
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 Dec 31, 2025
RERUN: Bartender Launches Restaurant Empire: Brian Parenteau's Story
Wednesday Dec 31, 2025
Wednesday Dec 31, 2025
Brian Parenteau never planned to work weekends, but bartending sparked his passion for the restaurant industry. Rising through the ranks and gaining experience helping launch new venues, Brian realized it was time to take control and build his own business.
Now the proud owner of four unique restaurants and bars in Florida, Brian shares his candid journey through first-year losses, pandemic pivots, and elevating his concepts to stay ahead in a competitive market. He also offers practical insights into buying versus starting businesses and how staying humble helped him succeed.
If you’re interested in entrepreneurship in the hospitality industry or love stories about turning passion into profit, this episode is a must-watch.
What You’ll Learn:
- How to turn hospitality experience into business ownership
- Pros and cons of buying vs. starting restaurants
- Navigating first-year financial challenges
- Adapting strategies amid a pandemic
- Building a distinct brand with elevated concepts
- Tools and apps that streamline restaurant management
Chapters:
00:00 Introduction & Background
05:13 Humbling Roots
07:55 Buying vs. Starting a Business
10:04 Lessons from First Year Losses
12:42 Pivoting Through the Pandemic
16:14 Creating Elevated & Edgier Concepts
18:14 Bartender to Entrepreneur
23:12 Inspiration from Sam Malone at Cheers
26:20 Embracing Humility
28:45 Best Apps for Restaurateurs
30:07 Closing
#SmallBusiness #Insurance #Side Hustle
At Hiscox, we provide customized insurance solutions for small businesses and entrepreneurs, empowering you to take risks with confidence. With over 100 years of expertise, we offer coverage options like general liability and professional liability, helping you protect what matters most. Learn more at hiscox.com.
Explore inspiring stories and practical advice from entrepreneurs by listening to more episodes of the Side Hustle to Small Business® Podcast: https://www.youtube.com/@HiscoxSmallBusinessInsurance/podcasts

Wednesday Dec 24, 2025
RERUN: How to leverage AI for your small business
Wednesday Dec 24, 2025
Wednesday Dec 24, 2025
Joselyne Walter has seen her fair share of corporate jobs. In these environments, even with large budgets, she found that there was a gap in resources. It was then that she got the idea for The Digg Agency, a marketing agency that helps organizations execute high scale projects. By leveraging AI, Joselyne efficiently scaled her business during its early stages, paving the way for long-term success.
In this episode, you'll learn:
- Incorporating AI into your business
- Having a safety net
- Prioritizing family while growing a business
Chapters
00:00 – Intro
4:44 – Starting The Digg Agency
8:40 – Managing Work-Life Balance
9:50 – Maintaining Exercise Practices
11:55 – The Impact of AI
13:30 – Challenges of Incorporating AI
14:36 – Upcoming Trends and Tools in AI
15:48 – Impact of AI on Teams
16:56 – Reflecting on Past Mistakes
17:56 – Advice from Joselyne
21:31 – Closing & Contact
Learn more at: https://www.thediggagency.com/
#smallbusiness #AI #agency
At Hiscox, we provide customized insurance solutions for small businesses and entrepreneurs, empowering you to take risks with confidence. With over 100 years of expertise, we offer coverage options like general liability and professional liability, helping you protect what matters most. Learn more at hiscox.com.

Wednesday Dec 17, 2025
Aquila Mendez-Valdez scales through franchising and community
Wednesday Dec 17, 2025
Wednesday Dec 17, 2025
00:00 Introduction and background
5:53 Overcoming nerves
11:31 Growing a company culture
13:42 Differentiating your company
17:23 Advice for small businesses
20:12 Scaling the business
24:52 Balancing work and life
30:08 Closing and contact

Wednesday Dec 10, 2025
Patty Durrell transforms physical therapy into a thriving gym
Wednesday Dec 10, 2025
Wednesday Dec 10, 2025
00:00 Introduction and background
5:31 Overcoming nerves
8:25 Finding your first clients
15:14 Surviving COVID
20:33 Balancing work and life
27:31 Reflecting on the business
30:09 Advice for other entrepreneurs
31:01 Closing and contact

