Resolving Uncertainty for Founders & GPs

A founder’s job is to convert uncertainty into risk, one milestone at a time. The same applies to emerging fund managers, with DPI as the ultimate uncertainty resolver.

Recently listened to an insightful Origins Podcast episode with Alec Litowitz, founder of Magnetar Capital and previously founding partner of Citadel.

Alec drew a fascinating distinction between “Uncertainty” and “Risk” and explained how people often confuse the two. PS: I can clearly see that this framing has emerged from his extensive experience in public markets.

Risk is something where the possible outcomes and their probabilities are both known eg. what number is likely to come up when you throw a dice. Because the odds are relatively known, risk can be priced.

The other end of the spectrum is where both outcomes and probabilities are unknown – these are Taleb’s Black Swan events like COVID.

In the middle of both is Uncertainty – where outcomes are known but probabilities are unknown. This is where most of life unfolds eg. going on a date, hiring an employee, etc.

Any new early-stage business operates with uncertainty, not risk. And the main job of a founder is to resolve this uncertainty to discover probabilities of possible outcomes of the business that can then be priced.

In other words, a founder’s job is to convert Uncertainty to Risk, which can then be priced and bet big on by capital providers.

Btw, founders do this by following the classic YC/ Lean Startup approach of fast & iterative feedback loops aimed at making something people want. As simple as that.

For founders, this is an important framing for fundraising and managing runway. You should be very clear about the exact derisking milestones that need to be achieved with each capital raise. Also, articulating that to investors during fundraising helps build extra confidence that the capital will be used well.

Also, this is a good behavioral heuristic too that can help reduce the pressure on founders during fundraising. Every investor will have their own threshold of the current level of uncertainty that they are willing to tolerate. So, a “No” should be taken as a reflection of their appetite, rather than a personal reflection on the founder.

Of course, with every incremental unit of de-risking, your business gets closer to meeting this tolerable threshold of uncertainty, which will ultimately reflect in your fundraising conversion rate going up.

Hence, it’s important to survive long enough to be able to demonstrate adequate de-risking such that access to capital and other resources like talent keeps getting easier with time. This is the driver of compounding in progress that we often see with businesses once they have product-market-fit.

For businesses, this uncertainty resolution is an infinite game, an ongoing journey. That’s why various parts of the capital stack exist – angels, VCs, PE, public markets, debt providers, etc. Each has a mandated uncertainty threshold that they like to operate at, and therefore, are likely to become participants in a business only when that threshold is reached. This will also reflect in how they do asset allocation & portfolio construction.

Taking my own context, this concept of resolving uncertainty also applies to emerging managers who are relatively early in their journeys (Funds I-III). GP fundraising is a slow burn, extremely long enterprise sales process. Following this framework of trying to reduce as much uncertainty on multiple fronts related to the Fund can perhaps help sustain multi-year momentum through this grueling process.

Alec mentions that the ultimate uncertainty resolver for a GP is DPI – it converts all the uncertainty into cash. And this is the reason why he pushes all his portfolio GPs to get into DPI as quickly as possible.

Conquering Uncertainty, Dhoni & Vinod Khosla Style

What does Cricket legend MS Dhoni have in common with Silicon Valley legend Vinod Khosla?

Both believe in breaking down ambitious goals into achievable Base Camps. Here’s how you can use this idea to manage uncertainty in your own life.

One of my favorite sportspersons of all-time is former India cricket captain MS Dhoni. Not because he won every title there was to win during an illustrious international career, but because I learnt the importance of “process over results” by observing him. India winning the 2011 Cricket World Cup under Dhoni’s leadership had a major impact on me personally at the time. I ended up gorging everything he had to say about his philosophy & approach to both cricket & life.

Post that milestone win, I started trying my best to adopt Dhoni’s playbook of “showing up every day & doing the small steps well” as one of the core elements of my value system. Here’s a quote of his that captures this idea really well (paraphrasing a bit for clarity):

What if this happens? What if we don’t win the game? What if we don’t get selected?

Worry about the “controllables”. Focus on taking care of them.

If we don’t get the desired results, we’ll improve. We’ll change our plans. We’ll execute better and we will get another chance to prove ourselves.

Thinking about the result never gives you the result. Yes, you may have a target in mind but what’s more important is taking care of the small steps in life. What needs to be done, what I am supposed to do, what extra I can do. That is what will help us achieve the target.

MS Dhoni

Fast forward a few years, as I was building my startup 0-to-1, I found most thinking models I had experientially grasped as an operator & investor till then were completely failing me in this new chapter. I was wading through risk & uncertainty the level of which I had never experienced before. This was causing immense personal stress & I figured that I better search for some sort of a new philosophy that could help me reframe my approach before I tapped out in the first round itself.

This is when I chanced upon this insightful chat between Vinod Khosla and Sam Altman. Vinod is known for not mincing his words. While he spoke on several interesting topics, what really stayed with me was the concept of “Base Camps”. Here’s how Vinod explained it (paraphrasing for clarity):

If you have a large vision, say you are looking to climb Mount Everest, it’s never a straight line. You get to Base Camp, Camp 1, Camp 2, Camp 3 and so on.

The right approach is to be obstinate about the vision (getting to the top of Mount Everest) but be flexible on the tactics as things change. When you zig and zag, when you pivot.

You could easily set up Base Camp at the wrong place (revenue, customers, investors) such that it doesn’t help you get to Everest. Or you could work a little longer, a little harder, and set up Base Camp at a place that helps you eventually get to Everest.

Vinod Khosla

This idea of Base Camps really resonated with me, especially as I then connected it back to Dhoni’s philosophy of breaking down a large goal into small, “controllable” daily steps and focusing on executing them to your best ability.

As a founder, this idea helped me to disconnect from the stress of achieving a far-out goal, the path to which is understandably fuzzy at this stage, and instead divert my energy towards thinking through:

1/ What’s my next Base Camp? And;

2/ What should I be doing today to get to it?

Focusing on large & far-out goals naturally leads to a heightened sense of uncertainty, which triggers fear-related emotions. However, once you break down the goal into a series of Base Camps & focus only on the next one you need to get to, it dramatically brings down uncertainty, making the immediate path less blurry & abstracting a set of daily controllables that one can focus on.

This approach helps bring down overall stress in the system, thus making it easier to start what I call the Progress Flywheel:

©️Soumitra Sharma

The vision (goal) can still be in the back-pocket, easily referenceable for inspiration on an ongoing basis. However, daily execution is only focused on the controllables that can help get to the next Base Camp. That’s it, no more, no less!

This idea can also be applied to other contexts like fitness, learning a new skill or building new relationships at work. Essentially, this is one of the core approaches behind persevering at anything where the goal is long-term, the path is fuzzy, and overall, the endeavor has high perception of uncertainty & risk.

The idea of Base Camps is at the heart of the milestone-based financing mechanism that Silicon Valley has mastered as an approach to deploying risk capital.

I believe this idea is also at the core of “living in the moment”, often cited as the key to happiness (whatever that is!).

Through the highs and lows of life, I have discovered that the best way to decrease daily stress & internal conflict in your life is to focus on a one-two combo comprising of an ultra-long-term “Mission” + the next immediate “Base Camp” on that Mission. Avoid anything in between those two, the intermediate planned future, as that’s where stress lives.

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