Aug. 18, 2022

The art of building legendary brands | Arielle Jackson (Google, Square, Marketer in Residence at First Round Capital)

What makes a great brand? After working at Google and Square, Arielle Jackson has spent the past eight years consulting startups on how to create powerful messaging that works. In this jam-packed episode, she shares how to pick a winning name for your company, create a brand purpose that excites your team and customers, and position your company and its products for success. You don’t want to miss this one!

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Thank you to our wonderful sponsors for making this episode possible:

• Flatfile:

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• Positioning Your Startup Is Vital—Here’s How to Nail It:

• Three Moves Every Startup Founder Must Make to Build a Brand That Matters:

• What I Learned from Developing Branding for Airbnb, Dropbox, and Thumbtack:

Positioning: The Battle for Your Mind:

Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life:

The Vanishing Half:

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How I Built This:

In Depth:

Unseen Unknown:



Old Enough!:

• The Sociology of Business with Ana Andjelic:

• David Ogilvy:

• Rory Sutherland:

• Seth Godin:

In this episode, we cover:

[04:04] From making jewelry as a side hustle to launching products for Square: Arielle’s background

[12:32] What makes a good name for a product or a startup

[19:17] How to come up with a great name

[24:59] How to run a naming brainstorm for the best results

[31:09] Bad names and naming mistakes

[34:17] Arielle’s brand development framework and when founders should implement it

[36:02] How do you know when brand development is completed?

[41:17] How long should branding take?

[42:42] How to build a brand purpose that ignites excitement

[48:51] Specific tactics for building your brand purpose

[51:12] How to master your positioning

[55:22] Why it’s important to stay niche when you’re mastering your positioning

[59:15] The process of positioning and Arielle’s bar test

[1:02:38] How to build a brand personality using the five big brand descriptions

[1:07:39] Where to put brand and product positioning documents so they’ll actually get used

[1:09:14] How startups can get PR

[1:14:49] When should you hire a marketer?

Production and marketing:

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Arielle Jackson (00:00:00):

So over time, a word can come to mean something that is beyond what that actual word means. Like Disney means magic today. Volvo means safety. Those names are not good. If I just put it in a spreadsheet or one of those lists, no one would pick it. So that's kind of what I mean, that the name is just part of the overall marketing or the overall brand and a bad name with a really great company with great company strategy, great marketing is going to be great over time. And a good name is just going to help you, but I don't think a bad name is going to kill a good company.

Lenny (00:00:42):

Arielle Jackson spent nine years at Google, where she helped grow Gmail in its early days, taking it from just a side project to a product that is now used by hundreds of millions of people all over the world. Then she went on to Square, where she was one of the first marketers and helped launch and scale the growth of Square reader. She's also worked with over 100 early stage companies, helping them nail their brand and marketing efforts, including Patreon, Loom, Front, Eero, Maven, Sprig, just to name a few.

Lenny (00:01:12):

These days, she teaches a super popular course on startup brand strategy and she's a marketer in residence at First Round capital. In our chat, we cover primarily three things, naming strategies for your startup or your product, a framework for developing your brand, that includes your purpose, your positioning, and your personality, and also getting PR for your startup. I can't wait for you to listen to this conversation with Arielle. And so with that, I bring you Arielle Jackson.

Lenny (00:01:41):

Hey, Ashley, head of marketing at Flatfile, how many B2B SaaS companies would you estimate need to import CSV files from their customers?

Ashley (00:01:49):

At least 40%.

Lenny (00:01:51):

And how many of them screw that up? And what happens when they do?

Ashley (00:01:54):

Well? Based on our data, about a third of people will consider switching to another company after just one bad experience during onboarding. So if your CSV importer doesn't work right, which is super common, considering customer files are chock-full of unexpected data and formatting, they'll leave.

Lenny (00:02:13):

I am 0% surprised to hear that. I'm consistently seeing that improving onboarding is one of the highest leverage opportunities for both signup conversion and increasing long-term retention. Getting people to your aha moment more quickly and reliably is so incredibly important.

Ashley (00:02:28):

Totally. It's incredible to see how our customers like Square, Spotify and Zuora are able to grow their businesses on top of Flatfile. It's because [inaudible 00:02:38] data onboarding acts like a catalyst to get them and their customers where they need to go faster.

Lenny (00:02:45):

If you'd like to learn more or get started, check out Flatfile at

Lenny (00:02:53):

This episode is brought to you by unit. What did Gusto, Uber, Shopify and AngelList all have in common? They've all decided to build banking into their product. According to AngelList head of product, banking makes every single feature more interesting. With it, our platform functions as financial mission control for our customers. Without it, we're just another software tool in a big messy stack.

