
A weekly podcast from Hiscox, the small business insurance experts. We’re changing the conversation around the side hustle and featuring founders at various stages of their small business journey. These entrepreneurs are pushing the envelope while keeping their values and have learned a few lessons along the way. Listen each week for conversation, context, and camaraderie. Hosted by Sanjay Parekh, produced by Edgewise.Media.
Episodes

5 days ago
5 days ago
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

Wednesday Jun 04, 2025
Organizing a life you love with D’Nai Walker
Wednesday Jun 04, 2025
Wednesday Jun 04, 2025
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

Wednesday May 28, 2025
Tape it until you make it: Solving a sticky problem
Wednesday May 28, 2025
Wednesday May 28, 2025
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

Wednesday May 21, 2025
Turning your creative outlet into profit
Wednesday May 21, 2025
Wednesday May 21, 2025
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

Wednesday May 14, 2025
How Ethan Bull redefined the Executive Assistant world
Wednesday May 14, 2025
Wednesday May 14, 2025
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

Wednesday May 07, 2025
How to hit a hole-in-one with your side hustle
Wednesday May 07, 2025
Wednesday May 07, 2025
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

Wednesday Apr 30, 2025
Failing up: From frustration to success
Wednesday Apr 30, 2025
Wednesday Apr 30, 2025
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

Wednesday Apr 23, 2025
Learn how to scale your small business
Wednesday Apr 23, 2025
Wednesday Apr 23, 2025
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

Wednesday Apr 16, 2025
Mastering productivity for your small business
Wednesday Apr 16, 2025
Wednesday Apr 16, 2025
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

Wednesday Apr 09, 2025
How past injuries inspired Bobby Aldridge’s business journey
Wednesday Apr 09, 2025
Wednesday Apr 09, 2025
Bobby Aldridge, a sports kinesiologist based in California, has been an athlete and has worked with athletes for as long as he can remember. After having two hip replacement surgeries, Bobby was inspired to create his business BAMmetrics Systems, and within that, “The Bobby Aldridge Method”, a method he uses to help athletes alleviate pain, avoid injury, increase mobility, and improve functional movement.
-Chapters-
00:00 - Intro
4:30 - First entrepreneurial experience
9:36 - Starting BAM metrics
12:28 - Managing your time with a side hustle
14:51 - Exercise and wellbeing
16:05 - Details of BAM Metrics
20:34 - Marketing the business
22:45 - Moving the business online
24:35 - Building partnerships in business
25:45 - Overcoming nerves
28:00 - Reflecting on the business
32:38 - Closing and contact