My Financial Journey

Well 20 years in the books and I could not have ever dreamed things would have turned out this well. After 20 years of investing I’ve achieved every single one of my financial goals well ahead of schedule. A lot of this has been due to the outperformance of my portfolio. 2025 was not a good year for me losing to the SP500 for only the 2nd time in the last 9 years and lowering my all time performance. That being said my all-time individual stock portfolio has returned 19.37% annualized returns vs the SP 500’s 9.87%.

Outperforming by 9.5% doesn’t seem like much but when compounded over 20 years its absolutely insane. A single $10,000 investment when I started this blog 20 years ago would have grown into $65,702. Meanwhile $10,000 invested in my stock portfolio would have grown into $345,067! If this experiment was carried out another 20 years that $10k in the SP500 would be worth $431,683 and $10k in my stocks would be worth $11.9 Million dollars!!!!!!

I have no allusion that this performance will continue forever though to be perfectly honest I think I will be able to keep it going for a few more years.

As is now annual tradition I will list my investment holdings as of the year end. As usual I did not do much of any trading. In all of 2025 I made exactly two trades. I used my early retirement cushion to buy a large chunk of Tesla in March when everyone was worked up about Elon & Trump & tariffs and this buy is now already up 80%. Also just this last month I decided to finally take a stake in Google and trimmed some Chipotle and Netflix to do so.

Tesla still dominates my portfolio and was the one investment I invested a significant amount of money in this year, but I felt like the opportunity was too good to pass up and I feel very confident that this company will continue to grow and change the world with its products in the years to come. It’s an obvious one to trim as it accounts for nearly half of my net worth and that day will come. I did try it last December as I was going to quit my job full-time and sold 10% of it, but then I put it all back in this March.

SP500 index funds take up a quarter of my portfolio and is still where basically 100% of my retirement contributions are going and this has been the case for my entire investing career. I’ve just been very lucky with my individual stock investments and they account for 75% of my portfolio despite receiving a small portion of the contributions.

I also need to start shifting my focus from contributions and growing investments to doing withdrawals and preserving my wealth as I move onto my next phase of life. This will likely require some reshuffling of my portfolio and some reworking of my spreadsheets which is already under way as we actually have withdrawn for the first time in our lives from our investment accounts the last two years. This felt like I was doing something horribly wrong, but in reality this is the whole point of this entire exercise is to use this money to maximize the enjoyment in our lives. This comes from purchasing things but also from having the freedom to do what we want with our time which is where the real value lies.

It’s so strange that the skills that were needed to get us where we are today are not the skills that will serve us best going forward and to be perfectly honest this is a very tough mindset shift.

Anyway back to my portfolio. A lot of Tesla but probably not trimming right now, 1/4 index funds, and another 1/4 individual stocks, private stock investments, and real estate investments. My real estate foray will actually come to an end tomorrow as we will sell our commercial property. I’ve always had this greatly understated on these reports, but I finally bumped it up to around the closing value. So essentially after taxes tomorrow our cash position will grow to about 9%. Ideally I would like this to be about 12% as that would be about 3-5 years of very comfortable living expenses.

Regarding real estate this will turn out to be a good investment. I will make over 200% return over 3.5 years of owning it. It was a fun investment and its neat to drive by a building and know that you own it and you are giving other businesses a place to set up shop and its fun to see them excel too. It also let me use my brain a lot to solve problems, negotiate with tenants, negotiate with the HOA, and overall those were challenging and rewarding. That being said it was also work and at times stressful. I also went into this investment with other investors and I did kind of like the team aspect of it with everyone bringing some skills and experience to the table.

That being said with other investors comes different perspectives, philosophies, investment goals, and risk tolerances. I am long term buy and hold guy and some of my partners were more short term focused. Some of my partners also had a completely different outlook on leverage/debt and how it should be used. Ultimately we butted heads quite a bit on this and ultimately it ended up with us selling the property at a pretty significant discount to its actual value. We actually had contract that fell through earlier in the year that would have resulted in double the profit we are getting tomorrow, but once that fell through everyone was hungry for money now and that led us down this road.

The beauty of stocks is I can push a button anytime Monday through Friday and I can get my funds in seconds. If I need a million dollars in 30 seconds I can get it. Real estate moves so much slower and there is so much that can go wrong before a deal closes. Also selling and buying the property is so expensive and time consuming. You also have so many parties involved any of them can derail things or make it very difficult.

I did not really like having to answer to a banker every year to prove that I was still worth of the loan (even if I could have easily covered the entire loan myself without my parters and not skipped a beat). I also did not like having to guarantee the loan with my partners and being exposed to their potential dominoes of dozens of properties leveraged to the max with bank loans and personal guarantees that could come back and affect this property. Some of them needed a constant flow of refinance money to keep things going and ultimately that was why I was fine selling this property at below market value even though it was cash flowing more each year than we had all put into it.