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Lenny (00:03:41):

To hear more about how Unit enables companies like yours to build banking, visit lenny to request a demo or to try their free sandbox. That's

Lenny (00:03:58):

Welcome to the podcast, Arielle.

Arielle Jackson (00:04:01):

Thanks so much for having me. It's great to be here.

Lenny (00:04:03):

It's absolutely my pleasure. I've read so much of your writing online. You've done a lot of writing, which I found really helpful. And so I'm really jazzed to be digging into all kinds of really good stuff. Before we get into some of the meat, just a couple questions that I had in my mind. You've worked with so many amazing companies, Google, Square, Loom, Patreon, Front. So many others. I don't want to keep going. What's been either your favorite or most unusual project that you've worked on?

Arielle Jackson (00:04:35):

Gosh, it's like asking me to choose my favorite son. I'm like, gosh, I can't really like pick one.

Lenny (00:04:40):

That'll be the next question.

Arielle Jackson (00:04:41):

I would probably say that my favorite project, and this is because they get reminded of it on a daily basis was working at on the Square stand at Square. It was the first time I ever worked on hardware and our joint Square was 140 people. We had no marketing function. We had a couple marketing people. We had no product managers and the hardware team was running the show on launching this new product that was supposed to get us up market into brick and mortar.

Arielle Jackson (00:05:05):

And anyway, I was running event marketing at the time and giving away a bunch of those readers that you stick into a phone for free and having a lot of small merchants use. I volunteered to run the launch of this product as a product marketer for the first time. And it was just so fun, doing everything from positioning it, figuring out how we were going to talk about this beautiful new piece of hardware that would turn your iPad into a real point of sale.

Arielle Jackson (00:05:31):

We had people fly around the country and get cool coffee shops and brick and mortar businesses seeding it so that they would all use it. We had I think 15 Metro areas covered with the coolest coffee shops and donut shops and everything at launch. And you know, there was a lot of fake it till you make it. I was negotiating a deal with Best Buy in the Apple store. Never done anything like that before.

Arielle Jackson (00:05:53):

Designing packaging was really awesome. There was just so much to it launching a physical product. And at the time it was at a pretty high price point for a company that had always had one free product and helping that company go up market. And I remember I was 30 something weeks pregnant when we launched. We got all the blue bottle stores to use it. And we had this launch event where Jack, our head of hardware, Jesse unveiled this product at the blue bottle in Mint Plaza. And I was super pregnant and super proud. And I still get kind of excited every time I pay on one of those, which is all the time.

Lenny (00:06:30):

Super pregnant and super proud. I love it. And that product that was the POS stand, the iPad thing that you kind of swivel and sign.

Arielle Jackson (00:06:39):

Yeah. And there's been new versions of it since, there's a contactless version of it, and there's one with an integrated screen that I think is Android based, which you don't have to have an iPad, but that product's still around. I still pay on that original Square stand all the time. I drink a lot of coffee. Those independent coffee shops around LA. So they're all still using it.

Lenny (00:07:01):

We're going to talk about positioning a bunch, but while we're on the topic, what was the positioning of that product while we're talking about it?

Arielle Jackson (00:07:07):

Yeah, so at the time Square was mostly used by farmer's market vendors and event vendors. I made jewelry in a past life and that's how I got to Square was being one of those vendors. And the positioning was really that it was for brick and mortar businesses, particularly quick serve coffee, donuts, sandwich shops that kind of quick serve brick and mortars. And it was up against your ugly old point of sale. Your cash register effectively. That was our foil. And the benefit was turn your iPad into a point of sale. And the differentiator was about one unified experience that you can do everything you can on your cash register and more, and you'd be proud to have it out on your counter.

Lenny (00:08:01):

So you said that you were creating jewelry and that's how you got into Square to work on this product. I need to hear more about that.

Arielle Jackson (00:08:08):

Yeah, sure. So I was working at Google before Square and I'd always had this hobby of making jewelry and I used to sell my jewelry in a few different like boutiques around San Francisco and LA. It was a very small side hustle, but it was my creative outlet. And I sold at craft fairs around Hanukah/Christmas time. So I used to sell and just take cash. And then I got a Square reader and I sold at a craft fair that year. And it was awesome. That Square reader, it helped people buy more, it helped me sort of look cool. It was just really great to accept credit cards. I'd never done it before.

