Article VIII

I get asked often for advice on venture fundraising. Although I am most comfortable helping other founders with what they need for successful raises, I do have experience, having helped lead four separate businesses through multi-million dollar priced rounds.

If you’re a serial founder you know what to do. If you’re doing a staged real raise for the first time, it can be daunting. I wrote up ten steps that I thought would be helpful if I had a time-machine to give myself a few years ago.

Please use what applies to your stage and your round. Not every step lands the same way for a pre-seed angel round as it does for an institutional seed. Read it as a set of instincts, less as a script. It’s all based on my personal experience, I hope it helps you.

1. Work backward from 18-24 months.

Decide the number you need before a single conversation happens. Raise for enough runway that you're never fundraising from a position of panic. The standard is 18 months minimum, with 6 of those months held as a buffer so you're not back out raising the day the cash gets tight.

Then reverse-engineer the number from actual use of proceeds: payroll for the team you need, the specific product or go-to-market milestones that number buys you, and what the next round's story becomes because of it. "We need money" is not a number. "This gets us to the milestone that makes the next raise easy" is.

FROM THE FIELD: One client's whole round-sizing conversation came down to what does $5M actually buy, how much payroll, how many months, what does it prove, versus what a larger check would additionally unlock. Investors fund a plan, not a feeling.

2. Build the narrative in order: credentials, then the elephant in the room, then the vision.

The instinct is to open with the big vision. Don't. Investors are often pattern-matching for risk before they're pattern-matching for upside. Open by first establishing why you're the right people to be doing this: track record, relevant scars, prior successes/exits or what you built that is relevant. Then name the obvious objections to yourself before they raise it.

Only after that do you earn the room to paint the scale of the opportunity. A founder who names their own weak point first can read as more in control of the story; a founder who waits to get asked reads as caught off guard.

FROM THE FIELD: "Credentialize us, then jump straight to the elephant in the room" is a near-verbatim structure we've used going into some of the best pitch calls. Say what they're already thinking before they get to ask it.

3. Never lead with the deck. Lead with the conversation.

Don't send material before a first call, and don't open the call by screen-sharing a 30-slide deck. Open with a couple of questions, deliver a tight three-minute verbal version of the thesis, and only share your screen selectively, a chart here, a product shot there, then keep talking.

This does two things: it keeps you in control of the pacing instead of the deck controlling it, and it creates the sense that there's real material behind the conversation that they haven't seen yet. Decide after the call, not before, whether and what you send as a leave-behind.

Build the leave-behind like it matters, because it's doing work when you're not in the room: it gets forwarded internally, and its quality is read as a direct proxy for the quality of the company. A sloppy deck undercuts a great pitch every time.

FROM THE FIELD: We've watched a forwarded deck turn into a partner-level "we need to back this" within two hours, with zero additional conversation. The deck alone did the convincing once it was in front of the right second reader with the warm intro from the first partner.

4. Do reps before the reps that count, and grade every single one.

Treat your first several investor calls as practice, and be honest about it internally. After every call, write down what worked, what confused them, what question caught you flat-footed, and a rough score. Patterns show up fast, usually by call four or five you'll see the same objection twice.

Before you're in market, run a mock pitch with a friendly, sophisticated set of eyes, someone who'll poke holes without an investment decision riding on it. Stress-test the narrative against people who care about you succeeding, not people you're trying to close. Practice makes perfect and you’re going to want to practice.

FROM THE FIELD: One team logged each single VC conversation with a score out of 10 and a short debrief, what landed, what didn't, what to sharpen, treating the raise itself as the practice environment. By call six or seven, the same two questions kept surfacing, and the pitch got rebuilt around answering them before they were asked. We needed those 6-7 reps up front to find what to fix.

5. Know exactly which kind of investor is in front of you, and size the ask to fit them.

A traditional early-stage fund and a multi-stage growth firm are not the same conversation, and asking for the wrong amount from the wrong type of investor kills momentum before it starts. A round that's too big reads as a stretch to a seed lead; the same round can read as too small to be worth a multi-stage firm's time.

