On Counsel
“Let us now speak of the inconveniences of counsel, and of the remedies. The inconveniences that have been noted in calling and using counsel, are three. First, the revealing of affairs, whereby they become less secret. Secondly, the weakening of the authority of princes, as if they were less of themselves. Thirdly, the danger of being unfaithfully counselled, and more for the good of them that counsel than of him that is counselled. For which in conveniences, the doctrine of Italy, the practice of France, in some kings’ times, hath introduced cabinet counsels; a remedy worse than the disease.”
“What do you think I should do with my life?”
I was on the phone yesterday with one of my first mentors, a guy who opened the door and let me into The Game when I was an imprudent young 21 or 22-year-old. I wrote in Blind Spots about pivot points; this is the man who was the O.G. Pivot Point Creator.
Before yesterday, we hadn’t talked in several years. I’d reached out to him before I launched my own fund in 2019 to see if he was interested in investing, to which his response was basically, yes, five years from now, if you’re still around and your returns aren’t trash I’m in. This wasn’t an uncommon response from institutions and ultra-high net worth individuals who have been seeding emerging managers for decades and know that most new funds flame out within two to three years—which is precisely what mine did.
After that initial phone call, our next phone call was a few years later when he saw me in the papers. He only had three words for that part: You fucking idiot.
Now, I finally had him on the phone for a heart-to-heart. It’s funny how your relationship with your early mentors doesn’t really change with age; I’m 38 now instead of 21, but I still feel 21 when it comes to how I address him, kind of like how your parents will always view you as a 12-year-old no matter how famous and successful you become. It’s as if people forever remember us in the form that we were when they first met us.
After catching up for a half hour or so, I absentmindedly asked him the question from before:
What do you think I should do with my life?
Without hesitation, he replied:
“Only you know the answer to that.”
I laughed, because it is 100% the perfect answer to what really is a stupid question. And I’ve been sitting here noodling over those words and reflecting back on all the times in my life where I asked it, and I keep coming back to the same unsolvable riddle:
I can lay out where I come out on that today, the genesis of how I got here, and a guarantee that I will have a different answer for you if you ask me five or ten years from today. Because as I find myself asking over and over these days, hasn’t my judgment has been wrong so many goddamn times in my life that I would be foolish to assume that it’s correct today? Isn’t this why the sages wrote “trust not thyself until the day of thy death?”
I sort of understand now what Montaigne was getting at with his Essays, which is a mistranslation in English. Essays implies some sort of certainty, like, here are my well-researched and confirmed thoughts on a given subject. The French is Essais, which is more like trials, experiments, or attempts. He wasn’t trying to prove anything, but merely pontificating on a wide variety of topics — les Q’s with no A’s — and reaching back to antiquity to lay out not just conflicting opinions on these topics, but to express a condemnatory attitude on how vain and presumptuous we are to think we have all the answers.
And so, while it would be delusional to even view myself as a Temu version of Montaigne, I’m okay with putting stuff out that’s wrong and updating it later. Some posts, like On Forgiveness, On Judgment, On Kindness, I’m confident enough to pound the table and say this is the way. Be kind, you craven beast, you doddering poltroon, I beseech you to be kind! Here, I’m just kind of meandering in hopes that even one paragraph, or one sentence, might jump out at the reader and cause them to say this is helping me organize my own thoughts.
I meant to put something along these lines in On Writing but forgot, due, no doubt, to the fact that I am a doddering poltroon. The point to be made was that I can name plenty of books I’ve read that were 700-800 pages but where I only remember one paragraph, one sentence, one principle that changed my entire life. The rest of the book could have been trash, but as a whole, the book will remain imprinted in my mind as a book that permanently changed my life for the better. And so if you invert that, as a writer, like, your hit rate doesn’t really need to be that high! If you can write in a way that is engaging and entertaining enough to keep them from putting you back on the shelf, you really only need to land one or two knock-out punches for the reader to come away and say damn, that was worth my time. So, stop worrying about perfection and start putting yourself out there, because as I shall continue reminding you, you never know who has a wound in the shape of your words.
