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

By Hayleigh Hayhurst, Podcast Producer & StrategistBusiness Entrepreneurship

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

November 05, 2024129. How to Secure Health Insurance as a Self-Employed Entrepreneur with Katherine Phillips, Licensed Insurance Broker
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:
Don’t let fear of failure hold you back; take a chance, even if rejection feels likely.

Dream big and set ambitious goals for your business and personal growth.

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.
43 min
November 01, 2024128. Creating an Impactful Business Network Through Real Connections with Alisha Kumar
Business can be fun and easy! If you don’t think that is true, this episode is definitely for you!

I am joined by Alisha Kumar, a powerhouse entrepreneur and connector. Alisha is the founder of The Social Project, an ads agency focused on e-commerce paid ads and SEO, as well as Here for a Good Time podcast, and The Founders Table, a unique dining experience for entrepreneurs craving deeper, next-level business conversations.

Tune in to hear her inspiring journey from corporate life to building a multi-faceted business empire, her lessons learned from pivoting her business model, and how she brings people together for authentic connections.

In this episode:
Alisha’s Journey to Entrepreneurship

The challenges and rewards of pivoting from a social media agency to an ads-focused agency, and why sometimes less is more when building a team.

The Founders Table: What inspired Alisha to launch this dinner series and how she uses it to foster genuine connections among entrepreneurs.

Community Building & Authentic Networking

Keeping an open mind to new opportunities and people

Action Steps for the week:
Connect with Five New People

Take the Conversation Offline

Unplug and Explore

Connect with Alisha:
Instagram: https://www.instagram.com/alishakumar/
Learn more about The Founders Table and Here for a Good Time Podcast: https://alishakumar.carrd.co/
Learn about Alisha’s Ads Management Services: https://thesocialproject.ca/

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.
37 min
October 24, 2024127. How to Build an Email Community That Converts with Isabelle Sarley
Is building an email list overwhelming you? Discover how to simplify and strategize your email marketing while creating an engaged email community with expert Isabelle Sarley.

In this episode I speak with email marketing expert Isabelle Sarley. Isabelle is an email marketer and copywriter for ambitious personal brands and creatives (who give a frick) and supports them with her 3-step method and nurture-focused strategies so they can increase their open rates, connect more powerfully to their communities, and generate more sales.

By providing done-for-you emails and interactive funnels, she helps her clients gain clarity, feel confident about their email marketing, and grow their businesses sustainably. When Isabelle is not writing emails and optimizing email marketing strategies, you can find her by the lake or going on nature trail walks, daydreaming about Kauai, Hawaii, and playing hide and seek with her sassy cat Newton.

In this episode:
The importance of treating your email list as a community, not just a list of contacts.

How to create interactive email funnels that feel personalized and engaging.

The essential email sequences every entrepreneur needs: welcome, evergreen sales, and re-engagement sequences.

Why consistency is key to nurturing your audience and building trust.

The role of storytelling and strategic subject lines in improving open rates and conversions.

Action Steps for the week:
If you don’t have an email list, start by writing down why you need one and what your audience would gain from being part of it.

Pay attention to everyday stories that can inspire your email content and help you connect with your audience.

Set up a content email template to save time and streamline your email creation process.

Connect with Isabelle:
FREEBIE: https://isabellesarley.myflodesk.com/employeetobosspostlaunch
WEBSITE: https://www.isabellesarley.com/
INSTAGRAM: https://www.instagram.com/isabellesarley

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.
38 min
October 15, 2024126. The Secret to Better Sales: Authenticity and Follow-Up Strategies with Rachel Morgan
Struggling to close sales without feeling pushy?

In this episode I speak with Rachel Morgan, a Retail Sales Coach and Trainer, is passionate about helping retail businesses thrive and achieve their full potential through effective sales strategies and customer engagement. With +13 years of experience in luxury retail, she works with businesses to hear less "I'm just looking" and feel confident to engage without feeling pushy and effectively follow-up. She specializes in turning around underperforming stores and increasing their customer lifetime value.

In this episode:
Rachel’s career shift from fine jewelry sales to launching her own sales training business

The difference between sales coaching and training, and why you need both

How to build genuine connections with your customers and avoid pushy sales tactics

The importance of follow-ups and how they create long-term customer relationships

Tips for crafting open-ended questions that help you learn more about your clients and boost your sales

How to engage customers effectively in retail or online business

Action Steps for the week:
Follow up with 5 people that you have not spoken to in a month.

Look at what the last 5 people bought from you, and see if there was an upsell you could have offered.

