Adam Grossman - Mayport Wealth

08/25/2026

In 1999, Jeff Bezos appeared on The Tonight Show. Throughout the interview, Jay Leno kept asking Bezos to explain why investors should be comfortable with a company losing historic amounts of money. Bezos just chuckled. With the benefit of hindsight, it’s clear that investors would have been better off getting over their skepticism. But at the time, the stock looked enormously overpriced.

It’s not just Amazon. We’ve seen this pattern repeat. Today, for example, it isn’t clear how to look at SpaceX. Tomorrow it will be another highflier. How can investors square this circle? That’s today’s topic on the Investor’s Bookshelf:

https://www.investorsbookshelf.com/p/can-lightning-strike-twice

08/20/2026

Why does investing sometimes feel like an uphill battle—and how can you combat it? Today on the Investor's Bookshelf. https://www.investorsbookshelf.com/p/charlie-mungers-most-valuable-advice

08/18/2026

Are Treasury bonds an unnecessarily conservative investment? Today on the Investor’s Bookshelf.

https://open.substack.com/pub/investorsbookshelf/p/old-reliable https://open.substack.com/pub/investorsbookshelf/p/old-reliable?r=2baul&utm_medium=ios

08/10/2026

Amazing statistic:

https://www.wsj.com/economy/the-rise-of-the-unstoppable-american-tourist-485f025b?st=ym8Guk

08/06/2026

A challenge in building an investment portfolio is that there are thousands of stocks and thousands of mutual funds and ETFs out there. How do you choose among them? Today on Investor’s Bookshelf: https://buff.ly/MdvcL3E

07/30/2026

Does the financial system today work better or worse than in the past? More to the point, how can you get it to work better for you? Today on Investor’s Bookshelf: https://buff.ly/jixSpvo

07/28/2026

How did Warren Buffett build a portfolio for this family? Today on the Investor’s Bookshelf:
https://buff.ly/de0krhb

07/21/2026

In "Against the Gods," the late Peter Bernstein, described one of the flaws of Modern Portfolio Theory:

"Another mathematical problem stems from the idea that a portfolio, or the security markets themselves, can be described with only two numbers: expected return and variance. Depending on just those two numbers is appropriate if, and only if, security returns are normally distributed on a bell curve... No outliers are permitted, and the array of results on either side of the mean must be symmetrically distributed."

Bernstein continues:

"Nothing is perfect in the real world, so this is indeed a problem."

This is why Modern Portfolio Theory is an interesting concept—interesting enough to earn the Nobel Prize—but I'd be wary of using it to build an actual portfolio.

07/14/2026

What a great personal finance story.

Dave Lee got into personal finance when he was in middle school, and helped his mom set up a brokerage account.

07/14/2026

Charles de Gaulle, the former president of France, helps us understand the importance of diversifying.