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

This week on Employee to Boss, I’m joined by Brandilyn Hallcroft, a powerhouse creative with 25+ years of experience in marketing, branding, and design. She’s the founder of Metro Designs, Metro Events, the creator behind digital shops on Etsy and Zazzle, and the heart behind Journals to Healing—a CBT-based journal collection for personal growth.

In this episode, Brandilyn shares her journey from working in early internet billing tech (yes—before Amazon!) to launching a portfolio of purpose-driven creative businesses. We talk about how she stays organized, overcomes setbacks, and leads with intention in both branding and life.

You’ll learn:

• Why she calls herself “professionally unemployed”—and how gig work changed her life

• How she uses the psychology of design to create emotional brand connection

• The difference between ethical and fear-based marketing (and why it matters)

• Why your mindset is your strongest business tool

• How her journals help people rewire their thinking to reduce anxiety and increase joy

Whether you’re a designer, a multi-passionate entrepreneur, or just trying to find your path—this conversation is filled with practical insights and refreshing honesty.

Brandilyn’s Action Steps for Listeners:

1. Write it down – Your goals, your passions, your ideas. Get it out of your head and onto paper.

2. Watch your mindset – Your thoughts shape your experience. Avoid spiraling into “the sky is falling” thinking.

3. Learn to spot manipulation – Once you understand it, you’ll never unsee it—and you’ll protect your peace and power.

Connect with Brandilyn:

Metro Designs – MetroDesigns.com

Metro Events – MetroEvents.com

Journals to Healing – JournalsToHealing.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/

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.

What if you stopped waiting for the perfect time and just gave yourself permission to go for it—to pivot, to be seen, and to build a business that actually fits your life? In this episode, I chat with Kieryn Wang, founder of AlmostConsulting, about evolving in both business and life.

We talk about building a career in unconventional industries (cannabis, sex tech & alcohol)and learning to stop following the rules that no one actually wrote. Kieryn shares how networking, travel, and community helped reignite her spark—and why letting yourself play in business might be the smartest thing you can do.

If you’ve ever felt stuck, unsure about your next step, or afraid to pivot—this one’s for you.

In this episode:

• Saying yes to unexpected opportunities (even when they’re unconventional)
• What happens when your business no longer fits your life
• How to reignite your creativity when you’ve been coasting
• Letting go of perfectionism and allowing space for play
• The power of community, coaching, and doing the inner work
• Why you don’t need anyone’s permission—but here’s some if you need it anyway

Action Steps:

1. Visualize Your Ideal Day: Start with your dream daily routine—what do you want life to feel like?
2. Explore Possibilities: Look at how others live and work. Get inspired by people doing things differently.
3. Give Yourself Permission: Write it down, say it out loud, believe it: You’re allowed to pivot, evolve, and create the business and life you truly want.

Connect with Kieryn:

Website: https://www.almostconsulting.com

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

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.

You know those conversations where you're like, “Wait—why isn’t everyone talking about this?” That’s exactly how I felt talking to Mike Shu.Mike is the founder of a super successful SEO agency, a digital nomad, and someone who’s mastered the art of direct response marketing (aka what actually moves the needle in business). And get this—he doesn’t even think most businesses under $1M/year should be doing SEO.

In this episode, we talk about:

• How Mike went from burnout and cold calls to building an agency he loves
• The difference between brand marketing vs. direct response (and when to use each)
• The secret to making SEO actually work in today’s AI-driven world
• Why your offer matters way more than your Instagram content
• The rookie mistakes most entrepreneurs make (he made them too)

 Action Steps:

1. Study the psychology behind buying decisions (start with Dan Kennedy).
2. Don’t obsess over going viral—focus on messaging that speaks to your ideal client’s pain points.
3. Build a product so good your clients do the marketing for you.

If you’re building your brand, selling online, or wondering how to scale smarter—this episode is for you.

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.

What do you do when the corporate ladder leaves you feeling unfulfilled—but you’re still craving structure, stability, and impact? For Carol, that answer was stepping away from a high-level advertising career, starting a jewelry brand born out of personal grief, and ultimately buying a successful subscription box business that now fuels thousands of women every month.

