Contests are weak. I can’t even be bothered to go to them anymore, let alone support them. Any why should I? Why should I support an event where only a fraction of the attendees are skating, and only a tiny handful of those go home as “winners”? No. I don’t want any part of those sorts of shenanigans. Everyone should be skating, all the time. Everyone should be a “winner”.

What I want to see, more than anything else, are free, all-inclusive, fun-for-everyone, grassroots skate events where everybody participates, and everyone has fun. And I want to see millions of ‘em, every week, all over the country.

We’re here to help that along. We’re gonna show you how easy it can be, and how it’s done.


From my first-ever grassroots skate event, where I played the role of organizer and host, left to right: Adam Richards coming down the line; the crew at Eldorado park; the flyer; Robert Rodriguez, 360 Boneless into the bowl at Eldorado Park.



There are lots of reasons. The adventure of it? Trying something new? Meeting new people, and making new friends? A great road-tripping excuse? Getting sponsored? Yes. It happens. Becoming an industry power player? Don’t laugh: a lot of our current industry heads actually started out as humble ramp owners and grassroots event organizers. Hell, the MESS (MidEast Skateboard Series) alone spawned about half of our industry bigwigs, for pete’s sakes. And that was just one contest series.

But by far, “having fun” is the biggest and the best initiative. If that’s all you ever get out of it, then it’s still way worth it.


“The MESS wasn’t about contests. Contests were a way to get ourselves organized, push each other, and get free stuff. The MESS was a way for us to take skateboarding in our own direction.”

           – Britt Parrot, from The Skateboarder’s Journal Lives On Board


The Biggest Risk

Believe it or not (you won’t), I’m pretty shy by nature. When I started doing events, my biggest fear was that nobody would show up, and I’d be a huge loser. I think that’s a pretty universal fear, and the universal result is that nobody ever does anything. If people could find the inner strength to put that fear aside, if only for a moment or two, then they’d probably accomplish some really cool stuff. I know I did. Getting over your own uncomfortable insecurities is a totally redeeming reward, all by itself.

If you’re afraid of the same sort of stuff that I was worried about, well, don’t worry. If I can do it, then you can do it too.


Photos from my first-ever Phoenix CitySkate event, left to right: Jo Nathan, Alex Dunning, and Andrew Borden; the flyer; the prize packs that we gave to every participant that showed up; the crew; drone shot of the crew heading downtown, photo by Jessie Pena. 



Get Creative, and Get Weird

What sounds like fun? A backyard ramp session? A street-skating session at the local schoolyard? A BBQ at the local skatepark? A bank/ditch excursion? A longboard cruise through downtown? A flatland/freestyle gathering? Ever wanted to try slalom? (It’s kinda fun!) Think outside the box, and don’t be afraid to do something different. Variety is the spice of life. So, live it up.

I’m a pretty lucky guy. I’ve lived a pretty good life. I’ve done all of the above at some time or another. But I wouldn’t have done any of it, without taking a little bit of initiative.


Pick A Venue

Don’t ask. Just do it. “It’s easier to apologize than it is to ask for permission”; that’s a really smart piece of advice right there. Okay, fine: if it’s a private, backyard ramp, then definitely ask for permission. Otherwise, go rogue and make it all way easier on yourself. Skateparks, schoolyards, cityscapes… these things are public domain. Be respectful, keep it tidy, clean up after yourselves, and keep it hush-hush, and you should be just fine.


Plan An Itinerary

Having a solid plan is the key to legitimacy. You don’t want to half-ass that part. “Meet at the park at 11, and bring some brats and beers” is a great start. Or, “meet at the ditch at 9 am, and bring a broom”. Don’t be shy about asking everyone to pitch in and contribute something to the cause. If they’re not total dicks, then they’ll probably be really happy to help. What kind of jerk hates having a good time…? Nobody I know.


Sometimes, I get super ambitious and plan two events, back to back…


How Much Does It Cost?

That’s always the big question. People think it costs hundreds or thousands of dollars to put on an event. That’s just not true; money isn’t as important as everyone thinks it is. Honestly? Some of the best events I’ve ever attended (or organized) have either been totally free, or pretty damned inexpensive. It’s really not about getting spendy. It’s all about having fun.

The weekly skate jams I used to host in Concord, New Hampshire way back in the ‘90s started out as free events; we’d simply get together every Friday night, skate the stuff at the schoolyard, and that was that.

Once I became a company owner and had a few bucks in my pocket, I bought a used pickup (for $500 from my intern), and built legitimate obstacles. I think I had about a grand in the whole project. But we did those skate jams week in and week out for almost ten years straight. That’s a damn good return on investment, right there. I skated about half my life away at those things. Best times I’ve ever had, for sure.

The events I do these days are still pretty cheap. I print off flyers at FedEx Office; that might cost me twenty bucks or so (at the most). I might buy a train ticket or a bus pass for the longboard cruises ($2), and buy myself lunch at the after party ($20?). Maybe a bunch of cheap plastic cups to use as slalom cones ($3 or so).

