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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

33:50

Overcoming your fears and achieving your dreams

Side Hustle to Small Business ·

2023/07/12

Brooke Monaghan has always known she has wanted to work for herself. However, when she went to start her consulting business, she was initially very scared. In today’s episode, Brooke and Sanjay discuss how to overcome fear when it comes to the risk aspect of running your own business, building relationships, and asking for help. Her advice? Either do it and maybe fail or don’t do it and absolutely fail, but always know your worth.

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26:17

Connecting businesses with the grants they need

Side Hustle to Small Business ·

2023/07/05

Danita Doleman has over 25 years experience providing strategic solutions to businesses in need. She is an expert in connecting people to grant opportunities and to this day, she has helped individuals earn over $8 million in grants. Recently, Danita’s company, SEAS Community Partners, launched “Grants4Biz”, a service which seamlessly connects individuals and businesses to grants they qualify for. Tune in to this episode the learn more about grants for small businesses and resources to identify the

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29:26

How Maria Romano found her passion in the business of...

Side Hustle to Small Business ·

2023/06/28

Maria Romano is a Minister, wedding officiant, podcast host, author, and motivational speaker. Through her company, True Love Knots, Maria has officiated over 5000 weddings, and created courses on becoming officiated yourself. Prior to finding her passion in the business of love, Maria's entrepreneurial journey began with a rental car company, granting her extensive expertise in business management.

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32:19

Transitioning from the startup world to freelance

Side Hustle to Small Business ·

2023/06/21

After earning a degree in Entrepreneurial Studies, Jacob “Jeb” Burt started his career in the food and beverage industry, working at a startup. When the startup folded, he began working freelance gigs to pay the bills. When making the decision to either continue freelancing or get full-time work, Jacob decided to continue down the freelance path and build his company, BURT. Now, Jacob has his own team that specializes in building media brands.

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32:07

Starting a business that aligns with your passions

Side Hustle to Small Business ·

2023/06/14

Bonnie Mauldin has been hustling since she was a kid. At eight years old, she was knocking on doors offering to shovel driveways. After graduation, she entered the medical field, but quickly discovered it was not for her. Now, Bonnie owns two successful businesses, The Mauldin Group and Mauldin Production Company. Having learned a lot along the way, Bonnie shares her tips on changing careers, side hustles, and running multiple businesses.

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32:21

Exploring the ins and outs of freelancing in today’s...

Side Hustle to Small Business ·

2023/06/07

Josh Bernstein joins us today to talk all things freelance. As the owner of Josh Bernstein Media, Josh is an expert in Google Ads and paid search and has been running his own business for over 10 years. Sanjay and Josh sit down to debunk myths about freelancing, give important tips on starting out, discuss maintaining a healthy work-life balance while being your own boss, and suggest when to choose a freelancer over an agency.

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37:36

Improving the work environment by going solo

Side Hustle to Small Business ·

2023/05/31

Rita Ernst wasn't happy with the work environment in the large corporation where she was worked. With a new baby at home, the stress was overwhelming, so she decided to become her own boss. She is now an Organizational Psychologist and Consultant and founder of Ignite Extraordinary, and author of a book on workplace positivity. Hear what Rita has to say about work-life balance and why networking is so important in finding clients that align with your skills and professional goals.

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34:11

Giving equal priority to business, body, and brain

Side Hustle to Small Business ·

2023/05/24

Kendrick Disch started his branded content studio, Vertical River, in 2019. Before starting his business, Kendrick was a video production manager, studio manager, and photographer. Today, he’s focused on growing Vertical River through ‘sustainable storytelling’ while prioritizing his health as a new founder. By giving equal priority to his business, exercise, and personal relationships, Kendrick sets himself up for success.

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31:33

Inspired by her kids, Monique dishes up SoulFull cooking

Side Hustle to Small Business ·

2023/05/17

As a mom to two young children, Monique Henderson not only planned birthday parties but also cooked for all the guests. When her cooking garnered positive praise, Monique thought, “I could make this a side hustle.” In 2017, she began her catering business, SoulFull Caterers, which serves customers in the Washington DC area. Monique’s goal? Buying a food truck, so she can bring home cooking on wheels to events, fairs, and college campuses.

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36:16

Moving from Wall Street to three-time entrepreneur

Side Hustle to Small Business ·

2023/05/10

Yong-Soo Chung always knew he wanted to own a business. While working on Wall Street, he dreamed of running a hedge fund. When he left finance and bought a one-way ticket to California, his dream of owning a business remained unchanged, but the product he offered shifted. Since 2015, Yong-Soo has founded three companies: Urban EDC, a carry gear brand; Growth Jet, a third-party logistics provider; and Spotted By Humphrey, a curated dog boutique.

