u/sponge_boy_mee_bob

I’ve been watching Reddit for a while with a plan to invest in it last week, but I was just getting out of a different large trade which executed at the end of market Friday - this was going to be my source of funds to buy Reddit, but the funds had to wait until Monday to settle. Reddit stock gapped up on Monday so I figured I’d wait for a pullback, but I’ve just continued to watch it rip higher on the sidelines. Now I don’t know what to do. I believe in the stock, but I don’t want to FOMO into this insane rally and then immediately miss the chance at a lower cost basis on a pullback. Then again, what if it keeps ripping much higher and I continue to miss out.

Thoughts from experienced Reddit traders? Do you think I’ll get a chance to buy back in the high 130s or low 140s before earnings this month? I’d sell cash secured puts for a premium which could help my cost basis a little if filled.

I’ve been selling CC and CSP for about a year and a half now, and have had good success. I started in fall of 2024, so 2025 was my first full year. The trading income is becoming a significant contributor to our global household income. We have to pay in a decent amount to the tax man this year, and my tax bill is going to be even larger come next April.

I have a full time job which pays well. My wife also works, for now. We are thinking about having her stop working to have her get real estate professional status so we can do a cost segregation on a real estate investment this year to reduce our tax bill next year.

Anything else that we should be doing to help offset the income from wheeling to minimize tax owed for next year and beyond? While I’ve had good success so far, I’m sure that I still have plenty to learn, so any advice is appreciated. Thanks!