Jesse Caesar is a qualitative market research expert and brand strategist in Brooklyn. He previously worked at Open Mind Strategy, Firefly Millward Brown, and boutique branding agencies. With a psychology and anthropology background from UC Berkeley, his approach emphasizes storytelling, empathy, and creativity to uncover consumer motivations.

I first discovered Jesse through this great article, “Why Qualitative Market Research Belongs in Your Startup Toolkit — and How to Wield it Effectively.”

I start all my conversations with the same question—one I borrowed from a friend who helps people tell their stories. It’s a big, beautiful question, which is why I use it. But because it’s so big, I tend to over-explain it—like I’m doing right now. Before I ask it, I just want you to know that you’re in total control. You can answer in any way you want—or not at all. The question is: Where do you come from?

I’d be remiss as a researcher if I hadn’t listened to some of your previous podcasts before asking that. I like the question, and I’m going to answer it in a few different ways. I come from good people. I was raised in a very loving home—encouraged, supported. There were big expectations, but always a lot of love. And I think that foundation was a great springboard for me to explore the world, figure out who I was, and how I fit into it. The journey continues.

I come from L.A. Born and raised an Angeleno, but I probably identify more as a New Yorker now. I’ve been here for quite some time. And I come from a place of fun. I’m a real fun seeker. Part of that is creativity, part of it is curiosity, part of it is just a need for variety. I like bursting bubbles—especially my own.

What do you mean by ‘bursting bubbles’?

It’s about stepping out of the zone. Whether that’s going too deep into industry webinars and project work and needing to snap out of it—or just getting outside, interacting with people, going to MoMA, watching a movie, reading a book. I like to change things up. It’s not always just nonfiction, either. Fiction is important—a little sorbet, a palate cleanser in between. I’m constantly looking for ways to shake things up.

Do you remember, as a kid, what you wanted to be when you grew up?

Yeah. My eighth birthday was actually at a focus facility. I had no idea at the time how fitting that would turn out to be. My career path has definitely been a zigzag—a circuitous route. But I think what’s been constant is this desire to perform, to entertain, to make sense of things, and to have fun.

I still think that someday I’ll be an artist. Someday I’ll be a writer. I came to New York with dreams of being an ad man.

Oh, is that right?

Yeah. I don’t know if it was a lack of gumption or grit to pursue being a proper artist or writer, but I felt like I could do copywriting. Maybe art direction would be my thing. So I started out as a media planner at MediaCom, which was part of the same agency network as Grey Advertising. My plan was to work my way laterally—build up my portfolio, learn the ropes from the media planning side, and eventually shift into creative.

That makes sense. So then, catch me up—what do you do now? And when did you first discover qualitative research?

Yeah, no, qualitative wasn’t even on my radar until years later. I was working at MediaCom in my early New York days, having a lot of fun outside of work—but doing a job that wasn’t fun. Being in that big corporate agency world, I fell out of love with advertising. It felt disconnected. I kept seeing the same formula applied, quarter after quarter. Then the client would do a review, fire the whole team, retool the formula, rinse and repeat. There was a disconnect from the work itself, from the brand, and from the consumer we were supposed to be reaching.

From there, I moved to a very boutique branding shop. And when I say boutique, I mean three of us were full-time staff. But what drew me to it was the chance to work with brands when the clay was still wet—when things were still just the seed of an idea. Some were new brands getting off the ground, others were more established but looking to solve a problem or do something different. I got to wear a lot of hats there, and one of them was research.

It wasn’t a formal introduction to research, but it was eye-opening. I had come from ad land with this attitude that market research was just a way to water down great creative thinking. But being exposed to research in a branding context changed that for me. From there, I went to what was then Greenfield Consulting Group, which later became Firefly and Millward Brown. That was the first time I ever felt at home. Even in the interview process, I remember meeting all these moderators—fun personalities, super sharp, deeply curious people. And I thought, These could be my mentors. I could see myself doing this. I like this vibe.

What was the attraction? You said you moved to New York to be an ad man—what did that mean to you then? What drew you to it?

