Everything I Know About Fundraising (Part 2)

Scattered thoughts from someone who's been through every round

Don’t Save Your Dream Investors for Last

One mistake I see all the time is founders saving their favorite investors for last. The thinking is, “Let me get my pitch dialed with the less exciting ones first.” I think that’s backwards. If you’re running a process, you should talk to everyone as early as you can, ESPECIALLY the firms you’re most excited about. Otherwise, they might not have enough time to really dig in or build conviction. The raise could be over before they’ve even had a chance to decide.

Prepare Like a Maniac

The way to make that possible is to prepare like hell.

I mean maniacal preparation. Weeks spent tightening your pitch deck. Building your data deck. Thinking through every single question you could possibly get asked, and knowing your answers cold. I’ve recorded myself pitching and sent it to friends. I’ve rewritten slides twenty times. I’ve practiced out loud, on walks, in front of mirrors. Whatever it takes. Because when you meet that dream investor on Day 1, you want to be ready. No “I’m still working on my deck.” You need to hit the ground running.

Get a Texting Buddy

Another critical thing to understand is that you are not on a level playing field. You’ve maybe been through one or two fundraises. VCs do this for a living. They’ve seen hundreds of pitches. They know how to read between the lines. They know what your phrasing signals, what your timing implies, and how to extract information. So I always recommend having what I call a fundraising “texting buddy.” Someone who’s done it before. Another founder you can text any time “What do I say to this?” “Should I follow up now or wait?” “Does this email set the right tone?” The words matter. Posture matters. Having a second set of eyes helps.

How to Talk About Valuation

Let’s talk about pricing.

The general rule is: never name a price, especially if you’re running a process. In a process-style raise, where you have multiple investors involved, the goal is to have them compete. You let the market come to you. When they ask what you’re looking for, you say, “We’re early in conversations and want to see what the market will bear.” Then push them. Ask, “Is this your best offer?” Let them know you’re going to review everyone’s final offers by a specific date. That’s how you generate pressure, and ideally, better terms.

Now, if you're doing an “I'm Not Raising” raise with just a few firms, it gets trickier. You still want to hold back your price as long as possible. But if you're only talking to one or two funds and they’re hesitating, sometimes you have to offer some guidance. You might need to level set so they don’t walk away thinking you’re in a completely different ballpark. Just know this: once you name a price, assume that price is known by everyone, and that it’ll anchor your deal. It’s hard to push it higher after that. So be careful, and only do it when necessary.

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Early-Stage Valuation Is Just Ownership Math

In early-stage rounds, Seed and Series A, valuation is often just ownership math. Most firms want 15 to 20 percent of the company. So if you ask for $2 million, you’re going to end up at a $10 million post. If you ask for $4 million, that’s more like a $20 million post. There’s usually not a lot of precision or deep analysis here. The more you raise, the higher your valuation, and the higher the expectations for the next round. Don’t raise more than you need just because you can, but know that it’s kind of how it works at these stages…

Relationships Are the Real Leverage

Maybe the most obvious, and most important, point of all: relationships matter.

If your business isn’t growing like crazy, relationships are what get you the meeting, and the term sheet. VCs are just people. They back people they know, trust, and have seen in action. That’s why I always tell founders to start building relationships long before they need capital. Offer to help. Share your work. Join a portfolio company and build your reputation that way. That’s how you earn the benefit of the doubt when the time comes.

In my own journey with Equals, a lot of our fundraising success was rooted in the relationships I’d built while at Intercom. I wasn’t pitching to strangers. I was calling people who already knew the quality of my work. That changes everything.

Final Thought

None of this guarantees a great raise. But it gives you a much better shot.
And at the very least, it puts you in control of the narrative. Which is the whole game.

Let me know if you want help pitching.
Or just a texting buddy. I’ve been there.