9: Portfolio Strategy, Why Money Mangers Fail, and Chicks of Fintwit


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Let’s dig in.

Interesting Reads


Lou Simpson, the former Chief Investment Officer for Geico answers a Q&A session. Lou is pretty private, so when he speaks people listen.

He’s also considered “one of the greats” by Warren Buffett.

I think there are people who have the right mindset and maybe contacts, and certainly luck, who could outperform the market. But if somebody’s going to invest using hot tips, or listening to CNBC, or investing with so-called wealth managers at brokerage firms, I think it’s a loser’s game for them.



I find money management fascinating. I can see how running an organization, if not careful, can lead to poisonous practices. Especially so in money management.

Creators and the Creator Economy with Kyla Scanlon

Viewing the landscape from Caitlin’s and Kyla’s perspective is valuable. If you’re starting your own venture, or embracing the new economy, listen to this podcast. I listend to this podcast while training, which is saying something. I usually listen to music

Resources & Tools


My go-to time tracker. It’s helped me immensely to see where my time goes, and has helped me increase effectiveness about 2x.

And it’s free for solo-preneurs.

Tip: Just start tracking time, then look at a weekly time report of where your time went. Very powerful.

For Fun


Bookmarks from this week that I found very interesting. There’s youtube videos, threads, one-offs, and gems.

Quote Of The Week

By reading, you learn through others’ experiences, generally, a better way to do business, especially in our line of work where the consequences of incompetence are so final for young men. ~ Jim Mattis

General Mattis is one of the heroes and living legends to the Marine Corps. He served 1969 – 2013 and then as SECDEF. Extremely intelligent, demanding. A brilliant thinker and doer.

After retiring he wrote one book. I highly recommend it.

Some Thoughts

  1. My writeup on DocuSign is coming out soon. You can get access to it by signing up by clicking the button below.

  2. There seems to be a lot of cynicism on twitter among professionals. While I can understand the pull to cynicism over time in a given industry, it’s still no excuse. If someone is intelligent, revered, and successful but also cynical then they do not belong in my inner circle. Attitude matters so much, mental health matters so much. It even matters for the investing veterans out there. I think it pays dividends to be deliberate about who we let into our inner circle. (and of course to observe our own attitudes)

  3. I’m now 36! Just had a birthday the other day. Never thought I’d be here doing this at this age. Feeling very blessed, even though it’s extremely early in the game!

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