Chapter Six

Keep Your Friends Close

The Importance of Trust

Before you run these exercises

Chapter 6 makes an argument that unsettles most founders: by the time you're pitching, the trust question may already be mostly answered — and not by your deck. The chapter breaks down what trust actually consists of, why investors need three distinct kinds of it, and what the spectrum of community trust looks like in practice.

There's a framework in this chapter — a scale from 5 to 11 — that is worth reading before you try the exercises below. Where you sit on it right now is more important than any slide you'll put together this week.

📸 Do this before Exercise 01
From the book · Snap & upload
Chapter 6 has a visual framework that maps exactly where you stand in terms of how people talk about you when you're not in the room. Before you run the exercise below, snap a photo of it in your copy of the book — then upload the photo directly into Claude as part of your prompt. Claude can read it and apply the actual framework to your situation.
Claude
Exercise 01
Diagnose Which Kind of Trust You're Missing

The chapter breaks investor trust into three distinct types — and they're not interchangeable. Knowing which one you're missing tells you exactly where to focus before your next meeting. Read Chapter 6 to understand what each type is, then use this exercise to diagnose your gap.

Most founders who are struggling to raise are missing one specific type more than the others. Knowing which one it is tells you exactly where to focus before your next meeting — and what to stop wasting time on.

Prompt → Claude
I'm uploading a photo of the Community Trust Scale from Chapter 6 of Founder Unfriendly. Use the actual descriptions from the image — don't substitute your own framework. Ask me questions to figure out where I honestly sit on this scale right now — one at a time. Be honest about what you're hearing. I want to know which level I'm most deficient in and specifically why, based on my answers. After 6–8 questions, give me your honest read: which level on the scale I'm currently at, what evidence pointed you there, and what are the 2–3 most direct things I can do to move up before I start pitching?
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The chapter's most pointed line: "If you're not getting yeses, perhaps you need to stop working on your pitch deck and go work on increasing the passion level of your biggest fans." If the diagnosis points to community trust, that's the answer. No deck improvement will substitute for someone saying "I'd back them again in a heartbeat."
Claude
Exercise 02
The Blank Check Test

The chapter describes a specific test: go to the most financially capable people you know and ask them — hypothetically — how much they'd invest in a startup idea from a trusted referral. Then ask how much they'd invest in you specifically, even before you have the idea fully formed.

The gap between those two numbers is a direct measure of your personal trust capital. The closer they are — or if the "you" number is actually higher — that's blank check trust. Most founders have never actually had this conversation. AI can help you prepare for it and interpret what you hear.

Prompt → Claude
Help me prepare for and interpret the "blank check test" from the book Founder Unfriendly. The test works like this: I ask a financially capable person in my network three questions in sequence: 1. "Would you ever consider investing in a startup from a trusted referral?" (Establishes baseline willingness) 2. "If the idea blew you away — in a space you knew, with a great team — what would your max check be?" 3. "What if I told you I was starting something in a space I know well, but I haven't fully defined the idea yet? What's your number for me, specifically?" The gap between answers 2 and 3 reveals how much trust they have in me personally vs. in a well-vetted opportunity. First, help me prepare: who in my network should I run this test with, and how do I make the conversation feel natural rather than like a test? Give me a few ways to open the conversation authentically. Here's my network situation: [describe who you're closest to — former colleagues, family, advisors, mentors — and roughly what their financial profiles look like] Then, after I run it, I'll come back and tell you what I heard. You'll help me interpret the gaps.
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Run it with 3–5 people, not just one. The individual numbers will vary based on personal wealth and risk tolerance. What you're looking for is the pattern: is the gap consistently large (idea matters more than you do) or consistently small (you matter as much as the idea)? A consistent small gap across multiple people is a strong signal. A consistent large gap tells you what work remains.
Pitch exercises
Claude
Exercise 03
Strip the Pitchspeak From Your Story

The chapter identifies a specific failure mode it calls "downshifting" — founders trading their genuine motivation for cookie-cutter slide templates and buzzwords like "disruption" and "democratization" that investors have heard hundreds of times. The problem isn't the information in the deck. It's that sanitized pitchspeak actively destroys trust because it makes you sound like everyone else, and trust is built on sounding like yourself.

