Founder Unfriendly: The AI Powered Fundraising Companion to the Bestselling Book

Before you run these exercises

Chapter 1 asks a question most founder books skip entirely: should you actually be doing this? Not in a discouraging way — in a rigorous one. There's a specific exercise early in the chapter that Charlie says every founder who takes outside capital should do. Most skip it because it's uncomfortable. The ones who don't are better prepared for everything that follows.

The chapter also introduces a framework for understanding why some founders raise easily and others don't — before the pitch, before the deck, before the first meeting. The AI exercises below are built around that framework. Read the chapter first; the exercises will land differently once you have.

Claude

Exercise 01

The "Should I Even Raise?" Stress Test

One of the most underrated moments in the book is Charlie's argument that needing money is not a good enough reason to raise venture capital. VC isn't just capital — it's a specific contract with specific requirements. Most founders have never had someone push back on the "of course I should raise" assumption.

Claude will. Use this prompt to run yourself through the real questions before you commit to the VC path.

Prompt → Claude

I'm considering raising venture capital for my company. Before I commit to that path, I need you to act as a brutally honest advisor — someone who has seen what happens when founders raise money for the wrong reasons. Ask me a series of questions, one at a time, to help me figure out if VC is actually the right move. Don't accept vague answers. Push back on anything that sounds like a rationalization. When you've asked enough to have a view, give me a straight assessment: should I be raising VC, bootstrapping, raising from angels, or something else entirely? Start with the first question.

💡

How to use this: Answer every question out loud, in full sentences. The value isn't in Claude's final verdict — it's in how you feel answering the questions. If you find yourself hedging or justifying, that's the data. Let the conversation run at least 8–10 exchanges before Claude gives you a read.

Claude

Exercise 02

The Failure Visualization Exercise

This is the most uncomfortable exercise in the book, and it's the most important one. Charlie asks you to picture the morning after your company goes bankrupt — specifically and vividly, not abstractly. No income. Investors you know personally have lost their money. Your name is attached to a failure.

The exercise only works if the scenario is real. An abstract "what if it fails" won't do it. What makes it land is the specificity: whose face do you picture when you think about the money you lost? What's your name attached to publicly? Who would you have to call? Claude needs to pull those details out of you before it can make the scenario vivid enough to be useful.

Prompt → Claude

I want to do a failure visualization exercise for my startup — the one from Founder Unfriendly where you picture the morning after the company goes under. But I want it to be specific enough to actually mean something, not a comfortable abstract thought experiment. Before you paint the scenario, ask me questions — one at a time — to understand exactly what I've put on the line. I want you to pull out the details that make this real: - Who have I taken money from? Not just "investors" — whose names, whose relationships, whose trust? - What have I said publicly — on LinkedIn, to my professional community, to people I respect — about what I'm building and where it's going? - What am I known for right now, and how would a failure change that reputation? - What have I given up or delayed to do this — financially, professionally, personally? - Who in my life is counting on this working, even indirectly? - What's my financial floor — what does life actually look like if I come out of this with nothing? Once you have my answers, do three things: 1. Paint the specific failure scenario using the actual details I gave you — make it concrete, not generic 2. Ask me how I'd feel, and push back if I give you a brave non-answer 3. Ask me directly: knowing exactly this, do I still want to do it? Start with the first question.

💡

Don't rush the questions. The value is in being forced to articulate the specific people, the specific stakes, the specific reputation on the line. Most founders have kept this vague in their own heads because specificity is uncomfortable. That's exactly why you need to do it. The founder who has genuinely named the faces and the dollar amounts and the relationships — and still wants to do this — is making a real decision. Everyone else is making a hope.

Research exercises

Gemini

Exercise 03

Research the Funding Reality in Your Space

The book does something useful early: it looks at the "2% of VC goes to women" stat not as a conclusion but as a starting point for understanding how the system works. The same analysis applies to any category — most founders have wildly wrong mental models of what their space has actually raised, at what stages, and why companies in it succeed or fail.

Gemini's real-time web access makes it the better tool here. Use it to research before you pitch — not after.

Prompt → Gemini

I'm building a company in [your space — be specific, e.g., "B2B software for independent restaurant operators"]. Before I start pitching investors, I want to understand what the funding landscape in this space actually looks like. Please research and give me: 1. Notable companies that have raised money in this space in the last 3 years — what stages, what amounts, which investors 2. Any well-known failures in this space and the most commonly cited reasons they failed 3. Which investors — VC firms or notable angels — actually seem to care about this category right now? I don't want a generic list of who has written a check in the past. I want to understand who is demonstrably engaged: Who is writing or posting about this space? Who is showing up at relevant conferences or industry events? Who has been on podcasts talking about it? Who is publicly asking questions about this category or sharing opinions on where it's headed? A check written two years ago tells me less than a blog post written last month. 4. What the typical progression looks like: what milestones do companies in this space need to hit to get from pre-seed to seed to Series A? 5. Any tailwinds or headwinds you're seeing in investor sentiment toward this space right now I want the real picture, not the optimistic one.

💡

After you get the results: Feed them to Claude and ask: "Based on this, which of these investors should I prioritize reaching out to first — and what specifically should I reference when I do? What does their public writing or commentary tell me about what they actually want to see?" Someone who wrote a thoughtful post about your space last month is not the same lead as someone who appears on a list. Treat them differently.

