The Dirtiest F-Word In Business: Highlighting My Failures As An Entrepreneur

A few weeks ago, I shared an episode about how Morgan Wallen sold out his music festival, Sand in My Boots, in under two hours, simply through the power of branding. I also released an episode exploring Post Malone’s successful transition into country music. Both artists were headliners at the festival, alongside Brooks and Dunn, and each one showcased powerful lessons in brand development, resilience, and career transformation.

But what truly struck me wasn’t just the music. It was the stories behind the stages and the way branding and storytelling collided in real life.

From Song Titles to Festival Zones: A Masterclass in Immersive Branding

Held on the beaches of Gulf Shores, Alabama, The Sand in My Boots festival was more than a concert. It was a full-fledged brand experience. Morgan Wallen’s team cleverly integrated song titles into immersive spaces throughout the festival:

• 98 Braves Park
• This Bar (a real bar at the event)
• Spin You Around Ferris Wheel
• Love Somebody Lane: an actual spot where multiple couples got married (or at least mock-married)
• Flower Shops: a themed floral stand for wedding bouquets

Every element of the festival was dripping with intentional branding. It was fun, on-brand, and wildly creative.

Music, Marriage, and Memories

It had been over a decade, since around 2013, that my husband Caleb and I had attended a music festival together. This one was packed with an eclectic mix of performers: Bailey Zimmerman, Cameron Marlowe, Ella Langley, Riley Green, Chase Rice, T-Pain, Three 6 Mafia, Diplo, and 2 Chainz. I’m probably forgetting a few, but those are the acts we made a point to see.

As exciting as the performances were, the true magic came from hearing the artists’ stories, the moments between songs when they talked about their journeys and shared the turning points in their careers.

The “One Song” That Changes Everything

More than once, we heard an artist say, “This is the song that changed my life.” Cameron Marlowe talked about writing that pivotal song from his bedroom in Kannapolis, North Carolina, completely unaware it would become the one that transformed his future.

That resonated with me deeply. I thought, How many “songs” have I written in my business that felt like failures but were just stepping stones?

He likely didn’t know whether that song would be a hit. But he kept going. That’s where the inspiration lies.

The Dirtiest F Word in Business

And that brings me to the “dirtiest” F word in business: Failure.
(Not the other F word, which I do love, but try not to say on this podcast in case my kids ever listen back.)

This idea of failure has been on my mind, especially after a recent interview on the Built From the Ground Up podcast hosted by Gwen Tinsley. Gwen, who also happens to be my business and sales coach, runs a consulting company called Grit & Tenacity. She focuses on highlighting stories of female entrepreneurs who overcome challenges- stories just like mine.

When There’s No Plan B: Bailey Zimmerman’s Backup Plan

Bailey Zimmerman is a rising artist who sang a song titled Backup Plan at the festival. He introduced it by saying something that really struck a chord:

“If you have a backup plan, you’ll never achieve Plan A.”

One line from the lyrics still sticks with me:
“Falling down ain’t enough to change who you were born to be. Getting back up—that’s the only backup plan you need.”

Zimmerman shared that just a few years ago, he was working a blue-collar job in the oil fields. No music career. No backup plan. He simply asked God to show him the path because he couldn’t keep doing what he was doing. The clarity came, and he ran with it. That kind of determination to pursue Plan A—without a safety net—is terrifying but powerful.

Post Malone, Reinvention, and Radical Grace

Then there was Post Malone. I’ve wanted to see him live for years, and he didn’t disappoint. He was gracious and humble, thanking the audience after every song. He encouraged the crowd with this message:

“If you have a dream, go do it. Don’t let anyone tell you that you can’t.”

He’s not just someone who broke into the music industry, he’s someone who reinvented himself across genres. Few artists can do what he did, moving from rap to country with grace and profitability. That kind of brand evolution is rare, and it’s proof that belief in your dream. Plus a willingness to take big risks can pay off in a big way.

Stages of Success: From Side Gigs to Stadiums

What struck me most was seeing artists at every stage of their journey.

