What 500 DMs a day taught me about talking to people

I didn't start with a strategy. I started with a spreadsheet, a LinkedIn tab, and no idea what I was doing.

At Bytespace, I was the first hire. No sales playbook, no CRM, no one to ask. So I did what every experienced salesperson tells you not to do: I started sending cold DMs manually. One by one. Hundreds of them a day.

Not because I thought it was the right approach. Because I didn't know any other way.

Volume is the answer nobody wants to hear

The conventional wisdom in sales is that you should spend weeks building the perfect customer profile before you send a single message. Understand your ICP. Map the pain points. Design the messaging.

I didn't have weeks. So I went the other direction: talk to as many people as possible, as fast as possible, and let reality tell me who actually cared.

At 500+ DMs a day, I had more signal in one week than most people get in a month of "research." Not because I was smarter — because I was talking to more people. Every non-reply is data. Every "not interested" is data. Every reply that doesn't go anywhere is data. You start to see the pattern fast when you're moving at that volume.

By the end of week one, I knew who our actual customer was. Not who we thought they were — who they actually were. That distinction matters more than most founders admit.

Three things I actually believe about sales

After thousands of messages, I landed on three principles I haven't been able to shake.

Know your customer — but not the way people mean it. Don't design a profile, wait, then go sell. That's backwards. Go talk to hundreds of people, ask them questions, and let them build the profile for you. The customer profile isn't something you design in a doc. It's something you extract from real conversations at volume.

Volume is everything. More messages means more replies, more signal, more refinement. There's no shortcut here. If you're not sending enough, you're not learning fast enough.

Twenty follow-ups before you quit. I've watched deals die because someone sent two messages and called it cold. Sales is insistence. Not aggressive insistence — patient, persistent follow-up that treats the other person like a human who's just busy. Most salespeople give up at three. That's the opportunity.

The take that makes product people uncomfortable

There's a romanticization of the product side in tech. The builder, the designer, the person who shapes what gets made. Sales is often treated as execution — the layer that comes after the real work.

I think that's wrong, and I think it costs companies a lot.

A good salesperson is on the front line every single day. They know what customers actually complain about, what language they use to describe their pain, what almost made them buy and what stopped them. They know things that no product spec or user research doc will ever capture.

There should be a 1:1 relationship between whoever builds and whoever sells. Not product deciding what to build and then handing it to sales. Both in the room, both with context, making decisions together. When that doesn't happen, you get teams building things based on what they think customers want instead of what they know.

On AI tools and the order of operations

At Bytespace, we had the technology to automate all of this. We could have automated outreach from day one — that was literally what we were building.

We didn't. And I think that was the right call.

Automation only makes sense once you know what you're doing. If you don't know who to contact, what message converts, or how to handle the replies you get — automating just means you're making the same mistakes faster. You need to send the first thousand messages yourself. Feel the friction, read the responses, understand the patterns. Then automate.

The obsession with AI tools in sales is real, but it's mostly a way to avoid the uncomfortable part: talking to people, getting rejected, and learning from it. No tool replaces that. The tool comes after.