l2c1928

Convinced media-bias is the only reason why anyone could be "long $LYFT." They are a text-book "one trick pony" and too late for them to catch up in food delivery, international expansion, etc.

I'm having a hard time thinking of ISAs as much more than a ridiculously high interest loan, especially for those who are self-motivated have a high probability of landing a job after doing X course.

E.g. Lambda school is $20k if you prepay and maxes out at $30k over 2 years, which is effectively a 45% interest loan. Even if you didn't have the cash (or didn't want to fork out) the cash, a typical loan taken out today will have a single digit interest rate.

Personally I'm completely happy with my federal student loan terms for the $20k or so I have left to pay. I stretched it out to 20 years, pay a 5.5% interest rate, the interest rate is deductible you make below a certain income, and barely think of it outside of doing my taxes.

I never said how many years ago I joined...by a "few years" I meant 5. I said I sold some shares via a tender offer, which are company sponsored, and last year was the first time I was offered that opportunity. Companies can't block you from selling on a secondary market unless you've specifically agreed to that as part of the initial grant. It's far more common that they have the "right of first refusal" clause which means they get the chance to buy back your shares before selling to a third party.

I don't think there's anything particularly special about my situation other than I was fortunate to join a now unicorn early on.

There's a myth that you can't realize gains if a company doesn't IPO...I've already sold some shares in a tender offer. There is an active secondary market for shares if I chose to sell more.

Not sure what your point is about $3MM over 10 years. Why would you divide it over anything other than the number of years you actually worked at the company?

You've assumed I was a senior engineering hire. I was in a junior non-technical role a year out of college.

Late stage private startups almost always grant RSUs. If they didn't it would be way too risky for most people to join because the cost to exercise would be very high.

My point is that there are ways to manage risk as an employee, such as early exercising assuming you are joining an early stage startup where the cost is low enough.

I would've been screwed if I didn't early exercise.

I paid long term capital gains after selling a portion of my private stock via a tender offer last year.

It's bad for most people, but when it's good it's really good.

I was lucky to join a now unicorn as one of the first few dozen employees a few years ago. I forward exercised with a few thousand out of pocket (section 83b) an equity grant now worth around $1.5m. Because I forward exercised my options at a low valuation I didn't have to worry about paying taxes if I exercised at a later time when the company's valuation grew. It also meant that my gains became long-term capital gains, and thus taxed lower, as soon as possible after I vested each month.