I advise a small portfolio of companies at any given time. Lately, many of the mistakes I'm seeing founders & operators make can be grouped into 4 broad categories.
1. Oversimplifying
In an effort to make things seem easy or to justify hedging, lack of focus, or simply because of a lack of engagement with key details, it's often easy to collapse, conflate, and obfuscate behind an oversimplified worldview.
This oversimplification can lead to costly mistakes, oversights, and under-investment in the details that really matter.
It can also lead to false dichotomies when things are actually nuanced gradients or spectrums.
If you look closely enough, the discontinuities disappear and a smooth path appears.
This has been a big part of my advisory work lately - revealing the hidden complexity inside over-simplified things.
2. Overcomplicating
Domain experts, "big" thinkers, and philosophers are often stuffing way too many ideas into the mix.
Simple problems, processes, or strategies become bloated. 2 concepts are used when 1 more elegant one will suffice.
You want the minimum number of ideas - and no fewer (or you end up at problem number 1).
A big part of my advisory work has recently involved reducing the number of ideas, brands, surfaces, products, and approaches to reduce work and increase the quality and cadence of execution.
Genius (and value creation), after all, is reducing the complex to the simple.
3. Miscategorizing things
One of the hardest things to do is to name things. The next hardest thing is to group things into categories that are mutually exclusive and collectively exhaustive.
Naming conventions, careful attention to abstraction levels, and a strong grasp of language and cognition are critical here.
A big part of my advisory work lately has involved looking at problem domains from first principles and asking questions like
a) What is the most straightforward name to give this thing?
b) What is the right level of abstraction for this collection?
c) What is the complete set of self-describing categories that can encapsulate the whole problem without overlaps?
4. Mistiming things
When you have a big vision and a passionate team, everything can seem urgent and important.
If everything is a priority, then nothing is a priority. If nothing is a priority, then nothing will actually be finished, deployed, marketed, and scaled. And scale, of course, is the essential ingredient of success for venture-scale startups.
However, if you have a clear strategy with precise and intentional goals, a clear sequence of priorities emerges.
This is related to oversimplification. It's the sense that everything is "easy" or "the same" and can be done simultaneously. It isn't. And it can't.
The details have to be unpacked, and the order of operations must be carefully planned. Or you will find yourself taking a lot of actions but not making much progress in the right direction.