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

What if the thing you feared most became your greatest asset?

In this episode, I'm chatting with Kathleen, an Online Business Manager and AI consultant who had a complete breakdown when AI emerged—convinced it would end her career. Now? She's the expert helping business owners like us streamline operations and embrace automation.

Kathleen shares her honest journey from corporate burnout to building a thriving business, starting with photography, pivoting to VA work during COVID, and eventually finding her zone of genius in systems and AI consulting.

If you've ever felt overwhelmed by tech tools or unsure where to start with AI, this conversation is your permission slip to start small.

What we cover:

• ​Why Kathleen thought AI would take her job—and how she turned fear into expertise
• ​The truth: AI won't replace you, but not learning it might hold you back
• ​How to start with AI without the overwhelm (one thing at a time)
• ​ChatGPT vs. Claude vs. Kassidy.AI—which to use and when
• ​The most common mistakes people make with AI in business
• ​Essential systems every business needs: lead management, response process, and onboarding
• ​Three actionable steps you can take today

Connect with Kathleen: https://linktr.ee/thevirtualspell

Connect with me, Hayleigh Hayhurst:

Steal my Podcast Launch Checklist for free: http://espressopodcastproduction.com/checklist

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.

If you’ve ever felt like your business is everything—your identity, your time, your mental space—this episode is going to hit home.

In this conversation, I’m joined by Rena Duell, a business coach at One Team Partners, who spent 25 years running her own business before hitting a breaking point that forced her to completely step away.

We talk about what burnout actually looks like (hint: it’s not just being tired), why so many entrepreneurs don’t even realize it’s happening, and what it really takes to rebuild your business in a way that supports your life—not consumes it.

This is one of those episodes that will make you pause and rethink how you’re operating day-to-day.

In this episode, we cover:

What burnout actually looks like (and how it can show up physically)

Why hustle culture feels normal—but isn’t sustainable

How to separate your identity from your business

The role of community when you’re building alone

How to structure your workday around your energy (not just your calendar)

Decision fatigue—and how to stop letting it drain you

The truth behind “having it all” as an entrepreneur

Why you are the ceiling of your business growth

Rena is offering listeners a free month inside her coaching community Big Talk (normally $20/month), plus a free 1:1 coaching call.

Email: [email protected] and mention Employee to Boss to get access.

You can also connect with her on LinkedIn or learn more at OneTeamPartners.com.

Connect with Rena: https://www.linkedin.com/in/rena-duell/

Connect with me, Hayleigh Hayhurst:

Steal my Podcast Launch Checklist for free: ⁠https://www.espressopodcastproduction.com/⁠checklist⁠

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.

Ever wondered how introverts can become powerful speakers and thought leaders? International speaker Stephanie Thoma (250+ events, featured in Forbes) shares her journey from employee to boss and the exact framework she uses with clients to build calm authority.

In This Episode:

• Stephanie's path from tech layoff to qualitative researcher to international speaker
• The 4-part "Connect with Confidence" Framework: Calm → Confidence → Connection → Impact
• Why having ONE signature talk builds more authority than customizing every time
• How to know if you're ready to be a podcast guest vs. host your own show
• Box breathing technique for instant calm before speaking or networking
• The concept of "conversational sponges" for genuine connection
• How Stephanie's book Confident Introvert came from her validated workshop

I met Stephanie through The Entreprenista League, a business and community membership where founders like you can access top-tier resources, media opportunities, and a community that will be there to support you as you grow your business. Join here: https://refer.entreprenista.com/2bvagj2con4u

Connect with Stephanie: https://stephaniethoma.com

Connect with me, Hayleigh Hayhurst:

Steal my Podcast Launch Checklist for free: https://www.espressopodcastproduction.com/checklist

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

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

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

LinkedIn: Hayleigh Hayhurst

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 on Apple Podcasts or Spotify—it truly helps more entrepreneurs find the show!

t's been a while since I've dropped a solo episode here on Employee to Boss! Between managing two podcasts and producing 10 episodes a month, things have been busy—but in the best way. As we close out Q1 and step into Q2, I wanted to pull back the curtain and share what's been happening behind the scenes at Espresso Podcast Production.

