
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

18 hours ago
Learn how to scale your small business
18 hours ago
18 hours ago
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.
-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

Wednesday Apr 02, 2025
Maintaining effective leadership during challenging times
Wednesday Apr 02, 2025
Wednesday Apr 02, 2025
As an experienced marketer, Amy Moudy Comeau has seen her fair share of marketing emergencies. However, when the COVID-19 pandemic hit while Amy was working in health care marketing, it seemed like every day brought a new crisis. It was at this time that Amy started sending out weekly inspirational emails to her team, which lead to her writing the book Every Storm Runs Out of Rain, which offers a peek behind the curtain of these challenging times.
Chapters
00:00 - Intro and background
7:23 - Making the leap into entrepreneurship
16:08 - Building a personal brand
19:42 - Avoiding a personal crisis when leaving your company
21:31 - Overcoming nerves
23:15 - Dealing with self-doubt
26:07 - Advice for leading through a crisis
29:14 - Closing and contact

Wednesday Mar 26, 2025
How to use sketching to make your meetings more effective
Wednesday Mar 26, 2025
Wednesday Mar 26, 2025
00:00 - Intro
7:38 - Entrepreneurial History
8:51 - Transition into a full-time business
10:56 - Finding your first customers
12:40 - Overcoming nerves
14:54 - Hiring staff members
18:47 - Balancing speed and creativity
21:23 - Implementing sketching into your business
23:24 - William’s favorite stories
26:12 - Work-life balance
28:10 - Technology recommendations
30:12 - What would you do differently?
31:54 - Advice for other entrepreneurs
33:44 - Closing and contact

Wednesday Mar 19, 2025
Mastering nonprofit fundraising with Grace Nelson
Wednesday Mar 19, 2025
Wednesday Mar 19, 2025
With a background in the nonprofit and fundraising space, Grace Nelson was pursuing her MBA when she started taking on consulting jobs on the side. After graduating, what started as a few side projects quickly grew into a full-fledged business. Now she is the CEO of Magenta Strategy, a consulting firm that specializes in helping nonprofits develop strategic, sustainable fundraising solutions that drive long-term impact.
00:00 intro
3:09 - entrepreneurial background
11:09 - Navigating the nonprofit world
13:35 - Challenge Forecast
17:25 - Nonprofits vs. For profit’
22:20 - Reflecting on entrepreneurial journey
24:38 - Growing as a leader
26:20 - Establishing boundaries
28:30 - What is one thing you would do differently?
30:20 - Advice for other entrepreneurs
32:34 - Closing and contact

Wednesday Mar 12, 2025
How to leverage AI for your small business
Wednesday Mar 12, 2025
Wednesday Mar 12, 2025
Joselyne Walter has seen her fair share of corporate jobs. In these environments, even with large budgets, she found that there was a gap in resources. It was then that she got the idea for The Digg Agency, a marketing agency that helps organizations execute high scale projects. By leveraging AI, Joselyne efficiently scaled her business during its early stages, paving the way for long-term success.
Chapters
00:00 - Intro
4:44 - Starting the Digg Agency
9:03 - Managing work-life balance
10:12 - Maintaining exercise practices
12:17 - The impact of AI
13:52 - Challenges of incorporating AI
14:58 - Upcoming trends and tools in AI
16:10 - Impact of AI on teams
17:18 - Reflecting on past mistakes
18:18 - Advice from Jocelyn
20:45 - Encouraging words
21:53 - Closing and Contact

Wednesday Mar 05, 2025
Candess Correll's pandemic pivot from NFL Cheerleader to Realtor
Wednesday Mar 05, 2025
Wednesday Mar 05, 2025
00:00:00 Introduction and Background
00:02:55 Computer Science to Cheer Captain
00:06:25 Transparency for Flexibility
00:08:53 Selling Sunset
00:11:03 Confidence in Corporate
00:14:44 Security in the Unknown
00:18:08 Building Hustle with Brand
00:19:56 Empowering Young Women
00:21:52 Opportunities Worth Chasing
00:24:34 Managing Expectations
00:26:58 Define Your WHY
00:28:38 Closing

Wednesday Feb 26, 2025
Ready to accelerate your business growth? Learn how from expert Diane Helbig
Wednesday Feb 26, 2025
Wednesday Feb 26, 2025
00:00:00 Introduction and Background
00:03:55 Facing a Startup Head on
00:06:07 Systems and Structure for Growth
00:12:24 Common Revenue Mistakes
00:15:06 How to Let Go of the Reigns
00:17:14 Market Expansion 101
00:21:10 Slow-Walk Responsibilities
00:26:26 Be Particular with Partnerships
00:30:55 Closing

Wednesday Feb 19, 2025
Building community and connection for seniors through music
Wednesday Feb 19, 2025
Wednesday Feb 19, 2025
00:00:00 Introduction and Background
00:03:09 Writing with Walter Hyatt
00:06:22 Caroling for Profit
00:08:17 Tumbling Staircases
00:14:28 Charge for Your Creativity
00:18:13 Follow Your Bliss
00:21:24 Support of Music City
00:25:27 COVID Courtyard Concerts
00:28:45 Finding the Experts
00:31:00 Closing