How To Make It as a
First-Time Entrepreneur

Vinicius Vacanti is co-founder and CEO of Yipit. Next posts on how to acquire users for free and how to raise a Series A. Don’t miss them by subscribing via email or via twitter.

As a former i-banker, I struggle to overcome each of the following five shortcomings. I’ll write about how I’m dealing with them in future posts. But, the first step is recognizing you have a problem.

1. You have no useful start-up skills. You certainly didn’t learn how to program (cheap excel macros don’t count). But, it turns out that i-banking didn’t teach you essential non-technical skills either including product management, marketing or fundraising skills. You’ll need those skills, not just an idea, to attract a technical co-founder.
2. You hesitate to make uninformed decisions. In the i-banking world, you were taught to never make decisions without fully investigating the issue. In the start-up world, you are better off making 100 decisions with a bunch being wrong than 10 well-researched decisions.
3. You’re a perfectionist. When I joined The Blackstone Group, Steve Schwarzman, the company’s CEO, told us:  “99% right is 100% wrong”. In the i-banking world, you had to be perfect — the numbers had to tie, the formatting had to be consistent, and, above all else, no extra spaces. In the start-up world, you can’t afford to be perfect. You can only spend 20% of the time to get 80% done.  You don’t have time for the last 20%. As Reid Hoffman, CEO of Linkedin, said:  “If you review your first site version and don’t feel embarrassment, you spent too much time on it.“
4. You don’t network. In the start-up world, you’re told to never eat alone. But, in i-banking, you always ate alone at your cubicle. If you were lucky, you got to eat dinner with some of the other analysts in the conference room.  In the start-up world, you need to become a member of the tech community. You need to meet everyone because those people can help make or break your start-up with their support and ideas.
5. You’re too private. You spend hours adjusting your Facebook profile privacy preferences to make sure you couldn’t be searched. You never tell you friends about what you’re working on — you weren’t allowed to. You’re not a self-promoter.  In the start-up world, you can’t be secretive. You have to talk to you friends about what you are working on without making them sign an NDA (sorry to the people I did this to). They’ll completely change the way you are thinking about your project; they’ll make valuable introductions.  You need to start a twitter account and a blog. You need to become a self-promoter.

Fortunately, what you did learn on Wall Street was how to work incredibly hard and do 30 things at once. You just need to be aware that you have some new habits to pick-up and a few habits to lose. I’ll continue writing about what I did to overcome each of these limitations here and you can follow me on twitter. (see #5 for self-promotion).

Update:  Interesting post by Kate Huyett on 5 Things I Learned in Finance That Are (So Far) Helpful at a Startup

Vinicius Vacanti is co-founder and CEO of Yipit. Next posts on how to acquire users for free and how to raise a Series A. Don’t miss them by subscribing via email or via twitter.

“If you review your first site version and don’t feel embarrassment, you spent too much time on it.”

• Reid Hoffman, Founder of LinkedIn

As a pseudo-perfectionist / borderline-OCD’er, I have the hardest time not spending way too much time getting everything to be just right.  This applies to everything:  programming, user interface design and even my commute to work.

Now, whenever I get frustrated that I’m not doing something in the “best possible way”, I just say Reid’s quote to myself and move on.  I’m a much happier / productive person.  I hope his quote will also help you.

After about a year and a half of wresting with David Allen’s critically-acclaimed self-help book, Getting Things Done, I can confidently say that the recommended organization system is impossible to keep up with for all but the most impressively disciplined / insanely masochistic amongst us.

Was it all a waste of time? The answer would probably be yes except there is one simple and completely realistic piece of advice in the book that dramatically improved my efficiency. I now recommend it to everyone:

• If you find out you need to do something that will take you less than two minutes to complete, do it right there and then

That’s it. Simple and realistic.

If you don’t take care of that small task immediately, it will sit in the back of your mind and rot. You will spend many more minutes constantly reminding yourself of having to take care of it instead of creatively thinking about your business / life. Also, reminding yourself of things you have to do are not exactly “happy” thoughts. Eventually, you will either end up taking care of it or, more likely, forgetting about it all together.

Do yourself a favor and start taking care of those 2 minute tasks as soon as you become aware of them. I briefly flirted with the idea of raising the bar to 5 minutes, but it almost killed me.