How did you originally pick your longest held and/or best positions? What did you learn from those picks?

Per the title. I'm curious about how you originally decided to invest in what are now your longest/best holdings. What made you take notice of those companies in the first place? What have you learned from whatever methodology you used to make those top picks?

I think it's useful to honestly look back at the original thesis/logic if we want to replicate success. It's easy to get sidetracked with strategy, but in the end, the proof is in the pudding, so to speak…so what went into your pudding?

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For me:

The longer I continue my journey with stocks (~15 years now), the more I favor getting back to the basic axiom of investing in what you know. Of course this is a well known strategy (Peter Lynch, etc.), but I've been thinking more about it lately in the context of my own portfolio and how it has evolved over time. Most of the stocks that turned out best for me follow this rule, though I wasn't explicitly following the Lynch playbook at the time (because I didn't know who he was at the time).

My top 5 most successful (and also longest…not a coincidence) holdings are:

• AAPL – 10 years – bought my first iPhone and was absolutely blown away by it, coming from an Android device. iPhone seemed almost absurdly better than its nearest competition at that time, which seemed like a pretty good investment thesis. Bought the stock.
• COST – 8 years – bought after visiting a Costco with my parents in law and then immediately joining myself. Bought the stock as soon as I experienced it. I still love Costco, the company and the stock.
• CRM – 5 years – bought after selecting Salesforce as our main operations hub at my former employer. Become familiar with Salesforce admin, saw its power and flexibility, saw it in action, saw how it moved the dial. Bought the stock.
• UPS – 5 years – Was working a lot with FedEx. Their service was slipping and prices were going up. Missed deliveries. Not easy to deal with. Started using UPS…better service, better store experience, better prices, more reliable deliveries. Bought the stock. And of course they started eating FedEx's lunch.
• AVGO – 4 years – This is the outlier. I bought based on a generally favorable outlook for semis, and they seemed highly financially secure, are broadly exposed to the semiconductor industry (sort of a picks and shovels play; AMAT is my other), and pay a large and growing dividend. Worked out well despite my lack of direct personal knowledge.

Conclusion: I didn't read Lynch until relatively recently, and I wish I'd discovered him earlier, because the foundation of my portfolio is composed of my “Lynch stocks”, and in hindsight, I could have avoided a lot of painful lessons and headhaches if I'd just started out picking from a basket of companies I know, like, admire and trust.

I'm increasingly thinking that “invest in what you know” is less about finding the best companies – though that's part of it – and more about finding the deep conviction to hang tight over many years, which is where a lot of the outperformance is generated.

I also note that none of these picks were particularly cheap when I bought them. The best companies are rarely cheap.

Thoughts? Experiences?