
Lately, we’ve been considering a “permanent portfolio” which simply means a new way to invest that avoids large ups and downs. Since we started this blog about 7 years ago we suggested dollar cost averaging all of your money into the S&P 500 if you are not rich yet (after the basic cash buffer is made). That is still a good strategy if you’re young but we recently stopped investing in the stock market (end of last year) and have simply been moving to cash/crypto since then. Why? Well if you haven’t been working/selling items for your own company since 2008… it means you haven’t seen a recession. Recessions are the best time to get rich since everything goes “on sale”. Long story short, our 2021 recession expectation (rough range), is the last recession we’re attempting to “time”.
General Principles: Before jumping into what a permanent portfolio would look like, we have to explain why it’s possible to create one. The reality is that anyone who is a millionaire by 30, will have high income/cash flow… otherwise they wouldn’t have made it to a million dollars so quickly. This part is usually confusing to someone with a normal income since your monthly cash flows can quickly equal a year of savings for median wage earners. What does this all mean? It means you can *move* your allocation without actually selling any assets. As a simple example if you have a million dollars equally split between four asset classes ($250K each), but you are able to save $25K in a month… By simply putting it all into one asset class for two months you have “rebalanced” your portfolio by a few points (it would represent 28.5% instead of 25% in just 2 months).
This is a significant advantage for you (if you’re in this situation). Said a different way, one part of the entire portfolio could go down a full 10% ($250K goes down to $225K)… But you could simply take all your earnings for a month and toss it into the basket to rebalance to 25% (all else equal). This example alone should explain why we think individuals should not waste time looking up “the next big thing” until they are officially rich. If you simply close your eyes and buy the major asset classes (stocks/bonds/real estate/crypto/gold), you’re going to do fine and are better off making large amounts of money before attempting to time out your purchases more. Your monthly purchase will equal your old annual purchase if you focus on becoming rich the right way (sales, ownership or tech).
A Recession is Simply Opportunity: If you’re successful the chances of being employed/making decent money during a recession is quite high. Why? Well this is how life works. Recessions are painful for most, yet the ultra successful stay insulated. They are able to find employment since they are actually delivering value (unlike most within the Company or Industry if you run your own business). This gives you a chance to buy talent at a discount (high quality people who were cut due to office politics vs. performance) and it gives you a chance to buy assets that are deemed “too risky” even if the business model is completely unchanged long-term. A good example of this is when the housing bubble crashed, that created a “cloud of worry” around rental income and people decided that homeownership was “not for them”. Of course… this ended up being the best possible time to buy since people still need somewhere to live over the next 50 years. In short, watch the news closely during the down turn (seriously!) and if they say an industry is “forever changed and this time it is different” look into that industry because it usually isn’t. Funny enough this even worked during the tech bust, when the view was that the values were forever going to be deflated, meanwhile the top companies that actually survived and thrived are worth significantly more than they were back in the 2000-2001 period.
A New Permanent Portfolio: The world continues to change rapidly, about 15 years ago smartphones were not pervasive and there was no such thing as crypto currency. So the way we think about a “permanent” portfolio is to have sub-segments along with a ‘alternative class” where you buy small amounts of any emerging future company/asset class. Who knows, maybe the next best investment will be real estate on another planet (seriously, anything is possible over a 50-100 year frame). The chances of this happening are slim but being prepared for structural shifts is the whole point of a permanent portfolio. The second most important piece of a permanent portfolio is “no stress”. You’re creating a permanent portfolio to simply increase your net worth over time and no longer think about money in the future.
Pause for a Second: Before any confusion arises, everything outlined in Triangle Investing is till valid. If you’re not rich yet, you’re better off just dollar cost averaging into stocks, real estate and crypto. When we refer to “dollar cost averaging” into homes, it means you’re just taking a portion of your net worth every year to buy some sort of rental property (or any other asset that is real estate focused). This post is meant for two different strategies we’ve been mulling on once you’ve hit your financial independence hurdle. We have to emphasize that point. This post is for people who are looking for new ideas once they are set and there are really two clear paths: 1) a permanent portfolio and 2) a strategy to get your plan A. We can’t think of a third plan so it really turns into a permanent portfolio and a high risk plan A.
