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Side Hustle to Small Business
Side Hustle to Small Business
Author: Hiscox
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Description
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.
209 Episodes
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Jodi Peterman is the owner of Elizabeth Erin Designs, a full-service interior design firm known for creating timeless, functional spaces tailored to each client’s lifestyle. What began as Jodi’s passion for design has grown into a respected business serving clients with a commitment to exceptional service and practical, elegant solutions.
In this episode of the Side Hustle to Small Business® Podcast, Jodi shares her journey as a design founder and entrepreneur. She and Sanjay discuss how to choose the right interior designer, the importance of staying within budget, and the realities of balancing business ownership with maintaining mental health and managing stress.
What You’ll Learn:
• How to evaluate and select the right interior designer for your project
• Strategies for creating beautiful spaces without going over budget
• What it takes to grow and manage a successful design business
• How entrepreneurs can maintain balance, reduce stress, and protect their well-being
Learn more about Elizabeth Erin Designs at https://elizabetherindesigns.com
Chapters:
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
#SmallBusiness #InteriorDesign #HomeDesign
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.
Lesle Lane is the third-generation owner of Studio 13 Corporate Photography, which began as a family business founded by her grandparents and has evolved into a respected photography studio known for its craft, consistency, and client-focused approach. Her leadership continues a legacy built over decades, with a focus on adapting to new technologies while honoring the studio’s original artistic vision.
In this episode, Lesle shares her inspiring journey from taking over the studio in 1992 to navigating the challenges of running a multi-generational business. She and host Sanjay discuss how youth sports can lay the foundation for entrepreneurship, how to maintain quality and consistency as you hire, and what it takes to preserve a legacy while continuing to grow.
What you’ll learn:
• How to successfully lead and evolve a multi-generational family business
• The connection between youth sports and entrepreneurial resilience
• Strategies for maintaining quality and consistency when hiring
• The story behind Studio 13 Photography’s long-term success
Learn more about Studio 13 Corporate Photography at https://www.studio13online.com/
Chapters:
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
#SmallBusiness #Photography #Podcast
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.
Miriam Schulman is the Founder of Schulman Art, which began as a resource for creative entrepreneurs and has evolved into a comprehensive coaching service helping artists turn their talents into sustainable businesses. Her innovative approach supports artists’ success through mentorship, educational resources, and community-building.
In this episode of the Side Hustle to Small Business® Podcast, Miriam shares her inspiring journey from working in corporate finance to launching Schulman Art. She and host Sanjay discuss monetizing creativity, building supportive communities for artists, overcoming challenges as a creative entrepreneur, and her book "Artpreneur".
What You’ll Learn:
• How to transform a creative passion into a sustainable business
• Strategies for monetizing and marketing artistic work
• Building supportive communities for creative entrepreneurs
• The story behind launching Artpreneur and empowering artists
Learn more about Miriam and Schulman Art at https://www.schulmanart.com/
Chapters:
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
#SmallBusiness #SideHustle #art
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
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.
Aquila Mendez-Valdez is the Founder of Haute in Texas, which began as a personal blog and has evolved into a full-service public relations agency empowering women-led businesses. Her innovative approach combines storytelling, strategy, and community to help brands grow with authenticity and purpose.
In this episode, Aquila shares her inspiring journey from launching a business while pregnant to scaling her company into a thriving agency. She and Sanjay discuss hiring your first employee, creating a franchise model, and the importance of surrounding yourself with a strong, supportive community.
What You’ll Learn:
• How to build a business while balancing family and entrepreneurship
• When and how to hire your first employee
• What it takes to develop a franchise model
• The power of community in sustaining business growth
Learn more about Haute in Texas at https://hitpr.com/
Chapters
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
#SmallBusiness #PublicRelations #Podcast
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.
Patty Durrell is a Physical Therapist and the Founder of Rock Solid Fitness, based in Dunedin, Florida. Having seen gyms close around her while working with clients in other facilities, she decided to open Rock Solid Fitness to create a sustainable, client-focused environment. Her innovative approach combines expert physical therapy with fitness training, supporting clients’ long-term health and performance.
In this episode of the Side Hustle to Small Business® Podcast, Patty shares
the challenges of running a gym during COVID-19, training and empowering staff, and her thoughts on business partnerships.
What You’ll Learn:
• Strategies for managing and growing a fitness business
• Training staff to provide consistent, high-quality client experiences
• How Patty overcame the challenges of running a gym during a pandemic
• Building successful community connections
Learn more about Rock Solid Fitness at https://www.rocksolidfitnessfl.com/
Chapters:
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
#Fitness #Entrepreneurship #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.
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.
Robert Carnes is a freelance copywriter and author who started his copywriting business while working full-time in marketing. What began as a creative outlet has grown into a thriving freelance practice, helping clients craft compelling content and develop their brands.
In this episode of the Side Hustle to Small Business® Podcast, Robert shares his journey from balancing a full-time marketing career with a side hustle to building a successful copywriting business. He and host Sanjay discuss the evolving role of AI in writing, strategies for overcoming imposter syndrome, and the lessons he’s learned as an author and entrepreneur.
What You’ll Learn:
• How to launch a copywriting business alongside full-time work
• Leveraging AI tools to enhance creativity and efficiency
• Building confidence and overcoming imposter syndrome as a writer
• Tips for turning writing skills into multiple revenue streams
Learn more about Robert Carnes at https://www.jamrobcar.com/
Chapters
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.
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.
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
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
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
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
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
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
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
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
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
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
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




Nice podcast! Just checked you out after hearing about you as a sponsor of The Indicator. 👍