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The Sidewalk CEO

The Sidewalk CEO

By: The Sidewalk CEO
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 The Sidewalk CEO is an opportunity for local entrepreneurs to share their stories. Sheri and Leo have over 60 years of experience in business and industry, large and small.2025 Economics Leadership Management Management & Leadership
Episodes
  • Erika Hancock from State Farm

    Erika Hancock from State Farm
    Sep 8 2025

    In this episode of Sidewalk CEO, we sit down with Erika Hancock, owner/operator of Erika Hancock State Farm Insurance, an entrepreneur, Airbnb host, and Kentucky State Representative for District 57. Erika shares her journey from college graduate to one of the youngest State Farm agents in the country, as well as the lessons she has learned along the way.

    What We Talked About

    • Starting young in business: Erika launched her State Farm agency at just 23 years old, balancing training, a wedding, and building a book of business within 18 months of graduation.
    • The value of service in insurance: Why building relationships and prioritizing quality over quantity has fueled her agency’s long-term success.
    • Insurance insights: The difference between captive and independent agents, the importance of renewals, and how she helps clients manage rising premiums.
    • Life as a small-business owner: From early financial struggles to the “5-to-7 year grind” before profitability, Erika explains what it really takes to sustain a business.
    • Workplace culture: Her philosophy of treating staff as equals and creating a family-style environment that keeps employees for over a decade.
    • Airbnb Adventures: How Her Family Turned a Rental Property into a Memorable Guest Experience—Complete with Thanksgiving Dinners Shared with Strangers.
    • Community resilience: Lessons learned from floods, storm recovery, and the importance of green space in mitigating disasters.
    • Balancing roles: Juggling responsibilities as both an insurance agent and state legislator, and why teamwork at home and in the office makes it possible.

    Key Takeaways

    • Business success is about service and trust, not just sales numbers.
    • Small business ownership requires patience; expect a 5– to 7–year period before things truly stabilize.
    • Treating employees as equals and family fosters loyalty and longevity.
    • Community connection, whether through business, politics, or even an Airbnb, creates resilience and joy.

    Links & Resources

    • Erika Hancock State Farm Insurance Agency
    • Kentucky State Representative – District 57
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    41 mins
  • Episode 110 - The 525 Kitchen & The Flying Waffle

    Episode 110 - The 525 Kitchen & The Flying Waffle
    Aug 25 2025
    525 Kitchen in Frankfort is a business incubator offering shared equipment, co-working space, and event space. They are a 501(c)3 project started by Julie Derringer and Cynthia Smith, focusing on fresh food, agribusiness, and education to help local food entrepreneurs succeed. Their own business is the Flying Waffle and Southern Eats food truck. Cindy Smith of 525 Kitchen is managing multiple related businesses.525 is a business AND non-profit.She and her partner began with the Flying Waffle food truck.They needed more kitchen space and a place to park the truck, so they bought their building.Her partner Julie had the idea to set up as a nonprofit to be able to partner with community projects and help others as an incubator space.Flying Waffle began in September 2021, and their commissary kitchen opened in November 2022.Other food trucks do work out of their kitchen, as independent owners and operators.They have helped incubate Matt’s Hot Dog Stand, which operates in Frankfort and Lexington.They do not view the other food trucks as competition, because they are all so different.Some of their tenants are doing their food business full time, while others are part time.Food trucks either must prepare the food on the truck or in a commercial kitchen, so lots of the prep work gets done in the 525 space, and they don’t restrict hours tenants can use the kitchen.They call their truck the Flying Waffle and Southern Eats, because they’ve expanded beyond just waffles. Look for the distinctive pink and flowered wrap on their truck.Flying Waffle is an event only truck. They also use the truck for mobile catering, especially for business clients who are serving their employees.Cindy and Julie have been friends their whole lives.Cindy calls Julie a born entrepreneur. She owned a florist shop, then went back to school to become a nurse, and eventually opened Mulligan’s, an indoor golf facility with simulators.They put a kitchen in Mulligan’s and that is how they met the very helpful Wes Clark with the Franklin County Health Department, who Cindy says anyone wanting to start a food business should call first.Julie closed Mulligan’s in 2013 and started travel nursing, while Cindy was finishing up her bachelor’s degree and changing career paths.The waffle business was inspired by Pinterest scrolling, and Julie taking the initiative to incorporate their LLC and order the food truck.Julie does all their graphic design for their truck, logos, menus, and more.Julie and Cindy’s first year in business, they began to offer a menu and pickups for Thanksgiving, which was popular through word of mouth and Facebook.They did the same for Christmas and Bluegrass Home Chef was born as a meal prep business with people preordering menus and picking up weekly through the winter.As the food truck business picked up, they now only offer Bluegrass Home Chef periodically, and always around the holiday season.525 accommodates some non-food truck businesses, like Tincan Coffee which does its coffee roasting onsite in their own roaster, and Apocalypse Freeze Dried Treats which keeps their freeze dryers there as well. Thyme Together Charcuterie prepares her charcuterie there for pickup and for catering.525 Kitchen has multiple sinks and ovens for tenants, as well as a floor mixer and lots of KitchenAid mixers.Everyone has their own refrigerator space and dedicated dry storage.Some tenants also maintain their own private and separate equipment there.525 has gotten a grant from Kentucky State University to help install a produce washing station, plus two extra stoves in the back for canning so they can work with local farmers.If you have a large garden and need a large space to can, you can use the 525 for $25 an hour, and they will provide all the equipment, except for the jars.For food trucks, it’s a monthly membership fee on a sliding scale, based on storage and kitchen needs.The kitchen is located at 525 Warsaw Street in Frankfort, which is how they got their name.The Flying Waffle name came from the fact that they are mobile.Julie and Cindy have used social media to spread the word about 525, as well as word of mouth.Julie found the once “rustic” building they are using on Warsaw Street, that they’ve put lots of work in.Both women have fulltime jobs in healthcare while running their food businesses.One of their tenants, Chloe Cooks, does some special dietary catering like gluten free.Cindy advises that those wanting to start a food business learn Kentucky food code and how to access it.She also advises contacting your local food inspector who will ultimately permit you to do business.Their newest venture is the addition of a mobile cart that can be rented out for weddings and events to do things like a cupcake or cookie stand, a charcuterie cart, and more.Customers can have the cart manned by the business for onsite service or just drop off and set up.They prefer to work in a radius of less than two hours from ...
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    42 mins
  • 109 - Natalie Wilkerson of River City Provisions