Learn each investor's real check-size range, whether they lead or only follow, and whether they can flex bigger for the right deal, and ask accordingly on the first call, not the third.

FROM THE FIELD: "We're raising six" was a deliberately different number depending on who was across the table: sized down for a traditional seed lead, sized up when the conversation was with a multi-stage firm that doesn't move for a small check.

6. Go through a warm lead.

The highest-probability path is a warm introduction from someone the investor already trusts: a portfolio founder, a co-investor, a friendly operator.

This means your job for weeks before you're "in market" is mapping who already knows the people you want to reach, and asking directly for the intro. It's not beneath you and it's not annoying, everyone in this business is doing the same thing for something else, all the time.

FROM THE FIELD: Getting into a fund this way works a lot like getting into a club. You don't walk up to the door and hope. You text the friend who's already inside, and they walk you in.

7. Run an actual process, don't let information leak out indefinitely.

An open-ended drip of "just checking in" conversations with no deadline kills urgency. Instead: soft-circle interest first without sharing the deck or data (a teaser, a conversation, a "we're going out soon"), then announce a real process with a tight, explicit timeline: access to the deck and data room for a fixed window, term sheets due by a specific date, a decision shortly after.

A deadline does the work that a hundred more conversations won't. It forces a yes or a no instead of a slow fade.

FROM THE FIELD: A process that's worked repeatedly has been to soft circle, then announce the process, then 7-10 days of data room access, then term sheets due, then a decision within days of that. Everyone in the process knows the clock is running, which is exactly the point.

8. Leverage the deleverage.

The moment you're asking for money, you're structurally the less powerful party in the room. That's just the math of it. The counter is to consciously manufacture leverage anyway: real competing interest, a real deadline, information revealed deliberately rather than all at once.

Don't over-explain and don't hand over everything on the first ask. Show one piece of what you've built, let it land, then show the next piece. Let a real second option (another interested investor, another path) do some of the negotiating for you, honestly, not as a bluff.

FROM THE FIELD: "When you're asking for money you're often de-leveraged, so you have to leverage the deleverage." The practical version of that is as simple as being honest that others are already circling, and letting a real deadline create real pressure instead of asking indefinitely.

9. Expect most rejections to be about proof, not about you, and log why every time.

Seed rounds routinely can take 50-100 investor conversations before a close; a dozen or two "not right now" conversations is normal, not a signal to panic or change the whole pitch. Most passes at this stage trace back to one thing: not enough proof of traction yet, not a flaw in the story.

Track the actual reason behind every single pass. If the same objection shows up three times, that's a real signal and worth addressing head-on in the next version of the pitch. If it's scattered and different every time, that's normal variance. Keep going.

FROM THE FIELD: Across dozens of investor conversations on one raise, the same two or three questions kept resurfacing, not because the pitch was weak but because the proof point those investors needed didn't exist yet. That's useful information, not a verdict on the company.

10. Pick the partner who can write the next check too, and mind the calendar.

The best investor at this stage isn't just the best price. It's the one who can plausibly lead or participate in the next round as well, because a clean path to your Series A is worth more than an extra point of dilution today. Ask directly whether a fund has a growth vehicle or reserves for follow-on.

Build in real lead time: from a strong first call to money actually wired is six to eight weeks at best, rarely faster. Deals also don't close in dead zones. The two weeks around Thanksgiving and the back half of December are close to unworkable; the market reopens in force in mid-to-late January. Plan your outreach to land in the windows when checkbooks are actually open.

FROM THE FIELD: One repeated miss we've seen: optimizing hard for the current round and not asking who at the table can also write the next check. The founders who get this right end up with an inside track on their Series A instead of starting that search from zero.

One last thing

Everything above is craft, not magic. The market ultimately has to say yes, and that's mostly a function of proof, timing, and who you already know.

What you control is showing up prepared, telling the story in the right order, and running the process like a process instead of a hundred loose conversations.

We're glad to be a sounding board on any of this as you go: a deck review, a dry run before a real call, or just a gut check on how a conversation went.

Break a leg,

Little Plains