Chapter Three

I'm Putting Together a Team

Attracting Help and Support

Before you run these exercises

Chapter 3 reframes what "team" means at the earliest stage — and the answer is probably not what you're thinking. There's a specific way the best early companies are structured that has nothing to do with org charts or headcount, and understanding it changes how you spend the next six months before you raise.

The chapter also covers something most founders get badly wrong about building their network — and offers a concrete, repeatable system for fixing it. One of the exercises below is taken almost directly from a suggestion the book makes about using AI. It's one of the few places the book names the tool explicitly.

Claude
Exercise 01
Build Your Curiosity Flywheel: Who to Interview and What to Ask

The chapter opens with a story about someone who built one of the most influential networks in venture starting from nothing — no connections, no credentials. The mechanism wasn't charm or luck. Read the chapter to find out what it was, then use this exercise to build your version of it.

Most founders underestimate how accessible people are when you approach them as a student rather than a pitcher. The chapter calls this "borrowed credibility" — you don't need an audience of your own because the person you interview has one. AI makes the preparation effortless enough that the only remaining excuse for not doing this is inertia.

Claude can search the web — ask it to find real people active in your space right now.

Prompt → Claude
I'm building a company in [your space] and I want to start a curiosity-driven interview series — a podcast, LinkedIn video, or newsletter — to build my network and establish credibility as a student of this space. Help me: 1. Identify 10 people in or adjacent to [your space] who would make compelling interview subjects — a mix of well-known names who would lend credibility and emerging voices who are doing interesting work but are more reachable. For each, note in one sentence why they'd be a great guest and what they're known for. 2. Suggest 5 panel-style topic areas that are genuinely debated in this space right now — questions that don't have obvious answers and that would make a thoughtful practitioner want to weigh in. 3. For the first person on your list, draft 6 sharp interview questions — the kind that show I've actually done my homework, not generic "what's your advice for founders" questions.
💡
The outreach is the easy part. Once you have a list and good questions, use Claude to draft the cold outreach message — short, specific, referencing something they've actually said or published. The book's point stands: people with audiences need to feed them. You're offering to help. Most will say yes more often than you think.
NotebookLM
Exercise 02
Mine the Founder Interviews That Already Exist

Before you start doing your own interviews, there's a faster first step: hundreds of founders in your space and comparable spaces have already been interviewed — on podcasts, in newsletters, at conferences. They've explained what they got right, what they got wrong, what they wish they'd known earlier, and what the pattern is for companies that made it. That knowledge is sitting in transcripts and YouTube videos, largely unread.

NotebookLM (notebook.google.com) is Google's research tool that lets you upload a collection of documents — podcast transcripts, interview articles, investor memos, blog posts — and then have a genuine conversation with all of them at once. You can ask it to find patterns across 20 founder interviews, pull out what the successful ones had in common, or surface the insights that seem to generalize to your specific situation today. It's the kind of synthesis that used to take weeks of careful reading compressed into an afternoon.

The output isn't just research — it's a founder playbook built from people who've actually done it in adjacent territory.

Step 1 — Gather your sources use Claude or Perplexity
Find me 10–15 long-form interviews, podcast transcripts, or written profiles of founders who built companies in or adjacent to [your space] — specifically people who successfully raised a seed or Series A round and whose companies are still operating or had a meaningful exit. For each, give me the title, source, and a direct link. Prioritize interviews where the founder talks candidly about what worked and what nearly killed the company — not just highlight-reel success stories. Include at least 2–3 from the last 18 months so the context is current.
Step 2 — Upload to NotebookLM notebook.google.com
Go to notebook.google.com and create a new notebook. Upload the transcripts or paste in the articles as sources. Then ask NotebookLM the following questions — one at a time, reading the answers before moving to the next: 1. What do the founders in these interviews identify as the moment that most changed the trajectory of their company — positively or negatively? 2. What mistakes do they most commonly say they made early on that slowed them down — and which of those mistakes seem like they'd still apply to a founder starting today? 3. What did the successful ones say about how they found their first customers — what actually worked versus what they thought would work? 4. What patterns do you see in how they talked about their fundraising process — what made the difference between getting funded and not? 5. What advice do they give that seems specific to their era or context — and what generalizes to someone building in this space right now?
Step 3 → Claude synthesize into a playbook
Here are the key insights I pulled from a set of founder interviews in my space using NotebookLM: [paste your NotebookLM findings] I'm building [your company description] at [your stage]. Help me turn these insights into a one-page founder playbook for my specific situation: 1. The 3–4 things the successful founders in this space all seemed to figure out — what's the common thread? 2. The 2–3 early mistakes I should specifically try to avoid based on what I've read 3. What seems genuinely different about building this today versus when these founders built it — what advice might be outdated? 4. One question these interviews raised that I still don't have a good answer to — something I should go find out
💡
NotebookLM also generates a podcast. Once you've uploaded your sources, it can produce an audio summary of the key themes — two AI hosts discussing the patterns across your documents. It's surprisingly useful for absorbing the synthesis on a walk or a commute. Not a replacement for reading, but a good way to let the patterns settle.
Claude
Exercise 03
Write Your First Heartbeat Email

