Top 5 Financial Lessons: From 9 Figure Humans.

And why I'm super bearish on traditional "education" and bullish on micro-schooling.

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Our Education System Ain’t Doing So Well…

My heart hurts for the youth of America.

The youth who’ve been systematically lied to and exploited by our education system. My heart hurts for us “adults” who just now are realizing there has to be a better way.

The question is really; what we are going to do about it?

It’s not very helpful for me to rant, instead of sharing the lessons I WISH school had taught us and the very things that may bring that to fruition. Rant + solutions.

So today:

The Decentralization of Education: De-Ed

We live at the meeting of two bulls about to collide. At one end there is NO better time to be alive; technology, innovation, opportunity, decentralization, the democratization of everything. But at the other more sinister end, college and perhaps all schooling, has never been more expensive and less useful.

These are the stories of our education system:

  • The average US student has $30,300 in college debt for a grand total of $1.7T

  • One member of my team is a rockstar, went to college, pursued an MBA, and promptly amassed more than $150k in debt. It hasn’t translated to salary increases and instead has loomed over (but we’re fixing that!).

  • I could go on here ad nauseam but…

There is a new trend emerging.

Decentralization. Just like with blockchain, de-fi (decentralized finance) and decentralized working (aka remote work), will our education system also no longer be controlled solely by a single entity?

Some call this unschooling….

The Rich Are Voting With Their Feet (AND EARLY)

I sat with a very high net worth friend at dinner. He has done very well in real estate, time and again. He’s thoughtful, incredibly charitable and the kind of adult I hope to grow up to be. He said something that surprised me. He and his wife now add to their quarterly check-in on financials, their marriage, their health and their family, one question:

“Do we still think our school serves our children?”

For right now the answer is, “Yes, kind of.” But they aren’t so sure moving forward. Turns out, this movement is growing among the wealthy and the not alike.

Caveat, I don’t have children.

My mother was a special education teacher for 30 years in public school, I went to public school (until my grad degree), I turned out ok (highly debatable). But I started poking around because a shift is happening. Homeschooling is growing (5x more parents interested in 2021 than 2020 or 2019), and not necessarily because parents have to do so with Covid.


  • Institutional trust is falling

  • Online education is faster, arguably better, with quicker feedback loops

  • Smartphones and computers are cheaper than ever

  • Apparently, parents don’t love the idea of their kid (if acting out) getting arrested at 12

  • Customization is possible - no one size fits all with 30 other kids

  • Credentialization is less important than skill stacking

Also - when you’re wealthy, there’s one thing you really don’t like: getting told what to do, especially when it doesn’t make sense, especially when it’s about your kids.

Historically people didn’t homeschool because, homeschooled kids were weirdos, (I jest - kinda). But also because:

But today there’s a change in the air.

My prediction: Homeschooling won’t stick…

Let’s be honest.

Have you been around children for any length of time? There’s a reason moms generally wear workout clothes all day, parenting is an extreme sport.

Homeschooling can be incredibly hard on the parents, also perhaps incredibly rewarding. But it’s a hell of a job with no pay, vacation, or resources.

What I believe will stick is micro-schooling and pods.

My bet is, groups of parents and communities will create almost trade-like schools for their children. They’ll exist outside the mandated curriculum and it’ll put a further divide between those who learn how to memorize and those who learn how to learn.

That’s how Kaleena Amuchastegui teaches her children, right alongside a 35,000 person community all interested in non-traditional schooling.

Perhaps in the future, there will be micro-schools and pods w/:

  • A pod for entrepreneurship

  • A pooling of resources for coding tutors

  • A grouping for travel split between which parents take them

  • An allowance to homeschool students for business and work creations

  • Maybe even a “WeSchool” model where students can go, school remotely with others, tracked on tech, and with optional engagements to participate in?

The top tier will increasingly self-create, or pay to create, highly customized schooling experiences that have nothing to do with what the government says students should learn.


When the government overprescribes education the problem is it all gets outdated fast, education stagnates, and yet since tax dollars are at work, the government adds more rules to “fix” it all.

Work slow, don’t break things, don’t innovate, doesn’t generally work.

So f*ck the traditional system. We’re going to do it the contrarian way.

Want to learn the nontraditional way —> join at Contrarian Cashflow.

Click Here

ContrarianU: What I Wish I Learned

I have this theory: we have to unlearn many things we were taught in school.⁣

Most don’t teach the real classes we should be taking.⁣

For instance, I worked on Wall Street, I went to a party school (ASU), then a top tier(ish) school (Georgetown), I got an MBA and Ph.D. (although my doctorate was in Brazil so mostly I majored in samba, cachaca, and bad decisions)..

