What’s @tomato’s goal?
$100M. Don’t like your $25M. Not sufficiently stretched.
You need to tell your sons to work harder.
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I think after you go beyond $20M, getting more money will not improve your standard of living, and other factors come into play.
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Man i had high dreams look like.
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One thing I am very sure. Continue to do what I am doing now, can’t achieve tomato’s goal. Need a fundamental rethinking.
I have an idea for you, you can either go 100M, or get a nice shave on your net worth: Make your mad man options portfolio your main portfolio 
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The way I am planning to approach this:
- Buy primary
- Soon after buy an investment property
- Buy an income replacing business, so i can be hands off, but still have at least 50% of my current comp. This will probably take couple years to achieve.
- Scale the business and maybe buy another one or so to have more income.
- Rinse, repeat 2,3,4.
In the meantime, with additional time i have explore different ideas.
As time goes by (3) becomes hard, as total comp increases over time. This 1-5 is probably enough to get 20M, but probably won’t make 100M. 100M is in the exploratory ideas, but likely they are not to go anywhere.
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If you are going to do 1, 2, and 3 in parallel rather than serial, then you might have a better shot at it.
Yeah that’s the plan, but if i stretch 1 and 2, 3 suffers.
Then rather than buying a 2.5M primary, just buy a $1M property and can use the other $1.5M for 2 and 3
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You are single, aren’t you?
Really. Human population will go extinct if everyone needs a $2.5M mansion to be married.
that’s not what i meant. IT’s ok
You have a funny sense of a mansion. 2.5m gets you crapshack in places we are looking for 
What exactly did you mean then? You mean your wife is a bridezilla and demands a $2.5M house for dowry?
IT’s fine, that’s between me and my wife. Not everything is financially optimized, you write it off, and move on. I make good income and on good growth path, so i am not that concerned.
I told him to buy options. Stock market dived today. Buying SQ options with 6 month expiration 3-4 strikes in the money could double his net worth.
But also could take it down.
Not even close. Wqj would say “buy tesla and wait it to become 500b$ company”.
I think you can reverse the order a little bit. Why not go with 2 first instead of 1? You are in a rent controlled apartment. Might as well make full use of it.