Investing Lessons From A Surreal 2017 (2024)

Investing Lessons From A Surreal 2017 (1)

Here are some investing lessons from a surreal 2017. It's always good to learn and review each year to hopefully improve risk-adjusted returns.

At the beginning of the year, I decided to track my investmentswith a detailed spreadsheet. My cash flow was increasing and I wanted to make sure the money was being properly deployed. If Iforce myselfto thinkfor hoursabout how toinvestmymoney,hopefullyI won't rashly spend it on completely wasteful things such as a sports car that can't fit a baby seat or a vacation property I'll hardlyeveruse.

On the flip side, ever since the housing crash I've had a heightened fear of losing money. This is especially true since I haven't had a job since 2012. It takes around three years as an entrepreneur to feel confident you won't starve on the streets. When you are a parent, the pressure is even more. As a result, I tended to hoard cash, which is suboptimal in a bull market.

This post will go over my investment thought process by category for 4Q2017. I'll also conclude with some investing lessons learned about the year. The goal of tracking our investments is to try and take full advantage of a bull market.

Investing Lessons From A Surreal 2017

In summary, I mobilized a total of $2,263,319 into various investments in 2017. This is why I say 2017 was so surreal. This was the most amount of money I've ever invested in on year.

$750,000 of the $2,263,319 was invested in conservative investments (bonds, mortgage pay down, and home improvement). They should return ~4% or more gross a year. The remaining $1,500,000+ was invested in riskier assets with a target return of between 8% – 18%. My goal is to achieve a 10% total annual return, but will gladly settle for 8%.

The $2,263,319 invested was largely helped by a rental home sale in June 2017, which gave me ~$1,788,000 in proceeds ($2,740,000 sale price). Due to declining rents, expensive valuations, potentially rising mortgage rates, higher property taxes, potentially negative tax policy changes, PITA tenants, better investment opportunities, and less time due to a newborn, I thought it best to sell one of three properties in CA.

Overall, I reduced my risk exposure by $476,681 and increased my cash position by $450,000. Despite the decrease in exposure and increased balance sheet, I stillhave synthetic full exposure to risk assets due to $1,092,000 of remaining mortgage debt from my primary residence and vacation property rental.

Investing Lessons From A Surreal 2017 (2)

Related: Reinvestment Ideas After A Home Sale

Real Estate Investing Lessons 2017

Because I wanted to see if I could find a winter property deal, I held onto a lot of cash. I found two homes that I liked, but the sellers wouldn't entertain my low ball offers. I wasn't even sure I'd be happy with the purchase even if they did accept my offer because of all the maintenance and tenant issues I'd have to deal with again. For example, one home had a serious leak in the garage that kind of gave me a little PTSD from all the leaks I experienced at my old rental house.

By Dec 1, I realized I was never going to buy another property in San Francisco again, so I decided to invest another $300,000 in real estate crowdfundingafter meeting up with the team again for dinner. Since the summer, the fund invested in a flex-industrial deal in Chicago MSA, a multi-family in Phoenix, a strip mall in Orlando MSA, and a multi-family in Canyon Lake, TX.

Although a total of $800,000 in real estate crowdfunding sounds like a lot, I view it as buying a $800,000 portfolio of 12+ different properties across the country at much lower valuations and much higher net rental yields compared to having $2,740,000 in one very expensive rental property in San Francisco that is now at risk of depreciating due to declining rents and new tax legislation that limits mortgage interest deduction and SALT deduction.

The next physical property I will buy will be a primary residence in Oahu.The plan is to move back to Oahu withinthe nextfive years before my sonstartskindergarten. I really like the idea of buying physical property to personally enjoy, and then renting it out years down the road if you have the funds and the desire to move. If the rental experience goes well, I'll keep the property. If not, I'll sell it and follow my BURL real estate investing strategy.

Stocks Investing Lessons: Bought The Dips

In October, I started getting excited about the potential passage of a tax plan that would lower taxes for large corporations and businesses like mine with pass-through income.

As a result, I invested more aggressively into stocks because I felt the market would respond favorably if the plan passed. Further, my desire to buy another property kept going down. Corporate earnings are estimated to get a 8% – 10% boost and small business with pass-through income might see an even larger gain.