I did consider buying them all out at one point in time, but then I realized that Elon Musk does not call me in the middle of the night to tell me he’s got some major problem (furnace not working, water leak, etc) and that stocks have treated me well. For now I will stick with stocks and if I do decide I want to get into real estate again and buy myself a side job I will probably go solo and probably just pay cash, but without the leverage real estate returns are pretty abysmal compared to stocks.

So long term I will probably stick with what works for me and any real estate would just be to help my kids if they decided they wanted to do this. I do think its a decent investment if you are ambitious, know what you are doing, and are at a point in your life where you need to grow your asset base and can take on the risk and also do not over leverage yourself where you can get wiped out.

Anyway long story short. No more real estate for me. Still letting my winners run as far as individual stocks and will look at ways to diversify my individual stocks over time by raising cash and moving more money to index funds, but for right now I’m in a spot where I can let a few of these companies continue to do what they do.

Investment	Percentage
TSLA	44.61%
VIIIX	24.27%
SHOP	5.31%
NFLX	4.10%
SGOV	3.98%
400 North	3.96%
AMZN	2.79%
WOLFRIVER	2.23%
NET	1.86%
GOOGL	1.61%
AAPL	1.52%
$$CASH	1.24%
DDOG	1.16%
ETHUSD	0.85%
CMG	0.34%
VFIAX	0.17%
BTCUSD	0.02%

Time sure flies and I now have 19 full years of investing under my belt. Things have turned out better than I could have ever imagined and I’ve blown through every single goal I set for myself. I did the hard part of starting early, living well below my means, and consistently investing without freaking out and doing something stupid. The vast majority of my money went into SP 500 index funds and I experimented with a small portfolio of individual stocks with some of our IRA contributions.

That small amount of individual stocks has grown to something almost unfathomable as I’ve now averaged over 19% annualized returns over 19 years. Meaning that $10k over that period of time has grown 30x in value to $300k. I always viewed this as more of a fun experiment and never put in a significant amount of money and never jeopardized our normal index fund plans. If this portfolio went to $0 I was still going to be ok.

Luckily for me I’ve now owned some of the best companies in the market in some cases for almost two decades and have gotten outsized returns. I’ve owned Netflix since 2005 ($3.75), Starbucks ($12.41) since 2007, Chipotle ($0.85) since 2008, Amazon ($5.87) since 2010, Apple ($11.45) since 2011, Tesla ($2.50) since 2013, and Shopify ($3.20) since 2016. Buying great companies, led by amazing founders, and held for decades has turned out to be a good recipe for success. That being said I still feel luck played a large role in this and this is why probably 90% of my contributions have been into index funds.

In annual tradition I will list my best and worst individual stock performers for 2024.

Best Perfomers
Netflix +90.25%
Tesla +62.56%
Amazon +46.33%
Shopify +44.02%
Cloudflare +35.70%
Apple +34.90%
Chipotle +34.30%

My worst performing stock
DataDog +24.17%

Well what a weird year when the worst stock in my portfolio actually returned 24% and every single stock in my portfolio bested the SP500 for the year.

In annual tradition I list all of my investment holdings. This is a fairly static list as I only make a few trades per year and in some years have actually not made a single trade. That being said I did make a handful of trades earlier this year where I got rid of a few stocks (Starbucks, Brookfield Infrastructure Partners,Monday.com, and Crowdstrike) and all of that money plus some additional money went into Tesla.

Clearly I have had strong conviction about Tesla and it has rewarded me handsomely. That being said there is risk that it accounts for over 41% of my retirement nestegg. I am ok with this, but this is something that I plan to possibly mitigate as I completely stop working as the risk/reward profile probably doesn’t make sense as it will always be a volatile stock. I also already sold over 9% of my Tesla holdings in late December to fund a few years of my early retirement fund so as of right now I have 4 years of early retirement funds where I don’t need to worry about fluctuations in my portfolio as much.

Another item I added as 400 North which is a Commercial Real Estate property I bought 2 years ago to learn a little bit about real estate. I never included it before as I’ve never included real estate I own in any of my networth calculations as I don’t view real estate as something that is easy to sell or would be sold in many cases.

That being said after owning the property for 2 years me and my partners actually have it under contract to sell in a few months so I’ve included my initial investment amount in my retirement nestegg as it seems like we will make money on this property. It’s actually selling for an amount where I will make nearly 5x my initial investment, but for now to be safe I will leave it as if it’s only worth my initial investment as the deal could fall apart and I’m not sure I plan to use this money for my retirement nestegg. I will actually walk away with almost 9% of my nestegg in cash at closing before taxes, but I might roll that over via 1031 into another property so we’ll see how I decide to value it or not.

The smart thing would be to take that money and pay taxes on it and fund another 3 years of retirement, but I might continue to try to learn about real estate and purchase a property on my own that could be used for other ways in retirement.

