
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

4 days ago
4 days ago
00:00 Introduction and background
5:30 Starting the business
13:53 Maintaining multiple businesses
20:12 Overcoming nerves
21:50 Hiring
24:55 Balancing work and life
28:35 Advice for other entrepreneurs
30:17 Reflecting on the business
31:49 Closing and contact

Wednesday Jan 28, 2026
Rachel Lundberg leads Thrive Yoga and Wellness through community building
Wednesday Jan 28, 2026
Wednesday Jan 28, 2026
00:00 Introduction
2:18 Buying an existing business
8:15 Rachel’s yoga background
10:43 Shifting roles
18:09 Successes and failures
23:57 Exercise and wellness
26:16 Reflecting on the business
27:58 Closing and contact

Wednesday Jan 21, 2026
Jodi Peterman builds a client-focused interior design practice
Wednesday Jan 21, 2026
Wednesday Jan 21, 2026
00:00 Opening and introduction
8:16 Finding the right client
16:57 Pleasing your clients
19:48 Staying in budget
21:03 Balancing life and work
23:39 Balancing offices across the country
26:44 Advice for other entrepreneurs
28:05 Closing and contact

Wednesday Jan 14, 2026
Lesle Lane expands a family enterprise
Wednesday Jan 14, 2026
Wednesday Jan 14, 2026
00:00 Introduction and Background
7:28 Taking over a family business
11:49 Maintaining family legacy
14:00 Shifting the business’s focus
15:50 Expanding the business
18:55 Incorporating AI into the business
23:43 Work-life balance
28:43 Reflecting on the business
30:43 Advice for other entrepreneurs
31:55 Closing and contact

Wednesday Jan 07, 2026
Miriam Schulman built a life around her creative work
Wednesday Jan 07, 2026
Wednesday Jan 07, 2026
00:00 Introduction and background
8:30 Overcoming nerves
12:00 Building a coaching business
15:33 Challenges artists face
19:42 Balancing life and work
25:58 Incorporating AI into your business
27:55 Reflecting on the business
29:55 Advice for other entrepreneurs
30:32 Closing and contact

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.