In this episode, Carol shares her winding path to owning Sparkle Hustle Grow, a subscription box and membership community for female entrepreneurs. We talk about the real story behind buying a business (spoiler: it’s not as glamorous as Instagram makes it seem), the role personal development plays in business success, and how masterminding and community support can help you grow faster than any online course.

Carol’s Action Steps for the Week:

1. Write down your dream life—what do you really want?

2. Choose 1–2 things from that dream to work toward in the next 6 months.

3. Break down one of those goals into 3 clear, actionable steps you can take this week.

Connect with Carol:

Website: https://www.sparklehustlegrow.com/

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

Join the membership: https://sparklehustlegrow.vipmembervault.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/

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.

What does it take to grow a fitness business that stands the test of time? In this episode we are joined by Laura Mak Quist — a veteran in the wellness and fitness industry with over 30 years of experience coaching women through strength training, yoga, nutrition, and life transitions.

From training athletes and TV personalities to launching a fitness clothing line and now running an online studio, Laura shares how she's continued to evolve her business to match her life stages — from competing in professional fitness to becoming a mom in her 40s. This episode is packed with advice for aspiring fitness coaches, service-based entrepreneurs, and anyone interested in building a business with staying power.

In this episode:

• How Laura transitioned from gym employee to business owner
• What it takes to niche down and stand out in the crowded fitness space
• Why pivoting is the secret to long-term business success
• Her honest take on motherhood, Hashimoto’s, and the wellness industry
• The power of intuition, adaptability, and listening to your audience
• Why movement, strength, and mobility matter for business owners too

 Action Steps:

1. Add more movement into your day — even just 10 extra minutes of walking.
2. Strength train regularly to maintain muscle and support longevity.
3. Incorporate mobility into your routine through yoga or stretching.

Connect with Laura:

Website: https://www.lauramakfitlife.com

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

Online Studio: theyogafitlife.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/

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.

What does it take to turn a niche skill into a thriving local business? In this episode I sit down with Timothy Abadilla, founder of Masterpiece Chess Academy in Los Angeles, to talk about how he went from Uber driver and preschool assistant to running one of the most active chess programs in Southern California. And spoiler alert — it’s not just about loving chess.

Tim shares his full journey from employee to boss, the creative ways he attracted his first clients (hint: Pokémon was involved), and how his strategic thinking from chess carries over into how he grows his business. We also explore why the chess world has exploded post-pandemic and how Tim is hiring, scaling, and staying focused in a competitive industry most people overlook.

If you’ve ever wondered how to build a hyper-local business that lasts, or how to make your niche offer sticky and profitable, this is a must-listen.

In this episode:

• Tim’s unexpected path from chess hustler to entrepreneur
• How he used Facebook groups, local meetups, and tournaments to grow
• Why quality beats marketing when it comes to retention
• What business owners can learn from chess (focus + strategy!)
• Why the post-pandemic hobby boom helped him scale fast
• His current bottlenecks and what he’s doing to fix them

Action Steps:

1. Follow through on what you say you’ll do — execution over ideas.
2. Don’t be afraid to aim high — just make sure you reverse engineer the steps.
3. Never give up — in chess and in business, perseverance wins.

Connect with Tim:

Website: masterpiecechessacademy.com

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

Facebook: Timothy Abeliahttps://masterpiecechessacademy.com/blogs/news/my-chess-story

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.

When Jessie Gabriel told me that less than 2% of venture capital funding goes to businesses founded by women, my jaw literally dropped. And that’s just the beginning of the equity gap we unpack in this episode.

Jessie—founder of the law firm All Places—is on a mission to change that. She works with founders and fund managers to make capital more accessible and equitable, and today she’s pulling back the curtain on how money really moves in the entrepreneurial world.

We dive deep into what venture capital is, how to know if your business is ready for funding, and the often-ignored topic of gender equity in the VC and private equity world. This episode is eye-opening for any entrepreneur, whether you’re service-based, product-based, or just curious about how money moves in this industry.

