After building hundreds of startup brands, Arielle Jackson shares 6 early marketing missteps to avoid

Brett Berson: Well, thank you so much for joining us. 

Arielle Jackson: Thanks for having me. 

Brett Berson: So we're going to spend our time together exploring a bunch of the different missteps that you've noticed in, in collaborating and supporting at this point, probably hundreds of companies over the last decade, as it relates to marketing and positioning. And so I thought we could start by kind of exploring the, the challenges or missteps you see in the area of category creation.

Arielle Jackson: Sure. Well, one of the first missteps is just not thinking about it at all. I would say most of the early stage startup founders I work with, and you mentioned it's been hundreds. I just counted this year. It was 71 in 2021 alone. So it's definitely hundreds at this point. Um, and the thing I see the most is that people don't even think about it.

They don't try to define which category they're playing in, or like pick the arena, plant that in their target audiences mind, it's not a thoughtful process or it's not even a consideration. And one of the things that we do at first round and in my consultant, It's really forced founders to define which category they're playing in.

And as soon as you bring up category selection to a founder, they almost always want to create a new category if you give them that as a choice. But considering the alternatives and making a thoughtful decision is really important. there's three choices. One is you can play in an existing category. I worked on Gmail early on, and one of the things we did is we decided to play in free web mail.

You know, at the time it was Yahoo mail and Hotmail, or think about Amazon. They decided to play in retail bookseller, and sometimes choosing a category. That's an existing one is not a bad choice. The other choice would be to modify an existing category. And this is when you take a category that exists, that people have a good understanding of my favorite example actually is nest and the learning thermostat.

So before they came out with learning thermostats, everyone knew what a thermostat was. And no one had thought about it for 20 years and thermostats were boring and they just sat on your wall and, you know, kind of try to control the temperature. Um, and they didn't really do much else. And nest had this brilliant idea to just add the word, learning to the word thermostat and carve out a sub segment of that category to play in that they could really own.

And now, you know, you never heard the word learning next to the word thermostat. Now Honeywell and eco bee, and lots of other players have learning thermostats, but they really cemented that idea of a thermostat could be something new and sexy and something desirable again, as opposed to something you never thought about just by adding those words together.

I think pros did a good job with this too. And more recent example with custom shampoo. I never thought of custom shampoo before. You know, I definitely have shampoo and I know what it is. And I really don't think about it much. And all of a sudden you can add a word like custom to a word like shampoo and now pros owns it.

And I'm sure there's a million copycats too. And then your third choice when it comes to category is to create a new one. Creating a new one is great. Play bigger. Was this really popular book a few years ago, and actually it's kind of meta, they rebranded positioning and called it category creation.

And, uh, they were really big on saying that the players and who won were the ones who defined a new category, which I think is Why, founders are so big on category creation now. And there's a lot of great examples where people have branded, um, a new category totally out of the blue. I think from a B2B perspective, Marketa actually has, uh, a modified category, but Gainsight did this really well with customer success.

They kind of were the pioneers there. Uh, but if you look at a lot of the B2B examples that you think of is category creation, they're actually modifying a new category. Like Marquetto. I mentioned, um, we have some at first round that I've worked with like Sprague with continuous research or Wolf with a global collegiate university collegiate university existed, but never a global one.

So that idea of taking a modifier and putting it with an existing category to really carve out a place in which you can play and potentially win. 

Brett Berson: why why is establishing this early on useful or important?

Arielle Jackson: I think it's the same reason that positioning is really useful early on. And that reason is that if you don't define the space in which you're playing, your audience will either have to do it for you and they'll do eight different versions of it. And it won't be clear. And even internally, you'll have people saying you are eight different things, and it's not clear internally.

And the earlier you do this work and that you define here's who we are. Here's what we stand for. Here's How we play, where we play, why we play, um, the better it is both for internal alignment for having everyone marching to the same beat. And then also for really occupying that space in your target.

Customer's mind if pros hadn't said custom shampoo. When I talked about pros to someone else, I probably wouldn't use those words. I'd use whatever words I thought of. And when they give me that shorthand, it's much easier for their message to spread and spread in the way they want it to spread, as opposed to the way that, 8 million different people understand it.

Brett Berson: How should founders think about navigating you that starting point of which approach of the three choices to take.

Arielle Jackson: Well, one thing we do. We do this exercise with first round companies and otherwise is we kind of start with, what do you do? We just have the founders explain, Who are you? And what do you do as a company? And once we understand a little bit more about what it is, we then can really be intentional about making some choices.

And the way that we make choices is we explore all the alternatives. And sometimes it's very intuitive. I'll give an example of Eero, which is a first round company I worked with for a long time. And we made a list of all the existing categories they're there in the home wifi space.

And we said, okay, well, they could be a router. They could be a modern router. They could be a new kind of router, a premium router. Oh, what could they be if they were something new? And we really just brainstorm what are all the existing categories? How could we modify the existing category? Like add the word premium next to router.

And then how could we potentially create a new category here? And we did a brainstorm. And one of the items on the list of the brainstorm was home wifi system. There are enterprise wifi systems, those existed at the time, but they were never built for a home market. And Nick, the CEO just like latched onto that, loved it.

It was super intuitive. He understood the challenges of creating a new category. It takes time. It's expensive. You have to say the same thing over and over and over again until people have. Uh, if you look at their packaging, it literally has the IRO logo locked up with home wifi system on it, just like nested with learning thermostat, you cement that category along with your brand.

And now if you go to best buy there's an aisle of home wifi systems. And Google is probably the biggest player there, but it was an investment. And for Nick, it was pretty intuitive. That that was the way he wanted to go. Um, for other founders, sometimes there's a little bit of user research that gets done.

Let's hear how our customers are talking about it. Sometimes there's market research that gets done, you know, how big is the shampoo category and how could we carve this out? And would we be the kind of company we wanted to be? If we owned a subset of it, uh, we're doing it right now. There's a first round company who is in the skincare space and I'm not going to go into the details because they're not out yet, but we did a brainstorm there and they actually worked with an agency who helped here too, and came up with this modifier to skincare.

That's just so good for them. And as soon as it was said, I had an eyes light up moment. And so did a bunch of people working on this brand. And we're going so far with them. They're, they're trademarking that term, the modifier with the word skincare so that they can really go after this, modification of the skincare category and own it.

And so I would say it's, you know, like many things marketing, it's partially an art and partially a science. And I think a little more art and intuition goes here than science, it also has to do with the business you're in. If you're a B2B business, you're selling to a buyer who has budget for existing categories.

And so if you're a market research tool, let's take.

spread, right? They, they went with continuous research. If you brand yourself totally outside of the category of research, it's really hard to get budget from the people who manage the market research budget. But if you're continuous research, okay, well that fits In her market research.

 It's a new kind of research, but we understand that it goes for our research budget. So for B2B companies who are selling into customers who have existing budgets, it's often really nice to play in an existing category or modify a new one because they know that they have the budget to buy that category.

Brett Berson: In what cases I can see the, the way that you articulated the difference between modifying a category and creating a category and some of the trade-offs between the two of them. I it's a little bit more unclear. When does it make sense? Just to sort of use the existing category.

Arielle Jackson: Yeah. So if you use an existing category, you have to think about whether you could someday when that category. So when Gmail said we're going to play in free web mail, we really thought that we could beat out all the other people playing in that space and build a better version of free web mail. If you are pros, let's going back to the shampoo example.

They may not think that they could beat out every analysis and own the shampoo category, but they can own the custom shampoo category. And sometimes you could outgrow the modification like nest out, grew learning thermostat, and now they're in home automation or smart home devices. There's something bigger than that for the company.

The product is still learning thermostat. Um, but I think they went saying we want to modify an existing category and really own this mind share. And then that, that piece of the category is actually going to grow as a segment of the full category. with Wolf, which is an education company in the first round portfolio, when we, we brainstormed a lot, when they came and started the process with us, we were thinking they might be an API for accreditation.