Now, the earliest part of my life when I started thinking about the topic of counsel was in therapy. I wrote about this in Blind Spots:
“Plus, you can only ignore biology, genetics, and intergenerational curses for so long. Your parents’ shortcomings are buried deep within you. My attitude on discussing this kind of stuff had always been, well, this is what family and friends are for, right? Aren’t they supposed to be the ones who you go to with problems?
Wrong. There are some topics where the worst advice you’ll get is from family and friends. Not because they’re bad people, but because they’re too close to the situation to give objective advice. The first layer of lipstick is unintentionally colored by their own self-interest, and then the second layer is intentionally colored by what they perceive to be your self-interest: happiness, emotional stability, et cetera, the type of ideals that almost always run counter to how the cold hard truth will make you feel. You need an outside voice with no skin in the game to interrupt you mid-sentence and tell you, YO—stop right there. You are saying some wild shit like it’s normal. None of that is normal. None of it.”
That was my approach for a long time—looking outward, to others, for the truth about myself rather than inward—and it stayed with me when it was time to launch Brattle Street. I distinctly remember a lot of things about entrepreneurship that I had no clue about, having spent the preceding decade in W-2 handcuffs, and I decided that what I would do is go ask the twenty smartest people I know for what THEY would do. If they disagreed, I would take the majority answer and then go with that one. So if out of those twenty people, seven people had the same answer and the other thirteen were all over the place, I’d go with whatever the seven said, because, well, what the fuck do I know? Even one of those twenty has to be better than my own instinct, so, like, seven times one means that this is clearly the path.
Here’s the pros and cons of that. The pros are that this shows humility, because truth be told, none of us know shit. Plus, anyone who trades markets for a living has it engrained in them that the crowd is always right. Even if you’re against the efficient market hypothesis, you really aren’t, because while the market is short-form inefficient, you are making an inherent bet that the inefficiency will resolve itself with time. Otherwise, how do you expect to get paid? The crowd can be wrong today, but they have to be right eventually, else there’s no point in playing the game.
That’s the pros of this approach. The cons are what I tried to sum up here:
The reality is that you cannot rely wholly on other people’s counsel as you make your way through this world, because if you are living life correctly — accelerating, taking risks, constantly pushing yourself outside of your comfort zone — you are going to frequently find yourself navigating your way down the rapids, facing fork after fork, and it’s unrealistic and insecure to think you can keep pausing to ask people around you “hey, like, which way should I go?” Sometimes shit hits the fan, you don’t have the luxury of time on your side and you have to operate off gut instinct. You may be wrong, but the process of being wrong is how one develops a sharp instinct; hence the epigram experience is what you get when you didn’t get what you wanted.
In terms of counsel, one of the biggest regrets I have, by far, was when I was actually running the business. It was April 2020, the depths of a global pandemic crisis or whatever the fuck we are calling it these days, and I was getting chewed up by the market. I was positioned for lower prices, everyone was universally bearish, Buffett was vomiting all his banks and airlines, the barrage of newsflow was nothing but bad…and yet the market kept rallying.
I have been trading long enough to know that this is what bottoms tend to look like, where it isn’t clear why the market is rallying, everyone is calling it a bear market bounce or a short squeeze, and then 3-6 months later you find out that all the leading indicators and the trajectory of earnings growth had already bottomed and the market sniffed it out. My instinct said that even though there was no reason whatsoever to get long, it was time to get long, because the fact that there is absolutely zero reason to get long is exactly why you should get long—especially when the tape has already turned bullish and is relentlessly shrugging off bad news. If you’ve been trading long enough you know exactly what I mean.
