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Side Hustle to Small Business
Side Hustle to Small Business
Author: Hiscox
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Description
A weekly podcast from Hiscox, the small business insurance experts. We’re changing the conversation around the side hustle and featuring founders at various stages of their small business journey. These entrepreneurs are pushing the envelope while keeping their values and have learned a few lessons along the way. Listen each week for conversation, context, and camaraderie. Hosted by Sanjay Parekh, produced by Edgewise.Media.
202 Episodes
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Katherine Klimitas is the Founder of KAK Art & Designs, which began as a childhood hobby painting animals for her parents’ veterinary clients and has evolved into a thriving business specializing in pet portraits and graphic design. Her innovative approach supports artists and pet lovers alike through personalized artwork and creative design solutions.
In this episode of the Side Hustle to Small Business® Podcast, Katherine shares her inspiring journey from using art as a way to engage during childhood limitations to building a successful creative business. She and host Sanjay discuss turning a passion into profit, developing a unique artistic style, and growing a business centered on creativity and connection.
What You’ll Learn:
• How to turn a personal hobby into a thriving creative business
• Strategies for marketing and selling custom artwork
• Building a brand that connects with clients emotionally
• The story behind KAK Art & Designs and Katherine’s unique artistic journey
Learn more about KAK Art & Designs at https://kakartnola.com/
Chapters:
00:00 Introduction and background
11:10 Building the business and getting clients
15:00 Finding the proper rates
17:00 Setbacks in the business
19:22 Dealing with rejection
21:55 Balancing life and work
23:46 Engaging with community
25:43 Reflecting on the business
28:40 Technology and app suggestions
30:22 Advice for other entrepreneurs
31:49 Closing and contact
#SmallBusiness #art #graphicdesign
At Hiscox, we provide customized insurance solutions for small businesses and entrepreneurs, empowering you to take risks with confidence. With over 100 years of expertise, we offer coverage options like general liability and professional liability, helping you protect what matters most. Learn more at hiscox.com.
Robert Carnes is a freelance copywriter and author who started his copywriting business while working full-time in marketing. What began as a creative outlet has grown into a thriving freelance practice, helping clients craft compelling content and develop their brands.
In this episode of the Side Hustle to Small Business® Podcast, Robert shares his journey from balancing a full-time marketing career with a side hustle to building a successful copywriting business. He and host Sanjay discuss the evolving role of AI in writing, strategies for overcoming imposter syndrome, and the lessons he’s learned as an author and entrepreneur.
What You’ll Learn:
• How to launch a copywriting business alongside full-time work
• Leveraging AI tools to enhance creativity and efficiency
• Building confidence and overcoming imposter syndrome as a writer
• Tips for turning writing skills into multiple revenue streams
Learn more about Robert Carnes at https://www.jamrobcar.com/
Chapters
00:00 Introduction and background
5:52 Scaling the business
8:28 Using automation in the business
10:44 Robert’s authorship
19:37 Work-life balance
23:30 Overcoming nerves
31:47 Closing and contact
At Hiscox, we provide customized insurance solutions for small businesses and entrepreneurs, empowering you to take risks with confidence. With over 100 years of expertise, we offer coverage options like general liability and professional liability, helping you protect what matters most. Learn more at hiscox.com.
After more than a decade leading operations and project management, Keith Williamson decided it was time for a new challenge. He founded Order and Scale Consulting, an agency helping businesses improve project management, workflow design, and team development. In this episode, Keith shares what it’s like to launch a consulting business, why networking matters more than ever, and how putting yourself out there can open new doors.
Chapters
00:00 Introduction and background
6:07 Building the business
17:24 Work-life balance
19:57 Finding clients and networking
29:21 Overcoming nerves
30:39 Closing and contact
Learn more about Keith and Order and Scale Consulting here: https://www.orderandscaleconsulting.com/
#SmallBusiness #podcast #SideHustle
At Hiscox, we provide customized insurance solutions for small businesses and entrepreneurs, empowering you to take risks with confidence. With over 100 years of expertise, we offer coverage options like general liability and professional liability, helping you protect what matters most. Learn more at hiscox.com.
Bradley Taylor is the founder of The Donut Trap, a donut, coffee, and ice cream shop in Saint Paul, Minnesota. After returning home from college in Los Angeles, he noticed the lack of quality donuts in his community and set out to fill that gap. What began as an idea has grown into both a storefront and a donut vending machine. Beyond serving sweets, Bradley is dedicated to empowering Black youth and people of color to explore and pursue entrepreneurship.
Chapters
00:00 Introduction and background
4:37 Building The Donut Trap
7:54 Overcoming nerves
10:41 Opening a storefront
13:01 Expanding into vending machines
18:43 Creating the branding and mission
21:46 Work-life balance
23:25 Staying creative
24:35 Staying involved in the community
26:53 Looking to the future
27:36 Reflecting on the business
29:46 Advice for other entrepreneurs
30:46 Closing and contact
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.
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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




Nice podcast! Just checked you out after hearing about you as a sponsor of The Indicator. 👍