Honoring Small Business Triumphs: Inspiring Stories of Retail Owners' Success

small business week 2024

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I have some amazing people I want you to meet and hear their advice for small business owners, but first, while researching this important celebration, I have to take a step back in time to where it all began.

When did Small Business Week Start?

President John F. Kennedy enacted the proclamation to celebrate small businesses every year on the first week of May. According to the SBA, small businesses generate over 60 percent of net new jobs, while their share of employment is less than 50%.

What is a small business? The SBA Office of Advocacy generally defines a small business as an independent business with fewer than 500 employees.

The Significance of Small Business Week: A Historical Perspective

Remember, every big business starts small; Small Business Week celebrates this spirit of growth and entrepreneurship. Ben Franklin was our best-known early entrepreneur because he knew how to commercialize his ingenuity first as a printer and then as a newspaperman. 

Many people don’t realize how much risk there is when you decide to strike out on your own: that day you walk away from a guaranteed paycheck, getting a loan from the bank, your first sale to a stranger, hiring your first employee, the sweat from trying to make payroll. And all while keeping a positive face for the business. 

Even after I had become the Retail Doctor, amassed a following, and had spoken at significant conferences, my mother would ask at Sunday dinner, “Are you still doing that speaking thing?” She worked as a school teacher for nearly 50 years. The freedom another path could afford someone did not compute.

Three Milestones: Reflecting on 50 Years of Small Business Week

Each milestone is a testament to the tenacity and ingenuity that drive our small business community.

  • In the 1800s, shopkeepers went from bartering for goods to systems of credit, which allowed upwardly mobile consumers to buy more.
  • In 1953, the US government created the Small Business Administration as an independent entity to fund and educate potential and current small business owners.
  • In 2020, The Paycheck Protection Program, established by the CARES Act, was implemented by the SBA. This program provided small businesses with funds for up to 8 weeks of payroll costs, including benefits, during the pandemic.

The Economic Impact of Small Businesses on the National Economy

Think big, yet act small; small businesses are the backbone of our economy.

According to the Small Business Administration, small companies generate 1.5 million jobs annually, accounting for 64% of new jobs in America. Small businesses also contribute 44% of the U.S. economic activity, so as the number of new businesses grows so does their economic contributions.

Inspiring Stories from Small Business Owners

With two podcasts, a popular blog, and my work as a business consultant, I’ve gathered these three stories to share of entrepreneurs who embody small businesses' strength, grit, and optimism. To improve your Retail Management, read their stories below. 

Deanna Wallin, Founder & CEO of Naples Soap Company

Deanna Wallin’s emotional journey through significant personal and professional challenges highlights her resilience, leadership, and deep commitment to her business and community. She shared several stories throughout this podcast

Starting Out: Deanna was a nurse and later worked in medical sales, which she found to be cutthroat. Post-divorce and approaching 40, she felt out of place as a female in her field.

Transition to Retail: A friend suggested she open a store next to hers in a tourist area. Another friend pointed out her large collection of soaps and lotions at home, which led to the idea of selling natural soaps due to her and her daughter's struggles with skin conditions like eczema and psoriasis.

Early Success: She began in a 300-square-foot space, quickly expanded due to demand, and established trust with customers by leveraging her nursing background to discuss skincare, which led to the business's rapid growth.

Hurricane Impact and Response: Deanna described her experience during a major hurricane that hit on her birthday. She watched as the storm caused extensive damage, describing it as “sitting down at her dinner table and refusing to leave.”

Immediate Aftermath: She found her warehouse roof in the parking lot, significantly impacting her operations. Deanna was deeply involved in the recovery, ensuring her team was safe and cared for, which included relocating operations, salvaging what they could, and managing customer service amidst chaos.

Recovery and Reopening: Despite the extensive damage, Deanna and her team managed to reopen three stores within 67 days post-hurricane, showing resilience and a strong commitment to her community and business. Just as they were recovering, a drunk driver crashed through one of their newly repaired buildings on Black Friday, 

Reflections on Retail and Community Support: Deanna emphasizes the importance of being there for her staff and community, comparing disaster support to putting on an oxygen mask before helping others.

Customer Support: She appreciated the community's response, as people supported her business by placing orders and sending notes of encouragement, which helped them to keep going.


Billy Eklund, Owner of Eklund’s Farm Machinery, Stamford, NY

Billy's story captures the emotional journey of revitalizing a family business, the challenges of change, and the gratification of seeing those efforts appreciated by customers, leading to immediate business success.

Billy Eklund's story revolves around the transformative journey of Eklund Farms, especially the changes made to their farm machinery store, with my guidance. 

Initial State: Billy's grandfather started the store in 1950. Initially, it was cluttered, resembling a warehouse with parts and shelves that made navigation difficult for customers.

Transformation Goal: The goal was to make the store more welcoming and organized so that customers would be impressed and find everything they needed easily.

Consultation and Implementation. We drew up plans for improvements. This collaboration led to significant changes in the layout and presentation of products.

Immediate Impact: After rearranging the store, particularly the front, where new tractors and UTVs were displayed differently, products began selling immediately. This change was so effective that customers thought the products were new additions.

Extended Efforts and Team Involvement: The transformation required long nights, with staff staying until 9 or 10 p.m. Billy highlights his team's dedication, which pushed hard to implement the new changes.

Customer Reaction: After the makeover, customers were surprised and thought they were in the wrong building due to the dramatic improvements. The new store layout led to a better shopping experience, and they doubled their sales within a year.


