airbnb entrepreneur

What it feels like to be in the top 5% tax bracket

How long does it take to get to the top 5% tax bracket?

I’ve cleared close to $300k from Airbnb and another $200k from my blog in 2019. It was the most amount of money I’ve ever made in my 30 years living on this planet.

What I realized is that, it isn’t worth the “hype.” I had doubled my income roughly every year or so… while this is a great achievement and fiscally it is, but then why do I feel a sense of lacking?

The first book that changed my life was Tim Ferriss’ 4-hour workweek. I modeled my lifestyle and businesses thanks to that book. And it taught me how to maximize my per-hour output.

It taught me that my time is non-renewable. It taught me to value my time more than money. And I took this to heart and built my company to mimic what Tim calls “automation.”

Yet, there were mornings that I’d wake up anxious. There were mornings I’d wake up questioning everything… What was the point of earning more “money” if I couldn’t learn how to enjoy it?

And yes, most of the Americans (95%) earned less than me and I’m here “complaining” about my suffering. I could just see one of your thought bubbles go: “Poor Sam, you made $500k last year and you’re telling me what it feels like when I’m making $70k a year?”

I get it.

I may look like I’m complaining to you, but I also want to give you some insights into my journey in the last 3.5 years.

The last 3 years as an Airbnb Entrepreneur to get to the top 5% tax bracket

top 5% tax bracket
Where does it end?

It took me more than 3 years to earn ~$500k and I doubled it every year. 3 years is a very short amount of time, but it was still hard work, very hard work.

There’s nothing that will replace hard work.

Our society today wants everything instantaneously and capitalism drives for more and more at the expense of overconsumption. Do I really need another pair of shoes? Do I really need another unit or 10 to make me happy? Do I really need 1,000 paying students?

Of course, these are the very things that I am guilty of as well. I fell into the prey of capitalism and overconsumption.

In my darkest times, I used to think I’m doing this for the people that I employ. I used to think that I did it for my students because I have helped change many people’s lives. But that only kept me going and cheered me up for a bit.

It’s crazy to think 5 years ago, I was fired from my $75k corporate job, nice company perks, free lunches, almost-free healthcare, and a social circle.

What I miss the most was having people to talk to… it’s a lonely job starting a business (why don’t believe me? Start one and then write to me).

It would have taken me 10 years to make ~$400k in a traditional corporate world… If I had stayed in sales, went to Harvard or Standford for an MBA, got promoted to C-suite; I’d have made around $300~350k.

I just turned 30. It’s a number that I never thought I’d become. And here it is, staring at me.

Read more: Why I’m not your Airbnb Guru.

And now that I’m 30, what did I learn about myself (even at the top 5% tax bracket)?

My mother taught me “Money” is the most important thing in the world. She loves money and her enthusiasm for money has somewhat been transfered to me.

I knew from a young age that I valued money and it only took me 30 years to figure out that I didn’t love money.

I believe the true way to live is through careful examination of internal beliefs and define your own definition of a “good” life. It wasn’t easy for me to realize that my own misery was caused by my ambition to make more “money.” I become a salve to my ambitions.

When I was making $40k right out of college, I wondered what making $75k a year was like. When I first started my business, I was wondering what $100k would feel like. $200k…?$300k…?$500k…?

I could always go chase a bigger financial goal. That was the precise trap that I was in. I never took the time to look back and appreciate the work that I’ve done. I never took a second to slow down and just “be.”

I’m not an extravagant individual- and I’ve only flown once in business class.

Yes, the champagne upon arrival was great. Yes, the attentive service was nice. They treat you like royalty. And yes, the space to spread out my legs was also nice.

If you been in business class once, you’ve been in them all.

top 5% tax bracket

What did that teach me about myself?

My lifestyle isn’t that expensive so why do I constantly want more?

“I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it’s not the answer.”

Jim Carrey Actor

This is to say, you should strive to get rich so that one day, you can come to realize it is not the answer.

My happiness stayed the same when I was making $120k a year. I was affluent I didn’t have to worry about picking up the tab for bottle services or worry about a nice meal out with my girlfriend, or my recent experience at Maido (top 50 restaurants in the world) where I spent over $800 on a single meal.

Yes, I live a good life and there’s no doubt that money can buy that. It buys you access to things, places, and people. And at the end of the day, my internal happiness is what I must work on.

I know people who make millions but are miserable. I know a friend who is an heiress to a $100m trust fund but is torturing herself with one of the most stressful professions in the world (law).

Why do they have to punish themselves like this? For what? And why do I want to make $1m? Just to brag to my friends and family? “Hey!! Look at me, I’m in the big boys league now!!??”

All that wasted energy and effort spent proving to people that I am “worthy” of their respect and love when I, myself, didn’t love me from the start?

Are happy people just as ambitious?

top 5% tax bracket

I often wondered if happy people are as ambitious in striving to achieve material success as unhappy people.

And at what point, does greed take over your soul? And before you become single-handedly focused on making money and spend your entire life “achieving” a moving-target of “more is better.”

Imagine you’re dying and out suddenly, a genie pops out of nowhere and grants you a wish. But it’ll cost you.

What would you pay for 1 year’s worth of time? What would you pay for a chance to say goodbyes to your loved ones?

All the money in your bank account? Unfortunately, that genie doesn’t exist. And you can’t buy back time even if you’re a multi-billionaire (maybe in 100 years when we’ve figured out how to slow down death).

Again, I’m not saying to not go for your financial goals. I’m only cautioning you against “more” because at the end of the day, being “rich” is not what you think it is.

Read more: Why I didn’t create a 7-figure Airbnb business.

Did I mention it’s a lonely job to get to the top 5% tax bracket?

I can’t talk to my friends about my struggles because most of them haven’t experienced what it’s like to start a business, let alone two separate businesses in two different industries.

I can’t talk to my mom about my wealth because she’s always asking “what next?” “How much more are you going to make this year?”

The only person I can talk to is my significant other, who sits and listens with an empathetic ear. While that is all I need most of the time, but she doesn’t truly understand my pain.

I had to redefine my “American Dream.” This one, I made it.

And I end this with a question, “what is your version of the American Dream?” Think about it before it’s too late. Are you sure you want to get to the top 5% tax bracket?

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