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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.
192 Episodes
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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
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
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 full-time
14:46 Why this business is essential
18:01 Balancing a side hustle
21:14 Expanding the business
23:50 Advice for clients
27:15 Structure of the business
30:15 Reflecting on the business
33:47 Advice for other entrepreneurs
35:04 Closing and contact
With a background in college athletics and academia, Dr. Carrie Graham pivoted her career after earning her Ph.D. in Adult Education. As a professional, she had attended many training programs, and realized that these programs were lacking any sort of personalization to the attendees. It was then that she became an Adult Learning Strategist and Consultant, who specializes in helping small businesses creating more engaging and tailor-made training programs.
-Chapters-
00:00 Introduction
4:50 Starting the business
9:50 Overcoming nerves
11:32 Identifying effective training
16:06 Treating your employees right
19:24 Using training to develop company culture
23:10 Finding your first client
25:14 The future of the business
27:18 Reflecting back on the business
30:24 Advice for other entrepreneurs
31:21 Closing and contact
D’Nai Walker is not a naturally organized person. It wasn’t until she discovered professional organizer Marie Kondo that she got into the practice. When she was laid off, she started doing it on the side, until she was encouraged to go all in. She founded D'Clutter by D'Nai, an organizing company that specializes in senior downsizing, home organization, and productivity solutions.
-Chapters-
00:00 Intro
5:52 Overcoming nerves
7:49 Determining your path
8:31 Finding your first clients
10:04 Navigating client work
13:58 Marketing tools
16:41 Staying organized in your small business
20:52 Setting boundaries
22:53 Health and Wellness
26:08 Technology and apps
27:37 Reflecting on the business
29:21 Advice
30:25 Closing and contact
Doug Bard and his father, Bob, have been inventing for most of their lives. However, their greatest idea yet is that of tape. Specifically, moving tape where you can always find the end of the roll. It’s called Wave Tape. Now, as they reimagine a simple solution to a universal issue, the duo is continuing to find success in the market.
-Chapters-
00:00 Intro
6:02 - Entrepreneurial background
7:17 The history of Wave Tape
11:25 Sales and distribution
18:14 Overcoming nerves
19:28 Balancing full time work with a side hustle
21:48 Exercise routines
22:53 Helpful technology and apps
23:53 Marketing the product
27:34 Long term vision
29:19 Reflecting back on the business
30:22 Advice for other entrepreneurs
31:18 Closing and contact
Jordan Lawson has always loved drawing, coloring, and creating art as a whole. When he was in college, he was inspired by an art entrepreneurship class to start his own business. However, when he graduated, he started working for the government instead. After nine years there, he was ready to make the leap. Jordan founded Ground Zero Studios, a branding studio that helps organizations stand out from their competition.
-Chapters-
00:00 Intro
7:26 Overcoming nerves
11:36 Making the leap into entrepreneurship
14:16 Building a branding studio
18:37 Getting clients
22:31 Managing stress
25:11 Using AI as an artist
28:39 Reflecting back on the business
30:34 Closing and contact
After spending many years as an Executive Assistant, Ethan Bull unexpectedly faced layoffs, forcing him to reconsider his career path. With his severance package as a financial cushion, Ethan and his wife, Stephanie, launched ProAssisting, a fractional EA company. Their business focuses on connecting highly skilled EAs with top-level executives, offering flexible, high-quality support without the need for a full-time hire.
-Chapters-
00:00 Intro
4:32 Entrepreneurial background
6:35 Starting ProAssisting
14:51 Keeping up with technology
16:16 Using AI in the company
19:44 Delegating tasks to an assistant
22:16 The future of the business
28:17 Work-life balance
31:51 Looking back on the business
34:27 Advice to other entrepreneurs
36:23 Closing and contact
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