Hiscox

Side Hustle to Small Business

Business EN ↓ 100 episodes

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.

Author

Hiscox

Category

Business

Podcast website

www.hiscox.com

Latest episode

Apr 8, 2026

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Episodes

How past injuries inspired Bobby Aldridge’s business journey 09.04.2025

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 m...

Maintaining effective leadership during challenging times 02.04.2025

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...

How to use sketching to make your meetings more effective 26.03.2025

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 differe...

Mastering nonprofit fundraising with Grace Nelson 19.03.2025

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...

How to leverage AI for your small business 12.03.2025

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...

Candess Correll's pandemic pivot from NFL Cheerleader to Realtor 05.03.2025

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...

Ready to accelerate your business growth? Learn how from expert Diane Helbig 26.02.2025

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 busines...

Building community and connection for seniors through music 19.02.2025

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...

Navigating work-life balance: Advice for entrepreneurs and beyond 12.02.2025

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...

The importance of failure within business with Kevin Sandlin 05.02.2025

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,...

How Josh Russell built success on his own terms 29.01.2025

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...

Empowering educators from beyond the classroom 22.01.2025

Ashley Mikkelsen is passionate about teaching Spanish. However, when she had her first child, she realized that it was difficult to balance teaching and motherhood. It was at this point that she transitioned her side hustle of creating educational resources for other Spanish teachers to her full-time job. Srta Spanish looks to provide Spanish teachers with resources to amplify their classes throug...

Entrepreneurs Roundtable: Marketing for Small Businesses 15.01.2025

This episode kicks off a three-part series where we take a deep dive into a topic alongside seasoned professionals. In this episode, we’re focusing on marketing strategies for small businesses. We are joined by Jon Katinsky, the President of Hothouse, a branding and design house, as well as Javier Santana, the Chief Experience Officer of Chemistry Agency. We discuss social media marketing, influen...

From bartender to multi-million dollar restaurateur 08.01.2025

Brian Parenteau never wanted to work weekends. However, when he found himself bartending at a local restaurant, he quickly fell in love with the industry. As he rose the ranks within the restaurant space and found himself helping organizations open new restaurants, he realized he could do it on his own. Fast-forward to today, Brian is the owner of four restaurants and bars in Florida, with hopes o...

RERUN - How D.R. Fay found entrepreneurial success later in life 01.01.2025

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....

RERUN - How to turn past experiences into entrepreneurial success 25.12.2024

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 perso...

How writing recharged Aaron Ryan’s creative spirit 18.12.2024

Aaron Ryan loves all things creative, but has found that writing has been his number one source of inspiration and drive. He is the author of The Dissonance series, a science fiction series based on the idea of aliens visiting earth. Since having started writing a year ago, Aaron has already penned six books in the series. Writing has not only become his creative passion but also the driving force...

Growing a partnership in life and entrepreneurship 11.12.2024

Kate Wallace and Blake Chasen first met while working at the same startup. Through their work together, not only did they come to realize that they have great synergy in the office, but also personally as well. With a background in writing, Blake found his niche in custom storytelling online during the pandemic. Now, the couple owns Avenue Stories, an AI-powered storytelling app for children that...

How Winnifred Tataw went from author to publisher 04.12.2024

Winnifred Tataw has been writing for as long as she can remember, and has been a professional author for eight years. During the pandemic, Winnifred was looking for ways to better support the indie publishing industry. It was then that she decided to launch Win’s Books Publishing, which officially opened in April of 2024. Now, Winnifred and her team support a handful of authors through their publi...

How a Christmas gift turned into a six-figure business 27.11.2024

Dawn Kennedy is an attorney, author, and podcaster. In 2020, her husband Mike received a roaster and some coffee beans for Christmas. After tasting his coffee, Dawn bet him he could sell it online. Not expecting much, they made a Facebook post and ended up selling eleven bags. From there, Convoy Road Coffee Roasters was born. Fast-forward to this year, Dawn and Mike have five employees and bring i...

Building a supportive community to benefit your children 20.11.2024

When Michelle Choairy’s son was diagnosed with a rare genetic disorder, she found that there were not enough resources out there for parents going through the same thing as her. This is when she founded Wisdom4ComplexKids, an organization focused on providing resources and building community with parents of children with similar needs. Now, Michelle’s goal is to create the best life for her family...

How Stephanie Shanks increased her revenue by tenfold 13.11.2024

Stephanie Shanks has always had an entrepreneurial spirit, from selling livestock in her youth to owning a message therapy practice. It wasn’t until her first child was born that she discovered her passion for photography. With the encouragement of her community, she founded Staphanie Shanks Photography in 2011. When she realized she wasn’t charging enough, she changed her rates and increased her...

Creating a global community through podcasting 06.11.2024

Jeff Revilla started his entrepreneurial journey in the early 2000’s by opening a mail order skateboard shop. After that business went under during the 2008 financial crisis, Jeff’s entrepreneurial spirit never went away. In June of 2024, he opened Poduty Live, a podcasting and live event theater based in Tarentum, Pennsylvania. This space allows Jeff to connect podcasters and local and virtual ta...

Amity Gleason’s journey from Attorney to Jewelry Maker 30.10.2024

Formally a courtroom attorney, Amity Gleason first gained an interest in jewelry design when she was getting married. As someone with an appreciation of gothic style, she found most jewelry on the market didn’t match this style and instead followed the same cookie cutter patterns. This inspired her to start Amity Alexandra Jewelry Design, a jewelry company focused on making one-of-a-kind pieces th...

How Bonnie Conrad went from furniture builder to marketer 23.10.2024

As a military spouse, Bonnie Conrad was tired of starting at a new job everywhere she moved. In 2018, she decided to take the leap into entrepreneurship by founding I Built This, a furniture building company. Through selling furniture, she discovered digital marketing and decided to dive into it full-time by founding Second You. In 2023, she merged her business with Inn8ly, a website technology co...

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