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PODCAST

Side Hustle to Small Business

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.

business entrepreneurship

All Episodes

32:45

Smarter training for small businesses with Dr. Carrie...

Side Hustle to Small Business ·

2025/06/11

With a background in college athletics and academia, Dr. Carrie Graham pivoted her career after earning her Ph.D. in Adult Education. As a professional, she had attended many training programs, and realized that these programs were lacking any sort of personalization to the attendees. It was then that she became an Adult Learning Strategist and Consultant, who specializes in helping small businesses creating more engaging and tailor-made training programs. -Chapters- 00:00 Introduction 4:50

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31:51

Organizing a life you love with D’Nai Walker

Side Hustle to Small Business ·

2025/06/04

D’Nai Walker is not a naturally organized person. It wasn’t until she discovered professional organizer Marie Kondo that she got into the practice. When she was laid off, she started doing it on the side, until she was encouraged to go all in. She founded D'Clutter by D'Nai, an organizing company that specializes in senior downsizing, home organization, and productivity solutions.-Chapters- 00:00 Intro 5:52 Overcoming nerves 7:49 Determining your path 8:31 Finding your first clients 10:04

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33:05

Tape it until you make it: Solving a sticky problem

Side Hustle to Small Business ·

2025/05/28

Doug Bard and his father, Bob, have been inventing for most of their lives. However, their greatest idea yet is that of tape. Specifically, moving tape where you can always find the end of the roll. It’s called Wave Tape. Now, as they reimagine a simple solution to a universal issue, the duo is continuing to find success in the market.-Chapters- 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

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31:54

Turning your creative outlet into profit

Side Hustle to Small Business ·

2025/05/21

Jordan Lawson has always loved drawing, coloring, and creating art as a whole. When he was in college, he was inspired by an art entrepreneurship class to start his own business. However, when he graduated, he started working for the government instead. After nine years there, he was ready to make the leap. Jordan founded Ground Zero Studios, a branding studio that helps organizations stand out from their competition.-Chapters- 00:00 Intro 7:26 Overcoming nerves 11:36 Making the leap into

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37:41

How Ethan Bull redefined the Executive Assistant world

Side Hustle to Small Business ·

2025/05/14

After spending many years as an Executive Assistant, Ethan Bull unexpectedly faced layoffs, forcing him to reconsider his career path. With his severance package as a financial cushion, Ethan and his wife, Stephanie, launched ProAssisting, a fractional EA company. Their business focuses on connecting highly skilled EAs with top-level executives, offering flexible, high-quality support without the need for a full-time hire.-Chapters- 00:00 Intro 4:32 Entrepreneurial background 6:35 Starting

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30:17

How to hit a hole-in-one with your side hustle

Side Hustle to Small Business ·

2025/05/07

While browsing the Golf subreddit, David Paxton saw a lot of people posting deals on golf gear. Looking through these deals was fun, but it was also time-consuming if you were looking for a specific item. So Paxton created Daily Golf Steals, automating the deals to help golfers find what they wanted faster. He still runs the business as a side hustle while working a full-time job.-Chapters- 00:00 Intro 2:52 - Entrepreneurial background 4:53 Building DailyGolfSteals 9:14 Overcoming nerves 10:27

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33:06

Failing up: From frustration to success

Side Hustle to Small Business ·

2025/04/30

Kris Louis entered the world of audio/visual by chance while job hunting during the 2008 recession. After several years in the industry, his frustration with the way his employer operated pushed him to take the leap of quitting to start his own successful AV company. Kris credits failure for shaping his journey, teaching him to stay open to multiple paths rather than limiting himself to a single direction.-Chapters- 00:00 intro 3:26 Entrepreneurial background 5:57 Starting the business 9:20

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30:55

Learn how to scale your small business

Side Hustle to Small Business ·

2025/04/23

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

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30:09

Mastering productivity for your small business

Side Hustle to Small Business ·

2025/04/16

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

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33:58

How past injuries inspired Bobby Aldridge’s business...

Side Hustle to Small Business ·

2025/04/09

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

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30:38

Maintaining effective leadership during challenging...

Side Hustle to Small Business ·

2025/04/02

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 -

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36:04

How to use sketching to make your meetings more...

Side Hustle to Small Business ·

2025/03/26

00:00 - Intro7:38 - 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

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34:09

Mastering nonprofit fundraising with Grace Nelson

Side Hustle to Small Business ·

2025/03/19

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

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23:13

How to leverage AI for your small business

Side Hustle to Small Business ·

2025/03/12

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 -

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29:06

Candess Correll's pandemic pivot from NFL Cheerleader...

Side Hustle to Small Business ·

2025/03/05

Candess Correll started her career as a Software Engineer by day, and NFL cheerleader by night. However, when the COVID-19 pandemic hit, Candess found she was ready to retire from cheerleading. Around the same time, inspired by the reality television series “Selling Sunset”, she decided to make the leap into entrepreneurship by launching her real estate career. Now, Candess is a successful realtor with over $6 million in sales and mentors other young realtors.- Chapters - 00:00:00 Introduction

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31:23

Ready to accelerate your business growth? Learn how...

Side Hustle to Small Business ·

2025/02/26

Diane Helbig, the Founder of Helbig Enterprises and host of the Accelerate Your Business Growth podcast, specializes in helping small business owners achieve success. As an expert in business growth, Diane helps businesses that struggle with sales, accountability, systems and productivity. Tune is as she joins Sanjay to explore common business mistakes, how to decide whether to expand your business, hiring the right help, and more.- Chapters - 00:00:00 Introduction and Background 00:03:55

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31:31

Building community and connection for seniors through...

Side Hustle to Small Business ·

2025/02/19

In 2007, Sarah Martin McConnell founded Music for Seniors, a Nashville-based nonprofit, inspired by her mother’s diagnosis with Alzheimer’s disease. Recognizing that older adults often experience greater isolation than other groups, Sarah, a musician herself, saw an opportunity to make a difference. The organization offers live, interactive music programs designed to engage, entertain, and educate seniors, fostering health and well-being.- Chapters - 00:00:00 Introduction and

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23:47

Navigating work-life balance: Advice for...

Side Hustle to Small Business ·

2025/02/12

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

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28:32

The importance of failure within business with Kevin...

Side Hustle to Small Business ·

2025/02/05

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

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31:38

How Josh Russell built success on his own terms

Side Hustle to Small Business ·

2025/01/29

Josh Russell is a musician-turned-photographer. After touring for ten years in the country rap space, building his skills as a musician, as well as photographer and videographer, Josh decided to go all in on photography. Now he owns Josh Russell Photography, a photography company based in Green Bay, Wisconsin. Plus, through his coaching business, Josh teaches other photographers on how to overcome Imposter Syndrome and build their businesses.- Chapters - 00:00:00 Introduction and

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185 results

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