Business Over Cocktails - Behind the Business - Real Talk with Female Entrepreneurs

Leaving Corporate Was Only the Beginning w/ Tracy Medeiros

Have you ever left one job only to realize you brought all of your old habits with you? When Tracy Medeiros lost her father, she and her husband made the life changing decision to move to Hawaii. She planned to continue working for her corporate employer after the move, but when that opportunity fell through, she accepted a new job in Hawaii. A year later, that company planned to lay her off, and instead of starting over, Tracy turned them into her very first client. What began as an unexpected career change eventually became a business dedicated to helping entrepreneurs create companies that support the lives they want to live.  In this episode, Tracy shares the story behind her unexpected journey into entrepreneurship and the lessons she learned along the way. We talk about the corporate habits she had to unlearn, why so many successful businesses have messy back ends, how entrepreneurs become the biggest bottlenecks in their own companies, and why redefining success often starts with building systems that create more freedom instead of more work.  If you're ready to stop carrying old habits into your next chapter and start building a business that truly supports the life you want, this episode will challenge the way you think about success, freedom, and growth. Connect with Tracy: Medeiros Consulting Substack - https://medeirosconsulting.substack.com/ [https://medeirosconsulting.substack.com/] LinkedIn - www.linkedin.com/in/medeirosconsulting [http://www.linkedin.com/in/medeirosconsulting] Instagram - https://www.instagram.com/medeirosconsulting/ [https://www.instagram.com/medeirosconsulting/] Chapters: 01:40 Tracy's unexpected path to entrepreneurship 05:55 The corporate mindset that followed her 10:05 Why boundaries are harder than they seem 13:50 What a Business Design Architect actually does 18:55 Why successful businesses are often messy 22:50 Hiring isn't always the answer 27:20 Why systems create more freedom 31:45 Letting go of hustle culture 35:30 Building a business around your life 38:25 Building routines that support your business  40:15 Tracy's advice for scaling with intention Upcoming Events: Chicago Retreat - July 14-16, 2026 - https://laurennajar.myflodesk.com/iid9wbr2yc [https://laurennajar.myflodesk.com/iid9wbr2yc] Napa Retreat - October 5-8, 2026 - https://laurennajar.myflodesk.com/cetj223rsr [https://laurennajar.myflodesk.com/cetj223rsr] Growth & Connect Events - https://laurennajar.myflodesk.com/hb2a0mwbqw [https://laurennajar.myflodesk.com/hb2a0mwbqw] Let’s Stay Connected: → Follow Lauren on Instagram: www.instagram.com/laurennajar [https://www.instagram.com/laurennajar] → Learn more or work with me: www.laurennajar.com [https://www.laurennajar.com] → Follow Business Over Cocktails on IG: www.instagram.com/businessovercocktails [https://www.instagram.com/businessovercocktails] → Attend Growth & Connect retreats & events: www.instagram.com/growthandconnect [https://www.instagram.com/growthandconnect] 🎧 Subscribe & Review: Love the episode? Don’t forget to subscribe, leave a review, and share with a friend who needs a business boost and a good chat over a cocktail.

