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It's fun to think about. I think it would be hard to make the most of the money and have a great lifestyle while keeping a low profile and not getting caught.

It costs a lot less than $10M if you want to move to Thailand and live off-grid in some remote area. You can probably do that for a lot less than $100,000, including a Thailand Elite Visa. If that's part of your plan, then just hold onto the money and earn interest, or maybe give it back and hope for a reward. Or just save up the money normally, it's not that much.

I wonder if it's still possible to change your identity in a developed country. Maybe you could move to a new country and start using a fake passport to establish your new identity over time. But I think that stopped being possible sometime in the 90s or early 2000s.

I found it stressful enough just to move to a new country and get a visa legally. I can't imagine also worrying about getting extradited and sent to prison at any moment. Sounds like a terrible life. I wouldn't keep the money.

EDIT: Just reading some of the other replies, and wow, there are some genius criminals in here. Maybe I would take the money!


SharesPost might be able to offer a similar loan [1]. Also have a look at Equidate and EquityZen.

[1] https://www.businesswire.com/news/home/20180117005389/en/Sha...


Yes, right now I'm feeling trapped by "option paralysis", and I'm actually looking for some help to untangle a very complicated situation [1]. I'm very fortunate to be a professional software developer with a growing company, and a lot of different opportunities. But I actually have too many choices, and too many different factors to consider. I'm not sure how to organize everything and make a decision.

[1] https://news.ycombinator.com/item?id=19659912


Interesting, thanks very much! I will have a look at these blog posts.


If you do end up going through it, shoot me an email. There's other follow up material around the subject. I don't list it here because its easy to get lost in the details when starting. Simon is the source of it all and the genesis.


I have a very similar story: Was on the first 10 employees at a now unicorn, forward exercised with a few thousand dollars, and my shares are also now worth around $1.5m. But unfortunately the company blocked all attempts at selling any shares on secondary markets.

Something you might not be aware of: If you joined the company before they had $50M in assets, your stock would also qualify as QSBS [1], which means you don't have to pay any tax on gains of up to $10 million.

[1] https://www.andersentax.com/services/for-private-clients/bus...


I was one of the first 5 employees at a YC unicorn. They haven't had an IPO yet, but it's getting closer. My original offer was for 0.5% of the company, but I didn't vest all of my shares before leaving. The shares are currently worth about $1.5M, and I'm hoping that they will be worth about $3-5M after the IPO and lockup period.

My salary was $120K and I relocated to SF from a different country, so I don't really feel like I took a pay cut. But the cost of living was extremely high, so the money didn't go as far as I thought it would. Especially because my spouse wasn't able to work on a dependent visa.


https://www.youtube.com/watch?v=TYt5yuiGk9E&feature=youtu.be...

Minor frustration: Someone in the <5 employee count deserves more equity. Yes that % is pretty common, but I think that's wrong.


Thanks, that was a great video!

I actually think the 0.5% was very fair, or even generous. I didn't have much startup experience before that, and it was my first "real" job. They were also taking a big gamble with the relocation and immigration lawyer fees.

The other thing is that more equity probably wouldn't have motivated me to stay longer, unless I was a cofounder. I really didn't enjoy working for the company. I felt like I didn't really have any impact on anything, the company didn't really need me, and I just didn't like the company culture very much. So I tried to estimate how many shares I would need to hit my early retirement target ($3M), and I left after I had vested enough shares.

I knew that the company would be very successful, and I left a huge amount of money on the table, but I have zero regrets. I've been much happier since I left, and it's been much more fun to work on my own startups.


I'm a non-US citizen who moved to San Francisco to work for a startup. I left that job (and the US) many years ago, but that startup is now a unicorn, and they're very close to an IPO.

I believe that if I become a tax resident in Hong Kong, Singapore, Belgium, etc. then I won't need to pay any capital gains tax when I sell my shares. I've heard that California will go after people who try to move to other states to avoid CGT, but I don't know if that applies to non-US citizens who have left the country. (Please let me know if you can recommend a good international tax expert.)

I've been living in many different countries since I left the US, so I don't have any strong ties to any specific countries (not even my home country). My shares could be worth about $5M after the IPO. If I wanted to sell most of them and buy VTSAX, then I might end up with a tax bill of $1.5M if I happened to live in a country with a 30% CGT (or if capital gains are treated the same as income.)

I don't think it's unethical for me to become a tax resident in some country with no capital gains tax. The alternative is paying a huge amount of money to some random country just because I happened to live there over 183 days.

I wouldn't mind moving back to California and paying the tax like everyone else, but it's impossible. There's no visa for people who do freelance work while building a bootstrapped startup. Even if I wanted to go back to a full-time job, it's extremely difficult to get an H-1B or O-1 visa. My startup would need to have at least $100k in ARR before I meet the salary requirements for an H-1B visa. I'd also need to take some investment so that my investors could be on the board and sponsor my H-1B application. My company is already making $50K ARR. I enjoy being independent and going at my own pace, so I don't really need any investors. (EDIT: I just learned about the E-2 and L-1A visas. I might look into those.)

If I was still living in California after the IPO, I might end up paying $1M+ in LTCG tax when I sell my shares. I would be very happy to pay this if I could move back now, get a green card, and work on my own company. I guess California and the federal government would be making a bet based on the likelihood of an IPO, which is still nowhere near guaranteed. This is also an extremely rare situation which only applies to a handful of people. But it would be nice if I could get a green card if I promised to live in the US and pay these taxes.

The other option is to just live in Hong Kong for > 6 months, sell my shares, and pay $0 in capital gains tax. Then I can move to the US on an EB-5 visa, which only costs $500k.


Countries with no capital gains taxes (on account of capital, not income): New Zealand, Singapore, Hong Kong, Malaysia, Switzerland. There's others, of course.


New Zealand would be great, but I heard that there are some separate rules for foreign shares. Or is that only for dividends? I need to learn more about that. I saw on this Quora answer [1] that I would need to pay tax on an assumed 5% dividend each year. So if I was holding $5M in shares, then I'd have to pay tax on an assumed dividend income of $250K. But I think there are also exceptions for startups that haven't gone public yet.

Are you available for a consultation?

[1] https://www.quora.com/Im-from-New-Zealand-but-I-own-a-lot-of...


> Kaggle, which has about half a million data scientists on its platform, ...

Are there really that many data scientists? I thought it was a niche specialty. Is there enough work for that many people?


Think they maybe put a 0 in the wrong spot. Kaggle's leaderboard only shows ~50k: https://www.kaggle.com/rankings


I think they mean unique users.


A lot of them are academics who participate out of interest, and I'm sure a significant amount are regular software engineers trying to get their hands dirty with ML.


What do you mean by this?


Oh crap. I've entered my banking password into Transferwise quite a few times.

Welp, time to change all my passwords.


> Welp, time to stop using the same password for multiple services.

> Welp, time to start using a password manager.

FTFY


OP isn't saying they used the same password for transferwise as for their bank. Transferwise allows you to log into your internet banking and authorize a transaction through their site. You actually give them your internet banking password, regardless of how you log into their site.

Which is pretty strange in itself, to trust a 3rd party with your internet banking password, but that's how it works.


This is the main reason I've never used Mint.


Folks should review their banks' policies before doing this.

For example Bank of America won't hold customers liable for fraudulent transfers or bill pay transactions through their website, but sharing your online ID and password seems to void that protection.

https://www.bankofamerica.com/onlinebanking/online-banking-s...


Yes, definitely a good suggestion.

I already use Lastpass, which makes regenerating all my passwords a little easier.


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