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

Hayleigh Hayhurst, Podcast Producer & Strategist
  • 5.0 (39)
  • 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

    178. Networking Without the Transactional Vibe with Emily Shimwell: Why Human Connection Still Matters

    What if the best business opportunities aren’t found online, but across a dinner table? In this episode, I sit down with Emily Shimwell, founder of Dine Wilder and The Room, to talk about the power of creating spaces where people feel genuinely connected. From starting her first business with a 10-week-old baby to building a community around long-table dinners, events, and women in business, Emily shares how following her intuition and creating meaningful human connection has shaped her entrepreneurial journey. We dive into why the best networking doesn't feel transactional, how to create events where different personality types can actually feel comfortable, and why sometimes the biggest business opportunities come from simply putting yourself in the room. Emily also shares her approach to trusting your intuition, taking action before you have the full plan, and building a community that extends far beyond a single conversation. Attend Feast on October 25, 2026 in Squamish: https://dinewilderevents.com/feast-2026 Connect with Emily: Instagram: https://www.instagram.com/_emily_wilder_/ Website: https://dinewilderevents.com/ Dine Wilder: https://www.instagram.com/dine.wilder/ 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 ⁠ 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.

  2. Sep 22

    177. How to Talk About Grief and Loss: Psychic Medium Colleen Coleman on Mediumship, Death & Building Community

    What if everything you've been taught about "moving on" from grief is wrong?In this episode, I sit down with Colleen Coleman — founder and CEO of Celebration of Life Studios, professional psychic medium, trained end-of-life doula, and graduate student of thanatology — for a conversation about grief, loss, and mediumship, and why so much of what we've been taught about "healthy grief" doesn't hold up. Colleen shares her own journey from losing her father to building a public benefit company changing the conversation around death, dying, and bereavement in Seattle and beyond.Learn more about Celebration of Life Seattle: https://celebrationoflifeseattle.com 🎁 Giveaway: Colleen is giving away 2 free tickets to this event. Head to my Instagram to enter! https://www.instagram.com/espressopodcastproduction/ Connect with Colleen: Instagram: https://www.instagram.com/colleencolemanmedium/ Enter the giveaway + event tickets: https://www.celebrationoflifeseattle.com Email: colleen@colleencoleman.com 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 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.

  3. Sep 15

    176. Networking Without the "Ick" with Megan Gillespie: How to Build a Business People Remember

    If networking makes you cringe, this conversation will completely change the way you think about it. In this episode, I sit down with visibility mentor, podcast host, and Olympia Boss Society founder Megan Gillespie to talk about what it really means to be seen in business. From managing corporate salons at 21 to building a thriving community for women entrepreneurs, Megan shares how every career pivot led her to one powerful realization: community is the foundation of sustainable business growth. We dive into why networking doesn't have to feel transactional, how local business owners should think differently about marketing, and why showing up authentically will always outperform trying to appear perfect. Free Resource Megan's free Networking Without the "Ick" Guide helps entrepreneurs build meaningful business relationships without feeling salesy or transactional. If networking has ever felt uncomfortable, this guide offers practical strategies to help you connect with confidence. https://megangillespie.myflodesk.com/networkingwithouttheick?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAcGRvZgJleHRuA2FlbQIxMQBzcnRjBmFwcF9pZA85MzY2MTk3NDMzOTI0NTkAAac61n6V4PamdcDt1ZEob9haCy4NFjIa2WmYl_b57tyk4zxQN01ikfloE53vZQ_aem_w-5ZuIFW8p_uaFUtUWt4Kw Connect with Megan: Website: https://olympiabosssociety.com/ Instagram: https://www.instagram.com/olympiabosssociety/?utm_source=chatgpt.com Personal Instagram: https://www.instagram.com/themegangillespie/?utm_source=chatgpt.com 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 ⁠ 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.

