Search found 10 matches

by patient_investor
Tue Jun 06, 2017 11:54 am
Forum: Personal Finance (Not Investing)
Topic: Best credit card for cash back
Replies: 104
Views: 19959

Re: Best credit card for cash back

There are possibly better "rewards" options out there if you're willing to spend your time to game redemptions, but, from what I could find, the simplest no fee / high return straight cashback 2-card only setup is the following: Bank of America Travel Rewards - 2.625% flat cash back / no fee. Bank o...
by patient_investor
Mon May 22, 2017 8:52 pm
Forum: Investing - Help with Personal Investments
Topic: Is Schwab Intelligent Portfolio OK for taxable accounts???
Replies: 33
Views: 3125

Re: Is Schwab Intelligent Portfolio OK for taxable accounts???

I was offered this service after opening Schwab Brokerage account. Declined. The biggest problem I see is the presence of "Fundamental" ETFs in the mix. Fundamental ETFs: - are more expensive (0.25% vs 0.04% on average I think) - have wider trading spreads (very few trade them as, honestly...
by patient_investor
Mon Mar 20, 2017 9:00 pm
Forum: Investing - Help with Personal Investments
Topic: facing unexpected capital gains - tax loss harvesting options...
Replies: 44
Views: 2231

Re: facing unexpected capital gains - tax loss harvesting options...

Everyone, thank you for your replies ! Again, I wanted to clarify - this post is more about tax deferral rather than stock picking. I think tax deferral is very consistent with the forum's "max out 401K" philosophy. Stock picking here is a one-year event out of necessity to enable tax defe...
by patient_investor
Sat Mar 18, 2017 10:02 pm
Forum: Investing - Help with Personal Investments
Topic: facing unexpected capital gains - tax loss harvesting options...
Replies: 44
Views: 2231

Re: facing unexpected capital gains - tax loss harvesting options...

So now, rather than pay the taxes on some short term capital gains, you're talking about levering up 2x to 3x. What could possibly go wrong? Picking up nickels in front of a steam roller. As I said above, the best I can do is to sell S&P index from 401k/IRA to offset this S&P-like manufactu...
by patient_investor
Sat Mar 18, 2017 9:59 pm
Forum: Investing - Help with Personal Investments
Topic: facing unexpected capital gains - tax loss harvesting options...
Replies: 44
Views: 2231

Re: facing unexpected capital gains - tax loss harvesting options...

I normally don't use margin except for making sure my checks don't bounce, but this is going to be a very short term loan and my margin rates have been negotiated down. How do you know it will be short term? What happens if the portfolio of stocks have mostly gains between now and 12/31 - are you g...
by patient_investor
Sat Mar 18, 2017 9:25 pm
Forum: Investing - Help with Personal Investments
Topic: facing unexpected capital gains - tax loss harvesting options...
Replies: 44
Views: 2231

Re: facing unexpected capital gains - tax loss harvesting options...

So, let's say you have $100k in gains from the employer stock. And, let's say you are trying to offset $50k of those gains with losses from your proposed approach. Assuming you will try to mimic the S&P500 (or another index) to create your own basket of stocks, and make about 8% on your basket ...
by patient_investor
Sat Mar 18, 2017 8:36 pm
Forum: Investing - Help with Personal Investments
Topic: facing unexpected capital gains - tax loss harvesting options...
Replies: 44
Views: 2231

Re: facing unexpected capital gains - tax loss harvesting options...

How much of your portfolio are we talking about? How much can you risk on this TLH experiment? Since you are essentially playing with "house money" that you are losing to taxes, you could liquidate the company stock and simply invest in a portfolio selected to mimic the S&P500 (or som...
by patient_investor
Sat Mar 18, 2017 8:28 pm
Forum: Investing - Help with Personal Investments
Topic: facing unexpected capital gains - tax loss harvesting options...
Replies: 44
Views: 2231

Re: facing unexpected capital gains - tax loss harvesting options...

How much of your portfolio are we talking about? How much can you risk on this TLH experiment? Since you are essentially playing with "house money" that you are losing to taxes, you could liquidate the company stock and simply invest in a portfolio selected to mimic the S&P500 (or som...
by patient_investor
Sat Mar 18, 2017 5:00 pm
Forum: Investing - Help with Personal Investments
Topic: facing unexpected capital gains - tax loss harvesting options...
Replies: 44
Views: 2231

Re: facing unexpected capital gains - tax loss harvesting options...

Thank you for all your thoughts. Let me clarify your questions so far. 1. Without going too deeply into vesting schedules - yes, most of the capital gain is short term and substantial due to "above market" acquisition price. All numbers are approximate but not far from reality. 2. 45% come...
by patient_investor
Sat Mar 18, 2017 1:04 pm
Forum: Investing - Help with Personal Investments
Topic: facing unexpected capital gains - tax loss harvesting options...
Replies: 44
Views: 2231

facing unexpected capital gains - tax loss harvesting options...

Hello, This is my first post but I've been a long time reader. Looking for advice. Situation: My employer will be acquired this year. When this happens, I will get cash for all my company shares (both vested and currently unvested) and pay ~45% marginal tax on roughly half of proceeds. I am looking ...