40 year corporate finance career in Corporate Finance with Fortune 500 companies including UnitedHealth and ING. Focus on insurance lines including annuities, life and health. Now retired.
When I was laid off in the 2009 recession I said I wanted to work for myself. I plunked down $40K in a financial services franchise and it was a disaster. Plus I wasted time. I did feel more grateful getting back to working in Fortune 500 businesses again.
I wanted to get into direct indexing in my taxable account to benefit from tax loss harvesting opportunities as you state. My issue, which you also mention, is rotating out of a reasonable portion of my taxable portfolio will leave me with sizable taxable gains. Also, I’m retired, so not producing new savings to invest.
“A booming stock market has made the tax bomb significantly worse.” I’d argue this has made things better. Sure, we want to minimize our marginal tax rate but still, the more gains the better. Nonetheless-great article! Great considerations. Thanks
Comments
I don’t get that. Are you going on vacation and bringing back that much?
Post: Market Turmoil by Dennis Friedman
Link to comment from April 12, 2025
Do all of you think, with interest rates up/bond prices lower, tweaking a bond portfolio to longer duration bonds makes sense at this time?
Post: First Quarter 2025 by Ken Cutler
Link to comment from April 12, 2025
I captured the bit of tax loss harvesting I could yesterday. Besides that, staying the course as it looks most of you are. Best of luck to all of us.
Post: Tariffs and our retirement assets
Link to comment from April 5, 2025
When I was laid off in the 2009 recession I said I wanted to work for myself. I plunked down $40K in a financial services franchise and it was a disaster. Plus I wasted time. I did feel more grateful getting back to working in Fortune 500 businesses again.
Post: My Mistakes by Jonathan Clements
Link to comment from February 22, 2025
David - more aggressive than I expected to hear but you’ve probably done well so far.
Post: Any Crypto Investors?
Link to comment from February 20, 2025
Well you’ve probably done quite well so far.
Post: Any Crypto Investors?
Link to comment from February 20, 2025
Do you pay an AUM fee? If so, how much? Thanks
Post: Investing in Dimensional Funds
Link to comment from February 17, 2025
Wow - don’t know how else to respond
Post: A matter of significant financial concern – want fries with that?
Link to comment from February 17, 2025
I wanted to get into direct indexing in my taxable account to benefit from tax loss harvesting opportunities as you state. My issue, which you also mention, is rotating out of a reasonable portion of my taxable portfolio will leave me with sizable taxable gains. Also, I’m retired, so not producing new savings to invest.
Post: One Stock at a Time
Link to comment from February 17, 2025
“A booming stock market has made the tax bomb significantly worse.” I’d argue this has made things better. Sure, we want to minimize our marginal tax rate but still, the more gains the better. Nonetheless-great article! Great considerations. Thanks
Post: Trouble Ahead
Link to comment from February 8, 2025