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Never Enough: From Barista to Billionaire

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Andrew Wilkinson, touted as the Warren Buffett of tech, pulls back the curtain on the lives of the ultra-rich in this memoir outlining Wilkinson’s rapid rise from barista to successful entrepreneur.

Readers will get fresh insights into building a successful business and a surprising, first-person account of what it’s actually like to become a billionaire.

By the age of thirty-five, Andrew Wilkinson had built a business worth over a billion dollars, but his path to success was anything but a straight line. Never Enough shares 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 the story billionaires rarely tell, Wilkinson is unwaveringly honest about some of the unexpected downsides of wealth. Money’s 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 rare and deeply honest glimpse into the life of a billionaire, Wilkinson examines not only his journey to nine zeros but also what comes after that pinnacled number—something, as Wilkinson has come to realize, that money can’t buy.

288 pages, Hardcover

Published July 9, 2024

427 people are currently reading
6702 people want to read

About the author

Andrew Wilkinson

1 book77 followers
Andrew Wilkinson is the founder of Tiny, a Canadian holding company that owns over 40 businesses ranging from Dribbble, a social network for designers, to the AeroPress coffee maker. Tiny buys wonderful businesses from founders and holds them for the long-term. Andrew successfully bootstrapped the business from zero to hundreds of millions of dollars in value and still holds majority ownership. He has committed to give away at least half of his fortune via his foundation, Tiny Foundation, which is primarily focused on global health, investigative journalism, non-profit reform, and medical research. He lives in Victoria, Canada.

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5 stars
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Displaying 1 - 30 of 295 reviews
Profile Image for Vitalijus Sostak.
138 reviews24 followers
July 13, 2024
This is not a business or investing book. It's not a self-help or life philosophy book, for sure.
It's an autobiography written by a 38 year old. Elegant tight prose about a life story that stands out, entertains and has few lessons to teach along the way.

A flawed childhood, money-related anxiety, fragile relationships and spending insecurity - there is some misery in everyone's life and wealthy are not different.

We, humans, evolved to push, to strive, to stress and rarely be satisfied. Dial it up to eleven and you'll get a seasoned entrepreneur - a mad squirrel with dozens of trees full of nuts and yet still freaking out about the upcoming winter.

After all those tribulations, the book ends on a constructive, bright note (no spoilers!).

Read it.
100 reviews9 followers
August 5, 2024
Nothing groundbreaking in here, but absolutely worth reading. Main takeaway is that more money / success / stuff / fame, etc. won’t make you happy. In fact, these things come with real cost (like maintaining all the stuff, everything you do in the public eye, and needing to hire security to protect yourself). You won’t be happy until you decide that you truly have enough.
Profile Image for Alex Blackie.
5 reviews2 followers
August 3, 2024
I probably would not have bought this book if not for my personal connection to MetaLab as the place I jumpstarted my career as a teenager many years ago. In all honesty, I expected to poke fun at it. An autobiography from this guy from my hometown that made a bunch of money? Really?

Well, then I read it in its entirety over the course of two consecutive days.

Maybe it was the "barista to billionaire" title that made me think this was going to be some self-aggrandizing manifesto. But this book was not what I expected at all. It's is a winding road through the inner monologue of someone grappling with the burdens of success, recounting the wins, sure, but also the failures--the low points, the struggles, the stress, the guilt of inequity... Mistakes laid bare so the wisdom can be shared.

I actually enjoyed it.

The first half of the book was interesting for me mostly for the lore -- the origin story that intersects my own. What really captured me, however, was the latter half...



All in all, "Never Enough" surprised me. I came in a skeptic, and left with sympathy. Maybe there can be some good billionaires after all.

However, I lost $21.60 on my $40 investment in Tiny's stock when they went public. Ignore everything I said above; I can never forgive Andrew for this.
Profile Image for Major B.
172 reviews
July 21, 2024
This was a great book! It was such an interesting story that taught valuable lessons about life and money.
Profile Image for Nikhil.
95 reviews25 followers
October 6, 2025

Simply put, this is a book about what to do when you dont have enough money! And then, what to do when you think you have too much! Duh!!