I think part of it came from where I saw my strengths in creative work. But part of it was definitely influenced by movies and TV. This was before Mad Men, but even then, advertising still had this sheen of glamour. I don’t think that’s quite the case anymore, but at the time, it seemed like an exciting, dynamic lifestyle.

Honestly, I wasn’t entirely sure. Even back in school, I was figuring things out as I went. I remember being pulled into an advisor’s office my junior year and being told I had to declare a major. That’s how I started as an anthropology major—then I took enough psych classes to make psychology my primary major.

It was all a bit of experimentation, a lot of playing around, seeing what worked and what didn’t. I came to New York without a clear vision of exactly what I was going to do—just that it would be something very different.

My whole family is from New York, but my only real experience with the city had been visiting relatives. It was intimidating—fast, loud, crowded. I wasn’t used to all that. It felt overwhelming.

But the summer before I graduated, I came to New York for an editorial internship at Mad Magazine. At the time, I was still very much a California boy—I had been at Berkeley, soaking in that West Coast mentality. But that summer in New York was a watershed moment for me. Just a few months of living here made me realize I needed a place that was going to kick me in the ass a little. And New York was a good fit for that.

Tell me a little about the work you do now. How do you describe what you do? And you also mentioned performance as part of what drew you in—how does that connect?

Yeah, I’ll start with the performance side and how it ties back. I grew up in LA, where the siren call of Hollywood was never far away. I did act as a kid—the way most kids do, meaning I went on a lot of auditions and didn’t book much. But I did get one role. Ironically, that was the end of my acting career. I landed a featured role in a movie, and my parents just said, Nah, we don’t want you missing

What was the movie?

Camp Nowhere.

Did this movie actually happen?

It happened.

Do you want to talk about it?

It’s too painful. No, I just… I’ve never really watched it. It was a Christopher Lloyd movie—seemed like a gas. But yeah, I probably should watch it at some point.

Oh my God.

What trajectory my life could have taken…

I’m feeling a lot of pain for young Jesse. Maybe because I shared that—I was also glued to TV and movies, wanting to be in that space.

Oh yeah.

So the idea that you had the opportunity to be there, and it went away—that would be a big deal. How old were you?

Twelve. That was another factor—hitting that wall. Every weekend was a bar mitzvah, and I was starting to study for my own. So there was no more time for acting class. Between school, extracurriculars, and everything else, it just became impossible to go to auditions. That was kind of the end of it.

So now, tell me about the work you do. And what’s the connection to performance?

One of the things I love about moderating is that I do get to flex that muscle a bit. There’s an element of commanding a room, putting your energy out there, keeping the momentum up, and presenting ideas in a way that engages people.

And then, of course, there’s listening—not just hearing, but really being present, aware, responsive. Actors talk about being in the moment, responding authentically. Moderating has some of that, too. You have to be able to shift modes quickly—moving from interviewing participants to debriefing with clients, to synthesizing all those insights into a compelling story.

And that storytelling piece is crucial. Even if the final deliverable is just a PowerPoint, how do you infuse it with a sense of drama? How do you pull people in from the start? I like that part—taking all the pieces, making connections, and bringing it to life.

You know, as you’ve probably felt, things flipped during COVID. What was maybe 40% of our interviews happening remotely suddenly became 80% or more. And that shift has largely stuck.

It’s tough not to be sharing air. I find I have to work harder in this little square. I can’t take up space in the same way. I don’t have all those nonverbal cues or the full context of a room—just whatever I can see over your shoulder. Earlier, you asked how I describe what I do. And I think that’s part of it—performance, presence. But ultimately, it’s about solving problems.

If I had to give it a logline—back to Hollywood—I’d say: I solve problems for companies by talking to their customers.

I could keep spinning on this, but at its core, it’s about forming connections. It’s about me connecting deeply with another person so that I can help my clients connect with them too.

Yeah. I mean, the first time I ever came across you was through that piece in First Round. It was such a beautifully articulated argument for the benefits of qualitative research—especially for an audience that so often just doesn’t get it. As a researcher, I’ve definitely hit that wall of miscomprehension before. And I remember reading that and thinking, I need to talk to this guy. This is fantastic. So I’m curious—how do you think about the proper role of qualitative? How do you make the case for it to someone who just doesn’t see the value? If a client calls and says, Hey, I hear you’re great—tell me what you do and why talking to people matters at all—what do you say?

