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Jesse Cramer

Maximizing Wealth vs. Minimizing Risk ⚖️

Published about 16 hours ago • 1 min read

Good morning!

Today's email includes:

-- a podcast episode about maximizing wealth vs. minimizing risk

-- an old article about "learning to surf" the wild waves of investing

-- some good stuff from around the Internet about private investing, stock picking in 2026, and the new hottie in town: bonds (?!)

Maximizing Wealth vs. Minimizing Risk

Our competing goals in retirement require trade-offs.

Optimizing one part of a financial plan can create problems elsewhere.

This podcast episode is all about the tension between maximizing lifetime wealth and minimizing the probability of retirement failure.

Along the way, we discuss sequence-of-returns risk, the limitations of Monte Carlo analysis, and the importance of understanding an investor's need, ability, and willingness to take risk.

You Can't Control The Waves...

In spring 2024, we were getting ready for our first child, and attending birthing classes.

The teacher described birth as follows:

You can't control the waves, but you can learn to surf.

The birthing process is innate, instinctual, or subconscious. The body does what it does. It’s easy, therefore, to think that mothers are along for the ride, victims of their own bodies.

But the birthing class teacher empowered her students to realize that they can “surf.”

What an amazing metaphor for long-term investing, too.

Read the article below.

The Top 3...

I enjoyed this content recently. I hope you do too.

​The Four Challenges of Private Investing...​

Private investing feels attractive.

Venture capital and private equity evoke exclusivity. The chance to "get in on the ground floor."

This opportunity -- once reserved for institutions and the ultra-wealthy -- now seems within reach.

But there are challenges to be aware of.

​Picking Stocks in 2026​

Here's how some stocks are performing as compared to their all-time highs.

Google (-30%)

Intel (-50%)

Dell (-28%)

Netflix (-50%)

Oracle (-60%)

Home Depot (-25%)

Chipotle (-55%)

Pepsi (-32%)

Nike (-79%)

[BTW - the overall market is UP 11% on the year]

Picking stocks is hard.

​Bonds Look Good​

For the first time in long time, bonds are looking good.

(side note - I think of bonds more as a financial planning tool than as an investment opportunity, but I still think this is interesting)

"Yields are up, and durations are down, tilting the risk/reward in investors’ favor."

I Help People Retire (Even) Better

I'm a Partner at a fee-only fiduciary retirement planning firm.

We work with clients all over the USA.

If you know someone who needs help, visit PlanWithJesse.com and let's start a conversation.

Until Next Week...

Thank you for reading, listening, and writing back. People like you send me questions every day.

I'd love to hear from you. ​​

All the best,

Jesse Cramer

Jesse Cramer

Smart ideas about money and retirement.

Retirement is a different game. You’ve spent decades building wealth. Now comes the harder part - turning it into a paycheck that lasts. I’m Jesse Cramer. I help DIY investors turn their savings into a clear, cohesive retirement plan. Join 4000+ weekly readers and 20,000+ podcast listeners.

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