25 June 2022

The Idea Maze

Philosophical technologists, startup engineering and placing bets on the future

How does one know what to do when there is no map?

What has caught my curiosity recently is how so many of the prominent figures within the technology space come from creative or philosophical backgrounds in addition to, or in substitute of, technical acumen.

  • Joe Gebbia, co-founder of Airbnb — graduated in 2005 from the Rhode Island School of Design with a Bachelor of Fine Arts degree, and designer of the CritBuns
  • Chris Dixon, venture capital partner at a16z ($33B in assets under management) and serial tech entrepreneur — graduated with a BA and MA in philosophy
  • James Dyson, inventor, industrial designer and founding entrepreneur of Dyson — studied furniture and interior design at the Royal College of Art, designer of the Sea Truck and Ballbarrow

This took me by surprise. When I think about what it takes to be a founder of a technology company or an entrepreneurial innovator, my initial conception would be to assume that such a person would have to have a technical background. How else would they discover new insights that others have not seen, if not for their subject matter expertise within the technology itself?

But this is not the only prerequisite in being someone who is capable of effectively navigating the idea maze; if anything, it seems like having a background that is multi-disciplined and divergent to technical only serves to supplement a founder’s character attributes.

A good founder is capable of anticipating which turns lead to treasure and which lead to certain death. A bad founder is just running to the entrance of (say) the “movies/music/filesharing/P2P” maze or the “photosharing” maze without any sense for the history of the industry, the players in the maze, the casualties of the past, and the technologies that are likely to move walls and change assumptions.

- Balaji Srinivasan

To me, many of the prominent figures within technology can even be considered to be more creative than technical. Creative, not necessarily limited to artistic expression like drawing or painting, but creative in the pure sense of the word — to have the capacity of generating something of value from nothing.

Steve Jobs would be an eminent and fitting example of this. More visionary and innovative than technical. From his immortalised 2005 Stanford commencement speech, Jobs shared about a particular chapter from his earliest years in college, of how he had taken the deliberate decision to drop out of courses that did not interest him in order to drop into the courses that did. One particular course was one on calligraphy, seemingly divergent and impractical at the time, but the knowledge he had gained on typography eventually served as fuel for inspiration in the design systems for the Macintosh computer 10 years later.

Jobs was a visionary in the sense that, at least from the outside looking in, it was as if he could see a particular version of the future where the products he made would look and feel a particular way — such nuance on end user experiences, the kinds that play out effortlessly and beautifully, do not come about accidentally. It is a by-product of rough ideas honed to precision and countless of hard decisions made during the making of the things we ultimately get to hold in our hands.

Someone who, to me, would sit on the opposite end of the spectrum to Jobs would be Balaji Srinivasan — someone with the type of bio and track record that makes me question whether time flows at the same velocity for all of us or not. It continues to boggle my mind how it would be humanly possible to accumulate such a range of experiences under ones belt. Here is a snippet from his personal website:


One could look at such a bio and say, ‘Ah, look at all the engineering degrees he has — of course, he is successful in the space of technology!’

But the thing that both confuses and intrigues me is the fact that his transition from being a rigorous academic in Electrical and Chemical Engineering (Dr. Srinivasan) into being a founder of cryptocurrency organisations like Earn.com and Coin Center and technology startups like Counsyl and Teleport is not a linear and predictable trajectory, by any means.

In the context of startups and technology, what comes to your mind when you think of the word ‘technical’?

To me, I instinctively think of the words ‘computer scientist’ or ‘software engineer’, and I would be hard pressed to come up with answers that come anywhere close to electrical or chemical engineering.

Just because someone might have all the technical capabilities of being a competent engineer does not predispose them to being a successful startup founder or investor — the domains are very, very far apart.

How does one even become a startup founder, anyway?

I had recently bumped into some course material from a Stanford MOOC called ‘Startup Engineering’ which Srinivasan had taught back in 2013. The material is basically a starter pack for potential founders intending to start a new technology startup, the how in going from command line to building a web application for early testing of product-market fit.

2013 also stood out to me for a few reasons. In the course, Srinivasan goes through some of the historical lore of the internet, starting from the earliest phases of the internet being freed up for global commerce and closing at the state-of-the-art of that year. Somewhere amongst this, he had mentioned about Bitcoin, which in 2013 was in its earliest and most uncertain days, just a mere 3 years after the infamous news story of 10,000 BTC being spent on 2 pizzas had broke.

Startup Engineering: Introduction slides

I am not sure about you, but in 2013 I was filing into lecture halls with my rose tinted glasses still intact and enthusiastically spending all my time on solving academic puzzles during my first year at university. Although I was spending a lot of time wandering the internet, I definitely was not thinking about cryptography, digital currencies or much else aside from the specific domain of engineering I had chosen to commit myself into — blockchain and cryptocurrency being topics that I had only very recently started to actively try and understand more about.