That's functionally a lot of what they do. But when we thought about what they were trying to do, and we worked on their purpose, we came back to this idea of, they actually are a new kind of universe. And so we did the brainstorm of new and existing and creating a modification of an existing. And one of the inspirations for Wolf is, um, universities systems like the university of California, the university of London, Oxford, where there's many colleges that make up one university, but each college feels and operates fairly independently, but gets all the benefits of being part of a major university.

And that was kind of the inspiration of, could you make something like that for the modern age and the idea behind Wolf as well in the future, you'll take some classes online and then you might take some classes in India and then you might take some classes in Australia, wherever you want to go, you can just travel and be virtual and learn from the best people in the world.

And so this idea of a global collegiate university carving out, well, They're not going to own collegiate university. They're not going to take it over from UC and Oxford and university of London. But they're not really competitors. Those inspirations never would claim that they're global.

And so Wolf can go in and say, well, we're going to say, we're the global version of those. I don't know if that exactly answers your question about like, when and how, but I would say like, will you ever win the category? Do you think it's a reasonable and plausible thing that you will win the cat. And then you play in the existing one.

If you don't think it's reasonable, how can you carve out from the existing category? So that there's a sub segment of it, whether it's a new sub segment, like learning thermostat, custom shampoo, continuous research, or I always think about this example.

It's so dated, but it's a really good one in the book positioning, which is one of my favorite books. I always talk about this book. it dates itself cause the book is really old, but it's still quite relevant. And they talk about Virginia Slims and Virginia Slims is a cigarette, just like all of the other cigarettes for women.

And what did they do? They said, well, we're not going to compete against Marlboro. And I don't even know all the cigarette brands that played at the time, but what we think we can do is we can win. If we make a cigarette that's exactly for women. And so they said that was their modification of the cigarette category.

and they went on to for a long time, be the number one product that women purchased in the cigarette category. 

Brett Berson: How do you know, after you've done this work, if what your doing is working, as it relates to that the approach you've taken to, to category creation modification, et cetera.

Arielle Jackson: Yeah, it takes a while. I mean, it takes, especially if you're modifying or creating a new category, you're not going to get a read on this in a week or two, but there Are ways that you can get early reads. And I would say early reads are, look at the press articles that come out when you first announced, are they using the same category that you're using?

Look at the way your reviewers are reviewing your product. Are they reviewing it and using your category name, look at the way your users are talking about it. Are they using that name too? And I think if you're very, very consistent in the way that you talk about your product and you're consistent in everything from your website to your customer support, to your packaging, to your interviews that you give, if all of those touch points reinforce the same message, it should feel boring to you.

 I bet Nick from Eero was so sick of saying home wifi system, but it worked. And you know, it works when everyone else starts saying it too. And it really works when other people start saying it. When, when competitors enter your space and use your same category name, then you know, it's working.

Brett Berson: How about the idea of this approach to category definition at the company level versus the product.

Arielle Jackson: yeah. So early on when a startup is, you know, at a seed stage or even pre-seed, they usually have one product. And so the company positioning and the product.

positioning are very similar. I would say they should be the same. So if you think about square in the early days, square was the little piece of hardware that you plugged into the headphone Jack on your phone.

That was the shape of a square. And it was the square card reader. That was the company that was the product. Um, there was an app that went alongside it. So square actually ran into some issues with this. When they wanted square to stand for more than just the card reader, they had multiple product lines.

I worked on the square stand, for example. And so we needed then square to become the parent company name, the square card reader, to become the hardware, the square stand, to become the other hardware. And then there was the square register app they've since gotten even further. You see all these, all these companies now, you know, from Facebook becoming Mehta and square becoming block.

And, um, lots of companies trying to say, well, we outgrew that. And so the same thing can happen with your category. Like in the early days of nest, the word learning thermostat was locked up with the nest logo and nest was the learning thermostat. And once they came out with a, um, smoke detector and now they have cameras and other products, you don't really want the nest brand to be associated with the category of learning thermostat anymore.

But in the first 18 months of company building, which is where I like to focus the companies that I work with at least, and where first-round focuses, the product positioning, the product category you choose to play in really is the companies. And then if you outgrow it over time as nested or a square, did you evolve, but it shouldn't feel like a pivot.

It should feel like an evolution you've written about this, but I want it to give the sort of the cliff notes version of the process that you hinted at at the start of our conversation to actually do this work. But does the process look somewhat similar for the work that you would do at the product level?

 let's say you launch your fifth product and the work you do around this, this topic of category design. Is it, is it quite similar to, at the very beginning when you're sort of doing it for the company and the initial product team?

Arielle Jackson: Yeah, I think it's really similar. I mean, I did this at square. I think we were like 150 people. Um, I was acting as a product marketer for the launch of their second hardware product and we did product positioning for the square stand and the way we positioned it, it was much more like a cash register than like mobile payment acceptance.

And so, yeah, it's the same process for a new product. Once you have multiple products, you often have company level positioning and then you have product positioning for each one of your products and they all have to play nice together. But the process that you run through is quite similar. 

Brett Berson: So looping back to what I was just sort of mentioning, uh, you've shared some of your frameworks and ideas around how to actually do this work, but I was hoping you could kind of give a quick summary and talk about it, maybe in a company that you've worked with or kind of the end to end process.

And a founder comes here and says, Hey, I actually do want to take this seriously. What, what should this process look like to land on, your overall, uh, positioning.

Arielle Jackson: Sure. So I've been using a pretty similar process for a number of years now, and actually just taught a course through Maven. That was a way to do the work that I've been doing with first round companies. One-on-one in more of a one to many, um, system, and it was a very similar process and the way that we ran through things in the course and the way that we run through things.

When I do engagements with first round companies, we always start with the company purpose. We start with, why are you here? And why should people care? And we define the company's purpose first. Um, there's been a little bit of backlash onto purpose and like, does it really matter? And do people care, it really matters as far as rallying your internal employees, if nothing else, but I believe it matters for everything.

Um, and so no one wants to remember two to three things like a mission and a vision and a purpose. We really distill it to one statement and we make a single purpose statement that makes people want to root for you and helps you make company decisions. 

The second thing we do is product positioning and product positioning is okay. So you're a company and you have this reason for being, and it's well articulated. And now, well, what's the product that you have. What is the thing that's coming to market? So the purpose exists on a 10 year horizon and your product positioning exists more on like an 18 month horizon.

So from the time, you know, usually you're a pre-launched company till, um, around the time that you would maybe be raising your series a that's like roughly an 18 month period, these days it's, it's probably even shorter than that, but that's the way I like to think about it. And this is what product do you have?

What does it do? What category is it? Why should people care? who are you playing up against? Who's the bad guy, you know, who loses when you win? uh, sometimes the, the loser is not another competitor and other startup, but an old way of doing things. And then we talk about your differentiation and your differentiation is what makes you unique that the competing alternative can not claim that also helps me believe the benefit.

And then step three is defining the company's personality. And the personality is how you show up, particularly in written copy, but also informs visual identity. Um, and sort of the feeling you get from the company. If the company were a person, what would it be like?

Arielle Jackson: And it gets everyone writing in the same way. And delivering a consistent look and feel and a consistent voice. And so those are like, for me, that's the minimum viable brand strategy. And one thing we didn't touch on that much in, in the positioning.

section is we really focus on who are you for And who you're for is I like to think of it as like concentric circles of audience.

So you have your Tam, your total addressable market. That's the biggest circle of people that you would ever really address and then narrowing in from there. So that each circle is contained in the larger one before it, till we get to an individual model user. And that's really who we're speaking to with our communication.

Brett Berson: then how did these different work streams then flow into this concept of category definition?

Arielle Jackson: yeah. A category definition is a part of positioning. So when we do positioning, one of the things that we work on, we work on your audience. We work on your benefit, your category, what you're up against and how you're different. Those are sort of all the components that go into positioning. And so category definition, I want you to be able to say company X is a Y, that does Z.

So what the is the Y it's a noun and you're playing in that now. And just like Gmail played in free web mail. And Amazon played in retail, bookseller, and Uber and Lyft played in rideshare. where are you playing? Give me a mental model for what I should think about when I think about your company.

