Module 4 — Running the Process · Lesson 4.1
Outreach and Introductions as a Pipeline
Run investors in parallel, by stage, against a deadline
What you'll learn
- Define the stages of an investor pipeline and what moves an investor between them
- Run outreach in parallel, prioritised by expected value, within a bounded time
- Earn warm introductions and write first messages that get answered
- Design follow-up sequences that stop when an investor replies and respect opt-outs
Raises rarely fail with a single no; they fail by drift. A founder sends a few emails, takes the meetings that come, waits for answers, follows up when they remember, and three months later is still 'in conversations'. The cure is to run the raise as a pipeline: every investor is at a known stage, every stage has a next action and a date, and the whole process has a deadline. That structure is not bureaucracy. It is what lets you tell, in week three, whether the round will close.
Parallel, prioritised and bounded
Paul Graham's 2013 essay on raising money, written from years of watching Y Combinator companies, is still the clearest statement of how to run the process. Talk to investors in parallel rather than one after another, prioritising those most likely to say yes and to invest the most — a breadth-first search, as he puts it, weighted by expected value. Treat fundraising as a bounded phase, because a startup cannot endure that level of distraction for long, and keep the company growing while you raise; have one founder carry most of the load.
He also describes the dynamic that makes parallelism matter. Investor interest follows other investors' interest: once some commit, it becomes increasingly easy to get more to. Serial outreach throws that away, because each investor sees a round that nobody else is in.
In pipeline terms: release investors in tranches (Lesson 3.4), move every investor in the tranche forward at the same time, and set a target date for first meetings and a later one for decisions. Investors who cannot meet inside the window are not a priority this round.
Stages, statuses and next steps
Define the stages before the first email, and make each one a fact about the investor rather than a feeling. A workable set: Researched, Intro requested, Contacted, Replied, First meeting, Partner meeting, Diligence, Term sheet, Committed, Passed. Each stage has an exit condition — an introduction made, a reply received, a meeting held — and an owner for the next action.
Two disciplines make the pipeline useful. Every investor has a next step with a date; an investor with no next step is a stalled one. And every stage has a time limit after which it is stale — an introduction that has not produced a reply in a week needs a nudge, a diligence stage with no questions in two weeks needs a call. The stale list, reviewed daily, is the to-do list for the raise.
Be precise about the difference between a stage and a relationship. The same angel can be warm in general and Passed on this round; your pipeline tracks the round.
Introductions and first messages
The deal-flow evidence from Lesson 1.1 is the reason to work for introductions: in the 2016 survey of venture capitalists by Gompers and co-authors, networks, investor referrals and portfolio-company referrals together accounted for well over half of deals, and inbound from management for about 10 percent. Graham's advice is to raise first from leads you get yourself, and he notes that the best introductions often come from investors who have just committed — another reason to run in parallel.
An introduction is a favour; make it easy. Send the introducer a short, forwardable note: the one sentence from Lesson 3.1, why this investor specifically (their thesis, a portfolio company, something they wrote), what you are raising, and a link to the deck. The investor reads that note before anything else.
Cold outreach still works for some investors, especially those who publish a thesis and invite it. The same rules apply: short, specific to them, one clear ask. Personalisation must be true. A message that congratulates someone on the wrong round, or quotes a post a namesake wrote, is worse than no personalisation at all — and for a regulated firm, a false statement in a solicitation is a compliance problem, not just an embarrassment.
Follow-up, opt-outs and the solicitation line
Busy investors miss first messages, and founders mid-raise forget follow-ups. A sequence — a first message and two or three spaced follow-ups — fixes that, on two conditions. It must stop the moment the investor replies, because a scheduled 'just bumping this' arriving after a 'yes, let's talk' looks careless. And it must honour a request to stop, at once and for good.
