Ash Fox is a New York City–based proposal planner and photographer. With a background in fine arts, she began her career taking on freelance commercial photography projects while still in college, which soon opened doors into nightlife and music photography. Everything shifted when she was asked to capture a proposal, an experience that sparked her passion for photographing and also planning unforgettable moments.   Chapters 00:00 Introduction and background 8:03 Proposal tips 15:38 Overcoming nerves 17:55 Marketing your business 20:40 Expanding the business 23:04 Work-life balance 26:41 Reflecting on the business 30:08 Advice for other entrepreneurs 31:22 Closing and contact   Learn more about Ash Fox and her work at https://www.ashfoxproposals.com Side Hustle to Small Business is presented by Hiscox, a leading small business insurer. Learn more at Hiscox.com #Entrepreneurship #SmallBusiness #WeddingBusiness

Amy Anaiz has spent over 25 years building a career as a professional photographer. When the pandemic paused events and disrupted her usual work, she saw an opportunity to explore new creative ventures. That’s when she founded OZAIZ, a homewares brand born from the idea of making candles last beyond a single use. Today, Amy balances running OZAIZ alongside her established photography business, all while raising a family.   Chapters 00:00 Introduction and background 9:40 Marketing the company 12:17 Managing the business 16:39 Work-life balance 21:40 Motherhood and entrepreneurship 23:57 Reflecting on the business 28:06 Advice for other entrepreneurs 29:44 Closing and contact

Derek Hales was working in marketing and SEO when he and his wife set out to buy a new mattress. Frustrated by how hard it was to choose the right one, he launched a side project comparing mattresses. What began as a hobby quickly grew into NapLab, a mattress-review company that uses scientific data to break down mattress performance and help people make smarter buying decisions.   Chapters 00:00 Introduction and background 6:43 Overcoming nerves 7:52 Revenue from review sites 13:11 Building the testing model 14:58 Hiring practices and scaling 19:26 Work-life balance 24:17 Helpful technology and apps 27:45 Reflecting on the business 31:58 Advice for other entrepreneurs 32:56 Closing and contact   Learn more about Derek Hales and NapLab: https://naplab.com

Jeff Gillis, founder of WineLikes, turned his lifelong passion for wine into a tech startup designed to change how people discover their next bottle. After years in the hospitality industry, Jeff realized the demanding lifestyle no longer fit the parent he wanted to be. Inspired to build something different, he created WineLikes, a social app that connects wine lovers, makes recommendations easier, and helps people enjoy wine without the overwhelm. In this episode, Jeff shares how he built the app, the role of technology in modern wine culture, and how he balances entrepreneurship with family life.   Chapters 00:00 Introduction and background 5:12 Building the app 9:50 Balancing life and work 15:46 Running social media for the company 17:17 Technology and apps 24:00 Advice for others in the industry 25:29 Advice for other entrepreneurs 28:21 Closing and contact

Josh Blakeley began his career in teaching before moving from Australia to the United States. After coming across an ad for a digital marketing course, his curiosity got the better of him and he decided to enrol. That decision set him on a new path. Today, Josh is the founder of Landscape & Hardscape Contractor Marketing, a firm dedicated to helping contractors and landscapers grow their businesses.   Chapters 00:00 Introduction and background 9:56 Choosing a niche 12:33 Pitching yourself to clients 14:47 Josh’s book 19:17 Balancing life and work 26:38 Reflecting on the business 28:10 Advice for other entrepreneurs 29:15 Closing and contact

Merit Khan has been an entrepreneur for as long as she can remember. Her first taste of business came as a young girl selling greeting cards door-to-door, an early lesson in the power of connecting with people. Over the years, that spark grew into a full-fledged career built on her ability to engage, inspire, and persuade. Today, Merit is not only a successful entrepreneur but also a sought-after keynote speaker, accomplished sales trainer, and stand-up comedian.    Chapters 00:00 Introduction and Background 14:34 Starting the business 16:16 Overcoming nerves 27:09 Health and Wellness 30:25 Reflecting on the business 31:59 Closing and contact