The timing of this tax plan is fortuitous given I've spent 8.5 years building a lifestyle business that has now reached a level where it will benefit from tax changes. Nothing has made me more bullish than business tax reform, which is why I need to keep my emotions in check through this investment review process.

Finally, I superfunded my son's 529 plan with $70,000 while his mom and grandma contributed $14,000 each. We figured this would be a good method to diversify contributions since once you superfund, you can't contribute for four years. It's good 529 plan owners have the flexibility to use the proceeds for grade school education now.

See:How The New Tax Plan Will Ruin Your Life If You're Not Careful

Bonds Investing Lessons: A Positive Surprise

Bonds performed well in 2017 with the the long-bond index fund TLT up ~10%. My California muni bond positions are up ~3.5% + ~4.5% gross adjusted yield for a total gross gain of about 8%. Not bad given I was just looking for around a 4% gross gain with my safe money.

Investing Lessons From A Surreal 2017 (3)

Once the 10-year bond yield gets back to its 12-month high of 2.6%, I'll be looking to buy more bonds again. I see a 3% cap on the 10-year bond yield for 2018.

Related: The Case For Bonds: Living For Free And Other Great Benefits

Mortgage Pay Down

If you add on the $815,000 of mortgage debt I paid off by selling my rental house, I'll have paid off a total of $921,000 of mortgage debt in 2017. It feels fantastic to have almost a million dollars less in debt, even if the interest rate was low. By consistently paying off random chunks of extra principal throughout the year, it was easy to pay down an additional $106,646 in principal.

I've still got about $1,092,000 in mortgage debt to pay down between my vacation property and my primary residence. I certainly don't need so much cash, but I want to continue legging into risk assets just in case there's some type of downturn or a change in my lifestyle.

My plan is to pay off my vacation property mortgage by 2023. I probably won't pay off my primary residence within five years because I need as much cash as possible to buy our future dream residence in Hawaii.

Related: Pay Down Debt Or Invest? Follow The FS-DAIR Framework

Everything Else

I've committed $200,000 to my friend's second venture debt fund. They've called $96,219 within one year. I expect them to call the remaining $103,781 by the end of 2018. The fund's objective is to earn a 15% – 20% IRR. Based on the performance of his first fund, a more likely return of 10% – 13% should be expected.

It felt great not having to do any home improvement projects since 1Q because we now have a baby who requires precious sleep. Any disruptionofsleep wouldhave beeninfuriating for all of us since my wife and I werelikezombies for the first three months.

Finally, out of the $611,000 in stock investments, $50,000 of that was in highly speculative investments that have surprisingly done well.

Related: How To Make Speculative Investments Without Losing Your Shirt

Main Investing Lessons Learned In 2017

My biggest mistake was not being more aggressive investing in the stock market at the beginning of the year. I didn't have as much liquid cash because I hadn't sold my rental house yet, but it was the Trump presidency and high valuations that gave me hesitation. I wasn't too hopeful about tax reform either.

My best move was selling a rental house for 30X gross annual rent before the SALT deduction got limited to only $10,000 and redeploying the capital in properties around the country trading at just 10-14X gross annual rent. Life feels so much better not having to deal with housing issues anymore. It's also nice to worry less about natural disasters.

Here are several lessons from 2017 that may help you become a better investor.

1) Try to look beyond the politics and focus on fundamentals.

Given I live in San Francisco, I know plenty of people who decided to pull much of their money out of the stock market at the end of 2016. They were so blinded by their hatred of Donald Trump that they missed out on huge gains. Focus on economic and earnings fundamentals. Generally speaking, deregulation and lower taxes are good for business, which is good for business investors. Further,in my mind interest rates wouldremain accommodative for longer.

Unless our politicians actually reform laws, there isoftena disconnectbetweenhow much investors believe our politicians can do and how much they can actually. Reduce risk if you wish. But don't get out of risk assets completely.

Investing Lessons From A Surreal 2017 (4)

2) Real estate is an easier investment over stocks.

How can this be when stocks just went up ~20%? Having to reinvest my home sale proceeds was exhausting. If I didn't have weekly reminders to invest, I wouldn't have because of the uncertainty of what to invest in, the timing of the investment, and the actual act of deploying capital. Every investment I make gives me a little bit of anxiety due to my fear of losing money and looking like a buffoon.

