In early July, Victoria-based entrepreneur Andrew Wilkinson, the self-styled “Warren Buffett of Tech'' launched a book called “Never Enough: From Barista to Billionaire.” In a span of about 15 years, Andrew went from being a dropout barista to designing websites to palling around with the likes of Bill Ackman, Charlie Munger, among other leading lights of the finance world. He may not be a household name among the Laurentian business elites. But he’s semi-big in US tech circles. No less an authority than CNBC - home of modern-day Socrates, James J. Cramer - labeled him a billionaire in 2020. A Canadian billionaire at age 34! Wilkinson would have reached that status faster than Jeff Bezos, Elon Musk and Warren Buffett. More impressively, unlike those three, Andrew never had outside investors until he partnered with Bill Ackman and Howard Marks to buy a business when he was around 33 years of age. And this all started from designing websites - his first sale was for $2,500. How does this happen? What is Andrew’s secret sauce? Was he ever a “billionaire", as that term is commonly understood by mathematicians?
Certainly, Andrew has at times shown an ability to make big scores from non-obvious investments. The best example is his friendship with Bill Ackman. They first met after Andrew won a charity lunch auction for $58k. Andrew then sought and obtained backing from Bill for a $20+ million deal in 2019— a year before being described as a billionaire by CNBC. Charlie Munger might have been even more enamored. Charlie chaired a publicly-traded software business called The Daily Journal. Andrew has claimed that in his first meeting with Charlie Munger, the latter proposed a merger between The Daily Journal and Andrew’s then-private holding company, Tiny. Munger cultists know he was very closely associated with The Daily Journal - he was a director there longer than he was with Berkshire Hathaway. How does a whippersnapper from Victoria become a potential business heir of Charlie friggin’ Munger?
Andrew has a certain cunning and an instinct for incubating businesses and getting them off the ground. He claims to have booked $15k in web design business in his very first month as a total newbie. But where Andrew is truly world-class is that he is a master at creating perceptions far beyond mundane reality. At his core, Andrew is a good writer and an exceptional story-teller. He was briefly in a journalism program at Ryerson. Andrew has used the writing playbook to propel himself, a playbook that was also favored by Gwyneth Paltrow (her Goop! started as a weekly newsletter, before selling vaj-jay-jay contraptions I am not familiar with).
Andrew has a gift for finding the perfect angle for recounting things that happen to him. He is shrewd in pursuing attention, whether to market his businesses or raise his profile. Good writers are sometimes akin to a magician - misdirecting the reader’s mind and then sucker-punching them. This may have real-world applications too. Over two decades, Andrew, the journalism dropout, has become a multi-media powerhouse at misdirecting minds and shaping perceptions. He deploys for this a much more subtle and sophisticated playbook than that of the other great perception-shaping contemporary, Donald J. Trump. For one thing, Andrew is much more candid about some of his mistakes. But that may be a calculation too.