5 Tribes of Investors


A few years ago, Lee Freeman-Shor was an institutional asset manager with access to significant resources. He funded accounts with 45 of the world’s top investors and requested that they each hold no more than ten stocks. The purpose was to focus on "best ideas."
Over the next seven years, Freeman-Shor then reviewed every single trade (30,874 of them!) and published the results in a must-read classic for investors, The Art of Execution.  
Freeman-Shor’s study found that only 49% of their investments were profitable, and that some “legendary” investors made money on fewer than 30% of their trades.  
How can you make money by being right on 1 out of every 3 trades? Is it still possible to win, even if you wrong most of the time?
He realized that successful investors knew instinctively what to do when a trade was working against them. They didn’t just sit with losing positions…. they did something.Some bought, others sold, but they all took some kind of action.  
Digging into the decision-making process of the world’s top investors Freeman-Shor identified five key “tribes” of strategy: “Assassins”, “Hunters", “Rabbits”, “Connoisseurs”, and “Raiders”.
Assassins are the calculated “killers” of portfolio management. They excel at limiting their losses and moving on to the next opportunity.
Assassins have no attachments. When they buy a stock, they determine how much they are willing to lose before cutting their losses. Once that line is crossed, an investment is sold. No exceptions.
  • Typically, assassins might lose between 20-30% on a stock position before they stop the bleeding. 
  • They will also sell stocks if that haven’t generated a gain within 6-12 months after the original purchase.  
A typical assassin’s portfolio will often have “stop loss” orders. These are a special type of "sell" order that is automatically executed if a stock drops below a certain level. 
By getting out of losing investments quickly, assassins have more opportunities to find the next big winner.  
Hunters watch their stocks carefully and buy during moments of weakness. 
  • If a stock drops by 20%-30% from the original purchase price, they double-down and buy more shares. 
  • If a stock drops by 40% from the original purchase price, all shares are sold.  
Hunters typically will take smaller initial positions. This keeps cash available for them to “buy the dips”. On the second round of investments, hunters typically purchase the same dollar amount as the first round. This means buying more shares at a lower price. It’s a basic form of dollar-cost-averaging that tilts stock volatility in their favor.  
While hunters and assassins have seemingly opposite strategies, they both have a discipline and stick to it. As you might guess, it is impossible to be both a hunter and an assassin. You are either one or the other.  
Rabbits are the least successful tribe of investors.
  • Rabbits dig holes so deep that they never see the light of day again. This means that their losses become large enough that they can never recover.
  • Rabbits buy stocks, but never update their research or change their mind. They just keep telling the same stories over and over again.
  • Rather than admit to being wrong, rabbits simply run away from the problems in their portfolio.
So, with rabbits there is no exit strategy. The problem with holding onto extraordinary losses is that they require an even more extraordinary gain to recover. After taking a 90% loss, a stock requires a 900% gain in order to break-even. The odds of that ever happening are minimal to non-existent.
Being a great investor goes beyond knowing what to do when things go wrong. It also requires knowing what to do when investments become profitable and things go right. There are two strategic archetypes for success – the “Raiders” and the “Connoisseurs.”
Raiders are too hasty in selling out of winning positions.
  • Raiders are “in and out” of their investments, hoping to make a quick profit.
  • Emotionally, selling for a small short-term profit usually feels great. Unfortunately, this is a strategy for losers. 
Freeman-Shor found that many investors will start selling a position after making a 20% gain.  
The study found that 60% of the investments that were sold for a profit of 20% or less continued to see higher prices after the sale. Raiders are often too hasty and often leave a lot of money on the table.
If you keep taking small profits, you will never have a big winner.  
Connoisseurs know how to enjoy their gains.
  • Connoisseurs prefer to invest in quality businesses that generate steady, predictable earnings.
  • They savor their best investments. Connoisseurs will toss out the swill early on, but let the finer vintages age in their collection.
  • Connoisseurs tend to be hoarders. On special occasions, they might pull out a bottle from their collection for their enjoyment, but they will almost never consume (sell) everything at once.
  • When connoisseurs find something good, they will hold a lot of it. They know what they like. Instead of keeping a bottle or two, they'll have an entire crate. As a result, some connoisseurs have a significant portion of their portfolios in just one or two stocks.
Most successful investors start out as Assassins or Hunters before they are able to find their first big success. At that point, they may “graduate” and mature into Connoisseurs. It’s usually OK to take some small losses, so long as you can also generate a few big wins. The key here is to keep your failures survivable and to make your wins especially rewarding.
Jim Lee, CFA, CMT, CFP®
Founder, StratFI
Disclosure: Information contained herein is for educational purposes only and is not to be considered a recommendation to buy or sell any security or investment advice. 


