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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 ownerWhy you should build a networking communityDetermining what to focus on when growing your businessThe 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 -
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 workThe importance of wellness in entrepreneurshipThe importance of education in pain managementHow 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 -
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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 upBootstrapping versus raising capitalCreating memorable customer experiencesPreparing 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 -
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 -
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 PleaseWhy solving a personal pain point can unlock powerful business ideasThe realities of extreme startup growth and how to survive itLessons 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 -
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 -
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 -
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. -
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. -
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
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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 businessHaving a safety netPrioritizing family while growing a businessChapters
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.
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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.
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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.
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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.
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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
- Visa fler
