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In this episode, host Matt Wagner sits down with Dale Sexton, owner of the legendary Dan Bailey's Outdoor Co. in Livingston, Montana. Dale shares his journey of taking over the iconic outdoor retail business and navigating the evolving outdoor industry and customer landscape.
Key Takeaways:
Journey to Business Ownership: Dale discusses his process of transitioning ownership of Dan Bailey's Outdoor Co. from his father, integrating new ideas while preserving the business's long-standing reputation and traditions. Adapting to Industry Change: He explores how the outdoor retail sector has transformed, from the rise of e-commerce to shifting consumer preferences, and how Dan Bailey's has adapted its in-store experience and product mix in response. Cultivating Community: As a Main Street business, Dale emphasizes Dan Bailey's critical role in the Livingston community. He shares strategies for engaging locals and tourists through events, partnerships, and more. Weathering Challenges: Dale reflects on navigating challenges like supply chain disruptions and the pandemic, offering advice on maintaining resilience as a small business owner. Vision for the Future: Dale outlines his plans to further strengthen Dan Bailey's position as a premier outdoor outfitter while preserving the business's authentic character and local roots.Connect:
Visit Dan Bailey's Outdoor Co. website Follow Dan Bailey's on Facebook Follow Dan Bailey's on InstagramEpisode Links:
- Watch video interview
- Listen on Apple Podcasts
- Listen on Spotify
- Subscribe for updates
Join us next week for more insights into the evolving landscape of Main Street business.
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Join host Matt Wagner for his conversation with Mallory Dabney, owner of Heyday, a home goods store in Bozeman, Montana. In this episode, Mallory shares her journey from moving to Bozeman from California, learning how to work in retail, and eventually becoming the owner of one of her favorite downtown shops.
In this episode, we dive deep into:
- Journey to Ownership: Mallory describes the process of acquiring the business through an SBA loan, working closely with the previous owner, and navigating the financial and work-life balance considerations as a new business owner and young mother.
- Brand Identity & Marketing: Mallory discusses the importance of brand identity and how she thinks of Heyday as a person with a specific personality and voice. This guides their product curation, marketing, and overall customer experience.
- Balancing In-Store & E-Commerce: They discuss Heyday's successful e-commerce channel, which has seen significant growth, and how Mallory's team manages the inventory, marketing, and sales between the online and in-store channels.
- Focus on Community: Mallory emphasizes the critical role community plays for Heyday, from hosting local events to partnering with the downtown business association. She sees Heyday as an anchor for the community.
- Advice for Other Small Business Owners: Mallory provides advice for other small business owners, focusing on cultivating a strong, empowered team, maintaining a positive mindset through challenges, and extending grace to themselves as entrepreneurs.
Connect:
Check out Heyday’s website Follow Heyday on Facebook Follow Heyday on Instagram Follow Heyday on PinterestEpisode Links:
- Watch video interview
- Listen on Apple Podcasts
- Listen on Spotify
- Subscribe for updates
Join us next week for more insights into the evolving landscape of Main Street business.
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Join host Matt Wagner for his conversation with Patrick Jackowski and Matt Horne, the duo behind Firehouse Coffee 1881, a thriving coffee shop housed in a firehouse in historic Fort Monroe, a decommissioned military compound located in Hampton, Virginia. Fresh from their appearance as featured panelists at the Virginia Retail Alliance's Retail Matters Summit, these young entrepreneurs are redefining what it means to be business owners in today's rapidly evolving retail landscape.
In this episode, we dive deep into:
- Introduction to Patrick and Matt: Discover how two lifelong best friends transformed their childhood bond into a powerful business partnership. Patrick and Matt share candid insights about how their complementary strengths and lifelong friendship created the perfect foundation for their entrepreneurial venture.
- Gen Z Entrepreneurs: Step into the world of Gen Z entrepreneurship, making up only 8 percent of all business owners – but not for long. Learn why this generation is uniquely positioned to disrupt traditional business models and how their digital-native perspective is reshaping customer experiences. Patrick and Matt offer a fascinating glimpse into how their generation's values and vision are influencing their business decisions.
