Advice from a Small Business Wannabe

I turned 36 years old this year. And for the previous 16 years, I had been pursuing a career as a full-time artist, first as a photographer and then as a writer. And I ended up self-publishing most of my books, and scheduling my own tours, and had my successes, and had my fans. And then one day last year I woke up and realized: I don’t want to do this anymore.

I turned 36 years old this year. And for the previous 16 years, I had been pursuing a career as a full-time artist, first as a photographer and then as a writer. And I ended up self-publishing most of my books, and scheduling my own tours, and had my successes, and had my fans. And then one day last year I woke up and realized:


I don’t want to do this anymore.

I realized that what I really want to do these days instead is to make this process easier for other underground artists; to open a commercial arts center here in Chicago, in other words, one that would publish underground writers’ books, schedule tours for them, feature them at live local events, get them connected with wealthy fans, the whole shebang. And it was at that point that it hit me — just how does a 36-year-old former artist actually learn everything he needs to, in order to open his own small business? You know, without returning to the world of academia, which is pretty much the last thing I ever want in my life again? (My undergraduate years, needless to say, were a bit of a nightmare.) How do I learn about the different types of business incorporations, and how I actually register one with the government? How do I learn about taxes, and marketing? What’s a business plan, anyway, and why is it so important that I have one?

So, that’s what I’ve been doing with the last year of my life; simply discovering whether it’s possible for someone to teach themselves everything they need to know, in order to open a small business and have at least a fighting chance of it being a success. And here’s the surprising thing — it’s not only possible, but easier than you might expect. So in celebration of BlogJam 2005, I thought I’d write a guest entry about what I’ve learned, and what tips I would offer fellow FC readers who are in the same boat as me.

Read. A lot. Of books. When you think about it, really, the majority of college classes mostly consist of reading textbooks, and then getting tested on whether you understood what they were saying. And really, you don’t need a college campus in order to do this; all you need is your feet, a wallet, and a local bookstore (or even easier, a credit card and a virtual bookstore).

Of course, the tricky question is what books you should actually be reading, especially when you’re someone like me who doesn’t know anything about business going into it. And so I applied the lessons I learned from the literary world, and have so far been pretty happy: that if a book features fancy graphics and a killer cover, they’re usually trying to hide some pretty weak content; that the more emphatic a guarantee a book has on its back flap (i.e. “This book WILL make you a millionaire!”), the less likely it is to be true; and that if a book is famous enough that you’ve already heard of it, the chances are 90 percent that it will be worthwhile.


Of course, there are resources available as well; in particular, I’m a fan of Josh Kaufman’s Personal MBA 40, his list of what he considers the most important 40 books business people should read. And of course, let’s not forget the best trick of all: when you read a book you admire, write down all the books that author has mentioned in the text, and go read them too. It’s as true in the business world as it is in the arts, I’ve discovered — if you find an author you admire, the chances are most likely that you will enjoy the other authors that person admires.

Bug the people you admire. You know, nicely. One of the subjects I in particular have gotten obsessed with over the last year is that of marketing and public relations, and how they are vastly larger subjects than I had ever realized. And so, every time I read something by a marketing or PR veteran that I really enjoyed (like Piers Fawkes, Seth Godin, Douglas Atkin, Steve Rubel and others), I simply dropped them a line and told them so. In every case I tried to be as simple and straightforward as I could; that I’m teaching myself business right now, that I really liked what they had to say, and just wanted to let them know.

I’ve discovered something about this process that may come as a shock — business writers don’t receive a lot of fan mail. Most of these people I mentioned, in fact, were so tickled by receiving mine that they wrote right back; and in my particular case, I have ended up forming regular correspondences with a number of these people, and have even gotten a lot of really great advice from them (free advice, I might add) about this center I’m trying to put together these days.

Now obviously, don’t be a jerk about it — a naked attempt at exploiting an expert is always a naked attempt at exploiting an expert, no matter what subject you’re talking about, and these experts can usually see right through it and will resent you for it. Instead, I encourage you to simply see it as a way to say hi to those hardworking authors out there you admire, who frankly deserve to hear from a lot more of their readers who enjoy reading them. If you go into such a process simply thinking, “Maybe I’ll make a new friend out of this,” your chances of additional benefits coming along as well will be much greater.

Get on the web, man! Of course, if you’re reading this entry you really don’t need to be told this, but it never hurts to mention it anyway. It is simply unbelievable, I think, just how many insanely great business blogs are out there these days, and just how insanely much you can learn by simply reading them regularly. And even better, most of these blogs allow commenting, which provides that other benefit that comes with business school — the opportunity to talk with your peers and mentors, and to build conversations about the things you’re reading in these books. I have many times learned more about a business subject by reading a blog entry’s contentious comment thread, than I did from the actual entry itself.

And speaking of which, let’s not forget all the discussion boards, wikis, peer associations and other interactive places on the web for fellow small-business newbies. For example, I’m a member of that “Personal MBA” site I mentioned before, and all of us there are just about to start up on a big group discussion about the first book on the list, Scott Berkun’s The Art of Project Management (and even better, Mr. Berkun has happily volunteered to be part of the discussion group, and how great exactly is that?). The web is simply fantastic when it comes to such things as finding likeminded individuals around the world who are going through the same thing as you, and can easily be an inexpensive substitute for the interaction you usually only get from an academic environment.


I have more advice, actually, but this entry’s getting long as it is. Until tomorrow, then, I remain your humble clueless small-business wannabe.