With real estate, despite the leverage, all you're doing is enjoying your home or collecting rent checks (if you're lucky).When you're just living, you aren't questioning every single investment you make. Therefore, for most people who are too busy to track the market,owning real estate over the long run is an easier path to wealth.Despite my terrible tenants, the $1 million of equity gain from 2012 – 2017 was the easiest investment money I've ever made.

If you don't have enough money to buy real estate, then owning an S&P 500 index fund over the long term is fine too.Just know that the longer you rent,because ofinflation,the longer you will regret your decision.Inflation isan unstoppable beast that will eat you alive.

Real estate is also less risky than stocks. Therefore, I have more of my net worth in real estate than I do in stocks. Ironically, I think most of us can also end up making more from real estate.

3) Think in percentages over absolute dollars.

Because I had never invested more than $500,000 a year in my life, having nearly $1.8M to re-invest was intimidating. But as soon as I started breaking the investment amount into percentages, deploying capital became easier.

Find out what each asset class is as a percentage of your net worth and calculate what each new investment is as a percentage of your investable assets and net worth. This exercise is particularly helpful for frugal people whose wealth has far outstripped their spending habits.

4) Stick to an investment framework no matter what.

Once you've decided how much you can comfortably invest each month and what type of asset allocation is best for you, execute your plan without fail. It is almost always the case you will be surprised by how much you end up accumulating or how much debt you end up paying down over time.

5) Make a positive change during a bull market.

Remember, there needs to be a purpose for your investing, otherwise there's no point taking any risk. Perhaps you can now update your target retirement date earlier. Or maybe you can expand your list of target schools for your child now that you're a little wealthier.Always focus on the end goals for why you invest.

Investing Lessons 2017 – Wrapping Things Up

Investing Lessons From A Surreal 2017 (5)

According to the final weekly personal investment performance e-mail I get from Personal Capital, my public investments returned 15.87% in 2017. I'm happy with the results because my total capital exposure is significant relative to how much we spend. Further, my goal after leaving work was to earn a 4% – 6% tailwind a year while I build a lifestyle business, which has frankly trounced the market’s return each year since inception.

It's really hard for me to take on more risk because of my fear of having either one of us go back to work during the crucial first five years of our son's life. At the same time, I can't help but want to take full advantage of the bull market while it lasts. The further I can run up the score, the bigger the buffer during the inevitable recession.

Finally, one positive surprise I experienced this year was that once I elongated my investment time horizon to 20+ years due to the birth of our son, I became much more at peace with my risk exposure. To invest for someone's future feels wonderful.

Related posts:

2018 Review

2019 Review

2020 Review

Invest In Private Growth Companies

Finally, consider diversifying into private growth companies through an open venture capital fund. Companies are staying private for longer, as a result, more gains are accruing to private company investors. Finding the next Google or Apple before going public can be a life-changing investment.

Check out theInnovation Fund, which invests in the following five sectors:

  • Artificial Intelligence & MachineLearning
  • Modern DataInfrastructure
  • Development Operations(DevOps)
  • Financial Technology(FinTech)
  • Real Estate & Property Technology(PropTech)

Roughly 35% of the Innovation Fund is invested inartificial intelligence, which I'm extremely bullish about. In 20 years, I don't want my kids wondering why I didn't invest in AI or work in AI!

The investment minimum is also only $10. Most venture capital funds have a $250,000+ minimum. In addition, you can see what the Innovation Fund is holding before deciding to invest and how much. Traditional venture capital funds require capital commitment first and then hope the general partners will find great investments.

Investing Lessons From A Surreal 2017 Is A Financial Samurai original. Check out my Top Financial Products Page and subscribe to my free newsletter to help you achieve financial freedom sooner.

Investing Lessons From A Surreal 2017 (2024)

FAQs

What if you invested $1000 in Microsoft 20 years ago? ›

Buying $1000 In MSFT: If an investor had bought $1000 of MSFT stock 20 years ago, it would be worth $16,279.07 today based on a price of $413.00 for MSFT at the time of writing.

Which stock will double in 3 years? ›

Stock Doubling every 3 years
S.No.NameCMP Rs.
1.Guj. Themis Bio.385.80
2.Refex Industries155.75
3.Tanla Platforms932.50
4.M K Exim India78.55
10 more rows

Which questions should Robert ask himself before investing the 10000 he inherited? ›

Robert should ask himself how he is protected as an investor, what taxes he will need to pay on his investment, and how do the risks compare to the potential gains.