• Newcomers, playing in front of a huge audience for the first time
• Mid-tier artists like Bailey Zimmerman, on the rise
• Headliners like Morgan Wallen, celebrating a career milestone with his fourth album (37 tracks!) released the very day the festival began

The trajectory reminded me that success is not instant. Everyone starts small. Just days before the festival, I saw a video of Morgan Wallen performing at CMA Fest in front of ten people. Ten. And now? He’s hosting his own sold-out festival on the beach.

What’s on the Other Side of Resistance?

That’s why this episode isn’t about selling you something or convincing you that I’ve got it all figured out. It’s about telling the truth: We all struggle.

Morgan struggled. Posty struggled. I’ve struggled.

So let’s talk about it.

I’m going to share some of my biggest “failures” in business, starting with 2020—when I tried launching a program that flopped.

Here’s the premise: In the wedding industry, vendors often get one branding shoot a year, maybe. But with hairstyles, styles, and even business goals changing quickly, that annual shoot often ends up out of date. So, I thought, why not offer consistent, ongoing branding sessions?

With Be Your Brand, clients could book either monthly or quarterly sessions. I would coordinate full-day sessions at rotating wedding venues in Northern Virginia, where each vendor got a one-hour session. Eight vendors per day, different venues each month. It was designed to keep content fresh while doubling as a networking opportunity with venue owners or managers (who might add them to their preferred vendor lists).

It was a win-win-win:

• Vendors got high-quality, consistent branding photos
• Venues got exposure and reputable collaborators
• I would get predictable income and an efficient shoot-day system

Or so I thought.

The Beta Test That Bombed

In January, I hosted the first trial day, on my dime. I offered slots for free and even covered hair and makeup services. We had a full set: a baker, a fellow photographer, a hair and makeup artist… all on-site. I created welcome packets, curated a full experience, and made sure food and refreshments were available.

It went beautifully. I was convinced that my trial participants would convert to paying clients.

But February came… and only two people showed up. I’m honestly not sure either of them paid.

Then March 2020 hit, and with it, the COVID-19 pandemic. Everything came to a grinding halt. The weddings, the photography, the momentum. It all vanished.

After pouring time, energy, and personal funds into something I was passionate about, I had nothing to show for it. No recurring clients. No scalable program. That was what I considered my first big business failure.

I did walk away with relationships I still maintain today but those had started before Be Your Brand. And while the experience taught me a lot, it was a hard lesson to learn.

Pivoting to Passive: The Photography Framework Course

With the world shutting down, online education became the next logical pivot. So I jumped on board.

I created an online course called The Photography Framework—a comprehensive, 9-module curriculum for beginner and aspiring photographers in their first two years of business. It covered everything from business systems and marketing to gear management and portfolio-building.

Here’s what went into it:

I tested both Kajabi (which I found too expensive at $200/month) and ultimately moved to Shopify to host the course. I bought Amy Porterfield’s Digital Course Academy (DCA), which was a phenomenal resource for learning how to plan and sell an online course. I meticulously wrote every script and PDF.

I hired one of my former brides, who had launched a videography business, to film the entire course, an investment that cost me nearly $6,000. Altogether, I invested nearly $10,000 into this course. I launched in August 2020, right before our second son was born in September.

I followed all the launch steps:

• A timed open-cart/close-cart model
• Options to buy the full course or individual modules

And in return? I sold four total products, one full course and three individual modules, bringing in less than $1,000.

Reality Check: There’s Nothing Passive About Passive Income

I had believed the hype around passive income. Sell a digital product once, and you make money in your sleep, right?

Wrong.

Creating and marketing a course is a massive undertaking. Planning it is only step one. Recording it, hosting it, troubleshooting tech. It all takes time and resources. But marketing it to the right audience? That’s the hard part.

And here’s where I really went wrong:
My audience was filled with people looking to hire photographers, not photographers looking to grow their business. My content, my messaging, my brand were not aligned with the product I was selling.

There was nothing passive about it and it flopped.

That was my second business failure.

The Kentucky Property: A Dream Turned Nightmare

Then came the big one. The most expensive, most emotionally draining business failure of them all: the luxury wedding venue that never happened.

