I Send Over 100,000 Emails a Year - Here’s What Actually Works

Every year, I send over 100,000 emails.

Not newsletters, but real messages sent to investors, clients, partners, journalists, and countless people I hope to convince, meet, hire, sell to, or ultimately build something meaningful with.

If entrepreneurship had a sound, it would not be applause after business milestone or a funding announcement. It would be the quiet click of the send button, repeated endlessly, followed by long moments of uncertainty.

Because entrepreneurship is not primarily a battle of ideas. It is a battle for replies.

We like to believe companies succeed because of vision, intelligence, or strategy. These explanations are comforting because they make success appear rational and deserved.

Yet, after 20 years of building companies, I have learned something far less glamorous and infinitely more practical:

Most opportunities do not depend on how brilliant your idea is. They depend on whether people answer your emails.

The greatest danger for an entrepreneur is not rejection. It is invisibility. Silence kills more startups than failure ever will.

When founders complain that investors are unreachable or clients are impossible to engage, the issue is rarely access. The real problem is attention.

Modern business professionals live inside overwhelmed inboxes where every message competes against dozens of others arriving simultaneously. Your email does not compete against other startups; it competes against fatigue, distraction, and cognitive overload.

Which means the first entrepreneurial skill is not pitching. It is mastering the art of the hook!

The subject line is not a detail. It is strategy. Before anyone evaluates your product, your vision, or your market, they evaluate whether your message deserves three seconds of attention.

Corporate environments rarely prepare people for this reality because corporate communication optimizes safety. Tone must remain neutral, predictable, and controlled. Creativity is risky when you represent an institution.

Entrepreneurs operate under opposite conditions. If nobody notices you, you simply do not exist!

After 20 years of entrepreneurship, I stopped treating emails as correspondence and treat them as headlines. Journalists learned long ago that readers decide instantly whether to continue reading. Entrepreneurs must adopt the same discipline. A strong subject line interrupts routine thinking just enough to provoke curiosity without damaging trust.

Some subject lines work precisely because they create an emotional tension: "You don’t want to miss this," "I’ve got some bad news for you," or "Are you serious?" These lines are not manipulative when used honestly. They acknowledge a simple reality: attention must be earned before value can be delivered.

The crucial moment comes immediately after the open. Curiosity must be followed by reassurance. The reader needs to feel respected, not tricked. The hook opens the door; credibility keeps it open.

One subject line I often use is "I know what you did." It sounds provocative enough to interrupt routine thinking, yet the first sentence instantly clarifies the intention: "you attended one of our events last year and we would love to invite you again." Surprise captures attention; transparency restores trust.

Entrepreneurs must learn to navigate that narrow space between originality and credibility.

Of course, boldness has limits. I once saw this subject line "I saw your name in the Epstein files."

The open rate was probably spectacular. It is also a perfect example of the wrong lesson. The objective is not shock value but memorability grounded in integrity. Attention gained without trust evaporates quickly.

Yet, even the best hook rarely succeeds alone.

The second lesson learned after sending hundreds of thousands of emails is that persistence matters far more than most people are comfortable admitting.

My business partner Luka has mastered this discipline better than anyone I know. Where many professionals send one email and quietly move on, Luka follows up patiently, sometimes five to six times, always polite, always slightly different, creative, and respectful.

And then something fascinating happens... People reply!

Nothing fundamental has changed about the proposal. The opportunity is the same. What changed is time, and visibility. Research in sales outreach consistently shows that a large share of responses arrives only after multiple follow-ups, yet most professionals abandon outreach after the first attempt because they fear appearing intrusive.

Entrepreneurs cannot afford that fear.

Busy people rarely ignore you intentionally. They postpone, forget, or intend to respond later. A kind reminder is not pressure; it is assistance. You are reopening a conversation that was never consciously rejected.

Luka occasionally sends reminders with a GIF of Mr. Bean impatiently checking his watch! It sounds almost absurd in a professional context, yet it works remarkably well. Humor breaks formality and signals confidence. It reminds the recipient that business remains, fundamentally, a human interaction rather than an institutional exchange.

The important rule is that reminders must evolve. Repeating the same message feels mechanical. Each follow-up should introduce a new angle, new information, or simply a fresh tone. Persistence without creativity feels desperate. Persistence combined with creativity signals leadership.

The final discipline entrepreneurs consistently underestimate is the call to action.

Many emails end politely and die quietly. Phrases such as "Let me know your thoughts" or "Gentle reminder" appear respectful but create friction because they transfer effort back to the reader. Faced with decision fatigue, most recipients postpone indefinitely.

Great entrepreneurs reduce uncertainty. They propose movement. Two meeting options instead of an open-ended question. A clear next step instead of vague interest. Momentum emerges when decisions become simple.

Over time, I realized that entrepreneurship is less about convincing people and more about guiding attention toward action. Founders are not only builders of products or organizations; they are architects of conversations. Every subject line, every reminder, every call to action contributes to a rhythm that eventually creates opportunity.

Rejection rarely destroys companies. Being ignored does.

Many of the partnerships, investments, and breakthroughs that shaped my entrepreneurial journey did not begin with extraordinary presentations. They started with an email sent at the right moment, written with enough originality to be opened, followed by thoughtful persistence that kept the conversation alive long enough for alignment to occur.

Entrepreneurship rewards those who remain visible with integrity.

The founders who advance fastest are not necessarily the smartest or best connected. They are the ones who understand that attention precedes opportunity. They learn to write subject lines people want to open, reminders people appreciate receiving, and calls to action that make progress inevitable.

After sending over 100,000 emails a year, the lesson is surprisingly simple. Entrepreneurs do not win because they send perfect emails. They win because they continue showing up persistently, thoughtfully and creatively, until conversations begin.

Because companies are not built only through innovation or funding rounds. They are built through relationships, and relationships always start the same way: someone opens an email, someone reads, and someone finally decides to reply.

And in that small, almost invisible moment, entrepreneurship truly begins!

Now, over to you:

• What’s the best subject line you’ve ever sent… or received?

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