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

Hayleigh Hayhurst, Podcast Producer & Strategist
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  • ENTREPRENEURSHIP
  • UPDATED BIWEEKLY

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 side hustle, for those wanting to start a side hustle… and for those who are business curious! Join podcast producer Hayleigh Hayhurst as she guides you through all things business. She is joined by guests from all different industries, at all different points of business to share their experiences, tips, and advice. To have a successful business, you need to know a thing or two about different industries. The reason behind this? It is called info-sponging aka learning and absorbing new information about different industries. Starting a business can be very lonely, and confusing! Each episode will end with three actionable tips for you to follow to get started with your business today! Presented by Espresso Podcast Production, a full-service podcast production company specializing in editing, marketing, and strategy. Grab your coffee and join us!

  1. 5D AGO

    160. How to Say No Without Being a Jerk: Conflict, Culture & Building a Backbone with Dr. Jen Fry

    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 unreliableHow to practice "micro advocacy" to build your no muscleThe real cost of resentment in business decisionsWhy validation of your idea doesn't guarantee revenueThe humbling truth about starting a tech companyHow to know when you "hate it enough" to make the leapWhether 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.comBook: I Said No (available on her website with stickers and swag, or on Amazon/Barnes & Noble)Social Media: @JenFryTalks on all platforms3 Action Steps from This Episode: Know your relationships are worth conflict. Conflict shows us the depth of our relationships—avoiding it keeps you surface-level. 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. 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/ 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

  2. JAN 28

    159. Why a Business Plan Beats a Good Idea Every Time with Shellee Howard

    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 successHow solving real problems can lead you into your best business ideaWhat a business plan protects you from when motivation isn’t enoughWhy sharing your story matters when you want bigger opportunitiesThree 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/ 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

  3. JAN 20

    158. How to Build a Business That Doesn’t Rely on You with Gina Cotner

    What if the thing keeping you “busy” isn’t actually your workload… but your grip on control? In today’s episode, Gina Cotner breaks down what it really takes to shift from doing everything yourself to building a business that can run without you. Gina is the founder of Athena Executive Services, a virtual executive assistant agency built for busy, successful business owners who need high-level support without hiring a full-time 40-hour/week assistant. We talk through her long road from corporate to entrepreneurship, back to employment, and finally to building a true agency—with a team of around 20 and a million-dollar year. If you’re a business owner who knows you should delegate but feels stuck in the “it’s faster if I do it myself” loop, this conversation will give you a new way to think about control, feedback, and the real job of being the boss.  In this episode: why delegation is an investment in who you want to be six months from nowhow to stop building a business that relies on your personality to sellthe “Maui invoices” moment that pushes most owners to finally let gowhy turning tasks over forces you to clean up your processeshow to “inspect, not just expect” without micromanagingwhat it means to give feedback on performance without making it personalthe mindset shift from employee to CEO when there is no manualwhy leaders aren’t paid to do tasks—they’re paid to thinkhow a business can evolve into something that runs with you working 10 hours a weekwhy you can’t wait to feel inspired to take action Connect with Gina: Website: https://www.athenaexecutiveservices.com/ Instagram: https://www.instagram.com/athena_executive_services/ LinkedIn: https://www.linkedin.com/in/athenaea/ Books mentioned: Cashflow Quadrant by Robert Kiyosaki 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/ 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

  4. JAN 13

    157. The Efficiency Circle: Turning Relationships Into Revenue with Faith Morris

    What if building your business wasn’t about doing more, but about being more intentional with the people already around you? In this episode of Employee to Boss, I’m joined by Faith Morris, an operations strategist and community builder who helps entrepreneurs scale sustainably by rethinking how they build teams, partnerships, and networks. We talk about her journey from employee to boss, rebuilding confidence after career rejection, and why intentional relationships, not more platforms, are often the missing piece in business growth. In this episode: why relationships are a form of business infrastructure how rejection can become a catalyst for entrepreneurship what it really means to build community intentionally why consistency beats visibility every time how to turn connections into long-term strategic partnerships the difference between networking more and networking smarter why personal brand matters even if you didn’t plan on building one how to avoid burnout by simplifying where and how you show up Connect with Faith: Efficiency Circle waitlist: https://faith-morris.myflodesk.com/kkbzlmb2e2 Follow Faith on Threads and Instagram: https://www.instagram.com/remote.ops.partner/ LinkedIn: https://www.linkedin.com/in/faithelizabethmorris/ 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/ 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.

    40 min

  5. JAN 6

    156. How Curiosity Turned Into a Global PR Business with Liz Galloway

    Curiosity can be a business strategy when you know how to use it. In this episode I sit down with Liz Galloway, a media and PR expert whose career spans wellness, luxury travel, global events, and broadcasting. Liz shares how her non-linear path from training in high-end wellness spaces overseas to running large-scale media projects became the foundation for a portfolio career rooted in storytelling and relationships. The conversation also dives into organizing TEDx Belltown Women, what makes a pitch stand out, and why most people miss opportunities by not tailoring their story. If you’ve ever felt overwhelmed by PR, pitching, or visibility, this episode gives you a grounded, actionable starting point. This episode is for business owners, creatives, and entrepreneurs who want to grow their authority, collaborate strategically, and stop overthinking their next move. In this episode: Curiosity and skill-stacking can create a powerful portfolio careerStrong storytelling starts with listening, not talkingPodcast interviews are one of the best entry points into PRShort, customized pitches outperform mass outreachVisibility works best when rooted in relationships and strategy  Connect with Liz: LinkedIn: https://www.linkedin.com/in/lizgalloway/ Website: https://brandsanitymedia.co Connect with me, Hayleigh Hayhurst: Apply to work with us: https://hello.dubsado.com/public/form/view/6521a4cc8fdeed003a859a44 Steal my Podcast Launch Checklist for free: https://www.espressopodcastproduction.com/checklist Website: https://www.espressopodcastproduction.com/ Instagram: https://www.instagram.com/espressopodcastproduction/ YouTube: https://www.youtube.com/@EspressoPodcastProduction My favorite podcast tool, Descript: https://www.descript.com/?lmref=KkInCQ Produced by Espresso Podcast Production: https://www.espressopodcastproduction.com

