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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

35:07

Sell it like a mango? Donald Kelly can teach you how

Side Hustle to Small Business ·

2023/02/22

Growing up in Jamaica, Donald Kelly saw his family members and neighbors selling goods and services on every corner. Naturally, Donald believed that to be an entrepreneur, you had to first and foremost be a salesperson. Since then, he's gained life and business experience while moving to the US, starting a podcast, and writing a book. But Donald still draws on his childhood experience selling mangoes in Jamaica as a metaphor for successful sales.

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35:08

From designing video games to getting funded by Mark...

Side Hustle to Small Business ·

2023/02/15

Rob Kischuk started his career designing video games for Facebook in the days of FarmVille. When Rob was laid off, along with 90% of his team, he asked himself, “What now?” Since then, Rob has started four software-based businesses, one of which acquired funding from Mark Cuban at a serendipitous Super Bowl Shark Tank watch party. Throughout his 10 years in the startup world, Rob has learned to take risks: you never get what you don’t ask for.

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32:20

Accepting feedback, iterating, and getting better

Side Hustle to Small Business ·

2023/02/08

Born in France to entrepreneur parents, Nicolas Billaiche learned the value of having a community of fellow business owners. But when he left his corporate career in sales and founded eStreamly, he was bombarded with opinions. Nicolas didn't take this constructive criticism personally but used it to inspire action. With the help of his business partner, he's learned to accept feedback and adapt his game plan but ultimately trust his gut.

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31:05

From ”unemployable” to 27 years in business

Side Hustle to Small Business ·

2023/02/01

When Steve Zehngut earned a degree in film and began working in the entertainment industry, he realized it wasn't for him. He transitioned to a graphic design agency, which wasn't a fit either. Was Steve unemployable? No. He was just a misplaced entrepreneur. In 1995, Steve left the corporate world for good. He founded Zeek, which has grown to become Southern California's leading web, interactive, and mobile development agency.

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33:30

Taking advantage of every learning opportunity

Side Hustle to Small Business ·

2023/01/25

Maddy Osman draws on past experiences as she manages her SEO content agency, The Blogsmith. Growing up with an entrepreneur dad, she understands that owning a business requires intentional boundaries. Her previous job in the Groupon sales department taught her that rejection isn’t personal. Freelance writing for a Chicago lifestyle blog sharpened her SEO skills. Maddy uses these lessons learned to improve — both herself and her business.

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32:54

Coordinating win-win solutions for his project teams

Side Hustle to Small Business ·

2023/01/18

Todd Ward combines his design background and general contracting experience as an independent owner’s representative and project manager. He assists his clients with their building projects — anything from development, to new construction, to remodeling. Todd attracts repeat customers because he knows the only way you can reach a win-win solution is if you know what winning means to the other side.

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29:22

Counting on family for inspiration, support, and purpose

Side Hustle to Small Business ·

2023/01/11

Family plays a critical role in Nathan Hamilton’s life. His loved ones have been with him at every step of his business journey as he’s grown In A Lifetime Photography, based in Houston, Texan. Nathan’s uncle taught him film photography in high school. The birth of his daughter prompted him to start a side hustle to gain a flexible schedule. Today, his wife and two kids encourage him to dream big, have fun, and get rest.

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33:24

Pitch Perfect: How Rob Friedman became the Pitching...

Side Hustle to Small Business ·

2023/01/04

Though Rob Friedman trained and practiced as a lawyer, his passion was coaching and playing baseball. In 2014, he dove into the world of content creation. His niche? Not just baseball, but pitching specifically. Pitching Ninja was born. Since starting Pitching Ninja, Friedman has amassed over 400,000 Twitter followers, 100,000 Instagram followers, and appears on TV networks like Fox Sports and Peacock as a Pitching Analyst.

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32:17

Taking the Stage: Courage, Confidence, and Charisma

Side Hustle to Small Business ·

2022/12/14

ShaVonne Davis is a former classroom teacher who channels her love for theatre arts into her small business, Acting with Mrs. Davis. Acting With Mrs. Davis is a Theatre Arts Education Company that provides after-school programs, classes, workshops, and education consulting. ShaVonne teaches her students culture, self-confidence, and creative expression and understands that when you do good work, success will follow.

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28:26

Waiting for the perfect time might be delaying your...

Side Hustle to Small Business ·

2022/12/07

Angel Hendrix knew that her season of contributing to her job was over and she wanted to do more, but what was next? She wanted to get into real estate without having to be a Realtor; so she took a notary class, and her business took off from there. Now Angel has several lines of business, is an example of entrepreneurship to her daughter, and is looking to hire some help to take her business to the next level.