Arielle Jackson (00:08:49):

I used to take PayPal invoices and be on my computer and send someone an invoice and they'd get it. It was painful. All the reasons that people use Square, I experienced it. And two people I knew from Google, Megan Quinn and Kyle Dink had gone to Square from Google. And so after I had that experience, I think I sent them both an email just being like, this thing's fucking awesome. I make jewelry. It was great. I sold I think it was 50% more than I did last year because I accepted credit cards and I can't remember which of them wrote back first, but they were like, come interview. And so that was basically how I ended up at Square.

Lenny (00:09:27):

Wow. I bet that helped you a lot through the interview, actual have personal experience.

Arielle Jackson (00:09:32):

Having been a merchant, I think it helped me understand the small merchant that initially we were marketing to.

Lenny (00:09:38):

And so today you are marketing expert in residence at [inaudible 00:09:45] capital. I was going to ask what does that mean and what is it that you do day to day these days?

Arielle Jackson (00:09:51):

Sure. So after I left Square, I went to a tiny startup that was seven people. They were funded by First Round and I helped them with everything that a tiny startup that's trying to grow needs.

Lenny (00:10:06):

What startup was that?

Arielle Jackson (00:10:06):

It was called Cover. They were acquired by Twitter. It was an Android app that could get you the right apps at the right time based on where you were by changing the lock screen on your phone. And so that company and that experience of working at this tiny startup that was seven people, I really liked it. And then they got acquired by Twitter, but I had just left Square. So I decided not to join Twitter with the rest of the team. And instead I just decided I was going to help a bunch of other small startups. And I emailed a few friends from past lives who had small startups, which was like, Hey, I'm not going to Twitter with the rest of the team. You do need marketing help. And every single person wrote back and said, yes. And that's basically how I started consulting.

Arielle Jackson (00:10:49):

I guess it was about eight or nine years ago. At the same time, First Round had reached out and said, hey, who did you use for marketing comps for cover? And I got connected with Brett from First Round and he's like, would you help our companies? And we did a three month project for one day a week, nine years ago. And I'm still there. I work halftime at First Round. So I do everything I do for other companies, but for First Round companies on First Rounds time.

Arielle Jackson (00:11:17):

So the way it works is if you're funded by First Round and as part of your onboarding, we offer a lot of value add services and I'm one of them. And those services can be everything from, we have someone who's really good at compensation and HR stuff and we have someone who will help you with pricing and I'll help you with marketing. And what that means when you're a seed stage startup is everything from naming to positioning, to developing a brand identity, a website and your initial launch, and eventually hiring a marketer. So that's sort of the bread and butter. That's what I like working on anyway. So it's a good fit because we invest in a lot of seed stage companies at First Round, I get to help almost all of them.

Lenny (00:11:58):

That's an excellent segue to what I wanted to get to next. What I want to do in our chat is cover three broad topics. Things that I know are very near and dear to your heart, naming for products and startups, your brand development framework and how to hire marketers. Does that sound good?

Arielle Jackson (00:12:15):

Awesome. That's what I like to talk about. So yeah, let's do it.

Lenny (00:12:19):

Let's do it. Surprise, surprise. Okay. So with naming, I've actually heard from a few founders that you were really helpful to them in naming their startups. Folks that have maybe been on this podcast that will go unnamed. So for founders trying to come up with a name for their company or their product, two questions. What makes a good name for a product or a startup, and then just how do you come up with a great name?

Arielle Jackson (00:12:44):

I love naming. I think I've named just over 30 companies at this point. And actually when I mention how I got into consulting when I emailed some friends and asked them if they needed marketing help, I think I'm allowed to talk about this one. So one of those companies was some friends from Google, Adrian and Carl. They had left Google, gone to Facebook and then started a company it's now called Seesaw. It's an ed tech company. That was the first company I named post Google Square, all of that.

Lenny (00:13:09):

It's an awesome name.

Arielle Jackson (00:13:10):

It is an awesome name and I'll use it as an example. So seesaw is a ed tech company. They had a really bad name before that and we did this whole naming process and ended with that name and why I think that's a good name is when I say Seesaw, you don't really know what it is, but when I tell you, oh, it's this ed tech company and it's an iPad app and it helps the work that elementary school students do go between the teacher, the parents and the student. And you're like, oh, well, Seesaw makes sense for elementary school, it's something that goes back and forth. It has that sort of nostalgic feel. And it makes sense that it's an ed tech company.

