
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

Jun 18, 2025
Jun 18, 2025
36 min
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

Jun 11, 2025
Jun 11, 2025
32 min
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

Jun 4, 2025
Jun 4, 2025
31 min
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

May 28, 2025
May 28, 2025
33 min
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

May 21, 2025
May 21, 2025
31 min
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

May 14, 2025
May 14, 2025
37 min
-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

May 7, 2025
May 7, 2025
30 min
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

Apr 30, 2025
Apr 30, 2025
33 min
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

Apr 23, 2025
Apr 23, 2025
30 min
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

Apr 16, 2025
Apr 16, 2025
30 min
-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
