Side Hustle to Small Business

Hiscox
  • 4.8 (155)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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.

  1. 2D AGO

    Greg Cantori builds an accessibility business from nonprofit roots

    In this episode, Sanjay speaks with Greg Cantori, founder of Little Deeds Accessibility Solutions, about how his background in the nonprofit sector led him into the construction space, and ultimately to building a growing accessibility-focused business.   Greg shares how years of working in nonprofits shaped his understanding of impact, why accessibility for older adults is both a social need and a business opportunity, and how simple home modifications, like installing shower grab bars, can dramatically improve quality of life.   What you’ll learn: • How nonprofit experience can translate into strong entrepreneurial skills • Why accessibility is an increasingly important (and underserved) market • How to move from service work to a scalable business model • What it takes to expand a local business into a national service • How purpose and profitability can coexist     Chapters  00:00 Introduction 4:02 Building Little Deeds 8:51 Scaling revenue 16:30 Moving internationally while running a business 27:16 Reflecting on the business 29:22 Advice for other entrepreneurs 30:44 Closing and contact   Learn more about Little Deeds Accessibility Solutions at littledeeds.com   At Hiscox, we believe in supporting entrepreneurs who bring bold ideas and strong communities to life. Explore resources and coverage options to help protect and grow your business at Hiscox.com.   #entrepreneurship #accessibility #nonprofit

    32 min

  2. FEB 4

    Marisol Colette on merging her two passions into one business

    In this episode, Marisol Colette, founder of Sol Reflections, shares how she combined two seemingly different passions, therapy and fashion styling, into a single, transformative business. Tune in as Sanjay and Marisol discuss how she approached pricing her services, what it took to hire a full-time employee for the first time, and how she built a model that supports both personal expression and emotional wellbeing.   Whether you’re growing a service-based business or trying to merge multiple passions into one career, this conversation offers practical insight and honest reflection.   What you’ll learn: • How Marisol combined therapy and fashion into one aligned business • How she approached pricing when her services evolved • What founders should know before hiring their first full-time employee • The mindset shifts that help creatives build sustainable businesses • How personal identity and entrepreneurship connect   Chapters: 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   Learn more about Marisol Colette and Sol Reflections: solreflection.com      #entrepreneurship #smallbusiness #womeninbusiness    At Hiscox, we believe in supporting entrepreneurs who bring bold ideas and strong communities to life. Explore resources and coverage options to help protect and grow your business at Hiscox.com.

    33 min

  3. JAN 28

    Rachel Lundberg leads Thrive Yoga and Wellness through community building

    Rachel Lundberg is the founder of Thrive Yoga and Wellness in Oregon City, Oregon, a wellness center that aims to reconnect and nourish your body and mind. Rachel and Sanjay discuss her early journey into yoga, her approach to building a supportive and inclusive studio environment, and why community connection is essential for long-term success in the wellness industry.   What you’ll learn: • How Rachel transitioned into ownership at Thrive Yoga and Wellness • Why community plays a central role in wellness-based businesses • How early personal experiences can shape an entrepreneurial path • Practical lessons for growing a mission-driven yoga or wellness studio   Chapters: 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   Learn more about Rachel and Thrive Yoga and Wellness here:  https://www.thriveyogaoc.com/       #smallbusinesss #yoga #hiscoxbusiness   At Hiscox, we believe in supporting entrepreneurs who bring bold ideas and strong communities to life. Explore resources and coverage options to help protect and grow your business at Hiscox.com.

    29 min

  4. JAN 21

    Jodi Peterman builds a client-focused interior design practice

    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.

    29 min

  5. JAN 14

    Lesle Lane expands a family enterprise

    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.

    33 min

  6. JAN 7

    Miriam Schulman built a life around her creative work

    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

    32 min

  7. 12/31/2025

    RERUN: Bartender Launches Restaurant Empire: Brian Parenteau's Story

    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

    31 min

  8. 12/24/2025

    RERUN: How to leverage AI for your small business

    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.

    24 min
See All (100)

4.8
out of 5
155 Ratings

About

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.

Information

  • Creator
    Hiscox
  • Years Active
    2019 - 2026
  • Episodes
    100
  • Rating
    Clean
  • Copyright
    © Copyright 2022 All rights reserved.
  • Show Website
    Side Hustle to Small Business

You Might Also Like