(A brief note: When a local tech journal asked us to contribute an article about workplace trends, we decided to write a spoof employee handbook.  Here it is...)


Hello, new employee!

Welcome to your first day at IdealCorp, Wilmington’s hottest new SoLoMo fintech maker startup. We’re on a path to ridiculously incredible growth and that’s because of the amazing culture we’ve been building.

Unlike other companies out there, our employees come first. That’s because we want the people on our team to give us the best one, or maybe even two, years of their lives working with us.

How are we able to retain people for so long, you ask? You’ll understand as soon as you leaf through our handbook. Yes, it is printed on artisanal paper from local pine trees. And yes, we do need it back.

But for now, we hope it helps you imagine what your life will be like around the office.

Welcome to the team.


Dress Code

At IdealCorp, we recognize the nobody knows what to wear to the office anymore. So, there is no dress code. Just come as you are, and express yourself! However, on Fridays, employees are encouraged to wear unicorn horns, fairy ears, pajama bottoms and flip-flops to create a more casual and stress-free work environment.


We are pleased of offer a full range of employee benefits. These benefits include, but are not limited to unlimited amounts of coffee and kale-themed beverages, an avocado bar, and access to our listening booth just in case you want to “zone out” for a while.

Quantifying Success

Employee evaluations have always been so… awkward. At IdealCorp, we’ve replaced all of our bosses with algorithms! These are programmed to be completely, fair, unbiased, and nonjudgmental. Note that in order to keep-up with the ever-changing consumer landscape, these algos will be periodically updated to appear fickle and arbitrary.

Financial Transparency

We’re still assessing if revenue is a positive or negative, so we prefer to say that every quarter is a “really great” quarter. Auditors regularly call our accounting “amazing” and “incredible.” Believe that.

Our track record shows that bigger spending leads to greater funding. This enables us to spend even more on over-the-top ideas. We call this the VC, or Virtuous Cycle". Our objective is to keep the VC’s going for as long as possible.

Continuing Education

We recognize that your career is a big commitment, and might last as long as three years. To maintain a competitive and “edgy” workplace, we offer no employee training – whatsoever! Instead, we offer free, UNLIMITED access to the public library.


Bring your own device, and we’ll give you free stickers.

Better communication means more communication platforms. We embrace all of them as equally effective means of staying in touch with one another. So, we regularly use Fleep, Ryver, Flock, Hash, Twist, Chanty, Slack, Skype, Zoom, and even Google+!

All passwords must contain letters, numbers, doodles, emojis and chipmunk sounds.

Your Work Environment

Time is money and space is time. We provide a completely open office floor plan in our newly renovated warehouse. In recognition that our valued partners are actually full-time art students at DCAD, all new employees are given an IdealCorp backpack (loaded with swag!) and a locker.

While working at IdealCorp, you’ll find that the line between working, playing, and sleeping will become very, very blurry indeed! We offer showers, free laundry service, and surrogate roommates so that you’ll never need or want to go home. Ever.

Reprinted courtesy of Technical.ly Delaware.


The End of Asset Allocation?

