Coastwise Capital Group

08/25/2026

The Call Is Coming from Inside the House

In last month’s newsletter (July 2026 Newsletter) we discussed the various sources of risk, with the ultimate form of risk being not knowing what you are doing. Translation: we as individuals – investors or otherwise – are often our own worst enemy when it comes to where risk truly resides.

But it is human nature to want to blame someone or something else – the proverbial ‘they’ out there somewhere conspiring against us (the ‘victims’). While that may be an easy out, it is only that: an excuse to remove self-responsibility and accountability.

Case in point: the recent Situational Awareness hedge fund blowup. Over the course of a few days last month, this once $45 billion hedge fund run by 25 year-old wonderkid Leopold Aschenbrenner collapsed by roughly $35 billion. What was the big culprit? Some exogenous event like an unexpected and unknowable pandemic or terrorist event?

Nope.

Click the link below to read the full article.

https://www.coastwisegroup.com/blog/the-call-is-coming-from-inside-the-house

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The Call Is Coming from Inside the House In last month’s newsletter (July 2026 Newsletter) we discussed the various sources of risk, with the ultimate form of risk being not knowing what you are doing. Translation: we as individuals –...

07/24/2026

Wax On Wax Off: The Real Definition of Risk

We hear financial commentators often talking about the notion of risk in investing. 'The market was higher today and telling us the risk trade is on…' Another common reference to risk relates to how volatile the market is in the near term as evidenced by comments like, 'I expect the markets to be a lot more volatile and riskier leading up to the next Fed meeting in 2 weeks….'

But is the ownership of stocks, and the short-term movement thereof, the best definition of risk? Or even a good one? Let's examine more closely.

Two investors own the S&P 500 (SPY). One is saving to buy a house in 6 weeks, the other for retirement in 20 years. They both own the same asset - the SPY - but are they taking equal risk?

Click the link below to read the full article.

https://www.coastwisegroup.com/blog/wax-on-wax-off-the-real-definition-of-risk-1

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We hear financial commentators often talking about the notion of risk in investing. 'The market was higher today and telling us the risk trade is on…' Another common reference to risk relates to how volatile the market is in the near...

06/18/2026

The Power of Boring

“It takes 20 years to become an overnight success.”

When I was 11, I set a goal of becoming a world champion sailor. Nine years later I was at the top of the podium - and a ‘star’ - albeit within the small world of sailing. Suddenly, I was in demand by journalists wanting to interview me, parents wanting me to coach their kids, etc.

What occurred during that 9-year period from being an unknown junior sailor to a world champion in the spotlight?

A lot of very boring, unglamorous, basic work. Hours upon hours of solo sailing practicing the same things over and over. Simple routines repeated endlessly. That is what it took to become a world champion.

So, how does this apply to investing?

Click the link below to read the full article and for more investment (and life!) insights.

“It takes 20 years to become an overnight success.” When I was 11, I set a goal of becoming a world champion sailor. Nine years later I was at the top of the podium - and a ‘star’ - albeit within the small world of sailing. Suddenly, I...

05/20/2026

Diamonds Are Forever

The great Warren Buffett has been quoted as saying his favorite holding period for stocks is forever. However, even the investor who is known as the quintessential ‘buy and hold’ shareholder is surprisingly active when it comes to his stock portfolio. Large investors like Buffett are often required to file SEC form 13F which discloses many of their recent buys and sells. Just on their latest 13F alone, Berkshire disclosed transactions in multiple stocks including GOOG, DAL, M, NYT, CVX (selling nearly 46 million shares or almost their entire position), V (total exit), MC (total exit), AMZN (total exit), UNH (total exit), DPZ (total exit), STZ (total exit), BAC, NUE, and many others. And that was just for a 90-day period!

So, if even Mr. Buy and Hold himself regularly liquidates stock, what criteria should an investor be considering when it comes to selling?

Click the link below to read the full article and for more investment (and life!) insights.

The great Warren Buffett has been quoted as saying his favorite holding period for stocks is forever. However, even the investor who is known as the quintessential ‘buy and hold’ shareholder is surprisingly active when it comes to his...

04/29/2026

This Time Is Not Different

“This time is different….” Known to many as the four most dangerous words in investing.

During the dot com bubble of the late 1990s, these words were uttered by those justifying nose-bleed valuations for companies worth billions on paper but with no revenue (not no profits, no actual sales). The thinking was, ‘eyeballs are all that matter – it’s different this time.’

Of course, it was not different that time, and eventually the companies without real revenue and profits saw their stock prices plummet, and, in many cases, the firms went belly up.