    109 - Natalie Wilkerson of River City Provisions
    Aug 11 2025
    This week, Sheri and Leo talk with Natalie Wilkerson of River City Provisions in Downtown Frankfort. Natalie Wilkerson grew up in Frankfort and moved back in 2003 after getting her master's in historic preservation and civil engineering from the University of Kentucky.She moved back because she had a strong interest in downtown revitalization and historic preservation. In 2003, there wasn't much happening in downtown Frankfort.She and her husband started their first project almost 20 years ago along with a little neighborhood consortium to save the old Noonan's building from demolition. You might know it better now as Jesse's frame shop, which has been there for a long time.She and Layne, along with Ellen and Jim Glasgow, who are also passionate about downtown and revitalizing the neighborhood, bought that project and fully rehabilitated the building. And it's been a good corner building ever since.Her current business partner is Jen Williamson, a registered architect in town who has worked on numerous preservation projects in Frankfort and around central Kentucky.Eight years ago, she and Jen Williamson started a consulting business called Cumberland Ventures. With that, they have been doing historic preservation consulting, doing tax credit applications, and National Register nominations.About three years ago. Jen was the project architect on 311 Saint Clair, which was the first downtown boutique hotel to open, and also owned the rear adjacent building on Main Street. People probably know that as Marshall Steiner. Younger people may know it as Back Street Diner. That building on Main Street had been a diner for several decades. Jen and her husband had bought and rehabilitated the building, and saw the opportunity to develop a little courtyard since the buildings back up to each other at the rear.With more visitors coming into Frankfort post-COVID and with the Bourbon tourist industry taking off, they saw a need for more retail on the first floor. So they relocated some of the office spaces from our prime commercial real estate. River City Provisions just came naturally.Then there were people in town who were going to need places to stay and things to do. They wanted to provide a storefront that would give them a little slice of Frankfort and let them take a little bit of Frankfort home with them on their journey.When they started River City Provisions, they “shop-shared” the space with another business, The Linen Closet, for the first year.Then, a space two doors down became available for rent, so The Linen Closet moved its business two doors down.We had this little incubator space so we could both get up on our feet.They also have a water refilling station in their store for Living Waters Kentucky members.The downtown business community is powerful in partnerships and collaborations.They pride themselves on being open seven days a week because it's not only weekends that people come downtown to shop and have fun.She thinks of them as a kind of modern-day general store. They have provisions, hence the name, for people who are traveling who forgot their toothpaste or need a charger or need a snack on the go.They've got a water refill station in case someone has a water bottle they need to fill up while they're walking. They also have local artists. They have a ceramic artist, a painter, and a leatherworker. They offer handmade leather products and jewelry, all locally made.They try to have small, little things that somebody can pick up and will remind them of their time in Frankfort.They try to meet the needs of a wide range of different types of customers. They're particularly fond of their hometown's proud t-shirts and apparel items.They have hats, shirts, and sweatshirts with the new Frankfort flag logo.They've got some neighborhood t-shirts.They are seeing more visitors because of having places for people to stay overnight, like the 311 Saint Clair, the Ashbrook, and the Delegate.They've noticed a significant increase in traffic during the week due to the foot traffic.They do all the designs themselves, print them locally at CLS, and try to mix it up. They push a design out, and when it sells, they move on to the next thing.They've got another little project in the works for a shirt and a sweatshirt that they're excited about with an image of “a local friend of ours”.The opening of new hotels makes them a considerable part of the Bourbon Trail. The Bourbon Trail attracts many visitors who come in with their Buffalo Trace wristbands.Also, plenty of locals come through because they haven't been downtown in a while.She thinks Frankfort has enough now with the retail, restaurants, and events that lots of people with lots of different interests can come down and have a good time.Natalie also buys and rehabilitates properties, which aligns with her interest in preserving and revitalizing Frankfort to make it a great place to be.Her particular interest is in downtown, where she lives, and that's ...
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    32 mins
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