Permanent Portfolio
Since retirement makes no logical sense as your brain erodes from lack of use, we assume that you’ll always be doing something for money. If you follow our plan for a million dollars within 10 years, the math suggests that you will eventually be worth ~$10M in the future due to compounding and continued effort (you didn’t get to a million with a low income!). This is a great set up but does not answer the obvious question “what type of life do you want to live”.
If you are not interested in driving lambos and traveling on private jets or first class at all times, the permanent portfolio is likely better for you. This is similar to what is known as an “equal weight” portfolio. There are many other names for it including the “Quattro” strategy. The basic premise is as follows: there are 4 clear asset groups for active management – 1) stocks, 2) bonds, 3) cash and 4) gold. Remember this is based on legacy portfolio management theory and does not include new markets like crypto currency.
How does it work? You simply put 25% of all of your income into each of the four groups. At the end of the year (or twice a year), you sell the winners and re-buy some of the losers to rebalance at 25%. Since gold goes up during recessions (historically) and stocks go up during upturns, this naturally allows your portfolio to grow over time. Will you get rich off of this? No. Will you go broke off of this? No. This is the point of the strategy as it reduces risk for you over long periods of time. Also. This strategy is also perfectly fine if someone does not want to think about investing while they grow their business.
Fast Forward to 2019: At this point the world has changed quite a bit. While the equal weight strategy will likely work, we think it makes more sense to have something that is much more “future friendly”. This means you’re going to have more assets to actively reduce the chances of missing out on the “next big thing”. People who missed out on Bitcoin at prices below $1,000 for example are still trying to play catch up. So we’ve come up with a percentage that should work as a new “permanent portfolio” for the next 50 years or so and it looks something like this: 25% Stocks, 20% bonds, 20% Cash, 20% Gold, 10% Crypto and 5% alternative assets. The emphasis here is that this balance refers to all of your invested assets and does not refer to real estate since we view that as a separate entity entirely (since you can have forced returns where you actively fix it to improve the performance). For those that want to nit-pick, what usually happens is that the person will own a couple of properties (one he lives in) and one or two rentals at minimum.
Rebalancing: Since our portfolio is a lot more complicated when compared to the standard portfolio, we would only rebalance once a year. When you think about it this will also allow you to “ride your winners” longer and also forces you to sell the big winners at higher levels. Selling and rebalancing is costly not just in fees but time as well (tax issues also occur due to1 year holding periods). The losers in the portfolio are unlikely going to impact you since the volatility is tied to the crypto, stock and alternative asset pieces which are a smaller chunk of the overall portfolio.
Final Note on Permanent Portfolio: The biggest downside of the permanent portfolio is that you’re not actively learning about new things. You’re creating a portfolio that will go up over time and makes sure that you will be able to slightly increase your spending for the rest of your life. The biggest upside is that you are free to do anything you like with your free time: spend hours on the beach, travel, sleep in, work less and read less. While this sounds like hell to people who are still trying to work their way to the top, a permanent portfolio allows you to sit back and decide on what you would like to do next. So. Remember this set up for the future since its a good way to put “time on hold” if you ever need to.
Aiming for a Big Plan A
The second idea we’ve been ruminating on is the “Plan A” portfolio with extra money. One of the main items from this blog is that we’re recommending a basic strategy to get modestly rich that will work for anyone. It does’t require immense talent it just requires a lot of work and reflection. What are you good at, find that skill, work long hours for the first 3-5 years of life and hit your basic financial independence number. Only people who absolutely “must” be worth $100M+ would not follow this plan. They would go down the full ownership route on day one as that is the only way to really get rich (starting and running a company).
