When the public thinks taxes, they probably go to spreadsheets, accountants sitting in windowless rooms using a calculator and the IRS scaries. What may not spring immediately to mind? An AI-generated woman with lettuce for hair. But that’s the joy that Lettuce Financial, a new tax and accounting start-up, brings to the world. We spoke to their head of marketing, Gabrielle Tenaglia, their head of brand and content marketing, Kim Fredkin and the two creative directors who made it all happen, Ronnie Allman and David Roth, to find out how taxes, Lettuceheads and musicals aligned to create a brand that’s anything but dull.

What does Lettuce exist to do?

Gabrielle Tenaglia: Lettuce automates taxes and accounting for businesses of one: Fractionals, freelancers, contractors. Anyone who runs a solo business. Every time a client or a customer pays them, we automatically calculate what they owe in federal and state taxes, set it aside, and pay it for them. Most importantly, we set them up with something called an S Corp, which is a tax status that can save them $10,000 or more. If you are a business-of-one it can be complex to manage an S Corp, so, traditionally, only companies with more employees took advantage of it. But because of technology, we're making it more accessible to this business-of-one audience.

We focus on this audience specifically, because almost everyone who works for themselves in the United States is overpaying their taxes today. The US tax system is really built to give all the advantages to W2 employees and corporations, but by being an S Corp, self-employed people can save thousands in the self-employment tax that they owe. The challenge is that S Corps are complex to run. It's bureaucratic. We automate all that with software.

What is Lettuce challenging for that audience?

Gabrielle Tenaglia: The first is that taxes have to be hard and stressful. It's not true, and especially with technology, these things can be much easier. The second thing is that taxes have to be mysterious, and that you can never really know the right thing to do. There's a lot of people who are just overwhelmed by this. And the third thing we challenge, is the culture out there around taxes that says that if you just find the secret hack, you're going to save all the money. This is not a secret hack. It's a legit way to save on taxes that the government developed, because they want small businesses to succeed. It's not a secret. It can be hard to do, but the secrets and hacks can actually get you in trouble. The tax category has this veneer of expertise that puts up all these barriers for people, and so they're either too intimidated to engage, and they avoid it, or it feels stressful. There's a knowledge and language barrier, but it doesn't have to be like that.

Given all these barriers, how are you getting people to engage?

Kim Fredkin: The biggest learning we’ve had is that if we're not pushing the envelope on both our message and our creative approach on how we're showing up, we are invisible. When you look at the data, we are just lost in the sea of bigger brands that do something similar to what we're doing. So whether it is with our Creator content or this innovative AI work that we're doing, we have to have some mechanism to grab attention, because either the creative is so quirky and interesting or the delivery is a little bit over the top. Where we're seeing the best results is when we really work to stand out. That’s the number one thing that's guiding a lot of the decisions we're making moving forward.

We really can't play it safe in this category, at the size we are and with the budgets that we have. The really ambitious goals are set at the CEO and executive level, but from a marketing perspective, it requires big swings to do it. And that includes both the creative and the media, where we're putting significant investments around some of this.

In a very traditional (and some might say dull) category like taxes, where did the idea for the creative come from?

Gabrielle Tenaglia: I wrote a brief that basically said, “Make taxes more interesting.” That's the brief. And it came out of the [Cost of Dull] work. It was June, no one wanted to talk about taxes. So, we knew we needed to do something that was different to get people's attention.

Ronnie Allman: A lot of how we work is purely out of curiosity for the category. What do we not know? What do we know? Can those two worlds collide? What is the perception of the audience and what they may not know, and then always trying to find a nugget of humour in there to make it human. What are we selling? What are we trying to do? What does our audience want from us and then how can we make them smile at the end of the day?

David Roth: I don't think there are dull categories. I think there are dull people. If you were to talk to someone about, “oh, we just won a big insurance client in the early 90s.” That doesn't sound exciting, right? But what is probably the most creative, fun category right now, at least in TV advertising — it's all the insurance brands. They're one of the few places for visual spectacle. They're all extremely memorable. They're all pushing each other to be funny. And it's become a comedy writer category and has turned some agencies into professional comedy agencies using professional comedians…if you treat it like it's a dull category, then you might come up with dull work.

In terms of Lettuce, one of the things was that when you're an early brand that no one knows about, it's just about name recognition. You have to hit that home a little bit more than if you're trying to really get into the weeds of certain benefits. Obviously, we need to talk about certain things like S Corp but in terms of specific executions, it’s just getting people to remember the name first so that’s why we use all the vegetable puns in the song.

Ronnie Allman: Sometimes we just have to be straightforward and talk about the brand the way it needs to be talked about, without this huge creative bubble around it. But the Lettuceheads let us do some of that heavy lifting to engage people, and that's always when it's fun and exciting to me because we can talk about something super boring and straight like we have to sometimes, but then with that extra layer on top, it makes it funny and new every time.

How did it come to be so musical?

Ronnie Allman: Early on, when Lettuce reached out, one of the first things they said was that they would love to make a musical – eventually.

Gabrielle Tenaglia: As soon as I started working on Lettuce, I just thought, “oh, the world of taxes needs a musical.” But I never imagined that we could really do this, at least in the near term, because producing something like that is complex and expensive. It would make zero sense. So, the first thing that we made at Lettuce was an explainer video. We launched during tax season, and you get the natural traffic because people are thinking about taxes. But after April 15th, no one really wanted to think about taxes — it became harder and harder for us to get traction and traffic. We tried other things but they just weren’t working. Just by chance, right around that time, I saw David and his partner Ronnie posting some stuff on LinkedIn just playing around with AI — like, a musical with a yeti singing about Yeti. So, I wrote them a note.

