Why I Stopped Trying to Be Liked: My First Big Lesson in Writing Cold Emails
A few weeks after I joined Caprae, I was assigned to the email team. My job wasn’t to write the entire email, but arguably the most critical part: Customization. This was the hook, the personalized insight designed to catch a founder’s attention.
My first attempts followed a simple logic: be nice. I wrote customizations that were complimentary and safe, praising a company’s recent award or its years in business. I thought the goal was to be liked, to make the owner happy so they would reply.
The customizations were graded weekly, but one week, the feedback came directly from our founder, Kevin. He wasn’t happy. That’s when he explained the two paths of outreach: the ‘Seller-Rockstar’ versus the ‘Buyer-Rockstar.’
Problem with Praise
He noticed that my writing approach “Seller-Rockstar”, while seemingly safe, was likely generating polite but empty responses. My customization hooks were all flattery, designed to get a positive reaction.
In his view, we weren’t starting conversations; we were getting patted on the head before being ignored. This approach positioned us as fans, not peers. He believed that even if we got replies, they would likely be polite dismissals, such as “Thanks for the kind words,” rather than the start of a real dialogue. The assumption was that we were optimizing for likes, not leads.
The Shift: 10 Lovers > 100 Likers
The turning point came when Kevin shared a principle from Airbnb’s CEO, Brian Chesky, that changed my entire approach:
“It’s better to have 10 people love you than 100 who only like you.”
It clicked. We weren’t trying to win a popularity contest. We were trying to find the 10 founders who were serious enough to engage in a real, substantive dialogue. The goal of my customization wasn’t to be liked by everyone; it was to be respected by the right ones.
That was the birth of the “Buyer-Rockstar” approach. No more flattery. The new customizations were direct. They led with a sharp insight about the owner’s market, followed by a bold question that showed we’d done our homework. We stopped acting like admirers and started acting like potential partners.
From Applause to Impact
The goal wasn’t to increase the total number of replies. The hypothesis was that the quality of the replies would change. Instead of polite ‘thanks,’ the aim was to provoke responses like, “That’s an interesting question. How did you arrive at that conclusion?” or “You’re the first person to ask about that specific bottleneck. Let’s talk next week.”
The strategy was to trade polite dismissals for the start of real conversations.
This was my first big lesson at Caprae, and it went far beyond those two sentences. It was an insight into the firm’s entire ethos. We don’t want 100 people to like us; we want 10 to love us, because those are the relationships where real value is built. It’s a philosophy of courage over consensus and substance over style.
It taught me to ask a fundamental question, not just in business, but in any professional endeavor. It also taught me how writing works. I believe this new knowledge is a useful mechanic I can apply to any part of my life, not just my work at Caprae.
In your own outreach, are you optimizing for applause, or for impact?