And one of the things that comes up a lot, the first time I meet with founders, it usually takes them the half of the first meeting. So it's like 30 minutes to explain to me what the company does. And we would waste 30 minutes of a, what could have been an hour long working session with me, trying to understand what the company does.

So now one of the things I do when I work with a company is I give them a worksheet and force them to answer the stuff in written language. And then I can read it and come armed with the questions, um, that I have about the company. So it forces you to write down what do you do in plain English?

And we workshop off that worksheet. ,

Brett Berson: And in this sort of early work of figuring out things like how to articulate your purpose. Is it, is it about volume of ideas and you start with just the most expansive list possible, and then it's a process of editing or, or at a more detailed level in each one of these work streams, what sort of the ideal way for a team, um, to go after them?

Arielle Jackson: sure. So taking purpose as an example, um, I have a framework for each of these things that I like to use, because it's really hard just to be like, good luck, brainstorm your purpose. And you'll know when you get there. Um, for purpose in particular, I didn't invent the framework. I borrowed it from Ogilvy and their purpose framework is called the big ideal.

And it's an exercise where you brainstorm all the things that are happening in the world that are relevant to you as a company. Um, I'll give you an example. We did this with ever-growing, which is a first round company. Uh, recently they just announced, and they're playing in the space of global warming and climate change.

And we made a long list of all the things that were relevant to their company. So it was everything from, um, I want to make changes to the way. That I know I can impact the carbon that I'm putting into the atmosphere, but everything I do feels like a drop in the bucket. So the things that your users might be saying, or that people might be saying to ideas like, um, wind and, uh, solar are sort of more established, uh, ways to have an impact on this, whereas carbon offsets or something that doesn't really feel as understood.

Uh, and ultimately we made this long list. It probably had, I don't know, 30 things on it. And the, the one we chose for the cultural tension or the what's happening in the world today, the Zeit Geist around the space they're playing was climate dynamism. And that idea captured, it feels like anything I do.

Isn't going to change the course of the destruction we're causing to our earth. It feels like everything I do is a drop in the bucket. Even if we made drastic changes at a policy level or a government level or a technology level, we're probably still fucked. And so that idea of climate dynamism was really what we were trying to tap into.

And then, so that long list goes on one side of the paper or a whiteboard or Google doc. And on the other side is your brand's best self. So when you do everything you say you're going to do. What does it look like? And so we came up again with a list of 25 or 30 ideas. This is, you know, w this was a brainstorm over zoom with the founders, but it's great on a whiteboard.

Uh post-its however you like to brainstorm. And that side of the page had like, oh, well, we're going to slow the warming of, of, uh, our planet, or, um, we're going to fund projects that discover new ways of capturing carbon. Uh, and so we had all these different ways of saying it. And ultimately we got to one that said, we're going to fund every project that removes CO2 from the atmosphere.

And that sounded like, oh, okay. We, we all had that eyes light up moment. And it was so on the left-hand side was climate doom ism on the right-hand side was this idea of funding, every project that removes CO2 from the atmosphere. And then at the intersection of those two ideas, we try to finish this statement for ever-growing.

The world would be a better place if this is all Ogilvy's framework, They did it for dove was a great example where they came up with this, um, w if women could feel good about their bodies for dove soap. And so we're doing the same exact process for, you know, a seed stage startup today and forever grow.

Brett Berson: We did this and, and with those ideas, and then we do another brainstorm. How would the world be a better place? And, you know, came up with probably a shorter list there, but it's still a, a decent one. And then we did a sort of second one where we just said we exist too. And we finished that sentence and we did a little brainstorm there. in the topics we've explored thus farHave you changed your mind or change the way that you approach either the tactics or the overall set of strategies that, that you've shared thus far?

Arielle Jackson: Um, I think it's working with so many companies over so many years has really just cemented getting the fundamentals right early on. So I think I do these exercises and I've come up with new ones and borrowed new ones and frameworks. And I think the more you give people structure to do things like brainstorm their purpose or think about their category, the more likely you are To land somewhere.

Good. Um, and so as far as changing the way I do it, I believe in it even more, I have some new tips and tricks and great examples and all of that, but I wouldn't say it's fundamentally shifted. I think it's because. Even more clear to me how, when you get this stuff right early on, it plays dividends. your website writes itself, right?

Your, your, your purpose is your about page, your product, positioning your category and benefit is your homepage. Your differentiation is you're usually how it works or your product details page. And rather than reinventing the wheel with every piece of marketing that you have to put out into the world, if you get these fundamentals right early on, that stuff becomes so much easier.

Brett Berson: To your point about tips and tricks in this sort of area, are there any more recent ones that we haven't discussed thus far

Arielle Jackson: Yeah, sure. So, um, I'll answer in two parts then some tips and tricks and some ex. So, on the purpose front, one of the tricks that I like to use is, let's say you're a 10 person company. And I asked all 10 people, why do you do what you do? Meaning your company, not your, your new individually.

And I get 10 different answers, right? Can we get a purpose where in three months, if I asked all 10 people, why it is you do what you do, I would get everyone saying the same thing. I worked at Google when it was, I think I joined at like 1300 people and every single person at the company. Google's mission is to organize the world's information and make it universally accessible and useful. And I recently worked with a founder, an ex Googler who left when they were 80,000 people.

And he said, still every single person there could say that. And that's pretty impressive to me. You know, you have a pretty good one when it really, has 80,000 people saying the same thing, 

 a lot of. Come to me with many catchphrases And, many little purpose statements or mission, vision values. and there's not that one statement.

 Once you have that purpose, there are a lot of ways that you use it.

Arielle Jackson: The first and foremost is always as a north star for decision-making. And if your purpose can't help you make decisions, it's not a good purpose.

I think ring did a great job with this. They exist to make neighborhoods safer for a long time. It was, uh, to reduce crime in neighborhoods and they shifted it to the positive, but it's basically the same idea.

And I heard Jamie, the CEO speak at a first round event a few years ago, and he talked so much about how that actually helped him make decisions and how that give him ammo to go to his board and push back on ideas that he wasn't happy with. sometimes it even goes so far. As tying that purpose back to product decisions you know, with ring again, they talked about the angle that the camera lens would capture. And 

If this is really about safety, what's the right camera angle. The second way you use it is to make people want to hear what else you have to say. So, I think Irving at Bowery does a pretty good job of this.

 is an indoor vertical farm. The purpose is to grow food for a better future. And for the first many years of the company, whenever he would talk to her for Porter, whenever he would speak at a conference, whenever he would be in front of an audience. He would introduce himself that way.

Arielle Jackson: Hi, I'm Irving. I'm the CEO of Bowery. We exist to grow food for a better future, not then launch into whatever it was specifically that he was going to talk about, but it was a great opener that kind of teased the idea of what the company is about and opened everyone's ears to, oh, what's food for a better future.

And tell me more, I want to learn more about the product that supports that vision. So I'm really big on having one, not a mission and a vision. Those often one is often about the financial gain of the company. Like what is the, what is the place we're going to get when we're successful? I think people care a lot less about that.

You can have your own internal goals. That's fine, but for external messaging, irrespective of financial gain, what is the change you want to see in the world? And that is really where I think a good purpose lies.

Brett Berson: And, and to be a little bit more precise. When you think about mission and vision, in what ways do you think that's similar to your idea of a succinct.

Arielle Jackson: I think you could probably say that a mission isn't quite similar to a purpose and that a vision or a vision one over the other is I always get confused about it. So I just kind of discard both of them and say, forget about both a purpose is what are you here to do irrespective of your own company's financial gain.

How are you going to make your mark on the world? 

Brett Berson: Are there any other examples that you think kind of really bring this idea to life

Arielle Jackson: Uh, lots of companies I've worked with are very early stage. Um, uh, as far as like successful companies that are out there, I think Nike has a great purpose. I can't remember the exact language, but it's quite good. I think, I think stripes is actually amazing to increase the GDP of the internet.

 it's not without financial gain for them because they get a cut of every little piece of GDP of the internet that they produce. But it's actually, it's beyond that, right? It's like if the payment rails of the internet were better, more commerce would happen on the internet.

