Side Hustle to Small Business

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 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

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

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