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Sep 12, 2024 · 32m · y-combinator

How To Convert Customers With Cold Emails | Startup School · Y Combinator

Aaron Epstein · 29m spoken
0:00 / 0:00
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In this Y Combinator Startup School lecture, Group Partner Aaron Epstein presents a comprehensive guide on writing high-converting cold emails and managing outbound sales funnels for early-stage startups. He shares practical techniques covering sales conversion math, inbox optimization, core copywriting principles, and real-world email critiques.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →

The partners as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 The partners pushing back 0.0
05100:0010:0020:0030:000:00–5:37 · The partners as informed peer 0/10 Opening Title Card: Cold Emails That Convert This is a solo educational presentation by Aaron Epstein explaining the mechanics of cold outreach and conversion funnels, with no host interaction.5:37–9:51 · The partners as informed peer 0/10 How to Increase Cold Email Open Rates Epstein continues his solo lecture detailing tactical methods for boosting open rates, lead qualification, and personal branding without host dialogue.9:51–22:11 · The partners as informed peer 0/10 7 Principles of Effective Cold Email Copy Epstein presents the seven core copywriting principles for cold emails in a structured monologue format with no host involvement.22:11–30:59 · The partners as informed peer 0/10 Analyzing Bad and Good Cold Email Examples Epstein concludes his presentation by deconstructing real-world good and bad email examples in a solo monologue format.0:00–5:37 · Guest teaching 0/10 Opening Title Card: Cold Emails That Convert This is a solo educational presentation by Aaron Epstein explaining the mechanics of cold outreach and conversion funnels, with no host interaction.5:37–9:51 · Guest teaching 0/10 How to Increase Cold Email Open Rates Epstein continues his solo lecture detailing tactical methods for boosting open rates, lead qualification, and personal branding without host dialogue.9:51–22:11 · Guest teaching 0/10 7 Principles of Effective Cold Email Copy Epstein presents the seven core copywriting principles for cold emails in a structured monologue format with no host involvement.22:11–30:59 · Guest teaching 0/10 Analyzing Bad and Good Cold Email Examples Epstein concludes his presentation by deconstructing real-world good and bad email examples in a solo monologue format.0:00–5:37 · Guest disagreement 0/10 Opening Title Card: Cold Emails That Convert This is a solo educational presentation by Aaron Epstein explaining the mechanics of cold outreach and conversion funnels, with no host interaction.5:37–9:51 · Guest disagreement 0/10 How to Increase Cold Email Open Rates Epstein continues his solo lecture detailing tactical methods for boosting open rates, lead qualification, and personal branding without host dialogue.9:51–22:11 · Guest disagreement 0/10 7 Principles of Effective Cold Email Copy Epstein presents the seven core copywriting principles for cold emails in a structured monologue format with no host involvement.22:11–30:59 · Guest disagreement 0/10 Analyzing Bad and Good Cold Email Examples Epstein concludes his presentation by deconstructing real-world good and bad email examples in a solo monologue format.0:00–5:37 · The partners pushing back 0/10 Opening Title Card: Cold Emails That Convert This is a solo educational presentation by Aaron Epstein explaining the mechanics of cold outreach and conversion funnels, with no host interaction.5:37–9:51 · The partners pushing back 0/10 How to Increase Cold Email Open Rates Epstein continues his solo lecture detailing tactical methods for boosting open rates, lead qualification, and personal branding without host dialogue.9:51–22:11 · The partners pushing back 0/10 7 Principles of Effective Cold Email Copy Epstein presents the seven core copywriting principles for cold emails in a structured monologue format with no host involvement.22:11–30:59 · The partners pushing back 0/10 Analyzing Bad and Good Cold Email Examples Epstein concludes his presentation by deconstructing real-world good and bad email examples in a solo monologue format.

speaking balance: gold is the partners, purple is the guest (3 minute bins)

0:00 · the partners 0% · guest 100%0:00 · the partners 0% · guest 100%3:00 · the partners 0% · guest 100%3:00 · the partners 0% · guest 100%6:00 · the partners 0% · guest 100%6:00 · the partners 0% · guest 100%9:00 · the partners 0% · guest 100%9:00 · the partners 0% · guest 100%12:00 · the partners 0% · guest 100%12:00 · the partners 0% · guest 100%15:00 · the partners 0% · guest 100%15:00 · the partners 0% · guest 100%18:00 · the partners 0% · guest 100%18:00 · the partners 0% · guest 100%21:00 · the partners 0% · guest 100%21:00 · the partners 0% · guest 100%24:00 · the partners 0% · guest 100%24:00 · the partners 0% · guest 100%27:00 · the partners 0% · guest 100%27:00 · the partners 0% · guest 100%30:00 · the partners 0% · guest 100%30:00 · the partners 0% · guest 100%
Sharpest disagreement ▶ 28:15 Firm rejection of premature automation

In a solo lecture with zero interpersonal conflict, Epstein emphatically insists that founders must write emails manually and not automate early on.