  • Jim Lee

If you find yourself reacting to the news… you might not be doing it right. It is much more useful (and profitable) to anticipate trends in advance than it is to respond to the morning’s headlines.

When people talk about investments at cocktails parties or social gatherings, the conversation almost always veers towards “How do you believe that X will influence Y?”
The “X” in this case is always the hottest news item, and “Y” is typically the investment that is receiving the most press coverage.

Watching CNBC or Bloomberg News, you’ll get a good sense of the market’s mood for that moment . Market commentators will scramble to explain why today’s big story is moving the markets. When a story occurs for several days (or weeks) in a row, it becomes a source of public obsession. Eventually, that story becomes the most important thing moving the markets. Everyone becomes an expert in understanding the topic at hand, until the issue is resolved and the markets move to a new narrative.

It is worth mentioning that portfolio managers have relatively little control over client returns. If it was easy to control returns, we would always choose to generate spectacular profits. Right? Investing would become tedious, because everyone would have equally amazing performance.

What can be controlled is exposure to opportunity and risk. And the traditional way of doing this is through something called "asset allocation", which is part of a much bigger framework known as Modern Portfolio Theory (MPT).

The principle is fairly straightforward. By putting together a portfolio of non-correlated assets, you can hypothetically create smoother returns for investors.

Asset Class Returns 004

In the example above, we compare the performance of the S&P 500 index (dark blue) with the 20-year U.S. Treasury Bond (light blue). The middle line represents a balanced portfolio which is equally invested in both. The time period illustrated is 1956-1962, shortly after Modern Portfolio Theory was developed by Harry Markowitz in The Journal of Finance.

It was a beautiful and elegant idea. Asset allocation created a new standard for the industry and is still in use today.

One of the useful things about asset allocation was that it enabled financial advisors to be agnostic about the financial markets. It was no longer considered necessary to anticipate (or respond) to the news. All the advisor needed to do was "stay the course" and periodically rebalance portfolios to a target allocation.

Meanwhile, investors had less portfolio volatility. Mutual funds had lower asset turnover, because investors stayed invested for longer periods of time.

This was the real genius behind asset allocation. It kept everyone happy (for a while).

The Limits of Asset Allocation

As a portfolio manager, I started to see the limitations of asset allocation during the Financial Crisis of 2008-2009. During that period not only did the S&P 500 lose half its value, but bonds were down, real estate was down, and commodities were down. "Winning" simply meant "losing less." The only major asset class that didn't lose value was... cash.

Now that the S&P 500 is over 10% off from its peak levels earlier this year, we are seeing similar parallels. Many traditional asset classes are becoming correlated - right when we want the benefits of diversification.

Asset Class Returns 1 Yr 002

In the chart above, all major financial asset classes show some correlation to the S&P 500. There is a slightly negative correlation between the Barclays Aggregate Bond index and the MSCI Emerging Market index. Beyond that, everything else "sinks or swims" together.

Furthermore, the S&P 500 consistently outperformed most other asset classes over the past five years (and for the first half of this year). Attempts to diversify against U.S. market risk have generally produced performance lag, especially for those portfolios holding exposure to international and emerging market stocks. Bonds have lagged more recently, as a result of higher interest rates.

Asset Class Returns

Asset Class Returns 005

Asset Class Returns 003

Source: www.novelinvestor.com

This isn't saying that asset allocation is dead. If the current market correction evolves into a typical bear market, investors using some form of asset allocation may see less downside.

My sense is that asset allocation may be inadequate on a stand-alone basis. People are starting to figure this out. There are other useful tools of risk management, and these include style/sector rotation, investment selection, hedged strategies, and market timing. This is a benefit of having an independent investment advisor for your portfolio, as traditional index funds don't do any of these things.

Jim Lee, CFA, CMT, CFP ®

 Disclosure: Information contained herein is for educational purposes only and is not to be considered a recommendation to buy or sell any security or investment advice. Securities listed herein are for illustrative purposes only and are not to be considered a recommendation.


