Think In Two Timelines If You Want To Build Greater Wealth
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If you want to grow your wealth faster than the average person, I suggest trying to think in two timelines that move together in unison. The first timeline is analyzing what's going on right now. The ...
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real estate
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June 20, 2025
01:18 PM
Financial Samurai
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If you want to grow your wealth faster than the average person, I suggest trying to think in two timelines that move together in unison
The first timeline is analyzing what's going on right now
The second timeline is analyzing what could happen in the future, with a consistent spread
It's having a dual computer cessor always running in your brain
I've been thinking in two timelines since 1999, when I got my first finance job out of college
Thinking this way was key to me building enough wealth to escape corporate America in 2012
I haven't stopped thinking this way since
Example Of Thinking In Two Timelines For Greater Wealth The classic example to explain my suggestion is to people who are currently working
Timeline #1: How do you feel your job now
Timeline #2: How do you think you will feel in ten years if you are still doing your same job today
Most people I talk to never think question two when they first start their job
They are thrilled to be there and full of optimism
But I want you to think question #2 because I'm trying to get you to forecast your misery
If you can apximate when you'll be miserable at your job, you can take steps to prepare for when that misery comes
But if you don't think question #2 consistently in two timelines, by the time you are miserable, you are screwed
You have little-to-no options for getting out of a suboptimal situation
Saving And Enough To Break Free From Misery When I was told I had to get in at 5:30 a
To ensure I got the appriate re from my colleagues in Asia for clients, I knew I couldn’t last 40 years in a career my parents did
Instead, I made a more realistic assessment: how long could I conceivably last before burning out completely
The answer I came up with was age 40
So I calculated how much I would need by then to have the courage to walk away
That number was $3 million
Depending on how the net worth was structured, it could generate potentially $100,000 a year in passive income
From that moment on, saving and $3 million became my mission
I constantly visualized what life would look at age 40, 41, 42, 43, 44, 45, and beyond—free from the grind with that money in mind
This two-timeline apach—present-day hustle paired with future-day dreaming—kept me focused and motivated
I truly believed that if I didn’t hit that net worth target, I might short-circuit my life from all the stress and hours
I was already beginning to suffer from plantar fasciitis, uncontrollable allergies, and weight gain
In the end, I left three months before my 35th birthday thanks to an unexpected variable: the ability to keep all my deferred compensation and receive a six-figure severance package after 11 years at my last firm
That severance covered five years of normal living expenses
With that financial cushion in hand, I knew it was now or never—so I took the leap of faith
Using Two Timelines To Become A Better Investor Now let’s apply my two-timeline apach to . 1) Present Timeline: Investors have done incredibly well since 2020, especially those who bet on
With the S&P 500 up more than 20% in both 2023 and 2024, the investor class has built far more wealth than expected
Real estate has also performed strongly since 2020, although some — Texas and Florida—are correcting
Every investor should look at what their net worth was in 2020 and celebrate
This trend is ly only going to continue 2) Future Timeline (10–20 Years Ahead): If you or your parents don’t invest aggressively, life could stay in hard mode indefinitely
The wealth gap has already widened dramatically since 2020, and it's ly to keep widening
In 10 to 20 years, buying a primary residence might be next to impossible
Finding a job that pays a livable wage could also become increasingly difficult as AI disrupts more industries
The Plan To Ensure The Future Will Be OK I’ve developed a general game plan to give my family a fighting chance to compete in an increasingly competitive and uncertain future. 1) Hold onto our primary residence and at least two rental perties to stay long real estate
Real estate is one of the most reliable ways to build and preserve wealth over time
By holding onto perty, we not only benefit from potential appreciation and rental income, but we also tect ourselves from being priced out of housing in the future
Owning one rental perty for each child is something you should consider. 2) Build two 529 plans that equal the current four-year cost of the most expensive university today
College tuition continues to rise faster than inflation, and there’s no sign of it slowing down
Fully funding 529 plans now ensures our kids will have the freedom to choose quality education without being burdened by debt—or burdening us
