Hiscox

Side Hustle to Small Business

Business EN ↓ 100 episodes

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.

Author

Hiscox

Category

Business

Podcast website

www.hiscox.com

Latest episode

Apr 8, 2026

Where to listen?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android 5M+ downloads · 4.8 rating iOS soon

Episodes

From pitching products to building a personal brand 01.10.2025

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...

How to run payroll like a pro 24.09.2025

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.   Chapte...

How Farmer Nick grew a viral business 17.09.2025

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 0...

How the right bookkeeper can boost your growth 10.09.2025

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...

Saving the shore, one product at a time 03.09.2025

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...

How Cause of a Kind was built by opportunity 27.08.2025

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 devel...

Turning a decades-long hustle into a full-time business 20.08.2025

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 op...

Building a fashion brand for STEM-loving kids and adults 13.08.2025

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...

Awkward, fun, and profitable: Building a card game brand 06.08.2025

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. \ Chapters 00:00 Int...

Finding the right price for handmade goods 30.07.2025

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,...

Globowl’s mission to make kids’ meals more exciting 23.07.2025

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...

Designing for social impact with Creative Director Jo Skillman 16.07.2025

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 indus...

Managing finances better as a small business owner 09.07.2025

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...

From postpartum to product line: The birth of Le Lolo 02.07.2025

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 celeb...

Funding your dream: Crowdfunding advice that works 25.06.2025

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 cro...

A therapist’s guide to copy that connects 18.06.2025

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...

Smarter training for small businesses with Dr. Carrie Graham 11.06.2025

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 busines...

Organizing a life you love with D’Nai Walker 04.06.2025

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:...

Tape it until you make it: Solving a sticky problem 28.05.2025

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 7:1...

Turning your creative outlet into profit 21.05.2025

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 fr...

How Ethan Bull redefined the Executive Assistant world 14.05.2025

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...

How to hit a hole-in-one with your side hustle 07.05.2025

While browsing the Golf subreddit, David Paxton saw a lot of people posting deals on golf gear. Looking through these deals was fun, but it was also time-consuming if you were looking for a specific item. So Paxton created Daily Golf Steals, automating the deals to help golfers find what they wanted faster. He still runs the business as a side hustle while working a full-time job.   -Chapters- 00:...

Failing up: From frustration to success 30.04.2025

Kris Louis entered the world of audio/visual by chance while job hunting during the 2008 recession. After several years in the industry, his frustration with the way his employer operated pushed him to take the leap of quitting to start his own successful AV company. Kris credits failure for shaping his journey, teaching him to stay open to multiple paths rather than limiting himself to a single d...

Learn how to scale your small business 23.04.2025

Rachel Donnelly was just starting her career and raising two small children when her parents passed on. As she struggled with settling estates, bank accounts, and other various paperwork, she knew there had to be a better way. It was at this time that Rachel thought of the idea for After Light, an end-of-life and legacy planning service. With six years under her belt, Rachel has now written the bo...

Mastering productivity for your small business 16.04.2025

Monisha Longacre has many titles. She is an author, a fractional COO at two different companies, and the founder of priorigami, a productivity app aimed at helping entrepreneurs be the most productive they can be. As an expert in productivity, Monisha shares her insights on timeblocking, managing multiple roles, and being transparent with your employees. Monisha is the author of "Practical Product...

Listen to the Side Hustle to Small Business podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.