1. Work for a company that provides signal-giving infrastructure for a variety of companies across disparate industries. Twilio is actually a perfect example.
2. Find someone to work with that already has or is willing to build a plausible history of so-so trades.
3. Occasionally tip this person off that company Y in industry X is about to have a good quarter. Never trade the same company twice. Parallel construct a plausible rationale for the trade based on public market signals if you want to sleep well at night.
4. Don't communicate over easily subpoenaed channels, obviously. The SEC isn't the NSA, basic OPSEC is fine.
5. Profit?
That's why I'm so disappointed by the OP! It's so easy to dream up a situation where they used their access in an effectively untraceable way.
Notice I mention high leverage. There are 2 challenges (as I see it) to committing insider trading. The first is having information ahead of time that actually predicts how the market will move based on the information. It’s not enough to know a company will have a good quarter you need to know it will be better than expected.
Second you need to be able to make outsized returns on that information. You have to beat the market returns by themselves. This compounds with the other issue above. The less obviously market moving data you have the more leverage you need.
This narrows the search space pretty considerably for an analytics based approach. You look at insiders with lots of access or anyone making high leverage bets.
Finally, do a mental exercise on your step 2. What does that even look like? An insider randomly approaching hedge funds? A random encounter at a bar? A frat reunion where they share each other’s trading history like term papers?
However if I'm reading your point correctly, you're saying this is harder than it sounds. If you already have a "sophisticated" understanding of the market enough to make this work with low edge, why bother with a criminal conspiracy. And to make outsized returns, you need to use lots of leverage, in which case you're taking on more risk of exposure.
Cash? Bitcoin?
Will this other person keep their mouth shut when the SEC comes knocking because some very successful traders seems to be handling a lot of cash or crypto? Or will they flip on you to stay out of prison?
Read up on Matt Levine's many, many examples of people getting busted for insider trading.
Crypto is useless unless converted into cash which requires identifying yourself.
Said WSBer could just take your tips and keep all the money.
2. Buy deep OTM call options in… a similar company that’s in the same business as Twilio
3. Never get in any trouble
You absolutely can get charged for trading in a similar company.
It's like these people think they're the first ones to ever come up with the idea of trading on privileged information so there's no way they'll get caught.