Ronnie Allman: We were like, well, why don't we just make [a musical] right now? I was already playing with a lot of AI tools like Suno where you type in lyrics, and within 20 seconds, you have two or three songs so you can test if it's going to be good, but then the AI part of the visuals came a little bit later. We knew we could get the music to do it, and we knew we could write the script to make the music funny. But then pairing that with visuals, I think it just came naturally with, oh, it's Lettuce. There's a lettuce head. If someone's singing, I guess it should be a woman with a lettuce head singing. It wasn't that big of a creative leap. It was just sitting right there. We knew we had to play with it, and we knew it would be a sing along because there are things that you have to do on Meta like put subtitles at the bottom. So, it's a musical, so those are your subtitles. So, let's make it a little sing along.

When people think taxes, they don’t generally think funny or silly. How did you know this was the right strategy to try out?

Gabrielle Tenaglia: Look, we have a piece of content that we're still using that’s the straight version of this, essentially. It was not made with AI, it was shot practically. It has some humorous moments, but it's a product explainer — it has screenshots and all the expected things. It was doing some work for us, but not enough.

The definition of crazy is doing the same thing and expecting different results — we could have done more straight stuff, but it didn't feel like to me that if we just tweaked the person, or we tweaked the line about S Corps, that that would make a difference. We needed to take a bigger step.

But I want to be really clear about this, and this is what I think is important for other brands who are trying to be more interesting to understand – using AI enabled us to do this piece. We never would have picked this out of the work that was presented if I had to choose just one [idea to move forward with]. We were in a seed stage at the time with some early customers. I could not have gone to my CEO in any reasonable way and said, “We should make this musical. This is what we should be spending our marketing dollars on.” It wouldn't have happened. But being able to do it this way with AI gave us so much more room for experimentation — and the lesson and the value we got from that experimentation is huge.

David Roth: One of the interesting things about the brief was that Gabrielle and Kim really wanted a range of ideas and executions. So, we would think of something and then do the opposite or just choose something because it was so different from the last thing that we had done. The fact that they're doing all the data testing and figuring out what's effective and just letting us even do something that is outside of our own taste – it's great, because it’s all for research. It's all for data. It's all to learn. So, it doesn’t have to be my favourite. Some of the most effective things aren't necessarily your favourite. It's interesting just to learn, or just do something for the sake of “let's just get it out there,” because with AI it costs basically nothing.

It's all exciting. As a creative, normally you're like, “Oh, this got made because this person believed in it, and this thing didn't get made.” With this, everything gets made. Gabrielle talked to the CEO Ran Harpaz and he said, “Let's make all of it.” — and then we did make all of it. That's never happened to me before.

Kim Fredkin: Most places say they want you to take risks and learn, but it's really within a very narrow set of parameters of the brand as they think they know it — there's not a lot of room to push. I think it's the opposite here at Lettuce: the mentality here is really one of test and learn. Of course, everything that we do needs to be grounded in how we think it's going to drive the business, but there really is a focus on “Let's put it in market, and let's let the customer tell us.”

Gabrielle Tenaglia: Ran, our CEO, really deserves so much credit for creating a culture where experimentation and learning are a top priority. He has really prioritised the strategy of: launch it, get it out there, learn something and then go make it better. He would rather try something and learn that it doesn't work than spend time and money crafting and making it perfect and then launching only to find out it doesn't work. And I think, he's learned that from experience. We were talking about some choices we had around media, and he told the team, “I see that you're telling me I could get x incremental business if I spent this money. I would rather you come back to me with an idea about how we could 3x or 4x what we're doing in this specific place, and try it and fail, than for us to conservatively try and do this incremental thing that we're pretty sure we could do.” And I don't think we could do this without that baseline cultural expectation.

Do you think this process is replicable at other companies or for other campaigns? What’s your advice for other brands who want to use AI to get to more interesting work?

Ronnie Allman: Is it replicable? Yes, but I think that since this is such a new creative process, being open minded from the very start is how you end up with work like this. If you're at other big agencies and legacy agencies, they have a whole process, and they like to do things the way they've been doing them. And that gets in the way a lot of times. I love working with other artists, musicians and sound houses too, but you don't need that all the time. And David and I are artists too — what I do in creating these and what he writes in these songs, that's art to us. We're really putting our artistic values into this work. We try to make it the best we can with the tools that are emerging every single day.

David Roth: What used to happen was an agency cloistering up and working for two months on something and then presenting this banquet of work, and then getting feedback, and then taking two weeks to get more feedback, and then two more months to come back. Now it’s “Get in the room with us.” We got nothing to hide – open kimono, as they say. We're happy to brainstorm – it's fun to brainstorm with Gabrielle and Kim and Ronnie all in one room. Just get it done.

And that stuff is so much more fun when it's quick, when everyone feels involved. When you're part of the process, where we're not hiding. We're not trying to say “This only took 10 minutes, so it's not valuable.” It's more like, it took 10 minutes because Ronnie spent two years learning 17 programs. So, as long as everyone respects and appreciates that, then we're good.

Gabrielle Tenaglia: I've posted this work in a couple of marketing communities that I'm in, and other CMOs or people who have more business-side (or not creative) roles will say, “Wow! Teach me how to do that.” And I'm very clear with them: I can't do this. If I were the one doing this, these ads would be bad. The reason why this is any good at all is because I have a really talented creative team who know how to make ads doing this work with AI. Maybe someday someone like me, without any great creative ideas, will be able to execute something like this. But right now, the value comes from the skillset that these guys have as creatives and artists being applied here.

I think the backlash is inevitable, but I don't think we're going back. Marketing budgets are not getting bigger. It's not going to get easier to figure out what works. You can do boring stuff, or you can figure out how to do more interesting stuff, and this is the path.

“The world of taxes needs a musical”: Lettuce Financial