Arielle Jackson (00:13:49):

And I personally tend to like those kinds of names that are suggestive or evocative, where when I tell you what the company does, you're like, oh, that makes sense. But it's not that what the name is tells you exactly what the company does. So that's an example, I think of a good name. I don't know, during COVID and when my older son's school was closed and they all used Seesaw and I got to tell my son, oh, that's my friend's company and we named it back in the day. And he was like, oh, that's cool. That name makes sense.

Arielle Jackson (00:14:21):

That's the reaction you want. It also has a little bit of emotion to it. It has some nostalgia. It's fun to say it's short, it's memorable. I think all of those things make a good name. Another company that has a good name that you and I have both worked with is Maven. So they're a First Round company. Gogan has talked about this publicly. We named that company together. Maven is a Yiddish word that means one who understands and it means specifically one who understands because they've done something, they've acquired the skills or knowledge over time.

Arielle Jackson (00:14:58):

And I just think that's such a cool name for a platform that allows X operators or current operators to teach their skills to other people through cohort based classes. You want to be a Maven, instructors are Maven's, it's short, it's easy to say, when I tell you what that company does, that name makes perfect sense. So I tend to like those [inaudible 00:15:17] of names myself, but I also, I don't know, I like other kinds of names for other kinds of products too. I think it really comes down to what is your product? What is your company? What is the name trying to achieve and really getting clearer with those criteria. So we can talk about the criteria that always apply, the criteria you might add and a process to get there.

Lenny (00:15:38):

That sounds great. Yeah. I'm really curious about a process. If one exists, that'd be really cool. So another question in my mind is just some names are just nonsense words like Yahoo and I don't know Google, I guess. What's your take on that as a name, that approach?

Arielle Jackson (00:15:51):

Yeah. So words like that are empty vessels, they really don't mean anything. If you think about the name Yahoo, it's actually like really silly. It's like Yahoo. I always hear it like that. Google has a meaning for people in the know with the one followed by as many zeros. It's like a big number and it's a misspelling of that. So that one's a little less silly to me than Yahoo. My take on empty vessel names is they can be really memorable and they can be evocative of the emotion, but you have to do a lot more marketing work over time to make it mean something.

Arielle Jackson (00:16:25):

So if I say Yahoo today, we know it's that search engine we use before we all switch to Google and we have the purple color in our head, and we think about what it meant at the time that we might have used it, but it took a lot of marketing dollars and a lot of time for that word to be in that. So they're doable. I worked on a company Eero. That has kind of what is almost an empty vessel name. Eero is for Eero Saarinen who was a designer. He did like these really beautiful buildings, architectural buildings. And then also some tables. You can get a Saarinen and table at Design Within Reach, but that name, nobody knows that unless you're in the design community. And so that name is effectively an empty vessel and they have to spend a lot and be consistent about making that [inaudible 00:17:16] mean a wifi system.

Lenny (00:17:17):

I want to get to the process, but another question is why is it important for the name to kind of connect to the company and what they do? Is that just it feels nice to people or is there some kind of a bigger reason?

Arielle Jackson (00:17:30):

Yeah. So it doesn't have to, and examples like Eero and Yahoo, it doesn't. Even if you think about Apple, it doesn't. Apple has nothing to do with Apple computers. It's a word we all know. There's a lot of words where there's no meaning behind it. If there is a meaning behind your name, your name is doing a little bit more of your marketing work for you. So if your name is Internet Explorer, RIP, I know exactly what you do.

Arielle Jackson (00:17:56):

If your name is Chrome and you're a designer on the web, you kind of might be like, oh, that makes sense. That's the area around the browsing window. If your name is Firefox, I have no idea what you did. You just took two words and put them together and made something up. And now you have to spend, and you have to be consistent over time in making that word mean something for people. But all three of those browsers were successful at a time. And I don't think the name had anything to do with Internet Explorer's demise.

Lenny (00:18:25):

Got it. So it's kind of ideally you can find an easy mode. If that doesn't work, then you go hard mode. You come up with your empty vessel name and then you just have to do a lot of work.

Arielle Jackson (00:18:33):

That's my personal preference.

Lenny (00:18:35):

Okay, cool. That makes sense.

Arielle Jackson (00:18:37):

My personal preference is if you think about there's descriptive names, the Internet Explorer, there's suggestive names like Chrome, then there's evocative names, which I would say Seesaw and Maven fit into there where they're like in between suggestive and evocative, and then there's empty vessel names or fanciful names. There's a spectrum. And when you do your brainstorm, we can talk about this in the process, you want to think across all of them, but you might have in your naming brief, we want a suggestive name, or we want a descriptive name. You might go into it with that. And so there's times and places for all of those names across the spectrum. My personal bias is I tend to like suggestive names.

