The Always Invert newsletter and community launches with an overview of our partnership philosophy and technology wishlists.
The song “Always Look On the Bright Side of Life” was written by Eric Idle, who is best known for his work in the comedy troupe Monty Python. In his recent memoir A Sortabiography, he describes the development of the song, beginning with its roots ten years previously when he taught himself jazz guitar while bedridden with mono. The song’s origin story included his writing it in less than an hour, interrupted by his driving to nursery school in order to pick up his three year old son, who very much appreciated the whistling chorus.
“Always…” went on to further success and cult status as a stadium anthem sung by fans who found their sides losing helplessly. It also eventually became, in January 2009, “the number one most requested song at British funerals, replacing Frank Sinatra’s ‘My Way’”, and has remained there ever since. As Idle points out, who but the Brits “would even have such a chart?”
Eric Idle has always surrounded himself with amazingly talented people. In addition to the Pythons, he was one of the original repeat guest hosts of Saturday Night Live, and close friends with George Harrison, Robin Williams, and Billy Connolly.
While he jokes about his ability to name drop with them best of them, his autobiography is full of stories about amazing adventures and creative partnerships.
He considers Spamalot to be his greatest professional achievement, which makes it all the more noteworthy when he credits much of the show’s success to the direction of the great Mike Nichols. Idle describes the rush for tickets following its Broadway debut:
…By 2:00 p.m. We’d passed the million-dollar mark in a single day, and by the evening show we were already over two million and making Broadway history. So not just a great show, not just great reviews; great box office too. We had pulled it off. The grand slam.
Did I learn anything? Certainly. First, Mike’s Law: Only work with the best. Second, Mike’s Second Law: Never give up. Third: Always work with Mike.
We’ve all worked with someone like that. We all have our own Mike Nichols. Maybe some of us are even at that level ourselves. Wouldn’t it be great to make it that much easier to work together? What would that take?
How can we reverse engineer for that outcome?
Let’s begin with the end in mind.
In 1986, Charlie Munger gave a speech at Harvard in which he described the power of inversion. Munger cited a previous commencement address in which Johnny Carson stated that he couldn’t provide a prescription for happiness, but “he could tell them from personal experience how to guarantee misery”:
What Carson did was to approach the study of how to create X by turning the question backward, that is, by studying how to create non-X. The great algebraist, Jacobi, had exactly the same approach as Carson and was known for his constant repetition of one phrase: “Invert, always invert.” It is in the nature of things, as Jacobi knew, that many hard problems are best solved only when they are addressed backward.
When I was a kid, the Sunday comics page always had a maze. The fastest way to solve it was to work backwards—but that was considered a shortcut. Life doesn’t penalize that approach—it’s okay to walk backwards from endings you hope to create.
Either way, it’s still the same route. The advantage is seeing our paths from a more informed angle.
The Always Invert newsletter and community launches today with the idea to consistently apply these principles of reverse engineering in order to achieve successful outcomes.
Just to be clear, our focus won’t be confined to business and investing. Those can be limiting laboratories, and some of the best work is done when we are simply having fun. There is life to be lived, and not nearly enough time to live it. Which brings us to another mission—how to choose our projects and appreciate these journeys for all their power.
The writer John McPhee had an interesting insight about what governed his writing choices. He posed the question:
“…ideas are everywhere. They just go by in a ceaseless stream. Since you may take a month, or ten months, or several years to turn one idea into a piece of writing, what governs the choice?”
“I once made a list of all the pieces I had written in maybe twenty or thirty years, and then put a check mark beside each one whose subject related to things I had been interested in before I went to college. I checked off more than ninety per cent.”
Most of our new interests turn out to simply be variations on what grabbed our attention long ago. None of us can escape our original interests. What we found compelling as we exited our teenage years will keep drawing us back.
With that in mind, let’s have some fun with that. If we are going to create a community, let’s not limit it to (yawn) “professionally adjacent” projects and workloads. Let’s enjoy being beginners again. When was the last time you did something for the first time?
Let’s learn to surf—even if you are from the landlocked midwest. Break out that guitar—there must be better ways of learning now than when you were ten. Become a DJ. Start creating—your photos, drawings, writings and videos are a source for adventure and sharing. Learn a language—no matter how old you are and what has been drummed into your head about your diminished capacity to acquire foreign languages as you age.
Because at least to that last one, we’ve been misled. There have been tremendous developments in the field of neural plasticity, and what they’ve learned is that we never lose that ability to quickly acquire knowledge and skills. It just requires a shift in how people have traditionally approached these quests.
Who knows? Maybe by having fun in these projects, we can learn about learning. It might even help us in those professionally adjacent areas that we sometimes feel should dominate our hobbies and interests. Wouldn’t it be great to get there, but without the accompanying creative fatigue that comes with everything feeling like it is about work?
Come for the investing, stay for the surfing. Acquire a bunch of new friends along the way.
Investing is one of the most extraordinary of the creative arts.
The investing process can be messy in the same way that anything challenging can be jumbled and chaotic. We completely understand that a painter needs four hours in front of the canvas and tubes to get one good hour of painting done. That there needs to be preparation and organization of materials and settling in and seeing that has to happen.
I believe that all investors can benefit from seeing better. This begins with knowing what they own and why they own it. It includes understanding what opportunities or dangers they might be missing. Organizing that knowledge and accumulating those insights can become overwhelming and challenging once you move past three stocks and a single brokerage account.
Over the last three decades, I built tools and developed insights that led me to successful investment outcomes. Central to this journey was building the tools that helped me see better. Some of these were built from scratch, but many of these were simply utilizing or adapting what had come before and were widely available.
