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>> 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.

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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

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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.
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Could you structure a contract where you buy it for $1 and sell it back the next day for $1?
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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

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Oh yeah! Get a lawyer. But then that's expensive. Might as well just leave it be and hold the shares.
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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).
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