From Symphony to Speakeasy: Rachel Smalling's Entrepreneurial Journey

In a recent interview with Powered by Her host Tiffany Anton, our own Rachel Smalling shared insights into her entrepreneurial journey from nonprofit work to owning multiple businesses in Cookeville, Tennessee - including Lakeside Inn at Dale Hollow.

The Entrepreneurial Leap

Rachel Smalling's path to entrepreneurship wasn't exactly traditional. After years in the nonprofit sector working with the symphony, COVID boredom and a passion for revitalizing neglected spaces led her and partner Alex to purchase and renovate an old roadside motel on Dale Hollow Lake.

"In 2020 during COVID, my partner Alex and I basically decided to take on a huge renovation project," Rachel explained. "He has a contracting background. So took on a huge renovation project of renovating an old roadside motel. Think your classic old school, probably 40 bucks a night rundown [motel] and totally renovated that into a boutique motel, which is now on Airbnb and VRBO and it's right on Dale Hollow Lake."

This project, which would become Lakeside Inn at Dale Hollow, was just the beginning of Rachel's entrepreneurial journey.

Expanding the Hospitality Footprint

Success with the first property led to an opportunity that was too good to pass up.

"We actually bought an existing operating motel up there," Rachel shared. "Basically, it came for sale. Alex's parents are our business partners in that. And we decided if we didn't buy it, somebody else would and they'd be our competition. So the symbiotic kind of relationship between the two of those are just three miles apart. And we're kind of the only two games in town up in Birdstown at this point."

The two properties - Lakeside Inn and Sportsman's Lodge - serve different clientele but complement each other perfectly. While Lakeside Inn offers a boutique experience with online booking through Airbnb and VRBO, the Sportsman's Lodge maintains an old-school approach.

"The Sportsman's Lodge is actually very old school. We are like call and paper book calendar only," Rachel laughed. "When I bought the place, I laughed and was like, there's no way we're going to be able to make a profit without being online. And it's been three years and I have not [needed to change] - it's been so insanely busy."

From Lake to Lounge: The Speakeasy

Not content with just accommodations, Rachel's third venture took her in a completely different direction - opening 1854, a speakeasy-style cocktail bar and lounge in downtown Cookeville.

"If I do this on a small enough scale to keep overhead low and to not have super high costs going into it, that I think it would be really great for the community to have something more upscale and something different," Rachel explained about her thinking behind the speakeasy. "Just a little bit of a different experience than we have [with] great local restaurants and great local bars."

The speakeasy, true to form, maintains an element of mystery with its hidden entrance - located through glass double doors on the left side of the building housing Poets Coffee Shop, up the stairs, through a door marked "Smalling Investments."

Entrepreneurial Philosophy

Throughout the interview, Rachel revealed key aspects of her approach to business:

"Hope for the best, but plan for the worst and have a plan A, C, and D. So that's kind of my approach to business... I don't spend when I don't have to, and that's kind of saved me in a lot of things."

On staff selection and management: "We've been very intentional on our staff to have staff that are very engaging and enjoy being there. And I like to think that I pay them well enough to enjoy being there."

On the challenges of business ownership: "I think any business owner would be lying if they didn't tell you that they thought about like selling the business at least once every six months... The hardest thing is the constant [work]. At a nine to five job, you get to kind of leave your work at work for the most part. [As an entrepreneur] you don't ever get to turn it off."

Notable Quotes

"I think we deserve it. I think the people of Cookeville were ready." - On bringing upscale experiences to smaller communities

"You've never had a cocktail before in your life, we would love to introduce you to that or walk you through that." - On creating a welcoming atmosphere at 1854

"I've also learned that you can never fire too early, but you can definitely fire too late." - On management lessons learned

"I mean, it's a business, but it's also, I kind of say, my businesses are, I don't have children of my own, but they are my children." - On the personal connection to her ventures

"I was fortunate enough to be in a salaried position where we weren't doing performances. I worked for the symphony. So I was working, but I had a lot of extra time." - On how COVID created the opportunity for entrepreneurship

The Conversation: Inside the Journey

Finding Opportunity in Crisis

Tiffany: What made you decide, hey, let's do this [buy a motel]? You were working for a nonprofit at the time.