The chapter's question is precise: what do you want the investor to feel? Not think — feel. Claude can help you identify where you've downshifted and recover the human story underneath.

Prompt → Claude
I want you to help me strip the pitchspeak out of how I talk about my company and recover the real human story underneath it. Here's how I currently describe what I'm building — this is roughly what I'd say in a pitch or an email: [paste your current elevator pitch, deck intro, or investor email] Do three things: 1. Flag every phrase that sounds like it was written for a pitch deck rather than spoken by a human — buzzwords, passive constructions, phrases that could apply to any startup ("disrupting," "democratizing," "at scale," "synergies," "the future of X"). Be ruthless. 2. Ask me the questions underneath the pitchspeak: Why do you actually care about this problem? What's the real story of how you got here? What would you be doing if this company didn't exist? What do you want an investor to feel when you're done talking? 3. Using my answers, rewrite the opening of my pitch — same core information, but in the voice of a real person who is genuinely obsessed with this problem. No buzzwords. No deck language. The kind of thing that makes someone lean forward instead of lean back.
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The rewrite should make you slightly uncomfortable. If it sounds exactly like what you'd put in a deck, Claude didn't go far enough. The version that builds trust is the one that sounds personal — specific to you, specific to this problem, specific to why the market seems to have chosen you to solve it rather than the other way around. That specificity is what makes it memorable.
Claude
Exercise 04
Build Your Trust Compound Plan

The chapter borrows an observation from someone who has raised billions in investor capital that reframes when fundraising actually begins. It's in Chapter 6. Trust compounds over time and can't be manufactured in a three-month sprint. But that doesn't mean there's nothing to do right now. The chapter lists specific trust-building behaviors — being visibly reliable, helping without expecting returns, developing a reputation for transparency, becoming known for something — and each of them can be started today.

The gap between where you are on the trust scale and where you need to be to close a round is a plan, not a verdict. Use Claude to build it.

Prompt → Claude
Help me build a concrete trust-compounding plan based on the framework from Founder Unfriendly. The book identifies these specific trust-building behaviors: - Being visibly reliable in any context (doing what you say, meeting deadlines, showing up prepared) - Helping others without expecting immediate returns (intros, advice, feedback) - Building a track record of learning fast (stepping into unfamiliar problems and making progress) - Developing a reputation for transparency (sharing wins and losses honestly) - Being consistent over time (not only visible when you want something) - Becoming known for something specific (a domain, skill, or approach) - Staying in touch and top of mind (regular check-ins, sharing what you're learning) - Treating small asks like big ones (gratitude and follow-up that's memorable) - Creating positive social proof (multiple respected sources saying the same things about you) Here's my honest self-assessment of where I stand right now: [describe how you'd rate yourself on each of the above — be honest, not aspirational] Here's my timeline before I plan to start pitching: [weeks or months] Based on this, give me: 1. The 3 behaviors I should prioritize given my timeline and my gaps 2. A specific, concrete action for each — not "be more reliable" but "do X with Y people by Z date" 3. One thing I can do in the next 7 days that would move the needle on community trust specifically
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The chapter ends with a line about timing that's worth reading. It reframes when fundraising actually starts — and what you've already been doing (or not doing) for years without knowing it. It's one of the more uncomfortable things in the book. Go read the end of the chapter.
Before you move to Chapter 7

Chapter 6 is asking you to reckon with something most pitch advice skips: the pitch is not where trust is built. It's where trust is confirmed or denied. If the trust isn't already there — in how people talk about you when you're not in the room — no slide template will fix it.

Before you move on: know which trust type is your biggest gap, have a plan for closing it, and look honestly at where you sit on the 5-to-11 scale. If the honest answer is 5 or 6, the most valuable thing you can do before your next pitch meeting is not refine your deck. It's figure out how to move one level up — and that means doing something real, not something polished.

Founder Unfriendly by Charlie O'Donnell. Published by Wiley.
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