I have trouble getting a clear picture of a company and its prospects

In 2015 I was somewhat aware that AMD was making a comeback but I figured I didn't really know anything about how processors were made. Since the time I was looking at it it's gone from a few dollars to over one hundred dollars.

In 2016 I was aware Nvidia's cards were used for crypto mining and machine learning in addition to being the best graphics cards. I figured I didn't know what advantage they had over AMD, Intel, ASICs, and cloud services for machine learning. The new version of anything in technology is usually cheaper and better, so why shouldn't another company come eat their lunch? I would deserve to lose money in something I didn't understand.

When Tesla made the first Model S I went into a newly opened Tesla showroom and asked the employee about any cons the car had. The stock was probably a thousand times cheaper than it is now.
I just figured I didn't know anything about cost to make a car vs the profit and that the auto industry was a terrible place to invest.

Apple during the time of the release of the iPhone and iPad. Surely it can't go much higher. The company is already hyped and just about the most valuable company in the world. How much bigger can the company get? Today it's at least a ten times return since the iPad came out.

On and on. Bitcoin was ten dollars when I first heard about it. It went to one hundred and I figured that was the top of the pump. Bitcoin was promoted so much by the criminal financial press I figured it was just another one of their schemes. I didn't look at the inner workings. I had already seen them pump and dump Dot Com stocks and the housing market derivatives.

Now, I would have kept my money parked in all of these companies if I had more than I knew what to do with. In the past five years I've been nearly broke twice. If I had more conviction about the stocks I would have fought harder to stay in them.
I guess I'm asking how I can get a closer look at a security and get a firmer 'yes' or 'no'. These are the companies I felt strongest about and I don't get bullish about stocks like Groupon.
I don't do a deep dive on companies because I'm not really sure how. I kind of fear if I did look deeply at a company I would just bias myself in favor of it. Also, I'm skittish about putting money in a company I don't fully understand.
And, we used to have Bear Markets that would last four years. In the early and mid 2010s it felt like we were due for a long bear market to start. It's all been going up and up for so long you think you don't want to put money in and watch it slowly go down. I know five years and ten years are when you get 10x or 100x returns, but I don't have time for this. I'm aware of the stock every day and six months or two years of the stock doing nothing is like an eternity. I know short term stock prices are bullshit, but seeing a stock go up, and than back to where it was after a year or two feels like a failure of an investment.


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