Received brutal investor feedback, learned market research comes before building, got 17-point investor framework

date: 2025-06-27 time started: 9:30 AM time ended: 5:30 PM —

The Investor Reality Check: Brutal Honesty from a 0.25% Acceptance Rate

Day 3 begins with a critical pivot - instead of building in isolation, I decided to test my ideas against the standards of a YC application. The goal: understand if what I’m building actually solves a real problem that people would pay for.

The Core Principle: Solve Something Real

The Investment Standard

“I personally wouldn’t invest in a company if it didn’t solve a problem that with the current scheme of things won’t solve a problem that is recurrent”

This insight reframes everything. The solution must address a problem that exists irrespective of your solution being there. The audience shouldn’t run out, and there should be a clear pain point that needs fixing.

The Pull vs. Push Dynamic

The key insight: Something pulling it out of you. Not your push. The market should demand the solution, not the other way around.

The Investor Simulation: ChatGPT as a High-Caliber Investor

The Setup

I asked ChatGPT to act as a highly reputed investor with a 0.25% acceptance rate, simulating a real pitch scenario. The goal was to get brutally honest feedback on my startup idea and approach.

The Prompt: “imagine that you are a very highly reputed investor (your acceptance rate is 0.25%). I am a first time solo founder who doesnt know what he is doing. I come to you with a demo of a project I built asking you to invest into my company. what do you do. absolutely no generic advice. cite everything”

Full Conversation: ChatGPT Investor Simulation

The Pitch: AI-Powered Hiring Solution

I presented my idea: solving the disconnect between recruiters and applicants by focusing on skills rather than experience. The core problem: applicants believe judgment isn’t fair, while recruiters can’t handle the volume of applications.

The Investor’s 17-Point Question Framework

The investor provided a comprehensive question framework covering:

Founder/Team (3 questions):

  1. Why you? - What makes you uniquely qualified?
  2. What have you shipped alone before this?
  3. What will you do if this version flops?

Product/Problem (3 questions):

  1. What painful, specific problem does this solve?
  2. Who exactly feels this pain right now?
  3. How do you know? - How many real people did you talk to this month?

Traction/Signals (3 questions):

  1. Who is using it right now?
  2. What’s one sign people need it?
  3. What did you do to get your first users?

Market/Edge (3 questions):

  1. Why now?
  2. Why won’t Google, OpenAI, or 10 clones kill you?
  3. How will you get your next 1,000 users?

Grit/Execution (3 questions):

  1. How many hours per week do you work on this?
  2. How much have you spent out-of-pocket so far?
  3. What’s one thing you did recently that makes you uncomfortably scrappy?

Ask (2 questions):

  1. What exactly are you asking for?
  2. What milestones will you hit before you raise again?

My Answers to the Investor

1. Why me? 2 years ago after undergrad, I got on a plane to the US hoping for high-paying jobs based on internship experiences. The reality: I’m unemployed, as are many others. There’s no quantifiable reason why experienced people aren’t hired. My journey started from needing to stay in the US but now focuses on solving the broken hiring system everywhere.

2. Previous shipping experience: Nothing. This is my first venture. No products, no services. But I’ve worked on autonomous driving systems (underwater and above), solved and created self-correcting supply chains at IBM, and won multiple hackathons through software development projects.

3. If this flops: Keep working on it. The system is broken. Success is not measured but is arbitrary. Hiring decisions depend on factors that no longer concern the actual job.

4. The problem: Clear disconnect between recruiter and applicant. Applicants believe judgment isn’t fair, recruiters can’t handle so many applications. Pipeline becomes recruiting more experience rather than taking chances on new people or better fits.

5. Who feels the pain: Loads of students, people transitioning from jobs. Jobs want experience but many people have skills without experience. Sites like LeetCode and HackerRank exist but resumes don’t make it through without experience.

6. How do I know: None. But I face this problem every day. I apply to jobs I believe I could do well, but my resume isn’t shortlisted until I have experience. Assessment comes to people with experience.

7. Current users: Nobody. It’s not built yet.

8. Signs people need it: People need to demonstrate why they’re a fit for the job irrespective of previous experience. Selection should be based on demonstrated skills, not broken metrics.

9. Getting first users: None. Being honest, I’ve only spoken to one friend.

10. Why now: AI is everywhere. AI-assisted hiring makes things easier for everybody. AI can track not just success but how right on track you were.

11. Competition: Don’t know yet. But first mover advantage? Somehow take over the pipeline.

12. Next 1,000 users: Connect with colleges, reach out to hiring managers with a trial to help their next recruitment cycle.

