arbitrage314

From someone who works in/near the industry, I can tell you without a doubt that the best HFT strategies are the ones you never hear about.

Every sale I've done so far has been to my network of friends/colleagues. Most people are eager to get some slight financial exposure to the startup world as part of a well-diversified portfolio. There were two steps required: (1) the person I sold to had to be an accredited investor (2) I had to give the company right of first refusal (which required writing a quick letter and waiting 30 days)

Yep, that's a good point. If the startup will be less successful without you, then it's not a perfect arbitrage opportunity. This would be especially true if the company were small or starting out.

For most established companies, however, I think the difference of one person is typically quite low.

Hi giuscri! I work as a developer at a large company (e.g., think Google, Facebook, Goldman Sachs, IBM, etc.).

Hi burger_moon! There are a couple of options: 1. Attempt to sell back to the company 2. Sell your shares to an independent buyer that you've found (the company typically has right of first refusal, which just means they're allowed to outbid the independent buyer) 3. Wait until the IPO, and sell them on the open market. 4. Sell your shares on EquityZen, SharesPost, or something similar.

If you want to make "big money," you should pretty much avoid WORKING at startups at all costs. Instead, get a high-paying job at an established company, and invest the difference in the startup's equity.

I've considered lots of startup jobs because I believed strongly in the companies. Every single time, however, I was able to get a larger chunk of the company by keeping my current job and simply investing.

To give an example, my current job pays about $250k, and one year, I invested $100k of that into a startup, leaving me with ~$150k of salary. This $150k + startup equity was a better deal than the startup was offering in both salary and equity. Plus, equity bought as an investor is much less tax toxic than equity options received as an employee of a startup.

On the other hand, most people who work at startups aren't interested in money. If that's you, that's totally cool, and I respect that!