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.

  • 34 minutes 59 seconds
    Empowering educators from beyond the classroom
    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 Long Lines of Educators
    00:04:30 Impact of Great Teachers

    00:06:20 Professional Learning Communities

    00:08:49 Budgeting in Your Side Hustle

    00:12:34 Side Hustle to Full-Time Hustle

    00:15:18 Data Tools for SEO

    00:18:15 Learning other Languages

    00:22:07 Bumping Elbows with Elites

    00:27:03 Balancing Business at Home

    00:28:59 Outsourcing for Optimization

    00:32:24 Closing

    22 January 2025, 12:00 pm
  • 49 minutes 9 seconds
    Entrepreneurs Roundtable: Marketing for Small Businesses
    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 Background

    00:07:44 The Attention Economy

    00:09:02 Unify Your Marketing Voice

    00:13:44 Balance Between Branding and Performance

    00:20:08 Competitive Audits and Analysis

    00:25:39 The Affect of Influencer Marketing

    00:34:28 Enhancing Customer Experience

    00:36:07 Marketing Mistakes

    00:39:39 QA & QC for Marketing Process

    00:42:46 Emerging Strategies

    00:45:38 Closing

    15 January 2025, 12:00 pm
  • 30 minutes 58 seconds
    From bartender to multi-million dollar restaurateur
    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 Roots

    00:07:55 Buying VS Starting Businesses

    00:10:04 First Year Losses

    00:12:42 Pandemic Pivots

    00:16:14 Elevated And Edgier Concepts

    00:18:36 Bartender to Entrepreneur

    00:23:34 Sam Malone at Cheers

    00:26:42 Living Humble

    00:29:07 The Best Apps

    00:30:29 Closing

    8 January 2025, 12:00 pm
  • 24 minutes 50 seconds
    RERUN - How D.R. Fay found entrepreneurial success later in life

    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 - Overcoming nerves

    11:29 - Managing stress & health problems

    21:00 - Advice for other entrepreneurs

    23:21 - Closing and contact

     
    1 January 2025, 12:00 pm
  • 27 minutes 57 seconds
    RERUN - How to turn past experiences into entrepreneurial success

    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 skills

    11:14 - Overcoming nerves

    12:47 - Having a business partner in a different state

    15:32 - Balancing stress

    17:33 - Setting boundaries

    22:37 - What Matt would have done differently

    26:02 - Advice to other entrepreneurs

    26:35 - Closing and contact information

    25 December 2024, 12:00 pm
  • 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
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