“There’s no harm in asking.”
– Andrew Wilkinson
His tech reviews attracted attention. By day, Andrew Wilkinson was an awkward geek. On the internet, he was a big deal. MacTeens, the blog he ran with his friends, had become an authority. At 15 years old, his fledgling online empire gave him the confidence to ask for an interview with Steve Jobs. The Macworld Conference in New York is where Steve Jobs launched new Apple products. That summer, Andrew saved up enough money to attend. He sent an email to the PR team.
“I’m going to be at Macworld next week and was hoping to interview Steve,” he informed them, “Possible?” It was a bold move. Established media companies including Newsweek and The Wall Street Journal interviewed Steve Jobs. They never let kids with a blog do that. A few minutes later, he received a reply. “Steve’s schedule is too hectic, but I can get you in for a group tour of the new Apple Store in Soho?”
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Two men with similar opportunities and intelligence live in the same neighborhood. Only one becomes wealthy. Why? The middle-class man often struggles. Not unlike a pilot experiencing spatial disorientation. He makes small errors that lead to significant financial issues. Andrew’s parents had conflicting attitudes toward money. His father believed in bad luck. He had a habit of spending beyond their means, while his mother was frugal. His father knew about wealth-building, in theory. He taught his son about compound interest and entrepreneurship. Yet he remained constrained with his finances. Andrew became influenced by his father’s entrepreneurial encouragement. He started a consulting business at a young age, teaching senior citizens how to use Apple computers. He learned that business is about solving problems for others. As a teenager, Andrew took over a tech review website with his friends, MacTeens. Which gained popularity and received free tech products for reviews. His efforts led to media recognition. It led him to meet his idol, Steve Jobs.
The following is Methods of Prosperity newsletter number 88. It was originally deployed February 20, 2025. As of October 30, 2025,
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.
88
Key Lessons:
Show up at your appointed day and time.
Have the intention to get what you want.
Hard work doesn’t replace smart work.
What you tolerate you will experience.
You can always change your mind.
Give others a reason to let you in.
Get in proximity to the action.
Ask anything you desire.
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Notice what Andrew did there. He brought value to Apple by reviewing their products for his audience in advance. He had leverage, even though he was only 15 years old. He already planned to be there. He gave the PR team a reason to let him in. He didn’t ask for a tour of the Apple Store. That wasn’t a big enough ask. He asked to interview Steve Jobs. He asked for exactly what he wanted. Steve’s PR team compromised. Which placed Andrew where he intended to be.
Believing in yourself is only the beginning. Intention is the key. Feeling is the secret. Feeling mixed with determination. If you want to manifest the good which you desire, you must not only believe it. You feel it. Do more than visualize yourself there, in the place you desire to be. Ask for what you desire, believe you have received it, and you’ll get it. Andrew already made plans to attend Macworld. He saved up for it. He was going to be there with or without permission.
His father accompanied him to New York. Andrew paid for his father’s plane ticket. They showed up at the new Apple Store at the appointed day and time. It wasn’t yet open to the public. Located at a former U.S. Post Office on the corner of Prince and Greene Street in Soho, it’s an architectural marvel. With a floating glass staircase, there was nothing else like it at the time. Andrew and his father waited among other journalists. A black SUV pulled up. It was him. Wearing his uniform. A black mock turtleneck, jeans, New Balance sneakers, and circular rimless glasses.
“Hi, nice to meet you. I’m Steve,” the man said, looking Andrew in the eyes and shaking his hand. Steve Jobs continued to move through the crowd. Andrew followed him. In the next moment, Andrew was interviewing Steve Jobs.
“What was the inspiration for the design of the new iMac? Which one do you use, personally? How did you make this crazy glass staircase?”
Steve seemed amused. Andrew’s father watched his son’s dream come true. Camera crews from CNN, CNBC, and CBS surrounded them. More established reporters spent their whole working life in the same position. Journalists from Wall Street Journal, Time Magazine, and the New York Times. Yet here was this gangly kid in front of them talking to Steve Jobs.
After that, life reverted to normal. In between school and homework, Andrew continued to write tech product reviews. MacTeens generated ad revenue of hundreds of dollars a month. Andrew’s father resumed his spending habit, buying consumer goods he couldn’t afford. He brought home a large screen TV followed by a mid-1990s Saab 9000. His parents fought over their lack of cash to pay their debts. Andrew eavesdropped on their argument. That’s when he decided. He wouldn’t tolerate insufficient funds for his family.
Have you ever heard this theory? What you were doing in your teens is what you’re good at. It tends to be what you end up doing later in life, in some form or another. For example, if you are good at writing, chances are you will write a book. You might become an author.
Andrew graduated from high school in 2004. He told his partners at MacTeens he was going to college and gave them his quarter of the business. Interviewing Steve Jobs and writing Mac related reviews inspired Andrew. Journalism was the logical path to take. Upon enrolling at Ryerson University (now renamed Toronto Metropolitan University), it was disappointing. He realized he made a terrible mistake. Journalism was dying. Print newspapers had started to become obsolete. After a few months, he dropped out.
His parents were distraught. Their son was a college dropout with no plan. And now he moved back in. They couldn’t afford for him to live rent free. His parents turned into his landlords, charging him $500 a month for rent. When he ran out of savings, he had no other choice but to get a job or his landlords would evict him. That’s why he got a job as a barista at a local coffee shop in Victoria called Two Percent Jazz. Located next to the town newspaper where he imagined he would one day work, they roasted their own beans. Not the town newspaper, the coffee shop next door.
Some of his regular customers worked at the newspaper next door. They confirmed his decision to drop out of journalism school. The newspaper was struggling, laying off employees. Two of his regular customers, Jeff and Chris, sat at the espresso bar for hours with their laptops. They ran a small design agency, building websites for local businesses. Able to do 3 or 4 projects at once, they charged $5,000 to $10,000 per website. That’s $20,000 to $40,000 per month. Andrew was working hard, they were working smart.
To be continued…
I like you,
– Sean Allen Fenn
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