Everything I Know About Fundraising (Part 1)
Scattered thoughts from someone who's been through every round
Context: Why I Wrote This
I’ve raised just about every kind of round you can imagine.
Seed and Series A as a founder and CEO.
Series B, C, D, as a head of Finance.
I’ve run secondaries. I’ve built decks. I’ve sat in most every meeting.
And over the years, I’ve found myself repeating the same advice to founders and heads of finance again and again.
So I figured I’d write it all down.
No big thesis. No “10 steps to fundraising success.” Just a dump of the thoughts I come back to every time someone’s about to raise.
Early-Stage vs. Growth-Stage: What Changes
The most important thing to understand is that fundraising changes dramatically depending on the stage of the company. In the early days — Seed and Series A — it’s all about the team. Investors know your idea will change. What they want to know is: can you figure it out? Are you resilient, sharp, thoughtful? Are you the kind of founder they want to bet on? That’s the game.
But as you move into Series B and beyond, it’s not just about story anymore. It’s about proof. It’s about the machine. Investors want to see that the business works. That you’re not just selling vision, but that you’ve built a repeatable, scalable engine for growth. The further along you are, the more it becomes a numbers game.
Why You Need a Data Deck (Not Just a Pitch Deck)
That’s why I always recommend founders, pretty much starting at the A or B, have both a pitch deck and a data deck. The pitch deck tells the story. The data deck walks investors through how the business actually works. It’s your tool for owning the narrative before they dive into your data room and start building their own models. If you don’t tell them how to think about your business, they’ll do it for you — and they’ll use the wrong template. The data deck is how you show them your template. It frames the metrics that matter and walks them through what drives your business. We wrote about this, and shared our actual pitch and data decks, here below:
Be Intrinsic, Not Reactive
One of the biggest traps founders fall into is trying to pitch what they think investors want to hear. It backfires. You end up sounding generic. And worse, you lose your edge… the founder energy, the spark, the truth of what you're actually building. The best pitches are intrinsic. They're grounded in your own conviction. Why are you excited about this? What do you see that others don’t? Why are investors lucky to invest, not why would you be lucky to get their money?
Two Common Approaches: Process vs. “I’m Not Raising”
There are two common ways to run a raise. The first is what I call the “Process” raise. This is your classic bake-off. You’re confident: the metrics are there, the story is strong. You pull together a broad list of investors, kick them off at the same time, and try to keep them moving through the process in sync. The goal is to create competitive tension. You want to get that first term sheet and have everyone else close behind. You want to manufacture FOMO. And to do that, you need to prep like crazy and drive toward a clear timeline, ideally with a firm end date when all offers are due.
The second kind is what I call the “I’m Not Raising” raise. This is what you do when you're less sure. Maybe it’s early, maybe your metrics are soft, maybe the story isn’t quite ready. So you start having quieter conversations. You’re not pitching. You’re just sharing what you’re building and seeing who bites. And if one or two firms start leaning in, you try to build momentum from there. The upside here is that there’s no public failure if the raise doesn’t come together. You haven’t put yourself out there in the same way. The downside is you need to be okay playing the long game.
But the most important thing is that you’re intentionally out raising money. You’re intentionally running some sort of process. You’re not just casually meeting investors pitching people hoping a deal comes together. You’re either running a small “I’m not raising process” or you’re running a full on process.
Coming Up Next
More coming soon. In Part 2, I’ll go deeper into tactics: how to prepare, what not to say, and why posturing matters more than you think. Stay tuned for Friday.