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A long time ago, I worked for a company called MarinSoftware (MRIN). When I left, I bought whatever shares I had vested (it wasn't that much) thinking maybe som

A long time ago, I worked for a company called MarinSoftware (MRIN). When I left, I bought whatever shares I had vested (it wasn't that much) thinking maybe some day it'll pay off. The CEO [0] is this short little guy with a Napoleon complex and I figured if anyone could extract value from this business, he could. Eventually, the company went public and the stock performed as expected... it went to shit. This could be due to the company never actually realizing a profit, but who knows. Having worked on the inside, I knew that the technology stack was shit and the engineers working on the system were subpar. For example, the CTO hired his cousin. Since the stock was under water, I held onto it for a a number of years (10?). My internal reasoning was that I wanted to wait until it got as close to zero as possible before selling so that I could maximize my tax loss. Yea, right. Suddenly, in the middle of covid, the reddit "investors" decided to randomly start to pump the stock [1]. It really came out of nowhere and I was kind of lucky to have checked the stock price. Jokingly, I set my limit order for 25 and left it there. A day or two later, I got notified that all of my shares had sold. Thanks WSB! [0] https://finance.yahoo.com/news/marin-software-inc-ceo-christopher-210845243.html https://finance.yahoo.com/news/marin-software-inc-ceo-christ... [1] https://investorplace.com/2021/07/mrin-stock-why-reddit-investors-are-sending-marin-software-higher-today/ https://investorplace.com/2021/07/mrin-stock-why-reddit-inve...

reducesuffering 3y ago
> I wanted to wait until it got as close to zero as possible before selling so that I could maximize my tax loss That is... not how finance works.
- latchkey 3y ago
  > Yea, right. You're saying that to the person who literally sold the very top.
- keithalewis 3y ago
  Look into "tax loss harvesting".
  - UncleMeat 3y ago
    Outside of cases where you are trying to keep your AGI below a certain number, it is always better to have the cash than an equivalent loss, since nobody's marginal tax rate is 100%.
  - reducesuffering 3y ago
    Selling at a $0 loss is always preferable to selling at a $1,000 loss, which takes $1,000 off your income, saving a marginal 43% rate of $430. You still lose $570. Tax loss harvesting is about capturing the loss and immediately moving into similar assets, so you book the income tax reduction now and postpone your eventual lower base sale. That is useful for things like similar ETF's, not unique assets like Marin Software equity.
    - xboxnolifes 3y ago
      They said maximize tax loss, not minimize losses. They also said it jokingly.

reducesuffering 3y ago

> I wanted to wait until it got as close to zero as possible before selling so that I could maximize my tax loss That is... not how finance works.

latchkey 3y ago
> Yea, right. You're saying that to the person who literally sold the very top.
keithalewis 3y ago
Look into "tax loss harvesting".
- UncleMeat 3y ago
  Outside of cases where you are trying to keep your AGI below a certain number, it is always better to have the cash than an equivalent loss, since nobody's marginal tax rate is 100%.
- reducesuffering 3y ago
  Selling at a $0 loss is always preferable to selling at a $1,000 loss, which takes $1,000 off your income, saving a marginal 43% rate of $430. You still lose $570. Tax loss harvesting is about capturing the loss and immediately moving into similar assets, so you book the income tax reduction now and postpone your eventual lower base sale. That is useful for things like similar ETF's, not unique assets like Marin Software equity.
  - xboxnolifes 3y ago
    They said maximize tax loss, not minimize losses. They also said it jokingly.