
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 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

Wednesday Jan 22, 2025
Empowering educators from beyond the classroom
Wednesday Jan 22, 2025
Wednesday Jan 22, 2025
00:00:00 Introduction and Background
00:02:23 Long Lines of Educators
00:04:30 Impact of Great Teachers
00:06:20 Professional Learning Communities
00:08:49 Budgeting in Your Side Hustle
00:12:34 Side Hustle to Full-Time Hustle
00:15:18 Data Tools for SEO
00:18:15 Learning other Languages
00:22:07 Bumping Elbows with Elites
00:27:03 Balancing Business at Home
00:28:59 Outsourcing for Optimization
00:32:24 Closing

Wednesday Jan 15, 2025
Entrepreneurs Roundtable: Marketing for Small Businesses
Wednesday Jan 15, 2025
Wednesday Jan 15, 2025
00:00:00 Introduction and Background
00:07:44 The Attention Economy
00:09:02 Unify Your Marketing Voice
00:13:44 Balance Between Branding and Performance
00:20:08 Competitive Audits and Analysis
00:25:39 The Affect of Influencer Marketing
00:34:28 Enhancing Customer Experience
00:36:07 Marketing Mistakes
00:39:39 QA & QC for Marketing Process
00:42:46 Emerging Strategies
00:45:38 Closing

Wednesday Jan 08, 2025
From bartender to multi-million dollar restaurateur
Wednesday Jan 08, 2025
Wednesday Jan 08, 2025
00:00:00 Introduction and Background
00:05:13 Humbling Roots
00:07:55 Buying VS Starting Businesses
00:10:04 First Year Losses
00:12:42 Pandemic Pivots
00:16:14 Elevated And Edgier Concepts
00:18:36 Bartender to Entrepreneur
00:23:34 Sam Malone at Cheers
00:26:42 Living Humble
00:29:07 The Best Apps
00:30:29 Closing

Wednesday Jan 01, 2025
RERUN - How D.R. Fay found entrepreneurial success later in life
Wednesday Jan 01, 2025
Wednesday Jan 01, 2025
D.R. Fay is the Founder of Mouthy Broad Media, a podcast production company that specializes in editing, graphic design and strategy. Beginning her career as a musician, D.R. travelled Asia for close to a decade before coming home to the States and transitioning into corporate roles. When she was 62, while those around her were retiring, D.R. ventured into entrepreneurship and hasn’t looked back.
00:00 - Introduction
06:59 - First entrepreneurial venture later in life
09:37 - Overcoming nerves
11:29 - Managing stress & health problems
21:00 - Advice for other entrepreneurs
23:21 - Closing and contact

Wednesday Dec 25, 2024
RERUN - How to turn past experiences into entrepreneurial success
Wednesday Dec 25, 2024
Wednesday Dec 25, 2024
Matt Gluckman has worn many hats. From working at a produce stand to running a real estate company, Matt has always had an entrepreneurial spirit. Now, Matt owns Think Fitness Life, a remote personal training company, with his business partner Eric. From his past job experiences, Matt has mastered the skills of communication and thrives on helping individuals become their best selves through personal training.
- Chapters -
00:00 - Introduction
04:49 - Matt's work history and transferable skills
11:14 - Overcoming nerves
12:47 - Having a business partner in a different state
15:32 - Balancing stress
17:33 - Setting boundaries
22:37 - What Matt would have done differently
26:02 - Advice to other entrepreneurs
26:35 - Closing and contact information

Wednesday Dec 18, 2024
How writing recharged Aaron Ryan’s creative spirit
Wednesday Dec 18, 2024
Wednesday Dec 18, 2024
00:00:00 Introduction and Background
00:03:35 What’s A Kool Aid Stand?
00:05:57 The 80’s Comic Books
00:11:29 Writing A Book Every Sixty Days
00:15:24 Dissonance: The Lack Of Harmony
00:17:19 Do You Believe?
00:21:48 Pear-Shaped Men
00:25:36 Entrepreneurial Blurred Lines
00:27:02 Listening To The Voice Within
00:30:15 Endorsement Does Not Equal Trajectory
00:33:10 Closing Remarks

Wednesday Dec 11, 2024
Growing a partnership in life and entrepreneurship
Wednesday Dec 11, 2024
Wednesday Dec 11, 2024
00:00:00 Introduction and Background
00:02:24 Side Hustle, Small Business, Marriage
00:05:41 Peddling Up The Ladder
00:09:57 Excitement Outweighing Risk
00:10:50 Burning Out And Growing Up
00:14:38 NFTs Are A NO
00:16:51 Shifting The Infield
00:20:43 Failure Will Fix It
00:24:39 Fundraising Frenzy
00:30:52 Opportunity In AI
00:34:08 Closing