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Key Takeaways
- Stop trying to be interesting — instead, be interested. Ask thoughtful, curious questions. Say less about yourself and more about the person you’re connecting with.
- Understand that relationships are grown (not hacked) and that one honest conversation beats ten superficial ones.
- People want to help — but you have to make it easy. When someone says, “Let me know how I can help,” they mean it. But you have to clarify what that help looks like.
- Connection capital compounds. Every authentic relationship you invest in can yield returns years down the line in the form of introductions, collaborations, ideas and support.
In my early years as an entrepreneur in New York, I thought I was doing everything right. I was attending every panel, RSVP-ing to every networking mixer and collecting more business cards than I knew what to do with. I showed up, smiled and delivered my elevator pitch with precision. But I always walked away feeling … empty. Like I was playing a game where no one remembered anyone after the name tags came off.
Looking back, I now realize what was missing: connection.
It wasn’t until I slowed down, changed my approach and started prioritizing real human relationships that things shifted for me, both professionally and personally.
Here’s what I’ve learned about moving from networking to connecting, and why that difference has made all the difference in how I build, hire, grow and live.
Stop trying to be interesting. Instead, be interested.
I used to feel pressure to impress people. I thought the point of networking was to showcase my wins, my product, my story. It wasn’t disingenuous; I was proud of what I’d built, but I was constantly in “performance” mode.
Then I had a moment I’ll never forget: I went to a brunch hosted by a founder friend and sat next to someone I didn’t recognize. Instead of trying to pitch myself, I just asked them questions — about their story, what brought them to the city and what they were excited about. Two weeks later, they reached out and invited me to create a WhatsApp group of tech founders in New York, where I would later meet one of my most valuable mentors.
All of this happened not because I pitched well, but because I listened well.
So my advice here is, the next time you’re at an event, challenge yourself to say less about you and more about them. Ask thoughtful, curious questions — and mean them. People remember how you made them feel, not just what you said.
Relationships are grown, not hacked
We live in a culture obsessed with growth hacks. But you can’t hack trust.
Some of the most impactful partnerships I’ve ever formed, including Replay Listings’ early support from real estate professionals, came from slow-burn relationships. I didn’t meet someone and then pitch them immediately. We built rapport, shared ideas and kept in touch. Sometimes, nothing came of it for years. And then one day, they’d introduce me to someone, or a new project would land in my lap from a conversation we had ages ago.
Here’s a secret I have and still use after over a decade: Keep a short list of people you genuinely like and admire, even if there’s no “strategic” value today. Once a quarter, send a personal message. Share something that made you think of them. That’s not networking. That’s community-building. Pro tip: I often leverage the holidays to reconnect. A simple “Happy holidays!” is a great conversation starter, and it helps them keep you in mind.
One honest conversation beats ten superficial ones
When I was building Replay Listings, I was juggling real estate, tech, marketing and what felt like 50 fires at once. In the middle of it all, I got invited to speak at an event. I almost didn’t go. I was exhausted. But I showed up, and instead of “playing founder,” I told someone I just met that I was overwhelmed and trying to figure out how to build a better hiring process.
That honesty led to a connection with someone who had experience scaling tech teams. That one conversation ended up being more valuable than dozens of perfectly polished interactions I’d had that year.
All of this to say: When appropriate, be real. Vulnerability isn’t weakness — it’s an invitation to connect. When you let someone see the real you, it gives them permission to do the same. And from there, real partnerships are born.
People want to help — but you have to make it easy
I’ve learned that most people genuinely want to support others. But if you’re vague about how they can help, they’ll do … nothing. When someone says, “Let me know how I can help,” they mean it. But it is on you to clarify what that help looks like.
When I was building the early prototype of Replay Listings, I reached out to a real estate contact and said, “Would you be open to filming a 90-second video of a listing to test our platform?” That small, specific ask became one of our first uploads and helped validate the concept.
If you’re reaching out, make the ask easy to say yes to. Instead of “Can we work together?” try “Would you be open to a call next week to discuss XYZ?” Remove friction. Be clear.
Build connection capital — it compounds
Just as financial capital compounds, connection capital compounds as well. Every authentic relationship you invest in can yield returns years down the line — introductions, collaborations, ideas, support.
Some of my biggest opportunities have come not from cold emails or formal pitches, but from a text, a recommendation or a casual intro from someone I had coffee with years earlier. Those aren’t just connections. They’re seeds you planted.
Think of your network not as a collection of contacts, but as a living, breathing ecosystem. Nurture it. Give first. Be the person who sends the helpful article, the unexpected intro, the kind follow-up. Over time, the returns will surprise you.
The truth is, I no longer see “networking” as part of my job. I see it as a side effect of how I live. When you lead with curiosity, generosity and presence, connections take care of themselves.
So don’t chase people. Build relationships. And don’t collect business cards. Create community.
Because in the end, it’s not about who you know, it’s about who knows you, trusts you and wants to build something alongside you.
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Key Takeaways
- Stop trying to be interesting — instead, be interested. Ask thoughtful, curious questions. Say less about yourself and more about the person you’re connecting with.
- Understand that relationships are grown (not hacked) and that one honest conversation beats ten superficial ones.
- People want to help — but you have to make it easy. When someone says, “Let me know how I can help,” they mean it. But you have to clarify what that help looks like.
- Connection capital compounds. Every authentic relationship you invest in can yield returns years down the line in the form of introductions, collaborations, ideas and support.
In my early years as an entrepreneur in New York, I thought I was doing everything right. I was attending every panel, RSVP-ing to every networking mixer and collecting more business cards than I knew what to do with. I showed up, smiled and delivered my elevator pitch with precision. But I always walked away feeling … empty. Like I was playing a game where no one remembered anyone after the name tags came off.
Looking back, I now realize what was missing: connection.