Anyway, instead of just making wholesale changes to the book, I wrote up an email a few weeks into April called “bull case” and sent it out to most of my limited partners, just laying out my logic and seeing what they thought. I would say about half didn’t reply and the other half said something along the lines of you have to be nuts to be buying here. This is a logical response, because there was absolutely no reason to buy. But looking back, I can’t believe how foolish I was. Dude: YOU are the fucking expert! YOU are the captain of this ship! All these people invested with you because they trust your judgment to navigate rocky waters! And you know full well that the logical trade is quite often the opposite of the profitable trade, because you've spent years paying the price to learn this lesson in the cost of negative P&L. So why the fuck are you looking to everyone else for counsel?
At the time, I sort of felt like I was being considerate and showing that I didn’t view my judgment as superior to theirs, that we were partners in the truest sense and that I valued and trusted their input as part of my investment process, but today, looking back with a clear head, I think I just was an insecure clown who didn’t have the courage to act on his convictions. I stayed bearish and short in a market that was grinding higher, ignoring my P&L, ignoring my instinct, and it was from that point on that the seeds of my failure were sown as I engrained the habit of going against my gut and making bad decision after bad decision. Once you lose trust in yourself, it’s a wrap. You don’t deserve to win and the L becomes guaranteed. It’s been five years and I’m still furious, if it isn’t obvious; I have a double-edged character trait of dwelling on the past, which at its worst can be counterproductive, and at its best could be referred to as Darius Syndrome.
Mood as fuck.
Today, my sentiment is best summed up as ne te quaesiveris extra, from Emerson’s “Self-Reliance and Other Essays” — loosely translated as do not seek outside yourself. Everything you need is within you, my brother. You have to trust your gut and lean into it, and while it will lead you astray at times, you learn lessons that stick from those mistakes. You don’t learn shit following someone else’s advice, aside from the lesson that you should’ve followed your own gut. Sharp investors know that this is why you don’t trade off other people’s stock tips: you can’t borrow someone else’s conviction, you have to develop it within yourself, and without conviction there is never any real dough to be made, just little-dick money, two-bit piker shit.
The problem with excessively seeking counsel is that like I said before, you are going to run into forks and roadblocks and you can’t keep obsessively reaching out to others for what they would do in a given situation. This is also an opportune place to remind you of some wise words: there are no adults and we are all just winging it. We tend to forget this, but it’s 100% real — some people are just faking it much harder than others. And of course, as Bertrand Russell wrote, the whole problem with the world is that the fools are always so certain of themselves and the wise are so full of doubts.
Now that I’ve gotten my point across, this is where I’ll openly tell you that I have a bias on this issue. I am a raw instinct proselyte, devout supplicant of the gut-feel Caliphate, because I have so many scars from going against my inclinations. The deepest scars are the ones where my gut said one thing, I sought counsel, I followed the counsel against my better judgment and I got smoked as a result of the decision. Making the wrong decision hurts, making the wrong decision AND having gone against your instincts in making that decision will have you feeling like a contemptible worm. Remember the Athenians, indeed.
I still ask people for advice today, because sometimes my gut is silent, but if counsel says left and my gut says right then you can bet your ass I’m going right.
This is where the faux-wise in the crowd will say something like well Greg, sometimes you want to trust your own gut and sometimes you want to trust other people’s advice, because everything in moderation! Moderation, I tell you, moderation! I have never heard this type of shit from world-beaters, boat burners and people who embrace instead of run from risk. Homeboy, sometimes the gun is to your head and your gut says one thing and counsel says another. There is no moderation, my dude. There is no third choice, no middle option. You either go right or you go left, and if you don’t make a choice you get smashed on the goddamn rocks dead-ahead for being an indecisive coward. In the words of the great sage Charles Bukowski:
As for the Q with no A from earlier: “Who knows you best, the people around you or the man in the mirror?” I vote man in the mirror. Bet against that guy at your own peril. And so, next time the heat is on, next time you’re trying to decide whether to look externally for answers or look for them within yourself, I would advise that you default to my mentor’s wisdom:
“Only you know the answer.”
Ne te quaesiveris extra,
GB