Entrepreneur-turned-investor Andrew Wilkinson, founder and chairman of Tiny, a Victoria, Canada holding company that invests mostly in tech, joined Julia La Roche on episode 180 to share his new book, “Never Enough: From Barista To Billionaire.

Once a barista in a small cafe making $6.50 an hour, Andrew Wilkinson built a business valued at over a billion dollars by the time he was 36—and yet, his path to success was anything but a straight line.

In Never Enough, Wilkinson pulls back the curtain on the lives of the ultra-rich, sharing insights into building a successful business that has been called a “Berkshire Hathaway, but for internet companies,” and a surprising first-person account of what it's actually like to become a billionaire.

Never Enough features both the lessons Wilkinson has learned as well as the many mistakes made on the road to wealth—some of which cost him money, happiness, and important relationships.

Taking a "no secrets" approach to stories the wealthy rarely reveal, Wilkinson is unwaveringly honest about some of the unexpected downsides of money: its toxic effect on personal relationships, how the lifestyles of the rich and famous aren't all they're cracked up to be, and how competition with peers leaves everyone—even billionaires—feeling like they never have enough.

In this book, you'll discover:

A candid glimpse into the lives of the super-rich and what truly matters beyond money
Insights on building a successful business from the ground up
Lessons learned from the mistakes made on the journey to his fortune
The surprising realities of life as a billionaire and the challenges that come with extreme wealth

In this rare and deeply honest account, Wilkinson examines his journey to nine zeros, what came after that pinnacled number, and the essential things money can't buy.

Links:

Book: https://www.amazon.com/Never-Enough-Billionaire-Andrew-Wilkinson/dp/1637744765

Twitter/X: https://x.com/awilkinson

0:00 Intro and welcome Andrew Wilkinson

1:48 Macro view

6:23 AI

10:00 'Never Enough' book

11:35 A form of self-therapy

13:00 If you swim with the sharks, you’ll become one

14:00 Making things right

17:00 Starting businesses as a teen

#180 Andrew Wilkinson On Going From A Barista To A Billionaire, Building Tiny 'The Berkshire Hathaway' Of Tech, And Life Lessons From Warren Buffett, Charlie Munger, And Bill Ackman

The Julia La Roche Show

#180 Andrew Wilkinson On Going From A Barista To A Billionaire, Building Tiny 'The Berkshire Hathaway' Of Tech, And Life Lessons From Warren Buffett, Charlie Munger, And Bill Ackman