Arielle Jackson: And our goal is to increase commerce that happens on the internet. So I think there's this really succinct. And I think people internally know it. Um, people externally know it, right. I, I, I can rattle that one off. Nike's was always so brilliant to bring inspiration and innovation to every athlete in the 

and everyone who has a body is an athlete? Is this yeah. 

Brett Berson: exactly. 

Arielle Jackson: Yeah, that's a really nice one. 

 So I think I've strayed a little bit from your question about tips and tricks but going back another tip is, um, the bar test. So this was a fun exercise to do in that Maven class. We actually role played it. So these were all early stage founders. A lot of them were bootstrapped and then some of them had already raised a seed. Uh, and all of them were trying to talk about their companies in a better way.

Um, so there's a two, two frameworks here I'll give. one is about the benefit. And the second one is this bar test, which kind of brings it all together. So on the topic of benefits, uh, Matt Lerner wrote a piece on the first round review recently about this. It was about language market fit, and he talked about how everyone wants to write the next, just do it or think different.

But Nike and apple had already built ubiquitous awareness and comprehension before then. So their ads were allowed to be elusive and they had earned that right over decades. And when you're an innovative little startup, you didn't yet. So you need to be really clear and functional until people understand what you.

And so this idea of going straight to emotional benefits, like adjust, do it, or I think different before a functional one is, is a misstep that I often see founders take. And so one of the things that we do is we look at, you know, how would you phrase your benefit if it was super duper, duper functional, like really boring, just, you know, I worked with loom and it was like record instantly shareable videos of your screen and cam like that is exactly what they do.

Um, or like Rupa, which is a first round company order track and get results from 20 lab companies in one place, super functional. Right. And so just focusing on what is the functional benefit before you get into the emotional one? And we play this game with the Cinderella spectrum, right? the story of Cinderella.

 she had fairy godmothers and they turned her pumpkin into a chariot. And that was the functional thing that happened. and on the super-duper emotional thing that happened that night was she went to a ball and all this stuff happened. And eventually she lived happily ever after.

Arielle Jackson: So living happily ever after is the very emotional benefit of the Cinderella story. And right in the middle is this sweet spot where she married a prince. And that was somewhere between the pumpkin turning into a chariot and living happily ever after. And so just like you do that brainstorm and you think about what are all the categories in which we could play the modifications to the category, the new categories we might create.

We do a similar brainstorm where we say, what are all the functional benefits we have? What are all the emotional benefits we have? And then what are the ones in between? And then I always encourage these early stage startups to focus more on the functional. And sometimes we nerd out with the Wayback machine and we look at some companies we admire and what were their functional benefits early on.

You can often look at their homepage and the benefit is the headline. So I'm a big Peloton fan and Peloton. If you go to the Wayback machine, it literally said, join studio, cycling classes from the comfort of your home. Like that's super duper functional. And before they could stay stuff like together, we go far, or, you know, self-actualization type, top of Maslow's hierarchy type, emotional benefits.

They had to have most of the people in their target audience understand. We were talking about joining studio, cycling classes from the comfort of my home. Um, and when you're doing that brainstorm and you get to the right functional benefit, but it also could have a little bit of like emotional evocations you'll end up using that benefit as the headline.

You know, Peloton did, or, um, Uber and Lyft get a ride from your phone in minutes. That was the language that they had. Um, and with Eero when we did it, our actual positioning statement, use the words, blanket your home in fast, reliable wifi. And for the first few years of the company, that was the homepage on the website, that word blanket kind of got to a little bit of the emotional, but really functionally.

It was saying, you know, get your home covered in good wifi. And that was the benefit. And that was what we put on the headline. , uh, but going back to sort of other frameworks to use, we love to use that Cinderella spectrum. I love to use that with founders.

And then the bar test is kind of putting it all together, And so we do this role-playing game where we say, okay, you're one happy user. Who's using your product and you're going to get a drink with your friend.

Who's also in that same target audience. And you're going to tell me about this new product. And so, I'll give a super technical example Qube costs, which is another first round company and, um, super technical company. And what, what would one happy user say to another?

Well, I use coop costs and it helped me monitor and reduce my Kubernetes spend. Okay. That that makes sense. And then you can get into, well, how does, how is it different? So the bar test is what was one happy user. Tell another. And that's your benefit? What were you doing before? That's your competing alternative and then how is it different?

And so the way we play this in the, in the bar test is, oh, Hey, I've been meaning to tell you about X, which is the company name. It's this new Y that Z it's this new category that has this benefit. And then the other person the uninitiated user has to ask, oh, cool. Tell me more.

Or, oh really? How, and then the second thing you say is, well, before we were blah, blah, blah, blah, blah, those you're competing alternative and this new product, blah, blah, blah, blah, blah. And that's the differentiator. And if it can't be said out loud, it's not done and needs to be written in a way where people would actually have that conversation.

And that was really fun in the Maven class to actually watch people doing this, like drop into the breakout rooms and hear people saying it and look at the way they change their language just to really make it more human and the way people talk. The more you can speak in plain English, the more likely you are for your messaging to be repeated by your audience, which is ultimately the goal You're trying to give your potential future users a way to talk about you and a way to spread your words.

And if your message uses words like enabling and leveraging people don't say that. And so you're going to have a mismatch between the way that your users talk and the way that you are showing up in the world.

Brett Berson: In, in sort of the second bucket of errors around going straight to emotional benefit before functional ones. How do you know if you're ready to try to take a crack at something that is more emotional after you've been hammering functional benefits for some period of time?

Arielle Jackson: Yeah. So I don't think there's like a hard and fast rule about this. I think it depends on your audience and it depends on, are you in a new category? Are you playing in an existing? It depends a lot on a number of factors, but one of the things that this is kind of like a back of the napkin, type, framework, but it takes until you have about 15% awareness to be understood, meaning to have gone mainstream.

And I'm not saying general population awareness, I'm saying awareness within your target market. And once you hit that, you were free to do more. you're free to expand beyond telling people, join studio, cycling classes from the comfort of your home and start going up that ladder of benefits into more of the emotional.

Um, and so I think tracking your awareness in your target audience, um, understanding, how much market share do you have? And once you're at a place where you're like, okay, our audience knows we exist, 

Um, you know, for Uber and Lyft. Who I did not work with, uh, when they were brand new, they had to say, get a ride from your phone in minutes because people didn't know what ride sharing was. They were creating a new category. Once the concept of ride sharing had gone kind of mainstream, they actually diverged and were able to go further up that Cinderella spectrum into more of the emotional territory.

And you saw Uber, uh, having more of this like black car, we're fancy, it's a way for you to flex and for Lyft, you know, where your friend with a car and kind of cheeky and in San Francisco, that happened pretty early on and nationally that took a little while and internationally as well. 

Brett Berson: So let's continue on and talk about this, uh, this sort of third, uh, area of missteps, which is, which is around not defining your foil or focusing too much on other startups and not the old way of doing things.

Arielle Jackson: Sure. So one part of positioning is what you're up against defining, what is your target audience doing today? And when I give founders this worksheet and I have them do their first pass, and one of the section says, you know, who else is playing in your space? What's your target audience doing today?

I would say seven to eight times out of 10. I get a list of competitors, other startups who are trying to solve a similar problem for a similar audience. And then after I talked to the founders and we kind of workshop this, what I learned is like, all of these startups are really early and nobody has great market share yet.

And they're all trying to make things better or approach a similar problem slightly different way. But really if you ask them, what is your audience doing today? It's not another one of those startups. It's really the old way of doing things or the status quo. So, um, I'll give a couple of examples. So there's a company in the first round community called ascend and they're an insurance technology company.

And when you got the list from the founders of who else is playing in the space. Kind of other startups. And then one thing on their list said, or paper checks and manual reconciliation. And what they do is they make it really easy for people who sell insurance to take in payments and then make sure all the money goes to the right place.

So whether you're a broker and you have to, um, pay the carrier or whether you're a carrier and you have to pay the broker, and it's a pretty complicated, there's, um, rev share for the distributor. And then, you know, the carrier gets the premium and maybe the end user wants to be on a payment plan.

