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Check Out Cole Coleman’s Story

Today we’d like to introduce you to Cole Coleman.

Hi Cole, we’d love for you to start by introducing yourself.
My, oh my, where do I begin? The beginning is as good of a place as any, I suppose. Let’s start there:

Born to a self-employed and entrepreneurial family, my parents owned a janitorial company. They cleaned car dealerships in St. Louis and the surrounding areas. From time to time, I would eagerly join dad on a portion of his path (which consisted of night shifts, vacuuming, cleaning bathrooms, dusting desks, cleaning glass, etc.), and would learn what it means to put in a bit of hard work (although I was likely more of a nuisance than a help). I remember hearing a few idioms from dad, including “Do it right the first time, and you won’t have to do it twice.”, and more importantly, the idea that “You’re never too good to get your hands dirty.”

Fast forward to my young teenage years. Hobbies come and go, with music being my most prominent. My sister and I were both homeschooled through high school and plugged into a co-op (a group of roughly 250 families and 500 students) where I would eventually meet my wife, Lauryn. My folks had changed careers from the janitorial company to starting in real estate sales, and the flexible schedule of homeschooling allowed me to practically shadow my parents during the workday and learn sales, and learn more about the real estate market which would be necessary for the coming years. Also during this time, a small DJ company asked me to join their business as their first additional DJ to handle overflow from them. I tagged along with them, learned the ropes, and worked with them for about a year, also DJing as the house DJ for my wife, Lauryn’s family’s wedding venue that they owned (convenient, eh?). At this point, DJing was a hobby and a side gig, but I never knew it would have become as large of a thing for me as it had.

In my senior year of high school, I started taking classes to get my real estate license. I took the test on my 18th birthday and failed, but I retook it a week later and passed! I hit the ground running with my new and exciting career, and started advertising. I’d take the money I would make from DJing at the venue and invest it into my real estate career. After months of beating down doors, showing houses, getting stood up for appointments, and only a few actually deciding to write any offers or sign a contract, I decided it wasn’t for me. I don’t suppose many folks trust an 18-year-old kid with something as large as a home purchase? I can’t say I blame them.

Oh well, onto the next thing!

Through real estate transactions, my parents had become familiar with a hard-money lender. It was perfect for a young kid with little legal credibility or liability, but a good business mind and decent presentation skills. A few papers signed, a presentation, a handshake, and a 13.75% interest-only note later, and I was on my way to finally making some money in real estate.

The real estate market at the time (2015-2017) was different than it is now. Then, I was able to purchase three homes that needed a crazy to fair amount of work for $23,000, $40,000, and $67,000, and put money and work into them and sell them for $103,000, $135,000, and $183,000, respectively, over a year and a half. Keep in mind that the profit isn’t the difference between these two numbers, but rather a number somewhere in the lower portion of that. A ton of additional money goes into these, along with a massive amount of work. We profited around $27,000, $4,000 (oops), and $36,000 across all three of these, which was amazing for a couple of kids. Lauryn, my now-wife, helped me with the repairs on these, as her father also did residential real-estate fixer-upper work. It didn’t seem odd to us, but looking back, I think it’s crazy that she was allowed to do that with me and even crazier that there isn’t a law against anyone under the legal drinking age to work on places that people live in. Either way, we did some very impressive work for any age.

Then, the real estate market started the climb, leading it to where it is today (barring a pandemic that choked inventory and sent prices sky-high). The prices went up as the economy improved, and a 13.75% interest loan became much more expensive on a $100,000 house than on a $23,000 house. I remember loading up tools and equipment from the last house we rehabbed and telling Lauryn that we should take the DJ company full-time. I think she finished my sentence because we both had the same thought. Over the next few weeks, we would hatch a plan to create one of the fastest-growing DJ companies in the St. Louis area, if not the fastest-growing.