What makes it read-worthy is the story of Andrew Wilkinson, the author and a Canadian tech investor who likes to style himself ala Buffet-Munger, which happens in between!

Born in a middle-class family, Andrew goes through childhood with the knowledge that he and his family (are not poor) just dont have enough money to enjoy the privileges of life that they’d want to. He sees his hard-working father’s internal and external struggles between desires and financial ability contrasted with his mother’s strong constitution - meticulous to a fault when it comes to managing the family’s finances.

Someone told me recently that the ‘feeling of denial’ is a much more powerful motivator than the desire for achievement. It is that ‘feeling of denial’ combined with a fear that he may end up like his father / family - just not having enough - that drive Andrew as he traverses from a $6.5 / hour barista to a web-developer to a business owner and then owner of many businesses (from nothing to too-much!).

As successful entrepreneurs, Andrew (and his accidental yet permanent partner, Chris) realise that the key to any business is a certain amount of laziness - i.e. figuring out a better (more efficient) way to deliver on a customer’s need!

“A business, even one run by a twelve-year-old, is at its core about solving problems for other people.”

As Andrew struggles with managing his venture, he is miserable as CEO doing the same things that he abhors, day after day, including wining and dining with clients, following up on project delivery, ensuring clients pay up on time, and so on.

A forced vacation leads Andrew to an epiphany:

“…there is always somebody else who loves the job you hate.”

You just gotta find them!!

As he makes more and more money, Andrew finds himself on the ‘hedonic treadmill’ (love the phrase!!) - one that you get on when you start seeing more money than your immediate needs are! He tries to buy his way to happiness, but ends up with the empty stomach feeling constantly!

Faced with the vagaries of business, he realises the need to learn about saving and investing, marking the entry of Munger and Buffet (their books and writings initially) into his life!

Even before Andrew meets Munger, Munger’s advice changes their life - “invert, always invert!” Munger said “problems are often easiest solved in reverse” and explained that it’s much easier to think about what you don’t want than what you do. So they follow Munger’s advice and remove (reduce) things from their life that they hate. When I say remove, i just mean they find someone else who ‘loves’ to do those things!

“It’s not enough to do what you love. You also have to stop doing what you hate.”

And then they meet Munger! This is truly the twist in the plot though not in the manner Andrew would have ever imagined! They follow-through on the process of inversion and decide to decline Munger’s business proposition. Who does that!!!

The story starts with his childhood anxiety of ‘not having enough’. The story ends when Andrew loses this anxiety and realises that he finally has more than enough.

Herein comes the guilt-trip - of having made it while others along the road didn’t!

This is when Bill Ackman, a well-known hedge-fund investor and their friend, introduces Andrew to Warren Buffet. And with Ackman and Buffet’s guidance, Andrew decides what to do with his ‘more than enough’ wealth!

Overall, the book is quite fast paced and very engaging. Andrew paints a vivid picture of his early life and of key moments in his journey to ‘more-than-enough’. He brings out his own shortcomings and naïveté through the process. Every chapter has some insight and learning for the reader.

The book falters a bit in the last chapter when it becomes prescriptive on what one should do when they have ‘more-than-enough’. Maybe that’s because one is not in the shoes of Andrew Wilkinson or maybe one has different views of these matters.

But let that not take away from an absolutely delightful read for people in the world of business, finance or otherwise.
Profile Image for Zach Witzig.
47 reviews
July 23, 2024
Category: Business - 4/5

Overall: 3/5

I have followed Andrew Wilkinson on twitter for a long time and have greatly admired his business insights and thoughts. His book is a self-bio on lessons learned from his insane business career and the realization that, despite becoming a billionaire, money cant solve happiness or fulfillment.

This was a good book for me to read, as the way he approaches his business career is often how I think I would like my own career to be. But, similar to a lot of other books Ive read in the last two years about great business people, it seems very challenging to get both a great family and social life, and a great and successful business life. There seems to only be room for 1 or the other!

