Most founders treat fundraising like a sprint. They wait until they need the money, scramble to build a target list, cold-blast their way to an intro, and wonder why it's taking so long.
The founders who close rounds faster aren't better pitchers. They're better relationship managers: the ones who started before they were ready, showed up before they had an ask, and by the time they were actually raising, had already done most of the work.
That's the premise behind The Investor Flywheel, Goodword's recent workshop hosted by Caroline Dell, Co-founder and CEO, and Alex Chung, Head of Growth and former investor. Together, they walked a room full of founders through the playbook, including the intros that failed, the rounds that got stuck, and what finally broke through.
Here's what they shared, turned into a framework you can use to unlock your fundraise.
Start Raising Before You're Raising
The single biggest unlock in Caroline's fundraising story had nothing to do with her pitch deck. It was a year of quarterly update emails she sent to ~40 potential investors before she ever opened a round.
By the time she went out to raise her institutional seed, her future lead investor didn't feel like a cold contact. She'd been along for the ride — watching the company evolve from idea, to market validation, to prototype, to ready-to-build. The feedback was simple: I'm in. I feel like I've been on this journey.
That's the flywheel in action. The warm path you're trying to engineer when you're raising already exists — but only if you've been building it.
Most founders discover this too late because their approach to relationship management is reactive. They remember people when they need them, not before. The founders who run this well treat it more like portfolio management: a living list of potential investors, interactions logged over time, relationships tracked — not just titles and fund names.
What to do now:
Build your target list before you have any immediate need. Start with 30–50 names. Research their thesis, check for investments in your space or adjacent ones, and commit to a quarterly update — short, punchy, a few paragraphs at most. The goal isn't necessarily to impress them, it's to make them feel like they're already part of your story.
Then do a network audit. Which investors are already in your first-degree LinkedIn network? Who in your extended circle knows them, and how well? Which of those contacts are founders in a VC's portfolio — your highest-value potential introductors? Who have you been out of touch with for too long?
💡 Tactical Tip: Ask people you meet at events: Can I add you to my quarterly update list? It's a low-pressure way to create a touchpoint that compounds, and the warm introduction you'll need six months from now often starts with exactly that kind of conversation today.
The Warm Intro Is an Art, Not a Favor
Warm introductions convert at a meaningfully higher rate than cold outreach (58% or higher, compared to just 1–5% for cold email), which is not a surprise. But most founders still treat asking for them as something awkward and hard to systematize, when it doesn't have to be.
Caroline shared the story of how she finally got a meeting with an early-stage VC fund after her first attempt through a mutual connection resulted in an automated "fill out the form" response. The breakthrough came when she caught up with someone in her network who turned out to be a small LP in the fund. Within 48 hours of that conversation, she had a meeting.
The lesson isn't about finding the perfect path — it's staying in touch with enough people, mapping your network, and getting comfortable asking for help.
The forwardable blurb formula:
When you identify the right connector, don't make them do the work: write the email for them. A good forwardable has three parts:
- A one-sentence context line (who you are and what you're building)
- A specific reason this introduction makes sense (why that fund based on their thesis)
- A clear, easy ask
Caroline illustrated this with a story from her own experience on the receiving end: a founder sent her a short, targeted list of funds and asked if she could help with any of them. She flagged the ones she could and asked for a separate forwardable for each — one per fund, not a catch-all. All she had to do was hit forward. That's the best practice.
A few things to know about introductors:
Founders in a VC's portfolio tend to be the most effective introducers, since they've already built trust with that investor. Other VCs can be valuable connectors too, particularly if they invest at a different stage than you're raising — a Series A investor, for example, can be a natural bridge to seed funds. The main thing to avoid is putting your connector in an awkward position — if the logic of the introduction isn't obvious, it probably isn't the right ask.
And don't get discouraged if an intro doesn't land — timing, relationships, and inbox chaos can all get in the way. Caroline mentioned one instance where the same VC who didn't respond to a first intro responded immediately to a second one a month later from a different person — so it's always worth trying again through a different path.
Build the Line, Not the Dot
Alex put it simply: when she was a VC, she was investing in lines, not dots. A single pitch is a dot — a snapshot in time. A series of updates, progress signals, and relationship moments over months or years is a line, and investors want to back founders they've been watching evolve.
The investor update email is the tool that draws that line.
Here's what makes it work:
- Cadence: Quarterly is enough. More frequent if you're actively raising.
- Length: Short — 3–5 paragraphs or bullet points, not a newsletter.
- Content: What's changed since last time? Key milestones, growth metrics, team updates, what you're focused on next.
- Tone: Warm and direct. You're bringing people along, not filing a report.
The goal isn't to impress everyone on the list every quarter; it's to make sure that when you do reach out with an ask, no one feels like they're hearing from you for the first time. This applies to angels, advisors, and founder friends too, not just institutional VCs.
The Ask Is Part of the Relationship
An attendee asked a question that comes up a lot: how do you know when it's okay to ask for a favor, and does making asks deplete the relationship over time?
Caroline's take was that when you've kept people genuinely in the loop, the ask often lands as an opportunity for them to be part of something, not a tax on the relationship. The update email (or social posts if you're building in public) is what creates that dynamic: when someone has been following your journey, asking them for three introductions feels like a natural next step, not a cold reach.
Closing the loop matters just as much. If someone makes an introduction for you, follow up and tell them what happened. That simple gesture is what turns a one-time favor into an ongoing alliance.
When You're Stuck in the Middle of a Raise
One attendee asked what happens when you've been at it for months and the round isn't closing — a feeling most founders in a raise know well.
Caroline's answer came from experience: like many founders, Goodword's raise took longer than anticipated, with momentum stalling before eventually coming together. The shift that helped was moving into a closing mentality — and leaning into the FOMO that naturally builds when a round is nearly full.
"I would highly recommend going back out to everyone and communicating: it's closing, you're in or you're out."
It's also worth remembering that fundraising is a volume game. Caroline estimated they spoke to close to 100 funds and had 250 conversations over the course of their raise. The feeling of running out of options is almost always an illusion. As they say in sales, "pipeline cures all." And if the same friction keeps coming up in first calls, take a few hours to refresh your materials rather than pushing through with something that isn't landing.
The Bigger Picture
The frameworks from this workshop are only useful if they're built on something genuine. The founders who successfully raise tend to be the same ones who've been showing up for their networks consistently, long before they needed anything. Goodword is here to help you build that foundation and turn your network into your greatest advantage.
Want to put these frameworks to work? Goodword is the networking copilot that helps you remember context, surface the right connections, and unlock the power of your network. Sign up for early access.
