Episode #22
Episode 22 • From Selling a Business to Building a New One: The Money, Mindset & Risks Behind Entrepreneurship with Mark Condon
What happens when you sell a business, suddenly have to figure out what to do with the money, and realize you don't actually understand your own finances? For Mark Condon , that moment completely changed the trajectory of his career. After running his own business from ages 21–32, Mark transitioned into financial services in 2017. Today, he's a financial planner helping individuals, families, and business owners navigate cash flow management, investment management, life and disability insurance, tax planning, retirement planning, and employee retirement plans. But that's only half of his entrepreneurial story. In 2022, Mark launched iPupPee , a physical product company created to strengthen the connection between dogs and their human owners. The idea grew out of Mark's experience hosting Boston's Best , where he interviewed Massachusetts entrepreneurs and business owners—including our very own Ryan Wilson. In this episode of Real Estate for Real Life , Ryan Wilson sits down with Mark to talk about what it really takes to build a business, manage money, take calculated risks, and turn an idea into something real. In This Episode, We Talk About: • The realities of entrepreneurship and business ownership • What Mark learned from running his first business • How selling a business led him into financial planning • The financial mistakes entrepreneurs and business owners commonly make • Why cash flow management matters more than revenue • Investing, tax planning, insurance, and building long-term wealth • How entrepreneurs can balance business growth and personal financial security • What it takes to turn an idea into a physical product • The story behind iPupPee and how Mark brought the concept to life • Taking risks, changing careers, and starting over • The relationship between money, mindset, and entrepreneurship Whether you're a real estate agent, entrepreneur, small business owner, investor, financial planner, aspiring business owner, or simply someone who wants to become better with money, this conversation is packed with lessons you can apply to your own life and business. ABOUT REAL ESTATE FOR REAL LIFE Real Estate for Real Life goes beyond buying and selling real estate. Hosted by Ryan Wilson and Courtney Gauchman , the podcast brings entrepreneurs, business owners, industry experts, and leaders from outside of real estate to the table to uncover the strategies, failures, mindset shifts, and lessons that can help all of us build better businesses and better lives. Because the best business lessons don't always come from your own industry. CONNECT WITH MARK CONDON Website: vertexplanning.wpengine.com & ipuppee.com Instagram: @markcondon13 LinkedIn: Mark Condon https://www.wilsongroupre.com/ @wilsongroup Produced by: Taylor Bono and Andy DeMattio For inquiries or interest in becoming a guest on Real Estate For Real Life, email: Andy@WilsonGroupRE.com .
