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 like having a dual computer processor 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 about 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 about question two when they first start their job. They are thrilled to be there and full of optimism. But I want you to think about question #2 because I'm trying to get you to forecast your misery.
If you can approximate 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 about 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 Investing Enough To Break Free From Misery
When I was told I had to get in at 5:30 a.m. and stay past 7 p.m. to ensure I got the appropriate research from my colleagues in Asia for clients, I knew I couldn’t last 40 years in a career like 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 investing $3 million became my mission. I constantly visualized what life would look like at age 40, 41, 42, 43, 44, 45, and beyond—free from the grind with that money in mind.
This two-timeline approach—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 approach to investing.
1) Present Timeline:
Investors have done incredibly well since 2020, especially those who bet on tech. 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 markets—like Texas and Florida—are correcting. Every investor should look at what their net worth was in 2020 and celebrate.
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 likely 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.
What should we do?
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 properties to stay long real estate.
Real estate is one of the most reliable ways to build and preserve wealth over time. By holding onto property, we not only benefit from potential appreciation and rental income, but we also protect ourselves from being priced out of housing in the future. Owning one rental property 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.
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 status” 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 investing in equities, venture capital, and other growth-oriented assets is critical. This aggressive approach 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 investing in private AI companies or funds, we aim to participate in the upside of technological 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 projections, 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 technology that’s likely 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 like 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 about 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 Return | 10 Years | 20 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 about $8.2 million. 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 investing in earlier-stage private companies.
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 about $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 investing 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 Live Without Regret
The present is fleeting, and the future is always on its way. To live 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.
We will all grow old. 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 status. I want to spend my time doing what fulfills me—not what others expect of me.
Let’s live 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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I’m curious about your mixing up gift tax and kiss’s Roth IRA in the same sentence. Unless I’m mistaken Roth funds need to be earned by the kids themselves? Trying to learn more about this as I’ve got 3 boys, 1, 3 and 6 and as a middle school teacher I also pitch custodial Roth accounts to all my students.
Sure, the child needs to have earned income. Earned income is key for the child to contribute to the custodial Roth IRA. However, you can then gift / match the same amount of earned income, but it can’t total more than the max contribution, which is $7,000 for 2025.
Example:
Your child earns $3,000 from a part-time job in 2025.
The Roth IRA contribution limit in 2025 is $7,000 (under age 50).
You can gift your child up to $3,000 to contribute to a Roth IRA—even if they spend their own earnings on other things.
This is a great way for parents to kick-start long-term wealth building on their child’s behalf while also potentially teaching investing principles.
A few things to keep in mind:
The Roth IRA must be in the child’s name, not the parent’s.
If the child is a minor (under 18 or 21 depending on the state), it must be a custodial Roth IRA.
The parent (or another adult) acts as the custodian until the child reaches the age of majority.
Gifts count toward the annual gift tax exclusion ($19,000 per donor per recipient in 2025).
You can gift more than the child can contribute—but only the amount equal to their earned income can go into the Roth IRA for that year. The reality is, you can probably do whatever you want unless your brokerage electronically stops you from contributing after the limit. You just have to be OK with any potential penalties, which may or may not occur.
As always, speak to a licensed tax professional before making any decisions.
When our kids were born there was absolute horror amongst us parents about funding their college. Turned out we spent less the 100k on each (recent grads) to go to very good state universities – one in state and other out of state – and they immediately found good jobs. Not a small sum, and I remember it was about half that when they were about 10 years old and we were planning. But when we were planning it seemed a given that it would be 200k+ a year for each child. I don’t know, colleges have to survive too. They won’t have many students if the baseline is 450k per, unless the S&P maybe triples by then. I guess endowments can hold them for awhile.
Question on private investments. Can you profit before a company goes private? You keep writing about how these young private AI companies are increasing in value – but do you see actual return prior to going public? Isn’t that all funny money ‘valuation” as they are still using their actual cash (from you) to grow and are far from being cash flow positive? Or are their scenarios where they pay out to private investors when they are not yet public?
Financially, it was better to have kids earlier, when the cost of raising them and sending them to college was significantly lower. That said, the timing also depends on where you are in life and whether your income and wealth can outpace the rising cost of parenthood.
Personally, I’d rather plan for the worst—assume the highest costs and zero financial assistance—than be caught off guard. That’s the mindset I use when projecting my future timeline. With AI, times are changing for new graduates as entry-level jobs are getting harder to come by.
When it comes to non-tangible investments, like private equity or venture capital, it’s all “funny money” until a liquidity event happens—either a sale or a capital distribution. What you’ll find, if you invest consistently in private opportunities, is that after about 5–10 years, a steady stream of returns may start coming back. The key is being comfortable with illiquidity during those early years. I’m nearly 20 years in now, and that stream has become a reliable part of my financial picture.
But if you want liquidity, you can now invest in open-ended funds that offer liquidity. You don’t need to go the traditional VC route of being an LP in closed-end funds anymore, or as much.
For example, the Fundrise Innovation fund, an open-ended fund, holds a portion of its ~$200 million in assets in corporate bonds, which provides liquidity for anybody who wants to sell.
What did you do with the $100,000/kid savings from college?
I’ve been doing this a lot lately. At 45, I’ve been thinking about the 65-year old me. Based on how quickly 25 to 45 went, 45 to 65 will happen even faster. With that in mind, I re-focus on what can be accomplished in single days to make that guy proud and grateful.
I’m glad! Honestly, I’ll be so pissed at myself if I don’t spend the next 20 years fully present with my kids—if I choose chasing more money over time with family. It’s always a balance, but after 13 years without a day job, I’m convinced that most readers of Financial Samurai and similar sites will die with more than enough. Which means many of us are working and stressing far more than we need to.