Rachel: "Yeah, so really I think it was COVID boredom. We didn't have a lot going on. I was fortunate enough to be in a salaried position where we weren't doing performances. I worked for the symphony. So I was working, but I had a lot of extra time. And we just decided to, we weren't traveling, obviously, because it was COVID. So we just jumped in. And we also really have a passion kind of for taking something old or something that's been neglected and turning that into something that can be used by the community and for people to enjoy."

Elevating Rural Experiences

Tiffany: Both of your main business ventures, this motel, boutique motel and a speakeasy are for an elevated clientele with custom signs and decor, which when you think of rural America, you don't think of higher end for rural America. What was the driving factor to go out on that limb?

Rachel: "Yeah, I think my number one driving factor was I think we deserve it. I think the people of Cookeville were ready. Not everybody might understand that concept of just, you know, handcrafted cocktails walking in, but my staff and I in the very beginning wanted to be a place that was different and upscale, but was also very welcoming."

Creating Unique Spaces

Tiffany: What was that journey like for you of creating this space that was going to be something that people haven't seen or haven't experienced before?

Rachel: "I think it's inspiration from other places. One of my love is, or one of my greatest loves is travel and food and cocktails from other places has been for a decade. That's one of my favorite things to do. So it's definitely pulled inspiration from a lot of other bars and cocktail bars... People really enjoy pieces with a story and things that aren't just super cookie cutter and mainstream."

Business Challenges & Growth

Tiffany: What often it's like, well, what's the best thing about owning a business? What's the worst thing? What's the hardest thing that you've gone through in the past year with the speakeasy specifically?

Rachel: "I think any business owner would be lying if they didn't tell you that they thought about like selling the business at least once every six months. As I say, it's always for sale, not on sale... I think the hardest thing is the constant [work].

At a nine to five job, you get to kind of leave your work at work for the most part. And you're kind of an entrepreneur and you understand this as well, that you don't ever get to turn it off. There's always something on the checklist to be done. When you travel, the buck stops with you." Our work always shapes us in some way, if someone work at a car dealership, then you can be sure that they’re far more aware of cars than the average person. When you’re an entrepreneur, then you’re far more aware of how businesses work than the average person too.

Finding the Right Team

Tiffany: How do you create that culture though of, you know, I find the hiring process to be one of the hardest things.

Rachel: "This is going to sound really maybe cliche, but in my experience of now a decade of hiring staff and unfortunately every now and then having to fire, which you're right is like the worst part about being in management or ownership. And I've also learned that you can never fire too early, but you can definitely fire too late... As far as hiring, I've found that any time that I have put out there or intentionally run interview processes, I've maybe been successful 30 to 40% of the time. But when I have people that just kind of naturally gravitate towards my business in whatever way or are friends of friends or I've worked with in other businesses [it works better]."

Plan Your Visit

Experience the boutique hospitality of Lakeside Inn at Dale Hollow yourself. With beautifully renovated rooms right on Dale Hollow Lake, it's the perfect getaway for those seeking comfort and relaxation.

For more information about reservations, amenities, and policies, visit our FAQs page or book directly through our listings on Airbnb and VRBO by searching for "Lakeside Inn at Dale Hollow."

And if you find yourself in downtown Cookeville, don't miss 1854 Cocktail Bar and Lounge, where the same attention to detail and quality that defines Lakeside Inn is applied to craft cocktails and an unforgettable atmosphere. Open Wednesday through Saturday evenings.

This interview was originally conducted for Powered by Her with host Tiffany Anton. Rachel Smalling is the owner of Lakeside Inn at Dale Hollow, Sportsman's Lodge, and 1854 Cocktail Bar and Lounge in Cookeville, Tennessee.