Really at this point going forward I will probably no longer do much buying and slowly trim down the portfolio to keep my cash savings at 3-5 years of cash and trim down for various purchases. In fact this year alone we withdrew and SPENT 8% of our nestegg with some longer term projects (solar panels, vacation land, backyard patio, vehicles). This is almost shocking to type and is the hardest part about early retirement is that I’ve spent my entire working career saving money, buying investments, and living very frugally and now I’m to the point in my life where I need to start figuring out how to spend the money to bring me and my family the most enjoyment and it goes against every gut feeling I’ve acquired over the years that got me to where I am today. Selling great investments to spend the money has required some mental gymnastics on my part. I’ve always treated our investment accounts as one way roads where the money goes in and grows and almost feel like I’m breaking the law now that I’ve tapped into them for the first time in my life.

Well a bit of a bounce back this year after last years pullback that halved our nestegg. We greatly exceeded the performance on the SP500 this year which is the 11th time in 17 years and the 6th time in the last 7 years we’ve accomplished that. Overall any individual years performance is nothing to get too excited about, but we now have a 17 year track record to look back on. Long term performance is greatly skewed by recent performance, but we have now exceeded the total return of the SP500 by 375% over 17 years and this is entirely driven by the outperformance of our individual stock portfolio that has now exceeded the SP500 by over 1400%!!

We still however are not at all-time highs as our nestegg lost 45% of its value last year and while 50% plus returns are amazing – we needed closer to 100% returns to get back to what we gave back last year. This is why looking at anything in a short time window of a few years really isn’t really going to tell you much.

Also despite our insane outperformance by picking individual stocks we continue to contribute 100% of our money to index funds and high yield stable securities and have done so now for close to 10 years. I feel like we have gotten very lucky with our individual stock investments and I’m not convinced I’m the second coming of Warren Buffett so we continue to follow the original plan of having the vast majority of our investments be in index funds which is what I would recommend to anyone.

We do however currently have 60% of our money in individual stocks and this simply due to the fact that our stock portfolio has now averaged 17.75% annualized returns over 17 years which has turned a relatively small amount of investment into an insane amount of value. We will continue to let these investments do the bulk of the heavy lifting and over time I do see more and more of this money being converted over to index funds, but for now I still feel very confident about our long term investments and will let them run for the foreseeable future.

I also realize at this point the only meaningful thing I can do to our portfolio is to screw it up by thinking I’m smart and taking risks that if they pan out wouldn’t meaningfully change our lives anyway. With this being said if all of our individual stocks went to $0 we would still be doing pretty ok. Also almost all of our individual stocks are actually now pretty big household name companies with many sources of revenue and global reach so I feel like as time goes on our individual stocks are becoming more and more stable (if you totally ignore last years 68% drop for our stock portfolio 😛 )

In annual tradition I will list my best and worst individual stock performers for 2023.

My Best Performers
Bitcoin +154.96%
Crowdstrike +147.21%
Tesla +129.86%
Shopify +118.33%
Cloudflare +93.54%
Ethereum +92.82%
Amazon +77.04%
DataDog +68.37%
Chipotle +66.79%
Netflix +65.07%
Monday +57.26%
Apple +53.94%

Obviously a very good year overall for the entire market and a great year for some of my larger positions. I do have a few newish positions (only 3 years old) that had some strong performance with the cloud stocks (crowdstrike,datadog,cloudflare, monday) and the crypto that were high fliers this year, but what is even more telling for me is the massive performance by stocks I have literally held for over a decade in Tesla, Shopify, Amazon, Chipotle, Netflix, and Apple all coming in with 50% to 130% returns. Many of these are huge companies who have been growing rapidly forever and have made me loads of money already and here they are still in some cases almost 20 years after I bought them still propelling me rapidly to new nearly new highs.

This year will be the 20th anniversary of my first Netflix purchase and I’ve owned most of this bunch since the 2000s decade and some of them have gone up more than 100x in value from my original purchase. The only thing I had to do was do nothing. This is harder than it sounds as clearly we have to be staying up to date and listening to pundits and doing all kind of hard research in order to pick the best stocks and clearly the smart thing is to take profits off the table when a stock has had a huge run and companies can’t grow forever and it’s best to take money from those companies and invest in the next batch of up and comers and yeah……doing nothing is the hard part or at least it is initially.

I feel confident in the companies I’ve invested in and the leaders who run them. Picking out the best companies in the world is honestly not all that difficult. Great leaders running companies who only focus on making great products. You know those products when you use them. The first time you touched an iPhone, drove a Tesla, signed up for Netflix, ordered your first Amazon package, you knew deep down this was something at a completely different level that was going to change the world. Buy those companies and hold onto them forever – it will change your life.

My Worst Performers
Starbucks -4.78%

Starbucks is the only company who lost me money this year. Ironically after my sermon above I have never had a Starbucks coffee and don’t drink coffee so hard to get a strong conviction on this one other than I’m probably the only weirdo who doesn’t drink coffee and frequent Starbucks. I’ve also owned Starbucks since 2007 and it’s been a great performer for me over that time span.