The Number

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
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Creators and Guests

Host
Wendy Brookhouse
The Financial Planner for ambitious growth oriented Entrepreneurs
Editor
Shaun Whynacht
I’m the founder of Blue Cow Marketing and father of an amazing little boy. helping other business owners overcome challenges is my passion.

What is The Number?

The Number is a business podcast about the numbers that actually run your business.

Each episode focuses on one number. Revenue, profit, cash flow, capacity, time, valuation, customer cost, risk, or exit readiness.

Hosted by Wendy Brookhouse, and often joined by Kelsey MacAulay, the show breaks down what that number means, why it matters, and how it should influence the decisions you make as an owner.

Some episodes feature guests. Some are honest conversations. Some are solo deep dives.

If you own a business and want better clarity, better decisions, and better outcomes, it starts with knowing your numbers.