RSU sale strategy after IPO lockup period expiration
My ex-company (Pinterest) IPO'ed this year and all my RSUs vested on the IPO date (mid-April-2019). This is the first time I'll be receiving a decent amount of money in bulk so I'm trying to read up on how to approach liquidating my vested RSUs. I'm hoping this thread can yield a good discussion and provide some guidance from more (fortunate and) experienced folks who may have gone through a similar process in the past.
Specifically I would like to pick your brain about how you have to plan for a tax-optimized sell strategy. Problem with RSUs is that they all vest at the same time on the IPO date (double trigger RSUs). Combined with my regular income from my current job, it results in a huge tax burden already. Also, luckily Pinterest shares are up considerably since the IPO date - keeping my fingers crossed that it stays that way since I had very low expectations from my ex-company. If I were to sell them immediately right after the IPO lockup period ends, than all the gains (assuming it stays that way) are subject to short-term capital gains tax, which is taxed at the same (very high) income tax levels.
I found a few articles from financial advisers which provide some guidance on how and when to sell. In case other people are interested here are the links:
After this long intro, finally time for questions and discussion points:
1. Selling ALL shares right after the lock-up period expiration and taking a short-term gains hit vs waiting for 6 more months to at least reduce Federal tax burden by %13 at the risk of stock price going down. How should I think about these approaches? How did you plan for it if you went thru this process before?
2. My tax situation: Don't own a home, don't plan to buy one anytime time soon where I reside (which is California), don't have kids. Is there anything that can be done about the tax burden?
3. When I eventually liquidate, my plan is to invest the gains in a simple and low-cost index fund-based diversified portfolio. Given this plan do you guys think consulting a financial adviser has any added value? Do they really provide any added gain and clever strategies to increase the value I can get out of this process?
4. Is there anything else that I should be planning for?
Thanks in advance for all your help.