Did anyone Tax Loss Harvest this past week?

[VentAlarm]

I did my first TLH this week. The more I’m learning, the more I’m leaning towards a more globally diversified portfolio, so I swapped out about 25k of VTSAX for VTWAX and got around 4500 in losses.

[TheDangerZone]

That must be exhausting.

You know what they say.. personal finance is truly personal.

I TLH'd VFIAX to VTSAX and tomorrow will TLH to VLCAX. I checked today and have about 25k that I can harvest. That's 25k in capital gains I can offset in the future, not exactly chump change IMO. Two partners is about as far as I'll go. I think I can actually TLH back to VFIAX in a few weeks if needed.

[CordMcNally]

I did VSIAX, VTIAX, VTSAX to VLCAX. I’ll probably see where the market is at in a month and try to TLH back into them or just start contributing back into those funds.

[The White Coat Investor]

I did, and I will admit to a self-own. I sold one ETF yesterday morning, and then when I put in the limit order for the TLH partner, I set the price too low because I didn’t want to pay the high bid-ask spread. Most of us know what happened the rest of the day. I won’t say how much $ that cost me by the time I replaced the order, but it was enough to make me want to punch the wall.

Hopefully others will learn from my own goal. I dislike trying to buy and sell ETF’s when the market is really volatile. In the future I will just eat the spread.

I stopped using limit orders a while ago. The Vanguard and iShares ETFs have such high trading volume it's basically instantaneous anyway.

[The White Coat Investor]

Tax loss harvested again today. I bet I have tax losses larger than my Roth IRA at this point. Too depressed to add them all up but if I can't find something to use them on besides that $3K a year deduction I'm going to have to live forever to use them all up.

[VentAlarm]

Tax loss harvested again today. I bet I have tax losses larger than my Roth IRA at this point. Too depressed to add them all up but if I can't find something to use them on besides that $3K a year deduction I'm going to have to live forever to use them all up.

Is that because you donate your appreciated shares?

[The White Coat Investor]

Is that because you donate your appreciated shares?

Yea. But I think it could come in handy if I ever sell my house, WCI, other businesses, or perhaps even some real estate investments.

But if you keep your basis high in your taxable account, then you don't need a lot in losses to offset the gains of a very large amount of spending. For example, let's say I get $500K in losses. And I have a $5 million taxable account that is 90% basis. I could get $5 million out to spend without paying any taxes. Even if it was just 50% basis, I could spend a million without paying any taxes.

Just added up the losses I've been carrying forward plus what I have taken already this year. I have about $800K in losses saved up. I see another $79K in unrealized losses sitting there right now too. It's good to have them when you need them, but if all I could use them for was the $3K a year thing, I would have stopped a long time ago.

The portfolio is currently 87% basis. So continually raising the basis by donating appreciated shares instead of cash can make a big difference. Imagine how high that basis would be if I hadn't been tax loss harvesting to lower it.

[Larry Ragman]

Yea. But I think it could come in handy if I ever sell my house, WCI, other businesses, or perhaps even some real estate investments.

This is how I look at it too. Not in WCI’s weight class, but I have about $150k in losses banked. I’d like to get that up high enough to cover the gains when I sell my rental properties. But I still don’t TLH losses < 5 figures. I don’t want to track that closely. But this down market should help!

[The White Coat Investor]

Well, that’s easy to say in hindsight I guess. But I’d hate to miss out on capturing more losses if the market rebounds.

Just be careful not to turn qualified dividends into ordinary dividends with all that frenetic activity.

[Tim]

Well, I go nuts if a rebound passes and there are thousands of dollars in losses that I could have harvested against a future capital gain but missed out on. Why pay more taxes in the future than you have to? That's what drives me crazy.

Probably not going to move the needle.
You are only going to pay the tax later or your heirs get the step up in basis.

For you, the benefit is the $3k deduction currently. Yes the basis is lower for that future capital gain. Higher capital gain in the future offset by your carry forward. The point is the tax timing benefits are limited to $3k.

That thousands of dollars of rebound is realized anyway, right? Nets to zero. Obsession with TLH on the rebound is misplaced. It is timing, $3k per year.
Assumption, only referring to portfolio.

[xraygoggles]

I TLH some VTI last week in order to offset the expected tax hit from a Roth conversion I did from an old 401k I had.