- Journey to Ownership: Follow the remarkable story of how these young entrepreneurs' longtime dream of business ownership collided with an unexpected opportunity. Hear about how a historic firehouse-turned-coffee shop caught their attention and how they knew instantly it was their chance to create something special. They share the serendipitous way they decided take the leap and the gut instincts that told them this was their path.
- Success Stories and Challenges: From forming their business plan to overcoming funding challenges, Patrick and Matt share their innovative solutions to funding obstacles, their strategies for winning over their community, and the valuable lessons they learned about perseverance in the face of doubt.
Connect:
Check out Firehouse Coffee 1881’s website Follow Firehouse Coffee on Facebook Follow Firehouse Coffee on Instagram Subscribe to Firehouse Coffee’s YouTube channel Follow Firehouse Coffee on LinkedInEpisode Links:
- Watch video interview
- Listen on Apple Podcasts
- Listen on Spotify
- Subscribe for updates
Join us next week for more insights into the evolving landscape of Main Street business.
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In this episode, Matt reveals the data-driven trends that will define the 2024 holiday shopping season—and shows you exactly how to leverage them for your small business.
You'll discover:
Fresh Retail Data: Current consumer insights and market analysis to inform your holiday strategy
5 Game-Changing Shifts: Evidence-based predictions for holiday shopping behavior—and how to adapt your business
Marketing Playbook: Proven tactics to capture customer attention when it matters most
Whether you're a seasoned retailer or preparing for your first holiday season, this episode delivers actionable strategies to help your business thrive during retail's most critical period.
Episode Links:
- Watch episode video
- Listen on Apple Podcasts
- Listen on Spotify
- Subscribe for updates
Join us next week for more insights into the evolving landscape of Main Street business.
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Join host Matt Wagner as he welcomes Kaycee McCoy, co-owner and creative lead at Pawsnickety Pets in Norfolk, Virginia. Kaycee and her best friend, Shizuka Benton, launched the all-natural and organic pet supply business in Norfolk at the start of the pandemic, but have used their combined talents – Kaycee's passion for all-things marketing and Shizuka’s penchant for operations and management – to keep the business growing and thriving over the last four years.
Here’s what we'll cover:
- Introduction to Kaycee McCoy: Learn about Kaycee’s journey to entrepreneurship and what brought her to owning her own pet supply business – without any experience in the pet industry or retail!
- Success Stories and Challenges: Hear about obstacles Kaycee and her team have overcome over the years, as well as the wins they’ve had along the way.
- Marketing & Using New Tools: Kaycee is a whiz at all-things marketing – and a self-proclaimed “marketing alchemist”! Learn about the tools, resources, and strategies she implements with her team to keep their business growing year over year.
- Owning a Business with a Friend: Kaycee and Shuzuka have been friends over 12 years – and they’re often asked how they can stay friends while also managing a business together. Learn about the ways the friends cultivate a thriving business while keeping their BFF-hood strong.
- Advice for Other Entrepreneurs: Kaycee shares her advice and insights for other entrepreneurs that own Main Street businesses. Tune in to hear her wisdom!
Further Reading:
Take a look at the Pawsnickety Pets website (designed by Kaycee!) Explore the Downtown Norfolk site Learn about the Virginia Main Street programConnect:
Follow Pawsnickety Pets on Facebook Tune into Pawsnickety’s YouTube channel Follow Pawsnickety Pets on TikTokEpisode Links:
- Watch video interview
- Listen on Apple Podcasts
- Listen on Spotify
- Subscribe for updates
Join us next week for more insights into the evolving landscape of Main Street business.
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Join host Matt Wagner as he welcomes David West, director of Premier Retail Marketing and based in Adelaide, South Australia. David is a leading expert in commercial district management and a key figure behind Australia’s Main Street movement, as chair of Main Street South Australia. In this inaugural international episode, Matt and David explore the nuances of Main Street revitalization, comparing approaches and challenges faced by small businesses in the U.S. and Australia.
Here’s what we'll cover:
- Introduction to David West: Discover David's journey from managing shopping centers to becoming a pivotal player in the Main Street movement in Australia.