I do like his philosophy of organizing your life not just around the things you love, but also specifically avoiding things you hate as well. Doing everything you can to optimize and build around both of those things.
Profile Image for Santhosh Guru.
181 reviews52 followers
August 30, 2024
Money is a funny thing. The skills needed to make it, grow it, and spend it are entirely different, yet we're mostly taught to work hard/smart and hustle to earn it. Once you start making money, you learn about growing it through investments/savings. blah blah. But we're rarely taught how to spend it, other than receiving generic advice like "be frugal" and "don't spend beyond your means."

When it comes to spending, I often find myself deep in Internet rabbit holes, exploring how wealthy people manage and spend their money. Andrew Wilkinson is one such figure I've frequently encountered in the podcast circles of Shaan Puri, Tim Ferriss, Ramit Sethi, Sam Parr, and others. Curious about his story, I picked up this book, and it turned out to be a damn good read.

Andrew has rubbed shoulders with some of my favourites, like Charlie Munger, Warren Buffett, and Derek Sivers. The book is well-produced, with a smooth narrative, the right hooks, and a tone of authenticity and groundedness. I sense that the real truth lies between the lines, in what’s left unspoken. For example, the book doesn’t delve much into his divorce, the perspectives of his critics or any flaws. Narrative fallacy is an in-built feature of memoirs, so we must trust our taste and intuition to make sense of what's presented.

Knowing all these, I still found the book interesting and enjoyable. Your mileage may vary, but if you enjoy business-related stories and memoirs, try it.
Profile Image for Amit.
243 reviews7 followers
September 9, 2024
I just happend to accidentally meet this book and not sure what made me buy it. The story from the title and the blurb sounded too sensational.

I am so glad I came across this book. Andrew has been open , quite honest ( a little more than many ) and very vulnerable, about his journey. You can see all shades of him being hardworking, risk taking, big bets. Tough times, being stupid , jealousy , anger and even when he was a prick and you hate him for his actions .

A story worthy of your time and will make you think and reflect on your journey. His success is real and so are his failures and insecurities. Personally Andrew is one of those people who I would like to meet someday and have a conversation with . I enjoyed the read.
Profile Image for CatReader.
1,032 reviews178 followers
September 24, 2024
Andrew Wilkinson (b. 1985-6) is a Canadian businessman and former billionaire now in his "wealth redistribution" phase. His memoir Never Enough tells about how he got his start in business founding many startups, failing a lot, succeeding massively sometimes, getting screwed over a few times, and being stupid with how he spent money and treated important people in his life a lot of other times. Unlike the subtitle's assertion, the "barista" stage of his career was quite short; by Wilkinson's early 20s he was already a startup founder making bank, and could have been set for life if he had made better financial choices and had clearer priorities then. Wilkinson narrates his tale with blustery bravado usually akin to the most egotistical contestants and shark investors on the Shark Tank franchise before coming to the realization in his mid-30s and after divorcing his first wife that money isn't, in fact, the end-all-be-all, and that the more one inflates their lifestyle, the more money and frustration it takes to sustain it (basically, "mo money, mo problems"). In the end, he discovers Peter Singer's effective altruism (because it went so well for Sam Bankman-Fried) and claims he's a reformed billionaire now. We'll see if it sticks or not. For any fellow MBTI aficionados here, this book reads like a classic ENTJ character arc reaching a midlife crisis point of discovering their feelings.

Further reading:
Richer, Wiser, Happier: How the World's Greatest Investors Win in Markets and Life by William Green
The Millionaire Next Door: The Surprising Secrets of America's Wealthy by Thomas Stanley and William Danko
Millionaire Women Next Door: The Many Journeys of Successful American Businesswomen by Thomas Stanley

My statistics:
Book 220 for 2024
Book 1823 cumulatively
Profile Image for Maartenbron.
18 reviews1 follower
December 18, 2024
I love a good founder story, and Never Enough didn't disappoint. Some points resonated, like him being one of the first to create Shopify themes. I bought these before and use Shopify daily.

The part about billionaire competition really stuck with me. On a fundraising tour, he met millionaires unhappy because their house was smaller than their neighbor’s, and billionaires comparing themselves to Jeff Bezos. All unhappy, with not the slightest bit of satisfaction. We all have a bit of “mimetic desire,” but it’s also good to “look down” and appreciate how far you’ve come.

