đ Why we prefer to play moneyball
Hi there,
John here this week! I just got back from the Northwest, where I visited family and took a break from Austinâs summer heat. Whenever I visit my childhood home, I go through my old stuff thatâs been around for over 20 years. This time my walk down memory lane led me to my old baseball card collection from the 80s and 90s. One of the cards I ran across was the 1990 Score Jose Canseco All Star card. Finding my Canseco card made me reflect on how baseballâand investingâhas evolved over time. So today, Iâd like to use baseball and Jose Canseco to illustrate our approach to building client portfolios here at Secfi Wealth.
⟠Moneyball

Moneyball: The Art of Winning an Unfair Game, the book written by Michael Lewis and later made into a movie starring Brad Pitt, tells the story of how Major League Baseball manager Billy Beane used rigorous statistics to build a winning team on a limited budget. The Oakland Aâs approach was so successful that itâs now standard across sports.
A similar revolution has been happening in parts of the investment world. Some of my former quantitative finance professors have even made a second career in sports analytics by applying similar techniques from investing research to athletics.
đ The connection to investing
In investing, the âMoneyballâ approach goes by many names: quantitative, systematic, factor, and smart beta, just to name a few. The essential idea is that certain stock characteristics can provide insights into future expected returns. Additionally, stocks with similar characteristics or âfactorsâ tend to behave similarly to each other and differently from stocks with different characteristics.
Think of it this way, what are the characteristics, or factors of a baseball team that boost their chances of winning? At the most basic level, itâs the ability to score runs and prevent runs from being scored against you. Hitting, pitching, defense, base running, coaching, etc. all play roles in the teamâs success, or lack thereof. In factor investing, researchers analyze data to find the stock characteristics that reliably impact a portfolioâs return and variability (i.e. the chances of winning). Many factors have been documented by researchers. Well studied factors include relative value, quality, momentum, size, trend, volatility, and company profitability. Portfolio managers look to build portfolios informed by these factors for their clients in an attempt to outperform and/or manage risks better.
At Secfi Wealth, we build portfolios for our clients with exposure to factors we believe will outperform over the long run, while seeking to mitigate risks for our tech-employed and equity-compensated clients.
đ Your portfolio
Going back to the baseball analogy, hitting home runs is generally a good thing in baseball. But sometimes players who hit lots of home runs strike out a lot too. Theyâre âswinging for the fencesâ. Jose Canseco was a player who swung for the fences. He hit 452 career home runs but also is among the top ten players for most strikeouts. If you were building a baseball team, would you want nine players like Jose Canseco on the field? Probably not! You might hit a lot of home runs, but your season would be extremely volatile and youâd probably lose more often than you win.
To extend the metaphor, employer stock options in your portfolio are like having Jose Canseco on your baseball team. A great player who can really knock it out of the park, but thereâs a real risk that he strikes out completely as well. What should the rest of your team look like if you have Jose Canseco? Different from Jose! To increase the odds of a winning season, you need to round out the skills of your team to fill the missing gaps.
To increase the odds of investing success, I believe people with concentrated wealth in their company stock should emphasize complementary factors in the rest of their portfolio. The market environment in which itâs easier to hit a home run with your concentrated stock is an environment where other stocks with similar characteristics (factor exposure) are probably doing well. If the rest of your portfolio favors these types of companies, you may be loading up on metaphorical Jose Cansecos, which will be awesome if they hit a bunch of home runs, but devastating if they strike out. In an environment where itâs more difficult for your private company to exit successfully (i.e. strikeout), itâs also likely that public companies with similar characteristics are suffering too. For example, 2022 was a terrible year for public tech stocks, and an awful year for VC backed startups. Rather than loading up on the same factors, we believe itâs better to build a portfolio thatâs complementary to the home run hitting potential you have with your private stock. The highs may not be as high, but the lows wonât be as low either, and on average, we believe youâll come out ahead.
At Secfi Wealth, we often see initial portfolios that are heavy on stocks that share a similar profile to the potential clientâs employer. Thatâs understandable, people like to invest in what they know, but I believe thereâs a better way to put the odds in your favor. And with the prospect of retirement becoming seemingly more and more challenging these days, we can all use every edge we can get.
Interested in seeing if our advisory and wealth management services are a good fit for you? Schedule an introductory call with our team here.
Things weâre digging:
- đŻ Polls havenât been very reliable the last several years, prediction markets might be better.
- đ 31 years ago, a fly ball bounced off Jose Cansecoâs head and cleared the wall for a home run.
- đ Cocaine sharks? Thatâs not good.