I’ve come to realize that startup investing is very much like my experience with online dating sites. Despite dating sites attempting to match people via their personalities, attributes, and interests, it still really boiled down to one thing: how they looked in their profile pictures. I know that sounds incredibly lame, but after trying dating sites and also talking to others who have used dating sites more than me, the main reason why someone responds is if you like how they look in their profile picture and whether or not you’re attracted to the way they look.
I have found that a major reason why I invest in a startup is if I feel some kind of personal attraction to it. Some of those personal reasons are:
1. I’m personally interested in the area that the startup is working in.
2. I have some emotional connection to their project, perhaps due to some similar project I had worked on in the past.
3. It tickles some intellectual part of my psyche, and my desire to learn more about their space.
4. There is some inherent coolness to their project, and that coolness may rub off on me from a brand perspective of being associated with it.
…and so on.
However, none of these reasons have any kind of relation to whether the startup makes any kind of business sense. A startup could very well have a strong business case, even up to the point of having lots of traction and revenue, but yet be unsexy to me. I think there are many untapped business areas that aren’t all that sexy and therefore ripe picking grounds for new entrants to disrupt old businesses in those areas and do very well. In fact, I’ve met some, BUT…have found that I just could not pull the trigger.
I’ve come to realize that it just boils down to personal attraction. On a dating site, I found that if a profile picture wasn’t attractive to me no matter what the site said how much her attributes were compatible with mine. The same goes with startups; if for some reason the project isn’t all that sexy to me, I just can’t seem to bring myself to do it.
As an angel with limited resources, I need to deploy them smartly and maximize their value to me, which also includes a sexiness component. That’s not to say that there aren’t angels out there who would take a chance on something unsexy to them; I think that for them, it’s more about being part of a great business and building it then the inherent product area they are working in. Me, being a product and UX guy, I love being associated with products I love, which introduces an inherent sexy bias when deciding on whether to invest or not.
I think that if I were running a fund, my decision process would be broaden to less sexy projects. Still, we have limited time and resources and need to make sure value can be added to the startups even in a larger portfolio and need to pick wisely for the reasons we have. I think that when you’re investing someone else’s money, you’ll have to think twice about passing on something that can produce a gain for your investors.
However, all this sucks for entrepreneurs who are working in business areas that aren’t part of what’s hot right now. Real time? Ride the excitement of Twitter and Ashton Kutcher! Social? Maybe that’s so yesteday. Social gaming, now that’s sexy! Virtual goods yeah! Processing waste? Yech, even if it is profitable. I think you get the idea.
How does an entrepreneur combat unsexy? I think it’s like improving your chances on a dating site:
1. Some people just aren’t attracted to you, so you’ll just have to get over it. There will be some investors who just don’t think your project is interesting enough to them and you won’t be able to convince them otherwise.
2. Improving your profile picture helps a lot. So how do you improve the way your startup looks? You may introduce some interesting component to your plan that makes your project more sexy. You might actually increase the sexiness of your visual/interaction design. That in itself may be enough to sway an investor to like you versus not.
But beware of pursuing sexy for sexy’s sake. Even though we may look for dates of attractive people and they may be eye candy to us, in the end, it’s what’s underneath that drives whether we will go out with them again. So even as you dress up your project, it may take you down a path that is detrimental to your future. It may even waste your time as you should be working on your core product.
3. You could rewrite your profile description to be more fun and engaging, which in theory is a reflection of how cool and fun you are. This is like creating a better pitch deck, or sexy prototype, or some kind of cool new UX for your product.
4. You could learn how to chat better and be more interesting and fun, which is probably a skill that is more for men than women and sort of like learning how to pick up girls. This is worthwhile both before the actual face to face and during the date. If you write an engaging first message to a prospective date, that can solicit a response better than a boring, lame one. Certainly chatting up someone better during a date will have a great effect on whether you get another date. This is like when you may simply just pitch better and that can be sexy in itself when the sales job is so good you can’t resist falling under the spell of a great pitch guy.
5. Go and find someone who likes you the way you are, which means that being on a free for all dating site like Match.com is not right, but maybe eHarmony is more for you. Tackling a non-sexy business in the world of sexy can be tough, even if the potential benefits are clear to you. As in dating, you should probably go and find someone who loves you the way you are now, versus trying to put on a different dress or suit, or changing your make up or hairdo.
Thus getting introduced to the right investor, who actually does know something about your industry, can get you the resources that you need.
Still having said all that, it may not be enough to convince me to invest in you. I just may not find you sexy enough even if you are wearing a thong bikini…