Well time keeps flying by and somehow these ridiculous numbers keep getting better and better each year. I am fully aware that one bad year which we are probably due for can and will greatly reduce these returns and I do feel like I am more lucky than I am skilled, but I now have 16 years of returns and have beat the SP500 10 of 16 years and my stocks have over double the annualized returns of the SP500 over the same period of time.

Doubling the annualized performance sounds cool and all, but if you stretch that over 16 years you see the absolute insane impact of doing that has over the long term. Over the last 16 years every dollar that I put into individual stocks has turned into $25.20 where as had I just only invested in an index fund would be worth $3.51 which is over 7x the amount of returns. The longer this continues and the bigger the numbers get the more exaggerated this will become.

Like I mentioned above I am not sure what to think of this. I feel like I have been EXTREMELY lucky and just a couple different decisions would have drastically changed the outcome of this experiment. I do think I have a certain knack for see what changes are coming in the world and having the conviction to stick to my intuitions even when everyone around me is calling me an idiot for talking about electric cars or streaming internet video. That being said I am well aware that none of the things that I was convinced about were necessarily a lock to become reality and Tesla could have gone bankrupt a couple of different times and Netflix could have been taken out by a competitor.

I am now to a point in my life where I need to make some decisions on whether to put it into cruise control and just ride the market averages or do I have a big enough cushion of excess money where I can continue to take calculated risks and if they blow up in my face I am still going to be perfectly ok. Ultimately I think the longer time goes I will probably fall into the latter camp of continuing to take calculated risks knowing that I can survive a few mistakes without meaningfully blowing up my future plans in life. I still have 40% of my nestegg invested in Tesla stock which is a very polarizing, speculative, and volatile company, but I strongly believe in the mission and the leader so this is one of those calculated risks. I don’t see it happening, but even if Tesla were to go to $0 I would still be in a very good situation.

This ability to have this huge cushion of money that is a big safety net is allowing me to take on some additional risks. I finally toyed with crypto this year and put $500 in to learn and fully expected to lose all $500. That $500 has now turned into a few hundred thousand dollars and I actually now am doing some side work in the crypto space for one of the top people in the industry. I also yesterday decided to take the plunge into real estate and put an offer in on some land to build a self storage facility with another friend who is a real estate investor.

For someone who had no experience in crypto and no experience in real estate these types of moves would be terrifying and honestly something I probably would have never done if I didn’t have the huge safety net of a nestegg. It’s allowing me to just explore and learn new things and new areas that ultimately very well could each result in even more money, safety, and ultimately freedom to use the rest of my life to continually explore and do things that I will truly enjoy or are interested in.

I still have my day job for now that pays me extremely well and gives me my summer months off and provides me with 7 weeks of vacation, but as time goes on and these other numbers continue to grow and other opportunities continue to blossom it probably does not make any financial sense for me to keep my day job anymore which is kind of a crazy thing. Not so much that I do not need to work any longer to provide for my family, just that I am probably costing myself money by using my time and effort at my day job. I know this is always the toughest thing for every FIRE person to do come to the realization of, especially when my current job 99.999% of people would kill for. Working 9 months year with an additional 7 weeks of vacation, crazy 401k matching, bonus, relaxed work from home schedule, etc and at the end of the day a point is coming here likely soon where I will say no thanks and this is coming from a guy with 5 young children to care for and put through college.

It’s definitely a major mind shift that is so hard to do when you spent your entire life finding ways to earn and save money and get a great job with great benefits and constantly hoarding away money for the future and now that future is here and to be perfectly honest its a lot scarier than I thought it would be. Turning off the spigot of cash and perceived security of a stable day job might honestly might be one of the hardest things I will do even though I know deep down I will look back and think you idiot you should have done that much earlier!! I think this is where the side work and the real estate investments will maybe finally push me over the edge where I feel confident enough that I’m not in any way hampering my or my families future by turning off the spigot of money from the day job.

Anyway long post as I don’t get out here as often as I used to and the end of the year is where I reflect and contemplate my life more. It’s been an awesome journey so far and I am genuinely excited for the next phases of my life. This blog has been invaluable to me and I honestly learn so much myself just by going back and reading older posts. Everything has gone better than I could have ever dreamt and now I just need to finish up the final few chapters of this journey.

Crazy stupid investing results below