AND YET, no one in all those big companies training programs and overpriced schools taught me these lessons. Who did? Over 8 years ago I volunteered to speak at my first mastermind event for a group of high-performing individuals. I walked in those hotel conference doors and the person who came out was never the same.

After I gave my spiel (about investing in the public markets) I sat and listened for two days. This group of 8 and 9 figure humans shared these lessons with me. They showed each other their net worths, shared how they won and lost fortunes, why they got married and divorced, how their businesses started and flopped and how each time they got back on their feet. There is no faster hack for 10,000 hours than getting to walk in another shoes.

If I was to start Unschooling, here’s where I’d begin:

#1 Negotiate Everything

Have you ever been to India, Mexico, China, or any developing country? You’ll notice prices are rarely listed and life is a giant game of persuasion. I first truly learned to negotiate from my Egyptian friend Kareem. We stood in a dingy alley in Shanghai, I pointed at an “off-market” purse I wanted, as I’m about to pull out my Yuans, he leaned down conspiratorially to me and winked, “Watch this.” For the next 20 minutes, I watched him smile, pretend walk away, and cajole a small Chinese woman into an eventual 200% off the purchase price I was going to pay. While I was sweating, averting eye contact, and generally just wishing I’d given the lady the money, by the end of his negotiation he and the lady were laughing and smiling while I mostly needed a shower.

The idea of negotiating with skill and grace is anathema to Americans. It is tied to narratives, You can’t afford it. You are cheap. How crass, asking for a discount? But the truth is, you will NEVER get what you don’t ask for.

So let’s start with, learning to negotiate every salary you are offered: including if applicable, higher salary, more vacation, better benefits, higher commission payout, revenue share.

The first 3 jobs I held out of college I didn’t negotiate. Turns out only 46% of men and 34% of women negotiate their salaries. Think about this, 86% of people who negotiate, get higher pay (in the realm of 11-20%).

Don’t be normal, it doesn’t pay. Negotiate: tools here.

#2 Get Ownership Early:

The way to create real wealth is through ownership and equity, not employment.⁣ The easiest way to start?

Turn yourself into a You-Corp. I wish I would have started to see the world earlier through the lens of a business owner. The second property you rent out is a business, with an LLC. The content you create online is a business, with expenses and profits. The pool of money you use to invest in Angellist can be a business.

Think like an owner…in all aspects of your life.

#3 Have Your Liabilities Pay for Themselves

We sat overlooking the slopes in a snow-lined ski village. The house was beautiful, the owner had plenty of cash to buy it with, and yet, he rented the house out on Airbnb for every day he wasn’t there. Why? How do you gain wealth? You try to keep more of what you make. I call this lifestyle arbitrage. Instead of paying for his house outright, now the house pays for itself.

If you have a second home why not rent it out when you aren’t using it? If you have a second car why not use Turo to rent it out when you’re on vacation.

If you are just starting out why not consider house hacking? Buying a place and renting out the extra rooms or a second part of a multi-family to roommates who pay your mortgage?

My goal - have my liabilities (cars, homes, boats whatever you have) pay for themselves. In our sharing economy today, that’s easier than ever.

#4 Have a Plan for Your Money… Or Someone Else Will

No one will care about your own finances as much as you do.

It’s Friday, my coffee is in my hand and I’m deep in… spreadsheets. Why? It’s Financial Friday, where I go over the finances of all my businesses. This includes a check on my own finances and an overview of all the investments. 

I, of course, stole this idea, as one is mandated to do for all good ideas :). My fiancee and I go over our personal finances with a spreadsheet that looks a lot like this (false data): (but if you sign up for Contrarian Cashflow you get a version).

I treat money as a game. Keep score.

#5 Get Nerdy: Learn About Taxes

Things like taxes and 1031 exchanges ain’t sexy, but they lead to wealth.⁣ Ask yourself these questions about taxes, and if you don’t have the answers here’s a good place to start figuring them out.

  1. How do taxes work on long-term capital gains vs income?

  2. Why CEO’s will take salaries of $1 and the rest in stock options?

  3. That it may be better to make $800k as a non-W2 employee with the ability to do write-offs than earn $1MM as a W2 employee?

  4. How do 1031 exchanges in real estate work?

  5. How about opportunity zones and how to use them?

And for all those people who use turbo-tax to do your own taxes, I’m so sorry to tell you, but you’ve probably missed tens of thousands (on the low end) over the years that a smart accountant could have saved you.⁣ I certainly did.

Want An Education?

You better go out and get it yourself. Because if you trust others to fill your head, you just may not like what ends up there.

If this resonated with you, and you want to create $10-100k in passive monthly income...

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