What is the 1 rule of investing? ›

Warren Buffett once said, “The first rule of an investment is don't lose [money].

What would $1000 invested in Apple in 1990 be worth today? ›

Therefore, if you had invested $1,000 in Apple stock in 1990, it would be worth approximately $598,972.50 today.

How much is 200 dollars a month invested for 20 years? ›

If you can invest $200 each and every month and achieve a 10% annual return, in 20 years you'll have more than $150,000 and, after another 20 years, more than $1.2 million. Your actual rate of return may vary, and you'll also be affected by taxes, fees and other influences.

Which stock will boom in 2024? ›

Best Stocks to Invest in India 2024
S.No.CompanyIndustry/Sector
1.Tata Consultancy Services LtdIT - Software
2.Infosys LtdIT - Software
3.Hindustan Unilever LtdFMCG
4.Reliance Industries LtdRefineries
1 more row
Apr 9, 2024

What is the most profitable stock in 5 years? ›

Best Performing Stocks Over the Last 5 Years
TickerCompany Name
1CELHCelsius Holdings
2SMCISuper Micro Computer
3NVDANvidia
4ELFe.l.f. Beauty
6 more rows
Apr 1, 2024

What stock will double in 2024? ›

2 Stocks That Can Double Again in 2024
  • SoundHound AI and Sweetgreen are up 174% and 116% so far in 2024.
  • SoundHouse AI is seeing its platform for conversational intelligence explode in popularity.
  • Sweetgreen has quadrupled over the past year, but it's still a broken IPO with potential to harvest.
Mar 27, 2024

What is one simple rule to follow if you want to create wealth? ›

Never Spend More Than What You Earn

If you spend more than what you earn, you will never be able to start on your wealth creation journey.

What Benjamin Graham taught Warren Buffett about investing? ›

Buffett has those rules because the value investing approach he learned from Graham follows three core, risk-mitigating principles: Always analyze the long-term evolution and management principles of a company before investing. Always protect yourself from losses by diversifying.

What are the Warren Buffett's first 3 rules of investing money? ›

Some of his most important rules include:
  • Rule 1: Never lose money. This is considered by many to be Buffett's most important rule and is the foundation of his investment philosophy. ...
  • Rule 2: Focus on the long term. ...
  • Rule 3: Know what you're investing in.
Mar 6, 2024

What is Warren Buffett's golden rule? ›

Buffett's headline rule is “don't lose money” and his second rule is “don't forget rule one”. This might sound obvious. Of course, it is. But it's important to look at the message within.

What is the golden rule of money? ›

The basic principle of the golden rule of saving money is to save at least 20% of your income. This includes any form of income, such as salary, bonuses, or freelance earnings. By consistently saving a significant portion of your income, you can build a strong financial foundation and achieve your financial goals.

What are the 4 golden rules investing? ›

They are: (1) Use specialist products; (2) Diversify manager research risk; (3) Diversify investment styles; and, (4) Rebalance to asset mix policy. All boringly straightforward and logical.

How much will $1,000 invested be worth in 20 years? ›

As you will see, the future value of $1,000 over 20 years can range from $1,485.95 to $190,049.64.
Discount RatePresent ValueFuture Value
20%$1,000$38,337.60
21%$1,000$45,259.26
22%$1,000$53,357.64
23%$1,000$62,820.62
25 more rows

What if you invested $1,000 in Microsoft 10 years ago? ›

So, if you had invested in Microsoft a decade ago, you're probably feeling pretty good about your investment today. A $1000 investment made in February 2014 would be worth $11,326.86, or a gain of 1,032.69%, as of February 9, 2024, according to our calculations.

What would $1000 invested in Microsoft in 1986 be worth today? ›

Microsoft's return is even more impressive than Apple's, as it turned $1,000 invested in its 1986 IPO to $4.1 million now.

How much money you d have if you invested $1000 in Microsoft 10 years ago? ›

Had you invested $1,000 in Microsoft 10 years ago, you would have turned a hefty profit by today. According to computations by CNBC, that modest amount would already have been worth $11,400 as of Nov. 9, 2023.

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