Confessions of a FinTech Junkie

I’m broken. Broken with a capital B. The type of broken that can’t be fixed. Humpty Dumpty had it easy compared to my type of broken. I’m FUBAR broken (look it up) and it’s taken me decades to come to terms that there’s nothing I can do about it.

But instead of starting with the conclusion, I’ll do my best to explain what led me to accept my brokenness by sharing how I discovered I was broken in the first place.

Evidence: School

When I was a kid, it was pretty clear to my parents and teachers that I was pretty bright.  On the smart/not-smart scale, I definitely fell on the smart side of the distribution. In fact, in a variety of subjects, the teachers didn’t know what to do with me because I took it upon myself to learn the subjects on my own (I think I consumed the entire 3rd grade math textbook in about a week which frustrated my teacher). But, I wasn’t uniformly good at school. In fact, there were times it was clear to me that our homework assignments were near impossible and I didn’t understand how my friends were able to cruise by with no problems whatsoever.

For instance, in 7th grade History class, over a series of weeks, continent by continent we had to memorize the names of all the countries and their capitals and be able to write them on a blank map when tested. I can’t even describe the painful hours of study I put in only to wake up the day of the test only to have forgotten everything I thought I had learned the night before. Week after week when a blank map was put in front of me and the teacher said “begin”, my heart started to race and on a good day I would write down about half the required information. If it hadn’t been for a deal I cut with the teacher to do extra-credit work I would have failed the class. Instead, I pulled out a “B”.

Memorizing lists of vocabulary words in 9th grade English – the same.

3 years of French class – even worse. In fact, I wanted to die every time I walked into French class for fear of being called upon to go to the board and show my ineptitude in front of all my friends.

But Math was different. I completed 3 years of calculus and linear algebra before graduating high school and ended up helping the advanced math teacher teach the other students.

And 11th and 12th grade English was also different. We read books and wrote papers and I found myself writing papers at such an advanced level that one of my teachers accused me of plagiarism which turned into a big stink with my dad (he was an English teacher that put 33 years into the school system and turned me into a reader). He backed me of course and chastised the teacher for not doing her job. Yay dad!

Why the differences? At the time I didn’t understand but now it all makes sense.

Evidence: Directions

Anyone who knows me quickly learns that everywhere I go I’m completely lost. And by lost, I mean LOST. Like most teenagers, I went shopping at the local mall, but what amazed my friends was that I’d get very confused when I walked out of a store. I didn’t know which direction we had come from or where the next store that we wanted to go to was in the mall. And it’s not like we only went there occasionally. I worked there for a while selling pianos, keyboards and organs.

I also only knew one way to get from my house to the high school. I only knew one way to get from my house to my best friend’s house. And I couldn’t figure out how to get from the school to my best friend’s house without going back to my house and using it as a starting point. My best friend called me Monopoly Boy because I had to “pass Go” in order to get anywhere. I couldn’t connect the dots.

Evidence: College

Even with all the typical distractions of college somehow I never lost my thirst for reading. In fact, there was a period where I’m pretty certain I read a book every other day for the entire school year (which was possible because I only slept 4 hours a night). My choice in books was always topic driven, and there was one period in particular that I just couldn’t get enough of the beat writers. The beat writers led me from the 50s into the 60s and naturally I found myself reading books about or by Timothy Leary, The Merry Pranksters, Neal Cassidy, Alan Watts and Ken Kesey among others. They described their drug fueled lives and escapades in many ways, but I recall reading a description that stuck with me because it made no sense. Ken Kesey said that he was happiest when he was “living in a waking dream”. And given the amazing things he saw and places he went and experiences he had I couldn’t help but fixate on his description of pure joy. I thought about those five words a lot because it occurred to me that I couldn’t recall the last time I remembered a dream. I knew what dreams were, but I couldn’t recall one. None. This realization actually shattered me and made me want to do something about it.

