I was speaking with a big-time investor today. I have had about three hours of conversation so far. He certainly operates at a higher level and is in a very different class than I am (I don’t mean when it comes to generally what depth of a person he is – authenticity or generosity or decency). I am talking about the folks he knows, the deals he has done, the net worth he has accumulated, the risks he has taken, and the knowledge he has under his belt is just clearly a few levels above me. He is older than I, and has been at it longer and excelled in it. How does a person of my intelligence and experience level suss out whether this man is all he is cracked up to be? Can he be enormously helpful to me as a mentor, or am I just a fish he has on the hook? In the human mind, prejudices and cognitive biases abound, so wisdom is really what is called for. In the field of applied philosophy, a thing called heuristics can help, but they can also fail.
As an aside, it’s interesting to me to consider the following: Because a Southern, Christian man with a background in the military is wealthy, does that make him inauthentic? It’s probably where a rule of thumb breaks down. I suppose it’s a type of prejudice on my part. Getting to know him, hearing about how his mentorship can make me incredibly wealthy, and perceiving his statuses (Christian and semi-evangelical, male, white, military background, Southern, wealthy and presumably politicall conservative), it adds up to the blinking red neon sign: “POSSIBLE DANGER”. I ask myself if he is authentic, or if the intuition that has developed in me over time is correct. It can’t be both. So it is a live, high-stakes question about capital-T truth.
If I had to use a strange metaphor, it would be that of having a “bullshit detector.” Everyone does. We hear it ping when a Jehovah’s Witness comes to the door, when we read of a polygamist getting in trouble for trying to have ten wives (and looking for another 15-year-old to include in his collection), when a used car salesman gives us a pitch, when a Realtor opens their mouth, or hopefully when you see Joel Osteen‘s smiling face on television. Many folks also feel that way when they hear Elizabeth Warren talk, Bill Clinton speak, Jamie Dimon appears on television, or Oprah Winfrey is offering her unique brand of self-help. Tony Robbins definitely is in that category, and most politicians are. Your grandma? Not so much. The soccer mom who is walking Girl Scouts around selling cookies? No. Pastors in churches around country? Only sometimes.
In this age, politicians are not trusted, Catholic priests are not revered, bankers are suspect, and you might not even be able to stand your own cousin. It’s a weird time. As I note in this post, the very idea of Truth is in question. It’s scary. Wisdom is a rare thing, but it’s our best hope.
I’m a liberal. I’m agnostic at best. I’m from Southern California. I’m 45. Jewish in culture, but only somewhat. From a dysfunctional home. Smart but my intuition is only so-so. I’m not wealthy in that “born a privileged guy who knows all right people” way. I’m not what one would call a “good, old boy” in either the smarmy Southern sense, or the high-society sense. Knowing thyself is important.
Adam Grant writes this, and it does give me pause. It’s fair to be explicit about this:
“We are in the Age of Authenticity, where be yourself is the defining advice in life, love and career. Authenticity means erasing the gap between what you firmly believe inside and what you reveal to the outside world. As Brené Brown, a research professor at the University of Houston, defines it, authenticity is ‘the choice to let our true selves be seen.’
We want to live authentic lives, marry authentic partners, work for an authentic boss, vote for an authentic president. In university commencement speeches, Be true to yourself is one of the most common themes (behind Expand your horizons, and just ahead of Never give up).
‘I certainly had no idea that being your authentic self could get you as rich as I have become,’ Oprah Winfrey said jokingly a few years ago. ‘If I’d known that, I’d have tried it a lot earlier.’”
I think the questions then are: Who is authentic? How do we know? When do appearances deceive? To what degree are we vulnerable to others’ preferred outward image? How do people take advantage of others, and for what purpose? Is one’s “smell test” they apply to others fully legitimate, or based more on prejudice and mere rules of thumb? How can wisdom help? What is the area of philosophy called heuristics?
This is the realm of critical thinking, of faith vs. reason, of trust vs. mistrust, and can be frightening. Think about The Mask of Sanity, a seminal work by Hervey Cleckley. In that classic text, he basically pioneered the way we think about sociopaths. One look at the edgy and enthralling series Mindhunter will show that this is the place where folks can be taken advantage of in a big way. Sociopaths are at the helm of many Fortune 500 companies, and are disproportionately represented as lawyers and cops. These show that although the worst that would probably happen to me is that a person who is actually a shyster might relieve me of some of my wealth, when women trusted the amiable and handsome man Ted Bundy back in the 1970s, it cost them their lives. This doesn’t leave much room for error when we encounter folks who are inauthentic in the extreme.
Humans are primed evolutionarily speaking to both want to belong, be approved of, and to fear the unknown. That is why I am asking myself if the individual I am considering spending tens of thousands of dollars to engage as a mentor is the real deal. My intuition is telling me both yes and no. The crux is me asking myself about whether if it looks like a duck, walks like a duck, and quacks like a duck if it’s a duck. Or, alternatively, if I am being somewhat paranoid. Abraham Maslow noted that “If your only tool is a hammer, you tend to see every problem as a nail.” That is a subtle and only-semi-apt way of describing that perhaps one or two out of ten folks who have this person’s “profile” are inauthentic folks who must be avoided, and yet my love of my “a hammer” makes me feel like it might be more like 7 out of 10.
