Has anyone made a big bet to try to attempt to retire early? It seems like everyone in this bowl focuses on traditional, conservative investing. Going that route I’m gonna be a wage slave all my life

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Am 44 M, a SM and I could retire tomorrow in a non taxable state !

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@SM2 - gross is about $150k net is about $50k

@Tax Associate 1
1- took as many tax deductions that I can and still do - 401k, Max HSA, Max dependent care - never invested in Roth and other IRA
2- saved saved saved and bought distress properties for the last 17 years

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I agree. So many here focus on HYS accounts paying 1.x%. Meanwhile US equities markets are up like 20% this year. It’s probably because fishbowl opened up to the lawyers, although I think that most consultants are also quite risk averse.

In terms of your question, I keep a portion of my net worth for “crazy” things. Not crazy stupid, but outside the norm. I made $$ on bitcoin because I was buying when it was ~$300. I am accredited and I’ve invested in two seed rounds. My vision is to do 3 investments of $5-$10k each per year to build a portfolio over the coming years. I also invest in funds that invest in private equity. Who knows if any of this will really pay out. But, I’m quite confident that not doing these things will not pay out on the scale that these other things could.

IMO you need to keep your eye on fringe things and get in on them before they become mainstream. If you follow the beaten path you will end up exactly where everyone else does. Or be a co-founder and have a solid exit.

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EM1: to get into funds you have to be accredited. Examples include Equity Zen (secondary markets), Angel List, 500 startups, etc.

To invest in seed rounds it’s the same thing, or you have to have a network that brings you deal flow and access to direct investment opportunities. That generally requires the ability to write big checks, or you have to be fairly involved in the startup space and add value to startups / develop a reputation for adding value. Then those companies will want you in their round.

51, ~6m in stock and cash, ~5m in 3 RE props(free and clear). Nothing fancy investing wise. Time + disciplined investing works.

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Is that even...possible?

I’m with you. In my few years in the ‘real world,’ have met very successful people that didn’t follow a traditional path (go to school, max 401k etc).

The one thing they had a common is that they learned early the power of running / owning a business. Much faster path to wealth vs depending on a company and being tied to a salary / frugality for 40 years. In business, their a stronger relationship between your earnings and effort.

I started with RE properties at 23 and started a business at 24. In the process of scaling both with the goal of making these investments my main source of income (not a side gig).

smart

What is a big bet for you?

Something like a third or more of your net worth on a single bet

I think people either FIRE (light) or figure out a way to generate passive income (real estate, side gig).

Unless you're planning to become an educated full time stock brocker, don't think your chances are great with trying to game the stock market. And even then, there is a real chance you'll lose our big and end up working until you're 75 just for a halfway decent retirement.

If you're just looking for better investment strategies, that is a different story and very doable with solid research.

Husband and I have made 2 very early stage investments in startups ($20K in each). Large possibility we’ve said goodbye to that cash, but small chance each may hockey stick.

Both were through friends, both part of early stage start-ups; well backed, good ideas & reputable set of people involved.

I have invested $5k in an angellist venture fund, I have a sizeable amount parked in Crypto (I’m 2x my investment in this bear market). I was very close to dropping serious dough in a friends startup, but decided against it, it’s too much capital concentration in 1 idea / concept for my taste. OP - u need to decide what moonshot means for u

My largest stock payoff has returned 4200%. It's just a shame I only put in about 6k. But there's nothing I'd try and bet the ranch on for a quick and absurd payoff. We'll get there no problem with holding long and strong on everything.

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