Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
Full method →
Gil Hildebrand no published score: only 4 usable exchanges on raw tape, and a fair score needs 8+ · coarse estimate ≈4.5/5 from 4 raw tape exchanges record → ← everyone
Every exchange below was scored with names hidden, four dimensions each from 1 to 5.
An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression.
The published score averages the raw tape exchange scores and shrinks small samples toward the
cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only
toward coarse estimates, never toward a full score.
Answered raw tape
D 5 · C 5 · P 5 · Cm 5 5.00
Q Well, I think that's super interesting that you actually attempted To build a business in an industry that you really didn't know all that much about. And that's one of the reasons why I wanted to bring you on the channel is you had this interesting strategy on how to validate an idea that maybe you weren't fully deep into. Can you tell me a little bit more about that?
A I did what anyone would do. I signed up for X. I opened up a brand new account, uh, with zero followers, and I started following everyone in the YouTube space from there. I, uh, You know, started finding opportunities to create things of value for people in that space using my skill set as a software engineer. So I started putting together little pieces of content and I would put it out there using viral giveaways on, on X. And from there I was able to build up an email list of over a thousand people. You know, every week or so I would just hit, hit up this list with new findings that I had. And in the background, I would reach out to Each person individually to talk to them about this idea for this app that I wanted to build. So I was getting feedback on this idea. And when I realized I had something, I knew it was time to monetize it. So I mocked up this idea and I, uh, then knew I needed to get validation on it. So I set up a presale. The presale was 50 licenses of the software that are basically lifetime subscriptions to it. And it was at kind of an absurdly low price. I figured if I could sell these, that it was validation that this is actually a product that people would want to buy. The first 10 licenses were super, super cheap. And then every 10 after that went up. So there was a little bit of FOMO for those early adopters. Pretty quickly it sold out, I think within two…
AI assessment note: “I set up a presale. The presale was 50 licenses”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q amazing. I think it's one of the best pieces of advice for anybody bootstrapping anything with their own cash. What I really want to get from you, and I think a lot of people watching this would be wondering, if you were to give advice to someone watching right now on how to do that, what would be your exact playbook if you had to start over from scratch today?
A Well, step one is you have to build an audience because if you don't have an audience, you don't have anyone to sell to. People buy because they trust you. And especially today when it's so easy to create products that there's a million products out there, people buy based on believing in a brand or a person. Post the raw, you know, build in public type stories of you with your thought process and what you're doing. And that will help establish trust with people. The way I did that was just by putting out Free things of value that took me time to create, but I knew would be helpful to other people. In addition to just showing up and being really authentic about who I was and why I was there, that alone can get you an audience of people that trust you and are engaged with you. And that really is the first step. Step two is you've got to set up an email list and start communicating with people at least once a week. So while your social media can be a great way to kind of interact with new people, Your email list is really where you're building that trust. And what's cool is that when you start emailing people, they will email you back and you start this dialogue and you can start to talk to them about your idea. You can even use your email list to put out your ideas, get the replies back as your feedback on how to improve your idea. Show up, do that weekly, because when it's time…
AI assessment note: “Well, step one is you have to build an audience”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Okay, so you're in this VC world, you work on and sell multiple companies. How do you decide to go the bootstrap route, and how do you come up with an idea that eventually makes 30,000 dollars a month?
A Well, there was nothing wrong with the VC backed route, but after selling that last company, I was really excited for a change. I started posting videos on YouTube, talking about my ideas for what kind of company I would want to start next. At the same time, I was getting more into YouTube itself and getting into this idea of faceless YouTube channels where you can create channels on the backend. So I started putting together a team. I quickly realized that script writing is this huge bottleneck. It's actually really hard to find good script writers, even though we sort of know what a good YouTube script looks like. I tried using ChatGPT and I saw that it was nowhere near good enough to, you know, write the kind of script that I wanted to see. But I made a bet that if I took all of my experience as an entrepreneur and as a software developer, that I could build a solution that actually worked.
AI assessment note: “I quickly realized that script writing is this huge bottleneck.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q get back to the video. I think that's really important that you mentioned there, that final catch, which you didn't really mention right until the end, which is you actually hadn't built the product yet. This is why I wanted to bring on the channel because I think this is so genius. Can you break this down a little bit more about why this works and why you did this?
A The curse of being a software developer is that it's so easy to fall in love with an idea. And I've done this so many times before. Too often we just get excited about that invention without making sure that it's actually like a painkiller. So as an entrepreneur, we always want to be selling a painkiller, not a vitamin. A vitamin is a nice to have a painkiller. Is something you have to have, and it's going to sell a lot better. The traditional advice with startups is to go and talk to your friends and say, what do you think about this idea? Give me feedback. Maybe the next level of advice would be to say, how much would you pay for this tool if it existed? I actually think that that feedback is not good enough. In fact, it's actually quite dangerous because it lets you think you have validation. So you go in a hole. For three months or however long it takes to build this thing. And then you pop up for air and you say, Hey guys, it's ready. And the problem with that approach, they say, you know, I would be willing to pay 20 dollars a month if I didn't have this other subscription, or I would be willing to pay once I get this check-in from my old company. And I've seen this happen so many times. So the only way to really get validation is to collect money from people. And the faster you can get to that, the more likely it is that your startup is going to succeed.
AI assessment note: “the only way to really get validation is to collect money from people.”
