
Exclusive insights into how high-earners think, invest, and build wealth.
Welcome to The Smart Portfolio, where each week, we share ultra-wealthy strategies, high-earner survey data, and real investment case studies.
In this issue:
Lessons from the way wealthy families invest
60/40 portfolios are too conservative, you could go up to 85/15 instead
Stocks vs Bonds: what asset allocation is right for YOU?
1. Lessons from the way wealthy families invest
Podcast: Capital Allocators with Ted Seides, Ep. 7 - CIO Greatest Hits with Jenny Heller at multi-family asset manager Brandywine (originally released in 2017)
Jenny Heller, CIO at Brandywine Trust Group, explains how a small set of ultra wealthy families invest. The big theme: when money is taxable and meant to last for kids and grandkids, you slow portfolio turnover, accept boredom, and obsess over process and taxes.
Key idea #1: Taxes can erase “good” decisions
If you sell a successful investment in a taxable account, you may be reinvesting only 60-75c on the dollar after taxes. That means the next idea must be far better just to catch up.
Implication: design your portfolio so you don’t need to trade much. Favor investment managers with low turnover and patient holding periods, or opportunities where you can keep patient capital compounding for years.
Key idea #2: Active vs passive, the practical way
They treat low-cost index funds as the hurdle. Any active manager (or other investment opportunity) must clear that hurdle net of fees and taxes. The internal test is simple: what breakeven alpha does this manager need, after tax, to beat an index held for years? If you can’t explain that in one sentence, you probably should not allocate.
Key idea #3: Private markets for the long haul
They like smaller, less competitive deals and long hold periods. The “buy a good business and keep it” idea works well for families with time and patience. For most investors who can’t do direct deals, the takeaway is still useful: avoid investments that require frequent exits to look good.
Some ideas to apply this in a taxable portfolio
Core: 60-90% in low cost index funds or direct indexing to harvest losses and control gains.
Only add active managers where the edge is clear and the manager’s behavior fits a long hold, low churn approach.
Private exposure: if you can’t access small, long hold deals, emulate the mindset in public markets by owning cash generative compounders for 5-10 years, not 5-10 months.
Bottom line
This is a masterclass in patience. Make fewer, better decisions. Let compounding work. Measure everything after fees and taxes. You will act less, earn more, and sleep better.

2. 60/40 portfolios are too conservative, you could go up to 85/15 instead
Podcast: The Long View (Morningstar), Ep. 336: Why Mean Reversion Means Your Portfolio Should Have More Stocks with Scott Bondurant (Sept. 9, 2025)
The 60/40 portfolio is an investment strategy that allocates 60% of its assets to stocks and 40% to bonds, aiming to balance growth potential from equities with the stability and income of fixed income. BUT because of stocks’ “mean reversion” this portfolio is too conservative and gives up too much upside without offering as much protection as you might think.
Stock returns “mean revert”
When stocks have a bad run, future returns tend to be better than average until things get back to normal. When they have a great run, future returns tend to cool. If you plan across decades, this pattern matters more than short-term noise. The punchline for retirement planning is counterintuitive: many investors should hold more stocks, not fewer, if they want to avoid running out of money.
What this means in practice
Own more equities for long goals. In the guest’s tests, an 85% stock and 15% cash/bonds mix with a 5% annual withdrawal had only about a 7% chance of failure over 30 years. That is in line with a prudent plan.
Keep a 3-year cash buffer. Bear markets are common, but the average time from market bottom to a new high is ~3.3 years, and the average time just to exit the bear is ~1.7 years. Holding 3 years of spending in cash or guaranteed income lets you avoid selling stocks at the worst time.
Rebalance patiently. If stocks slump, add to them. If they surge, trim. You are leaning into mean reversion rather than guessing.