Gemini

Exercise 04

Find Your Graduating Class

The best investor list you'll ever get isn't on Crunchbase. It's sitting in the inbox of a founder who just raised a round in your broader ecosystem — someone who spent the last six months pitching the exact investors you're about to approach, knows who passed and why, and has no reason to gatekeep that information from you.

These are founders one rung ahead of you in a non-competitive adjacent space — proptech, if you're doing something adjacent to real estate; CPG, if you're in food; fintech, if you're touching payments. Not your direct competitors. Your graduating class. They just walked the path. They have the map.

Use Gemini to identify who they are, then use Claude to figure out how to reach them in a way that makes them want to help.

Prompt → Gemini

I'm building a company in [your space]. I want to identify founders who have recently raised a seed, pre-seed, or Series A round — in the last 12 to 18 months — in adjacent but non-competitive spaces within the same broader ecosystem. For example, if I'm building in proptech, I want to know who just raised in adjacent proptech categories. If I'm in B2B SaaS for restaurants, I want to know who raised in adjacent food or hospitality tech. Please find me: 1. 8–12 founders who have recently closed a round in adjacent spaces to [your space] — be specific about the round size and date if you can find it 2. For each founder: their name, company, what they raised, and any public contact info or LinkedIn/social presence you can find 3. Any interviews, podcasts, or posts where they've talked about their fundraising experience — these are conversation starters I'm looking for people who just went through the process, not people who raised 3 years ago. Recency matters.

Then → Claude copy & paste after Gemini gives you names

I want to reach out to founders who recently raised rounds in spaces adjacent to mine. I'm not asking them for introductions yet — I want to start by asking for 20 minutes to learn from their experience. The goal is to build a real relationship, not extract a contact list. Here's my situation: [brief description of what you're building and where you are in your journey] Here's one of the founders I want to reach out to: [paste the name, company, and anything you learned about their fundraising experience from Gemini] Write me a short, direct outreach message — email or LinkedIn DM — that: - References something specific about their raise or their company (not generic flattery) - Is honest about what I'm asking for and why - Doesn't pretend this is purely about learning if I'm also hoping for intros eventually — be real about it - Sounds like a human wrote it, not a template Keep it under 100 words.

💡

What you're really asking for: When you get on the call, your most valuable question isn't "who did you pitch?" It's: "Who surprised you — either by being more interested than you expected, or by passing on something you thought was obvious?" That answer tells you more about investor appetite than any database. And yes, at the end of the call, it's completely reasonable to ask if they'd be willing to share their investor list with you. Most founders will. They remember being where you are.

Build something

Claude

Keep a Living Landscape Tracker in Google Sheets

If you're serious about understanding your funding category, you shouldn't be re-Googling the same landscape every few weeks. Keep a simple Google Sheet — companies in your space, their funding history, key investors, current status, and your notes on why they succeeded or failed. Claude can populate it directly. No app to build. No new tool to learn.

If you have Claude's Google Sheets integration connected (via MCP in Claude's settings), Claude can write this directly to a sheet for you. Just tell Claude the name of the sheet you want it to create or update. If you don't have it connected, ask Claude to format the output as a table you can paste in manually.

Create a blank Google Sheet with these columns: Company, Space/Category, Stage, Total Raised, Key Investors, Founded, Status (Active / Acquired / Shut Down), Notes.
Open Claude and run this prompt:

Prompt → Claude

I have a Google Sheet with these columns: Company, Space/Category, Stage, Total Raised, Key Investors, Founded, Status (Active / Acquired / Shut Down), Notes. Please populate it with 15–20 companies that have raised money in or adjacent to [your space] in the last 3 years. For each company, fill in every column you can find. For Status, note if they've shut down or been acquired. For Notes, include one sentence on what made them notable — a big win, a well-known failure, an unusual investor, anything worth remembering. If you have my Google Sheets MCP connected, write the rows directly to the sheet named [sheet name]. Otherwise, format the output as a table I can paste directly into Google Sheets.

Paste the output into your sheet (or let Claude write it directly if MCP is connected). Spot-check funding numbers — AI sometimes gets them wrong.
Add a tab called "Investors" and run the same kind of prompt for the investor-engagement research from Exercise 03.
Revisit it once a month. Add companies as you learn about them. The act of maintaining it is part of the research.

⚡ Power User — Claude Code

If you want to pull funding data automatically, Claude Code can write a script that fetches from the Crunchbase or Dealroom APIs and writes rows directly into a Google Sheet via the Sheets API. Ask it: "Write a Python script that pulls all seed and pre-seed rounds in [category] from the Crunchbase API for the last 24 months and appends them to a Google Sheet." You'll need a Crunchbase API key (free tier available) and a Google Cloud service account — Claude Code can walk you through both.

Before you move to Chapter 2

The point of Chapter 1 isn't to talk you out of it. It's to make sure your "yes" is a real yes.

Before you move on, you should have three things: a clear read on your founder archetype and what that means for your credibility gaps, an honest answer to whether VC is the right path or just the most obvious one, and a picture of your space that's based on what actually happened — not what you hope could happen.

If you skipped the failure visualization, go back. It's not a thought experiment. It's due diligence on yourself.