Lenny (00:19:16):

Makes sense. Okay, let's get into it. What should teams do when they're trying to name something?

Arielle Jackson (00:19:22):

Yeah. So the first thing is to do your product positioning. I really believe that positioning dictates so much of your marketing and should always be the first thing you do. I had a student in my last class that I taught through Maven. I teach a class on brand strategy and he was I think a second or third time founder, who had never taken a class on brand strategy. He worked really hard. He was awesome. Anyway, at the end of the class and you kind of do this closing thing. And he goes, I'll never write a line of code without doing positioning first. And that was music to my ears. I think positioning comes first, but in any case, you do that first, and we'll talk about that in a little bit. And then you write a naming brief and it's really simple.

Arielle Jackson (00:20:07):

What are you naming? Are you naming a company? Are you naming the product? Are you naming both? Usually if you're early stage company, you're naming both and they're going to have one name because you don't want people to have to remember two things. What do you want the name to communicate? So in that example of Seesaw, we wanted it to communicate young childhood. In the example of Eero, we wanted it to communicate design, being designed forward. It can be whatever you want it to communicate. What do you want to avoid? We don't want it to sound like this competitor, or we hate this word or whatever you want to avoid. What are the names of competitive and related products? And then are there other considerations? I worked with another First Round company that was operating in China.

Arielle Jackson (00:20:53):

And one of the considerations was this has to be pronounceable for a native Chinese speaker. That's a very valid, additional consideration. And then there are seven criteria for names that always apply in my opinion. And you could add additional ones, like that Chinese speaking one would be an additional one. The seven are trademark, which is kind of obvious, can you use this? Are you violating someone else's trademark? And the second step with trademark is, do you need to proactively protect the name? Domain availability, so everyone gets hung up on getting like got It was an arduous process that Gogan wrote about on Twitter. But these days, you don't necessarily need Square operated on SquareUp for very, very long time. Lots of companies are operating on variants of a .com. So domain availability, distinctiveness. Is it memorable?

Arielle Jackson (00:21:51):

Is it sound like someone else's name? That's I think one of the most important ones, just is it different and distinctive? Is it timeless? So there's a lot of naming trends. If you tell me Optimizely I could tell you what year was the company formed when it ends in LY. If you tell me a word like Flicker, I can tell you what year it was, because that was the naming trend to remove vowels. So I generally stay away from naming trends, because I want your company named not to sound dated in 10 or 20 years. The last one is it's kind of related to that. What we talked about in the brief, what do you want the name to communicate? Which is the name reflective of your key messaging or does it somehow suggest an emotion or feeling that you're trying to convey, and then sound and ease of pronunciation.

Arielle Jackson (00:22:44):

Is it fun to say, is it easy to say, how is it to spell? We almost named a First Round company a while ago Lattice which is now a different company that's doing quite well, but we didn't name it that because this was a company that was B2B sales was going to be their main channel. So they're going to be people on the phone being like, hey, I'm calling from Lattice and we went through this exercise and we're like lettuce? It's not so easy to say and spell. So we actually didn't name the company that and went with something else. But there's a company now doing quite well.

Lenny (00:23:16):

You think that was the right move?

Arielle Jackson (00:23:18):

I don't know. I always say a good name is only going to help you, but a bad name won't hurt a good company. So I don't really feel-

Lenny (00:23:25):

Interesting. Good to know. Yeah. Keep going.

Arielle Jackson (00:23:27):

And then the last two are appearance. So there are some names that just lend themselves really nicely to visual design and they have to do with how tall the letters are and is their symmetry and if you give this to designer, making a logo just so awesome and cool and fun and then length. So a lot of people, they want to name like Square and Stripe and these one syllable names, but a two syllable or even a three syllable name can often be more memorable.

Lenny (00:23:57): Shoot.

Arielle Jackson (00:24:00):

Yeah. Well, so you got the Lenny part with the two syllables is generally a nice sweet spot.

Lenny (00:24:07):

Sweet. Have you put out a template or anything that folks can find to do this? Or should they kind of listen here and take notes?

Arielle Jackson (00:24:15):

Yeah, there's an article on the First Round review called Positioning Your Startup is Vital, Here's How to Nail It and all those criteria and how to do naming is actually in that article.

Lenny (00:24:27):

Awesome. We'll put that in our little show notes. And then as you go through this, is this a binary thing or you kind of rate each of these categories one to five?