Where to look for return right now
Valuations in the S&P 500 look rich by long-term yardsticks like CAPE (think of CAPE as a 10-year, inflation-adjusted P/E that smooths out booms and busts). The guest flags better hunting grounds: international markets, value stocks, and U.S. small caps. The key is price paid. If an area is cheaper than normal, history suggests stronger future returns.
Bonds are not the “safe” answer you think
Bonds can suffer long stretches of weak real returns when inflation runs hot, and bond returns often “trend” rather than mean revert in those periods. That raises sequence-of-returns risk if you lean too hard on bonds. The surprising result in the data: portfolios that are too bond-heavy can have a higher chance of failing over a long retirement than stock-heavier portfolios paired with a cash buffer.
Why most planning software undershoots
Many tools assume a “random walk,” which treats each year’s return as independent of the last. That misses mean reversion. The result is overly wide downside paths for stock-heavy portfolios and, in turn, advice to cut equity or cut withdrawals more than necessary. Plans that bake in mean reversion produce more realistic risk and often support higher, safer stock allocations.
3. Stocks vs Bonds: what asset allocation is right for YOU?
Podcast: Rational Reminder, Ep. 373: Asset Allocation in Practice
The podcast is hosted by Benjamin Felix (CIO at PWL Capital) and Dan Bortolotti (Portfolio Manager at PWL Capital), and Cameron Passmore (CEO at PWL Capital).
Asset allocation (stock-bond mix) matters
Inflation erodes spending power. To keep up and get ahead, long-term money belongs in diversified stocks and bonds, not cash. Simple math from the show: since 1970, $1 in 100% bonds grew to ~$49, a 60/40 mix to ~$98, and 100% stocks to ~$130.
Bigger upside comes with bigger drops, which you must be able to stomach. In 2008, 100% stocks fell 48% and took ~4 years to break even, while a 40/60 mix fell 19% and recovered in ~9 months.
Risk is two things: tolerance and capacity
Tolerance is your willingness to watch your account swing without bailing.
Capacity is your ability to take risk given your real life.
Factors affecting or demonstrating your tolerance and capacity:
Income stability and emergency funds
Insurance in place
Time horizon for withdrawals
Defined-benefit pensions or government benefits that act like “bond-like” income
Plan first, then pick your stocks/bonds mix
Build a plan from point A (where you are) to point B (retirement), then test asset mixes inside it. For near-retirees and retirees, this often shows they can dial down equity and still meet goals. For accumulators, they identify the “floor” return needed, then decide how much extra equity risk is worth taking to improve retirement age, spending, or legacy.
Practical levers that change the answer
Pension present value: A large lifelong pension can justify more equities in the portfolio, if your temperament allows, because your overall household “asset mix” already has a big fixed-income piece. The flip side is you may not need to take extra risk to hit your goals. Temperament wins.
Debt prepayments: Paying a mortgage faster is a guaranteed after-tax return. That can support more equity risk in your investable portfolio, if you want it.
Behavior over theory: Many people are fine with 100% stocks in a bull market but not in a crash. The advisors often start newer investors a bit more conservatively, then move up only after lived experience proves they can handle it.
Dollars, not percentages: Decide using dollar drawdowns. A 30% drop on $5M is a $1.5M hole. If that number makes you queasy, reduce equity.
Bottom line
Asset allocation is not a personality quiz. It is a planning decision that blends math, money habits, and psychology. The right mix is the one you will not abandon when markets get mean.

Disclaimer
This newsletter is for informational and educational purposes only and should not be construed as personalized financial, tax, legal, or investment advice. The strategies and opinions discussed may not be suitable for your individual circumstances. Always consult a qualified financial advisor, tax professional, or attorney before making any decisions that could affect your finances. While we strive for accuracy, we make no representations or warranties about the completeness or reliability of the information provided. Past performance is not indicative of future results. All investments involve risk, including the possible loss of principal. The publisher, authors, and affiliated parties expressly disclaim any liability for actions taken or not taken based on the contents of this publication.