So the, the money movement's fairly complicated and they make basically an API that makes that all happen automatically. And what they're up against is how most people pay for commercial insurance today, which is, with paper checks. And when you think about all the small businesses in America, they're paying their, you know, commercial liability policies with paper checks.

Nobody likes that. And it's really easy to make that the bad guy, as opposed to another startup who nobody even knows about yet. And it's really easy to come up with messaging that describes How much better ascend makes things for these insurance companies. When the bad guy has paper checks and all the hassles in the old way of doing things that these businesses do.

And a similar example, uh, kind of back to paper. I worked on Google calendar a long time ago. And we were about to launch Google calendar. This was like 2007 ish. And we were talking about, you know, the, at the time most people at Google were using or outlook or some other digital calendar, but most people in the world were using Fila faxes.

And so when we came out with Google calendar, rather than position it against like the small market share that these other tech solutions had, we really tried to position it against paper calendars. Those, you know, giant ones you had hanging in your kitchen, or, you know, I had a Filofax.

So that was a, that was a way to say, well, there's a better way of doing things. And we're talking to most people who are doing this on paper today. Um, we had another company composer, which is a first round company that launched recently. Um, they're they're in the FinTech space. And what they allow you to do is create a portfolio of hedge fund, like strategies so that you can invest, you know, your, your money in a way that's more like a hedge fund and less like stock-picking.

And today their, their audience, which has sent a sophisticated retail investors, people who approach investing from more of a systematic way than a, you know, I'm going to pick these three stocks because I happen to like these three companies, the way that they were doing this, they were struggling with Excel.

Not being able to learn Python in order to automate their trading strategies. And so when we were able to say, well, composer is a new kind of trading platform that lets you create a portfolio of hedge fund strategies. And unlike, struggling with Excel and Python, it has all these benefits but really it was about the old way of doing things, um, or mirror another first Sean company when they launched what they were up against.

 it wasn't another startup in the fitness space. What they were up against was trying to push yourself on your own and this a fitness company. So think about that. It, that way, just like what, what would your target user be doing today? What are they actually doing today?

Arielle Jackson: Not who else is playing in your space. What are the other five startups that you might want to track from a competitive perspective? It's still important to track them. you want to know what they're doing and what they're saying, but when you're messaging, I feel like founders over index on tracking competitors who are other startups and under index on the behavior that they're actually replacing that old way of doing things.

Brett Berson: Um, switching gears slightly. Um, is there, are there specific learnings or, um, approaches that you've seen most successful for technical founders doing this work? Or there may be traps or patterns that, uh, technical founders tend to have versus other types of founders. When they're trying to do this work at their company.

 I've worked with a number of technical companies, whether it's like a dev tool or, um, some infrastructure project, uh, I would say that the, the frameworks and the process we use is very much the same. And if you can't explain your product to me, a non-technical person, I took one CS class in college and it was not for me, but I have enough understanding, uh, that if you can explain it to me, it's, it's not explained well enough yet.

Arielle Jackson: And I work a lot with this guy, ed, who is our PR expert in residence at first round. And he always talks about when we're prepping founders for press explain it to me. Like I'm a board teenager, a board, but smart teenager. And so one trap that both B2B and technical founders fall into is, oh, well, you won't understand it because you know, you're not an engineer.

This is, this messaging is good. You just don't get it. And maybe sometimes they're right. But I would say more often than that if a board, but smart teenager can't understand what you do. You haven't explained it well enough. And that idea of, you know, we talked about jargon, like the words enables and leverages and all of those words, the same is true in a technical product.

You want to be able to explain it without relying on the jargon of the industry. And, coop costs was an example of this. It took me a little while to understand what Kubernetes is and, you know, but after like an hour, I can kind of get it. And then I have to be able to understand, you know, well, what does their product do?

And yes, you need some level of language that is deeper and speaks to somebody who's really an expert. And your model customer, who might be an expert in the space, but your first order messaging that here's what we are. Here's what we do. Here's why you should care. Has to be at a level where a smartboard teenager could get it.

Then once that door is opened, yes, you have like technical white papers or you have, a sales person who's really, well-versed in technical aspects of the product who can speak in the jargon once the person has expressed interest. 

And I think that trap of just getting into jargon right away, or getting into technical language right away and not, I don't want to say dumbing it down, but making it accessible. To somebody and making it interesting to them, to really making it a story. Um, you know, people go into like, here's my feature feature feature feature before saying like, well, here's your problem.

And here's what we can do for you. That will make that problem either go away or not matter, uh, or, minimize it to some degree. So really starting with, and even for a technical product, like what's the problem, what's the problem. And how does your audience address this problem today? And in some cases it's a problem.

They may not even realize they have, and You have to remind them of the problem. But for a lot of products, it comes down to like, what is the problem? How do you solve it better than what they're doing today?

Brett Berson: You just hit on kind of an interesting and interesting idea which is doing this work, uh, around a product where the customer knows they have this problem versus figuring out how to educate them, that they do in fact, have this problem. And then you're the ideal solution and I'd be interested.

Are there, are there tweaks or lessons learned around positioning a product when the problem is clear and you don't need to educate someone versus bringing them along the journey and, and helping them understand that they actually do have a.

Arielle Jackson: Yeah. If the problem is acute and people are looking for a solution to solve their problem. You've probably heard this, like, are you an Advil or a vitamin? Like if you're an Advil and my head is hurting and you're telling me, you'll reduce the pain in my head. I will pay to reduce the problem.

That's acute and I'm suffering. But if the problem is like not quite a vitamin, like a vitamin is like, you don't even really have a problem, but it would be good for you if you took this. But imagine a problem where it was like, oh, it's, in-between an, an Advil and a vitamin. It's like, kind of thing.

That's annoying me, but I've learned to live with it. And I'm kind of resigned to the fact that I have this problem. I had like an, an knee injury playing, high school sports. Not very well, but. I kind of just learned to live with the fact that like, I can't really jump higher and that's just something that I've resigned and learned to live with.

I'm not taking Advil for knee pain every day, but it's just kind of like an inconvenience in my life that I will never have a high jump. And if all of a sudden there was a product that would make me jump higher, if you reminded me of the fact that, oh, isn't it kind of a bummer that like, you can't really jump very high.

You you've brought up that pain in a. way that it can start feeling more acute, even if it's something I've learned to live with. So there's lots of examples here. Eero did this really well with, like, we all kind of learn to live with the fact that our wifi cut in and out and they had messaging.

That was pretty cute. At one point that talked about, you know, wouldn't you be mad if the other utilities that you run your home on, like water and electricity went out as much as your wifi did? Oh yeah, that's true. Like my water and my electricity. It's a big deal When those go out. But I learned to live with the fact that my wifi goes in and out every day.

So there are ways you can remind people of the problem and kind of bring it up for them. So it kind of think of it as like poking the problem Tell that story so that the problem feels like I need a solution, even if I was resigned to living with the problem prior to you reminding me. 

Brett Berson: When you think about the problem or the benefit, um, how do you think about trying to tie it back to something economic versus, uh, in a, you know, efficiency, a pain point and annoyance, and does that ever come up.

Arielle Jackson: Yeah. So a lot of benefits come down specifically in the B2B context to, you know, save time, save money. Like those are often benefits. they're very functional, um, but save time and save money. So that what, and so if you think about like a CRM for freelancers, yes, I could save time and I could save money if I did it.

But really as a human, like what would it open myself up to? Maybe it would, stop hunting down, contact information by searching your email, or what is this specific thing that I would get to stop doing that would free myself up to Do the things I love to do.

So, yes, there's, there's a lot of things come down to saving time and saving money. And you want to articulate like, which of those you do. But if you're only about saving time or saving money, you're probably not going to be that differentiated. And it can often be a race to the bottom, particularly if it's a save money thing, because it's just, well, someone else can do this cheaper.

And then now all of a sudden, like your competitor does it by. So I care less about save time and save money and like, how will you do that differently and better?

Brett Berson: Do you spend time thinking about how positioning fits into pricing?

