
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 Oct 22, 2025
Sleeping on success: How affiliate links built a business
Wednesday Oct 22, 2025
Wednesday Oct 22, 2025
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

Wednesday Oct 15, 2025
Building and scaling an app: Advice from the WineLikes founder
Wednesday Oct 15, 2025
Wednesday Oct 15, 2025
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

Wednesday Oct 08, 2025
Marketing made simple for contractors and landscapers
Wednesday Oct 08, 2025
Wednesday Oct 08, 2025
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

Wednesday Oct 01, 2025
From pitching products to building a personal brand
Wednesday Oct 01, 2025
Wednesday Oct 01, 2025
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

Wednesday Sep 24, 2025
How to run payroll like a pro
Wednesday Sep 24, 2025
Wednesday Sep 24, 2025
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

Wednesday Sep 17, 2025
How Farmer Nick grew a viral business
Wednesday Sep 17, 2025
Wednesday Sep 17, 2025
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

Wednesday Sep 10, 2025
How the right bookkeeper can boost your growth
Wednesday Sep 10, 2025
Wednesday Sep 10, 2025
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

Wednesday Sep 03, 2025
Saving the shore, one product at a time
Wednesday Sep 03, 2025
Wednesday Sep 03, 2025
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

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