Stop Selling. Start Dating Your Customers w/ Hunter Myers

What if the reason people aren't buying has nothing to do with your offer? Many business owners spend their time trying to generate more leads, create more content, or improve their sales process. But according to Hunter Myers, the problem may be much simpler. You're treating customers like transactions instead of relationships. In this episode, she shares her Matchmaker Method and explains why businesses should start thinking about customer relationships the same way they think about dating. Hunter walks through her four-part client connection framework and explains why buyers may need as many as 50 to 100 touchpoints before making a purchasing decision. You'll learn how to attract better-fit clients, reduce friction throughout the buyer journey, create stronger customer experiences, and build relationships that continue generating loyalty and referrals long after the initial sale.  So, if you're ready to learn how to attract the right clients, create stronger customer connections, and turn buyers into loyal advocates, this episode is for you.  Connect with Hunter: LinkedIn: https://www.linkedin.com/in/hunter-myers-cnxncreativeco/ [https://www.linkedin.com/in/hunter-myers-cnxncreativeco/] Youtube: https://www.youtube.com/@cnxncreativeco [https://www.youtube.com/@cnxncreativeco] Website: https://www.cnxncreativeco.com/ [https://www.cnxncreativeco.com/] Brand Attractiveness Assessment: https://forms.gle/N4Btymx7y3uGz7V59 [https://forms.gle/N4Btymx7y3uGz7V59]  Chapters: 00:25 Why you should start dating your customers 02:20 How to define your ideal client 03:45 The exercise for finding your best-fit clients 04:50 How to create chemistry with buyers 06:00 How Woxer solved a customer problem  07:10 Why buyers need more touchpoints than ever 08:05 How to reduce friction in the buyer journey 09:00 Creating content that answers questions before sales calls 09:45 Why representation matters in your marketing 10:35 The touchpoints you may be overlooking 11:40 Why most businesses fail after the sale 12:20 The referral strategy most businesses skip  Upcoming Events: Chicago Retreat - July 14-16, 2026 - https://laurennajar.myflodesk.com/iid9wbr2yc [https://laurennajar.myflodesk.com/iid9wbr2yc] Napa Retreat - October 5-8, 2026 - https://laurennajar.myflodesk.com/cetj223rsr [https://laurennajar.myflodesk.com/cetj223rsr] Growth & Connect Events - https://laurennajar.myflodesk.com/hb2a0mwbqw [https://laurennajar.myflodesk.com/hb2a0mwbqw] Let’s Stay Connected: → Follow Lauren on Instagram: www.instagram.com/laurennajar [https://www.instagram.com/laurennajar] → Learn more or work with me: www.laurennajar.com [https://www.laurennajar.com] → Follow Business Over Cocktails on IG: www.instagram.com/businessovercocktails [https://www.instagram.com/businessovercocktails] → Attend Growth & Connect retreats & events: www.instagram.com/growthandconnect [https://www.instagram.com/growthandconnect] 🎧 Subscribe & Review: Love the episode? Don’t forget to subscribe, leave a review, and share with a friend who needs a business boost and a good chat over a cocktail.

Why Fitting In Nearly Cost Her Business w/ Hunter Myers

What if the biggest thing holding your business back is trying to be someone you're not? For years, Hunter Myers believed she needed to fit a certain mold to be successful. She built a brand around what she thought clients wanted, leaned into trends that did not feel natural, and found herself performing instead of showing up authentically. It wasn't until she embraced who she really was that her business began to feel aligned, sustainable, and genuinely successful. In this episode, Hunter shares her unconventional journey from aspiring artist and writer to founder of Verdure Design Co. After earning degrees in English and sociology, moving to Austin without a clear plan, and unexpectedly landing a graphic design role, she discovered a path that blended creativity, storytelling, and human connection. She opens up about the lessons she learned through entrepreneurship, why branding is really about relationships, how community influences buying decisions, and the role boundaries play in building a business that lasts. Along the way, she reveals why treating clients like long-term relationships can completely change the way you market and grow your business.  If you're ready to build a brand that feels authentic, attracts the right people, and supports long-term growth, this episode is for you. Connect with Hunter: LinkedIn: https://www.linkedin.com/in/hunter-myers-cnxncreativeco/ [https://www.linkedin.com/in/hunter-myers-cnxncreativeco/] Youtube: https://www.youtube.com/@cnxncreativeco [https://www.youtube.com/@cnxncreativeco] Website: https://www.cnxncreativeco.com/ [https://www.cnxncreativeco.com/] Chapters: 00:40 The story behind Verdure Design Co. 06:40 Why luxury branding never felt authentic 11:20 Growing into the right brand identity 16:20 How an artist became a brand designer 22:00 Why community matters in branding 33:50 Treating clients like long-term relationships 40:40 Building a sustainable business 42:20 Setting boundaries through your values 46:00 Walking your talk as a business owner Upcoming Events: Chicago Retreat - July 14-16, 2026 - https://laurennajar.myflodesk.com/iid9wbr2yc [https://laurennajar.myflodesk.com/iid9wbr2yc] Napa Retreat - October 5-8, 2026 - https://laurennajar.myflodesk.com/cetj223rsr [https://laurennajar.myflodesk.com/cetj223rsr] Growth & Connect Events - https://laurennajar.myflodesk.com/hb2a0mwbqw [https://laurennajar.myflodesk.com/hb2a0mwbqw] Let’s Stay Connected: → Follow Lauren on Instagram: www.instagram.com/laurennajar [https://www.instagram.com/laurennajar] → Learn more or work with me: www.laurennajar.com [https://www.laurennajar.com] → Follow Business Over Cocktails on IG: www.instagram.com/businessovercocktails [https://www.instagram.com/businessovercocktails] → Attend Growth & Connect retreats & events: www.instagram.com/growthandconnect [https://www.instagram.com/growthandconnect] 🎧 Subscribe & Review: Love the episode? Don’t forget to subscribe, leave a review, and share with a friend who needs a business boost and a good chat over a cocktail.

