The First 1.5 Years as an Entrepreneur

Hello again. It’s been a while since my last post, hasn’t it? The holidays have kept me busy, and now it’s 2009. Damn, time sure flies when you’re having fun.

It’s been two years since I started this blog and a year and a half since I struck out on my own. So I figured it was time to take stock of my first 1.5 years as an entrepreneur (like I did for my first four months). And I can sum it up in three bullet points:

• It’s been fun
• It’s been crazy
• It’s been a tremendous learning opportunity

It’s Been Fun

Whoa boy it’s been fun! Setting up my own schedule, deciding what I want to do today, and where I want to do it. The sense of freedom is tremendous. Finally, I get to hang out in the city during the weekday – and do free stuff in San Francisco to boot!

With my office being any cafe with free wifi, this freedom and flexibility means I can work almost anywhere. San Francisco, Los Angeles, New York, Hong Kong, London, Florence, you get the point. Yup, life is good.

One odd thing to note: it’s funny to go shopping during the weekday. Sometimes I’m the only young guy walking around in the mall. Surrounding me are scores of housewives, work-at-home moms, and retired persons. And sometimes their babies too.

It’s Been Crazy

It isn’t all roses and peaches though. Without the cushion of a regular paycheck, monthly bills can become a source of stress. In between brainstorming business ideas, working in cafes, blogging, reading, writing, working on personal projects, consulting, and hanging out with friends, I’ve also been building a few businesses – one of which I’ll announce as soon as our website is up!

Yes, that’s a long list. That’s part of why it’s been so crazy & hectic.

The other part is the fact that most of those activities aren’t revenue-generating ones. Each month, I watched my bank account whittle away. Fortunately, a few consulting gigs helped pay some bills. But the fear of failure always loomed.

This fear both inspired me and wore me down. Ultimately, it inspired me. After all, I quit a six-year career at Yahoo! (YHOO) not because I hated the company, but because I didn’t want that the cushion of a regular paycheck anymore. I knew that I would never take a true entrepreneurial risk with that safety net below me.

So it’s been crazy. Despite my new-found freedom, I feel like I’m busier than ever. Fortunately, it’s a good kind of crazy – it’s exactly the kind of crazy I want.

It’s Been a Tremendous Learning Opportunity

I could have never learned what I’ve learned had I stayed at a large corporation. That doesn’t mean you can’t learn anything at a large corporation; you just learn different things at a large corporation than you would if you were an entrepreneur.

As an entrepreneur, you have to think about every aspect of a business. You’re not just writing the code, you’re writing the functional specs, setting up the business entity, outsourcing tasks that can and should be outsourced, interviewing CPAs, interviewing lawyers, interviewing insurance carriers, doing the marketing and sales, doing the quality assurance testing, designing the logo, setting up a bank account, keeping track of expenses & receipts, dealing with taxes… the list goes on and on.

Meanwhile, at a large corporation, you keep on doing the same job you were hired to do. That alone isn’t a bad thing. If you are good at a specific role, and want to continue doing it, there’s no reason you shouldn’t specialize. Even as an entrepreneur, doing everything yourself is impossible. You’ll need partners, employees, vendors, contractors, and others help you out.

Someone once told me about the T-Person concept. This concept explains that some people have a wide range of skills at a novice or intermediate level (represented by the top horizontal bar of the T), then specialize in one particular skill at a deep or expert level (represented by the middle vertical bar of the T). I like this concept. I think it explains an entrepreneur very well.

It is possible to be a T-Person at a large corporation, of course. I knew many who were at Yahoo!. However, the horizontal bar is wider as an entrepreneur. Arguably, the vertical bar could be deeper too, since you’re forced to delve further into the discipline to maintain your viability as an independent entity and aren’t encumbered by corporate politics.

All of this has been a tremendous learning opportunity. So much so that, despite the uncertain economy, it is hard for me to imagine going back to a large corporation again. That’s not to say it’s impossible, but I sure can’t see it in the near future. Being an entrepreneur is just too fun, crazy, and educational!