Yeah, first, I just want to correct the record—I didn’t write that piece for First Round. Their editorial team did an excellent job profiling me, but it wasn’t my byline. That said, a lot of my thinking was in there. And I really appreciate the work you’re doing in this space—advocating for qualitative, pushing for it in ways I haven’t been as active about lately. A rising tide lifts all boats, and I think that’s especially true in this field.

As for making the case for qual? Sometimes I start with truth. That truth shows up in the first conversation with a client—or a prospective client—and sometimes it leads me to saying, Qual isn’t the right approach for you here. Either because it’s not the right solution for the problem they’re trying to solve, or because they don’t have the time and resources to do it well. And if you can’t do it well, don’t do it poorly—because this is a directional science.

But broadly, making the case for qual comes down to this: Most people today accept the reality that we are not fully rational creatures. We need narrative, we need storytelling, we need emotional appeal. That’s what motivates a lot of our behavior—including consumption.

And you can’t unearth those deeper motivations without qualitative research. You need dialogue. A survey won’t give you that, because a survey starts with built-in assumptions: These are the metrics that matter. This is how people talk about them. And when you structure research that way, so much gets lost.

So much is missed when you can’t follow up on someone’s first response. One of my first real mentors in moderating, Andy Greenfield, talked about triangulating on the truth—asking questions in different ways to get at the deeper answer. That means using different approaches—not just qual, but maybe layering in quant, observation, interrogation. Even within a discussion guide, you build in exercises that help uncover what’s really driving behavior. All of that—those layered, human-centered methods—that’s how we surface the most meaningful insights for our clients.

It’s tough to make the case for qual because it’s squishy—it’s hard to point to ROI, especially for the kind of research I love, which is much more foundational and brand-driven rather than tactical UX questions like “A or B?” So I try to establish trust early on. I use my skills as a moderator in those initial client conversations—really listening, understanding their problem, and figuring out whether I am actually the right solution.

And then, the work itself has to prove its value. When I’m in the field, I like to bring my clients along as much as possible. I want the process to be collaborative, for them to have ownership of the work. That way, they feel confident socializing it within their own teams—they aren’t just passively receiving insights; they understand them, they believe in them.

I also lean into being a proud generalist. I need my clients to be my insiders—to give me the context, the “inside baseball,” whether it’s industry-specific or just company culture. That helps me make sharper, more relevant leaps in my implications. And then, doing the work itself—after the first few interviews, I always build in a debrief. We talk about what we’re hearing, make adjustments, focus on what’s actually yielding depth, and move away from areas where we’re hitting diminishing returns. It’s an iterative process.

At the end of the day, it’s about meaning. You put all these conversations together, extract the insights, and ask: What does this mean for you? Does it solve the problem? That’s the real proof point.

What do you love about the work? Where’s the joy in it for you?

I love the exploration. Even in a sector like HVAC, there’s fun to be had. There are cool things to discover, and creative ways to get at those discoveries. I love using both sides of my brain—being creative in methodology and presentation, but also analytical in identifying patterns and drawing connections to implications. It’s fulfilling to be engaged that way. It’s exciting. Even just designing the right methodology gets me worked up in a positive way.

For people who might not have experience in research—can you tell a story? How do you approach something like HVAC? How do you make it exciting? I completely agree—anything is interesting if you approach it with curiosity, dig in creatively, and make the right connections. So with HVAC—what’s the thrill?

I mean, everybody has their treasure.

There’s no such thing as a bad respondent. Sure, you need to screen for relevance—make sure they’re the right person for the conversation—but everyone has something to express, an experience to share. Sometimes, people struggle to write it out. Sometimes, they struggle to talk it out. That’s when you need to shift methods—maybe a little show-and-tell, maybe something more interactive. That’s why I love ethnographic methodologies.

Take HVAC, for example. Go on a ride-along. Watch an install. See if you can get on your belly and crawl into those crazy tight spaces. Because for a lot of these guys, their scars are badges of honor—proof of how hard they’ve worked to get into those impossible spaces, to install and maintain equipment. There’s no one-size-fits-all method for getting insights. Ideally, you’re triangulating—layering multiple approaches together.