Payroll is one of the trickiest parts of running a business, but for Christina Hageny, it became her calling. She first discovered payroll while working as an administrative assistant, and despite encouragement to move into HR, she stuck with it. In 2020, Christina launched her own firm, Valor Payroll Solutions, and today she helps small businesses handle payroll with ease and confidence.   Chapters 00:00 Introduction and background 11:19 Payroll across different industries 13:31 Scaling the business  17:58 Bootstrapping the business 20:34 Balancing work and life 25:32 Reflecting on the business 29:39 Advice for other entrepreneurs  30:39 Closing and contact

Garden guru Nick Cutsumpas, better known as Farmer Nick, is a Michigan-based plant coach, urban gardener, and landscape designer. He talks about how his mom encouraged him to start a garden, sparking a deep love for greenery that quickly blossomed into a full-time career and an impressive social media following. He hosts several Netflix shows and has been featured on the Food Network.   Chapters 00:00 Introduction and background 5:27 Overcoming nerves 8:15 Creating Farmer Nick 14:33 Managing a large business 19:49 Cause-based marketing 21:38 Building a National business 26:47 Reflecting on the business 29:18 Advice for other entrepreneurs 29:56 Closing and contact

Matt Remuzzi entered the accounting industry twenty-five years ago when he founded CapForge. What began as a solo venture launched from a spare bedroom in his home has since evolved into a thriving business. Today, CapForge employs a team of over 90 people who help more than a thousand clients grow their businesses and meet their obligations with professional bookkeeping support.   Chapters 00:00 Introduction and background 13:30 Overcoming nerves 17:34 Maintaining quality while scaling 20:03 Pricing 23:27 Work-life balance 29:39 Reflecting on the business 31:48 Advice for other entrepreneurs 34:05 Closing and contact

Cat Lepetit has always had a deep love for the beach. After spending 20 years in the cosmetics industry, she felt it was time for a new chapter. That’s when the idea for Sun Drunk was born, a beach goods company focused on simplicity, peace of mind, and sustainability. With a mission to help protect our oceans and keep beaches clean, Sun Drunk is all about making it easier to enjoy the coast while caring for it too.   Chapters 00:00 Introduction and background 7:48 Overcoming nerves 11:23 Designing the products 16:23 Building a customer base 19:56 Giving back 22:25 Overcoming stress 25:32 Looking back 28:02 Advice for other entrepreneurs  29:57 Closing and contact

Justin Abrams is a lifelong salesman, with a career in the industry spanning over a decade. However, when Justin and his friend Michael tried to pivot into the tech startup space, they found they were facing challenges getting into market. It was at that point that the two were asked to design a web application. This opportunity turned into what would become Cause of a Kind, a successful web development company.   Chapters 00:00 Introduction and Background 8:22 Overcoming nerves 11:25 Building the business 14:52 Using AI 19:23 Balancing life and work 26:26 Advice for other entrepreneurs 30:23 Closing and contact

Nikky Wainwright has been reselling anything since she was in college - books, clothing, shoes, you name it. However in 2020, in the midst of the pandemic, she noticed that while some businesses were suffering, reselling was going strong. It was at this point that she went all in on Diva’s Treasure Closet, a a luxury, designer, and vintage e-commerce business. Starting out online, Nikky has now opened her own boutique in Atlanta.    Chapters 00:00 Introduction and background 6:46 Choosing your inventory 10:38 Social media strategy 15:50 Balancing life and work 20:24 Growing the business 22:53 Reflecting on the business 25:19 Advice for other entrepreneurs 27:42 Closing and contact

When Jaya Iyer couldn’t find science-themed dresses for her daughter, she realized that other parents must be feeling the frustration. Wanting to empower her daughter and others, she launched Svaha USA, a STEAM-based fashion brand that creates clothing for the entire family. What started as a mission to challenge gender stereotypes in kids' clothing has grown into a thriving business known for its bold, brainy designs.   Chapters 00:00 Introduction and background 7:00 Challenges when starting the business 14:13 Creating the clothing 20:30 Fulfilling orders 23:18 Building a mission-driven brand 25:31 Balancing family and work 30:16 Reflecting on the business 31:34 Advice for other entrepreneurs 33:11 Closing and contact

