When I Grow Up: Becoming a Business Coach, Speaker, and Entrepreneur

Hey y'all! If you only read through email you may not notice, but there have been a few changes around here. I switched to a different Squarespace template yesterday. The template I'd been using was discontinued and I was starting to have some issues. The new look is a little cleaner and simpler, but I'd love to hear what you think about it!

Now back to the business at hand: introducing Jennifer Reitmeyer! She seems to be an incredibly busy woman, running not one, not two, but three successful businesses. 

When I Grow Up... Becoming a Business Coach, Speaker, and Entrepreneur


As a child, I wanted to be a ballerina when I grew up. I also told a reporter once that I wanted to be Madonna. Given my nonexistent singing and dancing talent, neither of these vocations were in the cards for me. Glad I’m good at improvising!

How close (or far) is your current career from that dream? Couldn’t be farther! But I was kind of a bossy kid, so it stands to reason I’d find a way to be the one in charge.

What is your official job title? I’m the president of MyDeejay, the founder and co-editor of WeddingIQ, and the founder of Firebrand Messaging. I also do quite a bit of small business coaching and some professional speaking under my own flag.

Ok, now what does that really mean? Good thing for me, being the boss in all my businesses means I get to come up with the titles and the actual job descriptions! In all seriousness, though, I consider myself the visionary, the leader, and the ultimate buck-stopper in everything I do. For MyDeejay, that means constantly raising and redefining the standard by which we provide music for couples’ weddings. For WeddingIQ, it’s identifying and dissecting important topics that are relevant to business owners in my industry. For Firebrand Messaging, it’s fulfilling my blogging and social media management clients’ need for authentic, smart content that sounds like they could have created it themselves rather than outsourcing it. And for all of these businesses, I’m constantly looking for ways to streamline my operations, improve my productivity and create a client experience that aligns with the brands I’ve created.

What is a typical day like? Some days I start by wrangling my two awesome little boys – they’re both quirky, interesting and neuroatypical – and getting them off to daycare. Then it’s off for a whirlwind of tasks for my various ventures. A typical day for me includes a mix of coaching meetings; preparing contracts, editorial calendars and content for my blogging and social media clients; writing for my business blog; working on new seminar presentations and workshops; managing the contractors who work for me (DJs, office staff, writers and social media managers); networking online and in-person; and dreaming up new ways to market my businesses – and then taking action on those dreams! On the evenings my kids are with their dad, I try to fit in some social time (happy hour is a gift from the heavens) with my incredibly fantastic circle of friends. My ADHD-addled brain is thrilled about the variety of things I get to squeeze into a given day, and I always feel challenged.

Photography by Amy Raab 

Photography by Amy Raab 

How did you end up in this career? I started out in the wedding industry, fresh out of college, 18 years ago. After spending a few years in catering sales and event planning, I ended up in a sales and marketing position for an entertainment company. It was there that I met my now ex-husband and former business partner, and we ended up creating a DJ company of our own. It’s mine now, and it’ll always be my first business love. I realized, though, that as someone who doesn’t actually work in the craft that I sell – deejaying – my true passion is in the actual marketing and operation of a business, and everything that entails. I created my wedding business blog to discuss those things with other entrepreneurs in my field, and from there, my side hustle of business speaking and coaching started to flourish. And it was a business coaching client who actually inspired me to start my blogging and social media company, because he didn’t like the company he was paying for those services. I’m amazed sometimes when I look back at my entrepreneurial journey and see how things kind of naturally fell into place – all by following my passions, identifying needs, and finding ways to fulfill those needs.

Photography by Kirsten Marie

Photography by Kirsten Marie

What kind of education or training did you complete for this career? I have a bachelor’s degree in communications, although until I started Firebrand Messaging, I don’t think that was directly relevant to anything I do (I don’t think it’s that relevant now - blogs and social media didn’t exist when I was in college!). I don’t have any specific training, either; I’m just a very quick study who’s picked things up along the way. Some would be horrified to know that my business motto is “fake it ‘til you make it” – but that’s huge for me. I believe we create our opportunities through having a mix of the passion to learn, the commitment to work, and the confidence to try. I wasn’t a business owner before I got a tax ID and launched a website. I wasn’t a speaker before I stepped onto a stage for the first time. I wasn’t a coach before I sat down with a client and convinced them I could help make their business better. Have I delivered on everything I said I could do? I think so. But I had to be bold enough to know I could, or I’d still be sitting in a hotel sales office somewhere, doing the same thing I was doing at age 21.

What advice would you give to someone who wants a similar career? I think there are two avenues to success. One is to think of something no one else has ever done before, and do that. Be the innovator. That worked for me to an extent with my business blog, because no one else seemed to be doing the same exact thing, for the same exact purpose, that I was. (That has never been, and may never be, a big moneymaker, though – innovation often requires creating a client base from nothing, because it’s on you to create the demand.) The other avenue, which I personally have found more lucrative, is to think of something someone else is doing, but doing poorly. Then do it awesomely. That’s worked with my DJ business and with my blogging and social media management service. By homing in on the shortcomings of other companies, I’ve been able to create a niche for myself and a unique experience for my clients. I think being aware of these two avenues is useful not only for entrepreneurs, but also for people who want to be invaluable in their jobs working for someone else. Find a new way to be great, or be better than anyone else in an already-defined role, whichever feels more natural and rewarding for you.

 Do you have any other career dreams? What do you want to be when you grow up? My number one dream is to be a MOGUL. People chuckle when I say that, like I’m not dead serious. But I am. I want to bring something meaningful and different and real to the wedding industry, and to the business world as a whole. My vehicles for reaching this goal are the businesses I create, the blog content (and eventually, the books) that I write, the speeches I give, and the way I treat the people I interact with. I want to inspire.

Photography by Kirsten Marie

Photography by Kirsten Marie

Any last thoughts or encouragement for others trying to decide what they want to do “when they grow up”? My encouragement is twofold. First up: be authentic in everything that you do. When you’re 100% who you are, then you don’t have to waste energy maintaining a façade, you have the opportunity to connect with clients and colleagues on a deeper level, and you get to truly own every one of your successes, because they’re as real as you are. Some people would say some of my interests and choices aren’t stereotypically “professional.” Lots of folks might frown about my  bold tattoos, or my passion for squeezing every bit of fun out of life that I can (there’s a reason I choose to be self-employed, after all!), or my “Macgyver mama” approach to single motherhood, which has no room for a lot of the trappings of nuclear families. That’s okay. By putting myself – my real self - out there, I’ve found “my people” both personally and professionally, and I truly believe my businesses are more successful, and more enjoyable to run, as a result. My other bit of encouragement is this: You are capable of doing everything you believe you can do, but no more than that. I mentioned before that I am an advocate for “fake it ‘til you make it.” Decide what you want to pursue and go after it with passion. When you’re focused on it, and you’re putting in the work, great things will happen, but lack of confidence is a killer. Self-limits are by far the most limiting of all.

Whew! Aren't you exhausted just reading about her day? I'm so glad she was able to take time out of her busy schedule to share her story with us. You can find Jennifer at WeddingIQ, Firebrand Messaging, and MyDeejay.

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