Tying back to the course material, there was a particular segment where Srinivasan mentions about the use of cryptographic keys that form up the git (2005) and Github (2008) distributed version control systems — relatively ‘old’ technology by 2013. But it also happens to be the case that Bitcoin was built on the promise of having a hard digital currency, on a foundational layer secured by cryptography.

This was a flash-in-the-pan moment for me, because it helped me realise that at a time when the majority of people in the world would not have heard, let alone comprehend, about what Bitcoin was, to people like Srinivasan it would have likely appeared to be just another emergent branch on the technology tree — an evolution and extension of prior technology that had already existed and was working well.

While there is plenty of room for could-have, would-have, should-have self deprecating statements that I could make here, I was simply at the wrong place at the right time. The idea maze mentioned before? I was not even close to even knowing what an idea maze was, let alone being an active participant doing the discovery process of founding startups and investing in new technology.

But it also occurs to me that it is not always obvious what one should do in the face of insights of what the future could look like. It is no trivial task to think deeply about how a technology could survive and what the world might look like once it is able to thrive.

The instinctive mental model that comes to mind is, ‘has this worked well before?’ but this level of questioning gets thrown out the window immediately when in the face of something that is brand new, undeveloped and in its infancy stages. Just like a newborn child, the explicit features might be comparable to how the baby might look like 20 years later as an adult, but the best we can hope to do is to make a reasoned and rational approximation of what the future could look like — hoping to have complete certainty in such scenarios would be impractical.

Eminent technologists fall into two groups (probably oversimplified but it was a conscious decision to trade nuance for expediency in this case):

  • Those who acutely observe the idea maze and place bets on (and provide critical support to) the players who have the greatest likelihood of survival and success
  • Those who face little alternative choice but to pursue their vision of the future, by running and building within the idea maze

These two groups are actually partaking in synergistic bets of what the future might look like, despite their methods appearing very dissimilar.

Back to the original question: how does one figure out what to do when there is no map?

This is where philosophy or creativity plays a part in helping out the logical, rational mind in taking the next necessary steps where there is no clear path to follow. They help form up guiding principles and frameworks to think through and operate within the fog of ambiguity. To operate where there is no such thing as a standard operating procedure.

Within such domains, it is an impossible task to distinguish ‘right’ from ‘wrong’ because there is no such feedback until after a particular course of action has been taken. So what venture capitalists and entrepreneurs have to do is to have the courage and tenacity to continuously place bets through every step they take on their journeys. There is no established protocol or best practices to take comfort in, which is why many are, not surprisingly, voracious learners — multidisciplinary sponges that are constantly seeking out insight, knowledge and understanding through everything that they do. Perhaps more out of necessity than anything else, and perhaps this is what it takes to be as prepared as one can be in the gaps that appear between taking steps.

The feedback for these technologist who place the right bets at the right time is financial upside in addition to having a clearer insight into what the future might look like. When they win, it is almost by necessity that the wins are disproportionate — in order to make up for the financial losses accrued all the way up to that point from all the prior unsuccessful bets, and the emotional pain that must come from enduring such a failure rate — inherent to operating at the frontier of what is possible.

It’s what is the current definition of the frontier. There was a time when it was the wild west, there was a time when it was conquistadors and people setting sail in the age of sail.

Today it feels like the frontiers os on the internet and even on the internet, the frontier is within Web3 and crypto because it’s sort of the least regulated, the most decentralized, the most permissionless, 24x7x365 markets that are self-funding, hackers from all around the world can participate.

Naval Ravikant

For the majority of us who are neither startup founder or venture capitalist (these professions, from a pure statistical perspective, are very rare), it is important to note how decision making, placing bets on potential future states, is something that we all do all of the time. Except it is not as explicit because much of the thinking and decision making processes have been automated and abstracted away by habits and routines so that our minds are freed up to comprehend other more pressing issues. This is invaluable, so that we do not have to question about wastewater treatment processes every time we fill up a kettle to boil water or ask questions like, ‘why do humans wear clothes?’ every morning.

But asking the seemingly simple questions, to take away the layer of abstractions and to poke into the stuff that lies beneath our day-to-day perception of life, can often lead to surprisingly interesting insights.

He said, “Well why do fancy restaurants have white tablecloths? They literally call it a white tablecloth restaurant if it’s fancy. Why?”

I couldn’t really — I came up with dumb answers. “It feels good. It absorbs a spill,” or whatever it may be.

He said, “No, it’s because the table underneath is a piece of shit.”

Nick Kokonas

P.S A practical visualisation of what it must feel like to enter an idea maze