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24:09

Prioritizing alignment while managing a remote team

Side Hustle to Small Business ·

2023/05/03

John DeShazer is the President of LogicSpree, where he works to make Salesforce simple for small and mid-market organizations. As his business and fully remote 11-person team grow, John focuses on alignment. By standardizing work hours, the LogicSpree team achieves two goals: collaborate in real-time and set clear work-life boundaries. This structure also aligns with John’s primary goals: to be stable, happy, have enough, and reduce stress.

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29:45

Building a strong foundation for her new creative agency

Side Hustle to Small Business ·

2023/04/26

Heather Gibbons is a wife, mother, twin sister, and musician. She’s also the co-founder of INMO Creative, a full-service creative agency based in Atlanta. As Heather and her business partner, Simon, establish their agency in its first year of business, they focus on the “simple things.” Together, they’re committed to building a solid foundation of systems and processes that aligns with their beliefs, values, and mission.

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29:03

Mastering social media to help other small businesses

Side Hustle to Small Business ·

2023/04/19

With a creative writing and data analysis background, Lauren Ramsey brings her skills to the table as the founder and Chief Engagement Officer at Betsy Bash. Founded in 2010, Lauren and her team help local businesses get more leads and make more sales using social media. She’s taken her business from her hometown of Houston to her new home in Chicago, but her passion has stayed rooted: helping small businesses make a bigger impact.

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31:53

Keeping her side hustle while starting a new...

Side Hustle to Small Business ·

2023/04/12

Jennifer Bourn has been self-employed for 17 years. She started her creative services agency, Bourn Creative, in 2005 and added on a side hustle, teaching courses and workshops in 2017. When Jennifer’s best friend offered her a full-time job, Jennifer was intrigued but also had conditions. She would accept the job, but her side hustle had to stay up and running. A compromise was reached, and now Jennifer has the best of both worlds.

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32:49

How a pandemic-forced pivot paid off long term

Side Hustle to Small Business ·

2023/04/05

Michael Cox has been in the corporate sales recruiting world for 20 years. But when his recruiting side hustle yielded more profit and control, Michael realized he could open his own business. He founded Zag Worx in late 2019. Starting a business in the wake of a global pandemic with few companies hiring, Cox was forced to innovate. He transitioned from full-service recruiting to offering highly-specific services tailored to his client's needs.

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30:56

Selling sneakers as a side hustle? Possible and...

Side Hustle to Small Business ·

2023/03/29

Chris Casseday always loved collecting shoes. Not just shoes in general, but really, really nice sneakers. Twenty years ago, he began selling collectible sneakers on eBay. As his experience and sales volume grew, he founded 513 Kicks. Since 2017, Chris has managed 513 Kicks solo while working full-time as a Director of Operations. For Chris, selling sneakers isn’t just a hobby. It’s a fun — and profitable — side hustle.

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30:29

How simplified product offerings helped business Liftoff

Side Hustle to Small Business ·

2023/03/22

Joe Casabona started Podcast Liftoff in 2017. He helps his clients transform their podcasts from a hobby to a revenue-generating machine. In 2022, Joe realized that he was providing too many services to his customers. Instead of a jack of all trades, he wanted to be known as the guy who eats, sleeps and breathes podcasts. He adapted his product offerings and is now learning that, when it comes to your business, sometimes less is more.

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34:22

Opening his own business and breaking industry standards

Side Hustle to Small Business ·

2023/03/15

During his 26 years in the web design industry, Wayne Pelletier designed thousands of websites. He also learned the patterns that cause frustration and communication breakdowns between web designers and their clients. So when Wayne started his company, Resonant Pixel, in 2020, he employed a different business model that broke the mold of standard website services. Instead of a lump-sum investment, his team uses a subscription-based model.

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29:27

Mixing arts and philanthropy with Kentucky bourbon

Side Hustle to Small Business ·

2023/03/08

Morgan Hancock is full of ideas and energy, and her work life reflects those qualities. She’s a commercial real estate agent, US Army veteran, mother of two, and passionate advocate of the arts. Most recently, Morgan founded Bourbon with Heart, a nonprofit with a mission to leverage the influence and popularity of bourbon to raise funds for local charities while also providing a first-class arts experience for Kentuckians.

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33:32

Cheers! How Melissa Zeman creates community with wine

Side Hustle to Small Business ·

2023/03/01

In 2009, Melissa Zeman said, “Someday, I’m going to open a wine shop that focuses on community.” She got to work, and ten years later, Melissa opened Bottles Up!, a wine shop and experience in the Lakeview East neighborhood in Chicago. Through in-store events and collaboration with other local vendors, Melissa’s business model has centered around “retail-tainment” — creating, educating, having fun, and, most importantly, connecting.

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187 results

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