In this episode:

• What a venture capital fund is—and why it may (or may not) be right for your business
• The reality behind who controls capital in the U.S.
• Why less than 2% of venture funding goes to women founders—and what that really means
• How to protect ownership of your business even when raising money
• How Jesse turned grief and encouragement from her community into launching her own firm
• What every entrepreneur can do to help shift inequities in the industry

Action Steps for the week:

1. Spend 5 minutes researching a brand you support—learn who owns it and whether it aligns with your values.
2. Have a real conversation with a client or customer to understand your unique value from their perspective.
3. Pick up a business book that’s been on your radar and actually read it (or listen to it!) to spark new ideas.

Connect with Jessie:

Website: https://www.all-places.com/

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

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

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.

What does it take to go from making lattes to managing a thriving multi-location coffee brand? In this episode, I sit down with Rebecca Smith, founder and owner of Armistice Coffee in Seattle, to talk about her inspiring journey from barista to business owner—and the lessons she’s learned about leadership, trust, and growth along the way.

We dive into the behind-the-scenes of owning multiple coffee shops, the importance of hiring for heart over skill, and how Rebecca’s vision for community-first cafés shapes every decision she makes. She also opens up about selling one of her locations, navigating tough feedback, and what it really takes to scale a business rooted in passion and purpose.

Whether you're dreaming of opening your own storefront or just love a good entrepreneurial origin story, this one’s for you.

In this episode:

• How Rebecca went from employee to owner in the coffee industry
• The biggest lessons she learned from management roles
• Building a strong and consistent company culture
• Tips for hiring with heart (not just a résumé)
• How to prepare your business for growth—even if you're not ready yet
• What it's like managing people, roasting coffee, and building community
• Her personal action steps to move through fear and take the leap

Action Steps for the week:

1. Reach out to someone in your industry and ask questions—don’t be afraid to cold pitch a coffee chat.
2. Write down your wins and the things you know you’re good at—return to this when self-doubt creeps in.
3. Give yourself grace—entrepreneurship is hard, and progress doesn’t always look like success

Connect with Rebecca:

Armistice Coffee Website: https://armisticecoffeeco.com/

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

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.

What do you get when you blend a successful corporate career, motherhood, and a deep desire to create something meaningful? You get Motette—a modern children's clothing brand that’s elevated, intentional, and built with purpose.

In this episode, I sit down with Samantha Gold, the founder of Motette, to talk about how she left her tech and fashion executive roles to launch a bamboo-based clothing line for kids. We dive into what sparked her entrepreneurial leap, how she tapped into her community for design feedback, and why building trust with her customers is at the core of everything she does.

Samantha and I are both members of 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:

• Building a pre-launch community that actually converts
• Managing a product-based business from across the globe
• Creating trust and loyalty with customers from day one
• And how to move forward—even when you’re scared

Action Steps for the week:

1. Do the One Thing You’ve Been Putting Off
2. Get Outside Your Comfort Zone
3. Choose Courage Over Fear

Connect with Samantha:

Motette Website: https://shopmotette.com/

Motette Instagram: https://www.instagram.com/shopmotette

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.

In today's crowded online space, your story is your most powerful marketing tool. But how do you craft a brand video that emotionally connects with your audience and helps you stand out?

In this episodeI sit down with Mariana Henninger, founder of Brandmagnetic, to explore the power of emotional marketing and storytelling in business. With a background in documentary filmmaking for major outlets like Time Magazine, The Wall Street Journal, and NBC, Mariana shares how entrepreneurs can leverage their personal stories to build trust, establish authority, and attract the right clients.

In this episode:

• Why storytelling is essential in business and how it drives emotional connections
• The biggest mistake entrepreneurs make when sharing their brand story
• How to create a brand video that establishes trust and increases conversions
• The psychology behind emotional marketing and how it influences buying decisions
• Tactical steps to identify and craft your story in a way that resonates with your audience

Action Steps for the week:

1. Talk to your audience. 
2. Start testing your stories.
3. Use visuals to enhance emotion

Connect with Marianna:

Instagram: instagram.com/brandmagnetic

📹 Download the Free Cheat Sheet: brandmagnetic.com/cheatsheet

🎬 Mini Course: AI-Powered Storytelling for Brand Videos: brandmagnetic.com/ai

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.