Matt Took 15 Years to Prepare for a Happy Retirement — He Reveals His Secret Sauce
My eyes opened wide

“I am not too terribly smart.”
Matt says that all the time.
It could be true. Real geniuses or high IQs are hard to find. But that shouldn’t stop us from designing the life we desire.
In the case of Matt — It is his retirement.
We got acquainted from my second job and remained friends until today.
We spoke a lot about a lot. And chiefly, on retirement.
- What do we want from our retirement?
- How can we solve the money problem?
- How do we get there?
We can go on forever.
And I’m happy for him.
Because he got there first.
An Ideal Retirement… 15 Years in the Making.
Does 15 years sound long?
I don’t know.
This is what I know. Matt’s plan is rock solid. He learned from his failures and perfected it.
These are his lessons or retirement takeaways.
- Start early,
- Invest with peace of mind,
- Manage a super simple business.
Really, that’s it.
It is simple, straightforward, and relatable.
The Retirement Journey Started Early
I didn’t [even] know Matt charted his retirement course for 15 years.
I found that out over a cup of coffee.
“I planned for my retirement since 30. I spoke to people I know and penciled down things I may continue beyond 50. Everyone thinks it is easy. Well, it is anything BUT easy.”
I endorse his line of thinking.
I have spoken to too many retirees. Successful ones. Failed ones. Those who remain retired. That who returned to the workforce.
Taking retirement for granted guarantees failure.
“I know we talk about retirement all the time, buddy. But what did you actually do?”
Matt’s answer revealed his depth of thinking [for the first time].
Make a List
“I don’t know what to do at the beginning also. You know that. We spoke a lot about it. So, I made a list. What I want to do and what I don’t. I started there.”
Actionable thoughts tend to be simple.
“I know I don’t want to be an employee forever. Cubicles annoy me. I want to be out there. But I don’t want to sell. I am too quiet for that. So, I searched for a middle ground.”
This is the hallmark of successful retirees I know. They are incredibly self-aware.
- They know who they are.
- They know who they are not.
- And they don’t force it.
This is just the beginning.
The 6-Digit Investing Journey Starts from… Bills
No retirees I know escaped this talk.
It showed me one thing.
Building an investment portfolio is part of the retirement process. Part of.
The easy part is knowing that we need one. The tough part? What goes in it.
Many [successful] retirees [I know] know what they want in their investment portfolio. Matt is no exception.
His epiphany comes from life. Not financial news. Not Wall Street.
“I don’t understand complex finance numbers. I approach the topic differently. I was clearing my bills one afternoon, and it hit me. These must be good businesses I am paying for. What not invest in them?”
Matt’s thinking was so simple — I doubted him.
“Really? Bills? That’s it?”
“Yes, that is it. These companies pay dividends, too. So, I bought them for years and years. I don’t know tech, but I know nationwide grocery chains, energy providers, and Apple smartphones. I buy what I know.”
Is this the ‘circle of competence’ idea put forward by Warren Buffett?
I think so.
Back to Matt’s List — On [Finally] Figuring Out What He Wants to Do
Matt manages 15 vending machines all around Singapore today.
Yes, vending machines.
He has vending machines selling,
- Drinks [standard stuff],
- Cup noodles and snacks [simple],
- Plush toys [the one with the giant claw],
- Flowers in a box [this one intrigued me],
- Pokemon cards and ‘huggables’ [I learned something new!].
Matt shared that he suffered big losses during the early years of vending machine leasing.
He started selling fresh orange juice in a cup. These are machines that squeeze oranges when payment is made. It was a disaster. The machines need to be cleaned daily.
Matt had to hire professionals to maintain his machines. It ate into his profits. Soon, he figured it was not worth his while.
He gave that idea up.
But he never gave up.
The second idea also flopped. It was fruits. Matt placed bananas and apples into the slots. Well… that was a disaster, too. The fruit vendors do not want their fruits returned.
Matt had bananas for breakfast and lunch.
And he was burning cash. And fast.
This time, he pivoted faster. He went ‘instant’. Cup noodles. 3-minute porridge bowls. Potato chips. M&Ms.
And he figured out where to place them. Co-working spaces.
This time, he experienced success.
“It took me 2 years of losses to finally get a profit. I was so happy. My idea works! So, after that success, I placed more instant-based vending machines into other co-working spaces to scale. It worked!”
He was smiling big.
I was happy for him, for sure.
And I started wondering… what have I been doing while he was testing his vending machine retirement business idea?
Of course, Matt did not stop there.
He ventured into the claw machine business. He placed them near nurseries, kindergartens, and junior schools. They are his latest cash cows.
“My goal is to own 30 machines before I hit 50. And then, I will start making plans to exit the workplace.”
The Close
Matt inspired me.
His thinking. His perseverance. His planning.
He showed me that retirement planning need not be complex. And he also demonstrated that execution of the retirement plan is the [real] killer.
It takes 15 years for his retirement plan to go on autopilot.
And now, it is time for us to answer this question.
“How many years will it take us to retire successfully? Are we ready to commit?”
Only we… have the answer.
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Oh, oh, you can buy me a cup of black too! Thank you!
