One of the Things That Helped Me …

I thought of this "stupidity insurance" as writing my own self-insured retirement plan or insurance policy that would guarantee that by the time I was ready to stop working, I'd be able to take $21,422.71 per month after taxes WITHOUT EVER SAVING ANOTHER DIME after my 30th birthday. Anything else I built up - my businesses, my houses, my art collections, my brokerage accounts, my main retirement accounts - is extra (and, frankly, where the *real* money will be). The account should maintain its value of $6,426,814 over time, meaning that the whole sum could be left to my heirs or given to the family foundation for charitable purposes.
From time to time, you may come across reference to my “stupidity” insurance or my “reserve” fund. I’ve had a bunch of readers write me over the years and ask about various comments I’ve made so I thought it might be useful to explain it. My parents, siblings, and Aunt Donna have always known about my investing but virtually no one else did when I was a child (by the time I got into high school, though, it was all I talked about so hiding it was no longer an option).
For those of you who are older than 14, this isn’t going to do any good unless you have children or grandchildren that may benefit from some personalized version of it (which is why I’ve never written about it). By the time I was older, we had put almost all of my siblings on a modified system that helped to guarantee they would enjoy the same outcome in their own retirements. This plan has some resemblance to the dividend trust program I described in an article on student loan debt.
How the Stupidity Insurance Fund Came About
The program worked like this: If, starting at 14 years old (which was 4 years in the future at the start of the program), I could save $500 per month by working after school or doing side projects for people, and I could park the money at 5% until I was 30 years old, I would have roughly $141,945 in this insurance fund. I’d kick in the extra $55 to make it an even number, so let’s call it $142,000.
This $500 was my “insurance premium”, so I didn’t think of it as saving or investing because that is what my brokerage accounts were for – for all intents and purposes, this money didn’t exist to me. I treated it like an expense, or a car payment. I did everything possible to get it into tax-advantaged accounts such as a Roth IRA or SEP-IRA because I wanted the money to be able to grow tax-free when it reached what I called “the vesting date”, which was my 30th birthday. This was the date at which I would stop contributing money to the fund and split everything that had built up since I was a kid into different asset classes (stocks, bonds, mutual funds, real estate, options, etc.) and invest it in such a way that it could be passively ignored for years. In many cases, the law requires you to take distributions from your retirement accounts by the time you are 70, so that would be 40 years of compounding.

By putting money into assets that generate cash and grow in value over time, like businesses that are attractively valued, the money in this self-created retirement plan or retirement insurance policy silently compounds for decades in the background as we all go about our lives.
If this passive money earned 10% (I have a history of earning much more, and I planned on utilizing things such as self-directed IRA accounts that would allow me to actually buy an apartment building or hotel, for example, as the money grew but I’m keeping it there for the sake of conservatism; most people should bet on 7% to 8%), by the time I reached 70 years old, the “insurance fund” would have $6,426,814 in it. There would be virtually no taxes owed on this money because of the types of accounts in which I had placed the funds.
Most research shows that even in a Great Depression scenario, withdrawals of no more than 4% per year mean that you’ll never run out of money. At a 4% rate, I could take $257,072.56 in dividends out of the account each Christmas for the rest of my life. That’s $21,422.71 per month after taxes that I could live upon, simply because of money I saved from the time I was 15 to 30 years old without ever contributing another penny.
The Psychological Effect of Having Your Own Stupidity Insurance
Some psychologists and money managers have written about similar programs, which they call your “go to hell” money. They call it this because you know that no matter how bad things get, whether or not you lose your job, change careers, or get divorced, if you are unhappy, you can get up, walk out of the building, and tell everyone to go to hell.
The main benefit of the program is intellectual freedom to pursue what you want to do without fear. It could be argued that one of the reasons I launched companies after graduation, rather than take a job at Merrill Lynch or Goldman Sachs, was because I knew if I failed, I’d still end up rich and I could always get a job tomorrow.
Related posts:
- I Will Probably Add Shares of Nestle to the Retirement Insurance Plan (But They Still Seem Overvalued)
- New Stocks and Cash Added to The Kennon Retirement Insurance Fund (or “Stupid Fund”)
- Some Interesting Surprises Hidden In Your Insurance Policy
- Wal-Mart Ends Profit Sharing, Ups Retirement Plan to Offer 6% Dollar-for-Dollar Matching on 401(k) Savings, and More
- Berkshire Hathaway Board of Directors Approves Share Repurchase Plan
- Dividend Investing In My Retirement Account – Part II (Six Month Update)
- Dividend Investing In My Retirement Plans
- Retirement Investing: A Married Couple Working for Wal-Mart Could Retire and Live Very Comfortably
- Reynolds Tobacco Company and Its Legendary Employee Stock Ownership Plan
- A Visual Picture of the Kennon Green Enterprises Business Model