In 2021, we bought a 90-acre property in Kentucky with help from family. The vision was grand:

• A 6,000-square-foot main house for bridal party accommodations
• A 1,000-square-foot guest house for the honeymoon suite
• A 5,000-square-foot metal shop to be converted into a stunning event space

It was going to be a full wedding weekend venue. FromThursday check-ins, rehearsal dinners, Friday prep, Saturday weddings, to even Sunday brunch. An immersive, luxury experience.

But the neighbors had other plans.

Though the county was initially on board, our neighbors were not and they made their opinions known. They disrupted our peace with loud music and four-wheelers. They pushed back against every zoning effort. Eventually, the county, responding to neighbor complaints, issued a permit with 18 separate restrictions.

Eighteen.

Even the most diligent, perfectionist venue owner would have struggled to comply with every single one while hosting upscale events. The dream we had spent so much on—$1.5 million for the property alone—was slipping through our fingers.

Despite our grand plans and bold investment, the luxury wedding venue in Kentucky never came to fruition. After months of battling neighbor opposition, navigating restrictive zoning regulations, and watching our vision dissolve piece by piece, we pivoted.

We transitioned the property into a short-term rental listed on Airbnb. That was nearly three years ago, and today, it runs successfully. Thankfully, the once-resistant neighbors have largely calmed down, which has made operating the property far more manageable.

Mourning the Dream: Letting Go of a Long-Term Vision

Letting go of the wedding venue dream was more than a business decision. It was an emotional reckoning.

We had mapped out a 10-year vision for this property. It was going to be our forever home, where we would raise our kids, build a micro-distillery for exclusive wedding events, and eventually develop multiple Airbnbs. We envisioned hosting couples who could choose a custom barrel of bourbon, creating an unmatched guest experience on this unique, expansive 90-acre estate.

Letting go of that vision wasn’t just disappointing. It was heartbreaking. That time period, when we realized the wedding venue would never happen, was deeply tumultuous and filled with grief. Even now, years later, I still find myself processing the loss of what could have been.

The Weight of Guilt and the Fear of Failure

The hardest part wasn’t the zoning restrictions or even the wasted time. It was the guilt.

I had to call the family member who had helped us purchase the property and tell her the truth: it wasn’t going to work. I carried an overwhelming sense of failure. Believing I hadn’t done enough research, hadn’t been prepared enough, and that I had been naive for thinking I could pull off a project of this scale.

Imposter syndrome crept in: Who did I think I was?

That moment, more than any other, became the defining point of what I still consider my biggest business failure.

One More Pivot: The Real Estate License That Led Nowhere

Trying to avoid high real estate commission fees, I decided to get my real estate license in Kentucky so I could list the property myself. But that path came with its own challenges.

I quickly learned that I needed to be associated with a licensed brokerage in order to practice and it wasn’t easy finding one who would let me join just to sell my own home. Eventually, I found someone willing to let me hang my license, but the experience was isolating. I received little guidance and had no real strategy for marketing the property, which needed to be positioned toward out-of-town buyers—people from California, Chicago, or even Louisville.

Local buyers simply weren’t likely to have the resources for a $1.5M, 90-acre property.

We had two inquiries total. One seemed promising, but the only time they could view the property was during a weekend when it was occupied by Airbnb guests. We couldn’t show it and we never heard from them again.

Eventually, my broker stopped practicing, which meant I had to either find another one or let my license lapse. Already discouraged and feeling like I wasn’t doing the property justice, I let the license go inactive. I didn’t have the energy to pursue it further.

Finding Peace in the Pivot

Today, we still own the property, and it continues to run as a thriving Airbnb. While it’s not the luxury wedding venue I once dreamed of, it has become a steady, profitable part of our lives.

There are still moments where the sting of failure lingers. Reminders of what could have been. But with time and perspective, I’ve come to see these so-called failures not as endings, but as redirections. They’ve taught me more than any traditional success ever could.

And through it all, I’ve learned this:

Failure doesn’t define you. Your willingness to adapt, persevere, and dream again does.

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