They will also have the option to attend the best college that accepts them. 3) Invest at least the gift tax limit every year in each child's custodial investment account and Roth IRAs
By consistently contributing early, we harness the power of compounding
The goal is to build a financial foundation that allows them to pursue careers they enjoy, not just ones that pay the bills or seemed “high ” by society. 4) Aim to invest at least $100,000 a year in risk assets for the next 20 years for ourselves
To combat inflation and maintain purchasing power, consistent in equities, venture capital, and other growth-oriented assets is critical
This aggressive apach is our hedge against stagnation and the rising cost of living
It won't be easy as a writer, but I'll somehow find a way through other activities. 5) Build $500,000 in private AI company exposure to hedge against a difficult job market in the future
AI is both a threat and an opportunity
By in private AI companies or funds, we aim to participate in the upside of nological disruption, rather than simply becoming victims of it
Why a $500,000 Investment in AI Makes Sense Ever since 2017, I’ve been grappling with the reality of having to pay for college starting in 2036
Based on current jections, we’re looking at around $450,000 for public and $750,000 for private university tuition over four years
That’s a staggering amount—especially considering most of what’s taught in school today is freely available online
One solution is to guide them toward attending community college for two years before transferring to an in-state university
Another is to educate them ourselves, or at least as much as we possibly can before they are adults
But perhaps the most compelling solution is to invest in the very nology that’s ly to disrupt traditional education the most: artificial intelligence
At first glance, allocating $500,000 to private AI investments may seem excessive
But when you compare that to the potential $450,000–$750,000 cost of college in 2036 for each kid, it starts to look a rational hedge
The logic goes: if I'm willing to spend $450,000 to $750,000 on college in 2036 per kid, then I should absolutely be willing to invest $500,000 or more in the very companies that might make traditional education obsolete
Heck, I should be willing to invest $900,000 – $1. 5 million in private AI companies now that I really think it
The Potential Returns On A $500,000 Investment Here’s a breakdown of how a $500,000 investment grows over 10 and 20 years at different compound annual growth rates (CAGR): Annual Return10 Years20 Years 5%$814,447$1,326,649 10%$1,296,871$3,363,748 15%$2,028,836$8,180,612 20%$3,094,972$19,123,616 25%$4,660,134$55,337,118 A $500,000 investment compounding at 15% annually over 20 years grows to $8
Can you imagine having the option to access that kind of capital in your mid-20s
While 15% is an aggressive target, these types of returns are far more plausible when in earlier-stage
Just look at the performance of early investors in OpenAI, Anduril, Scale AI, Databricks, and Anthropic—many have achieved well over 50% annual returns since their Series A rounds
Scale AI went from less than a $50 million valuation in 2017 to now $30 billion
That's a 153%+ compound annual return over nine years
As a private equity investor since 2006, I’ve had a number of multi-baggers across various funds
The real challenge, however, is having a large enough position in these winners to materially move the needle
The other challenge is not in too many bagels (100% losers) that drag down the overall performance
Not easy, but I'm willing to keep trying with up to 20% of my investable assets
Think in Two Timelines to Without Regret The present is fleeting, and the future is always on its way
To fully, we must learn to hold two timelines in mind: who we are today and who we want to become
It’s not enough to simply dream of a better future
We have to act in alignment with that vision every day
Otherwise, we risk drifting, only to wake up one day wondering where all the time went
And when that moment of reflection comes—when the noise fades and the days grow quiet—I hope we don’t look back with regret
Not for the risks we took or the failures we faced, but for the steps we never dared to take and the time we never prioritized
At 48, I know I’ll be deeply disappointed in myself if I don’t spend the next 10-20 years fully present with my children, prioritizing health over hustle, and resisting the relentless pull of more money and
I want to spend my time doing what fulfills me—not what others expect of me
Let’s today with tomorrow in mind
That’s how we give meaning to both
Suggestions If you're looking to invest in private AI companies, check out Fundrise Venture
The minimum investment is $10 and you can view what Fundrise is holding first before making an investment decision
I've personally invested $153,000 so far and I will continue to dollar cost average in to build my AI position to $500,000
Fundrise is a long-time sponsor of Financial Samurai as our views are aligned
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