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

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

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

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

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

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