Good opportunities to shift to buy and hold

When I first started investing, I would often lament the fact that I had missed out on earlier opportunities to invest in quality companies.
Mainly, Microsoft, because there were so many stories of people making a lot of money off their long term investment.
As I would dig into the numbers further, I figured out that even if I had of invested 10 or 15 years after the company became public, I would have still make a substantial amount of money.  With the dust settling on a new election and me turning 50 this year, it had me reflecting and asking the question, “Is now a good time to pick up the stalwarts of the future?”

I’m the youngest of 8 children, and I have a niece who recently will turn 36 and she will be having a baby soon. It had me running the numbers on the matrix of when my siblings turned 50, when she will turn 50 (2030) and I will be 64 when she does.  Below is my email to her, regarding some brief advice to “buy and hold”. What do you think are good long term picks?

Hi Dia,
Addressing your question in chat the other day of “What if…” and it’s something I’ve always struggled with, as I think we all do.
I have a little bit of a unique perspective being the youngest of 8 kids. I’ve seen the rise and fall of many family and friends.

In 1987, based on this chart,  Microsoft was roughly .25 cents per share (after factoring in all the splits, etc. over time, i.e. that’s what your cost would have averaged out to be if you never sold it) It was, in reality, I’m guessing roughly, between $50 and $80 per share.

In 1990, it was about (based on this chart, about .64 cents per share. Just 3 short years later, and you could have more than DOUBLED, your little quarter investment.
Even if you were late to the game, and didn’t invest until 1996 (The year we moved to NYC) your cost would still have still only averaged out to have been $6.
A $2,500 investment in 1987 would be worth about 590,000 today. The same amount invested in 1996 would be worth about $25,000 today. (still not bad)
My point is this, what I’m doing in the stock market in day trading is not efficient, and actually quite risky.  I’m slowly shifting to a more “buy and hold” strategy. It’s always hard to do that, because as we go through life, we need 10K for this and 20K for that, etc., etc.
You strike me as a person who has learned some fiscal responsibility as you have grown however, I wouldn’t categorize you as exactly “thrifty”.  lol 🙂
But I’m urging you to evaluate your finances. Bite the bullet.Beg, borrow or steal. (well…none of those actually)  and take 10K and put it into, say
Google.  or Amazon… and just forget about it.
I’ve attached a little age chart for you, that indicates my current age, and the year when you will turn 50, and the year that each of my siblings turned that age. When you look at it, it seems like they turned 50 only yesterday.
Did you know that my Father would have turned 100 this year!?
That’s one of the reasons for this exercise, and why it is so fresh in my mind.
I’ve seen everyone on this list, rise and fall, and rise again. (for the most part)
Can you imagine what the world will be like when your baby is 50!?   WOW!
I love you very much, and wanted to share this with you.
Take care.  Chat soon.  Keep us posted on the baby.
Love.
Uncle Jim

i_will_be_64
msft