I found that my ability to create and shape these tools had a direct correlation to excellent investors wanting to work with me. Reverse engineering from that simple observation suggests an obvious path: to work with the best, help create the tools and environments that encourages them to share their best questions.
One of the best investors I know—with the track record to prove it—is fond of recalling an unlikely investment recommendation, one that began not so as a recommendation, but as a tell, the clear sign of what we should have all seen. That tell came in an essay by Paul Graham, the founder of Y Combinator, when he wrote in Return of the Mac that “All the best hackers I know are gradually switching to Macs. My friend Robert said that his whole research group at MIT recently bought themselves Powerbooks…”
That was in March, 2005. You could have bought Apple stock then and would never have had to make another investment decision again for the rest of your life. Of course, one could argue that it took a lot to interpret that particular statement and see the investment possibilities. Maybe, maybe not. In the same essay, Paul went on to write about how in 1986 he suggested his father invest in Sun after they built an affordable serious UNIX machine. The principles are clear:
So what, the business world may say. Who cares if hackers like Apple again? How big is the hacker market, after all?
Quite small, but important out of proportion to its size. When it comes to computers, what hackers are doing now, everyone will be doing in ten years. Almost all technology, from Unix to bitmapped displays to the Web, became popular first within CS departments and research labs, and gradually spread to the rest of the world…
…If you want to know what ordinary people will be doing with computers in ten years, just walk around the CS department at a good university. Whatever they're doing, you'll be doing.
If one of the keys to investing is finding insights that seem small, but prove to be important out of proportion to their size, it would be helpful to find easier ways to pay attention. There are tools for that.
We are also going to need to translate these insights and find a way of measuring to what extent they are understood by the marketplace—whether it is an opportunity for us to launch a new endeavor or represents a window for us to participate as investors.
It’s time to discuss the professionally adjacent topics that have drawn me here. I have been contemplating spending a lot of time and resources in order to launch a complete rebuild and rewrite of the investing and trading tools that I have accumulated over the last two decades. I just wasn’t sure where to begin.
I also started to imagine what this might look like if it were to be fun.
Could I build something that I could share with my friends? What is on their wish list? How could we assemble and organize a collection of resources that would naturally attract excellent partners?
Such a platform has always been on my wish list. Beginning with the outcome in mind, how do we build it in a way that helps us be attractive partners? What can we bring to the table?
If we build it right, it could encourage some extraordinary combinations.
Thus, today’s first step—build a collaboration platform and community. Experiment with its form factors and integration of people and perspectives and tools. Use what we learn from these first steps to then construct and share additional collaboration tools.
That is also why we have to include the various progression projects. It’s going to teach us how to learn together. If you are in the Great Lakes region, we can start now—it’s January, the waves are good. Bring your quarantine beard:
Or we can meet in Costa Rica in 2022.
In the meantime, assuming I’m not going to get a lot of takers for winter surfing, I plan to continue reaching out to my friends and partners in a quest to gain insights into what they consider to be the ideal tech stacks for investing, collaborating, researching, and managing workflows. These are the essential building blocks in analyzing investments and managing portfolios. These conversations with investors and traders quickly invert and prompt questions in turn: What do you use? Are you getting your money’s worth? Have you heard about other things we should try?
If you want to take part in this broad survey, feel free to click on my calendly link in the community to schedule a conversation. I will send you a list of questions and topics and we can go from there.
One of my first instincts, having invested in over fifty early-stage businesses and ventures, is to apply what I have learned as an investor and immediately begin building something in my own domain expertise—which centers around these very tools, processes, and insights.
That seemed like an obvious course. However, first instincts can sometimes be worst instincts, especially when it skips the step of listening closely to others.
Instead, I plan to proceed along two parallel paths.
The first path is to do multiple deep dives into the best solutions and practices that are currently available. Sometimes the answer is right in front of us. In these explorations, I hope to simply be the tour guide as we experiment with a wide range of tools and software. My perspective there is to understand what these tools are good at, and meeting them at their strengths, work forward from there to see how they might fit our needs.
The second path is to work backwards from what I really want and wish I had today. In particular, I’m very interested in how we could bridge various tech stacks that would allow for a better way to collaborate on investment research and portfolio management.
My guess, heading into this mess, is that what we need is pretty much out there and simply requires a whole lot of massaging it to do what we want. The advent of no-code and low-code software, combined with the power of integrations now that so many parts of the tech stack have learned to play nicely with each other, has opened up a world of possibilities.
We’re going to be playing a lot in the No Code sandbox. In fact, I just got started with the On Deck No Code fellowship this week. I’ll be sharing lots of insights about No Code in a dedicated community channel. Including how I assembled this publication and community tech stack.
While we mutually solve for these problems, if you see a chance to jump in with some knowledge and insights, please join the conversation. No suggestion will go unread. It doesn’t matter where you are coming from. We all have to start somewhere.
This is where I’m starting—here is my current wish list:
That’s quite a feature set.
Building all of this is going to involve working several simultaneous threads:
That last bit is key—we aren’t trying to build tools alone in some corner of the universe. We are facing a dynamic problem set whose variables are shifting every day, and it takes a lot just to keep up with it all. Solving for this—dealing with the daily opportunities and risk that arise—that’s what makes this work so interesting.
If you want to be along for the ride, welcome aboard. We sure can use you. We hope that you will speak up when you see us miss something that is important. We can always use more sounding boards. You probably do too, so feel free to bring a friend.
In fact, investing is one of the best business endeavors where one can work with a friend, without both of you quitting your day jobs, and come out the better for it.
Let’s build this together.