- Main Street Movement in Australia: Learn about the evolution of the Main Street movement, including the pivotal role of Victoria and the establishment of Main Street Australia.
- Success Stories and Challenges: Hear about the various models of Main Street organizations in South Australia, including their partnerships with local councils and business associations.
- Marketing and Economic Development: Understand how Main Streets in Australia compete with shopping centers and the importance of effective marketing strategies.
Further Reading:
- David West’s Book: Main Street Management: Successful Retail Strategies
- Main Street South Australia: Learn more about the initiatives and programs being developed to support Main Streets across Australia.
Connect:
- Follow David West on LinkedIn for insights and updates on the Main Street movement in Australia.
- Stay tuned for more episodes exploring innovative strategies for small business success on Main Street.
Episode Links:
- Watch video interview
- Listen on Apple Podcasts
- Listen on Spotify
- Subscribe for updates
Conclusion:
This episode is a rich conversation about the interconnectedness of communities, businesses, and local initiatives. Tune in to explore how lessons from South Australia can inform the future of Main Streets everywhere.
Join us next week for more insights into the evolving landscape of Main Street business.
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In this episode, Matt chats with Tee Rowe, the President and CEO of America’s Small Business Development Centers (ASBDC). The centers offer training, advice, and resources to help small business owners thrive in their communities.
Tee has dedicated over 30 years to supporting small businesses. He started his journey working with the Committee on Small Business in the House of Representatives and later joined the Small Business Administration (SBA) during the Bush Administration. Now at ASBDC, Tee continues to advocate for small business owners across the country.
During their conversation, Matt and Tee explore how the changing economy affects small businesses, the importance of understanding new technologies like AI, how national laws impact business owners, and best ways to connect with local SBDCs.
Further Reading: America’s SBDC | Find Your SBDC | U.S. Small Business Administration | Red Helicopter by James Rhee
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"In this episode of Main Street Business Insights, Matt interviews Patrice Hull, the owner of Stuff We Wanna Say Custom T-Shirts and Apparel and c2bn / Created to be Noticed, based in Atlanta, Georgia.
Patrice began her career in corporate health insurance, but after being laid off just before Christmas, she decided to pursue her passion. She bought a heat press and printer, started designing and printing her own t-shirts, and launched her brand, Stuff We Wanna Say. She started small, producing t-shirts at a local co-op, and gradually expanded her offerings to include sunglasses, pants, and more.
Later, Patrice introduced her second brand, c2bn (Created to be Noticed), focusing on high-quality, multi-functional canvas bags. Her first major client was a shoe store in the Little Five Points neighborhood, and soon she was filling wholesale orders for other local retailers. Her work eventually caught the eye of celebrities like Catherine Zeta-Jones.
Tune in to hear Patrice share how she built her brands, adapted to grow her business, and the importance of pursuing what you love.
Further Reading: Stuff We Wanna Say | Created To Be Noticed | Little Five Points | Georgia Main Street "
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In this episode of Main Street Business Insights, Matt sat down with Mindy Bergstrom, owner of Cooks Emporium, Nook & Nest, Z.W. Mercantile, and The Recipe, all located in downtown Ames, Iowa.
Mindy’s passion for entrepreneurship at an early age watching her parents run their own business. She started her first business while in college, designing websites for other small business owners. After graduating from college, she landed a project management job at a marketing firm. During this time, she continued to dream and plan to open her own business one day.
Her opportunity came when she visited her husband Patrick’s hometown and fell in love with The Cooks Emporium, a local kitchen and home goods store. What started as a dream turned into reality in 2018 when Mindy and Patrick took over the store. Since then, they've expanded with three more ventures: Nook & Nest (a home decor shop), Z.W. Mercantile (a zero-waste store), and The Recipe (an event space with cooking classes).
Tune in to hear Mindy’s insights on entrepreneurship, community engagement, the art of pivoting, and her unique approach to redefining failure.
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In this Main Street Business Insights episode, Matt sat down with Kristin Smith, chef and proprietor of The Wrigley Appalachian Eatery in Corbin, Kentucky.
