Employee To Boss: Entrepreneurship, Side Hustles, and Business Growth Tips from Experts

Today we are talking all about insurance, but making it fun and interesting!

Katherine Phillips is a licensed insurance broker from Florida. She owns her own insurance business, specializing in health insurance and life insurance, and is Medicare certified. She is also certified on the state and federal marketplaces and is contracted with all major carriers across the country.

Starting out with zero knowledge of insurance or business, Katherine shares into how she took the leap from employee to boss, the strategies she used to succeed, and how she manages her income in a commission-based career. Katherine sheds light on common misconceptions about health insurance for self-employed individuals, providing actionable advice for entrepreneurs who need support but don’t know where to start.

Katherine helps individuals and families find a custom plan that is affordable and meets their unique needs. She is passionate about helping others and educating about insurance. Before obtaining her insurance license, Katherine attended the University of Colorado Denver and received degrees in public health and health communication.

With tips on financial planning, finding the right insurance, and structuring business finances for long-term success, this episode is packed with insights for anyone considering a leap into entrepreneurship.

In this episode:

• Katherine’s journey from college grad to commission-based insurance broker.
• How entrepreneurs can manage their insurance needs without an employer’s benefits.
• Financial management tips for commission-based income and navigating cash flow.
• Why having a mentor, investing in your business, and a growth mindset are crucial for success.

Action Steps for the week:

1. Don’t let fear of failure hold you back; take a chance, even if rejection feels likely.
2. Dream big and set ambitious goals for your business and personal growth.
3. Focus on helping others and building genuine relationships; success will follow.

Connect with Katherine:

https://katherinephillipsinsurance.com/

https://www.facebook.com/HealthMarkets.Katherine.Phillips/

Book a time with me: https://calendly.com/katherinephillipsinsurance/15-minute-telephone-meeting

Read Reviews on Google: https://g.co/kgs/EQA1Fna

Connect with me, Hayleigh Hayhurst:

Website: https://www.espressopodcastproduction.com/

YouTube: https://www.youtube.com/@EspressoPodcastProduction

Instagram: https://www.instagram.com/espressopodcastproduction/

TikTok: https://www.tiktok.com/@espressopodproduction

Music: John Kiernan. www.johnkiernanmusic.com

Produced by Espresso Podcast Production: https://www.espressopodcastproduction.com/

Join the Conversation: What did you think of this episode? Share your thoughts and key takeaways with me on social media using the hashtag #EmployeeToBoss. If you enjoyed this episode, please leave a review and share it with your network.

Entrepreneurship doesn't have to be a lonely road anymore.
This week’s guests (and the first guests on the Employee To Boss Podcast!!!!) are Teri and Sarah, founders of Females Who Side Hustle, a community for like-minded motivated females to connect, feel support, and gain resources. Their mission is to create a space for meaningful connections through open conversations and shared experiences.
In this episode, we talk all about the struggles that entrepreneurs face, how to tell your friends and family about your side hustle, and how to get brand partnerships!
Why is there such a shame about having a side hustle? Having a side hustle should not be a hush-hush situation. It can literally feel scarier to tell your boss or your mom about your side hustle than telling a random stranger on the internet.
Just because you have a side hustle does not mean that you want to leave your job (most of the time) you just have different cups to fill.
The vibes between Sarah and Teri are unreal and they have such a cool “coming together” story. Not only are they are 10 years apart in age, but Sarah was also once Teri’s post-grad student. Once the duo became colleagues, they really connected and decided to start a business.
Teri started her first side hustle 10+ years ago and after being on maternity leave, she felt super alone in business. She wanted a partner-in-side hustle, reached out to Sarah, and after a coffee date, Females Who Side Hustle was born. They both wanted something more than just their 9-5. They wanted to express themselves creatively and wanted to create a space for women to build their network across industries and find conversations that inspire them along the way.
The goal is to bring more females to the table, ditch competition, and encourage all to lift each other up and collaborate. While normalizing the struggles entrepreneurs face in doing it
all between business and life.
You should tell people about your side hustle, it is impressive.
They started with just a few hundred followers, and since their launch in 2019, they have grown to a community of over 10k, organically!
Topics in this episode:
Comparison is death to your business
How to find a business partner
How to tell people about your side hustle because it can be scary
How to get brand partnerships
Your Challenge this week:
Just start - get that Instagram, get that email address
Be consistent and just go with the flow including the ups and downs
Lead with your side hustle. When someone asks you want you to do, lead with what you are passionate about
Connect with Teri and Sarah:
Website: https://www.femaleswhosidehustle.com/
Instagram: https://www.instagram.com/femaleswhosidehustle/
Save Her Seat podcast: https://www.instagram.com/saveherseat/
Connect with me, Hayleigh Hayhurst:
Instagram: https://www.instagram.com/espressopodcastproduction/
Facebook Group: https://www.facebook.com/groups/espressogrowth
Website: https://www.espressopodcastproduction.com/
Music: John Kiernan. www.johnkiernanmusic.com

Monique AJ Smith, a Veteran Athletics Administrator with over 30 years of experience, joins the Employee to Boss podcast to talk all about being a female leader. In this episode, Monique talks about how she was laid off, went full time into her consulting business Seeds of Empowerment LLC full-time March 2013.

Monique shares her personal story, how she opened herself up to new opportunities, getting exposure, niching down to empower more people, women confidence, and her “LEARN” The Game Framework.

For more than 22 years she has provided consultation on Title IX, NCAA compliance, and rules education as well as served on several NCAA Committees. For 2 years she served as consultant to the NCAA Leadership Development Department by conducting campus and conference workshops for student-athletes and athletic administrators.

