Coffee is For Closers

Back in 2011, when my first book Street Freak was coming out, I had a call with my friend Larry MacDonald, author of the wildly successful A Colossal Failure of Common Sense, and he told me in plain language that the publisher basically wasn’t going to do shit to promote the book and I was going to have to do it all on my own. What? A publisher publishes a book and doesn’t promote it? The author has to promote it? He was right. The marketing budget for that book was $500, which was used to buy banner ads on a blog run by a guy who was badmouthing the book on another blog. That was our marketing effort.

I can tell you that self-promotion does not come naturally to me. I did it for Street Freak, reluctantly. A friend of mine knew a reporter at the Los Angeles Times, and I got an interview there. Through a complex series of connections, I wrangled a review with Kevin Roose at Dealbook. Larry himself got me a spot on the Dylan Ratigan show on MSNBC. To their credit, the publisher did a few good things, like getting a fantastic book review at Bloomberg, and a lukewarm review from Dan Primack at Fortune. But I basically had to hustle the whole thing. It caused me psychic pain. It causes most authors psychic pain. It is hard to advocate for yourself, to say, hey, I wrote this great book, look at me, please write about/talk about this thing I made so I can sell a million copies of it. I’m going to prostrate myself in front of you and lick your toes so you say nice things about me. I’m going to beg for it. My whole livelihood and reputation depends on you saying nice things about my book. It would be nice if someone would do this on my behalf, but since my publisher doesn’t do shit, I have to go hat in hand to turd journalists and beg. See how much this sucks?

This applies to the music world as well. A few months ago, I spent some time looking up clubs in various cities and sending emails to see if I could get a gig there. Well, it worked—once! A club in Jacksonville is having me play there on July 11^th. But it’s the same sort of rigamarole, I have to advocate for myself, and send them my electronic press kit, and say please please please can I play at your club? As you can imagine, the vast majority of these emails get round-filed, in spite of the fact that I have played at some of the biggest and best venues in the country. I hate begging. I’m 52 years old; I’m too proud for it, and I’m too old for it. I’m not some 20-year-old jagoff playing with a Serato controller and a laptop full of porn. Never mind social media. All of this stuff is done over Instagram these days, and now that I have been steeped in the music scene for a little while, I get the impression that these DJs spend the vast majority of their time curating their image on Instagram, rather than making music. I don’t quite understand it. I barely know how to make an Instagram story, I barely know how to put text on it, and I don’t know how to tag people or add music to it. There is a lot of sucking up that goes on in Instagram. Club owner A posts a picture on Instagram, and DJ B, DJ C, and DJ D all have to put some vapid comment on it to kiss ass and stay in the front of the club owner’s mind. Maybe I am just some old armadillo Gen Xer that grew up in the 80s and 90s when we had the closest thing possible to a pure meritocracy. The best music should win. Well, either things have changed, or I am incredibly naïve, because it is all about the ‘gram and it is all about butt snorkeling. I retain some hope that remaining detached and aloof, rather than being needy and annoying, works in my favor.

Well, on Wall Street we had a term for this—asking for the business. The salespeople intuitively understand this. You can’t expect someone to trade with you just because you exist. You have to pick up the phone and call them, smiling and dialing. You have to take them out for steaks. You have to take them out for handjobs (well, not anymore). If you were unable or unwilling to do these things, then you had to be exceptionally smart, and have good ideas. But again, you can’t just sit there and wait for the business to come to you. You have to advocate for yourself. And unless you were trained in sales, unless at one point in your life you had to sell timeshares or pest control, most people do not how to advocate for themselves. Most people are bad at sales. The good news is that you can get good at it if you work at it. Some people get very good at it. You can become a millionaire by selling just about anything, including pest control and timeshares, if you are talented.

So since I have been in the position of asking people for help, I generally don’t fault people for asking me for help. Quick story—when I was advocating for myself and trying to get journalists to cover All the Evil of This World, I reached out to Aaron Task of Fortune in the Twitter DMs with a pitch. But I screwed it up, and said “Forbes” instead of Fortune. Well, within minutes,he composed a tweet publicly making fun of me, and other journalists were piling on. I think he’s going to smoke a turd in hell for that one. Come to think of it, I haven’t heard from that guy in the while, so maybe he got spit out the bottom of the journalisming industry. I get emails like this a lot—young buck at Okeechobee Swamp Univeristy reaches out on LinkedIn and wants career advice. Nobody has time for this shit, but I try to make time if the request is reasonable. You pay it forward. Sometimes I am in a position where young buck asks me for help finding a job. I tread carefully here, because you don’t want to expend reputational capital on marginal performers, but if they are good, I will do it. I did it recently. Someone helped me get a job on Wall Street once, and for that, I am forever grateful, and I will pay it forward. And I know how hard it is to advocate for yourself.

That’s one of the reasons I like the movie Glengarry Glen Ross. I didn’t see it until late in my Wall Street career, but if you ever thought about pursuing a career in sales, you have to watch this movie. Yes, everyone loves the Alec Baldwin rant, but it is much more nuanced than that. A Always B Be C Closing. I’ll never forget it. Everyone wants the shortcut, the Glengarry leads. There is no shortcut. And in sales, there is rejection. Rejection after rejection after rejection. A friend of mine once did cold-calling for a brokerage firm. He got hung up on 99% of the time. No surprise—if someone calls me selling something, I save them time and hang up in the first two seconds. Another friend of mine was very successful with the opposite sex. He viewed it as just a numbers game. If he asked 100 women out, one of them would say yes. He got more ass than a toilet seat at Lilith Fair. The guy had absolutely no fear of rejection. Rejection is like anything else—you get used to it after a while. My brother is in a sales business and when one of his deals falls apart, he views it with some equanimity. There will always be others. I will say one thing for sure—it is hard to sell timeshares or dental practices or yourself—when you are desperate. You want to be dealing from a position or strength. You can’t need it—or appear to need it. I’m sure you’ve experienced this phenomenon when you were on the dating scene that you were on the receiving end of many more romantic advances when you were already in a committed relationship. Because you had confidence.

Like I said earlier, none of this comes naturally to me. I am not the person who feels comfortable reaching out to rando journalist about my book. I am not the person who feels comfortable asking for DJ gigs. I’m not on the dating scene, but the idea of asking a woman out, to me, these days, is terrifying. But life is all about sales, right? Life is a presentation? Life is a performance? Well, there are a million ways to make a million dollars, and if you are an introvert, you can just do what I do, which is to write cranky essays on your laptop in the living room while watching the Yankees. You can compensate by having a big brain. And if you don’t have a big brain, then you better have big muscles. And if you don’t have big muscles, you better have a big personality. And if you have none of these things, then you will spend the rest of your life worrying about getting health insurance.

P.S. I am advocating for myself. Please pre-order The Awesome Portfolio. Why? It will change the way you invest—forever. It’s a future classic. It’s a short book, and it will be the best four-hour investment of your life. And you can’t blame me for asking.