The 30 Day Habit That Increased My Confidence w/ Lauren Najar

What if the breakthrough you're waiting for doesn't require a bigger strategy, but a smaller daily commitment? Big business goals are exciting, but they often leave entrepreneurs chasing results instead of building the habits that actually create them. In this solo episode, I share why I committed to running 39 miles during my birthday month and how that personal challenge became a great reminder of what consistency can accomplish. I'm sharing why I believe 30 day sprints are one of the best ways to build confidence, how focusing on daily actions creates momentum, and why simple habits like reaching out to five new people each day can lead to bigger opportunities, stronger relationships, and long term business growth. If you've been setting big goals but struggling to follow through, this episode is for you. Chapters: 00:25 Why I committed to 39 miles in 30 days 03:00 How keeping promises builds confidence 04:15 The habit that changed my business 06:15 What I learned from running every day 07:45 My next 30 day business challenge 09:00 Daily habits over revenue goals  10:20 The power of consistent daily actions 11:35 Examples of 30 day business sprints 13:20 Focus on habits, not outcomes 14:10 Your 30 day challenge starts now Upcoming Events: Chicago Retreat - July 14-16, 2026 - https://laurennajar.myflodesk.com/iid9wbr2yc [https://laurennajar.myflodesk.com/iid9wbr2yc] Napa Retreat - October 5-8, 2026 - https://laurennajar.myflodesk.com/cetj223rsr [https://laurennajar.myflodesk.com/cetj223rsr] Growth & Connect Events - https://laurennajar.myflodesk.com/hb2a0mwbqw [https://laurennajar.myflodesk.com/hb2a0mwbqw] Let’s Stay Connected: → Follow Lauren on Instagram: www.instagram.com/laurennajar [https://www.instagram.com/laurennajar] → Learn more or work with me: www.laurennajar.com [https://www.laurennajar.com] → Follow Business Over Cocktails on IG: www.instagram.com/businessovercocktails [https://www.instagram.com/businessovercocktails] → Attend Growth & Connect retreats & events: www.instagram.com/growthandconnect [https://www.instagram.com/growthandconnect] 🎧 Subscribe & Review: Love the episode? Don’t forget to subscribe, leave a review, and share with a friend who needs a business boost and a good chat over a cocktail.

Why Turning 39 Hit Harder Than I Expected w/ Lauren Najar

What happens when you reach the age that changed your parent's life forever? As I reflect on my 39th birthday, I found myself thinking about a number that carries deep meaning. Thirty-nine was the age my mom was diagnosed with colon cancer, and reaching that same milestone brought up unexpected emotions about grief, family, identity, and the passage of time. In this deeply personal episode, I'm sharing memories of my mother's cancer journey, the challenges of losing both parents at a young age, and the realization that I never got the chance to know my mom as an adult. As I reach the same age she was when she was diagnosed, I reflect on how grief evolves over time and the surprising ways her influence continues to shape my leadership style, work ethic, and approach to building a business today.  If you've ever lost someone you love, struggled with unanswered questions, or wondered how the people who shaped you continue to influence your life, this episode will leave you thinking differently about legacy, grief, and the stories we carry with us. Chapters: 00:40 Why Turning 39 Feels So Significant 03:20 The Story Behind My Mom's Cancer Diagnosis 07:40 Losing My Mom at 21 Years Old 11:10 How Grief Changes As You Get Older 14:00 The Reality of Never Knowing My Mom as an Adult 17:00 The Questions I Wish I Could Ask 20:20 Why Reaching Certain Ages Feels Different 24:10 The Impact My Mom Still Has on My Life  27:30 The Leadership Lessons I Learned From Watching My Mom 30:20 How My Mom Influenced My Business Without Knowing It Upcoming Events: Chicago Retreat - July 14-16, 2026 - https://laurennajar.myflodesk.com/iid9wbr2yc [https://laurennajar.myflodesk.com/iid9wbr2yc] Napa Retreat - October 5-8, 2026 - https://laurennajar.myflodesk.com/cetj223rsr [https://laurennajar.myflodesk.com/cetj223rsr] Growth & Connect Events - https://laurennajar.myflodesk.com/hb2a0mwbqw [https://laurennajar.myflodesk.com/hb2a0mwbqw] Let’s Stay Connected: → Follow Lauren on Instagram: www.instagram.com/laurennajar [https://www.instagram.com/laurennajar] → Learn more or work with me: www.laurennajar.com [https://www.laurennajar.com] → Follow Business Over Cocktails on IG: www.instagram.com/businessovercocktails [https://www.instagram.com/businessovercocktails] → Attend Growth & Connect retreats & events: www.instagram.com/growthandconnect [https://www.instagram.com/growthandconnect] 🎧 Subscribe & Review: Love the episode? Don’t forget to subscribe, leave a review, and share with a friend who needs a business boost and a good chat over a cocktail.