This episode is a peek into how quickly things can shift in business—from hiring decisions to launching new ventures and restructuring offers based on what's actually selling. If you've ever wondered what it's like to navigate growth, pivot when needed, and invest in your vision without expecting immediate returns, this conversation is for you.

In this episode:

• The three-month sales cycle and how my Europe trip set me up for Q1 success
• Hiring a new behind-the-scenes team member to support growth without disrupting client experience
• Launching Podcasters NW, a live networking event for podcasters in the Pacific Northwest (and why I'm investing in connection over profit)
• Celebrating one year in Seattle Executive Association and how being "the dumbest person in the room" has fueled my growth
• The surprising success of my one-off strategy sessions (and why they're outselling my core offers right now)
• My evergreen webinar on using your podcast to build your brand in 2026

Free Webinar: How to Use Your Podcast to Build Your Brand in 2026: https://espressopodcastproduction.kit.com/thepodcasteffect

Resources Mentioned:

• Join Podcasters NW (Seattle/PNW area): DM me "EVENT" on Instagram @espressopodcastproduction
• Seattle Executive Association: https://www.seattleexecs.org
• Logo & Branding: Taylor Hanson, Hanson Designs
• Event Planning Support: Whitney Adams-Moore, Electric Butter Marketing

Connect with me, Hayleigh Hayhurst:

Steal my Podcast Launch Checklist for free: https://www.espressopodcastproduction.com/checklist

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

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

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

LinkedIn: Hayleigh Hayhurst

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 on Apple Podcasts or Spotify—it truly helps more entrepreneurs find the show!

What happens when you stop waiting for the “perfect plan”… and just start building?

In this episode, I’m sitting down with Rachel Rowland—real estate agent, founder of Eastside EntreprenueHERs, and someone who completely transformed her life and income in a very short amount of time.

We talk about her transition from teaching during the chaos of 2020 to stepping into entrepreneurship, how she scaled faster than she expected, and what it really takes to build a business rooted in community.

We also get into networking (what actually works vs. what feels… gross), showing up online without overthinking it, and the mindset shifts that changed everything for her.

In this episode:

• The real story behind leaving a stable career to start over
• How mindset can either block or accelerate your growth
• Why most networking feels off—and how to do it differently
• Building a community-first business (and why it works)
• The truth about showing up on social media consistently
• What actually drives business today (hint: it’s not views)
• Real estate myths, market trends, and what buyers should know

Connect with Rachel:

Eastside EntreprenueHERs Instagram: https://www.instagram.com/eastsideentrepreneuhers/

Real Estate Instagram: https://www.instagram.com/rachelrowlandrealestate/

Connect with me, Hayleigh Hayhurst:

Steal my Podcast Launch Checklist for free: ⁠https://www.espressopodcastproduction.com/⁠checklist⁠

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.

Building a business can feel isolating, especially for female founders navigating growth, leadership, and visibility. But it does not have to be that way.

In this episode I sit down with Stephanie Cartin, co-founder of Entreprenista, the largest community of ambitious women founders worldwide. Stephanie shares her journey from Cornell hospitality student to social media agency owner to community builder serving over 3,600 women entrepreneurs.

If you've ever felt isolated in your business journey or wondered how successful founders build lasting connections, this conversation offers a grounded roadmap for growth through community.

