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This has been my experience with so many entrepreneurs. They have these visions that are planned and structured and overly though out that they miss the primary pain point their business is trying to solve and lack the ability to pivot because they have overly planned everything out.

I have gone out with entrepreneur clients and after a few drinks I suddenly have clarity as to why they really are trying to build their app/product/etc and that always changes everything. I sorta wish people would be more honest like this more often.



I wonder how much of this has to do with the medium of communication. People often have wonderful clarity when speaking but then muddle things up horribly when they write/create decks/etc.

I previously worked with a very smart and capable woman who was in charge of a client-facing department at an agency I was part of. She would ask me to review a presentation she had put together (often sales-focused, but not always), and I'd go through and at the end I'd often find myself saying, "You know, I'm finding this is (muddled | too much information | unclear). What exactly are you trying to say?"

And then she'd give me a succinct, spoken paragraph that completely nailed it. And I would say, "Okay, write that down and present that!"

I thought about this a fair bit because it was such an effective approach. It bears noting that, AFAIK, different parts of the brain are used for written communication as opposed to spoken communication. For instance it is possible to acquire a brain injury that prevents speech but not writing or vice versa. So although I think part of this issue is psychological (people get less clear, e.g. unnecessarily formal or stilted, when writing), I think another part of it has to do with the way people think.

I think a good technique that helps with this is having someone verbally ask you pointed questions ("what does this do?", "why should I care?", "how is it different?") while being recorded, and then take your spoken answers and use those in your written materials.


I feel while decks are terrible they force whoever said intelligent individual to sit down and try and package all their thoughts into a cohesive narrative. If they can't do that, then they have a seriously problem ahead of themselves getting capital and people to come work for them.

Alternatively - if they can't do that as they are really good speakers, they need to find someone who can translate their in-cohesiveness into something digestible for other people. This skillset is very rare and I would argue is super important in the early days alongside building effective product/executing/product fit.


I often find the confusions comes from not clearly understanding what is being communicated, and what you think the other side expects. The slide deck format, is often build from top-down hierarchy. Slides for areas A, B, C. When really you might have a narrative where you want to convey the material from C, with A & B as footnotes. Are you telling a story or writing the table of contents for textbook?


Agree it isn't the be all end all - but it does force someone to think about the narrative and, to your point, who you are speaking to and what you think you need to communicate and also to try and figure out what the other side expects/knows (which is a tough thing to do).


> People often have wonderful clarity when speaking but then muddle things up horribly when they write/create decks/etc.

I find writing (narrative prose, not PowerPoint) a great way to force me to clarify my thinking.


Totally. Speaking is so easy for me, writing is a bloody challenge. I think it has to do with interaction resonance with another person, too, not just the medium.


Opposite for me. I often wish I could end verbal meetings and send a note instead.


Entrepreneurs can get better at story-telling.

But frankly, fundraising is so formal that it makes it really hard to try. You get a 30m (maybe 60 if you're lucky) slot with an investor and a pitch deck. The investor may decide to lead the meeting themselves and just ask any question that comes to mind (most questions are objections disguised as questions... Sometimes not really disguised at all) or they may just stay quiet and let you do the old pitch monolog.

In any case, it's really stressful especially for first time entrepreneurs and especially if you're introverted and not the witty think-on-your-feet type.

The good news is with time and practice you can get better at it. But generally it is soul-crushing work, at least until you find one investor who "gets" it.. And usually you only need one!


> In any case, it's really stressful especially for first time entrepreneurs and especially if you're introverted and not the witty think-on-your-feet type.

Yes, but maybe it's still a good predictor of which founders will succeed and which won't?

If you can't spontaneously answer probing, challenging questions from customers, employees, vendors, and yes investors, will you do a good job running and growing a successful company?


Many do, by eventually finding and hiring the right person.

There are a lot of confounding variables and luck involved. I’ve met some frankly terribly antisocial founders that happened to get the perfect niche, I’ve met some that worked their asses off and were doing everything right but still failed due to terrible timing and a market crash, and everything in between.


As an entrepreneur, what would you like from your investor in that initial pitch meeting?


A check


Ideally you want to know what boxes you need to tick to get the check. Do they already like the product, and just want to vet the founders. Do they not understand the problem? Do they get the product, but question its ability to scale?

Basically what is the current set of things they require more depth of understanding in order to make their investment decision.


I hear what you're saying, but I think you've drawn the wrong conclusion, from OPs story, and your experience having drinks with clients.

OP blew up in his interview and got to the truth. But really, what he shouted when out of control wasn't that different from the story that he started with. Imagine that he started with that honest story. It would have been part of his elevator pitch, and part of his deck, and he would have given that same speech a few hundred times, and all the color and passion would have long since evaporated.

The conclusion that I draw is that you get to the truth by getting someone to switch off autopilot. And that can be done by provoking an emotional reaction (not that that's what the YC guy was intending to do, I'm guessing), or by loosening up through the application of a little alcohol.


It's what I meant. The stop trying to overly polish something and just be honest with your goals. Turn off the "salesman autopilot" so to speak.


I wonder if that happens because an entrepreneur may be caught up in a feeling of what needs to be done, but has yet to clearly articulate the pain/joy/humor driving the work. It wasn't until the OP really pushed himself that he articulated the pain-point his startup was trying to solve.

[Edited for grammar]


So "Keep It Simple, Stupid" is forgotten for whatever reason?


> I sorta wish people would be more honest like this more often.

I don't believe that the majority are being intentionally dishonest


It is that inherent human tendency and bias that limits one’s worldview, a concept I have grappled with and am still learning to manage every week that goes by.

We as humans are all victims to it and we (at least most of us here on HN) recognize the patterns and the innateness within our own selves.

Hopefully as a society we can begin moving forwards to a point in which we are taught from a very young age to recognize these biases and unintentional and/or subconscious behaviors of ours that may be counterproductive to our own individual goals and efforts.


I think everyone appreciates and responds better to a genuine human interaction, even if they don't realize it.

The first things I look for when I'm evaluating someone in almost any context are:

* stand for something, anything

* show me some passion and where you find joy or, conversely what makes you sad.

* tell me what you don't do/support/optimize. Negative space




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