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I personally think it’s better to struggle early on than to give away money like candies to founders with dubious businesses who will then trick gullible employ

I personally think it’s better to struggle early on than to give away money like candies to founders with dubious businesses who will then trick gullible employees into thinking that these companies’ massive valuations mean anything. I kid you not one founder told me once my equity was safer in the company than liquidated and put in the SP500, when I inquired about tender opportunities. I have vested equity (that I painfully exercised) in a “2020-era unicorn” that has been a complete zombie ever since. I wish they’d just go out of business for me to at least declare a capital loss on my taxes. I just have myself to blame clearly, so just stating an opinion.

toomuchtodo 1y ago
You want to sell that equity to create a loss? If it’s worth zero, I’m happy to go through the exercise if it’s marketable. This offer is only good if it’s actually worthless and I’m not stiffing you on the value.
- parrit 1y ago
  Could you structure a contract where you buy it for $1 and sell it back the next day for $1?
  - remyp 1y ago
    I could be misunderstanding, but this sounds like it would be a wash sale, which would prevent the seller from claiming the loss on their taxes. https://www.investopedia.com/terms/w/washsale.asp https://www.investopedia.com/terms/w/washsale.asp
    - parrit 1y ago
      Oh yeah! Get a lawyer. But then that's expensive. Might as well just leave it be and hold the shares.
  - toomuchtodo 1y ago
    I would simply hold it until the value goes to zero. In the event enterprise value doesn’t go to zero, I would gift any gains back to OP after taxes (because I’m trying to do them a favor, not make an investment).
bruce511 1y ago
>> I personally think it’s better to struggle early on than to give away money like candies to founders I agree, and disagree. My business was bootstraped, we never took outside investment, and it succeeded and makes money. It employs 50 odd people and is a big fish in a fairly small pond. We make the world better for a few thousand people (customers). But our approach couldn't lead to a Facebook, or Amazon or Uber etc. Products like that work best once they achieve scale, and achieving scale is expensive. But Uber (goes example) works poorly with 50 drivers in 1 city. For most businesses and most founders, more is achieved with less. Most businesses don't need scale to be effective. But equally, the VC approach is necessary for some subset of problems.
- kayovin1 1y ago
  Great to hear about your company Bruce We will see stories like this appreciated more than VC-backed startups as it's simply more sustainable and impactful
- solardev 1y ago
  Well said. > For most businesses and most founders, more is achieved with less. Most businesses don't need scale to be effective. I wish more businesses thought this way.

toomuchtodo 1y ago

You want to sell that equity to create a loss? If it’s worth zero, I’m happy to go through the exercise if it’s marketable. This offer is only good if it’s actually worthless and I’m not stiffing you on the value.

parrit 1y ago
Could you structure a contract where you buy it for $1 and sell it back the next day for $1?
- remyp 1y ago
  I could be misunderstanding, but this sounds like it would be a wash sale, which would prevent the seller from claiming the loss on their taxes. https://www.investopedia.com/terms/w/washsale.asp https://www.investopedia.com/terms/w/washsale.asp
  - parrit 1y ago
    Oh yeah! Get a lawyer. But then that's expensive. Might as well just leave it be and hold the shares.
- toomuchtodo 1y ago
  I would simply hold it until the value goes to zero. In the event enterprise value doesn’t go to zero, I would gift any gains back to OP after taxes (because I’m trying to do them a favor, not make an investment).

bruce511 1y ago

>> I personally think it’s better to struggle early on than to give away money like candies to founders I agree, and disagree. My business was bootstraped, we never took outside investment, and it succeeded and makes money. It employs 50 odd people and is a big fish in a fairly small pond. We make the world better for a few thousand people (customers). But our approach couldn't lead to a Facebook, or Amazon or Uber etc. Products like that work best once they achieve scale, and achieving scale is expensive. But Uber (goes example) works poorly with 50 drivers in 1 city. For most businesses and most founders, more is achieved with less. Most businesses don't need scale to be effective. But equally, the VC approach is necessary for some subset of problems.

kayovin1 1y ago
Great to hear about your company Bruce We will see stories like this appreciated more than VC-backed startups as it's simply more sustainable and impactful
solardev 1y ago
Well said. > For most businesses and most founders, more is achieved with less. Most businesses don't need scale to be effective. I wish more businesses thought this way.