Wednesday Dec 03, 2025
Katherine Klimitas built a career from her childhood passion
Wednesday Dec 03, 2025
Wednesday Dec 03, 2025
Katherine Klimitas is the Founder of KAK Art & Designs, which began as a childhood hobby painting animals for her parents’ veterinary clients and has evolved into a thriving business specializing in pet portraits and graphic design. Her innovative approach supports artists and pet lovers alike through personalized artwork and creative design solutions.
In this episode of the Side Hustle to Small Business® Podcast, Katherine shares her inspiring journey from using art as a way to engage during childhood limitations to building a successful creative business. She and host Sanjay discuss turning a passion into profit, developing a unique artistic style, and growing a business centered on creativity and connection.
What You’ll Learn:
• How to turn a personal hobby into a thriving creative business
• Strategies for marketing and selling custom artwork
• Building a brand that connects with clients emotionally
• The story behind KAK Art & Designs and Katherine’s unique artistic journey
Learn more about KAK Art & Designs at https://kakartnola.com/
Chapters:
00:00 Introduction and background
11:10 Building the business and getting clients
15:00 Finding the proper rates
17:00 Setbacks in the business
19:22 Dealing with rejection
21:55 Balancing life and work
23:46 Engaging with community
25:43 Reflecting on the business
28:40 Technology and app suggestions
30:22 Advice for other entrepreneurs
31:49 Closing and contact
#SmallBusiness #art #graphicdesign
At Hiscox, we provide customized insurance solutions for small businesses and entrepreneurs, empowering you to take risks with confidence. With over 100 years of expertise, we offer coverage options like general liability and professional liability, helping you protect what matters most. Learn more at hiscox.com.

Wednesday Nov 26, 2025
Robert Carnes grows a freelance writing business while working in marketing
Wednesday Nov 26, 2025
Wednesday Nov 26, 2025
00:00 Introduction and background
5:52 Scaling the business
8:28 Using automation in the business
10:44 Robert’s authorship
19:37 Work-life balance
23:30 Overcoming nerves
31:47 Closing and contact
At Hiscox, we provide customized insurance solutions for small businesses and entrepreneurs, empowering you to take risks with confidence. With over 100 years of expertise, we offer coverage options like general liability and professional liability, helping you protect what matters most. Learn more at hiscox.com.

Wednesday Nov 19, 2025
The importance of networking in small business
Wednesday Nov 19, 2025
Wednesday Nov 19, 2025
After more than a decade leading operations and project management, Keith Williamson decided it was time for a new challenge. He founded Order and Scale Consulting, an agency helping businesses improve project management, workflow design, and team development. In this episode, Keith shares what it’s like to launch a consulting business, why networking matters more than ever, and how putting yourself out there can open new doors.
Chapters
00:00 Introduction and background
6:07 Building the business
17:24 Work-life balance
19:57 Finding clients and networking
29:21 Overcoming nerves
30:39 Closing and contact
Learn more about Keith and Order and Scale Consulting here: https://www.orderandscaleconsulting.com/
#SmallBusiness #podcast #SideHustle
At Hiscox, we provide customized insurance solutions for small businesses and entrepreneurs, empowering you to take risks with confidence. With over 100 years of expertise, we offer coverage options like general liability and professional liability, helping you protect what matters most. Learn more at hiscox.com.

Wednesday Nov 12, 2025
Building The Donut Trap from scratch
Wednesday Nov 12, 2025
Wednesday Nov 12, 2025
Bradley Taylor is the founder of The Donut Trap, a donut, coffee, and ice cream shop in Saint Paul, Minnesota. After returning home from college in Los Angeles, he noticed the lack of quality donuts in his community and set out to fill that gap. What began as an idea has grown into both a storefront and a donut vending machine. Beyond serving sweets, Bradley is dedicated to empowering Black youth and people of color to explore and pursue entrepreneurship.
Chapters
00:00 Introduction and background
4:37 Building The Donut Trap
7:54 Overcoming nerves
10:41 Opening a storefront
13:01 Expanding into vending machines
18:43 Creating the branding and mission
21:46 Work-life balance
23:25 Staying creative
24:35 Staying involved in the community
26:53 Looking to the future
27:36 Reflecting on the business
29:46 Advice for other entrepreneurs
30:46 Closing and contact

Wednesday Nov 05, 2025
Inside the proposal planning business
Wednesday Nov 05, 2025
Wednesday Nov 05, 2025
Ash Fox is a New York City–based proposal planner and photographer. With a background in fine arts, she began her career taking on freelance commercial photography projects while still in college, which soon opened doors into nightlife and music photography. Everything shifted when she was asked to capture a proposal, an experience that sparked her passion for photographing and also planning unforgettable moments.
Chapters
00:00 Introduction and background
8:03 Proposal tips
15:38 Overcoming nerves
17:55 Marketing your business
20:40 Expanding the business
23:04 Work-life balance
26:41 Reflecting on the business
30:08 Advice for other entrepreneurs
31:22 Closing and contact
Learn more about Ash Fox and her work at https://www.ashfoxproposals.com
Side Hustle to Small Business is presented by Hiscox, a leading small business insurer. Learn more at Hiscox.com
#Entrepreneurship #SmallBusiness #WeddingBusiness

Wednesday Oct 29, 2025
Managing growth across multiple companies
Wednesday Oct 29, 2025
Wednesday Oct 29, 2025
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 Managing the business
16:39 Work-life balance
21:40 Motherhood and entrepreneurship
23:57 Reflecting on the business
28:06 Advice for other entrepreneurs
29:44 Closing and contact