  4. Sep 8

    175. Stop Forcing Growth: Build a Business That Works With You with Jen Dean

    Every business has seasons. The key isn't pushing harder, it's knowing which season you're in. In this episode, I sit down with leadership strategist, CEO of the Mercer Island Chamber of Commerce, and founder of A&E Collective, Jen Dean, to talk about what it really means to lead with clarity, navigate the different seasons of business, and stop forcing strategies that aren't working. Jen shares her unexpected journey from interviewing for an assistant role to becoming CEO, how she built a thriving Chamber community, and why she launched A&E Collective to help leaders gain clarity through alignment and perspective. We also dive into networking, leadership, hiring, business growth, and why the right relationships can change the trajectory of your business. Connect with Jen: Instagram: https://www.instagram.com/jenniferdean07/ A&E Instagram: https://www.instagram.com/aandecollective/ Mercer Island Chamber of Commerce: https://www.instagram.com/mercerislandchamber/ 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 ⁠ 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.

  5. Aug 18

    174. What Makes a Great Business Coach? Building Trust, Systems & Results | Malcolm Reid Jr.

    Anyone can call themselves a coach, but what actually makes someone worth hiring? In this episode, I sit down with entrepreneur, business strategist, and Profit Advisor founder Malcolm Reid Jr. to unpack the trust crisis in the coaching industry. After building multiple seven-figure businesses and helping business owners uncover hidden revenue opportunities, Malcolm shares what truly separates great coaches from everyone else. We dive into why trust has become the biggest currency in business, the systems every coach needs to scale sustainably, how AI is changing the industry, and why getting results, not going viral, is the foundation of long-term success. Free Resource Malcolm is giving listeners a free copy of his book, Massive Action, where he shares 22 no- and low-cost strategies to uncover hidden revenue opportunities, increase profitability, and grow your business without relying on expensive marketing tactics. Download your free copy at: 100KLeak.com Connect with Malcolm: https://proglobalba.com/ https://www.linkedin.com/in/proglobalexpert/ 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 ⁠ 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.

  6. Jul 28

    173. How Travel Can Make You a Better Entrepreneur with Chericka Johnson, Love + Leisure

    What if entrepreneurship could give you the freedom to explore the world... while helping others create unforgettable experiences? In this episode, I sit down with travel advisor, entrepreneur, and founder of Love & Leisure Travel, Chericka, to talk about her journey from climbing the corporate ladder to building a business centered around purpose, travel, and meaningful connection. We dive into what it really takes to build a successful travel business, why rest fuels creativity, the power of niching down, and how relationships—not algorithms—continue to shape incredible client experiences. Chericka also shares her passion for helping people create lifelong memories through travel, the lessons she's learned from entrepreneurship, and why community is more important now than ever. Wha:t You'll Learn Why travel is one of the best investments you can make. Chericka shares how exploring new places expands your perspective, fuels creativity, and creates memories that last far longer than material possessions. The truth about building a travel business. Behind the beautiful destinations is a business built on expertise, systems, relationships, and years of industry knowledge—not simply booking vacations online. How niching down creates bigger opportunities. Rather than trying to serve everyone, Chericka explains why specializing in destination weddings, group travel, and romance travel has helped her stand out in a competitive industry. Why relationships still matter in an AI world. AI can be an incredible tool, but nothing replaces having an experienced advisor who knows the destinations, has trusted industry connections, and can advocate for you when things don't go according to plan. The entrepreneurial lesson every business owner needs to hear. From creating repeatable systems to prioritizing client experience and referrals, Chericka shares the foundational habits that help businesses grow sustainably. Why rest isn't a luxury—it's part of your strategy. Entrepreneurship often glorifies hustle, but Chericka explains why creating space to slow down, reflect, and recharge ultimately leads to greater creativity, better leadership, and a stronger business. Connect with Chericka: Instagram: https://www.instagram.com/loveandleisuretravel/ Website: https://www.loveleisuretravel.com/ 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 ⁠ 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.