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34:05

Starting a side hustle within an existing, thriving...

Side Hustle to Small Business ·

2022/11/30

Just because your business is thriving doesn’t mean it’s perfect for you. That’s one thing Dr. Karen Jacobson realized as she started to transition from her thriving chiropractic practice to something new. One of the hardest parts of that process was leaving the safety of what is known, for the adventure of what is unknown, and answering the question many entrepreneurs struggle with: When do I take the leap?

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30:34

Quit your job with no plan? Sometimes it works out.

Side Hustle to Small Business ·

2022/11/16

Have you ever wondered what would happen if you just quit your job with no plan for what you would do next? In this episode Sanjay talks with Jim Garrison who did just that. Thirty-two years later, Jim has a successful business and reflects on the twists, turns, and lessons he learned along the way. He also has great advice if you are thinking of making the same jump: “Don’t be afraid and start today.”

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37:46

Building confidence while building a business

Side Hustle to Small Business ·

2022/11/09

After getting his first computer at age 9, Larry Dukhovny began his life as a self-proclaimed computer geek. This passion for technology prompted his career path in IT consulting. After freelancing for six years, Larry founded MyBizGeek in 2013. Passionate about believing in yourself and the value of your service, Larry now advocates for building inner confidence to accelerate your business and attract new clients.

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25:24

Grant Nichols’ personality type? Entrepreneurial

Side Hustle to Small Business ·

2022/11/02

When it comes to personality types, there is Meyers Briggs and StrengthsFinder, among others. But Grant Nichols uses a more general term when describing himself: entrepreneurial. He constantly brainstorms new business ideas, researches their market potential, and vets the project’s viability with his friends and family. Grant founded his current business, BluWave Technologies, to help manufacturing companies increase operational efficiency.

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29:01

Speaking from experience: Inspiring hope and evolution

Side Hustle to Small Business ·

2022/10/26

Jacari Harris is an author, sought-after speaker, and social media influencer who uses his experience growing up in the foster care system to inspire hope and encourage transformation. As his tenure as Executive Director of the George Floyd Memorial Foundation closes, Jacari Harris is preparing for what’s next: increasing his influence at speaking engagements and growing his coaching business, Stimulating Success.

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29:40

Fostering a fun, inclusive, and professional environment

Side Hustle to Small Business ·

2022/10/19

After spending ten years in the financial services industry, Jennifer Stine knew she wanted to create something of her own. Inspired by her entrepreneurial dad, she founded Fortune Web Marketing in 2007. Over the past 15 years, Jennifer’s company expanded outside her home state of New Jersey with a growing group of colleagues. As president of her company, Jennifer works to create an inclusive and non-corporate environment where her team can flourish.

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29:35

Maximizing discoverability using systems and social...

Side Hustle to Small Business ·

2022/10/12

Lloyd George, better known by his name on all social platforms, “Lloyd Not George,” is a podcast producer and social media influencer. He creates informative content for beginner podcasters and has accumulated over 300,000 views on TikTok. Lloyd balances his full-time job with his podcasting side hustle by using various systems to manage his time, automate sponsor outreach, and engage with fellow online creatives.

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27:14

Straight to your inbox: Email marketing, mastered

Side Hustle to Small Business ·

2022/10/05

Do you think email is dead? Paige Parrino knows email marketing is alive and well. While working at her first corporate job after graduating, Paige saw firsthand the value of email marketing on a business and realized that her skills were in high demand. With her husband deployed and more free time on hand, Paige dreamed, researched, and started her company, Paige Parrino Marketing, which supports e-commerce businesses' marketing efforts.

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34:30

Growing together as partners, founders, and business...

Side Hustle to Small Business ·

2022/09/28

Ali Green and Mickey Mellen had a history of outsourcing work to one another. After years of back and forth, they realized it would make sense to start a company together. In 2009, they founded GreenMellen Media, a digital marketing agency based in Marietta, Georgia. Since then, Ali and Mickey have opened a physical office, hired a team of six, adjusted their schedules to meet life’s changing demands, and become stronger partners in the process.

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25:45

Having courage to fail, reassess, and move forward

Side Hustle to Small Business ·

2022/09/21

For Matt Davis, Man Cave Basics Plus began as a hobby when he would peruse outdoor flea markets and vintage shows. Three years ago, Matt started developing the Man Cave brand in earnest. Throughout his career - from joining and then leaving the family business, to monetizing his fascination with patent prints, to now growing Man Cave Basics - Matt has taken some risks that paid off and some that didn’t, but he learned from all of them.

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187 results

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