One legal line runs through all of this. In a Rule 506(b) round, the issuer may not use general solicitation, and under Rule 152 must have a reasonable belief for each purchaser that they were not solicited through general solicitation or that a substantive relationship existed before the offering began. Individual, targeted outreach to investors you have a basis for approaching is the ordinary way 506(b) rounds are raised; mass outreach to people you know nothing about, or public posts about the offering, start to look like general solicitation. Where the line falls on your facts is a question for counsel before the campaign, not after. In a 506(c) round, general solicitation is allowed, but every purchaser must be verified as accredited.
Run the outreach from the round's deal
- 1
Track each investor's stage on the round
On the deal in /deals, each investor contact carries a per-deal status (free text such as Contacted, Soft-circled, Committed, Passed), a next step and its due date, and a contact-level relationship such as Warm or Cold. The same investor can be at different statuses on different deals.
- 2
Set stale-after days and read the brief
In Manage stages, give each stage a Stale after value. The Follow-ups due brief above the board, and the agent's list_stale_deals, surface what has crossed its threshold — your daily to-do list for the raise.
- 3
Build a cadence that stops on reply
Define a cadence (create_deal_cadence, or Manage cadences) — ordered steps a number of days apart. Enrollment arms outbound mail from your own mailbox, so the agent confirms with you first; a reply from the investor cancels the remaining steps, and an opt-out or bounce suppresses the address. New cadences include an unsubscribe line by default.
- 4
Or run the whole tranche as a campaign
start_investor_campaign ranks investors, releases the next tranche, picks the warmest person with an email at each firm (then the most senior), links them to the deal and enrolls them. It returns a sourcing-gap list of firms with nobody to write to. Automatic release of later tranches is off unless you turn it on. Before personalised steps, research_contact stores only facts that pass a fact-check — and costs credits.
Is the pipeline moving?
- Stage conversion
- Share of investors moving from each stage to the next — contacted to replied, replied to first meeting, and so on — by tranche.
- Healthy signal: Watch where it drops, not the absolute level. The stage with the steepest drop is where to work next.
- Investors without a dated next step
- Count of active investors on the round with no next step or an overdue one.
- Healthy signal: Zero at the end of each day — a Kavanah operating suggestion.
- Days into the raise
- Days since the first tranche was released, against your planned window.
- Healthy signal: Set the window before you start. A raise that drifts past it needs a decision — new tranche, new story or a pause — not more of the same.
Key takeaways
- ·Run investors in parallel, prioritised by expected value, inside a bounded window.
- ·Define stages with exit conditions; every investor has a dated next step and a stale threshold.
- ·Work for introductions — networked deal flow dominates — and make them easy to forward.
- ·Follow-up sequences must stop on reply and honour opt-outs; in a 506(b) round, targeted outreach must not become general solicitation.
Outreach produces meetings. The next lesson is about what happens in them.
Sources
- 1.How to Raise Money
Paul Graham · paulgraham.com (September 2013) · 2013
Talk to investors in parallel, prioritised by expected value; fundraising as a bounded phase; investor interest follows other investors' commitments; raise first from leads you get yourself.
- 2.How Do Venture Capitalists Make Decisions?
Paul Gompers, William Gornall, Steven N. Kaplan, Ilya A. Strebulaev · NBER Working Paper 22587 · 2016
Deal-flow sources: networks, investor and portfolio referrals well over half of deals; about 10% inbound from management.
- 3.17 CFR 230.152 — General principle of integration
U.S. Securities and Exchange Commission (eCFR) · Electronic Code of Federal Regulations, up to date as of October 21, 2026 · 2026
For an offering prohibiting general solicitation, a reasonable belief that each purchaser was not solicited through general solicitation or had a substantive relationship with the issuer before the offering commenced.
- 4.17 CFR 230.502 — General conditions to be met
U.S. Securities and Exchange Commission (eCFR) · Electronic Code of Federal Regulations, up to date as of October 21, 2026 · 2026
Rule 502(c)'s prohibition of general solicitation and general advertising.