What I appreciated most was how he later rewarded his early team. Back then, choosing a slightly bigger paycheck over equity made sense—none of them could have known the company would file for IPO years later. But after reflecting on his own wealth, he made a list, went back and gave them life-changing money. He didn't have to, so that stood out.

Honest book with the struggles and good reflection.
Profile Image for Colton Davie.
101 reviews
Read
July 9, 2024
Reasonably enjoyable!

Digestible chapters. Was nice seeing how the company morphed and what happened as second order effects within Andrew’s life.

Kabuki was revealing for acquisition and earnouts at negotiation.

A large portion of the book showed the importance of integrity.

Player, coach, owners box
Beer tastes the same
financing first acquisition
7 reviews
September 21, 2024
I was very disappointed in this book. Most of it is a humble-brag:
•”I know Charlie Munger, Bill Ackman, and Warren Buffett”
•”I have it all; don’t you wish you were me?”
•”I bought my poor dad an airplane.”
•Yada yada yada

At the end of it all, he’s just like them; divorces his wife, gets a hot new girlfriend, has a jet and 4 houses, etc

Then, his new buddy Warren Buffett talks him into giving it all away, so we’re all supposed to now worship him.

Couldn’t wait for this book to end.
This entire review has been hidden because of spoilers.
Profile Image for Daniel Hageman.
368 reviews52 followers
April 3, 2025
Unless you have a keen interest in the life and becomings of Andrew Wilkinson, or are very interested in anecdotal experiences of entrepreneurship wins and losses, I didn't find a whole lot to connect to in this book. There were small bits and pieces that touched on the psychology of wealth, upsides and downsides it can have on one's life, and less-that-fleshed out ideas of what it means to be ethical when one's net worth becomes atypically inflated, but nothing that requires a full book to understand and/or appreciate.
2 reviews
November 19, 2024
Didn't love it. A lot of bland anecdotes about meeting famous business people, figuring out how to make a lot of money without sharing much of the details, getting really wealthy really quickly, deciding the love of money was gross, giving money away, and then it's over. One mild takeaway was that the pursuit of money for money's sake is not healthy or rewarding.
3 reviews
May 21, 2025
Self-congratulatory story disguised as a cautionary tale. The author says he's learned how there's more to life than work / success, then spends the whole book humble-bragging about how rich and successful he is.
I dont understand why this book has 4 stars and I would not recommend it
Profile Image for Eriq Beoku-Betts.
52 reviews1 follower
November 12, 2025
Audiobook: episode 2 of my billionaire memoir arc. Though, I believe that wealth inequality is getting out of control, I also want to have a long successful career in business. These two ideologies seem to be in opposition.

I started reading these memoirs of hyper-successful people to help satisfy this dichotomy. Is this level of success achievable while still maintaining a fulfilling personal life? Are all billionaires greedy psychopaths who are willing to do anything to get rich? This book has been very influential in helping answer these questions.

The common theme between the two memoirs i’ve read (Wilkinson and Caudwell) is they both started doing business in their late teens/early 20s and as they started becoming successful their personal live suffered drastically. My theory is that because they spent so much time working, they didn’t have much opportunity to develop themselves which may have lead to the issues they had in their personal lives. Both success and personal life need to be nurtured, if you go for one at the expense of the other then the neglected one will suffer.

Perhaps you believe that somebody who sacrifices their personal life is a psychopath. I would argue, after reading this, that this is not the case. From what I could tell, Wilkinson is a mostly normal person who stumbled into success. Right place, right time. And though he did spend his money selfishly, he was mostly driven by the same things most people are i.e to escape anxiety around money.

