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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

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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34:59

Empowering educators from beyond the classroom

Side Hustle to Small Business ·

2025/01/22

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 through reading, games, lesson plans, and more.- Chapters - 00:00:00 Introduction and Background 00:02:23

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49:09

Entrepreneurs Roundtable: Marketing for Small Businesses

Side Hustle to Small Business ·

2025/01/15

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, influencer marketing, and emerging marketing trends.- Chapters - 00:00:00 Introduction and

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30:58

From bartender to multi-million dollar restaurateur

Side Hustle to Small Business ·

2025/01/08

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 of expanding into other states.- Chapters- 00:00:00 Introduction and Background 00:05:13 Humbling

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24:50

RERUN - How D.R. Fay found entrepreneurial success...

Side Hustle to Small Business ·

2025/01/01

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.- Chapters - 00:00 - Introduction 06:59 - First entrepreneurial venture later in life 09:37 -

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27:57

RERUN - How to turn past experiences into...

Side Hustle to Small Business ·

2024/12/25

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

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33:39

How writing recharged Aaron Ryan’s creative spirit

Side Hustle to Small Business ·

2024/12/18

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 that propels him forward in his life and career. - Chapters - 00:00:00 Introduction and

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35:19

Growing a partnership in life and entrepreneurship

Side Hustle to Small Business ·

2024/12/11

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 allows you to custom build characters and stories. - Chapters - 00:00:00 Introduction and

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32:33

How Winnifred Tataw went from author to publisher

Side Hustle to Small Business ·

2024/12/04

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 publishing process.

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31:07

How a Christmas gift turned into a six-figure business

Side Hustle to Small Business ·

2024/11/27

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 in six-figures of revenues annually. - Chapters - 00:00:00 Introduction and Background 00:02:23

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30:40

Building a supportive community to benefit your children

Side Hustle to Small Business ·

2024/11/20

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 and other families who have complex children. - Chapters - 00:00:00 Introduction and

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27:30

How Stephanie Shanks increased her revenue by tenfold

Side Hustle to Small Business ·

2024/11/13

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 revenue tenfold. Chapters 00:00 Introduction and background 5:56 Photography background 7:54 Going

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29:39

Creating a global community through podcasting

Side Hustle to Small Business ·

2024/11/06

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 talent to excited audience members.Chapters 00:00 Introduction and background 6:02 Finding the right

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31:46

Amity Gleason’s journey from Attorney to Jewelry Maker

Side Hustle to Small Business ·

2024/10/30

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 that don’t break the bank.Chapters 00:00 - Introduction and background 6:57 - Jewelry making

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28:15

How Bonnie Conrad went from furniture builder to...

Side Hustle to Small Business ·

2024/10/23

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 company, to expand her impact in the digital space.Chapters 00:00 - Introduction and background 8:10

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30:27

How Ryan Klee leads with purpose through thought...

Side Hustle to Small Business ·

2024/10/16

Ryan Klee is the Co-Founder of Rootstock, an organization dedicated to helping ambitious leaders and businesses expand their brands and scale their operations. Rootstock achieves this by harnessing the power of strategic thinking, refining compelling narratives, and sharing those stories with broader audiences. With a background in PR, Ryan grew tired of the traditional 9 to 5 routine and, along with a colleague, launched the business in 2021. Chapters 00:00 - Introduction and background 3:30 -

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33:37

How your perspective on entrepreneurship can evolve...

Side Hustle to Small Business ·

2024/10/09

With a background in marketing, Chris Van Nostrand never envisioned himself becoming an entrepreneur. It wasn't until his late 30s, seeking a change, that he decided to transform his lifelong passion for powerlifting into a full-time career. This shift coincided with the pandemic, bringing numerous learning opportunities along the way, including owning a virtual business and customer acquisition.- Chapters - 00:00 - Introduction 3:10 - Entrepreneurial background 6:22 - Funding the business 7:30

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28:13

Navigating numbers and networking as an entrepreneur

Side Hustle to Small Business ·

2024/10/02

When Samantha Mittman Besnoff started college, she had dreams of being an accountant at a one of the big 6 firms. However, after having children, she discovered that she wanted the flexibility that a traditional 9 to 5 cannot offer. She then turned her side hustle of helping folks with their taxes into her full-time gig. Now, Samantha runs Your Financial Maven, a successful accounting business. She also hosts the Your Financial Maven podcast.- Chapters - 00:00 - Intro 4:15 - Entrepreneurial

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25:20

How Monica Helvie helps herself and others navigate...

Side Hustle to Small Business ·

2024/09/25

Monica Helvie started her career as a licensed therapist in community mental health, but found it challenging to balance her personal life with her work, causing her to experience intense burnout. In 2018, she decided to open her own private practice, giving her the freedom to set her own hours and choose her clients. Using the skills she learned with her burnout experience, Monica specializes in helping clients navigate their own experiences with burnout. - Chapters - 00:00 - Intro 3:02 -

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22:50

Healing from addiction and empowering others to thrive

Side Hustle to Small Business ·

2024/09/18

Tiffany Hopkins is a certified health coach and nutrition specialist. Having experienced substance abuse in the past, Tiffany has found her passion in helping individuals, and more specifically mothers, take back control of their lives by quitting alcohol. She is the founder of two companies: her own private counseling practice and Mind and Body Restoration LLC, a sober health coaching business. - Chapters - 00:00 - Introduction 4:21 - Entrepreneurial background 8:52 - Business challenges and

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186 results

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