Depends on what they are, if RSUs you can and should (IMO) treat as cash. There are also some tax benefits to selling at a loss, but if you’re talking a decent chunk of money you should consult an advisor.
Depends on market sentiment and if there are a lot of old investors (VCs) that want out. I good default is, 33% ASAP, 33% after 6 months, 33% in 1 year+.
Some go up, some down https://www.nasdaq.com/markets/ipos/performance.aspx?timeframe=6+months
all of this strictly depends on where the market is and where you think it’s going to be. you shouldn’t keep everything in one basket. having said that, i made over 400k this year so far by doing exactly that because i believe the ride has a small runway to continue. YMMV
i for one am watching the lyft lockout expiration with great interest. One thing I've been paying attention to recently is the trade volume. Uber's been in the neighborhood of 10M/day for the last 30 days or so and I can't imagine that several 10's of millions of shares becoming available on the day lockup expires is going to have any sort of up-lifting effect on the uber price.
Not always it just depends on the particular company's outlook etc.
All personal preference and based on what your goals are.
Goal is maximize profit and diversify
Can’t help you there. I would imagine selling when the lockout period ends isn’t a great strategy but I don’t know shit about that.