My Embarrassing Business Stories

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If you look at my business today, it might seem like I have it all together. But when my business first started (not that long ago,) I made plenty of mistakes. And they were whoppers. 

Have you ever asked for a $100,000 loan? 

I have. Not my favorite memory. 

I had always wanted to own my own business. I imagined creating my own hours, giving myself the day off to stay home with a sick kid, and spending summers traveling with my family. 

When I got the chance to buy a wedding rentals business, I jumped at it. I thought, “THIS is my chance!’”

Isn’t it funny how things never turn out the way we planned? 

In 2014, I realized my business was failing. It was bleeding money and sucking my energy. My infant daughter barely recognized me, preferring my mother who had become her primary caretaker.  I was working sixteen hour days at the studio, coming home exhausted, but laying awake at night trying to figure out how to pay my employees the next day. 

Can anyone relate? While I’m hoping the answer is no, I’m guessing too many heads are nodding. 

What do you do when your biggest dream in life turns into a nightmare? 

I knew exactly what I had to do, and it required me walking into a bank and asking for $100,000. 

I knew how to save my business. I needed education, and I needed time. 

I did the math. If I could convince the bank to give me a $100,000, then I could afford to keep my employees, make my studio’s mortgage payments, and invest $40,000 in the education I so desperately needed. 

I was convinced that if I spent the year meeting with business coaches, attending workshops, and studying from the best corporate minds I could find, that I could make this business work. 

I knew I had the ability, I just needed the know-how. 


So I walked into a bank in Conway, Arkansas, and I explained all of this to the loan officer. For some reason, he approved my loan. I don’t know what convinced him, but that loan officer will forever get an annual Christmas card and a phone call from me. 

The rest of that year, I absorbed all the information I could. I learned how to pull up my big girl pants and treat my business like a business, not a hobby. 

Instead of going into Target for a vase or some pretty tissue paper and coming out with a shirt for myself, all paid for by my business, I created completely separate business and personal accounts. I learned how to track my money and make real profits. 

Instead of working sixteen hour days, needing to be available to anyone and everyone, I set specific office hours, bought a business phone, and picked a specific time each day that I check my email. I learned how to set boundaries and get more done in less time. 

Instead of finding work to give to my existing employees, I defined roles I needed to fill and tasks I needed to delegate, and picked employees with strengths that fit those roles. I learned how to create a strong and efficient team that freed me up to do what I do best.

I knew I was building the foundation my business needed to survive and thrive. With all these changes happening behind the scenes, I knew it was time to make the internal change external. It was time to rebrand and relaunch, and show the world that my business was here to stay!

Two weeks after the relaunch went live, I got the surprise of a lifetime: 

I found out I was pregnant with twins. 

You might be thinking, “Surely we’re nearing the end of this saga. Surely it can’t get any crazier from here.” 

You’d be wrong. 

The relaunch worked. I started booking bigger budget clients, kept implementing all I’d learned, and we were actually profiting. 

I survived the twin pregnancy (barely. Seriously not my favorite time). I delivered my healthy baby boys in June 2015. 

Two months later, the unimaginable happened. 

My husband, Brian, was in the hospital fighting for his life. 

With Brian in the hospital, I knew deep in my gut that even if he survived, life would never be the same. 

I was right. Brian made a full recovery, but he didn’t return to his finance job-- a job that had caused the stress that eventually ate away at his body. 

So there I was, two months postpartum, with a recovering husband, taking care of my three children and financially supporting my entire family just months after a business redefining rebrand. 

The pressure was on. 

Just a year earlier, I had faced bankruptcy. While things had improved over the past year, I knew that now, I really had to make this work. It wasn’t a game anymore; it wasn’t a hobby. My business was the one way we could support our family-- put food in our bellies and clothes on our backs. And with a little girl and twin boys, I knew we’d soon be going through both clothes and food pretty quickly. 

I kept producing weddings, but over the next few months, I had a gut feeling that I had to make another shift. I didn’t know exactly what it would lead to, but I couldn’t ignore the constant nudge, the small voice in the back of my head that whispered “tell your story.” 

Finally, I told my operations manager and right hand woman, Kellie, “Kellie, I think I’m suppose to share my story. Everything. What I did right, what I did wrong, my systems, my sales process. Everything. To help other business owners avoid all the mistakes I made. What do you think?”

“Let’s do it.” 

Once I decided to write a course to help business owners avoid all the mistakes I’d made, Kellie and I figured out what we needed to do to launch this course. 

I can’t emphasize enough: we had no idea what we were doing. 

I took charge of the writing and tasked Kellie with learning Adobe InDesign so she could create the graphic elements of the course. We figured out how to host webinars and create a locked PDF. 

We worked hard. We did our best with the tools we had. All along, my goal was to satisfy the small voice that kept whispering, “Tell your story.” 

I thought this would be a one-and-done type thing. I thought if we helped only one person, it would be worth it. 

By the time I finished writing the course, it had everything. 

  • How I attracted my ideal clients who would trust me and pay me what I’m worth

  • My sales strategies and processes

  • Sample flower orders and pricing guides

  • Email templates to systemize inquiries, client contact, and surveys

  • The exact details of how I handle sales goals, profit margins, and budgets to ensure that I’m profitable every time. 

  • How I hire, how I fire, and measures I take so that I never have to fire again

  • CONTRACTS, contracts, contracts

  • How to expand into wedding planning

  • How I efficiently run my business so my business doesn’t run me. 

I held nothing back. I wanted anyone who read my course to have everything she needed to avoid the pit I almost fell into. 

In 2017, we launched The Business Behind the Blooms. Before I knew it, Kellie was receiving daily emails from Bloomers (people who bought BBB) sharing exactly what they thought about the course. 

By early 2019, hundreds of wedding planners, photographers, and floral designers had taken my course. 

By trusting that small voice that told me to share my story, I fell right into my purpose: to help business owners create the businesses and lives they’ve only dreamed of. Just like I did. 

Because those dreams, they can become reality. Two years after creating BBB, and I spend my days educating people just like you. I create courses, resources, and content that teaches and encourages. I mentor, host workshops, and lead mastermind groups. I show up in inboxes, on Instagram, Facebook, and Pinterest. Most of all, I still teach through BBB.

And when I’m done, I go home. I snuggle my kids. I take Perry to drum lessons. Stella and I go to Disney World. I stay home with Zeke for a week when he has strep throat. I give myself a week off when Zeke’s strep throat makes me sick, too. 

I turned a nightmare into my dream life because I invested in education that saved my business, I trusted that I was ready and able to run a profitable business, and I did the work. I’m not special. I was just willing to invest time, energy, and money in the short term for long term freedom.

In the next few weeks, I’m going to be sharing four key tricks in my Business Spotlight Series that can transform your business so you can work less and make more doing what you love. 

Make sure you follow along. 

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Welcome to the blog

Hi! I'm Jessica Zimmerman, top wedding planner and floral designer.

Born and raised in Arkansas, I’m a proud wife and mama to a 5-year-old daughter and 3-year-old twin boys. A true believer in freedom, flexibility (and of course, incredible flowers), I’m wholly devoted to creating a life I love to live every single day–not just on the weekends. From travel to business to weddings, this blog is full of features designed to inspire other busy mamas (and businesswomen) to make a living from their passion without giving up their lives.

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Tune in to the Zimmerman Podcast!

AUG 8, 2019

Entrepreneurs Looking for More

Meet host of the Zimmerman Podcast, Jessica Zimmerman, as she shares what it takes to grow your business while living the life you love. To make sure you never miss an episode, hit subscribe now!


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