Derek Johnson Derek Johnson

How to Blow a Fortune

True Stories of the Biggest Mistakes People Make After Getting Rich

Read the lessons

Why this book exists

When I sold my company, we had more money than we’d ever had before, all at once. Even with the best intentions and plenty of advice, we still made a ton of mistakes investing, managing, and spending it.

The more I talked to other people who had come into money suddenly, the more I realized how similar our mistakes were. Then I watched friends go through the same thing after us and make those same mistakes all over again.

I wanted to help break that cycle. So I interviewed people who had made millions and asked them about their biggest mistakes. Their names are withheld, but their stories are real and often painfully similar. I’m sharing them here so you can learn what we wish we’d known.

Read the intro

Lessons

  1. 01Struck by LightningHow much of your life savings is riding on one thing you feel certain about?
  2. 02The Safest HarborA decision that looked prudent, and what it actually cost.
  3. 03There's No Such ThingThe pitch that sounded too good, and the detail that gave it away.
  4. 04Update the Game PlanThe money plan you made before the money arrived may not survive it.
  5. 05It Was Never OursThe bill that arrives before you have spent a dollar.
  6. 06Hire Someone Who Says NoThe most useful person on your money team may be the one you least want to hear from.
  7. 07The Monthly Payment TrapWhy a purchase that feels small each month can be the biggest mistake of the year.
  8. 08Philanthropy Can WaitThe generous impulse that can hurt the people you most want to help.
  9. 09It Can't FailThe phrase that should make you walk away from any deal.
  10. 10Give Money, Not HousesWhen family asks for help, what kind keeps the relationship intact?
  11. 11Become the Expert FirstEvery deal arrives with a good story. Who in the room actually knows the business?
  12. 12Don't Try to Save PeopleWhen a friend's problem looks easy to fix with your money.
  13. 13Hedge What You Can't SellWhat to do with the stock you can't sell yet.
  14. 14Decide the Total FirstThe number to settle on before the first check clears.
  15. 15Don't Let the Tail Wag the DogA tax break that looked too good to pass up.
  16. 16Two Thirds, One ThirdA simple way to split the money the week it arrives.
  17. 17Don't Lock Up Money You Might NeedThe investment you can't get out of, and when that becomes a problem.
  18. 18Just Dump It InWhy waiting for the perfect moment can be its own expensive decision.
  19. 19Get a Nice RentalThe housing decision that feels like the easy part.
  20. 20Good Money After BadWhen the money already lost is the thing deciding your next move.
  21. 21Fifteen Minutes of Due DiligenceWhat fifteen minutes of checking might have prevented.
  22. 22That's What Rich People BuyThe purchases that signal wealth and quietly lose value.
  23. 23All In TwiceHow much of your net worth is too much to bet on one thing, including yourself.
  24. 24The Consequences of PublicityWhat happens when people find out what you have.
  25. 25The First-Year PlaybookThe short list for the first twelve months after the money arrives.