In every business owner’s path, there’s a moment when they decide to leave their current role and pursue their side hustle or passion full-time … taking the leap, if you will. While it looks different for most, an underlying theme of “trust your gut” rings true. These 14 Southern entrepreneurs share the moment they knew it was time and offer their best advice for those approaching their take the leap moment. Read on and prepare to be inspired!

Bailey Spaulding of Jackalope Brewing Company

Years in business: 7
Business description: Craft beer brewery based in Nashville, Tennessee

When did you know it was time to take the leap?

When I graduated law school, the timing was right in my life — and in the craft beer movement as well. Instead of calling it one big leap, I looked at it as lots of little steps, which included writing the business plan, raising money, finding a location and buying equipment. Before I knew it, I was starting a real business.

What is your best advice for burgeoning entrepreneurs?

Learn to adapt — nothing is going to happen the way you wrote it in your business plan, so don’t freak out about having to adjust. You’ll see adapting is part of the fun puzzle of running a business and isn’t something to fear.

Southern Entrepreneurs

Bailey Spaulding, owner of Jackalope Brewing Company

Tommy Mayfield of Wyndy

Years in business: 2
Business description: Wyndy is a mobile app that makes it easy for families to find, book and pay background-checked college babysitters.

When did you know it was time to take the leap?

We started Wyndy only after we had, among other things: (1) researched the size of the market we’d be entering; (2) evaluated the competitive landscape; and (3) conducted focus groups and interviews with potential users to understand the problems they experienced around babysitting and the ways they would like to see those problems solved.

What is your best advice for burgeoning entrepreneurs?

As a founder, investing in your health (physical, mental, spiritual and emotional) is investing in your company’s success. It’s easy to think that your personal well-being must be sacrificed in the short-term while you’re trying to build and grow your business. However, the reality is that founders who burn out after 12 months can’t deliver the returns that they or their investors want.

Southern Entrepreneurs

Tommy Mayfield, founder of Wyndy

Anne Siegfried of The George Gallery

Years in business: 5
Business description: A brick and mortar art gallery specializing in abstract and non-objective paintings, located in downtown Charleston, South Carolina

When did you know it was time to take the leap?

I experienced a “What am I waiting for?” epiphany. I had just come through a health issue and a divorce, and those experiences gave me the confidence to take on a new challenge. Besides the personal commitment to starting/running a business, I additionally saw a hole in the contemporary art market in Charleston. I felt like I had a different perspective to offer.

What is your best advice for burgeoning entrepreneurs?

Set realistic goals. We all want to be a huge success right away, but odds are it’s going to take time, energy, a lot of sleepless nights and money. Also, shut out the noise, unless they actually know what they are talking about. Just smile and nod. When you are lucky enough to chat with someone who has valid experience, pay attention and soak it all in.

Southern Entrepreneurs

Anne Siegfried, owner of The George Gallery

Matt Houston of Beachy

Years in business: 3+ years
Business description: Beachy is a B2B technology platform connecting the beachfront ecosystem. Beachy replaces the archaic paper-based business that is the norm on the beach and provides beachfront operators with the ability to digitalize operations, streamline accounting, capture data, drive revenue and take advanced reservations from beachgoers.

When did you know it was time to take the leap?

As a husband and father of two little girls, I was a bit more risk averse than most when it came to “taking the leap.” I made sure to validate the pain points we wanted to solve and the need for our idea before investing any substantial time or money. When the demand for the idea of Beachy grew organically, to the point that we were getting international requests for a technology that we hadn’t even built, I knew we were onto something. That’s when I started losing sleep. That’s when I could barely focus on anything that didn’t involve beachfront commerce. That’s when I knew to take the leap.

What is your best advice for burgeoning entrepreneurs?

When you’re truly innovating and building a new category, you need to be willing to incrementally take steps towards your goals. By doing this and listening to your customers, you can be agile enough to make adjustments on the fly based on the pressures of the market, even when it means your assumptions were wrong.

