
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

Aug 27, 2025
Aug 27, 2025
32 min
00:00 Introduction and Background
8:22 Overcoming nerves
11:25 Building the business
14:52 Using AI
19:23 Balancing life and work
26:26 Advice for other entrepreneurs
30:23 Closing and contact

Aug 20, 2025
Aug 20, 2025
29 min
00:00 Introduction and background
6:46 Choosing your inventory
10:38 Social media strategy
15:50 Balancing life and work
20:24 Growing the business
22:53 Reflecting on the business
25:19 Advice for other entrepreneurs
27:42 Closing and contact

Aug 13, 2025
Aug 13, 2025
34 min
00:00 Introduction and background
7:00 Challenges when starting the business
14:13 Creating the clothing
20:30 Fulfilling orders
23:18 Building a mission-driven brand
25:31 Balancing family and work
30:16 Reflecting on the business
31:34 Advice for other entrepreneurs
33:11 Closing and contact

Aug 6, 2025
Aug 6, 2025
36 min
Chapters
00:00 Introduction and background
8:10 Getting the first sales
9:31 Getting the product into stores
11:56 Overcoming nerves
14:48 Shark Tank
24:09 Game development
26:40 Balancing work and life
28:50 Running the business in NYC
31:43 Reflecting back on the business
34:07 Advice for other entrepreneurs
35:28 Closing and contact

Jul 30, 2025
Jul 30, 2025
35 min
00:00 Introduction and background
6:29 Overcoming nerves
8:12 Pricing your work
10:22 Training as a woodworker
16:30 Viewing the business longterm
20:56 Balancing work and life
25:31 Finding a coach
31:50 Reflecting on the business
33:18 Advice for other entrepreneurs
34:37 Closing and contact

Jul 23, 2025
Jul 23, 2025
36 min
00:00 Introduction and background
4:45 Starting Global
12:05 Overcoming nerves
13:05 Funding the business
16:23 Making mistakes
20:55 Entering the food space
23:41 Plans to grow the business
27:02 Mission-oriented brands
29:02 Work-life balance
32:25 Reflecting on the business
34:47 Closing and contact

Jul 16, 2025
Jul 16, 2025
35 min
Jo Skillman is a Houston-based Creative Director and the Founder of Jo Skillman LLC. Known for her thoughtful, cause-driven work, she’s partnered with clients like the City of Houston. With expertise in both design and copywriting, Jo brings a well-rounded, strategic approach to every project.
-Chapters-
00:00 Introduction and background
6:35 Overcoming nerves
13:20 Working across multiple industries
18:21 Balancing two sides of the business
21:44 Using AI in your work
25:58 Balancing work and life
29:20 Reflecting back on the business
31:18 Advice for other entrepreneurs
33:20 Closing and contact

Jul 9, 2025
Jul 9, 2025
32 min
00:00 Introduction and background
5:54 Building the business
11:48 Overcoming nerves
13:31 Choosing the right clients
20:25 Financial mistakes as Founders
22:26 Work-life balance
25:37 Reflecting on the business
28:20 Advice for other entrepreneurs
30:55 Closing and contact

Jul 2, 2025
Jul 2, 2025
27 min
00:00 Introduction and Background
9:43 Overcoming nerves
11:17 Designing the right product
14:19 Naming the company
16:01 Brand evolution
18:24 Running the business
21:09 Setting boundaries
23:36 Reflecting on the business
26:05 Advice for other entrepreneurs
26:43 Closing and contact

Jun 25, 2025
Jun 25, 2025
33 min
00:00 Introduction and background
5:31 Entrepreneurial background
7:03 Overcoming nerves
10:12 Going from side hustle to small business
20:06 Mistakes in crowdfunding
23:34 Setting boundaries
25:55 Reflecting back on the business
31:05 Advice for other entrepreneurs
32:03 Closing and contact
