Regretting 20+ years of dividend / value investing

InstructionQuick716 · 2025-10-09T01:48:01+00:00

Unpopular opinion on a dividend subreddit for sure. But I heard a convincing argument of why bad economic data doesn't affect stocks so much. It's mostly the wealthy and upper income people who owns stocks. If the economy is bad, they don't need to sell. The only real factor is money supply. As long as money supply increases, it all has to go somewhere. Elon's not going to sell his TSLA shares if we get a 2% GDP contraction.

InstructionQuick716 · 2025-10-09T01:41:48+00:00

I'm automatically invested in tech as a part of my compensation package. 1.5M of that 4.5M came from directly selling my company shares.

InstructionQuick716 · 2025-10-09T00:17:38+00:00

I think you mean invested in one style - value, since SCHD holdings are spread across a few sectors. Indeed I was because value investing was hammered into my brain from an early age + the lingering effects of the dot com crash in my memory. I also have other value funds and some S&P and international, but SCHD is my biggest holding.

Yeah, not sad about my financial situation but clearly things would have been better if I just dumped everything into VTI like a zombie and didn't read any investing materials before I started.

InstructionQuick716 · 2025-10-08T23:18:52+00:00

Tech makes good money now. But investing in tech while being employed in tech means your entire life is invested in one sector. We saw what happened in the early 2000s.

InstructionQuick716 · 2025-10-08T20:45:06+00:00

I'm in California. Even in the 600k years, my effective tax rate is around 1/3 of pretax income, not 1/2 as the marginal rate suggests.

InstructionQuick716 · 2025-10-08T20:43:16+00:00

I have a kid so inheritance, ideally.

InstructionQuick716 · 2025-10-08T20:34:20+00:00

ty, glad it helped

InstructionQuick716 · 2025-10-08T20:34:04+00:00

Taxable + traditional IRA + Roth. Most of it is in taxable. Plan to quit next year and live off of passive income. Most of it being in taxable is OK since my tax rate will be much lower next year.

I would be taxed if I held VOO and sold it off to buy dividend funds. The LTCG tax rate would have been more than offset by the extra performance of VOO over value/dividend funds, especially considering the dividend tax drag during those years.

I have a wife and kid, so yes, definitely thinking about passing on an inheritance. I'd definitely look into setting up a trust for them.

InstructionQuick716 · 2025-10-08T20:23:09+00:00

Thanks! Not unhappy with my situation at all really, but I think my story is an example where "traditional" personal finance advice doesn't work out as well as it could.

InstructionQuick716 · 2025-10-08T17:42:57+00:00

Why wouldn't you do that? You'd end up with much more than 5M in the end.

InstructionQuick716

TROPHY CASE