    40 min

  6. 12/09/2025

    155. When the Grind Stops Working: Spotting Burnout as a Business Owner with Arika Allen

    What if the “hustle” you’re proud of is actually burning you out? In this conversation, we’re unpacking what entrepreneurial burnout really looks like—and how to build a business that doesn’t cost you your health, relationships, or sanity. Arika is a leadership coach and former corporate leader who helps high-achieving professionals and founders spot burnout early and reset in sustainable ways. In this episode, we talk about why so many entrepreneurs normalize exhaustion as “just a season,” the beliefs that quietly fuel burnout (even when you love your work), and simple, doable ways to protect your energy—especially as you reflect on this past year and plan for 2026 and beyond. Key Takeaways what burnout actually is for entrepreneurs (beyond just feeling tired) the subtle mindset traps that keep you saying yes when you’re already at capacity how to tell the difference between normal stress and a brewing burnout crash simple daily reset practices to manage your energy (not just your time) Connect with Arika: https://www.arika-allen.com Connect with me, Hayleigh Hayhurst:Steal my Podcast Launch Checklist for free: ⁠https://www.espressopodcastproduction.com/⁠checklist⁠Website: https://www.espressopodcastproduction.com/YouTube: https://www.youtube.com/@EspressoPodcastProductionInstagram: https://www.instagram.com/espressopodcastproduction/Music: John Kiernan. www.johnkiernanmusic.comProduced 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.

    29 min

  7. 11/25/2025

    154. Should You Write a Book for Your Business? A Self-Publishing Deep Dive with Katrina Sawa

    What if your next “big business move” isn’t a new offer or a rebrand… but a book with your name on the cover? In this episode, we’re breaking down how to finally get that book idea out of your head and into the hands of your future clients. Katrina Sawa is a business and marketing coach turned self-publishing expert who has written or contributed to 22+ books and helps entrepreneurs use books as real business assets—not just vanity projects. We talk about how to decide what your first book should be about, the difference between a story book and a system book, why compilation books can be a smart first step, and how to think about ROI so you’re not writing a book instead of paying your bills. If “write a book” is on your vision board, this episode will help you move from dreaming to actually doing. In this episode: why knowing why you want to write a book matters more than having the “perfect” idea the difference between a story driven book and a system based book how to treat your book like a business asset and lead generator, not just a product why compilation books can be a low lift way to become a published author real talk on costs, timelines, and when it’s not the right time to write a book how to use AI ethically for brainstorming without letting it write your whole book Connect with Katrina: https://jumpstartpublishing.net Connect with me, Hayleigh Hayhurst:Steal my Podcast Launch Checklist for free: ⁠https://www.espressopodcastproduction.com/⁠checklist⁠Website: https://www.espressopodcastproduction.com/YouTube: https://www.youtube.com/@EspressoPodcastProductionInstagram: https://www.instagram.com/espressopodcastproduction/Music: John Kiernan. www.johnkiernanmusic.comProduced 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.

    33 min

  8. 11/11/2025

    153. Laughter Yoga & EFT for Entrepreneurs: Stress Less, Show Up More with Toni Fielder

    What if you could lower stress, boost creativity, and show up for your business—just by laughing on purpose? In this episode, we explore Laughter Yoga and EFT tapping as practical tools to move through fear, visibility blocks, and burnout. Today I’m joined by Toni, the founder of Your Smiling Soul, a Laughter Yoga leader and certified EFT (Emotional Freedom Technique) practitioner. We talk about his journey from software consultant to “joy maker,” how surviving cancer reshaped his life’s work, and why adults need play more than ever. You’ll hear a quick Laughter Yoga demo (yes, we laugh together!) and a simple EFT sequence you can use to breathe deeper, calm your nervous system, and finally take action in your business.    Key Takeaways “fake” laughter becomes real fast thanks to mirror neuronswhy Laughter Yoga is breathwork + play, not posesbenefits entrepreneurs notice first: lower cortisol, better focus, easier visibilityEFT tapping to rewire fear loops around pricing, video, and podcastinghow to stack joyful micro-habits (1-minute laugh timers, desk toys, playful breaks)a 5-minute laughter break ≈ a 20-minute regular break for productivitythe four elements of joy Tony teaches: singing, dancing, playing, laughingthree action steps: smile before you open your eyes, skip a few steps to spark joy, laugh for world peace for one minute  Connect with Toni: https://yoursmilingsoul.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/  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.

    50 min
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About

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 side hustle, for those wanting to start a side hustle… and for those who are business curious! Join podcast producer Hayleigh Hayhurst as she guides you through all things business. She is joined by guests from all different industries, at all different points of business to share their experiences, tips, and advice. To have a successful business, you need to know a thing or two about different industries. The reason behind this? It is called info-sponging aka learning and absorbing new information about different industries. Starting a business can be very lonely, and confusing! Each episode will end with three actionable tips for you to follow to get started with your business today! Presented by Espresso Podcast Production, a full-service podcast production company specializing in editing, marketing, and strategy. Grab your coffee and join us!

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