Side Hustle to Small Business

Latest Episodes:

Inside the proposal planning business Nov 05, 2025

Show notes

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

Managing growth across multiple companies Oct 29, 2025

Show notes

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

Sleeping on success: How affiliate links built a business Oct 22, 2025

Show notes

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

Building and scaling an app: Advice from the WineLikes founder Oct 15, 2025

Show notes

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

Marketing made simple for contractors and landscapers Oct 08, 2025

Show notes

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

From pitching products to building a personal brand Oct 01, 2025

Show notes

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

How to run payroll like a pro Sep 24, 2025

Show notes

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

How Farmer Nick grew a viral business Sep 17, 2025

Show notes

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

How the right bookkeeper can boost your growth Sep 10, 2025

Show notes

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

Saving the shore, one product at a time Sep 03, 2025

Show notes

Cat Lepetit has always had a deep love for the beach. After spending 20 years in the cosmetics industry, she felt it was time for a new chapter. That’s when the idea for Sun Drunk was born, a beach goods company focused on simplicity, peace of mind, and sustainability. With a mission to help protect our oceans and keep beaches clean, Sun Drunk is all about making it easier to enjoy the coast while caring for it too.

Chapters

00:00 Introduction and background

7:48 Overcoming nerves

11:23 Designing the products

16:23 Building a customer base

19:56 Giving back

22:25 Overcoming stress

25:32 Looking back

28:02 Advice for other entrepreneurs

29:57 Closing and contact