They say the definition of crazy is doing the same thing over and over again and expecting different results.
If true for entrepreneurs, it’s not me, it is most certainly you.
Of course, most are too accommodating and polite to say it to you… leaving it to me today.
If you are pitching investor after investor and hearing the same thing, particularly when not asking for feedback, you are crazy.
I’m serious. When you don’t close the feedback loop, when you are not improving your pitch, you are crazy – and it comes across as crazy to investors, who tend to talk to each other about you.
Doing this for long periods of time makes you look… well, untouchable, and not in any good way.
Some particularly crazy entrepreneurs in my home market of Tampa Bay attempt a turn to doing the same thing in a different market. New York City will be better, maybe Silicon Valley. It must be the geography that was cramping their style… sorry, I cannot even finish this thought… it is just too ludicrous.
Are you serious? You think raising money will be easier in (1) a market you don’t know or understand, (2) with no network, (3) where you are a small fish in a very large pond, (4) where the investors know more about your market than you, (5) because there is a ton of deal flow in your space?
I know, I know… “there is no money here”. Yes, I’ve heard it before.
It couldn’t possibly be that there is a lot of money here, it just isn’t being given to crazy people, right?
So, I’m willing to help anyone, but if you are not willing to listen, I cannot.
And the investors will continue to ignore you, just as you ignore them.
And yes, you may be “out trying to raise money”. But you aren’t really, are you?
Does it count as trying when you don’t care enough to get better, or ask for help, or listen to feedback?
No. You are just “out crazy to raise money”.
My newest favorite phrase… “crazy to raise money”
PS – On a closely related note… If you ask me for help to get into TechStars, when I run a world class seed-stage investment program in your backyard, you come across as an asshole… and I will instantaneously get crazy about ignoring you too.