 Hardest push from the partners ▶ 0:00 No host pushback present

This is a direct-to-camera educational monologue without host questioning or pushback.

 Biggest teaching moment ▶ 2:15 Explaining the 800-email-to-1-customer funnel math

Epstein breaks down the mathematical reality of B2B cold outreach conversion rates for founders.

 The partners hold their own ▶ 0:00 No host intervention

There is no host participation in this solo presentation format.
the scores for every segment, with the reasoning behind each
ChapterTopicThe partners as informed peerGuest teachingGuest disagreementThe partners pushing backWhy
Opening Title Card: Cold Emails That Convert 0000 This is a solo educational presentation by Aaron Epstein explaining the mechanics of cold outreach and conversion funnels, with no host interaction.
How to Increase Cold Email Open Rates 0000 Epstein continues his solo lecture detailing tactical methods for boosting open rates, lead qualification, and personal branding without host dialogue.
7 Principles of Effective Cold Email Copy 0000 Epstein presents the seven core copywriting principles for cold emails in a structured monologue format with no host involvement.
Analyzing Bad and Good Cold Email Examples 0000 Epstein concludes his presentation by deconstructing real-world good and bad email examples in a solo monologue format.

Statements from this episode (9)

Insight
Epstein: Warm Intros Yield 2x to 3x Cold Email Conversion Rates
“This is the most effective way to get people to respond to emails that you're sending to them. And you're going to have a conversion rate two to three times what you would get if you were just sending a regular cold email.”
Aaron Epstein Sep 12, 2024 ▶ 0:24
Insight
Epstein: Founders Must Write Cold Emails Manually Before Automating
“And you should plan to start this writing these emails manually and personalized, doing it yourself, not starting with automation. You have to do it manually first so that you can learn and figure out what works so that you can then start to scale the process …”
Aaron Epstein Sep 12, 2024 ▶ 4:00
Insight
Epstein: Cold Email Conversion Rates Inevitably Decline at Scale
“But one thing that's important to note is that conversion rates will decrease as you scale. So if you're starting out in the early days and you're writing these emails manually and you're not getting good conversion rates, then that's something you should fix …”
Aaron Epstein Sep 12, 2024 ▶ 5:10
Insight
Epstein: Cold email is generally a better outreach channel than LinkedIn
“I found that the ideal channels to contact are email is usually better. LinkedIn is usually worse.”
Aaron Epstein Sep 12, 2024 ▶ 7:05
Insight
Epstein: Targeting uncommon commonalities maximizes cold outreach conversion
“You want to try to find the uncommon commonalities with the people that you're reaching out to. Now, uncommon commonalities are things that you have uniquely in common with somebody else. Things that are not obvious to have in common with other people... You h…”
Aaron Epstein Sep 12, 2024 ▶ 15:02
Insight
Epstein: Copying user phrasing is the best language for sales outreach
“The language that your users use to describe you is almost certainly the same language that's going to resonate with other people just like them.”
Aaron Epstein Sep 12, 2024 ▶ 19:08
Insight
Epstein: Cold emails should never explain how contact information was found
“You don't need to tell somebody how you found their contact information. That's relevant to you, not relevant to them.”
Aaron Epstein Sep 12, 2024 ▶ 24:54
Disclosure
Epstein: Creative Market recruited launch sellers via templated 'exclusive' emails
“So what's interesting about this email is this is entirely a templated email, except for the person's first name and the special URL that they need to come and sign up early. But I use a lot of tricks throughout in order to make it feel very special and person…”
Aaron Epstein Sep 12, 2024 ▶ 28:16
Insight
Epstein: Cold emails perform far better from founders than from sales reps
“You, the founder, should be sending these. People are going to take them way more seriously when it comes from the founders or the CEO Much more so than if it comes from some account executive or some intern or some other automated process that you set up here…”
Aaron Epstein Sep 12, 2024 ▶ 31:50
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