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Re:If founders treated their investors the same way they tre... by justinclift on Tuesday August 18, 2020 @01:34PM (#24201609)
> ... now I stand I make low 7 figures from the equity on this last company (publicly traded now).

Isn't that a "never need to work again" situation though?

eg, you've effectively freed up your future to put time into whatever you want?

Re:If founders treated their investors the same way they tre... by phone8675309 on Tuesday August 18, 2020 @03:08PM (#24202923)
Low 7 figures to me would be between $1,000,000 and $3,000,000.

I don't think that I would call that "never need to work again" money. It's between 10 and 30 years of my salary.

A good lump sum to stash in the retirement fund. Maybe retire at 55 instead of 65, but definitely not "never need to work again" money.

Re:If founders treated their investors the same way they tre... by icedchai on Tuesday August 18, 2020 @05:11PM (#24204401)
It depends on your lifestyle. If you ask the early retirement / FIRE forums, they'll tell you you're good to go.

If you have 2 million, you can conservatively (meaning a low 3% - 4% withdrawal rate) take out 60k to 80k a year in perpetuity. Can you live on 60k - 80k a year? Consider you'll be paying a lot less in taxes since it's all capital gains. If your normal salary was 100k ish, you probably can.

Re:If founders treated their investors the same way they tre... by justinclift on Wednesday August 19, 2020 @12:01AM (#24207031)
It's entirely possible to relocate to a different country with a cheaper cost of living, universal health care, etc too. So, the limits of the US system should be taken as a given.
Re:If founders treated their investors the same way they tre... by wikibob on Tuesday August 18, 2020 @11:12PM (#24206798)
You make $100,000 per year? If you are in the USA you are deeply underpaid.
Re:If founders treated their investors the same way they tre... by jason0597 on Wednesday August 26, 2020 @05:27PM (#24287477)
I don't know whether I should laugh or cry at this comment...
Re:If founders treated their investors the same way they tre... by svachalek on Tuesday August 18, 2020 @03:03PM (#24202836)
3% is a pretty good rule of thumb for perpetual withdrawal rate. If it's say $1M after taxes, that means $30k/yr. This is enough to retire on but only if you're willing to make lifestyle changes. Probably not that hard to do if you're 30 and single and renting, but married with kids and a mortgage it's a tough sell.

(Obviously as your raise the definition of "low 7 figures" this can change dramatically)

Re:If founders treated their investors the same way they tre... by gowld on Tuesday August 18, 2020 @11:11PM (#24206793)
If you're married and retired then your partner can work and you can be primary homemaker. $60K is just enough to pay for a modest house if you're friends with HN types, though.
Re:If founders treated their investors the same way they tre... by brogrammernot on Wednesday August 19, 2020 @05:57PM (#24217190)
Other folks already chimed in, but yeah $1-3M depending on how everything ends up.

After taxes and everything, it’s not “enough” to never need to work again but yes, I would say I’m very fortunate to not have money as the concern as long as I’m not irresponsible with it.

The point was more that it easily could’ve been another $0 and in theory, the company could fail taking that $1-3M down considerably.

The salary most HNers make is way above the median and is enough to live a very comfortable life. I honestly can’t tell you if the money was worth the personal pain of the last 10 or so years, truly I don’t think it is.

Re:If founders treated their investors the same way they tre... by anon9001 on Tuesday August 18, 2020 @03:13PM (#24202990)
I'd gladly trade all the relationships I have for the ability to never work again.

If I ever finish work, it's going to be a complete reboot of me anyway.