Side Hustle to Small Business

By HiscoxBusiness Entrepreneurship Careers

Side Hustle to Small Business episodes

January 29, 2025 How Josh Russell built success on his own terms
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 Background
00:04:33 The Hustler Mentality
00:06:28 Genres of Entrepreneurship
00:07:56 Shedding a Business
00:11:07 Get Rid of Imposter Syndrome
00:13:34 “If You’re Not Terrified, You’re Not Charging”
00:17:04 Entrepreneurialism and ADHD
00:22:14 Comfort in the Uncomfortable
00:24:33 Extensions of AI
00:26:45 Side Hustling with an iPhone
00:27:51 Focus = Fast Growth
00:31:08 Closing
32 min
January 22, 2025 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
35 min
January 15, 2025 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
50 min
January 08, 2025 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
31 min
January 01, 2025 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
25 min
December 25, 2024 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
28 min
December 18, 2024 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
34 min
December 11, 2024 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
36 min
December 04, 2024 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.
33 min
November 27, 2024 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
32 min

About Side Hustle to Small Business

From the publisher's feed

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.…