Broken is Broken

The above stories might be amusing to you (especially those of you who know me well) but they made my childhood difficult. I can truly say that I obsessed over my situation until I finally figured out what was wrong with me. The epiphany came late in my college career with the help of one of my Professors (an AI teacher) who pointed me in the right direction and helped me come to grips with what I discovered. What I figured out was that I definitively have a condition called aphantasia (it was only named recently which made my research tricky). Simply put, if you have aphantasia you don’t possess a functioning mind’s eye and cannot voluntarily visualize imagery. It’s been around and described in psychological texts and journals for quite some time (it was first described by Francis Galton in 1880) but it’s been mostly ignored for the past 100+ years until Professor Adam Zeman renewed interest in the topic with a series of scientific studies that are still ongoing today. In 2005, Professor Adam Zeman developed a test that he named the Vividness of Visual Imagery Questionnaire (VVIQ) which has since become the most commonly used evaluation tool regarding a person’s quality of mental imagery. The questionnaire invites the test taker to visualize a series of images and rank how vivid the images are, from “Perfectly clear and lively as real seeing” (5 points) to “No image at all, you only know that you are thinking of the object” (1 point). A person is categorized as having aphantasia if they total 30 or fewer points after being asked 16 questions. I’ve taken the test twice and scored precisely 16 each time. Basically, I’m visual-memory blind as a bat.

And to make matters worse, while some people with aphantasia can “see” involuntary imagery in their mind’s eye (i.e. – dreams), I can’t. I don’t recall ever having a dream in my life, so I’m dream blind as well. Joy to the world!

It explains my schoolhood failures because they all required visualization skills that I didn’t possess. When I close my eyes I see blackness. The big nothing. But for most people memorization is a visual act. And recall is highly visual as well so even when I jammed something into my memory, getting it out wasn’t a trivial act. I don’t have a map in my head. I can’t close my eyes and just “see” or “replay” something from my past. And I can’t count sheep to go to sleep unless they’re black sheep covered in ink swimming in oil in the middle of the night with no stars in the sky.

So why am I telling this story about myself and how does it relate to building businesses? I’m telling my personal story because I don’t think most Investors realize that sometimes there are aspects of people that are broken and can’t be fixed. I can’t tell you how many times I was told “study harder” or “you’re not paying attention”. And I did study harder and I did pay attention more and it didn’t make a difference.

Many of the Founders we invest in are highly functioning broken people (I’m one) and the last thing we should do as investors is insist on some form of “try harder”. Instead, we should focus on figuring out their strengths and surrounding them with people who can expertly fill in their gaps. If a Founder is brilliant on certain dimensions but falls short on others, the first thing that you as a coach and mentor need to determine is whether or not the Founder has the ability to fix his or her shortcomings. I’m of the personal belief that it’s OK for the answer to be “no”. It might be possible to help them improve a little or a lot, but there are times when there is a true inability to change. And in these cases, the worst thing to do is to insist on change that won’t manifest no matter the effort. There’s no reason to declare the Founder incompetent without finding other people who can be complementary and create a collective win.

It’s also critical to realize that when you give feedback to a Founder all you’re trying to do is turn them into you. You project yourself into their shoes and through feedback outline what you would have done if you had been faced with the situations that they had encountered in the past. But you aren’t them and they aren’t you. And if they’re fundamentally broken on a dimension then your feedback might be inactionable. Don’t try to turn them into you. Instead, help them become the best version of themselves that they can be. But doing this requires putting in the time and effort needed to build a strong relationship grounded in trust. It requires being empathic to others’ shortcomings. And above all it requires believing that it will all be worth it in the end.

I’m a highly functioning broken person because I have GPS in my car and on my phone. For what it’s worth, I’d make a lousy tour guide and an even worse crime scene witness. But fortunately I have people around me who understand my short comings and aren’t asking me to change. I’m broken but haven’t lost sight of the fact that things have worked out just fine for me (even though dreaming sounds fun……)