Think about your open ended questions

Connect with Rachel:
Instagram: https://www.instagram.com/rachelmorgancoaching
Linkedin: https://www.linkedin.com/in/rachelmorgancoaching/
Website - https://www.rachelmorgancoaching.com
Let's Chat - https://calendly.com/rachelmorgancoaching/connection-call
Newsletter - https://www.rachelmorgancoaching.com/offscript

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.
51 min
October 10, 2024125. How to Build a Thriving Business Partnership with Christina of Heart and Social Media
Starting a business can be overwhelming, but having the right partner can make all the difference. In this episode I sit down with Christina, co-founder of Heart & Social Media, a digital marketing agency.

Christina is the Co-Founder of Heart & Social, a digital marketing agency that works with small businesses to strengthen their brand's digital presence through brand design, social media, and website design. Christina and her business partner Brianna started Heart & Social in March of 2020 and have been helping small businesses and business professionals from across the country grow their brands ever since.

Christina shares her journey from employee to boss and how she and her business partner, Brianna, built a successful company specializing in website design, branding, and social media strategy.

Key Topics Covered:
The importance of complementary skill sets in business partnerships

How Heart & Social was founded and the importance of clear communication

Adjusting business services to match the evolving digital landscape

The role of branding and social media in building a strong online presence

Tips for starting and growing a business with a partner

Action Steps for the week:
Define Your Business Vision & Make a List!

Enhance Communication Skills

Understand Your Strengths

Connect with Christina:
Instagram: https://www.instagram.com/heartandsocialmedia
Pinterest: https://www.pinterest.com/heartandsocialmedia/
Facebook: https://www.facebook.com/heartandsocialmedia

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.
43 min
October 03, 2024124. Mastering Business Operations: How to Scale and Optimize for Success with Rhi Pearce
Are you feeling overwhelmed in your business and struggling to balance it all? Wondering if it’s time to bring in more help but unsure where to start? In this episode, we dive deep into how a COO can streamline your business operations—and your life.

In this episode I sit down with Rhi, a COO who helps business owners simplify their operations and find harmony between business and personal life. Rhi shares her journey from employee to entrepreneur, how she managed to become fully booked within a month of starting her business, and the difference a COO can make in scaling a growing business. She breaks down what a COO actually does, how to know when you need one, and offers practical advice for early-stage business owners.

In this episode:
Rhi’s story of moving from luxury hospitality to becoming a COO and building a fully booked business in her first month.

The importance of planning ahead and building your business before launching.

How a COO can streamline both business operations and personal life for the founder.

Key differences between hiring a COO and a VA, and when to bring in each.

Rhi’s top operational tips for business owners in their first few years.

The importance of visibility into your business operations and systems for long-term success.

Action Steps:
Create a Master List: Write down everything you do in your business—daily, weekly, monthly, quarterly, and yearly.

Analyze the Gaps: Compare this master list against your business vision. Where are the gaps between what you do and what you want to achieve?

Increase Visibility: Implement systems or tools that give you more visibility into your operations, so you can plan ahead and make informed decisions.

Connect with Rhi:
Instagram: https://www.instagram.com/opsbyrhi/
Website: https://rvpalimited.com/

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.
34 min
September 18, 2024123. From $1.6M Business to Burnout and Restarting Again for a Purpose-Driven Life with Fernanda Bertrand
What if you make it to the top of your game but still feel unfulfilled?

This is exactly what happened to this week’s guest, Fernanda Bertrand, a Holistic Business Coach and host of The Highest Self Project podcast. She is a guide for entrepreneur women to connect with their highest purpose and craft a vision to scale their business in alignment with who they truly are and who they are meant to serve in this lifetime.

Fernanda shares her inspiring journey from scaling a multimillion-dollar business to finding her true purpose by helping others connect with their highest self. We discuss the challenges of leaving a successful business to pursue a passion-driven career, the importance of aligning with your purpose, and how to embrace the balance between masculine and feminine energies in business.

In this episode:
Fernanda’s journey from a multimillion-dollar business to starting over with a purpose-driven career

The power of trusting your intuition and taking leaps of faith in business

How to balance masculine and feminine energy for business success

Reassessing your goals and realigning with your highest self

The importance of planting seeds for long-term success and impact

Action Steps:
Reflect on your year going into fall

Let Go of What No Longer Serves You

Plant New Seeds for Growth

Connect with Fernanda:
Podcast: The Highest Self Project

Instagram: @fernanda.bertrand

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.
43 min
September 12, 2024122. The Secrets to Pricing & Growing a Luxury Photography Business with Alena Florie
What does it take to turn your passion into a successful business? In this episode I sit down with Alena Florie, founder of Alina Lauren Photography, to talk about her incredible journey from working traditional photography jobs to creating a luxury brand focused on empowering women.

