College Detours Ignite a Filmmaking Path Off to college with dreams of photography or music, blunt family realism pushes a pivot from engineering’s grind to psychology and emerging environmental studies. An arts-focused partner opens the door to advanced cinematography night classes, transforming a hobby into craft. Small paid shoots follow—industrial, sports, and commercial—forcing mastery of camera, sound, lighting, budgeting, and post-production. Days in class, nights filming, and weekends editing on an eight-plate machine forge skills through relentless practice. Passion fuses with work, making “25-hour” days feel possible and setting the creative foundation.
Leveraging Film Skills to Fund an MBA Facing limited prospects with psychology and environmental studies, a business degree becomes the toolkit to run any creative life. A pitch to the dean secures a recruiting documentary—budget trimmed from $50,000 to $30,000—and academic credit tied to the film’s utility. Two years of filming inside the program capture rigor and the discipline of isolating key issues from noise. The finished film becomes a global recruiting asset, earns top marks, and validates the blend of art and commerce.
Building and Exiting Special Events Television With partners Dave Thomas and Scott McKenzie, a production company forms around one principle: own unique television formats. Sports concepts like Bobby Orr and the Hockey Legends and The Original Six turn retired stars into compelling weekly content. Don Cherry’s Grapevine ignites, expanding distribution and anchoring a thriving slate. Within two years the company is acquired, yielding the first meaningful exit and hundreds of thousands per founder.
Bundling Strategy Scales SoftKey to an IPO A night-course encounter with John Freeman reveals plotter-driven graphics software; a partnership is formed as SoftKey, launching KeyChart. After Hewlett-Packard declines bundling, competitors embrace it, moving millions of copies at about 12 cents per copy yet generating substantial profits. Freeman exits with cash and stock as the catalog expands, Comdex momentum grows, and private equity capital fuels scale. A public listing follows, and a morning glance at shares makes wealth suddenly tangible—proof that the journey, not money, powered the ascent and that entrepreneurial outcomes feel binary: zero, then a lot.
Getting Fired Sparks a Commitment to Ownership A high-school ice cream job ends abruptly after refusing to scrape gum, leading to instant firing and humiliating exit. The shock crystallizes a lifelong rule: never let someone else control livelihood again. Life divides into store owners and floor scrapers; both paths are valid, but ownership is the only acceptable choice. That moment launches the entrepreneurial path defined by personal freedom.
Pursue Freedom, Not Money: Solve Scalable Problems Entrepreneurship succeeds when driven by personal freedom, not greed. Making the first million requires solving a real problem for one person that many others share; it is among the hardest feats. The next five million is even harder; beyond that, wealth compounds through investing. First you operate to earn; then you invest to build—an evolution learned through the journey.
Raise Capital with Clarity, Credibility, and Command of Numbers The funding game rewards three absolutes: a vision anyone can grasp in 90 seconds, a compelling case for why this team will execute, and flawless command of business model and numbers. Margins, market size and growth, break-even share, competition, and cash flow must be answered without hesitation; bring a numbers expert if needed. These traits appear in every deal that gets financed, enabling the pursuit of freedom that underpins entrepreneurship and Shark Tank’s appeal. Capital only starts the journey, but clear communication makes others follow.