Rock Paper Scissors

Investing used to be simple. You would go out and buy and index fund, and then forget about it for the next ten years. It’s easy and inexpensive. This is called a “passive” strategy because you really didn’t need to do anything, beyond making the initial decision.

But not all index funds are created equal. While the Vanguard S&P 500 Index is still the largest mutual fund in the known multi-verse, there has been an explosion in what can be described as “enhanced” index funds. These are based on a few simple principles that have been shown to generate out-performance over time.

Enhanced index funds exist in something of a gray zone between “passive” and “active” strategies known as “factor” investing. It is an approach that fits well with the rising trend of robo-advisors coming into the marketplace today.

Based on Morningstar research, there are now 1,500 single-factor ETFs on the market. These can be categorized into five basic varieties….

Factor Boxes 007

Once a factor is identified, a custom index can be built by screening for stocks that satisfy the selected definition.

I’m beginning to see your eyes glaze over… but wait, this is really interesting stuff!

Looking back at almost 40 years of data, these five factors do appear to generate some outperformance over time, mostly in the 0.3% to 1.5% per year range.

Factor Boxes 008

The Size factor generally seems to provide the best returns, in exchange for the greatest risk. Meanwhile, the Low Volatility factor doesn’t seem to outperform over time, but does offer great protection during down periods. Both seem to be good, but each one is best under different circumstances. Furthermore, no single factor performs best every single year.

What ends up happening is a fairly highbrow game of “rock, paper, scissors.” You never know which one is going to win, so many portfolio managers choose a mixed strategy of factors. That means doing a little bit of each.

The key difference here is that unlike the original game, the investing version tends to play the same hand sequentially. Meaning, if Momentum has outperformed last year, the odds are good that Momentum will outperform this year, as well. This may occur until Momentum is so overpriced that it eventually fails. Sometimes, it fails badly.

While you might want to follow one-year trends in factor performance, following 5-year trends can be hazardous to your portfolio. In short, you can run the risk of becoming too predictable for your own good. Spend too much time playing with scissors, and you’ll eventually get crushed by a rock.

So, how do you know which factors to play?

The guys at Oppenheimer Funds put together an actively managed index strategy that allocates between the five basic factors, based on the business cycle. The timing for the business cycle is determined by watching key economic indicators and what they refer to as “global risk appetite.”

Factor Boxes11

And the back-tested results are looking quite good, generating annualized out-performance in the +5% range. Please keep in mind the fact that most new strategies look pretty amazing in hindsight.

Factor Boxes 009

 At the end of 2017, a new ETF was released that follows this active allocation approach. The Oppenheimer Russell 1000 Dynamic Multifactor ETF (ticker: OMFL) is off to a great start. It may be one of the few new ETFs that you can buy, hold, and then forget about for ten years.

Can it be possible that index investing is simple again?

Jim Lee, CFA, CMT, CFP®

Disclosure: Information contained herein is for educational purposes only and is not to be considered a recommendation to buy or sell any security or investment advice. The advisor holds shares of the Oppenheimer Russell 1000 Dynamic Multifactor ETF in client accounts. Securities listed herein are for illustrative purposes only and are not to be considered a recommendation.


