Meet Jon Gilman | Artist Development Strategist | DJ & Producer

We had the good fortune of connecting with Jon Gilman and we’ve shared our conversation below.

Hi Jon, what was your thought process behind starting your own business?
From an early age I knew I wanted to run my own business. I studied entrepreneurship in college but I wasn’t sure exactly how I was going to get there. I was programmed that I had to go to college, get a job, etc. But I found the most joy in what I was doing outside of my 9-5: managing projects in the music space and even developing a career as an artist myself. I started a music blog and ran it for 10 years, I began DJing and producing music, I started throwing my own events, managed half a dozen artists, and was an A&R at two independent record labels.

I was mostly happy in my career in Tech Sales until one day I woke up and realized it wasn’t it for me anymore. I was super grateful for the success I had, but after 15 years it wasn’t fulfilling anymore.

I spent a couple years trying to figure out what I really wanted to do. I knew I wanted to work in music full time, but every attempt I made didn’t work out.

So after traveling the world, trying and failing at an Amazon business, attempting one last go-around at an early-stage startup, I decided to shoot my shot at my own business.

I realized so many artists had been coming to me for advice in the music space over the years, I decided to see if they wanted to work 1:1 with me to help them develop a strategy to grow. I posted a video of myself asking this question, and within a couple weeks I had my first paying clients.

This realization that I could help artists and do it on my terms led me to really put my all into building my artist development agency, which is now one year in.

It’s been challenging, but rewarding, and I’m so bullish on making this a success.

What should our readers know about your business?
I am one year into running my business called The Racket House. This is borrowed from my artist name which is Racket Club, because I enjoy playing tennis and I jokingly “cause a racket at the club” (as a DJ). Originally TRH was started as an artist management and event production company, but I pivoted last year when I decided to turn it into an artist development agency.

The first year has been challenging, but I’ve learned a ton. Learned about myself, the industry, the market, what it’s like selling services to artists, and so on. It’s not like selling software to multi-billion dollar global corporations. I’ve had to soften my approach and lead through education. All the while having to combine overcoming imposter syndrome with figuring out how to actually make money doing what I love.

My approach for this business isn’t one-size-fits-all. I don’t sell a course. I work 1:1 with artists to actually understand where are they are, where are they trying to get to, and what’s preventing them from doing that.

Despite falling out of love with my previous career path (enterprise technology sales), I actually learned a ton from that world. The consultative approach I took in that career, is what I use today in working with artists.

So, I help artists with a strategy to build on their success, and I also realized through conversations and surveys that not all artists want to work with me on a long-term basis. Some just want marketing help. So I began offering things like advertising services, playlisting, email marketing, social media, etc.

I also combine music and business, since I have experience in both worlds. I help artists think of themselves like a business and focus on branding, their product or offering, and how to market and sell themselves.

A lot of what I help with is around mindset and accountability – sometimes it’s just a matter of doing the work.

In 2025, being an artist means more than just focusing on the art itself. It means looking after every component of what makes the artist special and unique, and telling the world about them.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
Well that’s a switch-up! Definitely depends on the time of year. Summer vs. Winter in Colorado is very different. If it’s during the winter, we’re going skiing. Summertime could be hikes or camping and you better believe we’re going to Red Rocks for a concert or two.

Mission Ballroom hopefully has some good shows happening, because outside of Red Rocks that’s the coolest venue in the city.

My girlfriend works at Nana’s Dim Sum & Dumplings – so I’m biased because that place is a great place to eat. I’m also a big fan of Safta and El Five.

I love spending time outdoors so hopefully there’s a chance to walk, run, bike, play tennis and much more. There is no shortage of breweries in town either, so that’s always on the list!

Who else deserves some credit and recognition?
Where do I begin! In no particular order…
– My early clients for putting their trust in me
– Jake Clavette for pushing me to start and being there as a fellow entrepreneur
– Ken Hoge for giving me a place to call home in Denver, and a space to build from
– Alex Drachnik for her fellow entrepreneurial spirits and teaching me the ways of social media
– Malko the Promo God for being a fantastic business partner
– My girlfriend Brittany who I met early on when I moved to Denver last year and is a huge supporter of everything I do
– My parents, of course, who have supported me and my projects from day 1. Whether entering me into drum lessons or coming to see my DJ gigs
– The country of Guatemala for being an amazing place that I called home for a month last year, as I did a retreat to work on myself and my business
– The book The War of Art by Steven Pressfield. A friend shared this with me, and it resonated in so many ways. I now send it to many of my clients
– My collaborators in music and art, you know who you are!

Website: https://www.therackethouse.com

Instagram: @therackethouse & @racketclubbb

Linkedin: https://www.linkedin.com/in/jongilman87/

Soundcloud: https://soundcloud.com/racket-club

Youtube: https://www.youtube.com/@racketclubbb