What Being a Deadhead Taught Me About Being an Entrepreneur

grateful-deadA post and the comments that followed on one of my favorite blogs, Marketing Hipster, really got me thinking about why so many people interested in marketing were also Grateful Dead fans.Are there really that many Deadheads out there that a post like this would draw out so many or are there a concentrated number of them that are now marketers and entrepreneurs?

The more I thought about it, the more I realized that being a Deadhead actually taught me a lot about business and about being an entrepreneur. Here are some lessons learned on the road while touring with the Dead back in the good ole days of the early 90′s:

It’s ok to be different

Most of us try to blend in, but let me tell you, when you walk into a grocery store in some little town in Ohio in a patchwork dress, reeking of patchouli, and not having showered in 3 days, you don’t easily blend in. Most stared with disapproving looks, but other would stare with take me with you eyes and stop and talk for hours, wanting to know all about where we came from, where we were going, and why we did this. These are the kind of people that could become friends for life the kind of people you could call the next time you rolled through town for a place to crash for the night. As John Wesley so wisely states in his post titled 27 Lessons Learned on the Way to 3000 Visits a Day and 2200 RSS Subscribers, you’ve got to piss a few people off to build a strong following.

A strong community is powerful

Building community is a big buzz term in internet marketing these days, but the Dead were masters of building community starting way back in the 60′s. I’m not sure if they set out to do this, but it happened for sure. The Dead brand became synonymous with a lifestyle. Instead of selling one ticket to just locals for the show in their city, having a community of fanatics meant that they were selling a whole tour full of tickets to individual Heads that would stop their lives and follow them from city to city every summer.

Good marketing doesn’t need to be expensive

With nothing more than a piece of cardboard and a Sharpie marker, you can sell just as many grilled cheese sandwiches in the parking lot as someone with a flashy professionally made sign.In fact, you would probably sell more.

Package up products and services and offer discounts in bulk

One burrito for $3 or 2 for $5? No doubt the $5 sales were more prevalent. It’s easier for 2 people to come up with 5 bucks than for one person to come up with 3. (I know, $3 doesn’t sound like a lot, but when you’re broke and on tour, it can be! This is a lesson in understanding your demographic!)

Give away something for free

If you’ve ever been to a Dead show, you’ve no doubt seen the double decker maroon bus driven by the Yahweh’s. This was a religious group that tried to convert hippies to come aboard. They were smart marketers. They offered free medical care in the form of band-aids, gauze, etc to anyone who got hurt on the parking lot. Once you were on the bus, you were a captive audience for the pitch. Plus, they had already taken care of you in a time of need which further enforced their message.

Be kind to other people

When you’re living on the road, being kind to other people is essential because you really do need the companionship and occasional help from other people to survive.Not all hippies are great people.Those who did bad business in the lot were ostracized by the rest of the community.If you wanted to do good business on the parking lot, you had to do right by others.

You can get by even with a sporadic income

Most people resist taking the plunge into entrepreneurship because they can’t handle the thought of not knowing when they’ll get paid next. I sold dresses and jewelry on the parking lot. Some days were good, some weren’t. At some point I ran out and literally sold the clothes out of my backpack at a show in Shoreline CA. When I set out on the road, I had no idea how I would get by, but I did. Things just have a way of working out.

Make it easy to share your content

If the Dead were still around today, they’d still be profitable even though most of the world is downloading music for free. Why? The Dead always allowed tapes of their music to be free in fact, they encouraged it! Every show had a special section for tapers and their recording equipment. They were able to record the shows as long as they only traded or gave away the tapes. As a result, most Deadheads had boxes and boxes of tapes from hundreds of different shows that they listened to non-stop, deepening the love for the band and the lifestyle even more.

It’s ok to have fun

If you’re not having fun in your life, what’s the point? When you do something you love to do, life is so much more fulfilling.

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