After several years working as a licensed psychotherapist, Arianna Smith launched a copywriting side hustle in 2019. Her goal was to help fellow therapists write copy that feels clear, human, and approachable. By simplifying clinical language and focusing on genuine connection, Arianna has grown that side hustle into a thriving business, one that now surpasses her therapy practice.

-Chapters-

00:00 Introduction and background

6:55 Finding clients

8:45 Growing a side hustle while working full-time

14:46 Why this business is essential

18:01 Balancing a side hustle

21:14 Expanding the business

23:50 Advice for clients

27:15 Structure of the business

30:15 Reflecting on the business

33:47 Advice for other entrepreneurs

35:04 Closing and contact

With a background in college athletics and academia, Dr. Carrie Graham pivoted her career after earning her Ph.D. in Adult Education. As a professional, she had attended many training programs, and realized that these programs were lacking any sort of personalization to the attendees. It was then that she became an Adult Learning Strategist and Consultant, who specializes in helping small businesses creating more engaging and tailor-made training programs. 

-Chapters-

00:00 Introduction

4:50 Starting the business

9:50 Overcoming nerves

11:32 Identifying effective training

16:06 Treating your employees right

19:24 Using training to develop company culture

23:10 Finding your first client

25:14 The future of the business

27:18 Reflecting back on the business

30:24 Advice for other entrepreneurs

31:21 Closing and contact

D’Nai Walker is not a naturally organized person. It wasn’t until she discovered professional organizer Marie Kondo that she got into the practice. When she was laid off, she started doing it on the side, until she was encouraged to go all in. She founded D'Clutter by D'Nai, an organizing company that specializes in senior downsizing, home organization, and productivity solutions.

-Chapters-

00:00 Intro

5:52 Overcoming nerves

7:49 Determining your path

8:31 Finding your first clients

10:04 Navigating client work

13:58 Marketing tools

16:41 Staying organized in your small business

20:52 Setting boundaries

22:53 Health and Wellness

26:08 Technology and apps

27:37 Reflecting on the business

29:21 Advice 

30:25 Closing and contact

Doug Bard and his father, Bob, have been inventing for most of their lives. However, their greatest idea yet is that of tape. Specifically, moving tape where you can always find the end of the roll. It’s called Wave Tape. Now, as they reimagine a simple solution to a universal issue, the duo is continuing to find success in the market.

-Chapters-

00:00 Intro

6:02 - Entrepreneurial background

7:17 The history of Wave Tape

11:25 Sales and distribution

18:14 Overcoming nerves

19:28 Balancing full time work with a side hustle

21:48 Exercise routines

22:53 Helpful technology and apps

23:53 Marketing the product

27:34 Long term vision

29:19 Reflecting back on the business

30:22 Advice for other entrepreneurs

31:18 Closing and contact

Jordan Lawson has always loved drawing, coloring, and creating art as a whole. When he was in college, he was inspired by an art entrepreneurship class to start his own business. However, when he graduated, he started working for the government instead. After nine years there, he was ready to make the leap. Jordan founded Ground Zero Studios, a branding studio that helps organizations stand out from their competition.

-Chapters-

00:00 Intro

7:26 Overcoming nerves

11:36 Making the leap into entrepreneurship

14:16 Building a branding studio

18:37 Getting clients

22:31 Managing stress

25:11 Using AI as an artist

28:39 Reflecting back on the business

30:34 Closing and contact

After spending many years as an Executive Assistant, Ethan Bull unexpectedly faced layoffs, forcing him to reconsider his career path. With his severance package as a financial cushion, Ethan and his wife, Stephanie, launched ProAssisting, a fractional EA company. Their business focuses on connecting highly skilled EAs with top-level executives, offering flexible, high-quality support without the need for a full-time hire.

-Chapters-

00:00 Intro

4:32 Entrepreneurial background

6:35 Starting ProAssisting

14:51 Keeping up with technology

16:16 Using AI in the company

19:44 Delegating tasks to an assistant

22:16 The future of the business

28:17 Work-life balance

31:51 Looking back on the business

34:27 Advice to other entrepreneurs

36:23 Closing and contact

While browsing the Golf subreddit, David Paxton saw a lot of people posting deals on golf gear. Looking through these deals was fun, but it was also time-consuming if you were looking for a specific item. So Paxton created Daily Golf Steals, automating the deals to help golfers find what they wanted faster. He still runs the business as a side hustle while working a full-time job.

-Chapters-

00:00 Intro

2:52 - Entrepreneurial background

4:53 Building DailyGolfSteals 

9:14 Overcoming nerves 

10:27 Keeping costs low 

12:13 Using  automation tools

16:30 Marketing tools

18:17 Managing work-life balance and setting boundaries

24:34 Looking to the future

27:07 Advice for other entrepreneurs 

28:55 Closing and contact 

Kris Louis entered the world of audio/visual by chance while job hunting during the 2008 recession. After several years in the industry, his frustration with the way his employer operated pushed him to take the leap of quitting to start his own successful AV company. Kris credits failure for shaping his journey, teaching him to stay open to multiple paths rather than limiting himself to a single direction.

-Chapters-

00:00 intro

3:26 Entrepreneurial background

5:57 Starting the business

9:20 Failure within the business

11:45 Staying innovative in the AV industry

14:23 Transitioning from employee to business owner

17:09 Revenue

18:31 The impact of COVID-19

20:38 Challenges in the business

22:44 Team culture

27:31 Managing stress

30:05 Reflecting back on the business

31:06 Advice for other entrepreneurs

31:50 Closing and contact

Rachel Donnelly was just starting her career and raising two small children when her parents passed on. As she struggled with settling estates, bank accounts, and other various paperwork, she knew there had to be a better way. It was at this time that Rachel thought of the idea for After Light, an end-of-life and legacy planning service. With six years under her belt, Rachel has now written the book “Late To Your Own Funeral” which is out now.

-Chapters-

00:00 Intro

8:05 Finding the first client

10:13 Transitioning from side hustle to small business

11:42 Overcoming nerves

13:32 Balancing life and work

15:26 AD

15:48 Entrepreneurial past

16:43 The future of the business

20:02 Building potential competitors 

23:48 Advice for other entrepreneurs 

25:53 Reflecting on the business

26:52 Dealing with burnout

27:49 Contact and Rachel’s new book

Monisha Longacre has many titles. She is an author, a fractional COO at two different companies, and the founder of priorigami, a productivity app aimed at helping entrepreneurs be the most productive they can be. As an expert in productivity, Monisha shares her insights on timeblocking, managing multiple roles, and being transparent with your employees. Monisha is the author of "Practical Productivity: A Guide to Surviving Life's Juggling Act" which is out now!

-Chapters-

00:00 Introduction

4:26 Launching a side hustle

6:18 Advice on delegating work

8:10 Balancing multiple part-time jobs and side hustles

9:53 Learning to say no

13:06 Timeblocking

16:30 Looking ahead in the long term

17:26 Comparing small and large organizations

19:39 Overcoming nerves

22:33 Managing time in a day

25:41 Advice to those wanting to start a side hustle

27:32 Reflecting back

28:56 Closing and contact