BH
Biglari Holdings Inc. Class B Common Stock
stock NYSE

There are a few potential strategies…the BH one is pretty easy: VT and chill for 60 years.
The others require effort and skill and probably don’t return much more than just VT and chill over the long haul.
1. Private equity is meh before $30m, probably higher. Real estate is an option but requires work and a little luck as opposed to indexing that requires a little less luck and no work. Which will do better over 60 years depends on your skill in choosing real estate and managing real estate. Your day job will be being a doctor…passive seems to be the way to go.
Historically equities do better than real estate.
https://www.frbsf.org/wp-content/uploads/wp2017-25.pdf
Note: I’ve only just skimmed this paper looking for historical global stock and RE returns…
2. Most of the time whole life isn’t worth it. I’d personally cash it out. 4% guaranteed sounds great until you hit a 10 year patch of high inflation.
3. The laws will be different in 50 years. Revisit this topic when doing your own estate planning.
4. The data says “Reply hazy…try again later”.
5. Building generational wealth is a laudable goal but a dynamic one of 60 years. Sure there are things you haven’t thought of for taxes, wealth transfer etc but worry about them after you cross 7 figures and actually have the possibility of future generations. Until then it’s academic and a decade or two away.
$100m (nominal) is possible via passive investing $400K into the global equity market for 60 years with a little luck. The failure of equity markets within this timeframe would likely result in generational wealth being the least of your concerns…

All the comments I’ve seen so far are good. My only addition is to try to understand the business reason dividends exist and not just the financial reasons of where they fit into a portfolio. There are many who get into the financial point about total return being superior to dividend theory. It’s fine. But there is a legitimate reason dividends exist in a business and it helps to understand why that exists to determine if/where you place it in a portfolio.
I tend to be 90% BH and 10% fund picker. Earlier this past year I started to shift a bit of my allocation into BRK B stock. I view it as a heavily diversified value fund (typically dividend earning) that is defensive in nature that does NOT pay dividends which is better for me right now as I’m in my higher earning years. But they are generating dividends within the underlying fund - just not distributing to me as a taxable event. This is an example of me thinking about where dividends come into play in terms of financial/business theory and how I’m choosing to use them - defensively without rotating out of equities in that allocation.

Never. Dividends are an illusion. They come from profits and therefore company value. So, when a stock pays high dividends its value generally goes down in proportion to the dividend paid because the company is that much less valuable. So it’s a wash financially and you might be subject to tax on those dividends.
But there is another issue. If a company is paying substantial dividends, it’s not investing that money in further growth, which generally suggests it lives in a mature industry, aka one where future growth is limited. That further suggests that it might be a sub optimal investment.
Now here comes the BH spin: you’d prefer to buy growth stocks early in their growth cycle, but none of use are good at picking them. What’s a future, or current, millionaire to do? Buy the broadest possible fund knowing that historically more, and more valuable, winners have risen to the top than losers have fallen to the bottom so you make positive returns for long enough that you become rich.

You didn’t lose anything if you didn’t sell and realize the gain.
If you chose a low cost index fund and bought it to hold for the long term without focusing on its performance daily or weekly or monthly and plan on just contributing as much as possible for many years the results today shouldn’t matter. If the goal is to take advantage of compound interest and endure the market downturns through your journey because the end result may still be an AVERAGE return it’s not really the same as gambling in a casino.
Why do you check it every day? Ask yourself if it tripled tomorrow would you sell and realize the gain? If you would then you’re gambling not investing. How you approach the journey determines whether it’s gambling or long term investing which is what makes it tricky.
Btw- I suffer from the same thing. So, you’re not alone. However, I’m working on the handling the emotional parts of investing which is what makes us not good bogleheads. I believe that getting better at not allowing the emotions to influence your decisions and following the BH strategies without much deviation is what separates BH investors from gamblers.
It’s an easy concept to understand but difficult to implement!