In the last three years, I don’t think I’ve ever spent more than $50 on organizing and/or hosting one of these events. It’s not nearly as expensive as you might think it would be.


Invite Everybody

Don’t be a douche. Don’t be a part of some weak cool-club clique. Invite everybody. Share the love. Trust me: you’ll get the love back, fer sure. You get what you give. So give it up, buddy.


…sometimes, I plan two for the same day. Phoenix participated in Michael Brooke’s “Roll For Peace” event by planning a morning and an evening roll, so everybody could be accommodated and nobody would have to miss out.


The Flyers

Digital media is a Godsend, and computers are easier to use than ever. You could probably do it even better than I can, and make a really catchy presentation. But there’s still a certain charm in the old-fashioned, hand-drawn flyer. Hell, even a photocopied scribble still works wonders. Try it. It’s not that hard to do. Take it to your mom’s office, and photocopy a zillion of ’em. Then, give them to everybody and hang them up everywhere.

As you can see, I put a lot of time, energy, and work into my flyers. It’s a mega creative outlet, and a labor of love that pays off. When Jim Gray messages you on Facebook and tells you how much he loves your flyer-style, you’ve sort of arrived.


Promote, Promote, Promote

Here’s a tip: social media is not the end-all and be-all of promotion. I did an interesting experiment last year with my events, and it taught me a lot. Half of my events, I promoted via skate shops and social media. The other half, I promoted via social media only.

The events where I only used social media attracted half the attendance, sometimes a quarter, compared to the shop-and-social-media-promoted events.

The lesson? Get your local shop involved. They’ll love ya for it. And you’ll get the love right back at ya.


The Prize Packs

At my events, everybody gets a prize. Just for showing up. Much like party favors, it’s a small token of appreciation for participating, and it’s super sweet. Be a good host. Hook everybody up, and thank them for coming.

They don’t have to be expensive. Michael [Brooke, at Concrete Wave Magazine] sent me boxes of mags to give away. A lot of companies and shops gave me stickers. Now, what kind of skater hates magazines and stickers?

Nobody, that’s who. The prize packs were really popular, and a super big hit. And best of all: they didn’t cost me a single dime.


The 2017 Weekend at The Wedge event saw heavy hitters (such as famed skateboard collector Daymond Dodge, and the illustrious Natalie Krishna Das) in attendance, mixing it up with the locals. Everyone had a blast. That’s the whole point.



Obviously, prize packs mean sponsors. Any skateboard company with a teeny fraction of a tiny brain should be more than happy to at least kick down a handful of stickers; if they’re not, then they’re not very bright. After all, they’re getting great, on-the-ground grassroots promotion and excellent PR (that’s short for “public relations”) out of it.

Many companies will even toss in some legit prizes. Free product, stuff like that. Have a raffle, or a mini product toss. Giving the product away to some kid that really needs it to keep on skating is also a really nice touch. If you’re super cool about everything, the sponsors may even kick in a little “thank you” present for the organizer. That’s a nice perk. Make sure you send them a thank you note, if they do. Class still counts in this world.

Don’t be shy at all about contacting these folks. You’re actually doing them a really big favor by inviting them along. These brands can’t be everywhere, all the time. Believe it or not, brands actually look to kids like us… well, kids like you… to help them promote their brands. Remember that.

If they decide to send along one of their regional sales reps to attend the event, and do a little bit of on-site promotion? Then, even better.


Go Full Swank

I like to put a lot of style spin into my events. Every time I do a longboard cruise, I plan a nice lunch at a swanky restaurant somewhere. Being a middle-aged adult with lots of middle-aged adult friends, we can do that sort of stuff because we have the means to do it. But kids can do it too, with a little bit of imagination and creativity. Your local skatepark is probably in a city park, with grills and stuff. Permanently “borrow” twenty bucks from your parents, raid the pantry for some fixin’s, grab that bag of charcoal out of the garage, steal a basting brush from your mom’s junk drawer, make yourself some marinade (you can find a great recipe in this month’s The Paupered Culinarian segment), and impress your friends with the best hot dogs ever. If your parents are supportive, they might even help. Everybody loves an ambitious kid, right?

Maybe if your local skate shop is cool enough, they’ll help you out with this sort of swank too. I’ve personally spent many an afternoon at the skatepark, flipping burgers and toasting buns. That’s kinda what skate shops are for, right…? To help the kids along, and bring them up right?


A Life Well Lived Deserves To Be Documented

Share the fun. Take lots of photos with your crappy camera, just like I do. Post ‘em up all over your social media. Send some in to Everything Skateboarding, and write a little article to go with ‘em. Let everyone know: if they weren’t there, then they missed out in a major way. Spread the stoke. Live life well, and live it up right. Savor the memories, and then do it all over again.