Ep. 18 A Brand Worth Buying with Jackie Dinsmore
In this episode of the Legacy Branding Podcast, host Laura Beauparlant sits down with Jacqueline Dinsmore – entrepreneur, legal innovator, and co-managing partner of Caravel Law. Jackie shares the story behind building and selling multiple businesses, including FlapJackKids, which she co-founded with her mom, and Caravel Law, which was acquired by private equity in 2023.
They explore what it takes to build a brand that’s truly worth buying, the challenges of working with family, and what it’s like to stay on after a sale. Jackie also dives into how Caravel is disrupting the legal industry and why she launched Extra Innings Ventures to support underrepresented founders in their “second act.”
Whether you’re scaling, selling, or just starting out, this episode is packed with honest insights on legacy, leadership, and building a business that lasts.
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Jackie began her career at Blakes and later served as Assistant General Counsel at Torstar. Driven by her entrepreneurial spirit, she founded FlapJackKids, a globally successful brand whose products have been featured in swag bags for the Oscars pre-parties and are sold in thousands of stores worldwide. Her work has earned recognition in Forbes Magazine alongside Barack Obama, with FlapJackKids highlighted in OK! Weekly, Us Weekly, The Huffington Post, and USA Today.
Jackie was previously Co-Owner and is now Co-Managing Partner of Caravel Law, a revolutionary law firm of over 100 in-house-trained lawyers. Caravel’s innovative, low-overhead model has redefined legal services, helping legal departments and entrepreneurs tackle legal pain points at a more reasonable cost. Jackie’s leadership and impact have earned her accolades, including being named one of Canada’s Top 25 Most Influential Lawyers by Canadian Lawyer and receiving the Female Trailblazer of the Year award from the Canadian Law Awards.
As an entrepreneur, Jackie has achieved three successful business exits and recently launched Extra Innings Ventures, a venture capital firm dedicated to funding underrepresented founders with invaluable life experience.
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00:00 Introduction to the Legacy Branding Podcast
00:42 Meet Jackie Dinsmore: Entrepreneur, Investor, and Legal Innovator
01:34 Jackie's Journey: From Flap Jack Kids to Caravel Law
03:05 Knowing When It’s Time to Sell Your Business
07:30 Family Business Dynamics: Challenges and Rewards
10:00 Lessons from Selling to Private Equity
13:30 Disrupting the Legal Industry with Innovation
17:00 Embracing AI and Technology in Legal Services
21:00 Legal Pitfalls Entrepreneurs Should Avoid
25:00 Extra Innings Ventures: Supporting Experienced Founders