A few weeks ago, I met a young operator for coffee in Boston.
He works at an overseas co-living company operating in two cities. The business is real — hundreds of listings, established operations, real momentum. He reached out thoughtfully, proactively, trying to understand what selling into the U.S. might look like and whether there was a path forward.
The Pitch Began — and So Did the Déjà Vu
We sat down, ordered coffee, and started talking.
He began explaining the product. At first, it sounded like property management software.
I interrupted gently.
The U.S. market has no shortage of PMS tools. Some are excellent. Some are cheap. Some are extremely well-funded. It’s a market that rewards startups with great ideas but also one that’s brutally competitive.
So I asked a question I’ve learned to ask early:
“Why would I switch?”
There wasn’t a clear answer.
That moment felt uncomfortably familiar.
When the Story Keeps Shifting
Sensing hesitation, he reframed.
“It’s not a PMS,” he said.
“It’s a brand.”
They have hundreds of listings. A “network” in their existing markets. If I joined, I could tap into their user base.
And that’s when the déjà vu deepened.
I remembered doing this myself — shifting the narrative mid-conversation, hoping one of the angles would land. When you don’t have a sharp answer, you reach for more words.
But every shift makes the listener work harder.
By then, my head was full of questions he wasn’t asking.
Is the demand my current business challenge?
Will your users even book in my market?
If this is a brand, are you going to pour in marketing capital to grow the presence here? what does that actually mean in practice?
The pitch started to feel like PMS → marketplace → brand → network → everything.
And when you’re everything, you’re nothing.
Watching a Sales Conversation Quietly Derail
Nothing dramatic happened.
There was no clear rejection. No awkward ending. Just a gradual loss of focus — the kind that kills sales without anyone realizing it.
And that’s often how early startup sales fail. Not with a no, but with confusion.
What struck me wasn’t his ambition. It was how much of my younger self I saw in him.
I used to believe that energy and confidence could compensate for clarity. That customers needed to be convinced, not understood.
That belief cost me years.
The Lesson I Keep Relearning: Sales Is Listening
At some point, I found myself explaining my business instead.
How I operate.
What tools I use.
What problems I actually have.
If I’m going to spend two full days integrating my listings into a new platform, there are only two outcomes I care about:
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Will this reduce my costs?
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Will this increase my revenue?
Everything else is storytelling — and storytelling without numbers doesn’t move operators.
Early in my career, I thought sales was about persuading.
Now I know it’s about qualifying.
Sometimes the right outcome of a sales conversation is realizing you’re not the customer — and moving on quickly.
The Cost of Trying to Be Everything
Another old mistake surfaced.
The product was many things at once. Useful things, maybe — but unfocused.
I used to think broad positioning made a startup more impressive. In reality, it just makes sales slower and harder.
Clear positioning does something powerful:
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it shortens conversations
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it filters the wrong customers out
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it helps the right ones lean in faster
When you don’t know exactly who you’re for, every conversation becomes a struggle.
What This Conversation Reminded Me
Ambition is necessary. It’s often the only thing that gets you started.
But ambition without market understanding and a clear sales strategy is dangerous. I’ve seen founders burn time and capital they could never afford to lose — and I’ve done it myself, many times.
It was the quiet recognition that I once sounded exactly like that — confident, flexible, and slightly too eager to make something fit.
Sales doesn’t fail loudly.
It fails quietly — when clarity slips, listening stops, and ambition fills the gap.
And every time I forget that, the market is quick to remind me.
