If I knew then what I know now is a series of bylines from small agency executives about the lessons they learned in building their shops.
I had the good fortune of starting my career at an irresponsibly creative agency that insulated people like me from the financial practicalities of running a business (our own as well as our clients'). We were barely even an agency, really. We were a group of professional "imaginators" living in a creative reality distortion field. It was fantastic.
Our job was to play "What if?" In fact, the only time you got in trouble was by allowing practical thinking to invade your brainstorming. They fired a guy for asking, "Can we afford this?" I heard he's working for WPP now. That attitude managed to work pretty successfully for a while, because the agency grew and grew. But, like all good things, one day it came to an end.
Later I found myself at an agency that was on the opposite end of the fun spectrum, where basically anything resembling a creative thought was, by default, out of the question and out of the budget. So, when I started Circus Maximus in 2013 I didn't have a clear, consistent view of how a business that sells creative thinking actually operated, like, you know, financially.
After founding the agency, I soon began to learn, and quite quickly at that. I have a belief now that there are only two kinds of lessons in life: painful or expensive. (Sometimes if you're unlucky, you experience both.) Fortunately, (and miraculously) I haven't made any mistakes that have been terminally foolish, but I've certainly contributed a business school education's worth of teachings into the "that was dumb"/expensive column.
Capitalism is important
I now know, it's called capitalism because when you have capital, you can compete, and when you don't it's an awful lot harder. Capital creates the appearance of success, which is terrific bait for actual success. Capital affords things like staff, and office space, laptops, bagels, coffee, toilet paper, Wi-Fi, a membership to Working Not Working, agency swag, you know: important stuff. I thought all of these things would come after the agency started making money. I was an idiot. In fact, you need capital to pay for all those things before you're actually able to convince people that you have what it takes to do the job they're paying you to do. It's backwards, y'all! You need to be a totally functional business before you can even think about being a totally functional business. By far the most important thing capital can buy you is time, to wait for luck to roll around. And luck will eventually roll around, but you have to float those stretches in between. And they can be long, and lonely.
Have a perverse work ethic
We began working with multiple startups, and if there's one thing startups have a lot of, it's opportunity. They also have hope and potential, and that's where the fun, enthusiasm, risk, and optimism lies. It's also where consequence, failure, and existential dread lives. Startups offer the outside chance of waking up a millionaire if things work out. So, we got to doing that, and were able to claw our way up the capitalist ladder bit by bit. We're still on that climb, but the process has yielded some other valuable lessons: you need a perverse work ethic, you have to develop the ability to manufacture optimism when all conditions call for the contrary, you need to find yourself some similarly ignorant fools to do it with, because you can't do it alone, and you need to cultivate a belief that no matter what comes your way, you'll be able to figure it out. Because that's the important stuff that capital can't buy.