The Moment Your Portfolio Stops Feeling Fragile

Hi ,

There’s a moment every investor reaches, when their portfolio hits a magic number they had set their sights on long ago — and yet they still feel uneasy. 

I see it in entrepreneurs right after an exit, in tech leaders earning more than they ever imagined, even in seasoned investors. On paper, they’re doing everything right. But they suddenly realize their portfolio is built on noise and not an intentional plan. 

The noise is getting louder too.

Markets swing more. Headlines pull harder.  And every week seems to bring a new version of uncertainty.

Investors come to me with the same question, “Why does my wealth feel so unstable, while others around me seem more grounded?” 

I always explain what I’ve learned from building, buying, and investing over the years: the difference isn’t the assets themselves. It's the rhythm behind them. 

Most investors rely on allocation and timing the markets. Others build in cycles, layering exposure gradually and letting time do the heavy lifting – in other words, they invest in vintages.

The investors who build real, lasting wealth share one thing in common: their capital follows a pattern. They keep adding new positions across a range of private engines. They let these vintages mature at different points in time. They allow the structure to settle. And eventually, their portfolio stops whipping around like a carnival ride and becomes something they can gently uncork.

If wealth feels unpredictable, there is another way to build it. With time instead of turbulence.

You can pace it. You can layer it. And eventually, you can reach a point where the portfolio can support itself.

Here’s what you’ll find in this issue:

• SHIFT YOUR STACK: Why time-based pacing produces more stability and compounding than traditional allocation models.

• THE PORTFOLIO VINTAGE MODEL: Build Wealth’s interactive comparison tool showing potential returns across public and private markets.

• PLAYBOOK: A practical eight-year deployment plan to build a self-reinforcing vintage ladder across private engines.

Let’s dive in,

— Walker Deibel
WSJ & USA Today Bestselling Author of Buy Then Build
Founder, Build Wealth

SHIFT YOUR STACK

Time Beats Allocation

Public markets are priced for liquidity.
Private markets are designed for strength.

For decades, investors have been taught to manage portfolios through percentages. Set a target mix, rebalance occasionally, and trust the model. 

That works in theory, but the real world moves differently and if we are honest, chaotically. Modern portfolio theory has always pointed to something deeper: the real driver of long-term return isn’t the assets you chose, but the timing of how capital is deployed.

While many investors focus on allocation, the best performing portfolios focus on pacing. Pacing turns capital into a rhythm. That rhythm creates compounding.

And compounding builds wealth.

The Power of Illiquidity

Private equity has outperformed public equity across every major time horizon:

This gap is attributed to the fact that private markets are built on value-driven structures, not headlines. Public equity returns shift with timing risk, volatility, and investor behavior. Private markets don’t bend to liquidity pressure: they grow through operational value creation and disciplined deployment. This week’s report highlights this point clearly: public equity reflects timing risk and liquidity pressure, while private markets build exposure gradually across vintages.

Volatility is Telling the Real Story

In public markets, prices adjust instantly. Every headline becomes a swing in sentiment.

Private markets move on longer review cycles. This slower cadence protects the investor from emotional decision-making.

The full analysis compares public and private volatility across the shocks of 2008, 2020 and the inflation cycle of 2022–2023. The pattern is repeating and unmistakable: public markets spike whenever uncertainty rises, while private equity stays within a far narrower band.

This leads to a simple conclusion: volatility punishes public investors at exactly the wrong moments. Private investors avoid that stress entirely because compounding continues uninterrupted.

What Most Investors Miss

Most investors build portfolios around allocation targets. Private markets are built around vintages.

The public mindset says: choose a percentage for each asset and rebalance as needed.

The private approach says: spread capital across time. Each investment year becomes a vintage with its own cycle of creation, growth and harvest.

The advantage is subtle but powerful. Exposure is added steadily rather than all at once. Compounding stays active with each deployment. The result is a smoother experience and higher long-term outcomes.

If we compare the historical 20-year returns in the S&P with PE, the math is clear:

• A $1,000,000 investment in the stock market compounding at 9.7% becomes ~$6.4 million in twenty years. (Not bad!)

• A $100,000 annual "vintage" investment in the private markets for 10 years,  compounding at 15.2% should exceed ~$10 million by the end of year twenty.

Same invested dollars. Just just 50% more money (millions) to you!

When you follow a “vintages” strategy, you stop trying to predict the market. You create a rhythm of consistent deployment that grows stronger every year. Eventually, the portfolio begins to reinforce itself. Vintages mature. Distributions re-enter the system. Your next investments are funded by the ones that came before them.

That’s when the portfolio stops depending on public markets and starts behaving like a modern family office.

