Cold outreach for founders
Cold outreach that doesn’t feel cold.Written like you. Sent for you.
Four guides to finding your first customers, built on what YC partners and founders say works. Each one comes with a River playbook that does the work in your voice.
Six rules every guide comes back to.
Send the first hundred yourself.
It’s how you learn who has the problem and what gets a reply. Christina Gilbert, a YC Visiting Partner, recommends your first 100 outreaches by hand.
Start with people you know.
“Customers one through three almost always come from your personal network,” says Max Kolysh, a YC Visiting Partner. Ask for intros before you write to strangers.
Who you write to beats what you write.
A sharp message to the wrong person gets nothing. Aaron Epstein, a YC partner, puts better targeting first, so fix the list before you touch the copy.
About them, under 75 words, one ask.
Kolysh’s limit is 75 words. In Gong’s analysis of cold emails, pitching cut reply rates by as much as 57%. Their problem, not your product.
Ask for a conversation, not a sale.
“Your job on the first call is not to sell your product,” says Pete Koomen, a YC partner and Optimizely’s co-founder. Ask for 15 minutes and listen.
Follow up three or four times.
Most people don’t answer the first message. Kolysh’s rule: “Something like three or four times over a couple weeks is perfect.” Add something new each time.
Or let River run it.
Each guide has its own River playbook. Tell it who you want to reach: River reads what you’ve built, finds the people, writes every message in your voice and shows you three samples before anything goes out.
How it works
Founder
Start a playbook and River works through it with you in the chat.
Run my cold outreach playbook.
- What you’re reaching out about
- A 15-minute call about 3 a.m. pages
- Who first
- Engineering managers hiring an SRE, new VPs of Engineering
- Where
- Email, LinkedIn
24 people fit, each with a reason to write now. The two you know get warm intros.
Three samples, starting with Maya:
Hi Maya, saw Larkspur is hiring a second SRE. Teams that size often get paged at 3 a.m. for alerts that could wait. Hushpage holds those until morning. Worth 15 minutes next week? Sam
Ready to reach these 24 people?
Emails and LinkedIn invites from your accounts, with two follow-ups. I’ll answer anyone who replies, and ask you only if a reply needs something new.
Ask anything, or describe what you want done
Go where your buyers spend their day.
Kolysh starts with one question: “Where does your target customer actually spend their time?” Most founders end up using two of these.
| Channel | Best for | Watch out for |
|---|---|---|
| Most business buyers. The most room to say something useful in a few lines. | Spam rules: check every address and keep each inbox to a low daily number. | |
| Buyers who work on LinkedIn: sales, recruiting, operations, other founders. | About 100 invites a week, and its rules don’t allow software to send for you (as of October 2026). | |
| X | Developers, AI builders, founders and investors who talk about their work in public. | Cold DMs wait in a requests folder, capped at 7 a day free or 35 on Premium (as of October 2026). |
| In person | Buyers who don’t sit at a desk. Kolysh tells of a founder who closed more at one trade show in three days than in three months of cold email. | It doesn’t scale, which is fine for your first ten customers. |
A few questions.
Is cold outreach still worth it?
Yes, when each message is written for one person with a real reason to write. As Epstein puts it, “most cold emails are actually terrible, so the bar is really low for you to stand out.” What no longer works is one message sent to thousands.
Which channel should I start with?
Your own network first, then wherever your buyers spend their day: email for most business software, LinkedIn where you share connections, X for developers and founders, and in person for people who don’t work at a desk.
How many messages should I send?
Enough to learn: two to four groups of 100 to 200 people, each with three or four follow-ups, then read who replied. The Prospecting guide shows how to size and read a test.
Will River send anything without asking?
No. River shows you its plan and three sample messages and waits for your go-ahead, and you can tell it to draft only. On LinkedIn and X it can get each message ready for you to press Send.
Is cold outreach legal?
Generally, if you follow the rules. In the US, CAN-SPAM covers business email too: an honest sender and subject line, your postal address and an opt-out you honor. The EU, UK and Canada are stricter, so check before writing there. This isn’t legal advice.
Start with who to reach.
Most outreach fails on the list, not the words. Get the list right first, then pick your channel.