Arielle Jackson (00:24:36):

Yeah. So the way I do it is I apply the criteria after we do the brainstorm. And then we do red, yellow, green on each of those criteria just to weed out ones that are not doing well on any of those. Got it. And then you add your own criteria. So the next steps the brainstorm. I'm going to go fast through this.

Lenny (00:24:55):

Yeah. I was going to ask you about the brainstorm. I'm excited to hear this.

Arielle Jackson (00:24:57):

Yeah. So the way that I run a naming process is I like to first do positioning and then I set up an hour with the founders and me and ideally a couple other people who are interested, but disinterested. So I'll bring a writer from the First Round team or the founder has a friend who's a linguist or the founder has a friend who speaks four languages. We like those kind of people to be in it if possible. And it's generally five to seven people in a brainstorm. And the idea is we spend one hour, I set it up beforehand and we try to come up with hundreds and hundreds of bad ideas and a couple decent ones that are worth exploring more. And the brainstorm is two parts. The first part is based on words in your positioning statement.

Arielle Jackson (00:25:40):

So we take all the meaningful words out of your positioning statement is the warmup and we run synonyms, antonyms, free associations, other languages, whatever we can do off of those words. And so if your words in your positioning statement are related to what that you do, which they very well should be, that's a great way to just come up with hundreds of words really quickly. And then the second step is a thematic brainstorm. So I pick between seven and 10 themes, you can think of them like Jeopardy themes. So it's like, I don't know, okay, so there was an-

Lenny (00:26:11):


Arielle Jackson (00:26:11):

... AI. Yeah. It was like an AI tool for strawberry picking and the themes would be the history of strawberry farming or botany 101, things that are related. You could do like last names of famous farmers, think about how did Tesla get their name? They probably did last names of people related to electricity, and that's such a great name, so thematic brainstorm. And then that's usually a little more fruitful. And we do the same thing, free association, all that.

Arielle Jackson (00:26:40):

I spend some time afterwards on Wikipedia and the internet and actually finding words words. Also love the library, check out books sometimes and just read books on the topic and just write down the interesting words that come up. And anyway, so then I give them back a short list. The short list is around 10 to 25 concepts that are ideas that are worth looking at further. And from there narrow it down based on the criteria and the red, yellow, green, we come up with three to five, don't come up with one because you might not get it for trademark, and it's really sad when you get really attached to one and then you can't use it. So yeah, three to five top contenders. And then you go through trademark process domain and kind of go from there.

Lenny (00:27:23):

That was amazing. If you're doing a startup name versus a product, is the process any different or is it basically the same?

Arielle Jackson (00:27:29):

No, same. The only difference is if you have a lot of equity in your company name... Square is a good example. Square had a lot of equity. Google is a perfect example. A lot of equity in the company name, you often don't want to name your products something really creative and different because you actually want the equity in the master brand to come through. So if you think about Square's names, they have other ones, when they diverge from the Square brand like cash or when they want something new or Google, when they came out with Android and they wanted to diverge from the master brand. But think about all the products. Square Register, Square Stand, Square App, Google Maps, they're really boring and it's because the equity is in the company name and the product name can actually be boring and descriptive.

Lenny (00:28:20):

That makes sense. I want to come back to a point you made that a great name will help a startup and a bad name is not going to hurt you or I forget the word to use. I'd love to hear that because that's that's really interesting.

Arielle Jackson (00:28:33):

Yeah. So if your company has a great name and the name is remarkable, people will be like, oh, that's a great name, or it just makes sense. In the case of Seesaw like, that's a good name for that company. That good name is just going to help people talk about it. It's going to spread word of mouth. People are going to like to talk about the company. If you think about there's a lot of companies with bad names that we use all the time or even quite boring names that we now love. So if you think about Disney, Walt Disney's last name, it didn't mean anything, but over time that's such a good company and it got imbued with all this meaning and now it stands for magic and stands for so much, but it was just the dude's last name. So over time a word can come to mean something that is beyond what that actual word means.

Arielle Jackson (00:29:21):

Disney means magic today. Volvo means safety. Those names are not good. If I just put it in a spreadsheet or one of those lists, no one would pick it. So that's kind of what I mean that the name is just part of the overall marketing or the overall brand and a bad name with a really great company with great company strategy, great marketing is going to be great over time. And a good name is just going to help you, but I don't think a bad name is going to kill a good company.

Lenny (00:29:51):

So interesting. So basically your goal is to help find a name that will help. Worst case, you're going to be okay if your product is awesome.