As a fourth-generation Appalachian Main Street merchant partnered with a strong passion for the local food movement, Kristin began her path to entrepreneurship by working at her family farm selling heritage pork and dry-aged beef at the local farmer's market (which she also helped found along with a group of local women). The products were slow to sell, so Kristin began cooking the meat at the market to offer patrons a taste. Before long, the prepared food was far outselling the packaged products. When a historic property in downtown Corbin became available, Kristin knew it was time to move into a brick-and-mortar space.
Since launching The Wrigley, the business has been featured in Time Magazine and The Food Network, and Kristin landed a spot on James Beard Foundation’s Women Entrepreneurial Leadership group in 2023. But outside of the national acclaim they’ve received, Kristin and her team’s primary objective is to stay rooted in their local community.
In their conversation, Kristin talks about her deep roots in Appalachia and small-town business ownership, her strong belief in authentic community building, and why she’s saying “no” more often.
Further Reading: The Wrigley Taproom & Eatery | James Beard Foundation Women's Entrepreneurial Leadership | Downtown Corbin | Kentucky Main Street
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In this episode of Main Street Business Insights, Matt talks with Joshua and Jared Ravenscraft, co-founders of New Frontier, a sustainable apparel brand in Morehead, Kentucky.
Today's episode celebrates sustainable, artisan fashion with Joshua and Jared Ravenscraft, brothers and co-founders of New Frontier. Despite the fashion industry's global impact on carbon emissions, New Frontier stands out with their environmentally friendly approach, using recycled materials and rainwater in their production processes.
In their conversation, they discuss the wastefulness of the fashion industry and New Frontier's commitment to sustainability, reflect on their role in Eastern Kentucky's economy and culture, highlighting the intersection of local identity and global markets, and share their insights into the journey of scaling a sustainable fashion business from a small town.
Join us as Matt Wagner explores how New Frontier embodies the spirit of Main Street entrepreneurship, blending innovation with community stewardship. Their story inspires us to rethink where and how sustainable businesses can thrive, proving that impactful entrepreneurship knows no geographic bounds.
Further Reading: New Frontier Brand | Downtown Morehead, Inc. | Kentucky Main Street Program | Fuzzy Duck Coffee Shop
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In this episode of Main Street Business Insights, Matt talks with Mileyka Burgos-Flores, CEO of the Allapattah Collaborative CDC in Miami, Florida, the only designated Main Street community in Miami. Mileyka is also this year’s recipient of the Mary Means Leadership Award.
Allapattah, one of Miami’s oldest and most diverse neighborhoods, is home to Little Santo Domingo, revitalized by Dominican immigrants along the 17th Avenue corridor. Mileyka, originally from the Dominican Republic, found her calling in Allapattah during college at the University of Miami. She quickly became involved in community events and eventually led efforts to create a strategic plan for the area, forming the Allapattah Collaborative CDC in 2019.
When the pandemic hit in 2020, Mileyka and her team shifted focus to support local small businesses, aiming to preserve the cultural identity of Allapattah and Little Santo Domingo. Their initiatives include providing resources, education, and opportunities tailored to entrepreneurs in the district.
In their conversation, Mileyka and Matt discuss the importance of Main Street leaders supporting small businesses, the importance of "owning the dirt," and Mileyka’s advice for fellow community leaders.
Further Reading: The Allapattah Collaborative CDC | Florida Main Street | 17th Ave – Allapattah Action Plan | Small Business Anti-Displacement Network | Mary Means Leadership Award | “Own the Dirt” Swag
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In this episode of Main Street Business Insights, Matt chats with Ross Chanowski, owner and founder of NuMarket. NuMarket is a leader in crowdfunding solutions for small businesses with a focus on food services.
Ross's journey from studying marketing and behavioral psychology to graduating from the London School of Economics sparked his passion for "social entrepreneurship." He founded NuMarket on the idea of ""crowdfunding for credits."" Unlike other types where you might donate or receive rewards, this model lets anyone invest in a small business and earn credits to use at that business over time, gaining more value than they put in.
