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We Asked These Small Business Owners What It's Like To Be Your Own Boss

Supporting small businesses supports your local economy. Shop local this Small Business Week, May 5–11, and join Vistaprint in supporting entrepreneurs in your community.

Ever wondered how small business owners get it done? We asked these inspiring entrepreneurs to share their successes, their failures, and their hard-earned knowledge with us.

1. Headbands of Hope

How did your company start?

Jess: "I started Headbands of Hope when I was in college. I was interning at Make-A-Wish and saw kids losing their hair to chemotherapy and being offered wigs and hats, but instead, wearing headbands. Headbands were a fun way for them to boost their self-confidence without hiding what they’re going through. I did some Google searches to try to find organizations that gave headbands to kids with cancer and came up dry.

"A few weeks prior, Blake Mycoskie, founder of TOMS, spoke at my school and talked about using business as a vehicle for change by offering donations as a part of your business model. The perfect storm of discovering a need and learning about social commerce led me to start Headbands of Hope. For every headband sold, we donate one to a child with cancer."

How has your vision for your company changed from the beginning to now?

Jess: "When I first started Headbands of Hope, I had this vision of giving headbands to kids with cancer, and it has been so incredible to see that come to fruition. But another area of impact that was unexpected was the people I could serve just by using the power of the story behind my business. In addition to running Headbands of Hope, I now speak 60 times a year all over the world about my story of Headbands of Hope and encouraging others to use optimism to create the world they want to live in. I also realized there are so many other women out there with powerful stories too, so I created Mic Drop Workshop, an online course and community to help women get paid to speak.

"It has been amazing to see how many kids we could help through headbands. But it has been a pleasant surprise to see how many people we could help just by telling an honest story."

What’s been your biggest success and your biggest failure?

Jess: "My biggest success was donating headbands to every children’s hospital in America and 15 countries. My biggest failure was losing a $10K loan from a family member when I wired it to a fraudulent manufacturer at the beginning of my business.

"However, that $10K story is the story I tell on stages all over the world as a professional speaker. It took me a while to realize that failure is not what made me unqualified; it’s what made me purposefully resilient. And I like to help people write their own narrative around their own failures and remind them that failures are not opposite of success; they’re just a part of it."

2. The Sweetbay Shop

How did your company start?

Beth: "I started my business a long time ago, when my kids were very little and I wanted to work as a young mother. I started back in the '80s because I loved the florist business, but wanted to be home with my kids."

Liz: "The shop has taken on a whole different vibe in the last three years. Before that it was just my mom: a one-woman show. I swore I wouldn’t do what she did, but after I had my second kid, I needed a creative outlet and I found my own niche in the business... I grew up in the shop waiting on customers as a young child, helping my mom set up at craft shows early in the morning, and more."

What challenges have you faced?

Beth: "As a woman in business there are certain challenges as well. When I was younger, I had trouble getting people to take me seriously. When I started, the flower business was really male-dominated and the opportunities then weren’t as small-business-oriented as they are now either. We’re lucky to have an amazing network of women and moms who work with us."

Liz: "The biggest challenge for both of us is being a mother and a woman business owner and an entrepreneur – you’re expected to do everything and the work–life balance is really challenging. A mom is the backbone of a household and ultimately at some point you do end up sacrificing one for the other (family and business)."

What’s been your biggest success and your biggest failure?

Liz: "Our biggest success is the branding, and we feel really proud about how we have reestablished ourselves in this quick turnaround with the new reincarnation of Sweetbay. My mom left her own brick-and-mortar location for about seven years to join a group of women entrepreneurs and came back home to Wakefield, Massachusetts, to build her business again. We’ve become a destination — people come from pretty far away visit and say, 'I came from Sudbury or Concord or the Cape because I heard about your shop!' We also employ eight people and are really proud of that. We’re passionate about employing people in our community.

"Our biggest 'failure' was not planning for and being able to keep up with the growth of our business, and it’s a great problem to have, but our business has grown dramatically year over year. We opened a second location — it’s not a failure; it’s a challenge. We have to keep asking ourselves: Are we responding to that growth in the right way? Are we buying the right products? Are we aligning with the right partners? … Those are opportunities, and some have gone better than others — am I not being the best mom I could? It’s all about finding a balance, but you can’t always do everything."

3. CommonWealth Kitchen

How did your company start?

Jen Faigel, Executive Director: "CommonWealth Kitchen was originally founded in 2009 (formerly known as CropCircle Kitchen) as a 4,000-square-foot shared-use kitchen in the Jamaica Plain neighborhood of Boston, with a goal of lowering the barriers for people looking to start a food business, with a primary focus on working with women, immigrants, and people of color... Today there are 55 food businesses that call CommonWealth Kitchen home... The majority (75%+) of our companies are owned by women, people of color, and immigrants, and that’s 100% by design. Together, these businesses employ more than 150 people."

What challenges have you faced?