Some people love to poo-poo focus groups, but I think they’re an incredible tool. When a group of people comes together and starts sharing, the whole becomes greater than the sum of its parts. You can feel the insights laddering up in real-time. There’s something almost therapeutic about it. Honestly, one of the hardest parts of this work? Getting people to leave at the end of an interview. Because when do you ever have someone listening to you that intently? Actively, curiously? Outside of therapy—or maybe when you’re buying drinks from a bartender?

You mentioned one already, but I’m curious—who were your mentors? And beyond people, are there any ideas or concepts you consistently return to?

That’s an interesting question. The other side of bursting bubbles is—what are the foundations I hold dear? For me, I always come back to the fundamentals I learned as a baby mod—the core skills I had to develop when I was starting out.

What were those fundamentals for you?

It’s the basics, really—how to ask questions. And there is a right and wrong way to do that. Some of it’s been debated endlessly—like don’t ask why. And sure, qual is ultimately about the why—but “why?” isn’t actually a great way to get there.

Let’s stay with that—because it makes intuitive sense to people to just ask “why?” So how do you explain the danger of it?

“Why?” puts people on the defensive. It tightens the butthole a bit. It demands a rationale. And as we’ve touched on before, people aren’t driven by rationale. We construct rationales after the fact to explain our behavior, but the real drivers come from deeper places. Asking “why?” too early cuts you off from those depths. It forces people to plant a flag—“this is why I do this”—and suddenly, the conversation narrows. It becomes rigid, harder to explore, harder to go deeper. It’s boring.

It’s also lazy. It’s not fun. And look—even if you’re talking to someone about antiemetic medication for cancer treatment, even in serious conversations, there’s no reason why the discussion itself can’t be engaging. You can uncover real trauma, real depth, and still make it approachable. That’s part of what makes a great conversation—keeping it from feeling transactional. It’s not Give me an answer to this question. It’s Let’s explore this together. So yeah, fundamentally—it’s got to be fun.

There’s this one clip I always go back to—it’s a therapist, oh my god, I’m totally spacing on her name—but she talks about a therapeutic practice she calls conversational questions. You just reminded me of it, because she says that why questions are transactional. They create distance between you and the person you’re asking, and they actually cut off the relationship. Instead, she describes these conversational questions as a way of participating in a conversation, rather than just trying to extract an answer. And that always stuck with me.

I think that’s part of what I hear in what I do—what I identify with. It’s about asking questions that keep things alive, that keep things moving rather than shutting them down. “Why” is a shut down question. Like you said, it forces people to plant a flag and stops exploration.

And honestly, it’s just nice talking to a fellow researcher who gets it—who experiences the terrain in the same way. But yeah, I love the way she framed it—that questions are ways of participating in a conversation, rather than just seeking answers. And I wonder—what does that spark in you?

Because so much of research today feels so answer-seeking. It turns people into answer-generating machines, and then we take those answers at face value. I think there’s an overconfidence in what gets produced when you approach a person that way.

Yeah, I think that’s spot on—the idea that conversation is about showing you’re listening. If people don’t feel that, if they don’t trust that you’re engaged, they check out. They go into auto-pilot mode—just trying to get through the transaction. And the moment it stops being a conversation, you lose the chance to get anything real.

The challenge, of course, is not leading them too much. There’s a balance. I think it’s good to recap what you’ve covered, put a bow on it, and offer it back: Did I hear that right? Does that feel accurate? That way, I’m not telling their story in a way that doesn’t fit.

But it’s also about pushing deeper. And you can only do that if you’re willing to wander a little. Not aimlessly—you still have your objectives, your discussion guide—but you have to be willing to let go of your agenda to get something richer in return.

And honestly? If you’ve done a good job of building trust—if you’re likable, easy to talk to—you also earn the permission to wrestle with them a little. To call them out on contradictions, push them where it makes sense. It’s not about judgment. The space has to feel safe. But when you lean into friction, that’s often where the real insights are hiding.