Arielle Jackson: Um, sometimes, well, it depends. Okay. So if you're a B2B company and your pricing is kind of like still to be figured out, Meaning, you're going to launch, you have some sense of pricing, but sometimes we even launched companies without, uh, without a price, right?

Like you're launching a freemium version of your product. And right now it's just the freemium one, but you've announced that someday you'll have a pro version pricing. Isn't really core to positioning, um, at least for this first 18 months. But if you are going to be a premium product and your brand personality is, not the approachable, but more of the aspirational.

And then all of a sudden you come out with like discount pricing. It, those things don't go together. So like, you have to have some sense of your pricing, but I wouldn't say, um, we're very, very detailed in the pricing work when we do positioning. It's more like, is this expensive? Or is this not?

Um, with Eero, you know, yes, they could have been a premium router instead. They were a home wifi system. Their price point was higher than a lot of routers. And they were able to command a premium price in part, because they invented a new category that, had no anchor pricing. So they were able to come out at a higher price.

Brett Berson: yeah, I was interested in that. That's sort of what I was getting at how that connects, meaning if you know that your pricing is going to be more expensive than a similar type of product, how that ladders into the way that you approach this work.

Arielle Jackson: Oh, yeah, sure. So if you invent a new category, there's no anchors for how much that category costs. So, you know, I, I'm pretty good at the prices, right? Not like the actual game show, but I really pay attention to pricing. And if, you know, I'm like, okay, a gallon of milk. If it's organic, it's 5 99. If it's not, it's like, between two and 3 99.

And like, I know how much things cost. Some people don't really pay attention to that, but it's kind of nice to be someone who watches pricing because then I can kind of say, okay, well that price seems higher. That price seems low. Talk about like Peloton as an example, right? And I had a lifecycle bike before I had a Peloton.

The lifecycle bike was a way, way cheaper and didn't have a monthly subscription fee, but it did not let me join studio cycling classes from the comfort of my home. And once they anchor their product positioning to, this is more like the studio cycling classes that you take and you're paying 25 to $30 a pop for, or you're paying, some gym subscription for all of a sudden there, I think it's $39 monthly fee seems pretty reasonable, 

But if you anchor it against that lifecycle bike that I had, that was just like a dumb piece of hardware that really didn't do anything other than, track your heart rate. And your miles Peloton would have seen incredibly expensive and it's an expensive product, but they anchor it to the studio cycling class and not to the lifecycle bike 

So, Um, the category that you play it's back to that idea of like, what space are you trying to occupy in your audience's brain? And what are the associations that your audience has with that existing space? If you think about thermostats, like most people don't buy thermostats. Most people inherit the thermostats that are in their apartment or their home when they bought them.

But. Oh, I don't have a learning thermostat. Now, all of a sudden I'm like open to spending in order to get something that's new, as opposed to, I would only buy a thermostat before nest, if my thermostat broke and I needed one. And so they were able to say, okay, well, this is a different thing. This is gonna cost more than but it does something more to

 so moving on you, you talked about this a little bit earlier, um, but this idea that, brand style, uh, guidelines tend to focus on logos and fonts, um, versus personality and voice. And so I'm curious, kind of what you mean by that.

Arielle Jackson: Yeah. So that third area that we touched on, that I often work with founders on is personality and personality. I like to think of as an input to your visual design, just like your positioning and your purpose is also an input to your visual design. But oftentimes I work with founders who have either a placeholder identity visual identity, or may have already invested in one.

And I asked them, you know, can I, can I see the style guide or can I see what you have? And what they send me is often one of these, you know, simple PDFs that says like, here's our logo and here's our fonts and colors. And maybe here's our illustration or photography style. And almost never includes like, this is how we show up in written copy.

This is who we are. If we were a person, they kind of gloss over the personality and voice of the company, just in favor of, you know, fonts, colors, typography. And I think the best style guides are the most useful ones. Not only cover the visual direction of the identity, but also the tone and voice of the brand as well.

And so that exercise we do after we do purpose and positioning, we usually go and define personally. And there's a few frameworks I like to use here, but, um, the first one is talk about the five dimensions of brand personality. And this comes from Jennifer acres, it's academic work, analyzing a lot of big brands and showing that.

they really come down to five dimensions, which are sincerity competence, ruggedness sophistication, and excitement, and good brands brands that have a well articulated personality and a well understood brand spike in two of those five areas.

And so first we talk about, well, which areas of those dimensions does your brand spike in a lot of startups, spike in sincerity and competence. That tends to be a pretty predictable area to spike in. So then we talk about, okay, well, if those are your two areas? What would be your five personality attributes?

And we do a whole brainstorm where we write down like, Okay.

these are all the personality attributes that we have if our brand was a person. And then we pick the five that are the hardest working and the most different from each other. And we try to make sure that those have tension between them.

So if you tell me that you're approachable and helpful and kind of. And diligent and nice, like you've told me the same thing five times, or at least related things five times. and brands while you want to spike in these two dimensions. If all you are is like sincere and competent, you're pretty boring. And there are time and a place where you want to have a boring brand personality, but sometimes brands that are interesting actually have tension between their attributes.

And so if one of your attributes for example, is that you're like savvy an expert, but one of your attributes is that you're approachable and straightforward. That starts being interesting because those two attributes have some tension between them or one of them is that you're, you are nostalgic.

And one of them is that you're modern. Like it's kind of interesting that you can be both of those things. So we like to think about these five brand personality attributes as the five points of a star where the top of the star is the attribute that you really want to own. If you only had one adjective and then across from that point of the star to all the other legs of the star that are opposite from them, uh, there's tension between those.

So each of the words works really hard and each of the words has tension between the words on the opposing sides of the star. That's often how you create an interesting personality.

Brett Berson: So I wanted to wrap up by shifting gears a little bit and talking about some of the things that you've noticed that can go wrong as it relates to getting press in the early days. And so working across so many companies, what are some of the pitfalls that you tend to see?

Arielle Jackson: Okay. So a common one, and this is again for early stage companies, a common one is it's, you know, three days before X date or a week before X date and the founder emails we're launching three days from now. And that's just not going to happen, especially in today's world. So number one, not leaving enough time to do it right.

Uh, Number two. Having unrealistic expectations about who will want to cover you. So we're launching in three days and we want to be in the New York times or the wall street journal is a pretty common one.

Um, another is, I think we need a PR firm or help us find a PR firm. Again, we have three days to do it and we want the New York times that would be like the trifecta of mistakes. really the content one is not knowing even what the story is that you want written by yourself, not even having thought about what is the headline that we want out of this new cycle that we're trying to generate.

Um, so one of the things that I do, if someone says, oh, we're launching on X day, we say, okay, well one why and two, what's driving that date and do a little expectation setting both around the timeline and also around the type of coverage that a seed stage startup could expect to get in today's climate.

Um, so on the time front, I think if you have your positioning down, you really know how to talk about your company. You can get this done a lot faster, but if you don't have that done, that's the first step. The next step is preparing a launch communications document, which really articulates, like what is the ideal headline you're going for?

What is a realistic set of reporters who might be interested in writing about this? What is the news? And the news could be anything from. Uh, funding announcement to a product availability like product launch, reference customers, momentum, metrics, partnerships, anything that makes what you're doing newsworthy, and then thinking through what is the ideal headline?

When we announced, what do we mean? What do we want this reporter to say? And then preparing for what is our talking points? What are we saying in order to get that ideal headline and lastly, prepping for hard questions. So I want a founder to be super comfortable with any question or a Porter might give them.

And so we actually write down all the hard questions we think they could get way more than they actually get, and then prep them with answers that they then make their own and feel comfortable saying so that nothing will faze them. Like they expect any of these questions and they're prepared to answer them.

So a lot of it has to do with just getting prepared, um, matching what your story is about and the phase of company that you're at with the right reporter, who is interested in that topic and writes about that phases of company. we're working with a company in a certain vertical where they're.

Industry trade press that writes a lot about this, but it turns out they only cover unicorns when it comes to tech. And this company raised, you know, three, $4 million round. So it wasn't going to happen for them. Um, so just aligning like, well, who does cover this space and what are they writing about and go read what they wrote.

