There is a specific kind of silence that haunts every founder in the weeks leading up to a major event. It’s not the silence of a quiet room; it’s the silence of an empty inbox.
At Matters, as we prepared for our first-ever RSA Conference, that silence was deafening. We weren’t just showing up to scan badges; we were showing up to plant a flag for a new way of thinking about AI Security Engineer for Data. But as the countdown to San Francisco began, I found myself paralyzed by a single, terrifying thought:
What if nobody shows up?
The Month of Proof
We knew the statistics. We knew that during RSA week, a CISO’s attention is the most expensive real estate on earth. Every vendor is vying for a slice of their time, promising “revolutionary” fixes and “groundbreaking” AI guardrails.
We decided early on that we wouldn’t just send “Save the Date” invites. We didn’t want to be another notification to be swiped away. Instead, we spent a full month trying to earn our seat at the table before we even stepped onto the plane. We shared our white paper. We detailed our technical differentiators. We mapped out the specific, high-stakes use cases we had solved for our existing customers.
We wanted to prove our value on paper. We wanted to demonstrate that our “Holistic Lens”, the idea that you cannot secure AI without first understanding the data feeding it; wasn’t just a marketing slogan, but a technical necessity. We put our best work out there, and then we waited for the response.
And for a long time, there was nothing.
The Mentor’s Warning
The anxiety grew. I started reaching out to mentors, people who had survived a dozen RSAs and had the scars to prove it. I asked them about our plan for a co-hosted sundowner with Zluri, a two-hour cruise on a yacht in the Bay. I told them our goal was 50 people.
Their responses were a cold bucket of water. “Keshav, you have to expect a 50% drop-off at minimum,” they told me. “In the chaos of that week, people get ‘conference fatigue’ by 4 PM. Sessions run late, traffic is a nightmare. If 30% of your registrants actually walk across that gangway, you should consider yourself lucky.”
I sat with those numbers. In my head, I saw a beautiful yacht floating in the Bay, the sun setting behind the Golden Gate Bridge, and a handful of us standing and talking to each other. I genuinely feared that despite all the white papers and the outreach, the deck would remain empty.
From Waitlists to the Gangway
Then, the week arrived. And as the registrations began to climb, the fear of silence was replaced by the shock of volume.
The 50-person cap we had set for the yacht didn’t just fill up; it evaporated. People weren’t just clicking “Interested”; they were asking for invites. By the time we headed down to the pier, the data told a story that contradicted every warning I had received:
- 177 security leaders had registered.
- 84 were sitting on a waitlist.
- 93 CISOs, Heads of Security, and VPs actually walked across that gangway.
We didn’t see a “30% drop-off”. We saw an industry showing up with intent. In the busiest, most over-saturated week of the year, 93 of the most influential minds in security chose to spend two hours of their life on a boat with Matters.AI.
The Magic of the Ambassador
As the yacht pulled away from the dock, the atmosphere changed. This wasn’t a pitch-fest. This wasn’t a loud, neon-soaked party where you have to scream to be heard. It was a sanctuary of conversation.
I watched, almost as an observer, as our existing customers began to do the work for us. They were standing on the deck, drinks in hand, engaging with their peers. They weren’t reciting our pitch deck; they were sharing their real-world wins. They were talking about the “before and after” of implementing Matters.
There is no marketing campaign in the world that can match the power of one CISO telling another: “This solved a problem that was keeping me up at night.”
Does it Matter?
Somewhere in the middle of that two-hour cruise, as the Bay breeze cut through the day’s heat, I felt a massive internal weight lift.
I stopped “founder-moding.” I stopped worrying about the next person to talk to or the next slide to explain. I just started listening. And in listening, I found the answer to the question that had been haunting me for a month.
The fear of nobody showing up wasn’t about the event. It was about validation. It was the deeper, more vulnerable question: Does what we’re building at Matters actually matter to anyone but us?
When you are in the “founder bubble,” it’s easy to convince yourself that your solution is revolutionary. But when 93 leaders, the very people who have seen every “revolutionary” tool the market has to offer, choose to spend their evening on your boat to discuss your vision, the answer is clear.
Sitting with the Weight of 93
The industry is currently distracted by the “Day 1” noise—the flashy, trendy topics like superficial LLM security and content guardrails. But the leaders on that yacht weren’t there for the trend. They were there because they recognize the “Holistic Lens” we are building for.
They understand that the current approach is incomplete. They know that if you don’t understand the data, you don’t have security.
I am still sitting with the weight of those 93 people. Their presence wasn’t just a successful event; it was a mandate. It was a clear signal that the problem we are solving is real, it is painful, and the world’s top security leaders are looking for a solution.
To the 93 who crossed that gangway: thank you. You didn’t just join us for a sundowner; you gave us the ultimate validation. We left the Bay with more than just leads we left with the certainty that what we are building truly matters.