So, back to the DJ stuff:

While we were dabbling in these other careers, we were always playing with the DJ gig We were constantly upgrading equipment, always learning and studying techniques and hosting, and performing any event we could get our hands on. We took any money from the DJ work and reinvested it into itself. We started advertising outside the home venue and added another DJ to handle the overflow. In our first year as a company, we would take 56 events. That year would be the start of what we then called “House DJ Services + Entertainment” as a touch-back to our roots as the “house DJ” of the venue.

We advertised like crazy, putting almost half of the revenue back into ads and marketing. Some things worked, and a lot of things didn’t. The way we looked at it, the waste was just the cost of education. We tried things, thought out of the box, and found our voice. We wanted to do something different than the rest of them in our field, and we found a message that resonated with our potential clients (and one we still repeat today): simplicity.

It’s the old idiom: “Keep it simple, stupid.” We saw that weddings were so complicated and so stressful. Looking at it from the clients’ perspectives, there are so many *chains* of decisions to be made when planning an event.

We instead decided we would invest heavily in the nicest equipment we could afford, include additional ambiance lights, and not charge a dime for anything other than time. This resonated with our clients and made booking us so frictionless. It wasn’t hard and didn’t require an Excel sheet to quote, just a start and end time. Everything was made easy (even for us), and we just gave and gave and gave. This treatment turned into countless referrals, dedicated fans, and amazing reviews. This culture of “give more than you take” even spilled over into the employees we hired. We found people in the real world who we thought looked like they were giving their current activity their all. We would hire from all walks of life and all sources: a Realtor friend, a videographer we worked with, a venue manager/performer, a paramedic/former groom, a family member and former broadcaster, a father of a bride, and some dude we met on Marketplace to name a few. We’d hire them if they had a great personality and a hard work ethic. We gave them all the resources they would need, paid an excessive amount for training and wages, and provided them with the most excellent equipment we could afford. This sort of treatment was returned to us tenfold in how incredibly hard they would work to offer one-of-a-kind experiences to our clients. We started selling our personality and team, bringing them to expos, teaming them up on events, and giving them control over their style. The energy around this team was crazy, and we loved every minute of it, even as much as to start training DJs in Nashville, TN, to start booking multi-regional events. By January of 2020, we had over 270 events booked for 2020. It was madness, but we had the best team that made it all worth it. Immensely stressful, but oh, so much fun. Through all of this, we transitioned the name and brand from the wordy House DJ Services + Entertainment to House DJ St. Louis and eventually to House DJ. I serviced over 95 events/year for several years, learning at every event and honing my craft, even learning so much from our employees and sharing that knowledge.

Then, 2020 happened, and events went dark for a few months (90+ cancellations, $30,000 in non-contract-required refunds in 3 months). I decided to look at everything and our processes for a few months since we couldn’t do anything else. I looked at our booking and client portal and was somewhat unsatisfied with the flow. It was easy for clients to use but wasn’t super powerful for our tools. I looked online for solutions and realized that the existing solutions were either powerful but ugly or beautiful and not very useful. I spent a few weeks researching different solutions until I came to a conclusion I didn’t want to go to: I’d have to do it myself.

So, with four months off and a government-mandated quarantine, I dove in: 12-16 hours a day learning software development the same way I knew. I was obsessed with the possibilities and had way too much time on my hands. I dove straight in, learned everything I could, and then came up with a design and a wireframe (an ugly example showing a user’s paths). Then, I started coding it. So many struggles, fumbles, and learning, but I invested the time and built something I would be proud of. As dad always said: “Do it right the first time, and you won’t have to do it twice.” I found that I enjoyed the software side of things. I enjoyed its creativity and the freedom to do whatever you want to do, as long as you have the time and willpower to make it happen.