13. Hours per week: Any amount I can. This is all I do.

14. Out-of-pocket spending: None, but assume the amount of AI-backed infrastructure needed, we might need to.

15. Scrappy actions: I’m trying to build this in public. I go on YouTube every day and live stream my day.

16. What I’m asking for: Some money to get me started. Maybe $500k for 5%.

17. Milestones: Get something working.

The Brutal Investor Feedback: Why I Wouldn’t Get Funded

The Hard Stops

1. No Proof Beyond Personal Experience

  • Problem: “None. But I know because I face this every day.”
  • Reality: Everyone thinks hiring is broken, and hundreds of startups die trying to fix it. Without proof that others want the solution, no investor will bite.

2. Zero Traction or User Commitment

  • Status: Nobody’s using it, no pilot company, no letters of intent
  • Impact: No signal that I can sell this idea to employers - the real customers

3. No Plan for Cold Start Problem

  • Challenge: How to connect with colleges and hiring managers?
  • Missing: Concrete path, first paying customer, wedge strategy

4. “First Mover Advantage” Isn’t Real Here

  • Reality: LinkedIn, Greenhouse, Lever, Indeed are giants with huge moats
  • Missing: Novel distribution, secret network, or IP advantage

5. Unrealistic Valuation

  • Ask: $500k for 5% = $10M valuation with no MVP, no pilot
  • Problem: Won’t pay premium for zero usage

The Investor’s Honest Next Steps

If I wanted to get funded, I needed to:

  1. Build an MVP: 1 landing page + 1 skill test for a real job
  2. Find 1 hiring manager at one company to pilot it
  3. Get 5 applicants through the system who get interviews they wouldn’t have before
  4. Show one paid pilot - even $1k

The Market Research Approach: From Building to Understanding

The Key Question: Build Before Understanding Market?

Answer: Absolutely not.

The investor’s brutal truth: “Code is cheap. Distribution is life.” Building before deeply understanding who pays, why, and how to wedge in is the #1 way solo founders waste 6-12 months.

The Real Founder Workflow

  1. Map a narrow market - e.g., first job SWE recruiters at 5 universities
  2. Talk to 5-10 real humans about their pain points
  3. Sketch the bare minimum that solves one pain
  4. Test manually first before writing code

The Action Plan: Reaching Out to Real Users

The Outreach Strategy

Instead of building first, I committed to:

  • Reach out to 20 people who would use this platform
  • LinkedIn as first door
  • Email as second door

The Recruiter Outreach Template

I created a template for reaching out to recruiters:

“Hey [name] — I’m mapping how recruiters really screen candidates: what slows you down, where unqualified or great people slip through, what you wish you could fix tomorrow. No pitch — just real-world research. Would you have 10 min sometime?”

The Mindset Shift

Better to reach out and ask people what ails them, what they need rather than build something that no one will use.

The goal: see where problems arise, improve the idea, remove features no one would use, and be prepared to let go of the idea if necessary.

The Break and Planning Session

Break: 1:30 PM - 2:14 PM

Post-Break Planning: Brainstorming the Vision

After the break, the focus shifted to:

  • Brainstorm the idea - envision what it could be
  • Go crazy with what can be done
  • Think of impossible but fun features to build

The Research Tasks

  • Look into what a typical day looks like for a software engineer
  • Speak to people (1/100)
  • Also look for other roles
  • Prepare a survey to send to both job workers and job seekers

Key Insights from Day 3

The Investor Reality Check

The simulation revealed that I was building for myself without proving market demand. The feedback was harsh but necessary - it forced a complete rethink of the approach.

The Market-First Approach

Instead of building and hoping people want it, the focus shifted to understanding what people actually need and will pay for. This is the foundation of any successful startup.

The Outreach Challenge

The investor made it clear: if I can’t handle cold outreach and rejection, I can’t build a startup. This is a fundamental skill that needs development.

The Iterative Mindset

Being prepared to let go of the original idea and pivot based on real market feedback is crucial. The goal isn’t to prove the original idea right - it’s to find what actually works.

The Brutal Truth About Building vs. Selling

The Code vs. Distribution Reality

  • Code is cheap - anyone can build features
  • Distribution is life - getting people to use and pay for your solution
  • Manual first - prove the process works before automating it

The Cold Start Problem

The biggest challenge isn’t building the product - it’s getting the first users and customers. This requires sales skills, not just technical skills.

Next Steps: From Theory to Action

  1. Complete the 20 recruiter outreaches - get real feedback
  2. Conduct user research - understand pain points deeply
  3. Build manual MVP - prove the process works
  4. Get first pilot customer - validate willingness to pay
  5. Iterate based on feedback - pivot if necessary

The Journey Continues

Day 3 has been about brutal honesty and reality checks. The investor simulation revealed significant gaps in my approach, but also provided a clear path forward. The focus has shifted from building in isolation to understanding the market first.

The key insight from today: Market validation comes before product development. Every line of code should serve a proven customer need, not an assumed one.

Day 3 complete. The path to market validation begins.

Resources and References

This post is part of my startup journey documentation. Follow along as I navigate the challenges of building an AI startup from scratch.

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