Imagine becoming a billionaire in your mid-thirties. You accomplished the olympic gold medal of business. You did it without going to Harvard, Stanford or Yale. You never slept under your desk. You didn’t need to work 112 hours a week or raise capital from VCs.
Your motivation? The cashier at your local coffee shop says their payment system declined your debit card. That gut wrenching feeling of shame. You hate not having enough money.
But wait a minute. You’re a billionaire at 35 years old and you don’t grind anything but coffee? You didn’t follow the advice of hustle culture gurus, putting in 10X the amount of effort, working 112 hours a week? How did you do it?
Last week on Methods of Prosperity
Sam Zell acquired the Tribune Company’s portfolio in 2007. It included major newspapers like the Chicago Tribune and the LA Times. It included TV stations, and disjointed websites. Sam Zell saw potential in revitalizing the company. He tried this through an employee stock ownership plan (ESOP), making it employee-owned. He invested $315 million with his team. This deal offered tax advantages, but involved substantial debt. Tribune went bankrupt in a year. Zell received criticism. Management was challenging. Zell believed in his decision. The whole print industry underwent a drastic shift towards digital. Zell remained chairman during Tribune's bankruptcy until 2012. He passed away on May 18, 2023, with a net worth of over $5 billion.
The following is Methods of Prosperity newsletter number 86. It was originally deployed February 6, 2025. As of October 16, 2025, original subscribers have received up to Methods of Prosperity newsletter no. 122: Howard Marks.
Methods of Prosperity newsletter is intended to share ideas and build relationships.
86
Key Lessons:
Own assets which pay you passive income.
Lack of money is the root of all evil.
Solve your money problems.
Compare yourself to others.
Get rich for your family.
Envy can motivate you.
Model what works.
Have role models.
Be unreasonable.
Owning a home now costs $52K more per year than renting. Families are stuck as forever renters. We’re seizing this shift. Buying 100+ unit assets in growth markets.
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Sam Zell invested in newspapers during the emergence of the internet. He owned Tribune right at the decline of legacy print media. He acquired it for $8.2 billion in 2007. It went bankrupt in one year. He owed over $13 billion. Newspapers became obsolete. The internet brought down the cost of distributing information to near zero. Digital-first publications like BuzzFeed, Huffington Post, Gawker, and Gizmodo eclipsed Tribune. Craigslist offered free classified ads in every city. Newspapers went to zero profits overnight.
This newsletter examines what billionaires do right and what they do wrong. That presents an opportunity to model what works. If there’s any chance we can avoid the mistakes, isn’t that worth your attention?
Andrew Wilkinson would avoid acquiring businesses as fragile as newspapers. Which is fortunate, since he was close to becoming a journalist. A trait you’ll notice about him is that he paid attention to role models. Investors like Charlie Munger, Warren Buffett, Mohnish Pabrai and Bill Ackman. His first role model was Steve Jobs.
Andrew Wilkinson was born in Victoria, British Columbia, Canada in 1986. Shaughnessy is one of Vancouver’s most prestigious residential neighborhoods. It’s located in a central area of the city. That’s where he grew up. It was a financial stretch for his parents. His father worked as an architect. His mother was a homemaker who kept track of their finances. His parents prohibited Andrew and his brothers from playing video games. Their TV was limited. Cable was too expensive. His parents encouraged reading books. Andrew became desperate to play video games like his friends. The family had an old computer which he figured out how to install video games on.
Andrew hated doing chores and did anything to avoid them. He noticed how much time it took for one person to clear the table and wash the dishes. “What if we all just cleared our own plates, then stack them next to the sink?” He asked his parents. “It would be 30 seconds of work for everyone, but it would make this go much faster.” They laughed and refused, thinking he was only trying to get out of his responsibilities. That infuriated him. It made no sense. His assembly line would be much more efficient.
So far, there’s not one person who has earned over a billion dollars that remains employable. This is not a statistic I can put a number on. But the majority of individuals with a substantial net worth have this in common. They don’t like having a boss. Like Andrew, successful entrepreneurs notice inefficiencies. We’re compelled to do something about it.
“To this day, if anyone tells me what to do – no matter how reasonable – I will dig my heels in and resist.”
– Andrew Wilkinson
Growing up in an affluent neighborhood magnified the contrast. His family wasn’t poor, but they weren’t rich, either. His friends lived in bigger houses than his parents’ 3 story house in Shaughnessy. His friends had unlimited snacks. Their parents drove fancier cars and had maids to clean up after their kids’ trail of crumbs.
Andrew felt like an imposter among the rich kids. This feeling he describes as “other” than these more affluent families. It made money the biggest problem. That feeling of lack is torture. Lack of money is central to everything that is wrong. Lack of money is the root of all evil. Isn’t that a scripture from the New Testament?
It felt to Andrew that his family was doing it all wrong. It was harder than it needed to be. He had this nagging feeling that the other dads knew something that he didn’t. He had to figure out or else be poor when he grew up.
Financial disagreements are among the top causes of conflict in romantic partnerships. Lack of money is a significant source of tension for many couples and families. 31% of couples reported money as a major source of conflict in their relationship. This is according to one study. Another found that money-related conflicts constituted about 19% of disagreements. 45% argue about money on occasion, according to another study. 25% identify money as their greatest relationship challenge in that same study. For more data, there are women who report arguing “often” about money in marriage. They’re 3 times more likely to divorce. That’s compared to those who argued less about finances.
Financial pressure caused tension in Andrew’s family. His parents did the same thing over and over, getting the same results. There was no plan. His father didn’t have a pension. Andrew was his father’s retirement plan. That was scary.
You’ve heard of Rich Dad Poor Dad, the influential personal finance book by Robert Kiyosaki? The book tells the story of Kiyosaki growing up with two father figures. His biological father (poor dad) - well-educated but financially struggling. His friend's father (rich dad) - taught him valuable lessons about money and wealth creation. The book challenges conventional wisdom about personal finance. It advocates for financial education as a path to wealth creation.
Andrew had a similar “rich dad” figure. It was his friend Nick’s dad, a real estate developer. Nick’s dad drove a BMW, lived in a mansion, and had a roll of hundred dollar bills on him every day. He had plenty of time to make dinner, Hungarian schnitzel, for the boys. Why was Nick’s father not working late? Why was he wealthy? Why did he act like he was always on vacation? What did he know that Andrew’s father didn’t?
Andrew asked him questions over dinner and pieced together his story. He moved to Canada from Hungary with $140 in his pocket. After becoming a flight attendant, he saved up money and started renovating houses. Over a decade, he graduated from houses to condos, and built housing for thousands of people. He now owned a wide variety of real estate that earned passive income. His portfolio included strip malls, hotels, and residential. He became one of the most successful real estate developers in Vancouver. He was a millionaire. His biggest problem was boredom. He played online poker in his home office.
“So you don’t have to do much work day to day?” Andrew inquired, “The money just flows to you because you’re the owner?” Nick’s father’s name was André. He replied, “Exactly. My buildings work for me. I build them, but once they’re running, they’re like a machine. I just check in now and then.” This amazed Andrew. At that moment he vowed to crack the code. No more fights about money. He’d make everyone happy with vacations, toys, and schnitzel.
To be continued…
I like you,
– Sean Allen Fenn
PS: The purpose of wealth is freedom. You can have financial freedom, but not by yourself. That’s why we’re building our core group of people. It’s a community to help each other achieve financial freedom. One way is by pooling our resources to invest in Multifamily real estate together. Whatever method of prosperity you choose, don’t go at it alone. You can now join our Methods of Prosperity community on Telegram here:
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