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Don't spend the money before you have it in your account. It's easy to get lured into the idea that the paper money is real ("worst case, it's worth 25% of that and it's still millions!"). There are still so very many things that can wipe that out, if not to zero, to something that isn't even close to life-changing money.

Easier said than done, but really the best thing to do is focus on your current work / life. Keep saving, keep working hard, enjoy yourself the same way you have. Don't get a fancy new car that you normally wouldn't get because "soon it won't matter". Don't drain savings, don't live a lifestyle you think you'll be able to afford soon, don't shop for houses, etc.

I haven't let it affect decisions like buying a new car. I've been looking at some houses, but just for fun.

I've been working on some of my own startups since I quit this job. I needed to keep my burn-rate low, so I lived in some very cheap countries in South America, South-east Asia, and/or Europe. Basically the "digital nomad" thing, except I didn't move around very much.

And then I somehow managed to find a long-term client, where they only need me to work 4 hours per week, at $150 per hour. This supports a very high standard of living in my current country, so I'm extremely happy with this arrangement. I stumbled into this completely by accident, and I never even knew it was possible. So now I'm thinking that this is a pretty good backup plan, and I've started to put down roots here.

I know this particular gig won't last forever, but I certainly don't want to go back to full-time employment. 20 hours per week would be hard enough.

I do need to keep working hard on my own projects. I still haven't been able to build something that generates passive income. Not even regular income.

I try to make a lot of time for fun projects and hobbies that don't make any money. Things like art and music, and making things. I know it's possible to have a career as an artist or a musician, but I don't think I'm that lucky. I wish I could really pour all of my energy and time into those things, instead of also spending time trying to monetize various apps and websites.

I might try Patreon. I already have some pretty popular YouTube videos, so I think there is an audience for the kind of projects that I love to build. That's what I would be doing if I was retired, so maybe Patreon can help me to do that right now. I might try to set that up when I finish my next project.

I'm about to embark on almost the same path you did, leaving my job and moving somewhere cheaper to reduce burn rate while working on my own projects.

Would you mind if I picked your brain on which countries/cities you'd recommend? I've found info online (e.g. internet speeds listed on nomadlist) to contradict my real world findings, so would be great to get some first hand info.

Can you email me at hello.hnthrowaway@mailhero.io? If you'd prefer me to get in touch another way let me know. Or even a reply here would be hugely useful.

Sure, I can relate :). Have a few thoughts:

$20k to $5-10m is incredible. That implies 250-500x valuation growth (for example you joined at series A with $20m valuation and the company is worth $10b), which means you hit a unicorn within the unicorns!

Was the company QSBS-eligible when you exercised? There are huge potential tax savings there.

Your shares were NSOs, correct? There are weird potential issues with 83bs and vesting ISOs.

It's worth thinking through how to factor your paper money into your investment portfolio. You could model it as $0 and have an otherwise standard asset allocation (e.g. whatever WealthFront recommends for your risk profile). Alternately you could include it as a huge illiquid stake in a US tech company -- as if your portfolio was 80% in GOOG -- and mitigate your overexposure in the other 20%. Or something in between.

Yes, I was very lucky. I was actually one of the first few employees, and I joined about a year before they raised their series A. Now they are a unicorn, and hopefully on their way to an IPO.

I don't know if I would say I joined a "unicorn within unicorns". Every unicorn has at least 10 early employees with the same story, and according to this list [1], that's at least 1,850 people.

I don't think the company was QSBS-eligible. At least, I've never heard that acronym while reading through all of the paperwork. And yes, the shares were NSOs.

I don't really have an investment portfolio, apart from these shares. I've been working as a part-time freelancer while I try to build my own startup ideas, so I'm not really saving for retirement. The IPO should only be a few years away, so I'm just going to wait and see what happens.

If everything falls apart, I'll try a few more startup ideas. If those fail, my backup plan is to spend 4 years working full-time, living frugally and saving as much money as possible, and then retiring in a country with a very low cost-of-living. I can save around $130k per year as a remote software engineer, and I only need $500k to retire comfortably.

[1] https://www.cbinsights.com/research-unicorn-companies

You should read more about QSBS: http://www.andersentax.com/services/for-private-clients/busi...

Under certain circumstances, QSBS (Qualified Small Business Stock) rules will significantly decrease your tax burden.

QSBS is a tax thing, not a specific company thing. On the face of it (tech company, exercised very early) it seems like you'd be eligible. The company lawyers should be able to tell you the QSBS eligibility period (something like "options exercised before MM YYYY, when TECH CORP's gross assets exceeded $50 million")

> IPO in the next few years.

Been there, done that. A startup I had exercised my options in was bought out by a company that was "talking about an IPO in the next few years".

That was several years ago.

The execs and VCs in the original startup got almost all the money in the liquidity preference. Ironic because I did "rock the boat" when I joined by attempting to ask for a better share class. 23 year old me asking for preferred shares lol. It failed.

The bigger company doesn't seem to be in IPO mode anymore. But I have shares of it, with a notional value 1/8th of what I paid to exercise my options.

> Sometimes I can make it a whole day without thinking about it, but it feels like I'm just burning time until I can finally cash in these shares and never worry about money again.

I can relate to that too, for other opportunities, its always good to look forward to something.

I had something similar - except we sold our company to another company, part cash part stock. Over the years we heard through the press that that other company was doing very well, so figured our shares were gaining some real value. Then out of nowhere they sold to an even bigger company, cool... but for a pretty disappointing number, and I got like 50k. The press was all BS to try to drive more funding/etc.

I think your situation is astonishingly rare.

Nope. Congratulations on winning the lottery!