The Heartbeat Email is one of the most practical, underused tools in this book. The premise: a short, warm, personal update sent to your network on a regular cadence — monthly or quarterly — that makes you memorable as a full human being, not just a LinkedIn title. The book is specific about what goes in it: a professional update, something personal, a reflection, and a hook.

The failure mode is sending something that sounds like a corporate newsletter. Claude's job here is to make it sound exactly like you — and to hold the format without letting it get stiff.

Prompt → Claude
Help me write my first Heartbeat Email — a short, warm personal update to send to my network. This should not sound like a company newsletter. It should sound like a real email from a real person who happens to be building something. Here's the structure I want: - Opening: Warm, grounded in something current (season, a recent moment, something small and human) - Professional update: What I'm working on, something I'm proud of, and honestly one thing that's been hard - Personal note: Something outside of work that's real — a hobby, a moment with family, something I've been thinking about - Reflection: One idea or thing I've been chewing on lately — something that made me think - Hook/ask: Something coming up, a resource I'm looking for, a city I'll be in, or a question I want answered - Closing: Light, open, grateful Here's the raw material — tell me what you've been up to and I'll shape it: [dump your notes here — professional wins, struggles, what you're building, what's been on your mind personally, anything coming up] Tone: conversational and warm. Not corporate. Not a press release. The kind of email you'd actually want to receive from someone you like.
💡
Save the format, change the content. After Claude writes your first one, save the structure as a template. Each month or quarter, you just dump new raw material into the same prompt. The format stays consistent; the content stays fresh. Over time you'll find that people start responding — not just when you ask for something, but because they genuinely like hearing from you.
Co-founder & hiring
Claude
Exercise 04
The Co-Founder Alignment Test

The book explicitly calls out AI for this exercise — one of the few places it names the tool directly. It's in Chapter 3. Read that section, then run this prompt.

Most co-founder relationships break down not because of bad intentions but because of unexamined assumptions — about who makes what decisions, about what "fair" looks like when one person is more technical, about what happens when one person wants to sell and the other doesn't. The time to surface these is during the trial, not two years in when you're stuck.

Prompt → Claude
Generate a co-founder alignment questionnaire that two people considering starting a company together should each fill out independently before comparing answers. The questionnaire should cover: 1. Values & Mission — Why are we building this? What does success look like in 10 years? 2. Roles & Ownership — Who owns what decisions day-to-day? What happens when we disagree? 3. Equity Philosophy — How should equity be divided, and on what basis? What happens if one of us leaves in year one? 4. Work style & Commitment — What does "full-time" mean to each of us? How do we handle stress differently? 5. Governance & Decision Rights — What decisions require both of us? When does one person have final say? 6. Money — What are our personal financial runways? What's the minimum salary we each need to function without panic? 7. Worst-case scenarios — What does each of us do when we're at our worst under pressure? What would make us want to leave? 8. The exit question — Under what circumstances would we want to sell? What would make us refuse a deal? Make each question specific enough that two people might genuinely answer differently — not softball questions with obvious "right" answers. The goal is to surface real disagreements before they become crises.
💡
Do this before the two-week trial. The book suggests a short working sprint together — ship something small, run 10 customer calls, see how you operate under pressure. Fill out the questionnaire first, compare your answers, and then do the sprint. Misaligned answers on the questionnaire don't disqualify someone; they tell you what to watch for during the trial. Unresolved misalignment after the sprint is the real red flag.
Claude
Exercise 05
Design Your Trigger-Based Hiring Blueprint

The chapter has a specific framework for when to hire that most founders get completely backwards — one that changes how you think about the whole timeline. Read that section in Chapter 3, then use this prompt to apply it.

AI can help you design the full blueprint before you've made a single hire.

