Side Hustle to Small Business

Hiscox

Side Hustle to Small Business tells the stories of people who took their first step as an entrepreneur while still working a full-time job. Each week, entrepreneurs open up about their first steps and choices made, sharing business insights and lessons learned. If you’re thinking about starting a side hustle this is your chance to learn from entrepreneurs who have built something from nothing. And, if you’ve already started your own business, Side Hustle to Small Business offers practical advice to help you chart your own course.

  • 33 minutes 39 seconds
    How writing recharged Aaron Ryan’s creative spirit
    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 Background

    00:03:35 What’s A Kool Aid Stand?

    00:05:57 The 80’s Comic Books

    00:11:29 Writing A Book Every Sixty Days

    00:15:24 Dissonance: The Lack Of Harmony

    00:17:19 Do You Believe?

    00:21:48 Pear-Shaped Men

    00:25:36 Entrepreneurial Blurred Lines

    00:27:02 Listening To The Voice Within

    00:30:15 Endorsement Does Not Equal Trajectory

    00:33:10 Closing Remarks

    18 December 2024, 12:00 pm
  • 35 minutes 19 seconds
    Growing a partnership in life and entrepreneurship
    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 Background

    00:02:24 Side Hustle, Small Business, Marriage

    00:05:41 Peddling Up The Ladder

    00:09:57 Excitement Outweighing Risk

    00:10:50 Burning Out And Growing Up

    00:14:38 NFTs Are A NO

    00:16:51 Shifting The Infield

    00:20:43 Failure Will Fix It

    00:24:39 Fundraising Frenzy

    00:30:52 Opportunity In AI

    00:34:08 Closing

    11 December 2024, 12:00 pm
  • 32 minutes 33 seconds
    How Winnifred Tataw went from author to publisher
    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.
    4 December 2024, 12:00 pm
  • 31 minutes 7 seconds
    How a Christmas gift turned into a six-figure business
    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 Coffee: The Cottage Food

    00:04:40 Bottlenecks of Business

    00:08:18 Transitioning from Side Hustle

    00:10:10 Illicit Deals

    00:12:27 Growing Organically

    00:15:33 Certified Coffee Cuppers

    00:19:29 Working hard or hardly working?

    00:21:10 Origin of the Month

    00:23:10 Overcoming Fear, Moving Forward

    00:25:10 “Well, that’s cute.”

    00:26:58 The ROASTMASTER

    00:30:04 Closing

    27 November 2024, 12:00 pm
  • 30 minutes 40 seconds
    Building a supportive community to benefit your children
    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 Background

    00:03:14 A Lack of Resources

    00:05:26 The Catalyst for Change

    00:08:55 “This is Awful”

    00:10:57 Complex Kids

    00:12:18 Deep Dive on Diagnosis

    00:15:19 Putting Yourself Out There

    00:16:57 The Big Picture

    00:19:47 It Takes a Village

    00:23:42 Misinformation

    00:28:05 They Need You

    00:29:40 Closing

    20 November 2024, 12:00 pm
  • 27 minutes 30 seconds
    How Stephanie Shanks increased her revenue by tenfold

    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 all in 9:17 Setting rates 12:47 Overcoming nerves 14:38 Investing back in the business 16:25 Balancing life and the business 18:04 Finding your personal style 21:11 Managing stress 23:37 Setting boundaries 25:15 Looking back 25:50 Advice for other entrepreneurs 26:28 Closing
    13 November 2024, 12:00 pm
  • 29 minutes 39 seconds
    Creating a global community through podcasting

    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 space for your new business 11:43 Overcoming nerves 13:23 Revenue 18:02 Managing a side hustle while working full-time 21:18 Looking back on the business 22:57 Advice for other entrepreneurs 26:28 Technology recommendations 28:07 Closing and contact
    6 November 2024, 11:00 am
  • 31 minutes 46 seconds
    Amity Gleason’s journey from Attorney to Jewelry Maker

    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 process

    10:35 - Overcoming fears and finding clients

    14:11 - Work-life balance

    16:14 - Building your brand

    18:58 - Saving money

    22:08 - Entrepreneurship and parenthood

    25:39 - Setting boundaries

    27:36 - Looking back

    28:30 - Advice for other entrepreneurs

    30:05 - Closing and contact

     

    30 October 2024, 11:00 am
  • 28 minutes 15 seconds
    How Bonnie Conrad went from furniture builder to marketer
    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 - Entrepreneurial background

    10:59 - Overcoming nerves and starting the business

    13:15 - Balancing life and entrepreneurship 

    15:31 - Merging with another business

    20:00 - Helpful technology and apps

    20:40 - Looking back

    23:46 - Advice for other entrepreneurs 

    25:53 - Social media strategy advice

    26:49 - Closing and contact

    23 October 2024, 12:00 pm
  • 30 minutes 27 seconds
    How Ryan Klee leads with purpose through thought leadership
    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 - Venturing into entrepreneurship

    7:46 - Finding clients

    9:18 - Origin of the company name

    10:13 - Shifting business models

    17:41 - Resonating with clients

    22:30 - Looking back

    26:31 - Advice for fellow entrepreneurs

    28:34 - Closing and contact

    16 October 2024, 12:00 pm
  • 33 minutes 37 seconds
    ​​How your perspective on entrepreneurship can evolve over time
    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 - Impact of the pandemic

    8:50 - Overcoming nerves

    10:28 - Finding your market and services offered

    14:55 - Tracking costs and customer acquisition

    17:52 - Making the leap into full-time entrepreneurship

    26:58 - Health and Wellness

    29:47 - Reflecting back on the business

    32:00 - Closing and contact

    9 October 2024, 12:00 pm
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