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PODCAST

Side Hustle to Small Business

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.

business entrepreneurship

All Episodes

30:45

Managing growth across multiple companies

Side Hustle to Small Business ·

2025/10/29

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

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34:12

Sleeping on success: How affiliate links built a...

Side Hustle to Small Business ·

2025/10/22

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

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29:35

Building and scaling an app: Advice from the...

Side Hustle to Small Business ·

2025/10/15

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,

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30:51

Marketing made simple for contractors and landscapers

Side Hustle to Small Business ·

2025/10/08

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

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33:36

From pitching products to building a personal brand

Side Hustle to Small Business ·

2025/10/01

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

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31:52

How to run payroll like a pro

Side Hustle to Small Business ·

2025/09/24

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

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31:00

How Farmer Nick grew a viral business

Side Hustle to Small Business ·

2025/09/17

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

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35:44

How the right bookkeeper can boost your growth

Side Hustle to Small Business ·

2025/09/10

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

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31:10

Saving the shore, one product at a time

Side Hustle to Small Business ·

2025/09/03

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

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32:15

How Cause of a Kind was built by opportunity

Side Hustle to Small Business ·

2025/08/27

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

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29:17

Turning a decades-long hustle into a full-time business

Side Hustle to Small Business ·

2025/08/20

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

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34:30

Building a fashion brand for STEM-loving kids and adults

Side Hustle to Small Business ·

2025/08/13

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

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36:39

Awkward, fun, and profitable: Building a card game brand

Side Hustle to Small Business ·

2025/08/06

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

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35:53

Finding the right price for handmade goods

Side Hustle to Small Business ·

2025/07/30

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

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36:00

Globowl’s mission to make kids’ meals more exciting

Side Hustle to Small Business ·

2025/07/23

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

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35:12

Designing for social impact with Creative Director Jo...

Side Hustle to Small Business ·

2025/07/16

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

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32:40

Managing finances better as a small business owner

Side Hustle to Small Business ·

2025/07/09

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

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27:57

From postpartum to product line: The birth of Le Lolo

Side Hustle to Small Business ·

2025/07/02

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

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33:35

Funding your dream: Crowdfunding advice that works

Side Hustle to Small Business ·

2025/06/25

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

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36:23

A therapist’s guide to copy that connects

Side Hustle to Small Business ·

2025/06/18

After several years working as a licensed psychotherapist, Arianna Smith launched a copywriting side hustle in 2019. Her goal was to help fellow therapists write copy that feels clear, human, and approachable. By simplifying clinical language and focusing on genuine connection, Arianna has grown that side hustle into a thriving business, one that now surpasses her therapy practice.-Chapters- 00:00 Introduction and background 6:55 Finding clients 8:45 Growing a side hustle while working

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185 results

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