This amusing little romp through Greg Smith’s mind comes courtesy of his chatty side, conveniently edited for your reading pleasure and clarity. Spoiler alert: It might just inspire a career shift.
So, Greg decided to dive into the corporate law world—not because he’s a masochist or enjoys legal jargon, but because he fancied being at the epicenter of thrilling business maneuvers. After all, while CEOs might tango with a merger or an IPO twice in a lifetime, corporate lawyers get to throw down every day! It struck our hero that a few years drafting documents could offer more exhilarating corporate drama than an eternity of board meetings.
His quest for legal glory led him to law school, where he also discovered a gold mine: tutoring for the LSAT, a treasure trove that helped pay those monstrous student loans. Realizing that teaching wasn’t exactly a Netflix series (you know, the one with the non-stop plot twists), Greg craved a wider audience. After all, who wants to limit their impact to the amount of seating in a sterile classroom?
Thus, in 2005, our entrepreneurial wizard conjured up an automated course that began pulling in money faster than you could say “unexpected revenue stream.” One month, while juggling his law job, he directed his full attention to promoting this genius course and—wait for it—pulled in $10,000. That’s right, more than his corporate salary! If only all of us could find such a lucrative excuse to abandon our day jobs.
Others were suddenly all about that course creation life
Greg’s drive for entrepreneurship, probably fueled by those childhood memories of his parents’ constant brainstorming (but little follow-through, of course), hit him like a lightning bolt on an airplane. “Eureka! I must create a business!” he declared to the inflight magazine—possibly while ignoring his neighbor’s dull life story.
But instead of jumping straight into the course business, he took a detour into another startup—like taking the scenic route only to run into a dead end. Then, with the precision of a well-aimed boomerang, people started knocking on his door, asking for help to build their course platforms. In 2012, Thinkific was born, quite possibly after a caffeine-fueled night of brainstorming and several questionable takes on pumpkin spice lattes.
Enter: The brotherly dynamic duo.
Meet Matt, Greg’s younger brother and the tech savior of the hour—though they didn’t always see eye to eye. The office was a battlefield of ideas and ambitions, where both aspired to wear the CEO cape, blissfully unaware that this cape barely fitted one. After a rocky three years of familial tussles, Matt exited stage left for other ventures, but not before solidifying his spot as “that annoying sibling you still lovingly tolerate.”
Yet, as Thinkific soared to new heights, Matt transformed from the annoying sibling to the wise sage, returning as Chief Strategy Officer. With all the chaos of a growing company, their dynamic shifted from sibling squabbles to strategic discussions—an evolution that Greg hardly saw coming. Now, Matt plays advisor to the board and the go-to person when Greg needs to simply vent about the existential crises of running a startup.
Teaching kids that failure is an Olympic sport
Proudly raising his kids, Greg now embraces the concept of failure with the enthusiasm of a sports commentator. “What’s that? You failed at something? Fantastic! Let’s discuss how hard you fell!” he encourages. His daughter, at the tender age of three, learned that failing isn’t a shameful little secret but a ticket to opportunity. Who knew parenting could be so enlightening?
Now, during family discussions, his kids chat about their flops like they’ve just scored the top prize in a game show. “I failed!” they joyfully declare, which has led to some bewildered looks from other parents. But hey, at least they’re getting ahead of the curve—after all, who doesn’t want to find joy in stumbling while trying to walk?
