STORIES FROM AGRIPPA’S TRILEMMA – Impacting startup founders’ mindsets

In these unprecedented times of (using the word unprecedented) uncertainty, many of us are contemplating taking the leap of faith and becoming full-time entrepreneurs. In this edition of the Zymurgist Diaries, let’s attempt to understand the (delusional) minds of startup founders required to handle the paradoxical chaos around them, and how simple structures such as tetralemma and trilemma, along with other mental models can help founders overcome their fear and anxiety.

Entrepreneurship is bizarre, because, as a startup founder, you have no idea what you are doing; yet, at the same time, know exactly what you are doing.

Prospective founders

Understanding the chaos around startup founders

Startup Founders often get overwhelmed with the three most common scenarios in reasoning. I will attempt to elucidate these points over the next 3 posts of Zymurgist Diaries, and introduce structures to reason with the unknown and the chaotic:

  • When you think of starting a venture – “WHY-THE-HELL-DO-I-WANT-TO-DO-THIS?”
  • Before you start a venture – “WHERE-THE-HELL-DO-I-START?”
  • After you start a venture – “WHAT-THE-HELL-ARE-MY-PRIORITIES?”

So, prospective Founders: without further ado, let’s get started with the epistemological questions before you dive into entrepreneurship.

Startup founders deal with paradoxical situations all the time

The startup life for founders is dangerously open-ended and is always spent on the frontier with everything that they are doing. They are always on the edge of new concepts, new designs, of what’s “normal”, and what’s not normal, of critical success factors that define whether the product will be acceptable, the PMF, selling it, financing it, oh, and creating value for yourself and your team without having the scrape the bottom of the barrel – you get the drift…

Deep down inside – The Paranoia Room

This leads us to the paradoxical situation where you can almost always never plan for what’s to come, yet, you need the plans to somehow make it happen, of course. While things may appear to be calm on the outside, founders tend to have a secret basement deep down inside (a.k.a. the “Paranoia Room”), where fears reside and often make their way up to the seemingly calm exterior on a number of occasions when things get out of control or when new fears manifest.

The Paranoia Room

Exhibiting cocky confidence often is the only way to quell the fears of the Paranoia Room. But there is a very thin line between confidence and over-confidence as seen in the past edition of Zymurgist Diaries. This where it gets interesting and paradoxical at the same time.  

The problem of the criterion

Even before we delve into the specifics of the structures required at the nebulous stage of a startup, let’s attempt to understand the reasons prospective Founders leave their cushy life and dive into entrepreneurship; and whether there is enough reasoning followed before the leap of faith… or is it just impulsive.

Have been guilty of being an impulsive Founder (and investor) on a number of occasions in the past, and after a few months, have almost always regretted my decision to either start (or invest) in a venture. Over the years and over a series of successes and failures, have come to realise that walking the tightrope of sanity with both – utter confidence and paranoia at the same time requires a degree of self-delusional characteristics and an anticipation of the good, the bad, and the ugly.

Preparedness, structured reasoning, connecting the dots, and planning are the Founder’s best friends to thrive in the chaos that is entrepreneurship.

Epistemological questions before you dive into entrepreneurship

Founders, by nature, have two distinct advantages over others.

  • They appear to “know” less of what is false, because they are either blissfully ignorant, or are willing to ignore despite knowing of it – thus leading to innovations and improvements
  • They appear to know more of what is true – and this acts as the fuel to get started

But more often than not, the above two states are not known to prospective Founders, leading them to get into situations that they regret later on. Prospective Founders often end up starting ventures in domains they have absolutely no idea about i.e. a marketing professional joining a FinTech as a founder, or a finance professional joining a MarTech as a founder or even worse – founding a healthy vegan baby-food company, while not practising it themselves.

So, as a prospective Founder, I have come to ask the following questions before diving in anything:

  • “How do I know what I think I know?”;
  • “Do I first understand what I know, and then decide how I know? or vice versa?”

The consideration  of  these two epistemological  questions  has  served  two  different  purposes:

  • questions are  a means  to  reach  suspension  of  judgment –> so I know where this ends
  • raise theoretical  problems that  drive  the  search  for  theoretical  resolution –> so I know where it leads to

Over the years have come to realise that a couple of simple structures can help prospective Founders take decisions at an abstract level before they take the dive, instead of relying on impulse or gut feeling:

  • Agrippa’s Trilemma or the Münchhausen Trilemma
  • The Tetralemma or Nagarjuna’s Catuskoti (one for another blog)

How do these principles apply to Founders? Read on…

But first, Agrippa’s Trilemma

Agrippa’s Trilemma is one of the most ancient philosophical thought experiments.

Agrippa’s Trilemma is also sometimes called Münchausen’s Trilemma, after the legendary Baron Münchausen, who was able to free himself and his horse from a swamp in which they had become mired, by the expedient of pulling himself and his horse up and out by lifting himself by his own hair.

We know that it is practically impossible to do this in real-life, and that is precisely the argument. Like Münchausen, who cannot make progress because he has no solid ground to stand on, any purported justification of all knowledge must fail, because it must start from a position of no knowledge, and therefore cannot make progress.

