbling experiences I have had as an entrepreneur and deserves its own post (soon). Starting next month, I will be one of many very talented and awe-inspiring mentors for the new Barclays Techstars accelerator in Tel Aviv, as well as often volunteering my personal time to mentor other mums or females starting out, helping them take their ideas and turning them into functional startup businesses.

And yet… As a mentor I find it is a very fine and often-times hard line to walk between helpful advice and dream killing. All too often I find myself on the side of “Dream Killer.” Recently I met a lovely, bright and very enthusiastic potential entrepreneur who put out a cry-for-advice in one of my mummy groups. It was one of those “I have an idea for an app that I think is brilliant, and I want to hear from someone who understands what is involved or whether to pursue my idea.”

The session with her started with me being forced to sign an NDA, even though I assured her that firstly most people are not interested in stealing your ideas and more importantly, there is really no such thing as a new idea — just different ways to do things. But… I signed anyway. She went on to tell me about her idea. It was great, had real merit with a clear pain/solution, a potential business model and a sort-of not fully baked go-to-market strategy. So I proceeded to spend 2 hours of my very precious and rare time telling her the reality of what she would face if she really wanted to take on her idea. The reality of how hard it would be to raise money. The reality of how difficult finding co-founders might be. The reality, particularly in her case, of realistically making her venture successful if she had no money and didn’t want to give up her job while she did this on the side. Finally the reality of how up and down it could be, and just how damn hard it all is! As I spoke I could see the light go out of her eyes, I could see her enthusiasm waver, I could see that I had turned from mentor into “Dream Killer.”

So I made sure I also spent a good amount of time talking up the good things. Telling my story and highlighting the fact that, although there are many things I would have done differently, I would still choose to do it all again in a heartbeat. Making sure that it was clear that at the end of the day, I wanted to be as honest and open as possible highlighting not only the negatives, but also the positives. However, at the end of the day only she could decide whether or not the rewards would be worth the risks.

Yet the final nail in her dream coffin, although initiated by me, was of her own doing. I just happened to receive a list of the hottest 30 UK startups in my email the following week. One of the startups on that list, who had already raised a significant amount of money and had significant market traction, was doing EXACTLY what she wanted to do… Now ordinarily that in and of itself is not a reason to give up your dream. But if your dream is a half-baked something you may want to do on the side, without taking any of the risks and without preparing yourself and DOING YOUR HOMEWORK. Then… sorry to say — Don’t bother… signed “The Dream Killer.”