  7. Jul 14

    172. How Molly Nutt Built, Scaled & Sold a Successful Agency

    Have you ever wondered if you're building a business that actually gives you more freedom... or just another full-time job? In this episode, I sit down with agency owner, entrepreneur, and mentor Molly Nutt to talk about what it really takes to build a scalable business. From growing an agency and hiring a team to selling a successful business, Molly shares the lessons she learned about leadership, delegation, systems, profitability, and why understanding your numbers matters more than chasing growth. We also dive into how AI is changing entrepreneurship, the biggest hiring mistakes business owners make, and how to know when it's actually time to scale. What You'll Learn: Why freedom doesn't automatically come with entrepreneurship. Molly shares the reality of going from corporate life to freelancing—and why building a business without systems can leave you working more than ever. The hiring mindset that saves businesses from costly mistakes. Learn why hiring from "overflow" instead of desperation creates stronger teams, healthier finances, and sustainable growth. How to build a business that's valuable beyond you. From reducing founder dependency to creating repeatable systems, Molly explains what made her agency sellable—and what every service provider should be thinking about early on. Why knowing your numbers changes every business decision. Growth without understanding profit margins, expenses, and cash flow can quickly become dangerous. Molly shares the financial metrics every entrepreneur should be tracking. How AI is making entrepreneurship more accessible than ever. Instead of replacing business owners, AI can become the mentor, operations assistant, and problem-solving partner that helps you move faster and make smarter decisions. Want help hiring your first team member? Molly has created a free Hiring Starter Pack filled with templates, AI prompts, job posting examples, offer letters, and practical guidance to help you confidently make your first hire. If you're preparing to grow your business and build a team, this is the perfect place to start. Connect with Molly: Website: https://acorndigitalstrategynw.com/ Instagram: https://www.instagram.com/molly.nutt/ Connect with me, Hayleigh Hayhurst: Apply to work with us: 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 ⁠ 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.

  8. Jul 7

    171. Cycle Syncing for Entrepreneurs: Work With Your Body, Not Against It | Carly Schade

    Maybe the reason you've been feeling exhausted, overwhelmed, or "off" isn't because you're doing something wrong, but because you've been following advice that was never designed for your body? In this episode, I sit down with wellness coach and registered dietitian Carly Schade to talk about cycle syncing beyond the social media trends. We unpack how understanding your menstrual cycle can help you build a business, manage your energy, improve your health, and reconnect with your intuition. Carly shares how burnout led her to leave her dream job, why she believes women have been taught to ignore their biology, and the simple shifts that can completely change the way you approach work and wellness. What You'll Learn: Why burnout can become your greatest turning point. Carly shares how walking away from her corporate career led her back to her true passion—and ultimately the business she was meant to build. What cycle syncing actually means (and what most people get wrong). Forget rigid rules and complicated tracking. Carly explains her practical approach that's rooted in listening to your body instead of following someone else's formula. How to use your cycle to work smarter in business. Learn how different phases of your cycle can influence creativity, communication, planning, decision-making, and energy—and how scheduling around them can reduce burnout. The missing piece most women never track. Recording your cycle is only half the equation. Carly explains why paying attention to how you feel each day unlocks the patterns that can transform your health and productivity. How trusting your body builds confidence in business. The conversation goes beyond hormones into intuition, decision-making, and why learning to trust yourself may be one of the greatest entrepreneurial skills you can develop. Want to learn more about cycle syncing? Carly's group program, In Sync, is designed to help women better understand their hormones, align their health with their menstrual cycle, and work with their bodies instead of against them. Through education, practical tools, and personalized guidance, you'll learn how to support your energy, nutrition, workouts, and lifestyle in a way that feels sustainable. https://carlyschade.kit.com/products/in-sync?promo=EARLYBIRD Connect with Carly: Instagram: https://www.instagram.com/carlyschade/ Podcast: https://open.spotify.com/show/51sHtEKrYGucKdwfOfRoC4?si=d92ec468dfbe4fb9 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 ⁠ 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.

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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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