Heidi Owen West, Founder of Lifestyles of Saratoga, Saratoga, NY

Heidi West's story paints a picture of a dedicated, innovative, and resilient business owner who has navigated the ups and downs of the retail industry while maintaining a strong connection with her community and staying true to her ethical values.

Heidi shared several stories on my podcast, reflecting on her journey and insights into the retail industry. Here are the key stories and moments she shared:

Background and Early Influences: Heidi's first job was at the Saratoga Performing Arts Center, where she worked in retail tents at a young age, handling transactions without any aids like calculators or registers. This experience taught her fundamental retail skills and fostered her love for the industry.

Passion for Fashion: From a young age, Heidi was intrigued by how clothes could alter perceptions and identities, shaping how people are treated and react in social settings.

Career Progression and Business Growth: Heidi attended the Fashion Institute of Technology in New York City, further solidifying her desire to pursue a career in fashion and retail.

Expansion of Business: Over 30 years, Heidi successfully expanded her business, opening two additional brands near her original store, Lifestyles of Saratoga in Saratoga Springs.

Philosophy and Business Approach: Heidi emphasizes the importance of understanding and listening to customers, which guides her purchasing decisions and store offerings.

Sustainable Fashion: She is committed to sustainability in fashion, choosing to partner with brands like Eileen Fisher that align with her values regarding environmentally responsible practices.

Navigating Vendor Relationships: Heidi discussed the complexities of maintaining beneficial relationships with vendors, especially in the face of challenges like direct selling by vendors, which can undermine retail partnerships.

Resilience and Adaptation: Heidi illustrates her strategies for adapting to the changing retail landscape, focusing on community engagement and digital presence.

Advice from Successful Retail Entrepreneurs

As a business consultant and in my online training program, SalesRX, I work with many innovative people. I often feature them on my podcasts and videos. Here are three I think are super-smart.

They not only have great advice, but you can also follow their feeds on Instagram.

Tony Drockton, CEO of Hammit, Manhattan Beach, CA

Listen to his interview on my podcast:

Importance of Staff Training and Customer Experience: "I quickly learned that our first sales team for our retail store needed better selling skills for in-person interactions. The biggest feeling was walking into our retail store and not feeling the energy that I want for our customers.."

Simple and Effective Training Modules: " I fell in love with how basic and simple SalesRX was and easy to understand. Short time frames, five, fifteen minutes. Boom. Boom. Boom. Go. Go. Go.."

Leveraging Old School Skills: "We were almost all wholesale three years ago. When we shifted, I loved it because I was able to use the old-school skills that I learned in my dad's little grocery store in Ohio, which was to carry the people's groceries out. You say hello. You say goodbye. You say, hey. You have to connect to them and welcome them back in."


Tammi Ketterman CEO of Ketterman's Jewelers, Leesburg, VA

Listen to her interview on my podcast

Innovative Event Planning and Customer Engagement: "With our Brighton line, we developed an event based on the movie 'The Greatest Showman' coinciding with the release of a handbag featuring a zebra, similar to the movie’s theme. We re-wrote some of the movie's song lyrics and performed them during the event, offering different showtimes throughout the day. This created a memorable experience that tied our products to an enjoyable event, leading to significant sales and lasting customer associations with our store whenever they hear those songs or see the movie." Check out their ABBA promotion in their feed above.;)

Significance of Triggers in Retail Experience: "Triggers are things that cause you to think of something else, like scents. Our store has an Asian mint scent that reminds people of Ketterman’s when encountering similar smells elsewhere. This sensory branding helps reinforce customer recall and loyalty. Additionally, using rum cakes as a special holiday treat has become a signature of our customer experience, making our brand memorable beyond just the products we sell."

Community and Relationship Building: "We’ve been cultivating deep relationships with our customers by not just treating them as transactions but as part of our community. For instance, we send cards and gifts to our 'friends and family' customers each holiday season, inviting them to visit and receive a special gift, such as a rum cake or a decorative item that represents our brand. This approach has turned our customer interactions into ongoing relationships, increasing loyalty and repeat business."


Brian Travilla, Author of Leading in Retail: The Humor and Art of Retail Leadership, Chicago, IL


Listen to his interview on my podcast 

The Value of Mentorship in Retail: "I would say training and even more mentoring were phenomenal at Montgomery Ward. They had long-term leaders who were vulnerable and took you under their wing. I had the honor to learn from some just unbelievable retail leaders. This has played out as I've taken other positions through other bigger-box retailers, where I've committed to mentor others as I was mentored."

Performance Management and Empathy: "I had a store leader who was really disconnected as we entered the holiday season. After persistent issues, I had to go to performance management, but I also showed a lot of empathy. When the store leader finally admitted to having major problems with the holidays due to family issues, I could relate and show empathy. Combining structured management with genuine personal concern, this approach eventually turned the situation around."

The Importance of Role Playing in Training: "I love role play, and I think I'm the only guy besides Bob I've met who loves to roleplay. Everybody will tell you they hate it, but they really like it, and it makes you better. What you do in a roleplay is exactly what you do with a customer. Practice doesn’t make perfect; it makes it permanent. We're going to roleplay, and I will probably make the first mistake. That levels the playing field, making it okay to be wrong in practice so you can be right with the customer."

In Sum

Small businesses worldwide bring hope to those who leave their day jobs to follow a dream. Those same business owners provide jobs, training, and hope to those who work with them and, in turn, those who shop with them.

Take a bow this week and remember how many people are pulling for you to succeed. Including me.