An Email to Donnie

Rick Webb
Rick Webb
Published in
6 min readApr 27, 2015

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A stranger emailed me asking for advice as he balances his art and his career. This is what I wrote to him.

Hey Donny -

Sorry for the delay. I have just moved down to Chapel Hill, NC, and been unpacking and setting up this house and haven’t been hitting the email much. Just now starting to get settled and back in front of a computer with any regularity.

Read your email, and you’re right. A lot of it rings familiar. To give you a quick summary, I used to play in bands, a lot, and was really making a go of it. Me and some other friends from other bands started a record label as a collective together — the Archenemy Record Company. It’s still around, but it’s really just kind of a hobby at this point. From there, I got into tech and advertising, and eventually started an agency, the Barbarian Group. Worked there for ten years, sold it. Loved it, but eventually left in 2011, and since then I’ve been working mainly in tech — consulting for startups like Tumblr, Soundcloud and Percolate. Lately, though, I’ve decided to pull back a bit and focus a little more on my art again — this time writing (hence the move to Chapel Hill). Not completely, but… more.

The thing about this path that makes it different from you is that we chose the exact worst time to start a record label. The CD market was imploding, but there was no robust online alternative yet. No Sound Exchange, no iTunes music store, no streaming, maybe a little internet radio, but it paid nothing. Our bands were decent and the label had good buzz, but it was so, so hard to make a go of it then, especially without any money to fund things for a few years as we got off the ground. Recently I read a history of an 80's English label, Factory Records. It all sounded pretty familiar until I got to the part where they decided how many copies of their first 7" single to make. 25,000! Can you imagine, in the 90's or 2000's, someone pressing 25,000 copies of a vinyl single? Hell, I’ll bet Taylor Swift didn’t make many more copies of 1989 on Vinyl. I mean, if we could have sold 25,000 copies of a single, we’d have done great! But by then, you were lucky to sell 1 or 2,000.

ANYWAY, because I couldn’t really make a viable go of the label, I decided to “get a job” and just “play in a band.” My friend asked me to start Barbarian Group, our agency, with him, and I thought “that’s a way to make some money. I’ll go back to trying to live off of my art afterwards.” And, so, 14 years later, here I am.

So… what do I think now? Well, I’m rich, so that’s nice. In terms of my art, though, I still feel like a dillettante, I still feel like it’s a hobby. I never did the trial by fire of trying to make a go of it no matter what, no matter whether I made money or not, and ajusted my living habits to those of a poor artist. Is that good or bad? I don’t know. I have friends who stuck with it, just kept going no matter what, and they all sort of eke out a living off of their music these days, which I find to be really amazing and impressive. Of course, they probably find my own accomplishments impressive, so who can say. The grass is always greener, right?

I’ll tell you another story. 1999. I was at SXSW. On a photo pass from a friend’s zine, one of my friend’s bands was playing a showcase. Another friend was down there tour managing another band. Our label was still going, but I had started freelancing in advertising to pay the rent. I wasn’t doing tons of work, but the money was insanely good compared to what I was used to. Me and these friends and some of their friends were all sitting at a bar at SXSW and eventually a few of them all started talking about how much money they made. These were like A&R people at major labels, stuff like that. They all made NOTHING. I mean, ridiculously low salaries. Like I made more in my 1–2 days a week working in advertising than they made. And it just struck me: Of COURSE they don’t make anything. EVERYONE wants to work in music, and they’ll do anything to work in the industry. You can never make a good salary working in music.

Since then, I’ve touched over to the music industry through the years. Did a bunch of work for Justin Timberlake for a few years, a bunch of work for Shakira. I would go with their managers to go meet people at the labels. At their web divisions. Etc. And you are 100% right. Well, you’re 90% right. There ARE a few smart people in the music industry, but the industry as a whole is SO DUMB because a) it’s institutionally set up to deny the reality of the internet and b) there are SO MANY dumb people who just want to work in music that the ratios are so far off that it’s impossible for the smart people to make a difference. And the smart people are usually either biding their time to get out, or they’re just biding their time till retirement.

Many people realize this, and typically people in your position upon seeing this think to themselves “well I will start some startup in the music industry and change it all and make a mint!” I confess I’ve fallen prey to this line of thinking a few times in my life. Here’s what I’ve found, however:

First, the exact same laws of supply and demand apply that applied when I was sitting at that bar at SXSW in 99. So many people want to work in the music industry, and so many of them have realized how broken it is, that they’ve all had the bright idea to start a music startup. SO there’s tons of competition, low valuations, etc.

Second, the music industry itself isn’t THAT big as industries go, so there’s not a ton of investor temptation for these startups.

And third, like many things, it’s an insiders game. Look at the big wins in music lately — Beats, Spotify. These things weren’t started by scrappy outsiders. This isn’t an industry where the young outsider can win big. Sure, they can destructively disrupt the thing (think Napster) but any money is gonna be made by insiders.

Reading your email, I think you’ve sort of hit the nail on the head. You seem to be at a crossroads. It seems to me you could go all in and give everything to your album, or you could let it take a bit of a backseat and go make some money and put that money towards your “art.” I can’t really answer that, but i do think it’d help you to decide which one is going to be your “career” for the next few years. Not necesarily forever, but for, say, the next 3–5 years. Are you going to be an artist, 100% all in, or an entrepreneur that has a hobby in art?

(The “investment” is a wrinkle I can’t advise on. It’s not clear to me what you took it for, from whom, or what they’re expecting. There’s a bit of a world of artists taking “investment” these days (Google “Jakob Lodwick and Francis and the lights”) but not much. I guess my advice would be to put the investment aside, make some larger decisions, then deal with the investors as necessary.)

Anyhow. It’s hard to look back on your life and ask yourself if you did the right or wrong things. I’m very happy in my life now. I know if I decided to go “all in” on art, it would be very different. Would it be better? Worse? I don’t know. I do know that there was no half-waying it, though. At that moment in my life, I needed to decide which path to took. I think the one I took has been quite an adventure.

I know this probably isn’t super helpful, but there it is. Hope you take something out of it.

r.

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Rick Webb
Rick Webb

author, @agencythebook, @mannupbook. writing an ad economics book. reformed angel investor, record label owner, native alaskan. co-founded @barbariangroup.