A similar situation happened during the S**C debacle of the early 2020s...

Click the link below to read the full article and for more investment (and life!) insights.

https://www.coastwisegroup.com/blog/this-time-is-not-different

03/10/2026

How To Survive A Bear Attack

I seem to write a primer on how to survive a bear market sometime each year – even though statistically speaking bear markets (defined as declines of 20%+ from peak to trough) are fairly rare, occurring on average about once every 5 years. They are not possible to predict (actually, I take that back, you can predict one every day as people often do, and you will eventually be right, but you will have likely paid a large price for being out of a market that has risen 30%, 40%, 50% or more while you were sitting on the sidelines. These people often proclaim victory that they avoided a 22% decline, but they fail to point out that they would have been much better off being invested the whole time even after factoring in the sell-off). Bear markets take on all shapes and sizes as the impetus is usually something unexpected. It is also not possible to determine when the 6% decline quickly turns into a 10% gain and never gets into correction territory (10% - 20% decline), let alone becomes a full-fledged bear market.

It is now March 2026, and investors have been waiting anxiously for the next bear market (the S&P 500 almost hit bear market territory in the Spring of 2025 but not quite), which seems to have been ‘around the corner’ for nearly 5 years (along with that nasty recession that has yet to occur while our economy, employment, etc. keeps humming along).

Click the link below to read the full article and see the tips on how to survive a bear market.

I seem to write a primer on how to survive a bear market sometime each year – even though statistically speaking bear markets (defined as declines of 20%+ from peak to trough) are fairly rare, occurring on average about once every 5...

01/27/2026

This is the time of year where people often set…and let go of….New Year’s resolutions around things like health and fitness. I decided long ago that the one of the best investments I could ever make was in my health, so I am very...

09/25/2025

Empowering the Next Generation

Take a look at the Coastwise September monthly newsletter "On the Power of Financial Literacy" for a closer look into my most important book yet, The Other Birds & Bees: Money $ecrets No One Ever Taught You, and how we can help today's young adults make smart money choices for a brighter tomorrow.

Click the link below to read the full article.

https://www.coastwisegroup.com/blog/on-the-power-of-financial-literacy

Order your copy here:

https://www.amazon.com/Other-Birds-Bees-Financial-ecrets/dp/B0FRSG7CX9/ref=tmm_pap_swatch_0?_encoding=UTF8&dib_tag=se&dib=eyJ2IjoiMSJ9.xk4RYhPZRV6ceQ3lmv78MOzHBrGxpiBY0l_Gdj6Ak1tP3Vp381AMfreS3JDAlA0wroB420b9xDIF5ing7JZjkhGy3Jx1fvewk7HBvuskXlDMIs_UCc6JkI5DbbRiHr3gk78Xd6OtHmVUO8cfH-wkfTKDqR37vPKalCjnp3bYI91gFDcu48duoT_5ZKr22-0NKWOPLUsMhChTNr_IvHwsp1IElCVZcvLsF3GFLRKjJp4.A-xkS9xvcHHEoapBK3TyMpQf74TgHqG1cI-_a_g3YJM&qid=1758553776&sr=8-1

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09/25/2025

How Wealthy Are You Really?

Take a look at the Coastwise monthly newsletter "On the Commonalities Between Wealth and Health" for insights on the value of real wealth.

Ask Steve Jobs as he was lying in a hospital bed – or even 94-year young Warren Buffett as he tap dances to work – what the most important thing in the world to them is, and they would not cite their bank account balance but rather....

Click the link below to read the full article.

https://www.coastwisegroup.com/blog/on-the-commonalities-between-wealth-and-health

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“It is health that is real wealth and not pieces of gold or silver.” - Gandhi Ask Steve Jobs as he was lying in a hospital bed – or even 94-year young Warren Buffett as he tap dances to work – what the most important thing in the world...

07/02/2025

Are You An Original Thinker? Happy Independence Day!

Take a look at the Coastwise July monthly newsletter "Independence Day: What Makes a Great Investor" for common traits of highly successful investors and insight on the independent thought.

Let me tell you a story about an 11-year-old boy. He grew up in the Midwest where sports like ice hockey and baseball were all the rage. His town, Chicago, even had 2 baseball teams, and the famous Chicago Bears football dynasty of the...

Click the link below to read the full article.

https://www.coastwisegroup.com/blog/independence-day-what-makes-a-great-investor

♻️ Repost to spread the message

Let me tell you a story about an 11-year-old boy. He grew up in the Midwest where sports like ice hockey and baseball were all the rage. His town, Chicago, even had 2 baseball teams, and the famous Chicago Bears football dynasty of the...