Investing for Plan A: Making the numbers up we assume that you’re worth $5 million. At this point you can generate around $250,000 pretty easily with just 5% returns. That’s more than enough money for the vast majority of people but lets go ahead and say that you have bigger goals in mind. If you want to try and make another leap the only way to do so is through serious concentration. Mainstream financial advice always says to “diversify” but the people who get rich do so by selling their companies and owning a large chunk of it.
What does this mean? It means that your alternative strategy is to simply go all in and swing for the fences. If you already have $5 million and that is enough for you personally, then it is time to go ahead and take all your future income and put it into risky investments. This is not something “mainstream” advice will tell you since they always go with the lower risk answers.
Venture and Angel Investing: You guessed it. Getting in early is the only real way to get outsized returns. One of the most important changes over the past 10 years is that individuals can now invest in early stage companies rather seamlessly. You don’t have to wait for the Company to go public and you don’t have to wait for a major round. All you need to do is make contacts and offer a large investment in the first fund raising round. The key here is that you need to be right at least once. If you’re right once with a large initial investment of say $100,000 (a large sum for a first round raise), you can get a return that is well in excess of 10x.
As you can imagine… This is the direction we’re choosing. This is not a recommendation as there is nothing wrong with a permanent portfolio or a 10% annual return on all of your money. We’ve reached a point where working an extra year and saving it into index funds, or cash/bonds doesn’t make any impact to daily life. What is the point in increasing your monthly spending by around $500-1,000 (again making the number up). You’re only going to live a different life if you’re able to double or triple your monthly spending and at some point you will hit scale issues. Adding 50% to multi-million dollar portfolio with work is much harder than adding 50% when you only have a couple of hundred thousand dollars to your name.
Unsurprisingly, this change in strategy is slowly bleeding into the content on this blog. Prior to 2016/2017 we focused a lot more on compounding investments to make sure there was enough buffer room to sustain a recession. We’re past that now. A 50% drop in the stock market, bond market and real estate market would not impact our lives. In fact nothing would change except the numbers on the screen since a 50% decrease in cash flow still allows for financial independence. Many will say that is a brag which is fine but it’s more of a “change in situation”. Take a step back and ask yourself, if you knew that someone would hand you enough money to pay for all food, clothing, travel, housing and healthcare expenses for the next 200 years… Would you personally be interested in an extra few hundred dollars a month? The answer is probably no which is why our thought process and ideas are starting to move away from the original strategies on the blog.
Time for Change “Quitting”: We recently wrote that one of the most important skills is learning to quit. Another person on Twitter used the phrase pivot but the concept is the same. We’ve realized that once you hit a certain net worth, the impact of making 5-10% gains is not interesting anymore. While we won’t do anything crazy (touch the principal), there is no reason to take all future income and buy the same old stuff. So we’re quitting the low-risk low-reward portfolios going forward. The strategy is to attempt to reach the “next level” which requires doubling or tripling net worth and the only way to do that is … you guessed it… by taking on more risk! Surprise surprise. As a fun note, as we’ve mentioned the last 8 months, we have stopped investing more money into stocks and our current cash flow has been going into only cash and crypto. By the end of the year we intend on putting a large investment into a high risk asset. Once this happens we’ll likely explain the process on the blog. No. Most people won’t like the articles. But. We can’t really do anything about that as its the direction we’re going.















This is an excellent post. Actionable for the single-digit percentage of your readership who have made the number, and should fire up the rest who are still working on it.
The articulates my own experience incredibly (actually eerily) well. Work hard (way longer than 3-5 years but hey I’m slow?), build financials, have an exit and make the number. Then experiment with a bunch of stuff including consulting (after you have some success people throw money at you to learn your secrets)… only to realize the headaches aren’t worth it for something that gives you some extra spending cash but doesn’t move the needle.
I personally have settled on early-stage investing, like you guys. The only point I can add too all of the above is that it generally takes a long time – a decade or more – for those 10xers to happen (there is only one Instagram (18 months from launch to $1b), if they do at all, so be ready to be patient. And portfolio theory/power laws are such that you need to make a lot of these investments over time, so that 5% AA better be off a real base ($5m or more).