Arielle Jackson (00:29:59):

I think so. Yeah. I mean it also takes a little of the pressure off to be honest. Everyone wants to find that perfect name. If you actually think about it, this happens a lot. You give someone a list of 10 names or 15 names and they're just cells in the spreadsheet these days, we're doing most of this virtually. You give people a name like that and it's like, you have to imagine what it could be. You think about Apple or Disney or Nike or Volvo, Lego, any of these brands, in a cell spreadsheet in plain Arial in 10 point, they're just okay, you have to grow them over time. You just hear about I think Phil Nate with Nike, when he was given that name as an option, he was like, that's okay. Yeah. I'll sleep on it. Such a great name.

Lenny (00:30:50):

This makes me think about my startup back in the day, it was called Local Mind, and we went through an exercise similar to this. Not nearly as in depth and well run, but I remember our designer was the person that helped us nail the name. He's just like, oh, I could do so much with this name. Let's just see where this one can go. Is that something you find?

Arielle Jackson (00:31:10):

Yeah. There's definitely been bad names. I helped a company rebrand recently that they had a bad name. It just looked dated. It didn't fit any of those. It wasn't distinctive. It wasn't timeless. It had one of those like naming trends. Those are not good. You want to avoid those, but if you come up with something that is pretty good and you can make up something beautiful out of it and it fits your company, it does some of the marketing work for you and people like to say it and ideally it's memorable and it has some emotion to it, go, go for it.

Lenny (00:31:39):

Awesome. One last question about naming. What's a common mistake that people make going through this process coming up with a name?

Arielle Jackson (00:31:47):

Yeah, a really funny one is if you have a code name for your product or at First Round, a lot of the companies we invest in, they raise their seed round with one name. They may or may not be attached to it, but then they work with me and I'm like, yeah, your name's not that good, and here's why, we should probably change it or they say, we can't use this name. We found out we have a trademark conflict. I really believe in using a code name that's so ridiculous that you won't ever launch a product like that if you're just trying to incorporate and go really quick.

Arielle Jackson (00:32:18):

So for example, a lot of people, they need their name for their corporation. And so they are filing all the steps to creating a business and they just like pick something, but then they end up getting attached to it and then they want to actually launch under that name. And it's like, well, that's not so great and here's why I think you should change it. If you pick something so ridiculous that you would never launch, it's actually helpful because then you can go through a process and find a name that will do more of your work for you and you won't be attached to something crappy.

Lenny (00:32:50):

Such a good point an idea. And by the way, so if you're a First Round company, you get this naming service for free and all these other things we're going to talk about just to be clear.

Arielle Jackson (00:32:59):

Yes, that's right.

Lenny (00:33:00):

Oh my God. I could do a whole episode about how much I love First Round, but I will say I'm a huge fan. I think I've participated in every program that First Round offers. The First Round review is actually one of the first pieces of writing that kind of helped spur my now career. And so I'm really-

Arielle Jackson (00:33:15):

I remember that article, was awesome.

Lenny (00:33:17):

Yeah. And I did two more after that. So much work, but yeah, that was a big deal. So I'm really appreciative to First Round. And we could talk about First Round a bit at the end, too.

Arielle Jackson (00:33:26):

Sure. Yeah. Everything we're talking about that you've asked me so far, I think that you're going to ask me about positioning and [inaudible 00:33:33] your marketing person, and all of that is stuff we offer to First Round company, we offer my services as part of the investment. There are times when we might get stuck and we have to bring in an outside person to help us with something, but for the most part, it's all included and you'd pay a lot of money... The naming firm I like the best when I get stuck, it's called A Hundred Monkeys. They're awesome. A long time ago, I used to be like, oh yeah, it's about $25,000. And I recently couldn't take on an outsider First Round project and referred it to them. It's $47,000 for a name.

Lenny (00:34:04):


Arielle Jackson (00:34:05):

So yeah, it's gotten expensive, but if you have the means, it's nice to get some outside help.

Lenny (00:34:12):

#valueadd. Okay. I want to transition to your brand development framework, which I read a bunch about. And I know you teach a course about this, which we could also chat a bit about, but first I'm curious, just practically, why is a brand useful? Why is it even something people should spend time investing in? Why does it matter?

Arielle Jackson (00:34:33):

Okay. So a lot of founders may think that when we say your brand, we mean your logo and your font and your colors, and that is a visual expression of your brand, but it's not actually your brand, your brand is who people think you are. And so why is it important for people to think what you want them to think? That really comes down to people's understanding and particularly your target audience's understanding of what your company and your product is. And I don't really think there's anything else more important than that if I was building a company.

