Before you run these exercises
Chapter 9 is the longest and most operational chapter in the book. It covers the full pitch architecture: how to get into the flow before you're raising, how to write the email that earns the meeting, what "team/market/traction" actually means at each tier, how to structure a deck as a narrative rather than a template, how to handle the room when you're in it, and how to avoid the defensive framing trap that quietly kills deals — especially for women founders.
The chapter also includes something unusual: the book explicitly suggests using AI to stress-test your deck, naming a specific prompt. Read that section before Exercise 03. There are also specific frameworks — the five hook types, the three team tiers, the promotion vs. prevention question research — that the exercises below reference directly. This chapter rewards close reading before you start prompting.
The chapter makes a sequence argument that most founders skip: you can't get an investor to open your deck unless they like your email first — and they won't read the email unless the subject line catches them. The chapter cites a specific data point about how many pitch decks actually get opened — and it reframes the whole email question. It's in Chapter 9. The deck isn't the pitch. The email earns the right to send the deck.
The chapter defines what the email body needs to establish: at least two of three boxes — team, market, traction — spelled out in plain English, not buried. The subject line has one job: make a distracted person who has seen 2,000 companies this year stop and open it. Use Claude to draft and pressure-test both.
The chapter uses the Inception analogy: your job isn't to transfer your vision, it's to plant an idea so simple and emotionally resonant that the investor feels like they came up with it themselves. The opening hook is where this happens or fails. Open with the wrong thing and they've already invented a version of your product in their head before you've described it — usually the worst version.
The chapter draws on a framework for what makes an idea feel novel to someone hearing it for the first time. There are five categories, and most pitch hooks land in none of them. Read Chapter 9 to understand the framework — then use this exercise to find which category your hook belongs in.
This exercise comes directly from the book — it's one of the few places the chapter explicitly suggests using AI on your deck. The instruction is precise: imagine the most pompous, seen-it-all VC — someone who has backed real winners and feels like they've earned the right to be dismissive. Run your deck through their internal monologue, slide by slide.
Most founders build decks hoping for the reaction of a supportive friend. The person actually reading it is closer to Simon Cowell: looking for any reason to move on, associating your company with things that already failed, asking "is this money?" before you've finished your first sentence. The chapter walks through exactly what Simon says about a standard deck — and then shows what happens when you reorder it to lead with momentum instead of credentials. Read that section before you run this prompt.
The chapter makes an argument about timing that most pitch advice misses: nail the timing, and even a decent team with a passable product can ride a wave they didn't create. The inverse is also true — a great team with a great product can fail simply by being too early. Investors know this. Which means showing them market momentum before you explain why you win is often more persuasive than leading with product.
The chapter calls this the inevitability frame: give investors something familiar to latch onto first. If they already believe in the wave you're riding, every other part of your pitch becomes easier to believe. The Braze example in the chapter is worth reading — a founder who found investors who had "seen this movie before" in adjacent categories and pitched it as running the playbook back, but better and at the right time.
The chapter covers two things that happen in the room that most pitch prep ignores. First: the first call with any investor should be treated as a reverse pitch — you're qualifying them as much as they're qualifying you. The chapter gives specific high-signal questions to ask that surface real intent and real objections early.
There's a Harvard Business Review study cited in Chapter 9 with a finding about investor questioning patterns that should change how you think about every meeting you walk into. The data is in the book — read that section before you run this exercise.
The promotion vs. prevention dynamic doesn't just happen once — it can take over an entire meeting without you noticing. You come in planning to tell an expansive story about a big opportunity, and by slide three you're defending your competitive moat, explaining why churn won't be a problem, and justifying your team's lack of a specific credential. You've been redirected into a defensive frame and your pitch is now about why you won't fail instead of why you'll win.
Granola captures the transcript. Claude can classify every investor question as promotion-oriented or prevention-oriented and show you exactly where the frame shifted — and whether you redirected or went along with it.
Chapter 9 is asking you to think about pitching as architecture, not performance. Every element — the subject line, the hook, the deck order, the opening question, the way you respond to prevention questions — is a design choice that either moves the investor toward a yes or gives them a reason to disengage.
Before you move on: know which two of three boxes (team, market, traction) you're leading with and why, have a hook that lands in at least one of the five novelty categories, and have done the Simon Cowell test on your deck. The last thing to carry into Chapter 10 is this: the investors who take your meeting are, by definition, always "interested." The next chapter is about what that word actually means.