
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

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

Wednesday Feb 12, 2025
Navigating work-life balance: Advice for entrepreneurs and beyond
Wednesday Feb 12, 2025
Wednesday Feb 12, 2025
Today we are joined by two entrepreneurs to discuss work-life balance. Dr. Alice Rizzi is a Psychologist based in New York City, specializing in helping individuals overcome fear and self-doubt, manage their stress, and gain confidence. Adam Walker is a long-time entrepreneur, having founded multiple companies over his career. Join us as we discuss determining your values, setting boundaries, and useful tips on achieving work-life balance.
- Chapters -
00:00:00 Introduction and Background
00:04:58 Defining Work-Life Balance
00:06:33 Personal Values Impact Life
00:08:38 Getting Out of Sync
00:09:41 Physical Health Issues
00:12:52 Does Tech Affect Work-Life?
00:15:03 Finding Balance in Busy-ness
00:17:22 Tools for Task Management
00:19:55 Less Work = Higher Quality
00:20:38 Reflect for Successful Balance
00:21:36 Closing

Wednesday Feb 05, 2025
The importance of failure within business with Kevin Sandlin
Wednesday Feb 05, 2025
Wednesday Feb 05, 2025
Kevin Sandlin is a Serial Entrepreneur based in Atlanta, Georgia. Over the course of his career, he has started eleven businesses, and as a result, is no stranger to failure. Currently, Kevin is the Chief Operating Officer of Transcend LV, a low-voltage wiring and cabling business. In today’s episode Sanjay and Kevin take a deep dive into what failure means for an entrepreneur, how to overcome it, and mistakes to avoid going forward.
Chapters
00:00 - Introduction and Entrepreneurial Background
3:33 - History of Failure
10:14 - Changing outlook on failure
13:15 - An investor's role in overcoming failure
18:00 - Support for entrepreneurs around failure
22:36 - Managing risk
27:03 - Closing and contact

Wednesday Jan 29, 2025
How Josh Russell built success on his own terms
Wednesday Jan 29, 2025
Wednesday Jan 29, 2025
- Chapters -
00:00:00 Introduction and Background
00:04:33 The Hustler Mentality
00:06:28 Genres of Entrepreneurship
00:07:56 Shedding a Business
00:11:07 Get Rid of Imposter Syndrome
00:13:34 “If You’re Not Terrified, You’re Not Charging”
00:17:04 Entrepreneurialism and ADHD
00:22:14 Comfort in the Uncomfortable
00:24:33 Extensions of AI
00:26:45 Side Hustling with an iPhone
00:27:51 Focus = Fast Growth
00:31:08 Closing