Quote from @Josh St Laurent:
@Tom Server
Hello Josh, thanks for the reply. I did not sell the stock yet. The company stocks were purchased with ESPP and RSU thru computershare. I also have company stock thru Voya as a 401k match. With the computershare I could see the blocks of stocks that were purchased from 1999 to 2023. With the Voya 401k it does not show a block of stocks but just a amount of shares.
Well, that opens Pandora's box when it comes to tax consequences/strategy. I'll double down on talking to a CPA because this is absolutely a situation where if you're strategic it'll make a world of difference. I'll try to be helpful and concise here without being too long-winded...
ESPP - Typically you buy this at a discount (Usually 15%) typically you get beneficial tax treatment on the discount and won't have to pay income tax on it as long as you hold it for their required holding period. (Usually 2 years from the offering date and 1 year from the purchase date). If you meet the holding period you will only pay LTCG (long-term capital gains) on any growth.
RSUs - A bit simpler, when your RSU shares vest they will move into your brokerage account and that will trigger income tax on the value of the shares. Essentially at that moment you own them outright and could sell them without additional tax. Now that you've been holding them what you have to think about is how long you've owned them. If it has been over a year you would only need to pay LTCG (15% for most) ONLY on the gains since your shares vested.
Stock in 401k - Believe it or not, this may be the most complicated holding you have. Shares in a 401k are not usually shares, typically they are what's called a Unitized Stock Fund. If you no longer work for the company you can take advantage of a concept called NUA (Net Unrealized Appreciation). This involves rolling your shares from your 401k into a brokerage account (Taxable event and potentially a 10% penalty if you're under 59.5 y/o). Here is where the strategy comes in:
When you move 401k stocks to a brokerage account via an NUA transaction, you pay income tax on the cost basis (And maybe a 10% penalty) but NOT on the gains until you sell. When you do sell you'll pay LTCG on the growth EVEN IF you haven't held it in that brokerage for a year. This type of strategy works really well for people who worked at a company for a long time and whose stock did incredibly well.
These are concepts even financial advisors get tripped up on so feel free to clarify anything that doesn't make sense or if you want to give more specifics I can give examples and math.
Josh thank you for taking the time to explain the different options. Yes I've been at the company for for 24 years and yes had the shares do well over the course of the 24 years. I started purchasing the stock in 1999 for around 50 dollars a share and it had a high of 230 a share about 2 years ago..Now its currently at 154 mark..
I left this job 2 years ago and just now rolling over the 401k funds over to my new companies 401k account. I still kept the stock portion of the 401k in the old account.. Just cause the stock dropped a lot over the course of the last 2 years. When I look at the stocks in the 401k account, I don't see a cost basis??.. i just see the total amount of shares and the value of it. Maybe I need to do some more digging.
In my companies stock account I do see all the different buckets of prices I purchased the stock at.
To really get a understanding of the situation.. It just happened that im in the process of purchasing 2 properties this month. 1 is a rehab, that I plan on keeping for my self for a bit then selling.. the other is an invest property non owner occupied thats a 3 family
The rehab I need to purchase out cash 105k and another 15k-20k to repair
The rental property I need to put 25% down and closing is around 70k
So I need 175k to purchase and another 30k to repair both properties
I have 90k in liquid in a savings account, 230k in a 401k made up of the funds and stock
and about 330k in my companies stock account..
My plan was and not sure if this is the smartest way .. hence why I'm asking here!
90k liquid + 50k 401k loan + 35k sell company stock ...the other 30k to repair maybe HEL or LOC
I made an error thinking i could borrow up to 50% of my 401k but found out it maxed 50k so now i have to sell the stock to make up the differences
There other issue is the repayment of the 401k its has to be paid back to myself in 5 years.
So the other idea is after everything is said and done.. take a loan out repay 50k and rebuy the stock.. and have like a 10 or 15 year loan to pay it back
Thank you for listening