As someone who works with founders, partners, and investors daily, my LinkedIn inbox and DM’s fill up fast. And yet, most messages go unanswered. Not because I don’t want to help, but because the outreach often misses the mark.
TL;DR: If your first few sentences don’t state who you are, what you want, and why it’s relevant to me, the conversation is already over. Be deliberate, do your homework, and make a clear ask.
Be deliberate. Be specific. Be brief.
Here’s what strong outreach does in under 50 words:
- Context: Who you are + one line on what you do.
- Relevance: Why this is specifically aligned with my remit.
- Intent: The precise outcome you’re seeking.
- CTA: A concrete, low-friction next step.
If any of those are missing, I’m guessing and I don’t have time to guess.
The white elephant: vague outreach wastes everyone’s time
1. Vague intentions
The classic opener: “Let’s explore possible synergies.”
The problem? “Synergies” could mean a hundred different things. Without clarity, I’m left guessing, and guessing isn’t a good use of anyone’s time.
Instead: Be explicit. Are you referring to GTM distribution, ecosystem access, technical integration, fundraising, or content collaborations? Define the collaboration and propose what it might look like.
State what kind of collaboration:
- GTM/Distribution: Co-marketing, co-hosted workshops/AMAs, builder sourcing for a program or launch.
- Program/Acceleration: Joint accelerator or hackathon tracks; selection, mentors, KPIs, timeline.
- Ecosystem Access: Warm intros (MMs, launchpads, exchanges), listing readiness support, liquidity design.
- Technical/Infra: Integrations, grants, node/provider credits, tooling that reduces builder time-to-value.
- Events/Content: Panels, thought leadership, curriculum modules with clear topics and dates.
Setting the agenda right
2. Calls with no purpose
Another frequent one: “Can we hop on a quick call?”
But what’s the purpose of the call? What will we decide at the end of 30 minutes? Without an agenda or objective, the call risks being a black hole.
Instead: Share the reason. “I’d like 20 minutes to discuss (the purpose)” and share materials beforehand. That level of clarity makes it easy to say yes.If you can’t write the 3-bullet agenda, you don’t need a call yet.
Raising a round? Do the homework first.
3. Fundraising without context
Simply saying “We’re raising a round” is not enough.
Fundraising outreach without details forces the recipient to dig for basic information: What stage? What size? What valuation? Why is this relevant to our thesis?
Instead: Include round type and size, valuation/FDV range, % committed, timeline, and why you believe there’s alignment. This shows respect for the recipient’s time and increases your chance of a meaningful response.
If you’re fundraising, get straight to the point:
- Round & terms: Round type/size, valuation/FDV range, % committed, timing.
- Why us: Show alignment with our thesis (don’t make me infer it).
- Proof: Traction (users, revenue, on-chain metrics), edge (why now/why you), and the specific help you want.
If there’s no thesis fit, say so and ask for one thing you actually need (e.g., “warm intro to X,” “feedback on token design pitfall Y”). Respect is reciprocal.
How to stand out in a sea of messages
4. Copy-paste messages
When a message looks like it was blasted out to 100 people, it probably was. These are easy to spot, and just as easy to ignore.
Instead: Reference something specific about the recipient’s work. It doesn’t take much—one sentence is enough to show your outreach is intentional.
- Lead with my world, not yours. Mention one relevant line from my work (e.g., Post-Web/agentic internet; DeAI, RWA, DePIN, DeFi; launch-readiness). Prove you didn’t BCC the planet.
- Front-load the value. The first 50 words should tell me why this matters.
- Make it easy to say yes. Offer 2–3 crisp options (pilot scope, dates, success metric) and a short doc link. No attachments required to understand the ask.
- Choose one ask. “Coffee + collab + intro + investment” in one message is a guaranteed no.
The first-50-words rule (use this checklist)
Before you hit send, can your opener answer all of these?
- Who you are (name, role, credible context)
- What you do (one sentence)
- Why me (explicit tie to my remit/thesis)
- What you want (single, concrete ask)
- What success looks like (one metric or decision)
If not, rewrite it.
Common reasons I don’t reply
- “Pick your brain?” with no agenda.
- “Explore synergies?” with no clarity.
- Fundraising with zero thesis fit or missing basics (round size, valuation/FDV, timing).
- Seven paragraphs with no ask.
- Attachments only; no summary.
- Calendly-first without consent or context.
A simple message structure you can reuse
- Subject/first line: Specific purpose + outcome
- Line 1–2 (context + relevance): Who you are + why me.
- Line 3 (intent): The one thing you want to do.
- Line 4 (proof/cred): One result, metric, or social proof.
- Line 5 (CTA): The smallest next step that moves us forward.
Total: 60–100 words. No fluff.
Respect the reader, increase your odds
I’m not the only one feeling this. Most investors and partners I know are drowning in vague DMs. The people you want to reach are busy and clarity is kindness. When you’re deliberate, sweet, and straight to the point, you signal you’ll be equally clear to work with.
I want to say yes more often. Help me help you. Lead with intent, speak in specifics, and make your first 50 words count.
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The post Why Most Outreach Fails (and How to Get it Right) appeared first on Outlier Ventures.
