Influence, Authenticity, and the Art of Marketing Karma

What's the secret to taking five companies public and raising over $100 million? According to Jorge Olson, it all comes down to personal branding—a philosophy he's refined across decades.

In today's hyper-competitive business landscape, personal branding has emerged as a critical factor in entrepreneurial success. Jorge Olson, who has taken five companies public and raised over $100 million, reveals that personal branding isn't just a marketing strategy—it's the foundation upon which business empires are built. In this episode of the Dead Pixels Society podcast, Olson shares his remarkable journey, beginning with studying influence at just 12 years old before transitioning into marketing. By 27, he had reached the executive level as a Vice President of Marketing, eventually becoming a serial entrepreneur across multiple industries. His philosophy centers on a crucial question that he believes every entrepreneur should ask from day one: "What is the exit?" This perspective shapes how businesses approach growth, investment, and ultimately, success.

For entrepreneurs in traditional family businesses facing market disruptions, Olson emphasizes the importance of developing comprehensive systems. "If a new owner-operator is coming to the business and they have no idea what to do, you're both in trouble," he explains. Documenting processes for accounting, sales scripts, customer lists, pricing mechanisms, and procurement procedures creates transferable value. This systematic approach addresses one of the primary reasons why an estimated 80% of businesses listed for sale never actually sell—they lack the necessary infrastructure to transition successfully to new ownership.