It you're much better off being informed about what does a reporter write? What style of coverage do they have, uh, then just going in it at it blind, do practice interviews too, like a really brief media training. We don't do a full-blown media training. I mean, I I've done the style of media training where you get recorded in front of a camera, and then you have to watch yourself and that's terrible, but very effective to have to watch yourself, give a talk on camera.

Um, but what we do is add our PR expert and residents who used to be a reporter. And I do a really brief, like one hour media training session with every founder who hasn't had any media training so that they feel prepared to answer whatever is going to be thrown at them. And at the point that we do that, we've already prepared that document that I told you about, and the founder has already, I always say like, sleep with this under your pillow, like literally printed out and you will learn It through osmosis, but really internalize what's in that document and made it their own.

Then we do the practice interview. Ideally we already know the reporter that we're targeting. It's usually an exclusive at the seed stage. And then, um, ed can actually, he knows most of these reporters, so he can actually. Kind of come at it as the hardest version of that reporter so that the founder knows the types of questions they might ask and sort of their style and is really prepared for like a harder version of what they will get in real life.

And they lean on that FAQ that we prep, you know, we ask them to prep for questions like, you know, how much did you raise and at what valuation and from whom, and we're prepared to answer, is this founder answering their evaluation question? Or how do they not answer the question, but answer the rest of the question and do it in a way that isn't offensive to the reporter.

Brett Berson: It feels like one of the big shifts that's happened in called the last five or seven years that you've been, uh, both working on marketing and kind of this intersection with launch and PR is that, uh, the press has changed pretty dramatically. Um, both in the sense that, you know, in 2009 or 10, you raise $3 million.

And there's a number of people that were interested in writing about that. Um, and also as, as a business grows over time, there are more, there were more outlets which had been consolidated and there were more outlets that were interested in telling an optimistic story about technology. And it feels like the, the few remaining publication spend a lot of their time attempting to do either hard hitting or more investigative journalism versus profile pieces.

Um, and so I'm curious, you sort of mentioned this a little bit, given the change in the lack of interest in X interesting new company launches with $3 million, uh, what are the other tactics or, or advice that you give to founders. Is is just the role of the press less important or in some ways, do you think it's more important?

Arielle Jackson: So I'll start by just giving an example to acknowledge how different it is today than it was eight years ago. The last startup that I worked on, we could for our seed round that I don't remember the exact number, but it, you know, a three, $4 million seed round, we could go to five outlets, embargo the news, which means tell all of these reporters, all our whole story, have the briefing and agree to it.

Embargo lift date, which was like, you know, you pick a Tuesday morning at 7:00 AM Eastern, at which point they all file their story and you publish your blog post and all the news hits at the same time. And you get broader reach because you know, all these outlets are covering you and we could do that.

And that was quite plausible. And you know, at least three of those five would file this story today when we have the same type of, interesting. Seed stage startup doing something cool with a good message and a good lead investor, raising a normal seed round. We almost always have to run it as an exclusive, and there are only a few tech and business outlets that are interested in covering companies of that size and face.

Now, I still think that it's important for a lot of companies to do that, but it depends on your goals as to how important it is. So I've worked with some companies, for example, where getting that let's say tech crunch, venture beat, or, um, business insider, fortune Forbes sometimes are in that mix too.

Getting that article out is not really going to move the needle for them as far as usage or like top of funnel awareness goes, what that article will do for them is oftentimes attract partner interest, attract investor interest, potentially hiring It's sometimes a, a reasonable goal to have an article out there as a legitimize or, or to have a legitimising link that you can link to in your outbound sales you may have read about us in, you know, insert reputable new site here, as far as usage goes like directly converting people who read about you in one of those news sites into your users.

I think that is where. Like people have pretty unrealistic expectations and it doesn't always move the needle in a way that is meaningful. 

So to answer your question about what else can people be doing? I always think that that one article like, cause it's going to be one it's an exclusive these days, that one article is your starting line. That's not your finish line. That's not like, yay. We launched go celebrate. That's okay. We're out.

There are stories out there. What else are we going to do? And I have this conversation a lot with founders when we're gearing up, we do all that prep for this interview. But at the same time we start talking about, of course we start with what are your goals? And your goals are usually around either awareness, legitimacy, partnership, or hiring there's.

Sometimes investor interest is, is a fifth, but usually you have like one or two primary goals. And if your goals are what you just said, they were, what else are you doing? And especially when your goals are awareness and usage, getting like one article in one outlet, isn't going to be enough. So a lot of the time we talk about, well, what else are you doing on the marketing front?

a good example is like, You know, a FinTech company that has a consumer product, are you going to all the subreddits and posting and, you know, really participating there and doing more of the like grassroots style awareness building? Are you going on the podcasts and being a guest, are you advertising, do you have a paid marketing budget?

Arielle Jackson: Are you doing, you know, referrals with your current customers? Just like what, what is your marketing plan beyond your one article that announces your funding? Uh, and so I still think it's important. It's a good milestone internally for the team. It's a good thing to have as a legitimate user, but it's your starting line, not your finish line.

Brett Berson: And on your point about, you know, getting that first article and answer the importance in the, these times of doing an exclusive versus trying to get multiple outlets. Can you talk in a little bit more detail of a founders trying to do sort of a more DIY style announcement, kind of a little playbook that they should consider.

Arielle Jackson: Yeah. So one of the things that you touched on a little while ago was this idea of the press isn't out there writing glorious articles about technology companies anymore. And that's definitely true. I remember, um, you know, working on Gmail in like 2007, 2008, and we would literally the headline from like a reputable reporter who was lovely.

Uh, worried about GMLs like the, the title. I think it was wired. It said the best email you could ever have. And like, it was just an expo day about like how awesome Gmail is. And you don't really see articles with like those kinds of flattering headlines as much anymore. I think, um, my friend, Aaron , who was the VP of comms at square, um, he wrote this really good article, um, many years ago.

And it was about this clock model of news cycles and how everyone starts off as like the darling new kid on the block who the press is willing to write glorious articles about. And that's when the clock starts and then you go through, like, the clock is turning on you.

And eventually like you're going through this trough of despair where you're just getting like beaten down by the press. And then you go through like this enlightenment phase and he articulates it way better than that. But check that, that article, um, for sort of what happens to companies in a news cycle, if you think of all of tech and the arc of the clock that we're on in tech, you know, tech was for many years kind of in that glory phase of the new kid on the block.

And now we're a little bit more in like the trough of despair phase where. You know, people start feeling about tech a little bit, how they feel about banking many years ago, you know, like, oh, it's those tech guys like, oh, it's those bankers, you know, like you didn't hear that 10, 15 years ago. So you're, you're fighting against that. There are still outlets and reporters and, and ed knows them better than I do, who do want to write about cool, interesting technology that's having meaningful impact on the world or has the potential to, and the people who are writing those take-down pieces.

Usually aren't writing them about tiny startups that are just getting started. they want to write them about like the Fang companies or, you know, the, we work stories of the world and, um, the companies that have kind of, you know, flown too close to the sun. 

 how do you sort of craft a narrative specifically for this launch that is interesting or different, and that is probably something that may be slightly different than your ideal headline that maybe you would have five or 10 years ago.

Brett Berson: I think you kind of have to get an angle that ultimately you get a reporter to care about.

 I sort of agree with that and I sort of don't What you have to do is you actually have to have a company and product that people care about and if you do, and you describe it clearly, then the reporter who covers that space will be interested in talking about to you and about you.

Arielle Jackson: So I'll give you an example, um, you know, recently worked with, uh, a product in the design tool space, like people who cover design tools are interested in a very new take on design tools. People who cover education are interested in a very interesting new take on the future of education and accreditation, but you can't expect that you're going to go to like some random person who just generally covers tech at the New York times.

And they're going to care about what your specific product is about. So I think it's not necessarily having like that sexy news hook or tying it into some like what's happening current event or being cute and clever about.

it. It's actually about what is the problem that your company is solving And who are you solving it for?

And just being really, really clear. And if you have a great purpose beyond that, which is, you know, when you're super successful in 10 years, how will the world be different and believing it and telling a convincing story. That really just says that it's those back to those same fundamentals. 

