On my road to FIRE, I’ve had to make a handful of big decisions that have had a material impact on my net worth. As I reflect, there are a set of decisions that were pure luck and others that were calculated. Regardless of intentional or not, they have significantly contributed to or enabled my net worth to be where it is today. As I list out the big money decisions, I’ll try my best to be specific about the numbers. Are you ready? Standby.

Money Decision #1 - Going to an in-state university to study Computer Science

Despite most of my close friends going to academically prestigious schools like Stanford, MIT, and Duke I ended up at the University of Kentucky. It was a tough pill to swallow at the time because, like all other 17-year-olds, I wanted to go out of state, badly. However, looking back, this was one of the best decisions I’ve made. Instead of coming out of school in 4 years with ~$100K in debt, I graduated in 2.5 years (i.e. 5 semesters) with ~$30K in the bank. The 1.5 years and $130K difference gave me a longer runway to find my footing in this very dynamic world.

Finally, it turns out that I hit the lottery in the profession that I chose. In 2005, Computer Science graduates in Kentucky were only making $45K a year. These days the top tech companies are paying $200K+ to new college grads. What I thought was a passion profession, turned out to be the most lucrative profession for the level of education!

Money Decision #2 -- Moving to the Bay Area

In 2011 I moved to the Bay Area to work for a startup. I was chasing the dream to change the world in a dramatic way. Even though my impact has fallen short of my expectations, it turns out that the Bay Area is the best place to make the most money for anyone in tech. Once I saw that the compensation trends in the Bay Area for tech were rising at an astronomical rate (e.g. $140k total compensation new grad in 2011 vs $200k in 2014) and that the ceiling for engineering leadership roles was well into the multi-million dollar range I knew I hit my second jackpot.

By physically positioning myself to be in the mecca of tech, I estimate that it’s allowed me to earn at least 4x what I would have earned had I stayed in Austin, TX for my first job. 

NOTE: These days, NYC, Seattle, and LA pay are rivaling that of the Bay Area.

Money Decision #3 -- switching companies often

One of the advantages of switching companies often is that you get to build on top of your current financial position. For example, if you’re at Microsoft making $300k, competing companies such as Google, Facebook, Netflix will pay at least $300k assuming that you pass the interview at the proper level. So for most people, switching companies is actually the best short-term move they can make to increase their compensation. However, I wouldn’t advise this for people who have deep ties with leadership and are on a high growth trajectory.

Aside from always being at the highest end for my level by crushing interviews and negotiating hard, I’ve collected over $300k in sign-on bonuses. This is often overlooked because it’s money that you get the minute you join and can be immediately re-invested to capture the stock market boom we’ve been experiencing. 

Money Decision #4 -- Not selling Facebook, Google, or Microsoft stock

Over the years, I’ve worked at companies like Facebook, Google, and Microsoft (LinkedIn). As a part of being employed, I receive RSUs. These RSUs make up the majority of my compensation. Normally, I would advise myself and everyone else to sell their RSUs and buy what is good value at the time. However, I was dumb and got lucky. I never sold any shares until they started to become more than 20% of my net worth. As of the writing of this blog, the stock appreciation has been 900% for Facebook, 379% for Microsoft, and 90% for Google.

Facebook and Microsoft now make up a significant portion of my net worth. 

Money Decision #5 -- Investing heavily in tech stocks

If you have been following this blog, you know that I’m a big fan of dollar-cost averaging into index funds and dividend aristocrats. But there are situations where I see a market opportunity. In those scenarios, I generally invest in $20k+ lots. Here is a list of companies that I’ve invested in and their prices, sorted by how much I own:

• AMZN - $278 (now $3,094)

• AAPL - $32 (now $122)

• TGT - $54 (now $198)

• LYFT - $22 (now $63)

• UBER - $15 (now $54)

• TSLA - don’t laugh

• TQQQ - $34 (now $96)

• PLTR - $14 (now $23)

• SHOP - $560 (now $1,106)

• ZM - $140 (now $321)

Money Decision #6 -- Dollar-cost averaging into index funds

I’ve continued to keep my expenses low, relative to how much I make. Any pay increase is an increase in my weekly dollar-cost average, not an increase in lifestyle. There have been many dips in the last several years, but my DCA routine has never been discontinued. As a result, I’ve been able to capture the full bull market. The majority of my gains is not from my bet on AMZN or UBER, it has actually been from just being patient, detailed, and in general, disciplined.

It is really hard not think about splurging when many of my friends and peers at work are driving brand new Teslas, living in $2M+ homes, and going on fancy international trips.

Money Decision #7 -- Worked for Google, Facebook, and LinkedIn in my prime earning years

In addition to continuously investing, it’s important to invest a lot! By working for the best paying companies with the most generous refreshers I’ve been able to significantly amp up how much I dollar-cost average into the stock market. When I started on my road to FIRE, my goal was to invest $100,000 per year into the stock market. However, as I progressed I’ve been able to get that number to be north of $30,000/mo, including 401K contributions, DCA, M1 Finance portfolio for this blog, and individual stock investing. By earning high-end FANG compensation, I can meaningfully invest in all of those areas without losing sleep.