The Entreprenista League, a business and community membership where founders like you can access top-tier resources, media opportunities, and a community that will be there to support you as you grow your business. Join here: https://refer.entreprenista.com/2bvagj2con4u

In this episode we cover:

• Stephanie’s transition from Marriott corporate life to co-founding Social Fly

• Why she and her co-founder invested in networking early — even with no budget

• How Entreprenista evolved from a podcast into a global founder community

• Real examples of collaborations that turned into major business opportunities

• How to network authentically without falling into “hustle culture”

• Practical ways founders can use LinkedIn and connection calls to build real relationships

• What it takes to scale a community to thousands of members

Learn more about Entreprenista: https://refer.entreprenista.com/2bvagj2con4u

Connect with Stephanie: https://www.linkedin.com/in/stephjillcartin/

Connect with me, Hayleigh Hayhurst:

Steal my Podcast Launch Checklist for free: ⁠https://www.espressopodcastproduction.com/⁠checklist⁠

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.

If you've ever thought "I want to make my dog famous" or "my cat should be an influencer," this episode is for you. Seriously!

I'm sitting down with Ashley, the owner of Petfluencer Secrets, and we're talking all about how she turned her cat into a full-time business. Her cat Chip the Manx has over 486,000 YouTube subscribers and 122,000 Instagram followers. And before you think this is just a fun hobby, let me be clear: this is a six-figure business. Multiple six figures.

If you've ever wondered how to make money with your pet's Instagram account, how pet influencers get brand deals, or what it actually takes to grow a pet account on TikTok, YouTube, or Instagram, this is your episode.

In this episode:

• Why she started a cat Instagram account while drowning in physical therapy school debt
• The side hustle that changed everything: blogging in the mid-2010s
• How she went from posting cute cat videos to realizing "wait, I can teach this"
• Her transition from full-time physical therapist to part-time to full-time entrepreneur

Connect with Ashley, Chip and

Petfuencer Secrets: https://www.instagram.com/petfluencersecrets/

Chip the Manx: https://www.instagram.com/chipthemanx/

Biskit the Calico: https://www.instagram.com/biskitthecalico/

Connect with me, Hayleigh Hayhurst:

Steal my Podcast Launch Checklist for free: ⁠https://www.espressopodcastproduction.com/⁠checklist⁠

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

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

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

Subscribe to my email newsletter for weekly podcast news and exclusive offers: https://espressopodcastproduction.kit.com/1501c2e46f

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.

Marketing your business doesn't have to feel overwhelming. In this episode, we're diving into sustainable, approachable marketing strategies that actually work for small business owners—without the burnout.

In this episode, you'll learn:

• How to create a marketing strategy that fits your life (not the other way around)
• Why playing to your natural strengths makes all the difference
• The truth about which marketing channels actually convert for small businesses
• How to get comfortable being visible online—even if you hate being on camera
• Why consistency matters more than perfection when it comes to content creation
• How to shift from inspiration-driven marketing to sustainable systems

About Prassède:

Prassède is the founder of Numinous Creative, a marketing agency that helps CEOs and small business owners build realistic marketing strategies that get results. After being fired from her project management job eight years ago, she discovered her passion for helping entrepreneurs get out of the "default marketing position" and create systems that work without constant manual effort. With a background in conflict resolution and a love for creative storytelling, Prassède specializes in social media, email marketing, and blog strategies that are both high-level and approachable.

Connect with Prassede: https://www.instagram.com/numinous.creative/

Connect with me, Hayleigh Hayhurst:

Steal my Podcast Launch Checklist for free: ⁠https://www.espressopodcastproduction.com/⁠checklist⁠

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

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

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

Subscribe to my email newsletter for weekly podcast news and exclusive offers: https://espressopodcastproduction.kit.com/1501c2e46f

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.

What if saying "no" could actually strengthen your relationships—and your business?

In this episode, Hayleigh sits down with Dr. Jen Fry—former college volleyball coach turned professional speaker, PhD, and tech entrepreneur—to discuss the art of setting boundaries, navigating conflict, and building a business with backbone.

Jen shares her journey from coaching for 15 years to becoming a sought-after speaker on conflict and culture, launching a tech startup (Cordal), and writing her book I Said No: How to Have a Backbone and Boundaries Without Being a Jerk.