You talked about not leading—what are some of the other fundamental things you’ve learned?

Because in a lot of ways, what we do is invisible. It just looks like a natural, interesting conversation. But in the background, there’s a lot happening.

When you say you don’t want to ask leading questions, how do you actually do that? What’s going through your mind?

Sometimes, it’s not about asking a question directly—it’s about giving the person something to do that helps them answer it. I want my questions to feel natural—relevant to the conversation we’ve been having. But I never want to impose my own values or assumptions. As a generalist, I feel like I have an advantage when stepping into a new space. I don’t carry the same sacred cows that might weigh on others in that industry. That gives me the ability to leave room—to let the other person fill in the blanks. Sometimes, I’ll frame a question as a straw man argument—like, I’ve heard other people say this. What do you think is going on there? What are they missing? But as much as possible, I want to create space for them to do the talking. Yes, it should feel like a conversation. But they should be talking more than I am.

Are there any other mentors or touchstones that come to mind?

Yeah, well, I mentioned Andy Greenfield and some of my fellow moderators from those early days. There wasn’t a formal program for someone who didn’t come from the moderating world or from the other side of the glass, so my early days were a lot of shadowing. I spent a lot of time observing moderators I thought were best in class. That school—those people—I’m still close with, like Olumobile Ade. I think she’s brilliant.

I also find a lot of inspiration—not necessarily mentorship—from other places, parallel industries, and even through art. For me, it’s about bringing that generalist mindset to the wider world, being a sponge, and taking in influences from all different places.

How have things changed for you? How has your method, your practice, or what you do evolved as we’ve shifted more into remote work? And how do you think about remote versus in-person? I don’t know why I’m labeling it that way in this conversation, but how do you operate now, and how is it different from before? Because we were in a “before,” and now we’re in an “after.”

Honestly, the “after” was actually a boom to my bottom line. I was able to do a lot more fieldwork than I had before because, yeah, you don’t have to factor in travel time. It’s a lot more efficient. But, as with many efficiencies, you lose some quality.I try to avoid online groups—certainly anything more than four people at a time. Once you go full Brady Bunch mode, it just doesn’t work.

Talk to me about that experience, because I feel the same way. Groups online are extremely challenging and best avoided. But what’s the rationale? What makes it difficult or not worth doing?

Without that immediacy, I think you lose accountability. It’s easy for people to shrink away from the conversation, and there are a lot more distractions—people checking their phones or even answering emails right in front of you. You can see it happening. I don’t like being the kind of moderator who calls people out by name. I want everyone participating because they’re engaged, because the conversation is fun, because I’ve made them feel empowered to share their perspective. But it’s tough without that shared air.

I can’t just lean in, make eye contact, or hold up a hand to subtly steer the conversation. It loses a lot of that natural energy. I miss in-person work, and it’s starting to come back. I don’t know what your experience has been recently. You reached out looking for a creative loft space—did that end up going through?

More and more, I’m looking for opportunities to do in-person work. And for me, it’s also about ethnographic research—those in-situ interviews. You just can’t replicate that on a screen. You can’t do a shop-along or step into someone’s home. I love going into people’s homes because that’s where their freak flag flies—where you really see how they organize their lives, what they value. It’s all being expressed around them before you even start the conversation. That rich context is invaluable. And then, of course, the other big industry shift happening right now is AI. I’ve even done some work advising an AI company that was developing an AI-moderated conversation tool. It’s exciting.

It’s exciting, but of course, all that excitement comes with a little bit of terror. Ultimately, though, it’s been clarifying for me. AI is probably going to take some of the bread out of my mouth, but mostly for the kinds of projects I don’t really want to be doing anyway.

I want to focus on projects that are more foundational, more strategic, more exploratory—the kinds of work that fit a more ethnographic approach. And until they upload an AI into a body that’s born, feels things, and dies, I think I’ve still got an advantage.

I want to hear more about that. I feel like some of this conversation starts out very simply but gets complicated quickly. How do you imagine AI impacting the kinds of projects or research where someone like you is still needed?

