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In short: zero replies usually means you're emailing the wrong people, not writing the wrong words. Do your first 100 outreaches by hand, target the right person and company, write a short email about their problem with one clear ask, follow up, and borrow your customers' own words.

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🎙️ Y Combinator · 👤 Christina Gilbert · ⏱️ 13 min · 📅 September 12, 2026 · ▶️ Watch on YouTube

🧠 Key ideas

  1. Start manual before you automate. A thousand automated emails with zero replies teach you nothing: was it the message, the targeting, the subject line or deliverability? Do at least 100 outreaches by hand first.
  2. Targeting beats perfect messaging. A founder selling infrastructure to engineering leaders was emailing devrel, go-to-market and customer success managers: "Those wrong job titles were never going to buy, no matter how good your email was."
  3. Find the right titles and companies. Look at who pushed, signed and paid in your deals; with no customers yet, ask who has the most to gain or to lose. Check companies one by one: list tools return lookalikes.
  4. Watch for intent signals. Job postings and company growth reveal urgency, like compensation software being needed around the 100-employee mark.
  5. Write about their problem in five to eight sentences. Executives care about their quarterly target, not your features. One sentence on the product, one line of credibility, and a specific ask like "Got 20 minutes to hop on a call this week?"
  6. Subject line and LinkedIn profile are your first impression. Creative subject lines can win ("broken agents" beat "better agents for every workflow"); a photo, a clear banner and mutual connections raise acceptance.
  7. Debug reply rates in order. Person, company, subject line, message, materials, deliverability. If all six look fine and replies are still zero, it may be a product-market fit problem.
  8. Follow up, reply fast, block time. Follow up two to four times, end with a "breakup" email, answer like a heat-seeking missile because time kills deals, and put outbound on your calendar.

📑 Chapters

00:00 · Why replies are close to zero

00:38 · Start manual before you automate

01:25 · Targeting beats perfect messaging

03:07 · Picking the right companies and intent signals

04:25 · Craft a message worth reading

06:00 · A cold email that works

07:19 · Subject lines and LinkedIn profile

08:47 · What your reply rates are telling you