Side Hustle to Small Business

By HiscoxBusiness Entrepreneurship Careers

Side Hustle to Small Business episodes

April 08Joshua Lipkin on transitioning from freelance to founder
With a background in media production, Joshua Lipkin, like many people in the media space, found himself freelancing. When he landed a large contract, he decided it was time to found GreyLee Creative, a full-service production and post-production company that focuses on crafting high-quality visual content that captivates and engages audiences. Sanjay and Joshua discuss Joshua’s transition from freelancer to business owner, finding your niche in the business, and starting Atlanta’s Editor Collective, a community of over 800 editors.

Takeaways:
When to transition from freelance to business owner
Why you should build a networking community
Determining what to focus on when growing your business
The importance of relationships in growing your business

Chapters
00:00 Introduction and background
5:50 Shifting from freelancer to founder
11:08 Starting Atlanta Editors Collective
18:35 Advice for other entrepreneurs
21:15 Closing and contact

Find out more about Joshua and GreyLee Creative at https://www.greyleecreative.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.

#mediaproduction #creativeservices #freelancing
24 min
April 01Gary Mendelson’s shift from Broadway to healthcare
Gary Mendelson is currently on his seventh career. After working on Broadway, Gary transitioned to retail ownership, before becoming a Massage Therapist and the Founder of The Massage Garage, a full-service massage practice focused on delivering results-driven massages to get you moving again. Sanjay and Gary discuss Gary’s theatre background the inspiration for his career, how lessons he learned in the retail space translate into healthcare, and how addiction has molded him into a better person and business owner.

Takeaways:
How various backgrounds can inform your current work
The importance of wellness in entrepreneurship
The importance of education in pain management
How a passion for helping others drives work and personal fulfillment

Chapters
00:00 Introduction
9:16 Moving states
12:25 Transferable skills in business
15:49 Advice for other entrepreneurs
17:21 Closing and contact

Learn more about Gary and The Massage Garage at https://themassagegarage.net/

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.

#massagetherapy #entrepreneurship #healthcare
19 min
March 25Turning fun into profit: Paul Baillie on Shift Arcade’s growth
What does it really take to build a profitable arcade business from scratch and scale it into a franchise? In this episode of Side Hustle to Small Business, Sanjay sits down with Paul Baillie, Co-Founder of Shift Arcade, to unpack the journey of building a modern arcade brand through bootstrapping, smart growth, and strategic franchising.

Paul shares how Shift Arcade went from a simple idea into a thriving entertainment business, the realities of funding a startup without outside investors, and the lessons learned while preparing to franchise. This conversation is packed with practical insights for entrepreneurs looking to turn passion-driven ideas into scalable businesses.

Topics include:
Building an arcade business from the ground up
Bootstrapping versus raising capital
Creating memorable customer experiences
Preparing your business model for franchising

Chapters
00:00 Introduction
2:45 Building Shift Arcade
9:41 Overcoming nerves
12:18 Expanding the business
19:19 Advice for other entrepreneurs
21:02 Closing and contact

Learn more about Shift Arcade at https://shiftarcade.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.

#franchising #bootstrapping #startupjourney
23 min
March 04 Creating sensory-safe spaces with Stephanie Lee Jackson
In this episode of Side Hustle to Small Business, Sanjay speaks with Stephanie Lee Jackson, founder of Practical Sanctuary, about how sensory-aware interior design can transform daily life, especially for neurodivergent individuals. Stephanie shares her journey through multiple career shifts and why creating calm, supportive spaces is essential for mental health, productivity, and well-being.

What you’ll learn:
• What sensory interior design is and who it’s for
• Practical ways to reduce sensory overwhelm at home and work
• Why boundaries are essential for entrepreneurs and creatives
• How to navigate multiple career shifts while building a business

Chapters
00:00 Introduction and background
15:35 Balancing multiple businesses
18:30 Writing a book
27:30 Reflecting on the business
29:27 Closing and contact

Learn more about Stephanie and Practical Sanctuary at practicalsanctuary.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.

#interiordesign #entrepreneurship #sensorydesign
31 min
February 25Mic Foster launches No Gifts Please to solve toy clutter
Mic Foster is the founder of No Gifts Please, an online registry platform focused on creating meaningful experiences for children, over gift-giving. Mic shares how watching unused toys pile up after his daughters’ birthdays sparked the idea for a platform that helps families rethink gifting, reduce waste, and create more meaningful celebrations.

Mic and Sanjay dive into Mic’s background as a serial entrepreneur, the lessons learned from multiple startups, and the moment he realized the world didn’t need more toys, it needed a better way to give. They also unpack how No Gifts Please survived explosive early growth, the operational challenges that came with scaling fast, and how Mic stayed grounded during intense periods of pressure and uncertainty.

What You’ll Learn:
How serial entrepreneurship shaped Mic’s approach to building No Gifts Please
Why solving a personal pain point can unlock powerful business ideas
The realities of extreme startup growth and how to survive it
Lessons in leadership, resilience, and long-term vision

Chapters
00:00 Introduction and background
8:18 Overcoming nerves
14:38 Starting No Gifts Please
23:46 Work-life balance
25:51 Technology and Apps
31:10 Advice for other entrepreneurs
32:08 Closing and contact

Learn more about Mic and No Gifts Please at https://nogiftsplease.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.

#startupgrowth #founderstory #smallbusiness
34 min
February 18 Chris Brady on turning a single location into a franchise
What does it really take to turn a food truck into a franchise? In this episode of Side Hustle to Small Business, Chris Brady, co-founder of Timber Pizza, shares how he and his partner grew their business from making pizza out of a 1967 Chevy to operating a restaurant brand with multiple franchised locations across the United States.

Chris walks through the early scrappy days of the business, the moment they realized Timber Pizza could scale, and the practical realities of building a franchise system from scratch. This conversation goes deep on what founders often underestimate about franchising, how to protect brand quality as you grow, and what needs to be in place before expanding beyond a single location.

What you’ll learn:
• How Timber Pizza evolved from a mobile operation to a franchise model
• The systems and processes needed before franchising
• Common mistakes founders make when scaling too quickly
• How to maintain brand consistency across multiple locations
• What Chris would do differently if he were starting again

Chapters
00:00 Introduction and Background
9:32 Franchising the business
28:13 Health and Wellness
29:17 Advice for other entrepreneurs
31:46 Closing and contact

Learn more about Timber Pizza at timberpizza.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.

#smallbusiness #franchising #foodbusiness
34 min
February 11 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
33 min
February 04 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.
34 min
January 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.
30 min
January 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.
30 min

About Side Hustle to Small Business

From the publisher's feed

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.…