In 2010, I became the first comms hire at Square. We went public five years later.
In 2018, I helped Facebook reach and recruit a global engineering audience — and got the media to care about multiple data center announcements, way before frontier labs made that kind of thing cool.
By 2024, I had advised more than 3,000 Y Combinator startups on how to launch, tell their story, and reach the right audience.
Now, I advise both YC and non-YC startups, and two things have never been more true in my career of helping top-tier startups and companies tell their stories. First, AI has made it easier than ever to start a company. And, second, breaking through the noise has never been harder. Audiences are fragmented, attention is scarce, and it’s difficult to land media coverage. And really, does media coverage even matter anymore, in the era of “go direct”? (Spoiler alert, it does, but not just for the reasons you might think.)
There’s no one-size-fits-all answer, of course, but here are three tactics from my personal playbook to stand out in a crowded market and get noticed by the LLMs:
1. Don’t chase virality. Speak to your target audience.
The biggest mistake I see founders make: trying to replicate what’s going viral instead of creating content that speaks directly to their audience.
I’ve had multiple founders point to edgy, viral videos from controversial founders — content that performs well with young, technical men — and want to copy the format. But their own audience? Small business owners or enterprise buyers who don’t relate to that tone at all.
Your job is to create content that resonates — not alienates.
Your job also isn’t to be everywhere. You need to be where your audience is and to show up in a way that plays to your strengths.
Some founders are great on camera, like Amjad Masad (Replit). Others prefer podcasting, like Jacob Eiting (RevenueCat), or writing, like Aravind Srinivas (Perplexity). You don’t need to be on every platform. Choose one or two channels that match both where your audience spends time and what you’re good at, and then post consistently. The more you post content that’s genuinely useful to the people you’re trying to reach, the more likely it is for any one piece to take off — and the more fodder for top LLM search engines like ChatGPT or Perplexity to understand what your company is about.
2. Be consistent with messaging — for both your human and LLM audiences.
The best companies grow through word of mouth.
But for that to happen, people need to get what you do instantly and be able to repeat it. That starts with a one-liner: a clear, concise sentence that explains what your company does in plain language.
The biggest mistakes I see? Not leading with what you do and burying your message in jargon.
Take this one-liner: “Indy Cloud is a know-how and synergy platform.” Do you instantly get what this means? No. What about this one? "Nimbus is a next-gen collaboration layer powering integrated human experiences." No, again.
Now take Partiful: “Plan events in seconds.” It only takes four words to explain what they do.
When you have a one-liner that people understand, every channel should reflect it: your website and blog, social media bios, community platforms like Reddit or Discord, and in media interviews. Be consistent with messaging.
Mixed or inconsistent messages confuse people — and confuse AI.
Potential customers need to hear the same message over and over before taking action. And the same goes for LLMs like ChatGPT. As search interfaces, LLMs prioritize clarity, consistency, and comprehensiveness when surfacing answers. They like one-liners.
3. ‘Go direct’ and know how to work with media, both old and new.
Founders need a direct line to their audience. That’s your “go direct” strategy: creating blogs, videos, podcasts, webinars, events, Discords, social posts — content that speaks straight to your customers.
But the media — from journalists to influencers and content creators — are wildly important. They help expand your reach, offer third-party validation, and shape the answers LLMs surface about your company.
Muck Rack’s new AI report found that 27% of links cited by AI come from journalistic sources. And Profound found that up to 18% of links cited by AI come from YouTube.
It’s not ‘go direct’ or nothing.
You need to do both — and you need to know how to make your story interesting and relevant.
Today, a funding announcement or product launch isn’t enough to land coverage. You need to connect your story to something bigger:
What cultural shift or trend does this reflect?
What timely problem does it solve?
Why does it matter to the world outside your company?
Give reporters and creators a reason to care and a narrative they can run with.
And avoid one of the most common traps: pitching the wrong people.
“Technology reporter” or “Technology and online culture content creator” in a bio doesn’t mean they cover your space. Read their work, listen to their podcast, watch their YouTube, review their Substack. Know their beats before you reach out and make sure your story actually fits. A few targeted emails to the right person beats a spray-and-pray approach.
This is just the beginning, and I’ve got a lot more to share. I’ll be diving into it with some fellow YC alums on August 9 at The To Do List Summit in San Francisco, sponsored by Sentry, Brex, and Tandem. It’s a one-day event for early-stage founders to learn how to execute on comms, video, social, and events and reach their target audience in a very crowded market. We’ve got just a few more spots left, so apply here!