Southern Entrepreneurs

Matt Houston and his team at Beachy

Matthew Charette of MDC Group, LLC

Years in business: 16
Business description: We have local restaurants and bars in historic East Nashville. Our establishments are Batter’d & Fried, Beyond the Edge Sports Bar and Drifters. We have great BBQ food including vegetarian options and some great local (mostly East Nashville) live music.

When did you know it was time to take the leap?

I knew it when I got fired from my corporate job. It was a job that I loved, but it was bigger than my skill set (at the time). My friends said I should just open my own place … it was a dream I had. Opening my own place just seemed to make the most sense as far as in alignment with my skill set. It was scary, but I could not imagine going to work for someone else.

What is your best advice for burgeoning entrepreneurs?

Never stop learning, take the classes, read the books, do the work, be prepared. Find a support system, a group of entrepreneurs and advisors — some kind of community of like-minded people who are going through/have gone through it, too. The bigger, more important thing is finding people who will “challenge” you to learn and grow, grind and push yourself.

Southern Entrepreneurs

Matthew Charette, owner of MDC Group, LLC

Jacob Greer of 6th Man Movers

Years in business: 5
Business description: We provide affordable, comprehensive moving solutions for local, long distance, residential and commercial services in the greater Middle Tennessee area.

When did you know it was time to take the leap?

Honestly, I just so happened to find myself leaping (or rolling) into an industry that needed disruption – a disruption for better service and expectations. Nashville continues to have a major demand for moving services which challenges my personal and professional growth. 6th Man Movers has proven there is a customer base that appreciates my efforts.

What is your best advice for burgeoning entrepreneurs?

Stop what you are doing right now. Whatever it is, it can wait. Create a plan. If you have one, adjust it — no better time than now. Work the plan. Most importantly — stick to THE PLAN!

Southern Entrepreneurs

Jacob Greer, owner of 6th Man Movers

Gabrielle Friedman of Gabrielle Friedman Jewelry

Years in business: 4
Business description: Custom jewelry designed and handmade by Gabrielle

When did you know it was time to take the leap?

Once my children flew the nest and I had more time, my passion for creating jewelry intensified and blossomed; I knew I’d found my calling.

What is your best advice for burgeoning entrepreneurs?

Passion and organization are essential. Also, educate yourself as much as possible to grow your skills — learning from other jewelers and honing my craft has been essential. At the same time, don’t be afraid to think outside the box.

RELATED: 3 Southern Jewelry Designers You Should Know

Southern Entrepreneurs

Gabrielle Friedman, owner of Gabrielle Friedman Jewelry

Garr Schwartz of Garr’s Beer Co.

Years in business: 2
Business description: We are a beer company based in Franklin, Tennessee, that “gypsy brews.” We see ourselves as a “fringe company.” We work on the fringes of the host company utilizing excess capacity, but we don’t infringe upon their primary workflow.

When did you know it was time to take the leap?

Brewing beer was a hobby that started in 2005 that quickly evolved from the stove top to a very sophisticated home brewery. When people began offering to pay me for beer, I knew there was an opportunity to turn my passion into a business. In 2011, I decided to build my own brewery in Nashville. I left that company and formed Garr’s Beer Co. in 2015.

What is your best advice for burgeoning entrepreneurs?

Be prepared to utilize every skill and piece of knowledge you’ve ever acquired. Then expect to learn all the things that you wish you had learned and all the things that you didn’t want to learn. In the beginning, you do everything, but have the wherewithal and funding so you can focus on your highest and best uses as the company grows.

Southern Entrepreneurs

Garr Schwartz, owner of Garr’s Beer Co.

Leslie Embry of The Blowout Co.

Years in business: 6
Business description: The Blowout Co. of Nashville was Tennessee’s first salon dedicated to the quick and beautiful blowout. We focus on all aspects of styling, up-dos and makeup. Our goal is to make you feel beautiful. 

