
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.
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.
Episodes

Wednesday Aug 27, 2025
How Cause of a Kind was built by opportunity
Wednesday Aug 27, 2025
Wednesday Aug 27, 2025
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

Wednesday Aug 20, 2025
Turning a decades-long hustle into a full-time business
Wednesday Aug 20, 2025
Wednesday Aug 20, 2025
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

Wednesday Aug 13, 2025
Building a fashion brand for STEM-loving kids and adults
Wednesday Aug 13, 2025
Wednesday Aug 13, 2025
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

Wednesday Aug 06, 2025
Awkward, fun, and profitable: Building a card game brand
Wednesday Aug 06, 2025
Wednesday Aug 06, 2025
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

Wednesday Jul 30, 2025
Finding the right price for handmade goods
Wednesday Jul 30, 2025
Wednesday Jul 30, 2025
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

Wednesday Jul 23, 2025
Globowl’s mission to make kids’ meals more exciting
Wednesday Jul 23, 2025
Wednesday Jul 23, 2025
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

Wednesday Jul 16, 2025
Designing for social impact with Creative Director Jo Skillman
Wednesday Jul 16, 2025
Wednesday Jul 16, 2025
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

Wednesday Jul 09, 2025
Managing finances better as a small business owner
Wednesday Jul 09, 2025
Wednesday Jul 09, 2025
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

Wednesday Jul 02, 2025
From postpartum to product line: The birth of Le Lolo
Wednesday Jul 02, 2025
Wednesday Jul 02, 2025
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

Wednesday Jun 25, 2025
Funding your dream: Crowdfunding advice that works
Wednesday Jun 25, 2025
Wednesday Jun 25, 2025
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