Brittane Rowe is an off-Broadway actress by trade, but when the COVID-19 pandemic shut down Broadway, she found herself with time for deeper, more meaningful conversations with her family. Inspired by those moments, Brittane teamed up with her brother Brandon and sister-in-law Jane to create Awkward Games, a card game company designed to spark joy and strengthen relationships. \ Chapters 00:00 Introduction and background 8:10 Getting the first sales 9:31 Getting the product into stores 11:56 Overcoming nerves 14:48 Shark Tank 24:09 Game development 26:40 Balancing work and life 28:50 Running the business in NYC 31:43 Reflecting back on the business 34:07 Advice for other entrepreneurs 35:28 Closing and contact

Kwadwo Som-Pimpong founded Crafted Glory, a handcrafted furniture company, after buying his first home in Asheville, North Carolina. Drawing on his engineering background, he mastered the mechanics of furniture making and honed his craft. What began as a personal project has grown into a business that serves customers across the country. Today, Crafted Glory is known for its commitment to quality, craftsmanship, and thoughtful design.   -Chapters- 00:00 Introduction and background 6:29 Overcoming nerves 8:12 Pricing your work 10:22 Training as a woodworker  16:30 Viewing the business longterm  20:56 Balancing work and life 25:31 Finding a coach 31:50 Reflecting on the business 33:18 Advice for other entrepreneurs 34:37 Closing and contact

Erica Levin is a serial entrepreneur, having started three businesses in her life. During the pandemic, while her daughter was starting to eat solid foods, Erica decided to start making her own baby food that incorporated flavors from around the world and introduced allergens early. From there, she has built Globowl, a baby and toddler food company with a mission to inspire adventurous eating for life.   -Chapters- 00:00 Introduction and background 4:45 Starting Global 12:05 Overcoming nerves 13:05 Funding the business 16:23 Making mistakes 20:55 Entering the food space 23:41 Plans to grow the business 27:02 Mission-oriented brands 29:02 Work-life balance 32:25 Reflecting on the business 34:47 Closing and contact

Jo Skillman is a Houston-based Creative Director and the Founder of Jo Skillman LLC. Known for her thoughtful, cause-driven work, she’s partnered with clients like the City of Houston. With expertise in both design and copywriting, Jo brings a well-rounded, strategic approach to every project.   -Chapters- 00:00 Introduction and background 6:35 Overcoming nerves 13:20 Working across multiple industries  18:21 Balancing two sides of the business 21:44 Using AI in your work 25:58 Balancing work and life 29:20 Reflecting back on the business 31:18 Advice for other entrepreneurs 33:20 Closing and contact

Jennifer Bower is a mom of two, a veteran, grad student, and the Founder of Fortuna Money. After a career in the Air Force, Jennifer got into the banking world which gave her the knowledge and know how to launch Fortuna Money, a financial coaching service. On this episode, she shares tips and tricks on how small businesses can better manage their money, identifying bad spending habits, and keeping personal and business expenses separate.    -Chapters- 00:00 Introduction and background 5:54 Building the business 11:48 Overcoming nerves 13:31 Choosing the right clients  20:25 Financial mistakes as Founders 22:26 Work-life balance 25:37 Reflecting on the business 28:20 Advice for other entrepreneurs 30:55 Closing and contact

After the birth of her first child, Courtney Boylan quickly discovered that postpartum essentials, such as nipple shields and nursing pads, were typically not made with aesthetics in mind. She believed that with everything that mothers were going through postpartum, they deserved beautiful products. It was then that she founded Le Lolo, a postpartum brand thoughtfully designed to support and celebrate new mothers.   -Chapters- 00:00 Introduction and Background 9:43 Overcoming nerves 11:17 Designing the right product 14:19 Naming the company 16:01 Brand evolution 18:24 Running the business 21:09 Setting boundaries 23:36 Reflecting on the business 26:05 Advice for other entrepreneurs 26:43 Closing and contact

Kathleen Minogue is a creative at heart and a former educator who never imagined a future in finance. But during the dot-com boom, an unexpected opportunity at JP Morgan changed her trajectory. While working there, she noticed a striking gap: those seeking venture capital rarely came from creative fields. It wasn’t until she helped crowdfund a film she produced that she discovered the power of crowdfunding and found her true calling.   -Chapters- 00:00 Introduction and background 5:31 Entrepreneurial background 7:03 Overcoming nerves 10:12 Going from side hustle to small business 20:06 Mistakes in crowdfunding 23:34 Setting boundaries 25:55 Reflecting back on the business 31:05 Advice for other entrepreneurs 32:03 Closing and contact