Hilarious that right after yours another guy chimes in saying worst post hahaha
Anyway, if you find another strategy to move the needle besides business start and high risk investment let us know. we’ve been looking for a year now and it seems like those are the only two ideas
Not the route I’d take and good luck to you all but probably my least favorite post of y’all’s so far. For all the talk about life changing/generational money you guys harp on, it doesn’t seem like you come from it/surround yourself with multi-generational wealth. I’d just like a response as to why you wouldn’t play the long-term growth game in the macro-environment? Obviously you want to be extremely concentrated in those equities but if you manage to pick the dominant companies in emerging industries then you’ll be richer than you could ever imagine. Take $20 million. Compounded at an extremely conservative 15% (look at historical ROE for top companies in their respective fields over a number of years) for 20 years nets you almost $400 million without any deposits. It just seems with your timeframe and expenses that you could invest on an indefinite time frame and ride any short term pain away. This is all contingent on you guys being incredibly savvy macro investors, but if you are as smart as you let on then playing the long macro game shouldn’t be a problem. Cheers
No we did not come from money that’s well known grew up below poverty line.
Since we’ve been poor before no interest in ever having that happen again. So the only way to swing for us is to take future cash flow and take levered bets on the future.
Under no circumstances are we going to bet principal ever again. Being poor is not fun and only people who have never been poor will be wiling to risk it all to get back to that horrific situation. To each his own in terms of strategy, our post is only an opinion not the end of the world
Your response is rather disingenuous. Care to address the question posed? You’re smart in a conservative kind of way in not risking principal but unless you’ve got millions of dollars in cash flow rolling in then you’re not likely to see these moonshots pay off more than a concentrated macro portfolio. If you are bringing in a positive 7 figure cash flow then my point is moot as you have more than enough to take sizeable bets doing what you propose. If not, little chance.
You answered your own question = )
You are correct if cash flow changes strategy has to change to level up
Going on with the NASDAQ bubble analogy, I’d guess that a lot of the crap-tier crypto projects will disappear in the next recession, with headlines to the effect of “Is crypto doomed?” But, the survivors will end up being the anchors for the blockchain economy, which I agree with you has large potential, especially with smart contracts.
Have you tried Wefunder or Nextseed by chance? Any thoughts or opportunities you’ve seen on those platforms?
Great Post! First time visiting your blog.
Do you see any value in creating a brand to angel invest?
Ex: Jason Calacanis from This Week in Startups podcast, Naval from Angellist, Harry from 20 min VC?
They have brand recognition and platforms where they help market the startups they invest in. Looks like their worth just compounds because not only do they make money from the platforms(podcast, website), their brand recognition helps attracts great founders?
This is not a Q&A… we do Q&As once a month for purchasers of our products only.
Great post. As far as your last tweet…I guess you guys don’t believe in the law of attraction…
I honestly think the law of attraction is one of the dumbest things ever. There’s no way having intense thoughts itself will lead to what you desire.
MSCI.
Emerging markets contain the majority of the world’s millennials.
Now answer my Question:
When is the new style/fashion book coming out? 😉
Hi Wall Street Playboys,
Big fan of yours, and your wisdom has encouraged me to start my own company. Let me get straight to the point. I’ve played a key role in multiple projects that have generated $1B+. I have an idea which I think has a solid shot at $100M+ in annual revenue. I’m creating a small company and working on a key partnership at the moment, and all this will cost less than $500k which I can self-fund, but still looking to extend my team’s runway. The beauty of my ask is that outside of an initial small risk of $50k or so (which you may not even have to invest, just temporarily tie up your money for 30 days), you could have equity of a very scalable product. If you’d like to know more, I’d be happy to discuss my background more (which you can figure out from my email). Just a note though, still working on signing the deal with my potential partner, so it will be at least 3 weeks or so before I can discuss the entire plan. I’m a bit premature on this because I still need to sign this deal, but I sense an opportunity so yeah I’m teasing it…
“If you want to participate, send me 5 BTC to the following address..”
