The "Side-Step"

Why a slight detour might save your music career

I have a dear friend named Lindse…….no wait ……. let’s call her…. Windsey.

(Almost blew her cover there…)

My dear friend Windsey is a super-talented comedian who lived in Nashville when we first moved here a few years ago.

And Lind….. Windsey….. like all up-and-coming artists, was (at the time) struggling to get booked for gigs. As we all probably know, bookers are looking for experienced acts that can sell tickets, so getting your foot in the door as a new talent is often incredibly challenging.

One day at a friends birthday party, I was chatting with the Wind-meister (as I call her from time to time)… and she was explaining her plight and her frustration around getting booked for gigs.

So I did what I always do - I offered some totally unsolicited and unwanted advice.

“My dear Windy….” I said, “…. instead of begging to get booked for a show based on your name alone, why don’t you create your own show and pitch the concept direct to a venue?”

My theory was simple. Instead of approaching bookers and asking them to book Windey Schultz… she would approach the venue directly and pitch a comedy show that just so happened to be hosted by Windsey Schultz.

In just a few days, Windsey developed a brilliant idea for a new live monthly comedy show called “Comedy Date Night”… where three comedians would answer questions from an eligible bachelor or bachelorette - much like the old school dating shows with a comedic twist.

The show was hosted by Windsey and featured a 15 minute stand-up set from her at the beginning of each show… basically guaranteeing her a headlining spot every month.

Windsey brought the concept to a local comedy club. They loved the idea and they immediately gave her a shot.

Now - instead of having to get folks to buy tickets to a comedian they never heard of… we marketed the show as “a comedy event for those looking for love”. Here’s what the flyer looked like:

Nashville is known for being a bachelor/bachelorette party destination, so we did our best to target those groups with our marketing as well.

As folks came into the venue, we offered them a free drink in exchange for their email (to add them to Windsey’s mailing list), ensuring that we’d be able to re-target and re-engage anyone who bought tickets for future shows.

Windsey managed to sell out the very first show, collect a boatload of emails, and host/headline on her own concept.

Suddenly, Windsey went from asking to get booked, to being the one in charge of booking other comedians for the show… and within just a few months, “Comedy Date Night” got picked up by the biggest comedy club in Nashville…. Zanies.

It was at her Zanies debut that Windsey met a billionaire with a conscience, fell madly in love, retired from comedy, and now lives out her days in a ski lodge in Zurich.

(Ok she is still waiting on the billionaire….)

But what Windsey accomplished is what I am now coining as:

THE “SIDE-STEP” - a strategy that builds your career by lifting up your community rather than trying to simply get attention for yourself.

By creating a platform for other comedians to shine, Windsey was able to build her audience exponentially quicker than simply trying to market her own comedy.

And as long as Windsey was collecting the data on her attendees for each show, she was now able to build a relationship with them and build awareness for her own comedy career.

A true win-win.

HOWEVER…

There are a few key ingredients to a successful “Side-Step” that cannot be ignored, otherwise it will be a massive failure.

1. You actually need to care about the community (duh)

Executing a successful Side-Step doesn’t mean simply going through the motions. You have to actually care about lifting up and creating a platform for others to shine, and be willing to work your a** off to build it for them. Windsey spent an incredible amount of time building “Comedy Date Night” and ensuring that it was a legitimate opportunity for the comedians she featured. You cannot fake this. You cannot phone this in.

2. The “Side-Step” is not a quick fix

Compared to “overnight viral success”, the “Side-Step” looks like a lot of work for slow, methodical growth… and that’s because it is. Pursuing a Side-Step means eschewing the idea of overnight success and locking in to a long-term plan that can consistently build your audience and community. A successful Side-Step is measured in years, not pieces of content.

3. You eat last

The whole point of a “Side-Step” is to use your talent, connections, and drive to lift up others in the community. If you do a good job of that, eventually that will flow through to you and your career… but your cup is the last one to get filled. This means you truly need to detach from your ego and practice extreme patience.

Some more examples of The “Side-Step” in practice:

(By the way… if you haven’t deduced it by now…. Windsey’s real name is ACTUALLY Lindsey Schultz, and she’s an incredibly talented and hilarious individual that you can follow here. Thank you Lindsey for letting me tell your story and creatively abuse your God-given name ❤️)

But sweet dear Lindsey isn’t the only one putting The “Side-Step” into practice… here are some more examples of how artists are building their community instead of simply building their careers:

Abigayle Oakley is building a songwriting bookclub where registrants have one month to read a book and write a song about it. At the end of the month, everyone gets together on Zoom and shares their songs and stories behind them. It’s a way to invite people into the world of songwriting and encourage creativity and community.

Cole Ritter is leading in-person discussion groups in Nashville, TN where artists get together to talk about the industry, current issues, and ideas on how to work together to fix them.

David Baldwin is using his background as an ad agency owner and Creative Director to build a Substack that discusses the evolution of music branding… and objectively tests those concepts in real time with his band, “The Gumbys” (who just released their first EP! Go David!)

Michael Gilbride (hey that’s me!) I decided to build MAD Records shortly after I stopped promoting my own music. I figured I’d take 5 years to do everything I could to help others build their music career, and eventually I would return to making and releasing music myself. You can check out my music here if you haven’t heard it already.

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Now I know the “Side-Step” may sound like a lot of work… or that you’re moving parallel to your goal rather than towards it, but that’s actually the social media brain talking.

Real, sustainable careers require an engaged and loyal community. And to do that, you need to be willing to set your personal goals aside from time to time to build up others.

The results aren’t quick… or viral…. or overnight. But they are real.

I’m 2-years into my Side-Step… and it’s been the most fulfilling, challenging, and actually successful music endeavor I’ve ever pursued.

It just required a long-term perspective and a healthy check of my own ego.

Now… let me know below what YOU’RE working on, or drop your questions and I’ll answer them in the comments.

Long live good music 🫡⚔️

Michael from MAD Records

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