My friends and the people I know understand that I'm going to ask

In the words of Sam Yagan, a builder of modern connections and a thinker of the digital age, there lies a lesson both practical and profound: “My friends and the people I know understand that I'm going to ask them what they're doing, how they're dating, who they're dating, where they're going and what they're doing. I'm constantly asking those questions and making sure I'm in touch with the customer.” Though his words may seem casual — the talk of a businessman or innovator — within them beats the eternal wisdom of those who seek to understand the human heart. Yagan’s curiosity is not idle; it is the sacred art of listening, of staying close to the pulse of life, of remembering that no great work can survive if it forgets the people it serves.

At the surface, he speaks of his profession — the world of online dating, of building systems that help others find love. But beneath the surface, he speaks of a deeper truth that stretches back to the ancients: that every great leader, merchant, or creator must remain in touch with the people. In the marketplaces of old, the wise trader did not sit behind ledgers alone. He walked among his customers, touched the fabric they touched, and learned the desires that moved their hearts. So too does Yagan, in the vast digital marketplace, walk among his users — not through city streets, but through conversation, empathy, and attention. He reminds us that technology may evolve, but human connection is still built on understanding.

The origin of this insight lies in the path Yagan himself walked. As co-founder of OkCupid and later a leader within the Match Group, he did not simply create systems; he sought to understand why people love as they do. He knew that the success of his work depended not on algorithms alone, but on the timeless emotions that drive every heart — hope, fear, loneliness, joy. His constant questioning — “Who are you dating? How are you dating?” — mirrors the approach of the philosopher Socrates, who sought truth not by proclaiming it, but by asking. Through questions, Yagan stays rooted in reality; through dialogue, he honors the complexity of human life.

This art of questioning, though often overlooked, is the hallmark of wisdom. The ancients knew that the one who listens more than he speaks is the one who learns. Consider the tale of Marcus Aurelius, emperor and philosopher, who despite his immense power, spent his nights in reflection upon the lives of ordinary citizens. He walked among soldiers and servants, learning their struggles and shaping his rule through understanding. Like Yagan, he knew that the strength of any system — whether an empire or a company — is measured not by its grandeur, but by its connection to the people it touches. Both understood that leadership without empathy becomes tyranny, and innovation without listening becomes arrogance.

Yagan’s words also carry a quiet humility. To “stay in touch with the customer” is to confess that one never outgrows learning. It is to acknowledge that the world is ever changing, and that to lead is not to stand above others, but to stand among them. The wise never retreat into isolation; they remain students of the present moment. The ego seeks control, but wisdom seeks understanding. By asking questions, by engaging with others’ experiences, Yagan reminds us that insight does not come from data alone, but from the living stories of real people.

In his relentless curiosity, we find the echo of a timeless principle — that connection requires attention. Whether one is a teacher, a parent, a leader, or a friend, the same law applies: to care is to ask, to listen, to seek to know. The relationships that endure — in business, in art, in love — are those rooted in empathy. The world often teaches us to speak, to persuade, to declare; but Yagan teaches the opposite: to listen deeply, to ask sincerely, to stay close to the heartbeat of humanity. For in listening, one becomes wise; in understanding, one becomes just; and in serving others, one becomes truly great.

Thus, let this be the lesson we draw from his words: never lose touch with the people for whom you labor. Whether your “customer” is a client, a student, a friend, or your own child, remain ever curious about their needs, their dreams, their pain. Speak less, ask more. Walk among those you serve and let their voices shape your vision. For to listen is not weakness, but strength — the kind that builds bridges across every distance. As Sam Yagan shows us, wisdom is born not from knowing everything, but from never ceasing to ask. And the one who listens to others, with humility and heart, is the one who will always find his way home to truth.