Agrippa’s Trilemma applied to prospective founders

Agrippa’s Trilemma is a thought experiment that allows you to look at a belief or a question or a situation with 3 distinct possibilities. Juxtaposing this with the question prospective Founders often ask – “WHY-THE-HELL-DO-I-WANT-TO-DO-THIS?” when they think of starting a venture, we get the below possibilities:

The trilemma, then, is the decision among the three equally unsatisfying options.

  1. Unsupported belief (Foundationalism): This attributes the question or situation to a belief without a sufficient reason and hence cannot be questioned further – i.e. it is a brute fact that must be accepted.

This is the trap that a number of prospective Founders fall into, attributing their decision to start a venture based on their gut feeling or foundational belief (similar to the one by Rene Descartes in his famous cotigo ergo sum “I think, therefore I am” meditation)

Some of the beliefs I have heard from prospective Founders on why they want to start their own venture are:

  • I want to start a venture because my gut feel tells me that I am not meant for the corporate world
  • I want to start a venture because I know that whatever I build will be bought
  • I want to start a venture because I know that whatever I build will get funded
  • I want to start a venture because I am founder material, and am resilient
  • I want to start a venture because my friends are starting ventures and I know I can too
  • I want to start a venture because my friends are getting funded and I know I can too
  • I want to start a venture because I want flexibility
  • I want to start a venture because I want to work lesser hours and I know I will
  • I want to start a venture because…

The problem with the above beliefs is that there is no room to ask uncomfortable questions, as the prospective Founder has already made up their mind about starting the venture, despite there being no solid foundation or reasoning. This calls for a facepalm.

Startup founders

2. Circular reasoning (Coherentism): This is a logical circle in the deduction, which is caused by the fact that prospective Founders tend to fall back on statements that have already appeared before as an answer to their action. The explanatory chain ends up in circular reasoning where A happens because of B, and B happens because of A.

Behold the egg, it came from a chicken.

Behold the chicken, it came from an egg.

Some of the beliefs I have heard from prospective founders on why they want to start their own venture are:

  • I want to start a venture because I want to build a product that people will use, because they will use the products I will build, because people are using the products I am building
  • I want to start a venture because I have really good co-founders and they know what they are doing; and they seem to be co-founder material because they know what they are doing
  • I want to start a venture because I want flexibility and work lesser hours, because entrepreneurs can work whenever they want to, because of which entrepreneurship is flexible

This calls for a double facepalm.

Startup founders

3. An infinite regression or chain of justification (Infinitism): which appears because of the necessity to go even further back, but is not practically feasible and does not, therefore, provide a certain foundation. Infinite regress is not considered to be a valid way to prove why prospective Founders would want to dive in.


  • I want to start a venture because I want to be financially independent because I am currently not because I am working to make someone’s dream into a reality because they are buying my time for money because they are funded because they have clients because they are building products which I can build too because…

regresses from one question/answer to the next and so on. There is no final, all-supporting support, just endless, unsupportable support. The actual reason why the prospective Founder wants to start their venture is lost in the infinite regress. This calls for a triple facepalm.

Startup founders

Is Agrippa’s Trilemma inescapable for startup founders?

It is self-evident why none of the above options are good enough if one’s objective is to arrive at certainty. Unfortunately, one cannot peer into the future to see where the venture may end up.

Instead of relying just on the gut feeling As a prospective Founder, one has to weigh in

OK, so, how do I take that leap of faith?

Before taking the first step, ask the basic question – “What is the goal?” –  the “purpose” of your venture. Write it down. Read it. Start over. Do it until you are convinced about what you are about to get into. Then, write a business plan.

Take out some time from your “busy” schedule and spend a few days on a good business plan; it will save you several months of torture and uncertainty down the road.

The Business Plan?

Check more on the structure of the business plan, and on how to take the leap of faith in this post: Stories from the Shift

Parting thoughts till the next blog:

“In all chaos, there is a cosmos, in all disorder a secret order.”

– Carl Jung

Pause, reflect, act.

About the author:

24x Founder, 3x Success, 2x VCExit, 19x Failure, 100x Resilient, 14x Sectors, 6x Continents, $3+ billion deals originated and advised.

Chennakeshav Adya (Keshav) is an eclectic value creator for mid-sized firms and PE/VC funds on Fund-raising, M&A, growth, corporate strategy and deal-making (currently, as co-founder of Adan Corporate). He is a resourceful entrepreneur with 20+ years of global experience in building businesses from a concept and growing global teams from 2 to 200+.

A deca-lingual, multi-talented zymurgist, Keshav is skilled at using the founder’s mentality and thrives in uncertainty and chaos, directing teams through the “Unknown” in the initial 1-2 years of setting up any type of new venture.

As an Entrepreneur Mentor in Residence (EMiR), Keshav is associated with London Business School’s experiential entrepreneurship activities supporting students and alumni who are interested in pursuing a career in entrepreneurship, whether launching or growing their own ventures.

Keshav is reachable at and loves speaking to startup founders and VC fund managers on topics of growth, technology, and the traps of entrepreneurship.

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