In this conversation, you'll discover:

• Why people-pleasing is actually being unreliable
• How to practice "micro advocacy" to build your no muscle
• The real cost of resentment in business decisions
• Why validation of your idea doesn't guarantee revenue
• The humbling truth about starting a tech company
• How to know when you "hate it enough" to make the leap

Whether you're struggling to set boundaries with clients, contemplating your next business pivot, or just need permission to stop people-pleasing, this episode will leave you feeling empowered to advocate for yourself—without the guilt.

About Jen Fry:

Dr. Jen Fry is a professional speaker, author, PhD in sport geography, and founder of Cordal, a group travel coordination tech platform. After 15 years as a college volleyball coach, Jen pivoted to professional speaking in 2019, focusing on conflict navigation and cultural transformation. Her book I Said No: How to Have a Backbone and Boundaries Without Being a Jerk is available now. Jen is known for her direct, compassionate approach to helping people—especially women—advocate for themselves fearlessly.

Connect with Jen:

• Website: JenFryTalks.com
• Book: I Said No (available on her website with stickers and swag, or on Amazon/Barnes & Noble)
• Social Media: @JenFryTalks on all platforms

3 Action Steps from This Episode:

1. Know your relationships are worth conflict. Conflict shows us the depth of our relationships—avoiding it keeps you surface-level.

2. Your first "no" is the easiest. When you say no to someone, prepare for others to try to change your mind. Have a plan and hold your boundary.

3. You're always healed until you go home. Practice leaving situations where people make you uncomfortable—you don't owe anyone your presence when they're unkind.

Connect with me, Hayleigh Hayhurst:

Steal my Podcast Launch Checklist for free: ⁠https://www.espressopodcastproduction.com/⁠checklist⁠

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

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

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

Music: John Kiernan. www.johnkiernanmusic.com

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

Sign up to be on my email newsletter for weekly podcast tips, tricks and exclusive offers: https://espressopodcastproduction.kit.com/1501c2e46f

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.

Building a business gets easier when you stop winging it and start leading with a plan.

I sit down with Shellee Howard, CEO of College Ready and CR Future Now and host of Parents: Is Your Teen College Ready to talk about what it really looks like to go from employee to boss when you’ve got an entrepreneurial mindset and a deep desire to make an impact.

You’ll hear how College Ready began when her son came home with a clear college and career goal, and how that sparked a process that helped him earn major scholarship offers and graduate without debt. Shellee breaks down what she believes every entrepreneur needs: a clear why, a business plan, and accountability that gets your goals out of your head and onto paper.

This episode also gets practical about visibility. Shellee shares why she resisted being the face of her brand, what shifted when she decided to tell her story, and how hiring mentors helped her grow into bigger opportunities, without chasing them.

In this episode, you’ll discover:

• Why corporate experience can set you up for future entrepreneurial success
• How solving real problems can lead you into your best business idea
• What a business plan protects you from when motivation isn’t enough
• Why sharing your story matters when you want bigger opportunities
• Three action steps to start a podcast with clarity and momentum

Connect with Shellee:

Complementary 30-minute meeting and checklist for success: www.collegereadyplan.info

Website: www.collegereadyplan.com

Teens find their passion and their purpose: www.empowereducation.world

Facebook: http://www.facebook.com/shellee.howard1

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

LinkedIn: https://www.linkedin.com/in/shelleehoward/

Connect with me, Hayleigh Hayhurst:

Steal my Podcast Launch Checklist for free: ⁠https://www.espressopodcastproduction.com/⁠checklist⁠

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

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

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

Music: John Kiernan. www.johnkiernanmusic.com

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

Sign up to be on my email newsletter for weekly podcast tips, tricks and exclusive offers: https://espressopodcastproduction.kit.com/1501c2e46f

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.