Prompt → Claude
Help me build a trigger-based hiring blueprint for my company. I want to design the team I need over the next two years — not based on a calendar, but based on specific business milestones that would justify each hire. Here's my company: [describe what you're building, your current stage, what you've already built or proven, and what your rough funding situation is] For each functional area below, help me define: - The trigger: what milestone or proof point would justify making this hire? - The first hire: should it be a fractional "pro" or a full-time junior? What does the pro/rookie split look like for this function? - What "good" looks like: what would this person accomplish in their first 90 days that would tell you the hire is working? - Equity guardrails: roughly what equity range is appropriate, and what's the risk of over-equitizing too early? Functional areas to cover: engineering/product, sales, marketing, operations, finance. Flag any area where I don't have enough information yet to make a smart hiring decision — those are the gaps I need to fill before I can answer this well.
💡
Then pressure-test it with a real operator. The chapter says to go function-by-function with people who have lived it — not ask generically. Once Claude gives you a blueprint, use it as the agenda for conversations with experienced operators in each function. "Here's my hiring plan for sales — does this trigger make sense to you?" is a much better use of their time than "what should I know about hiring salespeople?"
Structure & accountability
Claude
Exercise 06
Set Up Your Pre-Board

The "Board Before the Board" is one of the most useful concepts in the chapter — a lightweight monthly meeting with three trusted people before you have real investors or a formal board. The three personas the book describes: the Business Modeler (creative with numbers, full of ideas that actually pencil out), the Insider (voice of your customer in the room, knows the history of attempts in this space), and the Lifeline (your honest friend who calls out your bullshit while also being in your corner).

Most founders skip this because they don't want accountability before they have to have it. That's exactly backwards. The pre-board is where you catch the mistakes before they compound. Use Claude to find your candidates and draft the structure.

Prompt → Claude
Help me set up a Pre-Board — a lightweight monthly advisory group that gives me real accountability and honest feedback before I have formal investors or a board of directors. I need three people, each filling a specific role: - The Business Modeler: someone who understands multiple business models and can stress-test whether the financial logic of my idea actually works - The Insider: someone who is genuinely part of my target customer world — they'd use this product, they know why previous attempts at this problem failed, and they can make meaningful introductions - The Lifeline: a trusted person who will tell me the truth even when it's uncomfortable, while also being genuinely in my corner Here's my company and what I'm building: [describe your idea and stage] Here's who I know well enough to approach: [list anyone who comes to mind — don't filter yourself yet] Help me: 1. Map the names I've listed to the three roles — who fits where, and who has gaps I need to fill? 2. For anyone who doesn't obviously fit a role, suggest what role they might fill and why 3. Draft a short ask I can send to each person — honest about what I'm building, what I'm asking for (monthly meeting, an hour or so), and what they'd get out of it
💡
On compensation: the book says you can pay these folks in dollars, sometimes pizza, and small equity (around 0.10%) if the company becomes real. The honest ask is usually enough — most people will say yes to a monthly meeting with a founder they find interesting if you're clear about what you need from them. What they rarely say yes to is vague. Be specific about the time commitment and what you're actually asking them to do.
Build something
Notion AI
Set Up Your Pre-Board Meeting Doc in Notion

The pre-board meeting agenda is a recurring structured document — the same sections filled out fresh each month, with a history you can look back on. That's exactly what Notion is built for. Notion AI can scaffold the whole template in about 30 seconds. No app to build, no setup friction, and it lives where you probably already do your writing.

Notion AI Prompt
Create a monthly Pre-Board meeting template for an early-stage startup. Each month I fill this out before meeting with three advisors. Include these sections with a brief prompt inside each one to remind me what to write: - Meeting Date - Hypotheses (what we currently believe about the business) - Goals (what we set out to test since the last meeting) - Inputs & Effort (how many outreaches, demos, calls, prototypes) - Outcomes (measurable results) - Learnings (what surprised us) - Decisions & Next Bets (what we'll do before next meeting) - Asks (intros needed, specific feedback, anything I need from advisors) Add a simple status indicator for each section: 🟢 On Track / 🟡 In Progress / 🔴 Blocked Make it clean and fast to fill out.
🤝 Claude + Notion via Cowork
If you use Claude's desktop app (Cowork), Claude can read and write to your Notion workspace directly. You can ask it to prefill the Outcomes and Inputs sections by pulling from notes you've dropped elsewhere, or to draft your Learnings section from a rough bullet dump. Useful if you're pressed for time before a meeting and need to turn messy notes into a clean update fast.
Before you move to Chapter 4

Chapter 3 is ultimately about one thing: you cannot build this alone, and the sooner you start acting like that's true, the faster everything moves. The parade doesn't assemble itself — you have to start walking and invite people to join.

Before you move on, you should have three things in motion: some version of a curiosity content practice (even just one interview scheduled), a heartbeat email drafted or sent, and a pre-board in place or at least three names identified for the three roles. The co-founder alignment questionnaire and the hiring blueprint are tools to use when the moment is right — but having them ready before you need them is the whole point.

One more thing worth repeating from the chapter: don't pre-reject yourself. You don't know where someone is in their career. The worst they can say is no. And even the no's build the funnel.

Founder Unfriendly by Charlie O'Donnell. Published by Wiley.
Order the Book →
← Chapter 2: Show Me the Money