Many of our employees had to find other work during the pandemic, as we couldn’t sustain them. We were able to keep enough to service, but it really exhausted them, and we hated to do that to them, but we also couldn’t find anyone else to do it.
So, we hatched the plan, which would take us to today:
– Phase out House DJ and convert it to a namesake brand, consisting of just me. Sell a higher price-point, slim costs, and streamline processes further. Sell personality, talent, and experience (650+ events over a career) and open booking possibilities nationwide (with 30 events performed in Nashville, Dallas, and Chicago areas).
– Silently started a software company focusing on business management systems. Build a reusable core consisting of calendars, platform-hosted payments, invoicing, digital e-signatures, messaging, and client portals. Then, build tools specific to each business type, creating hyper-focused business management tools using the same core to assist with scale and speed. Start in the events space, with the experience, knowledge, and connections already there, and then move to real estate, naturally.

Right now, we’re nearing the public launch of our first software, Spin by Simple City Software for late Summer. Spin is a management platform for DJs consisting of messaging, online booking portals, contracts, invoicing, forms, playlist integration, and much more! I’m also currently handling multiple events per weekend myself, and we’re supporting some of our past employees who’ve gone on to start their DJ businesses with overflow business and referrals. All-in-all, it’s been a wild couple of years and a bang of a start to our twenties. I can proudly say that we’ve accomplished just about everything we’ve set out to. We’ve done it all right the first time, so we won’t have to do it twice, and we’ve never been too good or too proud to get our hands dirty.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall, and if not, what were the challenges you’ve had to overcome?
I can’t say it’s been a smooth road, but we’ve had a bit of a semi-charmed life, in a way. When something happens, and we’ve caught a headwind, we just go with the wind, and it blows us somewhere better. When the real estate renovation market changed, and we couldn’t find another house to buy, we decided to shift gears and focus on our other projects until it calmed down (still waiting for that). When I was forcibly split from the other DJ company in my teens, we invested in our brand. When we came up with some challenges with the second house we rehabbed, we kept moving, sold it for what we could, took our lumps, and then bought a third, which turned out to be our very best. When the pandemic hit, and we were all-in on events, we shifted, slimmed down, battened down the hatches, and moved with the wind. We went, made changes where we could, and planted the seed of the software company. Lauryn and I talk about and ponder this often. Some of the biggest obstacles we’ve faced have turned into our biggest windfalls just by simply following them and floating.

As you know, we’re big fans of you and your work. For our readers who might not be as familiar, what can you tell them about what you do?
Title: DJ Cole Coleman || Simple City Software
I’m the owner of Simple City Software and a wedding DJ with over 650 events in experience. With Simple City Software, I build business management portals with highly-specialized tools. We’re working exclusively in the event space but plan to scale to other industries in the future! Our platforms feature messaging, payments, calendars, automation, contracts, invoices, multi-level contact access, and others. With DJ Cole Coleman, I handle high-end events in St Louis and nationwide. I specialize in weddings but also enjoy corporate events! I bring a relaxed and professional MC and hosting style with high-energy mixing and musical talents. I love to incorporate throwbacks and play in the fringes, pulling out songs you may have forgotten about and getting a reaction from those.

Any advice for finding a mentor or networking in general?
Treat everyone with respect, always. The best way to network is to live your life and realize that the person you’re speaking to may be the one who has what you need. With events, for example, never disrespect any member of the staff. A good boss and decision-maker care deeply about their employees, even if not simply for human decency. If you can remember names and take the time to make each individual feel important, it’ll pay back in dividends. You never know when the busboy at a restaurant is the owner, filling in where needed. You’re never above talking to anyone, never too important to give someone the light of day, and you’re NEVER too good to get your hands dirty.

So, my advice?
Pre-bus that table before you leave lunch. Pick up the trash around the complex you live at so someone else doesn’t have to. Be of service to anyone and everyone. If universal karma doesn’t reward you, someone or something will.


  • DJ: $1,500 for 4 hours, $100 per add’t hour
  • Software: varies

Contact Info:

Image Credits
Trisha Shelley Photography, Lemons Photography, LLC, Kera Photography, Simple City Software LLC

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