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Ask HN: How do you invest?

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Re: Ask HN: How do you invest?

#6
I personally own (not through a broker) shares in a diversified portfolio of companies, all of which offer Dividend Reinvestment Plans with optional cash purchases of additional shares directly through the company's transfer agent. This means that I pay no fees when purchasing additional shares for my DRiPs, in fact, a lot of the companies I invest in offer discounts on shares purchased through their Share Purchase Plan. I mostly invest in large companies that pay reasonable dividends with long histories of stability and dividend payments/increases. My goal is to almost never stop buying, making use of dollar cost averaging, and earn a safe return that ought to still beat the market in order to save for retirement/other future investments.

Re: Ask HN: How do you invest?

#7
post #6

I personally own (not through a broker) shares in a diversified portfolio of companies, all of which offer Dividend Reinvestment Plans with optional cash purchases of additional shares directly through the company's transfer agent. This means that I pay no fees when purchasing additional shares for my DRiPs, in fact, a lot of the companies I invest in offer discounts on shares purchased through their Share Purchase P…

Buying DRIP stock has a lot of tax complexity. You establish a new cost basis for stock with every dividend you receive. I.e. 4x a year.

   Above all, the importance of recordkeeping cannot be
   overstated. Unlike other tax-related documents, DRIP
   statements, recording all reinvestments and OCPs,
   should be kept indefinitely. [1]
But if you die and leave everything to your heirs, all is forgiven. They get a brand new tax basis and it no longer matters when you bought.

[1] https://finance.yahoo.com/education/drip/dspp_plans/article/...

Re: Ask HN: How do you invest?

#9
Betterment and Bitcoin speculation for the most part. With the right knowledge, you can certainly outperform Betterment, but as a programmer I'm content just outsourcing that and saving that time for other things (like getting better at programming, for example, which implicitly earns me money as well).

Re: Ask HN: How do you invest?

#10
post #6

I personally own (not through a broker) shares in a diversified portfolio of companies, all of which offer Dividend Reinvestment Plans with optional cash purchases of additional shares directly through the company's transfer agent. This means that I pay no fees when purchasing additional shares for my DRiPs, in fact, a lot of the companies I invest in offer discounts on shares purchased through their Share Purchase P…

Buying DRIP stock has a lot of tax complexity. You establish a new cost basis for stock with every dividend you receive. I.e. 4x a year. Above all, the importance of recordkeeping cannot be overstated. Unlike other tax-related documents, DRIP statements, recording all reinvestments and OCPs, should be kept indefinitely. [1] But if you die and leave everything to your heirs, all is forgiven. They get a brand new tax b…

Thanks for the advice. It is important not to overlook the downsides of any investment strategy, and I do keep very diligent records.

The downside to DRiPs as you mentioned is the amount of paperwork you have to do and the difficulty in selling. For me, however, I am willing to incur that cost for the upsides which are particularly maximized by my personal situation.

I am not sure about how difficult US taxes are, but in Canada they are fairly straightforward for someone adept at math and logic.

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