080 - What Tax Investment Strategies Should I Be Aware of When Selling Stock Options
12/30/20 • 25 min
In this episode of the podcast, we have a listener question:
Just heard your podcast on the target date funds and really appreciate the insight as I'd just rebalanced my 401k and pulled out of them because of the fees and my level of attention to my portfolio. From a financial management perspective, I'm a DIY-er with a blend of Boglehead and FIRE, philosophically. Currently 1/3 of my wealth is concentrated in RSU/stock options from my company as part of my annual compensation package. Is there a tax strategy in regard to timing and/or amount to sell my options to ease the tax burden?What are some options that would make sense to reallocate the funds from the sales? My wife has an annuity in her 403b, which I've heard/read is not a great idea, so can you explain under what circumstances an annuity is or isn't a good option?
Planning Points Discussed
- Tax Planning
- Stock Options
- Annuities
- Restricted Stock Units (RSU)
- Other issues (IRAs, Vesting Schedules, Financial Goals)
Timestamps:
3:45 - Restricted Stock Units
4:19 - Tax Planning of Stock Options
10:00 - Vesting of RSU
16:06 - Deciding When Best To Sell For Your Goals
20:15 - Why Should I Invest In An Annuity?
LET'S CONNECT!
James
Scott
ENJOY THE SHOW?
Don’t miss an episode, subscribe via iTunes, Stitcher, Spotify, or Google Play.
Leave us a review on iTunes.
Have a money question you want us to answer? Submit one here
In this episode of the podcast, we have a listener question:
Just heard your podcast on the target date funds and really appreciate the insight as I'd just rebalanced my 401k and pulled out of them because of the fees and my level of attention to my portfolio. From a financial management perspective, I'm a DIY-er with a blend of Boglehead and FIRE, philosophically. Currently 1/3 of my wealth is concentrated in RSU/stock options from my company as part of my annual compensation package. Is there a tax strategy in regard to timing and/or amount to sell my options to ease the tax burden?What are some options that would make sense to reallocate the funds from the sales? My wife has an annuity in her 403b, which I've heard/read is not a great idea, so can you explain under what circumstances an annuity is or isn't a good option?
Planning Points Discussed
- Tax Planning
- Stock Options
- Annuities
- Restricted Stock Units (RSU)
- Other issues (IRAs, Vesting Schedules, Financial Goals)
Timestamps:
3:45 - Restricted Stock Units
4:19 - Tax Planning of Stock Options
10:00 - Vesting of RSU
16:06 - Deciding When Best To Sell For Your Goals
20:15 - Why Should I Invest In An Annuity?
LET'S CONNECT!
James
Scott
ENJOY THE SHOW?
Don’t miss an episode, subscribe via iTunes, Stitcher, Spotify, or Google Play.
Leave us a review on iTunes.
Have a money question you want us to answer? Submit one here
Previous Episode
079 - 4 Steps to Implementing Change
In this episode James and Scott discuss their thoughts on how they implement change in both their personal and financial lives.
It’s well known that just because something is simple doesn’t mean it will be easy. There are four questions to ask yourself when it comes to achieving your goals, both personally and financially. 1) What can you do? 2) How will you do it? 3) When will you do it? 4) Who can hold you accountable along the way?
Planning Points Discussed
- Accountability Partners
- Prioritizing Your Goals
- Purchasing Large Investments
- Aligning Your Investments with Financial Goals
Timestamps:
2:45 - Simple Doesn’t Equal Easy
6:15 - Avoiding Barriers
7:30 - Examples of Implementing Change
9:30 - Having an Accountability Partner
12:20 - Advisors Have Financial Advisors
12:50 - Aligning Your Money With Your Life
LET'S CONNECT!
James
Scott
ENJOY THE SHOW?
Don’t miss an episode, subscribe via iTunes, Stitcher, Spotify, or Google Play.
Leave us a review on iTunes.
Have a money question you want us to answer? Submit one here
Next Episode
081 - What Should I Do When I Receive a Windfall?
In this episode of the podcast, we have a listener question:
I am about to come into a decent sum of money from selling a rental property. I’m 30 years old, invest 22 percent into my 401k (that has a balance of 45k currently). My plan was to invest this money in a total market index fund and an international index fund. Is this my best option? I also have a house that I owe about 215k on. Thank you in advance!
Planning Points Discussed
- Tax Planning
- Investment Strategy
- Real Estate
- Asset Allocation
- Other Issues (Emergency Fund, Financial Goals, Estate Planning)
Timestamps:
1:00 - Shoutout to the Listener Question
5:00 - When Should I Start Investing After Receiving A Large Sum?
6:20 - When Does A 1031 Exchange Make Most Sense?
7:35 - Where To Start When Making An Investment Plan?
8:18 - Refinancing Your Home & Interest Rates
12:05 - Having An Emergency Plan
LET'S CONNECT!
James
Scott
ENJOY THE SHOW?
Don’t miss an episode, subscribe via iTunes, Stitcher, Spotify, or Google Play.
Leave us a review on iTunes.
Have a money question you want us to answer? Submit one here
If you like this episode you’ll love
Episode Comments
Generate a badge
Get a badge for your website that links back to this episode
<a href="https://goodpods.com/podcasts/real-personal-finance-113622/080-what-tax-investment-strategies-should-i-be-aware-of-when-selling-s-10740059"> <img src="https://storage.googleapis.com/goodpods-images-bucket/badges/generic-badge-1.svg" alt="listen to 080 - what tax investment strategies should i be aware of when selling stock options on goodpods" style="width: 225px" /> </a>
Copy