Monique host the nationally recognized weekly podcast “A Chat in the Garden® with Monique A.J. Smith” where women in Higher Ed, specifically Athletic Administration are spotlighted. The listener base has grown to over 1.5K member private Facebook community where topics such as Depression for the High Achiever, How to become an AthleticPreneur TM and Women Leading Football Programs are discussed with experts in the former of webinars. Monique likes to say, “the Garden identifies the need and I go out find resources to feed that need”.

Action steps:

1. Commit to being a lifelong learner.
2. Embrace email lists.
3. Create a community

Connect with Monique:

LinkedIn: https://www.linkedin.com/in/monique-a-j-smith-44a5725/

Listen to Monique’s Podcast: https://seeds-of-empowerment-courses.thinkific.com/users/checkout/auth

Website: https://seedsofempowerment.info

Significance in Athletics and Sport Magazine: https://www.amazon.com/Significance-Athletics-Sport-Monique-Smith/dp/B09C3GLBNN#:~:text=Significance%20in%20Athletics%20and%20Sports%20Magazine%20is%20a%20Bi%2DAnnual,next%20generation%20in%20the%20industry

Connect with me, Hayleigh Hayhurst:

Website: https://www.espressopodcastproduction.com/

Watch the Podcast Videos on YouTube: https://youtube.com/@hayleighhayhurst2129?si=xuAef9AghhOJfhnA

Instagram: https://www.instagram.com/espressopodcastproduction/

TikTok: https://www.tiktok.com/@espressopodproduction

How to be an Unforgettable Guest course: https://hayleigh-s-school-2cca.thinkific.com/courses/great-guesting-how-to-be-an-unforgettable-podcast-guest

Use my favorite business resources:

Edit your podcast with Descript: https://www.descript.com?lmref=KkInCQ

If you are a small business owner like me, you need a CRM. Sign up for Dubsado: dubsado.com/?c=espresso

ConvertKit — ConvertKit is the go-to marketing hub for creators that helps you grow and monetize your audience with ease.: https://convertkit.com?lmref=gBnOLg

Try Audible Premium Plus for free: www.audibletrial.com/QyNjxo

Music: John Kiernan. www.johnkiernanmusic.com

Business does not need to all look and feel the same. Business can be whatever you want it to be!

Natalie De Vincenzi, a business mentor, founder of You Are Enough Co and digital nomad, joins the podcast today to talk all about business and how it should align with the life you want to live.

She provides invaluable advice on shifting from an employee mindset to an entrepreneurial mindset, the importance of identity work, and highlights the necessity of balancing life and business.

Her Business Mentorship: for kind-hearted, ambitious, female entrepreneurs who crave confidence, making an impact, and authentically growing their business. As a mentor, I focus on the business + the human behind the business through my signature combination of mindset, heartset, and business strategy.

You Are Enough Co: an apparel company focused on mental health awareness. They are dedicated to uplifting others and reminding each other we are enough. 100% of proceeds go to mental health awareness & research.

Action Steps:

1. Get clear on the legacy that you want to leave
2. Adopt a “why not” mentality
3. Think about your identity and if you are acting now as who you want to be

Connect with Natalie:

Instagram: https://www.instagram.com/coaching.by.natalie

You Are Enough Co.: https://youareenoughco.com

The Business with Heart Podcast: https://podcasts.apple.com/us/podcast/the-business-with-heart-podcast/id1719395508

Natalie’s recommended reading list: https://docs.google.com/document/d/1aMCv7Ny5APRIeHnVitiHnFyXXbtU10ehaABtOhOO2zI/edit?usp=sharing

Connect with me, Hayleigh Hayhurst:

Website: https://www.espressopodcastproduction.com/

YouTube: https://www.youtube.com/@EspressoPodcastProduction

Instagram: https://www.instagram.com/espressopodcastproduction/

TikTok: https://www.tiktok.com/@espressopodproduction

Music: John Kiernan. www.johnkiernanmusic.com

Produced by Espresso Podcast Production: https://www.espressopodcastproduction.com/

How Alexa Philips Transitioned from Corporate to Freelancing Success!

Alexa Phillips is a content strategist, brand marketing consultant, and multi-passionate creative. With almost a decade of marketing and writing experience, Alexa has worked with Fortune 500 brands, startups, and creative entrepreneurs to grow their brands through content marketing. She is the founder and Chief Brand Architect at Bright Eyes Creative, a creative studio that helps businesses create content-driven brand experiences. She is also the author of Creatives Anonymous, a weekly newsletter about navigating creativity in the 21st century.

We discuss Alexa's experiences in transitioning from an employee to an entrepreneur, the impact of corporate pressure on mental health, and the importance of leveraging personal connections.

She also shares actionable marketing strategies with long-form content, and how to do a self audit on your brand.

Alexa is also the queen of hot takes, and shares her best content hot takes with us, including one about AI that has kept me thinking since this episode!

Action Steps:

1. Start noticing what you like on social media, and why it stands out to you.
2. Do a brand audit of yourself to see if you are happy with the direction your business is going.
3. Don’t be afraid to writing content - just put pen to paper

Connect with Alexa:

Website: https://www.brighteyescreative.co

Musing to Monetized: https://www.brighteyescreative.co/musing-to-monetized

Instagram: https://www.instagram.com/brighteyescreative/

Connect with me, Hayleigh Hayhurst:

Website: https://www.espressopodcastproduction.com/

YouTube: https://www.youtube.com/@EspressoPodcastProduction

Instagram: https://www.instagram.com/espressopodcastproduction/

TikTok: https://www.tiktok.com/@espressopodproduction

Music: John Kiernan. www.johnkiernanmusic.com

Produced by Espresso Podcast Production: https://www.espressopodcastproduction.com/