Success is rarely a straight line—it’s more like a bowl of spaghetti! In this episode of The Real Bottom Line, I chat with Jackie Dinsmore, a lawyer-turned-serial entrepreneur and investor, about her unconventional journey. Jackie shares how she built two successful businesses, navigated high-stakes exits, and disrupted the legal industry with her innovative approach at Caravel Law.

We dive into the highs, the challenges, and the lessons learned, covering everything from cash flow struggles in retail to the art of negotiating business sales. Plus, Jackie offers invaluable advice for entrepreneurs on staying resilient, surrounding yourself with the right team, and knowing when to pivot or push through.

If you’ve ever wondered what it takes to grow, sell, or reinvent a business, this episode is packed with actionable insights and candid stories you won’t want to miss!

Topics Covered:

• Jackie’s entrepreneurial journey from handbags to kids’ apparel
• The challenges of retail cash flow and inventory management
• Lessons from selling businesses and working with buyers
• Disrupting the legal industry with Caravel Law
• Practical advice for entrepreneurs on navigating the messy path to success

Subscribe for more insights from entrepreneurs who’ve been there, done that, and are ready to share the real bottom line!

📌 Links Mentioned:

• Connect with Jackie Dinsmore: Caravel Law Website

Join us for the Bottleneck to Breakthrough 5-Day Challenge, designed specifically for ambitious and growth-oriented business owners who are feeling overwhelmed and hitting revenue plateaus. In just 60 minutes a day, over the course of 5 days, we will provide you with the blueprint to go from bottleneck to breakthrough by reframing your relationship with time. This challenge will help you break through revenue plateaus, spend more time in your zone of genius, and build a more valuable business – even if you feel like you've tried everything and are time-starved.

Join the Bottleneck to Breakthrough 5-Day Challenge. Here's what you'll learn each day:

Day 1: Design Your Ideal Day

• Explore what your ideal day looks like as an entrepreneur and how to allocate your time based on entrepreneurial time rules

Day 2: Unlock Your Genius

• Shed tasks outside your zone of genius and focus on activities that energize and fulfill you

Day 3: Master Letting Go

• Analyze tasks and activities, determine their fit in your zone of genius, and understand the cost of holding onto them

Day 4: Leverage Your Time Blueprint

• Build a step-by-step process to shed undesired or time-consuming activities, explore delegation in a new way, and escape business jail

Day 5: Build Momentum

• Learn how to execute your ideal day by chunking down activities, overcoming forces of perfection, procrastination, fear, and ego, and amplifying growth drivers for your business.

Register at https://bottlenecktobreakthrough.com/

In this episode of The Real Bottom Line, I sit down with Talmar Anderson, founder of Boss HQ, to discuss one of the most crucial aspects of scaling any business—building the right team. Talmar shares her journey from being the "number two" in law firms to becoming a successful entrepreneur, and she breaks down the key difference between your Dream Team and your Freedom Team.

We dive into the mindset shifts business owners need to make, how to stop hiring for potential, and why building a team that works without you is essential for growing—and selling—your business. If you're an entrepreneur looking to step into the CEO role and create a business that runs smoothly without being dependent on you, this episode is for you.

Key Topics:

• Talmar’s personal journey from employee to entrepreneur
• The difference between the Dream Team and the Freedom Team
• Why hiring for potential can hold your business back
• How to build trust and delegate effectively as a boss
• The importance of creating a business that doesn’t rely on you

Join us for the Bottleneck to Breakthrough 5-Day Challenge, designed specifically for ambitious and growth-oriented business owners who are feeling overwhelmed and hitting revenue plateaus. In just 60 minutes a day, over the course of 5 days, we will provide you with the blueprint to go from bottleneck to breakthrough by reframing your relationship with time. This challenge will help you break through revenue plateaus, spend more time in your zone of genius, and build a more valuable business – even if you feel like you've tried everything and are time-starved.

Join the Bottleneck to Breakthrough 5-Day Challenge. Here's what you'll learn each day:

Day 1: Design Your Ideal Day

• Explore what your ideal day looks like as an entrepreneur and how to allocate your time based on entrepreneurial time rules

Day 2: Unlock Your Genius

• Shed tasks outside your zone of genius and focus on activities that energize and fulfill you

Day 3: Master Letting Go

• Analyze tasks and activities, determine their fit in your zone of genius, and understand the cost of holding onto them

Day 4: Leverage Your Time Blueprint

• Build a step-by-step process to shed undesired or time-consuming activities, explore delegation in a new way, and escape business jail

Day 5: Build Momentum

• Learn how to execute your ideal day by chunking down activities, overcoming forces of perfection, procrastination, fear, and ego, and amplifying growth drivers for your business.

Register at https://bottlenecktobreakthrough.com/