But I didn’t give this a 5 because it gave insight to the two questions I posed earlier. I gave it 5 because of how it frames business and money as tools to help people and solve problems. Pursuing things selfishly is not the optimal strategy nor is chasing hyper-success for successes sake. This frame is pivotal. I want to be the kind of entrepreneur that makes things better for everyone i’m involved with and I do not have to sacrifice integrity to do so. This is a key piece to my thinking I want to take moving forward.
Profile Image for Curran Van Waarde.
9 reviews2 followers
August 19, 2024
Well written, entertaining and vulnerable memoir - it made me reflect quite a bit on my underlying motivations for pursuing wealth. It also served as a good reminder that money doesn’t solve all problems and can often make life a lot more complicated.

Andrew delicately balances the joys of business and investing, offering valuable insights into the fulfillment they can bring while carefully warning against the pursuit of money for its own sake.
5 reviews1 follower
October 1, 2025
Amazing book. Not sure if I ever finished a book in 5 days, but could not stop reading this one.
I now feel even more energized to work on my own projects and myself, while in the process improve the world around me.
26 reviews
September 7, 2024
It was a good memoir-style book with a couple business tips. For the most part it’s an enjoyable read. But felt out of touch when he described the woes of being a multi-millionaire.
Profile Image for ND.
34 reviews1 follower
September 10, 2024
“How much is enough?”

As a fellow Buffett-ist and Munger-ite (😆😭), I’ve followed Andrew and Tiny for some time now. But this much more personal and intimate perspective of the man. Andrew lays it all out. His insecurities, trauma, fears. Everything. And within him i think you’ll find a reflection yourself. Maybe you find peace in the message, maybe youll see turmoil.

While personally i think id already came to much of the revelations dished in the book by the time of reading it, it still is an entertaining read, as you follow andrew on his adventures of building to more zeros behind his name.

Much in line with other books like ‘Private Equity’ by Sun, ‘The Trading Game: A Confession’ by Stevenson or ‘The Counting House’ by Sernovitz.
140 reviews16 followers
April 24, 2025
An enjoyable memoir about a self-made billionaire and his journey of ambition and fulfillment. Fun quick read.
Profile Image for Lwazi Bangani.
87 reviews9 followers
December 13, 2024
This is an incredibly relatable and thought-provoking read that speaks to the modern struggle of chasing "more" while trying to find balance in life. As I turned the pages, I found myself nodding in agreement and occasionally pausing to reflect on my own experiences.

Wilkinson’s candid storytelling and vulnerability make the book feel like a conversation with a friend who gets it—someone who has been through the highs and lows of ambition, success, and the elusive quest for contentment. The narrative isn’t just insightful; it’s refreshingly honest, filled with moments that make you feel seen.

What sets this book apart is its ability to resonate on such a personal level without feeling preachy or formulaic. It’s not a guide to perfection but a reminder that life is often messy, and that’s okay. For anyone who has ever felt like their achievements are never enough, this book offers a comforting yet eye-opening perspective.

I truly enjoyed the read—both for its relatability and the gentle push it gave me to rethink my priorities. Never Enough is more than a book; it’s a mirror reflecting the realities of modern life, leaving you inspired to seek balance and fulfillment.
Profile Image for Sebastiaan.
108 reviews
February 28, 2025
Werd mij door ik-weet-niet-meer-wie aangeraden als een atypisch managementboek en dat ik dit, ongeacht mijn kolossale scepsis voor het genre, toch eens moest proberen.

Het boek is ok geschreven, bevat voor ondernemers ongetwijfeld hier en daar een handige tip, maar tegelijk lijdt het ook aan alle symptomen die ik in de rest van het genre aantref: Jezus Christus, moet je miljardair of succesvol antreprenoer zijn om sommige van deze openbaringen mee te maken of interessant te vinden?

Ik denk oprecht dat Andrew Wilkinson een fijne mens is, fijner dan veel van de sociopaten die hij ontmoet en beschrijft doorheen zijn carrière. Ik denk zelfs dat de centrale boodschap van het boek gebracht is op een manier die zeer welvarende mensen kan doen nadenken over hoe ze moeten omgaan met die welvaart. Maar uiteindelijk maakt Wilkinson duidelijk dat hij zijn lessen moest krijgen, enerzijds uit een ander boek, één van Peter Singer, en anderzijds van zijn working-class vriendin.