Dive into our extended analysis, including the full volatility maps, the private-vs-public game-theory models, and a detailed vintages pacing framework in this week’s report. Get the details of the complete structural logic behind why time-driven investing outperforms allocation.

Check out our weekly report: Private vs Public Game Theory HERE.

INTERACTIVE MODEL

Our Portfolio Vintage Predictor Tool Compares Public and Private Deployments

Here at Wealth Stack Weekly, we love models. 

They help us understand fundamentals, adjust assumptions and viscerally feel impact. For this week’s issue, we asked “How can we visualize the power of the private markets?”  To answer that, our partners at Build Wealth built us The Portfolio Vintage Model, an interactive web app that compares annual allocations in the stock market with what you can make with the same allocation in private markets. 

Try it out! You can adjust assumptions levers in real time and see the shift in outcomes. 

THE PLAYBOOK

The Vintage Ladder Leads to a Self-Sustaining Portfolio

Investing in private markets doesn’t allow for instant diversification like the stock market. Access to worthwhile deals is irregular, and minimums can be $50k to $100k or more. The Vintage Ladder fixes that by giving you an eight-year rhythm for deploying capital. As vintages mature, their distributions fund new commitments.  Over time, creating a portfolio that grows via its own momentum.

It might look like this:

Here’s how to build it.

1. Set Your Pace 

Pick a number you can deploy annually for eight consecutive years.

Two simple methods:

• A percentage of investable net worth, often five to ten percent

• A percentage of income, often ten to twenty percent

The exact amount isn’t as important as the ability to stay consistent.
The ladder works because capital enters on a reliable schedule.

2. Pick Your Private Engines

Your engines shape the rhythm of your ladder.

Choose 3-4 of them based on time horizon, cash flow needs, and long-term goals.

A clear starting point:

• Credit for shorter cycles and earlier liquidity

• Real estate for multi-year appreciation with income

• Energy for operational value creation in mid-length cycles

• Private equity or growth for longer arcs

Choose engines you understand and can revisit annually.

3. Build Your Ladder of Vintages

Create a simple grid with years across the top and your chosen engines down the side. Then map your plan for each year.

Here’s a common ladder:

• Credit - nearly every year, for ballast

• Real Estate - every 2-3 years, for cash flow and appreciation

• Energy - every 3 years, for tax efficient cash flow 

• Private Equity - every 2-3 years, for appreciation 

By the end of eight years, you’ll have built a complete set of vintages, each at a different point in its cycle. The structure creates natural diversification across time and strategy.

This doesn’t require large commitments. Deploying $50,000 a year builds eight vintages. That slow accumulation becomes the foundation of a durable private portfolio.

4. Track Pacing Through a Simple Dashboard

Shift your attention from percentages to pacing. Select or create a dashboard for a forward-looking view of how capital moves through time.

Keep track of:

• Which vintages are active

• When each is expected to mature

• Which engines deliver distributions in the coming years

• Where gaps appear in the ladder

• How returning capital supports future commitments

This gives you a view of the next decade rather than having knee-jerk reactions to short-term price moves.

5. Reach a Self-Funding Closed Loop by Year Eight

When the ladder is full, something important happens.
Distributions from earlier vintages can begin supporting new commitments.
Your portfolio starts covering part or all of your annual target.

This creates a closed loop.
You still guide it, but new capital becomes optional.
The structure itself produces the momentum.

This is the phase where private portfolios begin to feel steady and self-reinforcing. Wealth grows through process rather than reaction.

6. Review the Ladder Once a Year

A single annual review keeps your ladder aligned with your goals.

Ask three simple questions:

• Is the annual amount still appropriate?

• Should the mix of engines adjust based on strategy or personal priorities?

• How do upcoming distributions influence next year’s commitments?

Use it as a light annual reset that keeps your portfolio of vintages running smoothly.

WEALTH STACK REBELLION

“If everything you do needs to work on a three-year time horizon, you’re competing against a lot of people. If you’re willing to wait seven years, you’re competing against a fraction of them.”

-Jeff Bezos

The Advantage That Endures

Lasting wealth comes from a portfolio that follows a steady rhythm.
The investors who create real stability put new capital to work year after year, build exposure through vintages, and let time carry their results forward.

The world will always offer noise, urgency and endless reasons to react.
A paced approach creates distance from all of that chaos. It gives you room to focus on structure, on growing your base, and on the next small move that keeps the ladder intact.

It comes down to one shift: designing your wealth around time.

By building a sequence of commitments, you let compounding rise with every vintage added to the stack.

WHAT WE ARE READING

Game Theory Reinforces the Advantage of Private Market Investing

The Long Game: Why Private Markets May Thrive in Market Turmoil | AB

When Public Meets Private: The Strategic Role of Alternatives - Goldman Sachs Asset Management

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