Don’t be shy (continued)

Yesterday, I spent some time talking to a founder in NYC. We’ve become friends over the last year or two. We decided not to invest in his company for reasons that I won’t get into on this post. But I’ve tried to be helpful because I like him. 

He is in the process of raising a seed round. We were talking about possible investors that he should talk to and I shared with him my thoughts on who I thought were great and not so great. 

I suggested a name of an investor that I really like and this founder said something like “he’s great. but, he knows who I am and what we are doing. if he was interested, he would call me, right?”

I understand this logic. It’s not a lot of fun to fund raise whether you are a hot company or one that is grinding it out. It takes time and getting a rejection ain’t easy. Also it’s more desirable to be wanted than to try to convince someone of something. 

But if you like the investor, I would recommend staying close to them and give them the update on your progress, your plans and your vision. We have a few startups in our portfolio that we passed on (a few times) before we made our initial investment. Sometimes it’s the progress and sometimes it’s the sheer will and determination that gets us over our concern.

Don’t be shy. Make the call and get the meeting. The worst that can happen is they turn you down. That’s not awful either. Remember, you get to show them how wrong they were :)