Jen: “As an organization focused on helping launch food businesses that create jobs and address racial, social, and economic inequality, we’ve struggled with a host of different challenges. Navigating the process of permits, packaging, labeling, food safety, distribution, marketing, financing, and everything in between is really challenging. The road map is enormously complex!

"Access to capital is not equitable: Funding is one of the biggest struggles for our diverse companies, most of whom don’t have much money of their own and don’t have the friends and family networks or access to private equity needed to scale a food company. We can provide state of the art kitchens, expert coaching by seasoned chefs, intensive business support, and coordinated access to markets, but if our member businesses can’t access the capital they need to grow the business, they’ll never create viable companies.

"The challenge is compounded by the fact that we’re working in a city where the median net worth for African American households is $8, while household median net worth for whites is $247,500 (according to 2015 report "The Color of Wealth in Boston"). To say the playing field is uneven is a grave understatement.

"Rising rents: For our organization, our entrepreneurs, and the workers that the businesses need, Boston’s rapidly rising residential and commercial rents are a serious barrier to success."

What’s been your biggest success and your biggest failure?

Jen: "We’ve seen some great successes, like seeing member company Jamaica Mi Hungry, founded by chef Ernie Campbell, go from a private chef and catering business, to adding a food truck, a seasonal café, a takeout kiosk, and soon a brick-and-mortar restaurant in less than a decade is phenomenal. Similarly, our awesome lactose-free ice cream company, BECKON, launched nationally across every Whole Foods account in the country this week! Since our founding, we’ve graduated 60 companies into their own dedicated operations that are still in business today. These companies generate a combined revenue of $60 million annually and have created 600 jobs.

"There are also the quieter successes that are less obvious — like the baker who told us, 'I finally began to experience true feelings of authenticity, which allowed me the inner strength and courage to forge ahead with the dream of starting this business. THAT was the struggle for me. Believing that I could.'

"Failure is pretty much a given, whether it’s the cakes that didn’t bake correctly, the labels that were applied upside down, or the food truck whose generator died in the middle of service. Our work is full of constant mistakes. The challenge is staying positive, and always being ready to pivot, bounce, adjust, and always try to learn and have a sense of humor."

What moment made you realize you had created a successful company?

Jen: "In November 2018, we watched a tremendous thing happen in our shared kitchen. We even gave it a name: #piepalooza.

"Two years earlier, mom of three and Dorchester native Teresa Thompson Maynard turned her baking hobby into a full-fledged company and launched Sweet Teez Bakery. Teresa had been producing about 1,000 pies a week when Whole Foods gave her a Purchase Order to sell her famous mini-pies in 40+ stores throughout the North Atlantic region for the holiday. Originally, she had planned an eight-week production schedule to produce 48,000 of her apple, blueberry, and sour cherry pies. But because of funding struggles, she ended up having only four weeks to fill the order. She hired 13 workers who helped her produce an incredible 12,000 pies a week! It was an incredible all hands-on deck moment to get those pies to market on time. Teresa’s fellow entrepreneurs and our staff all chipped in to make it happen — from advice on getting a loan to scaling up a recipe to rolling out pie shells in the kitchen.

"The experience helped Teresa turn her dream from being a baker to becoming a CEO."

4. Jamaica Mi Hungry

How did your company start?

Aquilla, General Manager: "Jamaica Mi Hungry was started by Chef Ernie Campbell. His unique cooking combines his family’s cooking style, the hands-on education he received in the restaurants and resorts of Negril, Jamaica, and the experience he acquired working in large fast-paced kitchens in the United States.

"While living and working in Boston, Ernie realized that the food that he craved — the taste of Jamaica and the distinct taste of his mom’s cooking — was missing in Boston. In 2012, 11 years after coming to the United States, Ernie decided to bring the taste of the island to the mainstream market and launched Jamaica Mi Hungry as a private chef and catering company. The business has grown exponentially ever since."

How did you first promote your unique business?

Aquilla: "The business really grew through word of mouth. In 2013, when the company got its first branded catering van, the mobile advertisement gave us more visibility and really helped to promote the business. We’re honored that our hard work day in and out has started to be recognized beyond our daily lunchtime fans. At the end of 2018, The Boston Globe wrote about our business: 'No doubt, Cantabrigians, and those who work nearby will be clamoring for Campbell’s rice and beans made with jasmine rice and coconut milk, or a pulled jerk pork sandwich. His own spice blend elevates the dishes.'"

How has your vision for your company changed from the beginning to now?

Aquilla: "In the beginning, the vision for the company was just to do small catered events and create a steady income. Once we began to see the potential of the business to grow beyond a catering operation, we worked extremely hard to create something different with a larger vision. Today Jamaica Mi Hungry still runs our original catering business, plus food trucks, a seasonal beachfront café, takeout lunch spot, restaurant (coming in spring 2019), and ultimately bringing Jamaican cuisine to the mainstream market. We are looking forward to expanding regionally and possibly nationally."

When you support small businesses, you support small business owners. Join Vistaprint and shop local this Small Business Week May 5–11.