Like kites without strings and butterflies with wings, my mother taught me to soar with my dreams.

Saying that my summer of 2016 was rough is a massive understatement. If you have lost a loved one, you can relate. To remember sorting and organizing all of my mother’s things and our family’s lifetime of memories still brings tears to my eyes. Crying so hard that you can’t eat or sleep until it literally makes yourself sick isn’t fun. There were times that I wouldn’t leave my house for over a week because I was so devastated.

Honestly, being isolated in my house wasn’t bad because the second I would leave, I would run into someone for the first time since – and making eye contact with them was enough for me to start crying again. My parents were married for 36 years and had 4 kids that were on every sports team in the Lexington area. Running into an assortment of our family’s dear friends anywhere I went was more bitter than sweet. I don’t mean to insult anyone who knew or loved my mother. I appreciated the condolences, but I could only take so many reminders. I missed living in a huge city with 4 million people who had no idea what had just happened.

There were lots of times that I wanted to say, “Fuck this. I’m running away.”

I had to get out of Lexington. Thankfully, the music gods were expecting me. I had purchased tickets to a couple music festivals in early spring, and I needed to escape my current state (mentally and geographically) more than anything.

In late June and early July, I went to Electric Forest and Forecastle Festival. I didn’t go to either of these events with the intention of selling jewelry. I was there for the music, to clear my head and to dance my ass off with my best friends. You know, be “normal”. To my surprise, my home-made accessories that I had taken to wear were purchased straight off of my body.

At Electric Forest, I remember getting ready each day in our group campsite. It was 40 people strong, made up of friends and the people who were soon to be friends. All of the girls would get together before going into the festival grounds. We made flower crowns, braided each other’s hair, and bedazzled our faces while planning the next time we would all meet at Front Row Center.

I happened to have my treasure box of feather jewelry. While I would accessorize, other people in my camp site would comment on the pieces I had brought.

“Oh wow, I love those, where did you get them?”

“I made them.”

“Where can I buy them?”

“Uhhhh, here?”

On my second day there, 2 girls (who are now good friends of mine) complimented and bought earrings too. As it turns out, they happen to run a “little” Chicago based blog called “Once Upon A Dollhouse” @

The same thing happened at Forecastle Festival. One of my girlfriends coordinated the trip, so I didn’t know the other two girls that we would be sharing a hotel room with. By the time we left they were customers, but better than that, they were new friends.

Kentucky Gypsy Lisa Brester Butterflies | Wings

As the chaos of summer was coming to an end, I had a very memorable conversation with an old friend. He happened to have a family emergency that suddenly brought him back to Kentucky. It was all too familiar. There was something so calming about being around someone who I could relate to, for the first time in months. I had faced many of the same fears, not so long ago.

I knew firsthand what it was like to need friends around, simply just to BE. So one evening, I went over to visit. We chatted about what we had been doing prior to returning home and the conversation flipped to my current job situation (or lack thereof). I told him about my renewed passion for making jewelry and mentioned that I had recently sold some at a festival.

He’s a successful serial entrepreneur, so he replied with several simple questions. “What are your material costs?” “What’s your average production time?” “How much did you sell them for?” With each response, I watched the lightbulbs go off in his head as it became clear what I could do. Suddenly he asked… “What are you doing with your life?”. Finally… it clicked.

It was time to further myself as a human being and become a human doing.

On August 1st, 2016, I took my first step and purchased the domain rights for my business,

Also around this time, I was contacted by a friend and former project manager in Los Angeles. She offered me a package of jobs that would require me to fly to Las Vegas and Los Angeles every 2 months to oversee and manage several vendor booths at major trade shows – including WWDMAGIC. There was no question that my stars were aligning and this opportunity proved to be a major puzzle piece in defining exactly how Kentucky Gypsy would thrive as a brand.

Kentucky Gypsy | WWD MAGIC | Wings

But even with the stars aligning, I knew I had work to do.

August 1st, 2016 – Started the logo design process

Kentucky Gypsy | Megan Somerville | Wings
August 27th, 2016 – Produced first product photo shoot in Los Angeles
Photo credit: Jaime Anderson @

September 27th, 2016 – Launched Instagram business account @kentuckygypsy

Kentucky Gypsy | Fox House Vintage | Wings
October 14th, 2016 – Displayed in first boutique – Fox House Vintage in Lexington, KY.
Kentucky Gypsy | Logo | Wings
December 9th, 2016 – Finalized logo and ordered business cards

December 14th, 2016 – Launched Etsy Shop

Kentucky Gypsy | Rachel Brann | Wings
February 26th, 2017 – Produced first editorial photo shoot
Photo Credit: Efren Beltran @
Kentucky Gypsy | Serendipity Earrings | Wings
March 8th, 2017 – Fulfilled first wholesale order – Serendipity Boutique in Lexington, KY

Kentucky Gypsy | Serendipity Chokers | Wings

March 20th, 2017 – Featured in first publication  – Kentucky Kernel’s Spring 2017 Fashion magazine, KRNL @.

Kentucky Gypsy | Made LOCAL Market | Wings
May 13th, 2017 – Debuted as a vendor at first open-air market – Made LOCAL Marketplace – Cincinnati, OH.

July 18th, 2017 – Launched personal WordPress blog

August 1st, 2017 – Happy One Year, Kentucky Gypsy!!!

Rome wasn’t built in a day. Kentucky Gypsy is a constant work in progress.

Embracing the flow will always be a challenge because a lot of this is new to me.  Each day, I get better at overcoming the obstacles I encounter. I beat myself up a lot. “I guess I don’t want it badly enough.” “This should be done already.” “I should have done that differently.” My to-do list is miles long and my priorities become skewed, sometimes without my permission. Like everyone, I’ve got my share of distractions, but sometimes I’m just not motivated. You have to give yourself a break. During these times, I remind myself not to force things.


“If you have to force it, leave it.

Relationships. Friendships. Yoga poses. Perfect Pony Tails.

Let that shit go!”

All things considered, my first year as an entrepreneur hasn’t just been about selling jewelry or scoring likes on Instagram. I’ve been focused on growing as a person after losing the most important person in my life. This business has helped me to stay productive and maintain a positive attitude. I personally value developing a product that I believe in, collaborating with others, and being genuinely excited about what I’m doing. I consciously follow my chosen purpose to create something that matters to me.

Kentucky Gyspy | Handmade Jewelry | Wings

In hindsight, my business has been an incredible coping mechanism for my grief. Even as an expression of my grief. After all, each piece I design, photo I produce, or sale I make, is a result of my mother’s love and encouragement for which I am eternally grateful.

It is now when I recognize what Kentucky Gypsy really means. Rooted in the south, destination unknown. Wanderlust. A free spirit. I want to travel the world. I am like my gypsy stars, aligning from time to time but always constantly moving. No matter where I find myself, I frequently visit the magical far away places that are in my thoughts and color my imagination.

Like kites without strings and butterflies with wings,
my mother taught me to soar with my dreams.

Kentucky Gypsy | Mom and me | Wings