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

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.

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: [email protected]

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.

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.

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.

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.

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.

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.

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.

How do you optimize your Instagram for sales in 2026 without sounding like everyone else?

I sat down with Daria, founder of a personal branding and sales agency, to talk about what's actually working on social media right now. Daria moved from Russia to Canada, spent years battling imposter syndrome before she ever posted consistently, and now helps service providers and founders launch and sell digital offers in 90 days.

We went deep on brand positioning, why "dumbing it down" is the smartest thing you can do, and the real timeline for seeing results from your content.

What You'll Learn

Why your Instagram bio might be costing you clients. Daria breaks down the exact elements your profile needs — clear positioning within seven seconds, optimized highlights, and pinned posts that build authority before anyone even DMs you.

The brand positioning mistake almost everyone makes. Trying to fit your full personality into a two-sentence bio doesn't work. Daria explains why simple, specific language beats clever or "empowering" language every time.

Sell the result, not the process. I loved this reframe — nobody wants to hear about your weekly call structure. They want to know what their life looks like after working with you.

The three-to-six month rule. Daria and I both share why content takes months to convert, why you'll rarely see the moment it actually worked, and why consistency matters more than instant feedback.

Building an email list regardless of follower count. Why your list might be your most underrated business asset, no matter where you're starting from.

Connect with Daria: https://www.instagram.com/dariaast/

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.

You're ambitious, you're building something incredible, and you're working all day every day to make it happen. But what about love? What about creating space for a partner while still showing up powerfully in your business?

Women's dating and relationship expert Natalia returns to Employee to Boss to share how ambitious women can balance masculine energy in business with feminine energy in relationships—and why understanding both is the key to having it all. With all of her current clients now in relationships after leaving dating apps, and three recent engagements, Natalia's approach is clearly working. This conversation will challenge what you think you know about success, love, and what it means to be a powerful woman who also wants partnership.

In This Episode:

• Why all of Natalia's current clients have left dating apps and are now in relationships—and what that teaches us about transformation
• The real qualifications needed to be a love coach (hint: it's way more than just getting married yourself)
• Why you have BOTH masculine and feminine energy—and how to use each strategically in business vs. relationships
• Why only 10% of women doing the work can change the entire paradigm of relationships
• Why your beliefs become your reality—and how to cultivate the ones that serve your vision

Listen to ep 50 with Natalia: https://podcasts.apple.com/us/podcast/employee-to-boss-entrepreneurship-side-hustles-and/id1598027167?i=1000587222147

Connect with Natalia: https://www.instagram.com/nataliaheartcoaching/

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.