The Disruption of Finance

  • Jim Lee
Depositphotos 54085067 l 2015
As a futurist, I spend much of of my time thinking about "what happens next?"  In this article, I'll share an insider's view of the finance industry. Much has changed in the past 25 years, and it's been exciting to watch.
Let's start with the existing trends first, followed by some of the new stuff:
1) Rise in popularity of index investing. There is extreme price compression going on in commoditized asset management. It truly is a race to the bottom. Some index funds now carry annualized fees as low as 0.04%. This is beginning to translate into fee compression for traditional active managers.
This is also translating into so-called "economies of scale" - bigger companies are getting more competitive, in part, because they can charges lower fees.
Meanwhile, conventional mutual funds are bleeding assets, while the bulk of new inflows are going to a handful of Index providers, primarily those offering Exchanged Traded Funds (ETFs).
Index and Ownership
Source:FactSet, P&I and Simfund as of 03/31/2018.
The irony here, is that big fund companies such as Vanguard and Blackrock may be the ultimate beneficiaries from the rise of robo-advisors (which tend to rely heavily on index funds). The top ten asset managers now own roughly 30% of all the companies represented in the S&P 500 index.
2) Because of the dominance of indexing strategies, stock selection is going somewhat out of favor for the general public. Investment management is becoming more about understanding and tracking the exposures that your companies correlate to, and less about the companies themselves. Think about that.
For sophisticated investors, privately managed equity portfolios continue to offer tax efficiency, along with the ability to customize accounts according to individual preferences.
3) Automation disrupted the investment research world a while ago. I run into quite a few former analysts / portfolio managers that were outsourced to algorithms. A regional bank a few blocks away from the StratFI office almost entirely liquidated its staff of analysts back in the mid 2000's.
Just last January, the AI Powered Equity ETF (ticker: AIEQ) was introduced, using IBM's Watson to actively manage stock selection. This will be fascinating to watch.
4) Indexing -> smart indexing -> active management of smart indexing strategies
A few years ago, we saw a boom in smart beta ETFs, which focus on various "factors" (value, momentum, quality, etc.) that appear to provide superior performance characteristics over time. As any expert would tell you, these factors come and go out of favor.
Cropped Multifactor
So, the new, new thing would be strategies that actively switch between those factors. Oppenheimer funds started its own Oppenheimer Russell Dynamic Multifactor ETF (OMFL) and Vanguard is following up with its own multifactor ETF (VFMF).
These strategies blend active management with algorithmic enhancement to traditional indexed strategies. How "meta" is that?
5) The headaches of regulatory oversight are contributing to a decline in the number of publicly-traded companies within the U.S. These figures peaked shortly before the adoption of Regulation FD (2000) and Sarbanes-Oxley (2002).
It is much more appealing to be a privately owned and funded company now, especially with an abundance of venture capital. Easy money, less regulation, what's not to like?
Many companies are waiting much longer before having their IPO, with initial public offerings now more of an exit strategy than a funding mechanism. The result is a narrower set of opportunities for public investors. 
Listed U S Company Count
6) Blockchain technologies pose a competitive threat to traditional financial institutions. Blockchain/crypto-currencies already provide alternatives for funding, trading, and cash transfer. Financial intermediaries run the risk of becoming disintermediated.
Initial Coin Offerings (ICOs), those bizarre love children of crowdfunding and IPOs, have already raised more than $9B this year. While crypto-currencies boomed in a "Wild-West" environment, further adoption will necessitate some further regulatory oversight.
(Trends #6 and #7 highlight the problems of "too much" vs. "too little" regulation, and the complexities of managing change.)
7) When the stock market (eventually) goes into bear mode - index funds are likely to get sold first. It is how flash-crashes happen. Many ETFs are not going to be as liquid as people think, periodically trading at steep discounts to net asset value. This will create a counter-trend opportunity for active managers.
8) The future of advice. You'll want to be sure that your financial advisor can keep up with the times.
The trend seems to be moving towards bigger money managers offering a less personalized experience. Some financial advisors are going into full "robo" mode, while others are more focused on "soft" services such as life coaching. At StratFI, we provide leading-edge investment advice with personal access.
Our offerings continue to evolve rapidly. Feel free to give us a call or send an email if you'd like to learn more.
James H. Lee, CFA, CMT, CFP®
(302) 884-6742
Disclosure: Information contained herein is for educational purposes only and is not to be considered a recommendation to buy or sell any security or investment advice. The advisor may hold shares of OMFL and AIEQ within client accounts. Securities listed herein are for illustrative purposes only and are not to be considered a recommendation.