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We’re not in a bubble… yet
Over the last couple months, there have been multiple headlines calling the stock market in a bubble, including from prominent business people and investors like Jeff Bezos and Jeffrey Gundlach. “This (AI) is a kind of industrial bubble.” - Jeff Bezos (Oct 2025) “(stock market) is least healthy (seen in my career)” - Jeff Gundlach (Nov 2025) What do we think? Public stock markets are not in a bubble, yet (but venture capital investment in AI probably is). Goldman Sachs recent
Dec 11, 20253 min read


Year-end tax planning for wealthy families
Tax savings to consider heading into this holiday season As we approach the end of another year, it’s important to take stock not only of our blessings heading into the holiday season, but also of our taxes. Below are five tax-related items every wealthy family should review before December 31st: Update your tax estimates Gift highly appreciated stock to charity Harvest losses (or gains) across your portfolio Reviewing gifting of assets to your children Maximize retirement pl
Nov 20, 20254 min read


Navigating the Risks of a 351 Exchange
We wrote earlier this year about strategies to diversify out of highly appreciated stock , including a solution called Section 351 exchange. While a 351 exchange allows you to defer (not eliminate) taxes by exchanging a “diversified” portfolio of appreciated stocks for a diversified ETF, there are risks to be mindful of. The takeaway is to engage in this type of transaction only with experienced ETF sponsors who also can reliably grow their fund after launch. In this post, we
Nov 7, 20254 min read


Book Review: 5 Types of Wealth by Sahil Bloom
In the world of wealth management, conventional wisdom often focuses solely on financial accumulation. However, a recent book...
Sep 18, 20253 min read


What is a 351 exchange and how can it help you?
If you hold an outsized and highly appreciated position that you would like to diversify out of, then this post is for you. Many people find themselves in this situation, whether you acquired it by working at a successful company for many years, buying early, or receiving the holding as a gift. In this post, we assess several options available, with a focus on the 351 exchange as a tax-efficient and low-cost way to diversify. Tools for diversification Some solutions are simpl
Aug 22, 20253 min read


Mid-year Update on Long-term Expected Returns: Premium offered by Equities is Low
This is our mid-year update on the long-term expected returns of various asset classes, a calculation we perform twice annually. After April lows for stock prices, the rebound in stock prices has been rapid. High returns for stocks today often mean lower returns in the future. This update aims to quantify for you just how much of future returns have been pulled forward. Our estimates are grounded in first principles: the fundamental driver of value is future cash flows. For b
Aug 1, 20253 min read


Charitable planning under recently updated tax law
Much has already been written about the updates in the new tax bill that was just passed. Most changes for individual tax payers are...
Jul 21, 20253 min read


Does the S&P deserve a higher P/E today?
Every time the stock market falls, media headlines suggest reasons to wait before buying (i.e. trying to time markets). In early 2025, the S&P 500’s price-to-earnings (P/E) ratio was 27, which was the highest it had been in 25 years, excluding a short period during the 2021 COVID lockdowns. While this implied that US stocks were expensive and future returns would be low, bank research departments held a bullish outlook on future returns. During the “tariff tantrum” in April,
Jun 13, 20254 min read


Long/short tax loss harvesting: pros and cons
Tax-aware hedge fund strategies promise outperformance and tax efficiency but are their claims overstated? We just released a white paper titled "Tax-Aware Hedge Fund Strategies: Separating Hype from Substance" which analyzes these claims. Tax deferral is valuable, as delaying taxes allows for greater investment growth. This value increases with longer deferral periods and higher returns. All tax-efficient investing offers this benefit, including buying and holding individual
May 8, 20252 min read


Decoding the Roth IRA Conversion: Is It Right for You?
There's a lot of buzz around Roth IRA conversions, and for good reason. Converting your traditional IRA can be a powerful financial move,...
Mar 4, 20254 min read


Rethinking Defensive Equities: Valuation Matters
For decades, investors have sought "defensive" equities—stocks that hold up during market downturns. Traditional thinking favors stable,...
Feb 18, 20252 min read


Why it is so hard to outperform the stock market
Our founder and Chief Investment Officer is interviewed about why it is so hard to outperform the stock market. At Greenline Partners,...
Jan 15, 20251 min read


Why the S&P 500 Deserves a Higher P/E Multiple Than History Suggests
Executive Summary Current Valuation Perspective : The S&P 500's current P/E of 27 may appear high historically, but it doesn't signal a bubble, as today's profitable growth companies differ significantly from past periods that favored growth stocks. Earnings Quality Analysis : Historical data indicates that unprofitable growth stocks tend to underperform, especially in speculative environments. However, today’s leading growth stocks feature high profit margins and cash flow
Nov 19, 20244 min read


Living a Long and Fulfilling Life in Retirement
In wealth management, we are always focused on saving enough money to get through retirement, but relatively little effort is spent on...
Nov 12, 20241 min read


The importance of fees and taxes
One of the key characteristics of a good financial advisory firm is alignment with clients and minimal conflicts of interest. But what...
Nov 8, 20241 min read


Simple beats complex: Buy and hold beats hedge funds after fees and taxes
At Greenline Partners, we leverage many invaluable lessons from our experience at the world’s largest hedge fund—not just about effective...
Oct 28, 20241 min read


Greenline: It started with Dad
Many friends and clients ask about the origin of our company, below is how it all started over 12 years ago. It started with Dad. His...
Oct 24, 20241 min read
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