Alena is a Seattle based, award winning portrait photographer specializing in women's glamour, headshots and boudoir. Her goal is to empower women through fully customized, magazine style portrait experiences.

She shares her experiences with pricing, how she overcame imposter syndrome, and the strategies she’s using to scale her business full-time.

In this episode:
Alina’s transition from employee to boss and the evolution of her photography career

The emotional and transformative experience Alina creates for her clients

Pricing for profitability: How to charge what you're worth

Building confidence in your work and overcoming imposter syndrome

The importance of finding your niche and ideal clients

Alena’s strategies for growing her business and preparing to go full-time

Action Steps:
Figure out your business numbers and expenses

Find a supportive community

Take small steps every day!

Connect with Alena:
Website: alenalauren.com

Instagram: @alenalaurenphoto

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.
38 min
September 06, 2024121. Healing the Entrepreneurial Spirit with Julie Vertzayias
As humans, we experience a lot of emotions and as entrepreneurs, we often need to face these and overcome them to grow.

In this episode, I am speaking with Julie Vertzayias a holistic practitioner focusing on finding fulfilment in self & life through inner child healing, shadow work, human design, reiki energy healing and tarot readings. She loves diving deep into the depths of what holds us back in life by going into the past to fully let it go and heal in order to allow the new desires to come into the present. Her focus with Human Design and spiritual practices allow her to ask the right questions with her clients to overcome obstacles/roadblocks and begin shifting their perspective on life.

We discuss how the journey from employee to boss requires a shift in mindset, and Julie shares her own transformative path. She also shares marketing tips on how she grows her business and invites people to work with her!

Action Steps:
Start a Meditative Practice

Identify patterns in your life that are good or bad.

Spend one day with no plans and see where the universe takes you

Resources Mentioned:
Human Design

Tarot Readings

Reiki Energy Healing

Meditation

Connect with Julie:
Website: juliesunknown.com
Instagram @JuliesUnknown

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.
43 min
August 28, 2024120. Mastering Multiple Business Ventures: Coffee Shops, Coaching, TikTok Fame, and Print on Demand with Multi-Passionate Entrepreneur Ellie Hugdahl
In this episode of the Employee to Boss podcast, I sit down with Ellie Hugdahl, Owner of Unity Coffee Company and Online coach for business owners wanting to improve their marketing, mindset & money. Ellie is a multi-passionate entrepreneur who owns two thriving coffee stands in the Pacific Northwest and has built a strong presence on TikTok, where she shares invaluable business coaching tips for entrepreneurs.

In this episode:
Ellie's Journey: Ellie shares her entrepreneurial journey, starting with her early passion for business, her experience working at a coffee stand at 15, and how she ended up buying that same stand years later.

The Power of Systems: how she’s been able to step away from the day-to-day operations of her coffee stands by setting up strong systems and a reliable team.

The importance of learning through experience, surrounding yourself with the right people, and being willing to take action even when you don’t have all the answers.

TikTok Success: how she built a large following on TikTok by consistently posting valuable content for new entrepreneurs, and how her dedication to providing actionable advice has paid off.

Balancing Multiple Passions: How she manages to juggle multiple business ventures by setting specific goals and staying focused on one project at a time until it’s self-sustaining.

Action Steps:
Set Specific Goals - Set 3 goals for the next quarter!

Get in the Right Rooms and surround yourself with the right people.

Take Action: Stop learning and start doing.

Resources Mentioned:
The Ed Mylett Show: https://www.edmylett.com/podcast

Shopify: https://www.shopify.com

Listen to my episode on Staying Inspired and Productive When No One Is Watching: https://podcasts.apple.com/us/podcast/employee-to-boss-entrepreneurship-side-hustles-and/id1598027167?i=1000658818129

Connect with Ellie:
Instagram: Instagram.com/Ellie.hugdahl
TikTok: https://www.tiktok.com/@ellie.hugdahl?_t=8mJsAFRx6ZK&_r=1
Unity Coffee: https://www.instagram.com/unitycoffee/
Important Links: https://stan.store/EllieHugdahl

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.
35 min

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

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Welcome to the Employee To Boss podcast!

Employee To Boss is for everyone with an entrepreneurial spirit… For those wanting to start their business, for those wanting to go all-in on their…

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

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

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