Brett Berson: And then can you talk a little bit more about kind of the end-to-end process that a DIY founder.

Arielle Jackson: Sure. Um, so there's sort of three ways that we see seed stage companies getting that initial coverage. One way is you have a previous relationship with a reporter in your space, or you build one. if you're an ad tech founder.

I hope you're reading what Natasha at tech crunch is writing because she writes most, if not all of the ed tech stories on tech crunch.

And so you should already be reading and talking to her. And ideally if you're active in ed tech, you're also, you know, talking to her over DMS on Twitter, when you could be a source for a separate story that she's writing, you can introduce yourself to her and tell her a little bit about your company when the time is right.

So it's building a relationship or having a relationship yourself already with a relevant reporter in your space. Now not all founders want to do that or can do that. And so at first round, we run kind of what we consider like the DIY approach, which just means you didn't hire a PR firm. So we add an, I will help.

I found her do exactly what we just talked about, which is articulating all those, you know, why, who, what we'll get that all written down really crisp and clear. We'll train the founder, make sure they're prepped for all those hard questions. And then ed, he does run a PR firm outside of his work with first round.

He will pitch the right reporter on your behalf and set up the introduction. And then it's new. Take it from there to do the interview If you don't have somebody with that PR experience that you can rely on, a lot of founders will rely on their investors to make a warm introduction to the right reporter.

But that request to your investor is so much better. When you can say, Hey, I'm an ed tech founder. And we noticed Porter, X is covering our space and we think it's relevant. And here's what we're going to want to talk to them about. And here's a note you can forward to them as opposed to like, Hey, we'd love a warm introduction to a reporter, which is a lot of the time, frankly, what people provide.

So once you have the introduction and you do the interview. if you've prepared that document, the interviews, not that hard, it's like, you've already internalized all this messaging about who you are and why and how and whatnot you have it all down. And so now you're just have a chance to tell that story and you know, what the ideal headline is that you're going for.

And so in your brain, you're shooting to land that headline. There are many fewer reporters. And as you said, many fewer outlets covering seed stage stuff. And actually Alex Wilham at tech crunch wrote a really good piece about the consolidation of these newsrooms and the proliferation of seed stage investing.

So there's fewer reporters out there who are tasked with covering, way more seed stage investing than has been happening in the past. And so it's just, it's really like a supply and demand problem. 

Brett Berson: you touched on this a little bit, but how do you advise founders navigate the actual conversation? And I think sort of one thing I've noticed is that, um, if you haven't done a lot of media training, you tend to over-rotate on trying to directly answer the question of the reporter versus continuing to go back to, what am I trying to achieve in this conversation?

And so I'm curious, is there any other guidance that you would give a founder who's sitting down with a reporter tomorrow in terms of how to physically manage that conversation?

Arielle Jackson: Yeah, will, if it's tomorrow, I hope they already have a great document that prepares them. But if they didn't, I would say write down. what's the background point. So what's the, what's the world that you are playing in and the problem that exists in the world today. So state your problem statement.

That's the first one. So you have a background point, then you get a key message. If you can only say one thing, what is that key message? What Are you trying to do? It usually is something very closely tied to your category and benefit. Then you get some supporting messages. So you have somewhere between three and five supporting messages that support that key message.

So if nothing else there you just have your narrative. It's a background point, a key message, and three to five points that support it. And everyone should go into any interview with that. the next step, like how do you bridge back to your talking points and all of that? So I think what you're touching on is this idea.

I think you always should answer the reporter's question. 

I don't think dodging questions is a very good practice. I think answering the question and then bridging back to what it is that where you want to take. The conversation is actually a better way to approach that. we had one, one, um, founder recently, he was a first time tech founder. He had started other businesses in the past, like very successful businesses, but they weren't like tech type businesses.

And he had been trained by a media trainer for a previous role in which he was a spokesperson. And that media trainer had told him just answer, like, if the question is, you know, how many users do you have just answer with like, hundreds. And if they ask you a yes or no question, just say yes or no, like don't, don't go on because they're going to try to stump you.

They're gonna try to, it's got you just answer the question. I don't think that's right either. Um, they should feel like a conversation. So just in the way, I mean, I've been doing 95% of talking on this podcast, but just in the way where like Brett, you ask a question, kind of makes me think of something.

 I have some things I want to cover. Like there's ideas that I want. I like talking about that. I want to make sure to express, but there's also some naturalness to it where it's like, oh, that reminds me of this thing. And I want to talk about this. So as long as you know, like these are the three points I must cover, these are the 10 things where I might get slipped up.

Arielle Jackson: You can bridge back to the three points you want to cover. And you're prepared for those things where you might get slipped up, but you don't need to just be like a robot. Who's like, yes, you want to say yes. And then you go to your key messages and you explain why like yes. And, uh, and really be able to flesh out answers reporters, at least most of the ones that, that we work with a little bit, uh, behind the scenes.

They're not trying to get you. They're trying to see where is the interesting story here? Where's the cool innovation that you have that we want to write about.

Brett Berson: Are there specific areas sort of tricky questions that you see come up more frequently and maybe is there any perspective you have? So one that jumps to mind for me as getting you to talk about competitors, particularly in a negative way. Um, and I don't know if you have thoughts on that or, or a few other things that come up over and over again, and how to manage that.

Arielle Jackson: Yeah. So we had talked about in your positioning, you want to identify. Your foil, right? What is the competing alternative that your target customer is doing today? If I'm a reporter and I cover, you know, FinTech, I'm going to know about all the startups that came before you that tried to do something similar to what you're doing or are adjacent to you. But if really what you're up against is like paper checks or some old way of doing things.

When you get asked about a competitor, you know, it's not really about that competitor. It's about the old way of doing things. So as much as possible, you want to reframe the conversation around a competitor. If this is true, that you're actually up against the old way of doing things to be like, yes, so-and-so competitor X and us are both trying to solve the problem of paper checks or however, your old way of doing things is here's how we're different.

And you don't really want to talk about them. You want to talk about how you're great and how you're different and what makes you unique and how you're going to be better than the old way of doing things. You don't need to put words into their mouth, or really give them a lot of airtime. You shouldn't be talking about your competitors in these interviews, you should be talking about how you're different and how you're better.

Brett Berson: So maybe to wrap up, you hinted at a couple of these things, but what are your favorite books or resources on all the different topics that we've covered, sort of, where have you found a lot of, uh, inspiration or maybe you think of a typical first round founder? Who's kind of doing all this for the first time.

What, what are sort of the resources or places you'd point.

 so I mentioned that really old school, one it's called positioning the battle for your mind. It's a quick read. It's almost like a booklet, it's like 140 pages or something like that. that's a great read. I highly recommend that.

Arielle Jackson: Um, there's a few other books that also are like, adjacently about positioning. Like that book that's played bigger, where they repositioned positioning as category creation. I think that's a good read. I don't agree with everything in there, but I think it's a fun read. I'm reading a book right now that I'm kind of obsessed with.

 It's called alchemy, the dark art and curious science of creating magic and brands, business, and life. Uh, it sits at the intersection of marketing psychology, behavioral economics, and evolutionary biology. And that's like, that's my jam. Uh, I, I studied human biology in college.

Arielle Jackson: I got a master's in psychology. I a marketer. It's like all of my favorite things in. another great book, actually, I'm Dan Arielli Ellie's book. I'm blanking on the name right now. Um, 

Brett Berson: irrational.

Arielle Jackson: yes, that's another great read. I highly recommend that one. Um, but these are, these are kind of like, they're not going to help you position your company.

They're going to get you thinking in a new way about how people make decisions. Um, I think if you really want like a guide on how to do some of this work, probably that book positioning is the closest. And then, um, we wrote some articles on the first round review that give kind of the tactics of what I run P founders through, uh, just really basic frameworks and exercises that you can follow along there.

There's two articles that I'm thinking of on the first round review, at least. 

Brett Berson: Awesome. And we will put those in the show notes. Well, thank you so much for spending this time. This was awesome. Thanks, Ariel. 

Arielle Jackson: Yeah. Thanks, Brett.