Perhaps personal growth involves transcending one’s prejudices and immature notions. I have been told by more than one person, including a very well-regarded psychotherapist and personality expert that I “have trust issues.” After all, my father spent most of his life when I was growing up trying to keep up appearances of being the semi-wealthy, good-looking, funny, affable doctor, and my mom in a similar vein. Yet, they fought, and he was a psychotropic medication addict and she became a full-fledged alcoholic. This is tough for a 14- and 15-year-old to deal with. I also was raised Jewish in a majority-Christian country, but not really deeply involved with the community: kind of an outsider amongst outsiders. There is no way my sister and I could have escaped a deep and complex effect on our personalities having grown up under those conditions.
When folks say “listen to your gut”, you have to be careful because sometimes your gut betrays you. Sometimes it’s a rule of thumb that errs on the side of caution, and fear then guides you to a degree you really don’t truly benefit from. George W. Bush was famous for listening to his gut, and that didn’t turn out well for us as a country. At least, if you weren’t one of his wealthy “Pathfinders“.
“There’s a sucker born every minute”, as P.T. Barnum said, but folks like me have a deep fear of being that sucker. “If you’re at a poker table and you don’t see a sucker, it’s you” (probably “Amarillo Slim”, a famous poker player from the 1980s). That has a certain ring to it, but one thing is true: rules of thumb work in some situations, but not in all.
I think some of this is healthy. Jews have built a reputation (deserved, or illusory) for being “good in business”. I think part of that is the fact that they tend to be “on the lookout” for being taken advantage of, of deals that are “too good to be true” and worry (perhaps too much) of making a mistake. Jews who work in the place where money is put on the line in investments cover their bases, hone their ability to spot bullshit, and think very critically. I think this cultural attribute (stereotype?) is functional and serves Jews well. It can keep one awake at night, cause missed opportunities, and create a slight sense of xenophobia, though. Japanese businessmen, too, have ways of sensing danger that may be very well-honed but neurotic and prejudicial. The fact is that there are always folks who will present themselves in the business world who will happily relieve you of your money if you permit it. Sometimes it is a good investment, sometimes it is a scam, and often falls in-between. “A fool and his money will soon part ways” it is said.
Human beings love rules of thumb; they are a heuristic (cumulatively in the category of heuristics), which make life easier because we are bombarded by stimuli and it can seem overwhelming. As Stephen Hale notes, heuristics often fail.
Here is his take from a very readable article (linked above):
“We make decisions and judgments every day – if we can trust someone, if we should do something (or not), which route to take, how to respond to someone’s question, the list is endless. If we carefully considered and analysed every possible outcome of these decisions and judgments, we would never get anything done! Thankfully, our mind makes things easier for us by using efficient thinking strategies known as heuristics. A heuristic is a mental shortcut that helps us make decisions and judgments quickly without having to spend a lot of time researching and analysing information.
Heuristics play important roles in both problem-solving and decision-making. When we are trying to solve a problem or make a decision, we often turn to these mental shortcuts when we need a quick solution. For example, when walking down the street, you see a workman hauling up a pallet of bricks on a pulley. Without a break in stride, you would likely choose to walk around that area instead of directly underneath the bricks. Your intuition would tell you that walking under the bricks could be dangerous, so you make a snap judgment to walk around the danger zone. You would probably not stop and assess the entire situation or calculate the probability of the bricks falling on you or your chances of survival if that happened. You would use a heuristic to make the decision quickly and without using much mental effort.
However, while heuristics can speed up our problem and decision-making process, they can introduce errors and biased judgments. Just because something has worked in the past does not mean that it will work again, and relying on an existing heuristic can make it difficult to see alternative solutions or come up with new ideas.”
Learn More From An Excellent Source for Ferreting Out How Heuristics Go Wrong (what is called “cognitive biases”) HERE (skip to the middle, past the fluff)
In sum, I’m afraid I have a dense and complicated paragraph, so I apologize. But here it is:
1) Either the gentleman I began this article writing about is a person to be avoided (a smart move on my part), or I need to analyze the functionality and validity of the heuristic that Southern, Christian, white men who say they are very wealthy and can teach me how to be if I pay him are to be avoided. This heuristic, made possible by the con men and the televangelists and the cult leaders and the politicians and the CEOs out in the world (as well as my difficult childhood), is either prejudicial and cognitively-biased information that will cost me hundreds of thousands in lost potential financial gains over the next few years, or being wary and not working with this person is the right decision and will save me from spending tens of thousands of dollars. He is either offering a rare opportunity to play in the big leagues with a coach who has won repeatedly and learned from his mistakes, or it is really a sales pitch from a man who makes a lot of money convincing the uninitiated to willingly part with their money but to no benefit to them. His status as a guy who kind of fits the mold in my head for folks to be wary of is either a coincidence, or it is my gut telling me to beware. Thus, it is wisdom we’re talking about, here. Ω
Keywords: heuristics, cognitive biases, critical thinking, philosophy and critical thinking, blogs about critical thinking, blogs about applied psychology, blogs about applied philosophy, real estate investing, investing wisdom