Yeah, I think AI is going to be used in ways it probably shouldn’t and provide answers that aren’t complete. That’s part of our job as champions of qualitative research—not just to advocate for qual but to also help define AI’s role. It’s not helpful to dismiss it entirely. It’s just another tool in the toolkit, right? Just like Zoom.

There’s probably a good place for AI in UX research—things like button placement and basic interface testing. You don’t need deep human insight for that. AI can also make survey research more meaningful, adding a qualitative layer where none might exist otherwise. Instead of relying solely on open-ended survey responses, you could create a kind of dialogue—even if it’s with artificial intelligence.

And then, even in our own workflows, I can see AI being useful—like uploading transcripts to surface insights we might have missed. But the role of the qualitative market researcher is safe, at least for now. Because what we do is human. What we do demands empathy. And you can’t get that from a robot.

Yeah Is that true though?

I think you can have something that approximates empathy—something that looks like it—but a machine can’t truly understand it. And if there’s no real understanding, then there’s no real insight.

If AI can’t break down human experiences in a meaningful way, then how can it translate them into something useful? It might collect the data, but it can’t fully grasp its implications or draw the kinds of connections that help a client understand what it means. That’s a fundamental limitation.

These machines are going to get smarter. They’ll get better at pattern recognition, at drawing certain kinds of connections. But at the end of the day, they aren’t human—so they can’t understand human. They can analyze, process, and categorize, but there’s still that deeper why—the underlying human motivation—that remains elusive for AI.

And right now, the technology as it exists—these AI chat models—they don’t ask questions very well. That’s a limitation of LLMs at this stage. But we’ll see.Have you had any experience with them?

Yeah, I mean, I’ve been experimenting as much as possible. I’ve definitely benefited from uploading transcripts, interrogating the data, and playing around with different ways of extracting insights. That’s been useful. I’ve also explored synthetic users—interviewing AI-generated personas just to see what that looks like. I’ve tried to stay open and experimental in every way.But at the same time, I’ve had moments where it triggered a kind of existential crisis. Maybe clarifying, maybe not. It’s strange. It’s just… strange, you know? I think we’re all still trying to wrap our heads around it.

Convince me—why should I consider synthetic respondents? Because that’s one area where I just can’t see myself being open to it.

Oh yeah, I mean, I was just curious. It ties back to that bigger question: What do we actually do? What do I actually deliver to my client? If it’s just answers—data presented in a way that gives it context—then sure, a machine-learning rationale might make it seem valid. And some clients, honestly, they just want answers. They don’t care where they come from. I don’t see AI going away. It’s here, and we have to figure out how to engage with it. But in my experience, I haven’t had that wow moment where I thought, This changes everything. It’s more like, Holy shit, this is weird. I’ve run tests, and I think this is what you were talking about—when I read AI-generated responses, they never felt real. They weren’t wrong necessarily, but they lacked something. It was deeply subjective, but I just kept thinking, This isn’t actually qualitative data. It’s… something else. I don’t know what this is. This is synthetic. It’s a different form of data. We need a whole new set of expectations: What is it? What can it do? What can it not do? It looks like real human qualitative data, but it’s not. It’s something else entirely. That’s the uncanny valley of it—it’s totally passable, yet it lacks any of the vitality or humanity that we, as researchers, traffic in. The squishiest of squish…

Emotions, memories, lived experiences, real-world touchpoints. Now, I could see a future where we’re interviewing AI agents designed for specific consumers—because in some cases, they are going to be the binary consumer. But yeah—sorry, go ahead.

Oh, no, that’s fine. I feel like I’m getting lost in my own thoughts. This stuff just…

And, you know, I keep thinking about the typical PowerPoint deliverable. That’s actually an exciting space for AI—the ability for deliverables to become more of a living product. Imagine feeding in all your insights, uploading the transcript, and then letting any stakeholder interrogate the research—talk to a bot about it in real time. That’s cool.

Jesse, we’re out of time, but I just want to say thank you. This has been such a fun conversation with a fellow researcher, and I really appreciate you sharing your time and experience.

Peter, my brother-in-arms. Thank you—I appreciate this time. Yeah, let’s team up sometime soon. Let’s double-mod.

That’d be great.

Take care.

Bye.