During their discussion, Ross shares how his background shaped NuMarket, explains the various crowdfunding methods, and highlights why NuMarket's approach is ideal for small businesses. They also cover how Ross stays resilient during industry changes, the importance of listening closely to customers to stay innovative, and practical ways small businesses can leverage crowdfunding to grow.
Tune in to learn how NuMarket is transforming crowdfunding into a tool for positive change and how small business owners can benefit from these innovative solutions.
Further Reading: NuMarket
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In this episode of Main Street Business Insights, Matt talks with Ebenezer Akakpo, a designer and jeweler who owns Akakpo Design Group and Maine Culture in Westbrook, Maine. Ebenezer recently won an award from Discover Downtown Westbrook's Paper City Pitch Contest in May 2024.
Ebenezer's businesses blend artistic design with cultural heritage. His jewelry company, Akakpo Design Group, honors his Ghanaian roots through symbolic designs that reflect his heritage's history and culture. His other venture, Maine Culture, creates beautifully designed products celebrating Maine's natural beauty, allowing customers to carry a piece of Maine wherever they go.
Join us as we explore Ebenezer's journey into entrepreneurship, the inspiration behind his designs, and how cultural significance influences his work in both business and art.
Further Reading: Akakpo Design Group | Maine Culture | Paper City Pitch Contest | Discover Downtown Westbrook | Main Street Maine
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Welcome to another episode of Main Street Business Insights! In this conversation, Matt explores the story of Elements: Books Coffee Beer, nestled in the heart of Biddeford, Maine, with co-owners Katie Pinard and Michael Macomber.
Rewind to 2010, when Michael returned to his hometown, juggling a master’s degree and the elusive quest for the perfect destination workspace to work on his dissertation. He quickly noticed the void in communal hubs, and envisioned a haven that merged a bookstore, coffee shop, and taproom. Thanks to a pivotal small business grant from the local Main Street program, Heart of Biddeford, Michael's dream took flight. Enter Katie, joining the fray in 2013 as both manager and business partner, catalyzing Elements' evolution into the thriving hotspot it is today.
In their candid conversation, the trio explores the profound impact a business wields in fostering belonging and community spirit. They delve into the art of attentive staff management, emphasizing the significance of listening and respecting their voices. Plus, they unravel the criticality of consistent operating hours in nurturing customer loyalty and engagement.
Tune in to gain fresh perspectives on entrepreneurship, community building, and the art of cultivating a cherished local gem.
Further Reading: Can Strong Social Infrastructure Cure the Loneliness Epidemic?, Planning Magazine | Elements Books Coffee Beer | Heart of Biddeford | Maine Downtown Center
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In this special episode of Main Street Business Insights, recorded in front of a live audience during the Main Street Now Conference, Matt sat down with Alycia Levels-Moore, owner and founder of ASL Creative Firm and POLARIS, an event and co-working hub, based in Birmingham, Alabama.
Alycia moved to Birmingham’s Woodlawn neighborhood roughly a decade ago, and shortly after started volunteering in various community and civic engagement initiatives. “At the time, ten or eleven years ago, it was very much in transition, it was not the Woodlawn we know now,” Alycia said. “My thought process when I do anything is how can i make sure that whatever I’m apart of is better once I’m finished with it.” She began supporting neighborhood small business owners, organizing community events, and eventually, founding the community-based co-working and event space and educational hub, POLARIS, with the mission of creating a safe space to nurture community and build local entrepreneurship.
In addition to her work at POLARIS, Alycia also founded ASL Creative Firm, a consulting agency specializing in community development, program management, and strategic planning. Through her consulting work, Alycia was brought on board as the lead project manager for the Where It Starts: Breaking Barriers to Business initiative, supported by the Truist Foundation and alongside Living Cities, to accelerate wealth-building pathways for business owners of color in five cities in the southeast.
In their conversation, Matt and Alycia discuss her journey to business ownership, her community development work in Birmingham and through the Breaking Barriers to Business initiative, and the importance of resilience and self-belief for entrepreneurs.
