- Appointment reminder: how to ignore a business for four years, while not improving it and giving you stress
- financial planning using a spreadsheet, then moving to more expensive lifestyle, getting in debt and having the retirement fund turn negative when he has a wife and child and is closing down his companies. Something we can all learn from?
- when to borrow money and how to calculate risk: Except he says not to trust his calculation of risk when he encourages the reader to play poker against him if possible because he's so bad at risk estimation.
- when and how to sell your startup: again no, he says it put him in a bad position to be wanting to sell quickly, and he glosses over 'how' with "I know how because I've done it before". The only good read there is "don't wait until it is declining before selling, like Bingo Card Creator was".
- the trials of shipping (six weeks became three years): the trials of promising and pre-selling a thing, then changing your mind and doing a startup instead, and trying to turn that into a positive. (Aside: Three years? I wonder how long before there's a reasonable chance that some of the purchasers died before the release?)
- setting goals for the future: where he keeps saying he didn't meet his goals, or they have changed?
- the value of family: "I had not felt as effective as a husband / father recently as I wanted to be" - the value of family is lower than a side-business he was bored of and wants to sell? Lower than a "huge amount of personal fulfillment" that he got instead during that time? Lower than the guilt of refunding customers over his video series? If you were a potential customer and he said "I choose to spend more time with my family, I can't do this work justice, sorry, here's a refund", wouldn't you be fine with it?
I don't dislike him at all, I do respect him, and I like the transparent views into his life and businesses and plans and thoughts, but I'm not seeing the same things you are at all. If anything these are more cautionary tales along the lines of "you can sometimes get what you want with hard work, but it comes with a price".