Resilience, Exits, and Venture Capital: Jackie Dinsmore's Entrepreneurial Odyssey

Julie's Big Gorgeous Goals: Official Workbook is here! Order your copy today.Did you know that mature entrepreneurs bring a wealth of diverse experiences to the table?  In this episode of Figure Eight, Jackie Dinsmore highlights the value of founders with life experience. Her venture capital firm, Extra Innings Ventures, embraces this philosophy by investing in seasoned individuals. Jackie and Julie also discuss how letting go of the helm to become an employee and eventually selling one's ownership requires adaptability and emotional preparedness. Her story provides invaluable lessons on the often-overlooked human side of business transactions.Jackie was a corporate lawyer at Blakes in Toronto, and subsequently worked as Assistant General Counsel at The Toronto Star. Originally intended as a side project to satisfy her non-legal creative side, Jacqueline launched FlapJackKids, a company that focuses on all reversible products for women and children. Jacqueline's products were featured in swag bags for Emmys and Oscars pre-parties, and can be found in thousands of stores in North America and worldwide. She has been named Top Mompreneur by Mompreneur Magazine and appeared in Forbes Magazine alongside Hilary Clinton and Barack Obama. Her company was featured numerous times in top press and media including The Toronto Star, The Globe and Mail, Ok Weekly, Us Weekly, Woman's World, USA Today, The Huffington Post and Woman's Day.Jacqueline was also one of the original owners of Caravel Law and since its sale, now acts as its Co-Managing Partner. Caravel Law is a revolutionary law firm of over 100 lawyers that has disrupted the legal services industry in Canada, by making big firm trained and in-house experienced lawyers available as fractional counsel to start-ups, F500 companies and everything in between. Its low overhead model ensures access to great lawyers at a reasonable cost. Jacqueline has had three successful exits and most recently started Extra Innings Ventures, a venture capital firm focusing on under-represented founders with life experience.Jackie's Transition from Law to Serial Entrepreneurship (00:01:24) Jackie's journey of practicing law before founding and exiting multiple companies, including her current venture capital firm.Challenges of Exits, New Partnerships, and Extra Innings Ventures (00:12:37) The emotional and strategic challenges of exiting businesses and finding the right partners for future ventures, including her venture capital firm focused on investing in underrepresented founders.Lessons from Product-Based Business (00:20:36) Reflections on mistakes made, managing inventory, and staying relevant in the fashion industry.Building a Founding Team (00:24:29) Lessons learned from building a founding team, scaling up, and managing people.Continuous Learning and Community (00:29:55) The importance of continuous adapting and surrounding oneself with a supportive community in entrepreneurship.More about Jackie: www.caravellaw.comwww.extrainningsventures.comLove the show or want to request a topic? Leave us a message (All submissions are anonymous, so if you'd like a reply, please include your email address!).You can connect with Julie on LinkedIn or Instagram. Find Julie's writing at her blog or by ordering her book Big Gorgeous Goals and the brand new official companion workbook! What did you think of this conversation? We'd love if you'd rate or review our show!