Haha. Classic.
Great timing on this post for me. I’ve been looking at a lot of risk parity strategies for my own money lately.
Have you heard of Ray Dalio’s All Weather Strategy? His views on risk parity may interest you as he had this problem himself in the 90’s for building a portfolio for his family after he was gone.
The formal version is for institutional clients, but for everyone else he recommended: 40% long-term bonds, 30% stocks, 15% intermediate-term bonds, 7.5% gold, and 7.5% commodities. Rebalance yearly or when convenient. You can google it yourself I’m sure.
The idea is it’s good for anytime inflation is higher/lower than expected and growth is higher/lower than expected. Only time it’s bad is a great depression, but it still does better than 60/40 bonds and central banks can just print money to end it.
If you want higher returns, you can lever it up for the same returns as an equity portfolio, but still have lower risk than just pure equities.
Anyways, you’re probably good, but felt like sharing. Good luck on your VC moonshot! Looking forward to your lifestyle posts on the right ways to fly private or the insiders guide to yachts in a few years :).
Keep us posted. Nice to see you all making progress too. You deserve it given how much you’ve paid it forward over the years.
Here are the high risk/reward plays I’m currently invested in:
– Early investment in e-cig company
– Small equity stake in real estate development company in SE Asia
– Bankrolling advantage players in Blackjack and other positive EV gaming
– Pot stocks
Will say that in all these circumstances minus the pot stocks, it was my strange collection of networks that introduced me to these opportunities. I sort of fell in line with the main guys in each venture who decided to bring me in because they felt I was trustworthy. Still in the early phases of all of these so will see how it goes.
Interesting thank you for the comment!
Thanks for this great post.
I have been following your advice, and made good progress in my city career. I know that most of this advice is meant for the US, but I am sure that there are also many UK based regular readers like myself.
So I will give another helpful piece of information: If you are a UK taxpayer, investing in a small company is insured by the government to encourage more venture capital.
https://www.gov.uk/guidance/venture-capital-schemes-apply-to-use-the-seed-enterprise-investment-scheme
As an investor, you get 50% of your investment back from your taxes in the year of your investment and another 25% if company goes bust.
If the company turns to out to be productive, it is difficult to beat these returns.
Good post. Have invested in small vc plays in the past. Of course some have worked and some haven’t. Liquidity event (ipo) or potential for positive CF important for return. Overall made an ok return but not life changing. Perhaps lack of skill as not my field.
The thinking is correct, concentration is the way to outsized returns. Leverage is another way to juice returns – options/futures are great instruments where I have been much more successful consistently.
I agreed with your post that equities/risk assets looked expensive last year – a levered bet on treasuries/duration has made me 70% returns since. Obviously only on that risk pocket, but my point is if you have a ‘risk budget’ you can apply it to a number of things depending on your skills/network and of course the opportunity set.
Best of luck and curious to follow the vc play
If you’re bearish on the market then put ~0.5% of your net worth into long-dated long put positions. Likewise on the bullish side with calls.
And then you can spec out a few individual longs (and limit losses) by buying some OTM call options. Most options expire worthless (which is why regulars always sell options lol) but the ones that don’t can offer monstrous returns (paraphrasing Nicholas Taleb).
You can do this in a way that requires a lot of time/attention or in a way the requires next to no time (e.g. roll out new options the same day you do your rebalancing), whatever floats your boat.
Hi I’m an early 20s software engineer who was able to get a remote job paying ~150K cash with 30-40hrs / wk. Would I be better off trying to start a business on the side, doing freelancing on the side or trying to get a 200-250K job in the next year or so (will obviously not be remote). Reason I’m asking is I need to make at least 400K/yr where I live to be ok.
Would appreciate your input.
Not a q&A.
More risk means more work. There’s a definite change from previous articles, where you warned against chasing the high of making more money.
Will ask on next Q&A what motivated this shift.