When did you know it was time to take the leap?

I went to a wedding in Santa Barbara, California, in September 2011, and had my first blowout at a blowout bar called Shine. Those 45 minutes made me feel beautiful, and I knew immediately that the women in Nashville deserved to feel the same way. I decided to leave a 12-year teaching career and open my own blowout bar when I got home.

What is your best advice for burgeoning entrepreneurs?

Follow your gut. I also believe that you need to work on your business and not in your business. You can get so lost in the minutiae of the day-to-day operations that you miss opportunities to help your business grow and scale.

Southern Entrepreneurs

Leslie Embry, founder of The Blowout Co.

Stephen Rose of The Peach Truck

Years in business: 6
Business description: We bring fresh Georgia peaches to peach lovers across the country. 

When did you know it was time to take the leap?

My wife and I were young and a little stuck. We wanted freedom, but I went to a 9-5 every day. We knew we wanted more out of life, so once we proved ourselves for one peach season, we decided to quit our jobs before the next season and go all in.

What is your best advice for burgeoning entrepreneurs?

Quit trying to figure out every step of the way before it’s happened. Get feedback from your customers, and figure out how to be the absolute greatest at your craft as humanly possible.

RELATED: The Peach Truck: A Sign of Summertime in Nashville

Southern Entrepreneurs

The Peach Truck founders Stephen, Jessica and baby Florence Rose | Image: Eliesa Johnson

Cheri Leavy and Whitney Long of The Southern Coterie (The Southern Coterie + The Southern C Summit)

Years in business: 6
Business description: The Southern Coterie is a resource for the entrepreneurial South, designed to offer a community of passionate business owners, makers and doers the opportunity to connect, collaborate and create both online and in person through our annual Summit events.

When did you know it was time to take the leap?

We started a blog and quickly discovered our community of creatives wanted to engage in person, so we launched our summits with the goal to help them grow their business endeavors.

What is your best advice for burgeoning entrepreneurs?

You won’t regret failures because those are lessons learned, but you will regret not trying! Take your idea and take action.

Southern Entrepreneurs

Cheri Leavy and Whitney Long, founders of The Southern Coterie (The Southern Coterie + The Southern C Summit) | Image: Kelli Boyd Photography

Patrick Hayes of 1767 Designs

Years in business: 4
Business description: 1767 is a fabrication and design studio based in Nashville, TN. Using quality, hard-wearing elements like centuries-old reclaimed wood, steel, hammered copper and handcrafted leather finishes, 1767 crafts made-to-order furniture, wooden wall art and custom spaces.

When did you know it was time to take the leap?

There’s really no good time to take that jump — just do it when it makes sense to you. Take that leap when it feels good, or take the leap when it doesn’t feel good, when it feels a little uncomfortable — do it anyway. For me, it happened to be about four months in, I had enough business to keep things running, and it gave me room to grow my business in other areas.

What is your best advice for burgeoning entrepreneurs?

Make sure that whatever you’re doing, you’re passionate about it. It takes really being passionate and truly loving what you’re doing — and believing in what you’re doing — to carry you through those harder times.

Southern Entrepreneurs

Patrick Hayes, owner of 1767 Designs

Susan Logan Huffman of Reliant Investment Management, LLC

Years in business: 32
Business description: Reliant Investment Management offers independent, fee-based investment advisory services tailored to meet the unique needs of its clients. Reliant is committed to long-term client relationships based on personal service, customization and direct communication.

When did you know it was time to take the leap?

It was important to me to provide investment services that weren’t available at the time. So when the right opportunity came along, I took a chance and created a firm centered on personal attention that allowed me to best focus my efforts on my clients and their investment needs.

What is your best advice for burgeoning entrepreneurs?

Choose your partners and employees wisely, always maintain the highest ethical standards by treating people fairly and with respect, and know that you must work hard to be successful.

Southern Entrepreneurs

Susan Logan Huffman, founder of Reliant Investment Management, LLC

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