People always ask me about my transition from investing to operating and I think I found the perfect summation:
Investing is a well-defined, deterministic problem space.
Operating is a poorly-defined, nondeterministic problem space.
Here's my reasoning...
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As an investor your job is to generate returns. Some investors choose to be hands on to help startups create value while others are more laissez faire. Either way it all boils down to ROI.
The decision making process demands an investor to research and analyze team backgrounds, market opportunity, technical/product diligence, risks, and corp/gov structure to come to a single, boolean decision - to invest or not to invest.
Investment decisions are typically grounded in probabilistic distributions of outcomes, often referred to as expected value (EV). For a professional investor, this decision making process can be trivially systematized to account for sizing and portfolio construction (ex. Kelly Criterion). This means most investment decisions can be run in parallel without dependencies given a proper investment strategy.
In theory the same inputs to your decision making process should always result in the same output.
*This is also a reason why I think AI run VCs are going to do very very well.
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As an operator your job is to create and maintain value for your customers. There is literally no other way to build a successful business. And while "create and maintain value" sounds pretty straightforward, it is an enormous and non-trivial task.
Value creation is a function of many operating units working harmoniously - product, research, marketing, engineering, finance etc. Beyond the unit's operating goals, decision making for each unit has to consider a) inter-dependencies, b) scarcity of shared resources, and c) speed.
Inter-dependencies
All operating units are recursive inputs into one another.
Engineering speed influences product releases influences marketing strategy influences finance budgeting influences hiring timeline influences engineering speed...
And this flywheel will manifest in many different ways with varying degrees of impact factors (ie how much a change in one operating unit impacts another).
Scarcity of shared resources
You have a very finite number of working hours you can get out of your team each week. If you spend resources on one operating unit, you often shrink resources available for another. The transferability of skill is abstracted away at the balance sheet level, which brings to the final consideration...
Speed
Decisions need to be made as fast as possible, validated/invalidated, and rolled back when necessary, all in the presence of a shrinking balance sheet. This means you're typically operating with incomplete information. Indecision is the kiss of death.
Altogether, this creates a fascinating problem space of complexity to explore but it often makes it difficult to clearly define the problem space.
This complexity is compounded and exacerbated by the necessity to balance social dynamics within the company. And here lies the nondeterminism.
The variables I listed above are simply structured inputs into a decision making framework. The human element of operating is impossible to encapsulate into a decision making framework without the power of averages. For all practical purposes your framework is non-deterministic. This is why when building a new company, culture, like-mindedness and a shared vision are so critical. It is the only way to tame the nondeterminism of social complexity until you reach sufficient scale.
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While it may seem as though I am suggesting operators have more difficult jobs based strictly on the decision making process, there's a critical variable that's missing: magnitude.
The risk/reward profile of each decision an investor makes is far larger in magnitude than any single decision most operators makes. This requires an entirely different skillset and framework that a lot of operators struggle to grapple and this (imo) is what make great investors, great.
Conversely, many great investors wouldn't last a week operating through the complexity of day-to-day decision making.
Everyone has their strengths and weaknesses.
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All-in-all I feel incredibly fortunate to have spent my time as an investor. It's already been a valuable perspective to bring to my operating role at
@nil_foundation.
And who knows maybe one day I end up back on the other side of the table... but for now I have too much energy and passion for what we're building.
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Finally, if you're an investor looking to make a move to the operating side and want to learn more, please reach out! I'm happy to share more about my experience in DMs :)