Further Reading: ASL Creative Firm | POLARIS | Where It Starts: Breaking Barriers to Business | Main Street Now Conference | About the Woodlawn District | Main Street Alabama |
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In the last episode of season two of Main Street Business Insights, tune in as host Matt Wagner breaks down how to understand and synthesize local market data.
While market understanding can feel daunting, it’s not only a purely data-driven exercise. While data plays a crucial role, effective market analysis goes beyond just crunching numbers. It's a blend of science and art, requiring a deep understanding of your community, its needs, key drivers, and the broader context of how it functions as a place where consumers, visitors, locals and small businesses and organizations converge.
In the episode, Matt explains his philosophy for market analysis, how to transform data interpretation into effective strategy, and the importance of local contexts.
Further Reading: IRS Migration Data | Esri Data Mapping | Placer.ai
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"In this episode of Main Street Business Insights, Matt sits down with Glen Ellis, owner of Sycamore Education, Dominion Catalyst Services, and Milady Coffeehouse in Fremont, Nebraska.
Glen started his career working in programming and software development for international corporations, but after around 20 years, was feeling unfulfilled with the work. From there, he started volunteering at his children's school, and learned the school system’s management software had problems to be addressed. He rewrote the program, named it Sycamore Education, and began implementing it in other schools. After two years, Glen and his wife decided to take a leap of faith and take on Sycamore Education full-time.
The first few years of business ownership were challenging for Glen and his family – but through hard work and trial and error, they began hiring employees and gaining new clients. After getting through the initial start-up phase, Glen gained a newfound passion for supporting other entrepreneurs.
“My desire was not only keeping my company going, but also giving back to what we went through and doing it better than we did,” said Glen. Out of this desire, Glen purchased a historic building in downtown Fremont with the goal of converting it into a business incubator space. On the first floor, they started Milady Coffeehouse to attract community and provide a space for discussion and creativity. The second floor houses a suite of affordable office spaces available for entrepreneurs to launch their ideas.
In their conversation, Matt and Glen discuss the importance of creating community, ways to support other entrepreneurs, why he chose to launch his businesses in a small community, and more.
Further Reading: Sycamore Education | Milady Coffeehouse | Fremont Main Street | Nebraska Main Street Network "
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In this episode of Main Street Business Insights, Matt sits down with Derek King and Jaime Courtney of Shoalwater Seafood, and Shane Thomas, Tribal Council Vice Chair of the Shoalwater Bay Indian Tribe. Located in Tokeland, Washington, Shoalwater Seafood grows oysters using a system that can stand up to the strong winds, rising sea levels, and difficult weather of the Hood Canal. In 2018, Shoalwater Seafood and the Shoalwater Bay Indian Tribe formed a working relationship that has led to the creation of an independent oyster nursery, beginning the development and certification of several hundred acres of Tidelands owned by the Shoalwater Bay Indian Tribe.
The Shoalwater Bay Indian Reservation is a participating organization in Main Street America’s USDOT Thriving Communities program. Through the program, we are working with local community leaders to develop an increased awareness of Federal opportunities, prepare community leaders to implement infrastructure and community development projects, and build lasting local capacity for carrying out projects. Given the partnership, the group discusses how transportation and logistics impact Shoalwater Seafood’s business given the remoteness of their location to tourists and markets.
In the episode, the group discusses the partnership between Shoalwater Seafood and Shoalwater Bay Indian tribe, their journey to oyster farming, insights on being a tribal enterprise, how tribal culture and values are reflected in the business, ways climate change has impacted the business, and more.
Further Reading: Shoalwater Seafood | Washington State Main Street Program | Shoalwater Bay Indian Tribe | USDOT Thriving Communities Program
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In this episode of Main Street Business Insights, Matt sits down with Casey Woods, Executive Director of Emporia Main Street in Emporia, Kansas.
In their conversation, they discuss how Casey’s journey to becoming a Main Street director, his focus on entrepreneurship, how he creates new opportunities for local business owners, and how other Main Street leaders can drive economic development in their communities.
Further Reading: Emporia Main Street | Emporia Main Street Fab Lab | Kansas Main Street
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