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ArticleStock Trading

Investment tips from the president of a public company

One of the perks of working as a product manager is that every once in a while, you get invited to grab dinner with very senior people who have decades of financial and business experiences. I love hearing and learning about successful people’s approach to life and business. In this video, I will share with you an interesting story about one of those times and three key takeaways that you can learn from my conversation.


Some time ago, the management team that I worked with was invited to go grab dinner with the president of a public company. Coincidentally, I ended up sitting next to the guy and I figured why not… How often does this happen, let’s see where this goes, right?


We started talking about general work fluff, current events, crappy bay area commutes, vacation plans… I thought the conversation was going well so I started pivoting the discussion to some substantive topics: wealth building and wealth spending.


I said to him, “You know, as a guy running a famous company, you’ve clearly accomplished a lot. I’d love to hear about how you spend your time and money at this level of success.” 


He responded tersely with the equivalence of “what money?!”


I could have either interpreted him trying to be funny or him trying to shut down this direction of my conversation. I made a judgment call and played it off… “oh you know like how you spend your day when you have so much on the line, how to invest your hard-earned money”


Investing with resources

He ignored my first comment but actually opened up and started to share with me a really interesting investment approach. He said that as part of his normal day-to-day, he works very closely with the competitive analysis team (for potential acquisitions, competitive insights, industry trends, and etc…) Through this process, he gets a pretty good idea about what individual companies he might be interested in investing in.


I won’t bore you with the deals and I realize that we normal people don’t have access to that kind of analytics firepower but what we can glean from this successful individual are 2 important takeaways:


Takeaway #1: Make big bets

  • Spread your wealth if you want to be safe and sound, but you’ll never have the opportunity to build wealth faster if you don’t consolidate and make big bets


Takeaway #2: Don’t invest in hunches/fads/gossips

  • If you plan on investing in individual stocks, either qualify it from your own quantifiable research or from people you trust. You should never build your portfolio only hunches because that’s not investing, that’s gambling. And obviously, the more money you invest the more important this principle becomes. 


To riff off of his thoughts, I shared with him how my most recent investment, GoPro, gave me a quick 30% return because I bet that the market is not capitalizing on the fact that they are not just a niche hardware company but they are actually a leading video processing company too. Furthermore, they’re trying to move into the data storage subscription model which I’ve seen success from many other companies and that’s why I invested.



He seemed genuinely interested and asked a very astute question that I wasn’t prepared for. How do you know when to sell? And this leads to…


Takeaway #3: Always know when to exit

If a company doesn’t continue to generate value or hype, eventually the stock price will either stagnate or fall. So if you buy into a stock, you should know how much money you estimate you can get out of it and this will help you choose one investment over another. It will also help you validate whether you want to risk your money and the opportunity cost on THIS particular stock. 


Long story short, rather than making up a BS I told him I didn’t know and got a really awkward look from him. But because I didn’t know, I did a ton of research on how I can guesstimate the exit and ended up selling before the stock tanked by almost 50%.



All in all, I always make sure to retrospect and derive at least one positive learning from any conversation, especially if I felt like the conversation could have gone better. I hope you found these tips helpful. Follow us if you want to get more tips and tricks about building personal wealth like this.


I’ll see you when I see you.


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