Niccolò Machiavelli was an Italian Renaissance political philosopher. He argued that it was good for politicians to be deceitful because it made them more effective. This is the origin of Machiavellianism. It describes a personality trait deprived of principles. A Machiavellian personality is manipulative and cynical. He will attempt to get his way “by whatever means necessary”.
There’s a character from Roman poetry who fell in love with his own reflection. His name was Narcissus. The Roman poet Ovid popularized this tale in his work “Metamorphoses”. Ovid expanded on the earlier Greek versions of the story. Narcissism is the personality trait of vanity. A Narcissist carries a sense of self-superiority. She carries a sense of entitlement, dominance, and craves admiration and submission. People high in narcissism believe that they deserve more than anybody else. They believe they are better than everybody else.
Psychopathy is the personality trait of being low-empathy and high impulsivity. It is a persistent pattern of deviant behavior and a disregard for others. Psychopathy is the trait connected to criminal behavior.
Together, these 3 personality traits show up in the archetypical villain. Let’s call it the Dark Triad. The villain displays some combination of Machiavellian, Narcissist, and Psychopath. Work with other people long enough, and you will encounter this villain.
Last week on Methods of Prosperity
He went from barista to owner of the top interface design agency in North America. It had only been a few years. Andrew Wilkinson’s company, MetaLab, ran like a machine without him needing to be there. Then it generated half a million dollars.
He faced the typical pressures of entrepreneurship. This included financial risks, which led him to join a support network called Forum. This brought to his attention the need for financial oversight.
Andrew recruited Chris Sparling as CFO, who later became his partner. A partnership with Shopify led to the creation of Pixel Union. Which became a successful subsidiary selling digital themes, generating significant income.
Chris’ financial acumen complemented Andrew’s innovative spirit. They formed a strong business partnership. MetaLab was doing well. Things were great. That’s when the villain of the story was about to ruin it all.
The following is Methods of Prosperity newsletter number 93. It was originally deployed March 27, 2025. As of December 4, 2025, original subscribers have received up to Methods of Prosperity newsletter no. 129: Marc Andreessen.
Methods of Prosperity newsletter is intended to share ideas and build relationships. To become a billionaire, one must first be conditioned to think like a billionaire. To that agenda, this newsletter studies remarkable people in history who demonstrated what to do (and what not to do). Let me know how I can help you out. For more information about the author, please visit seanallenfenn.com/FAQ.
93.
Key Lessons:
Flattery will get you everywhere.
Bad people can do good work.
Recognize the Dark Triad.
Deception wears out.
Get incentives right.
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One day, a mutual friend introduced Andrew Wilkinson to Brian. “Hi, I’m Brian, and I’m a business addict.” He was a stylish, serial entrepreneur in his 50s. He used flattery well, often throwing around compliments. As much as he bragged about the businesses he started and exited for millions of dollars.
Brian exuded experience. He peppered his words with acronyms. ARR, ROI, ARPU, IRR, LTV, EBITDA. He used terms ubiquitous to LinkedIn, like synergy and disruption. He knew how to scale a business to tens of millions of dollars in revenue. He used metaphors including “put grandma on the roof”. That’s when grandma gets so old and fragile that you decide to kill her kindly. “You can’t just unceremoniously push her off your roof.” Brian continued with the psychotic metaphor. “First, you get grandma really comfortable and make her a lovely cup of tea inside the house. Then you tell her you want to give her a tour of the house. You walk her upstairs and say what a beautiful view on the deck. Let’s go look! Then, when grandma’s on the deck admiring the view, you push her off the roof.”
Brian helped Andrew sell Pixel Union. He proposed that he’d help sell it for a fee. Brian brought in a buyer named Bob. Bob’s family office would acquire Pixel Union for $7 million. The deal was that the buyer would pay $3 million up front. Then $2.5 million once the business doubles. Plus $1.5 million in stock. That worked out to $7 million in total, paid out over time.
Richard was Bob’s CEO. Liam, the former MetaLab intern, was CEO of Pixel Union. Richard believed Liam was too inexperienced. Richard wanted to replace Liam with one of his executives. Brian volunteered to take care of it. Liam would be grandma and Brian would push grandma off the roof. Brian infiltrated Liam’s environment, gaining his trust. He convinced Liam that he needed assistance. Brian recruited the executive that Richard wanted as COO. Then that executive usurped Liam.
After the Pixel Union deal, Brian convinced Andrew to compensate him for all the work he was doing. Instead of signing a contract or getting lawyers involved, he convinced Andrew to pay him by the hour. At $250 per hour, Brian did a great job. Which created a false sense of certainty that Andrew could trust Brian.
Brian suggested that MetaLab needed a new CEO to take over for Andrew. He reassured Andrew that he would find the right person for him. Brian lined up several candidates for the job. None of them fit the role. It was strange. Almost as if Brian chose them knowing they were awful. An old friend of Brian’s, named Alexander, brought them an offer to acquire MetaLab. Brian would take a fee as he did with the Pixel Union sale. He also offered to step in as interim CEO until MetaLab’s acquisition closed. Andrew was hesitant. Brian was a shark. Andrew and his business partner Chris agreed that it made sense to place Brian as interim CEO.
As interim CEO, Brian increased the business, promoting the work MetaLab did for Slack. He gained big clients. He doubled revenue. The private equity firm connected to Brian’s friend Alexander offered $50 million. It would take 2 years for this transaction, and it fell through. Brian remained CEO.
“There was something weird that happened last week,” Andrew’s brother said. Andrew’s brother worked for Brian at MetaLab. Brian instructed him to bribe a building inspector. If Brian was willing to bribe a building inspector, what other shady activity was he up to? Andrew lost sleep over the anxiety it caused, uncertain who he let run his company. The next day, a mutual friend informed Andrew that Brian was not a multi-millionaire. Brian made Andrew believe that he was. Andrew panicked and called Chris. In retrospect, things didn’t add up. It was like a horror movie when you find out who the killer is.
To be continued…
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– Sean Allen Fenn
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