Rijke mensen kijken steeds naar nog rijkere mensen en zijn niet gelukkiger dan andere mensen. Zo, dat bespaart u alweer een luchthavenboekenwinkelaankoop.
Profile Image for Emma.
112 reviews10 followers
May 5, 2025
I never heard of Andrew before reading this book. The premise sounded interesting - self made billionaire realizes he’s tired of chasing money for moneys sake, advocates philanthropy and luxury minimalism. Cool journey, but I found the individual chapters (especially the early ones) hard to get into because I didn’t know anything about his companies or business partners. I found myself trying to Google for additional context or back story, especially with partners you have a bad feeling about as they’re introduced but then wait a few chapters to find out if you’re right. I had this on digital loan from the library and it expired 3x before I finally finished it.
Profile Image for Ajita Gupta.
100 reviews
March 11, 2025
I am a rather dissapointed with this book. The main theme is that abundance of money doesn't give you more happiness. The threshold, Andrew suggests, is reached at 50 Mio. And from then onwards its a downhill ride. The book is choke full of details of Andrew's work life, which seems even more messy than mine's since he is juggling dozens of companies at once. I'm not interested in the details. I picked up this book to learn about business lessons and findings. Sigh!
Profile Image for Devin Martin.
46 reviews4 followers
September 25, 2024
I appreciate the general arc of his journey, from insecurity and superficiality to basic self reflection and a hint of morality, but mostly it is an ego stroking humble brag.
Profile Image for Jenna Lindman.
83 reviews
February 17, 2025
First of all, Andrew, you’re welcome for letting you live in my head for about six hours. The story was enjoyable. I’m giving this five stars, I always find it difficult to rank someone’s personal experience so my default tends to be a five for memoirs.

I did not know who Andrew Wilkinson was or his company prior to reading this. I saw the title “Never Enough”, and thought to myself, “Well that’s how I feel most of the time so let’s give it a go.” I’m glad I gave it a listen!

It was interesting to get a view into the life of a successful business person, one who built themselves and into a billionaire. I felt that this person was talking in their authentic voice, and it was unpretentious for the most part. I enjoyed hearing about the failures and the successes throughout this Andrew‘s career. What was particularly fun about this story is that individuals running businesses don’t have all the answers, and they’re mostly just figuring it out as they go and staying open to opportunities as they arrive.

The part that was most interesting to me was hearing Andrew realize that life, success, and money is a mountain with no summit. This is something that I come to realize over and over again in my own life. There’s always something new I need to pursue. I can’t be satisfied. I always need to do the next thing and have trouble sitting still. But it’s interesting how this does not manifest as a pursuit of money for me, but more of a pursuit of learning and trying new things. Andrew‘s version of “never enough” is never enough money, where my version of “never enough” comes from more of a place of intrinsic value.

The one criticism that I have of this author is that he didn’t bother to pay off his parent’s mortgages until he signed the giving pledge at the end of this story. That really blew my mind. If you had all of these resources for over a decade, why isn’t that something you did sooner instead of buying houses you weren’t living in and ridiculously expensive excursions on yachts? I share everything I have with the ones that I love. And I still have plenty.

Overall, I really enjoyed the story and I’m interested to see what this person does next with their philanthropic pursuits.
Profile Image for David Edgar.
40 reviews
September 13, 2024
A straight-up traditional biography of Andrew's life so far. There are a few chapters on his childhood and education, but most of the book details his various business failures and successes. There isn't much business or financial advice, but the book's central theme is the pursuit of more. More for the sake of it and having got more, what to do with it? And why did he get more? And is it morally wrong to have more? And how much more is enough?

It's a great read. Andrew comes across as a nice guy, even if he is a billionaire.
22 reviews
October 5, 2024
I’ve been following Andrew’s success ever since he spoke at a Uvic business panel in 2019. As I’ve followed along I always liked his no nonsense approach to talking about business- it’s amazing how much fluff dominates the content of a lot of “business experts”. I enjoyed the honest account of his experience risking a lot, getting super rich, and grappling with the emptiness that comes with a money hungry lifestyle.
Displaying 1 - 30 of 295 reviews

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