I love moving through StartupYale as a witness—not just a presenter, but someone who gets to traipse through the energy of the day, watching it all unfold.
You see, I think StartupYale is a magical event. There were so many special moments I noticed when I first attended as a judge and speaker in 2025, and I fully expected the same experience when I returned again this year to lead a workshop.
Wondering what I mean about the magic? Well it’s not the pitches, though those are extraordinary. It’s not the awards, though watching someone hear their name called and realize their idea just got real funding is something I’ll never get tired of.
It’s something a bit more simple than that—it’s the conversations between founders in the hallway, a mentor leaning in during postering or the mentoring sessions, a founder’s face changing when something just clicks during a workshop, conversations between strangers over lunch as they realize they have more in common than they might have guessed when sitting down.
Which is why this year, I wanted to make sure I spent some time after the conference reflecting on my experience. Here are a few things I found most memorable.
The Foundational Framework
This was my second year presenting at StartupYale, and I lead a workshop on messaging—specifically, on how founders learn to turn what they’re building into a story people actually care about.
I’ve said it before, and I’ll say it again: strategic messaging is one of the most powerful—and most underutilized—competitive advantages a founder has.
It’s not a layer you add on top once the product is ready. It’s the thing that determines whether anyone stops long enough to care about what you’re trying to accomplish at all. In a world of AI, constant noise from social media, and shortened attention spans, the founders who break through aren’t always the most technically impressive. They’re the ones who communicate with confidence, strip away jargon, and anchor every answer in a clear narrative.
The framework I taught in this workshop has five elements: Hook, Clarity, Relevance, Stakes, and Soul.
Hook earns the right to be heard. Clarity makes you understood. Relevance connects what you’re building to what your audience actually cares about. Stakes make the cost of inaction real. And Soul—that’s the human, emotional truth underneath the business case. Together, they transform a pitch from a description of a product into a story someone actually remembers.
What I’ve learned from teaching this, year after year, is that none of it is new information. It’s not something I’ve discovered or the key to solving everything within someone’s business. But it is incredibly important, and the truth is—a lot of people have never been taught this before.
Sure, many founders have heard the word “storytelling” a hundred times. But there’s a difference between knowing you need a story and knowing how to create one—and that’s the gap the framework fills.
For some people it’s a genuine revelation. For others it’s a well-timed reminder that crystallizes something they already sensed but couldn’t name. Either way, the room always shifts when it lands.
When the Framework Clicks
After workshops like this one, a few people always linger. Some want to share a realization with me that they had mid-session. Others are still processing something that surfaced during the partner exercises—maybe it’s a moment of honest feedback from a stranger that hit differently than they expected. Other people want to add their thoughts to a piece of what I taught.
I love these conversations.
This year, one extremely quick conversation stayed with me more than the others. As I was packing up, I accidentally interrupted a conversation between two people in the audience. One of them was a founder—someone who had applied to compete at StartupYale 2026 but hadn’t moved forward as a finalist. And they said something I’ve been thinking about ever since.
“I knew something was off about our pitch. I just couldn’t figure out what it was. It wasn’t until this workshop that I figured it out: we don’t have a story. I mean—we do have a story. But we haven’t pieced it together in a way that shows what we actually mean. What we want to do. What we plan to accomplish. Why it matters.”
And y’all, they were visibly excited about this. In fact, they quickly ended the conversation so they could catch up with someone on their team and process this immediately.
That’s it, right there. That’s the whole thing.
They weren’t missing a product. They weren’t missing a market. They were missing the thread—the narrative connective tissue that takes everything true about what they’re building and makes someone else feel it. It’s such a specific, solvable problem. And watching a founder name it for the first time, out loud, is one of the best parts of this work.
When a Pitch from Last Year Becomes a Lesson for This Year
That wasn’t the only moment that stayed with me.
This year, I used three pitch examples from StartupYale 2025 to illustrate what the messaging framework looks like in practice. I picked three pitches that worked, and attempted to explain why they were so successful.
One of them was Black Obsidian Healing, a venture focused on community well-being among Black men. I wasn’t a judge in their competition, but I was in the audience when they pitched, and their clarity about who they were serving and why it mattered had stayed with me for over a year.
Here’s why I’m bringing this up now: After my workshop, someone from a community organization that partners with Black Obsidian Healing came up to me—during the session, they texted the founders while I was still speaking to let them know their pitch had made it into my content this year. That their work had mattered enough that someone was still talking about it twelve months later. Still learning from it.
I don’t know exactly how that landed for them. But I know how it landed for me.
It felt like a small reminder of what this conference actually is: a living, compounding thing. The pitches don’t just matter in the moment. They echo. And sometimes that echo shows up in a stranger’s workshop a year later, in a room full of people who needed to hear exactly that example at exactly that time.
What I’m Always Struck By at StartupYale
Every year, without fail, I leave this conference a little more hopeful than when I arrived—and it’s not just because of what the students are building, though that alone would be enough.
This year’s ventures spanned public health, climate tech, AI, creative work, community development, and financial access—built not just to be impressive, but to matter.
What moves me is the generosity of the whole thing. The students are building ventures that are ambitious and needed. But it’s also the mentors who show up from every possible background and industry…not to be impressive, but to be useful. The investors who give real feedback instead of polished deflection. The peer energy in the room. Students cheering each other on, pushing each other’s thinking, showing up not just to compete but to connect. The organizers who have built something that feels, against all odds, like a community rather than a competition.
That spirit is rare. And it’s contagious. It’s why I keep coming back.
The Story Is Already There
Being at this event now for two years in a row—watching founders wrestle with how to say the thing they’ve been living and breathing—has made me certain of one thing.
The story is already there.
They lived it. They built it. They know more about why this matters than anyone else in the room. The work isn’t inventing a narrative. It’s finding the one that’s already true and learning to say it in a way that makes someone else feel the weight of it.
It’s that hook that makes the listener lean in. The clarity that makes them understand. Relevance that makes the person learning about this venture see themselves in it. Stakes that make them feel what’s at risk. And soul—the human, specific, irreducible reason this exists at all.
That founder I mentioned earlier who came up to me after the workshop? They already had the story. They just needed a framework to see it.
That’s what I get to do and see at StartupYale. And I am so grateful for it.
I’ll be back at Yale in June for the TSAI Center for Innovation’s summer fellowship program, teaching SEO and messaging to a new cohort of fellows. If you’re a an organization looking for a speaker at your next event, or a founder working on how to talk about what you’re building—that’s the work I do. I’d love to help.