Arielle Jackson (00:35:08):

So your brand is who people think you are and developing a brand strategy is what do you want to be? What do you want people to think you are? And what are you going to do to help shape that perception? So when I work on a company, there's a lot of steps to this, but I kind of have this nice little process that's right sized for early stage startups. And I like to start with, why do you do what you do? Just having a really clear understanding of that. That's your purpose. The second part is your product positioning. So meaning how do you want people to understand your product and what role it plays in their lives? And then the last part is your personality, which is how do you show up in the world? What do you like? If your brand was a person, would I want to hang out with them? Would someone else want to hang out with them?

Lenny (00:36:02):

We're going to get into each of these three pieces, but before we get in there, as a founder, how do you know when you're done with your brand development? I know it's a never ending ongoing process, but at the end of a process, you figure out your purpose, positioning, and personality, and then there's logo and colors, when you think about just here's the brand package, what are all the little pieces of it? And then we'll dive into these three elements.

Arielle Jackson (00:36:30):

I think what you said is right. You get those three components, your purpose, your positioning, your personality, you use that as an informant to your visual design and also to your tone of voice. So the way your copy sounds, the way you show up in written copy. A lot of companies have what they call like a style guide or a brand style guide and it really only covers logo, fonts, colors, like don't put our logo and blue, don't tilt it on an angle, here's what it looks like in white, here's what it looks like in black, here's the favicon, but they don't have that for here's who we are, here's 10 lines that could be ad copy for us, here is why we do what we do.

Arielle Jackson (00:37:14):

This is the personality of our brand. Here are five attributes. We are playful, but not silly. We can talk about that a little bit more. But I think all of that belongs in the style guide, not just logo, font colors, which is really just a visual articulation that feeds into your brand. I'm a big Volvo fan. I'm on my fourth Volvo right now. So I'm super brand loyal. And I always use them as an example, because if you can picture the Volvo logo in your head right now, it kind of looks like the male symbol, it's like a circle with an arrow coming off the side.

Arielle Jackson (00:37:48):

There's nothing about that logo that means all the things I like about Volvo, all the things that the Volvo brand has come to mean to me and they're colors, they're like black and white and a little blue. There's nothing more boring than their color palette. And so it's not the logo and the font and the colors of Volvo that has made them mean... They literally own the word safety in cars right now. It's other stuff. And if you looked at their style guide actually, looked at their style guide recently and it's just like, here's our black and our white and our blue and here's our tertiary colors and here's our logo. It would not help you understand Volvo as a brand.

Lenny (00:38:29):

I'm guessing some of that happened because they've evolved over the years and it's probably a very different initial brand. So it kind of tells me that it's more important to have a logo and a brand that can kind of represent many things that isn't so stuck in a certain positioning, maybe. Does that resonate at all?

Arielle Jackson (00:38:44):

Yeah. Their logo has to do with a very early history. I researched this because I was a nerd out on this stuff. They had some early history as a ball bearings company. And so I guess that logo had some meaning then, but it wasn't so descriptive to being a ball bearing company that they were able to keep it as they evolved into a car company.

Arielle Jackson (00:39:05):

But if you look at their early writing, it's so cool. It's so cool. Long, long time ago they would talk about cars are driven by humans. And our job as a car manufacturer is to protect the humans who drive the cars. That was fundamental formation of the company. So they really knew why they existed. And then they did stuff in I think it was the 1950s when everyone just wore lap bands in the car and they came out with the three point safety harness and instead of patenting it and licensing it, they gave that away for free for everyone because that would make all the world's cars safer and those kinds of company decisions. That's what made Volvo stand for safety. It's not the logo.

Lenny (00:39:48):

Very interesting.

Lenny (00:39:50):

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Lenny (00:41:18):

One question on my mind before we get into these three elements, last question kind of setting context is if I'm a non founder or a PM, I'm just like, oh my God, a branding exercise is going to take months going to suck up all these resources. I don't know what it's going to do for us. What kind of timeframe do you recommend for early stage companies to go through kind of a branding exercise and go through something like this and maybe even later stage, what's reasonable?

Arielle Jackson (00:41:45):

Yeah. It depends on the stage of your company and how much you have already that you have to kind of... It's hard for people to scrap up what they already have. There's a lot of sunk cost fallacy type stuff going on. If you're starting from nothing, I think you can do this in three weeks. The naming process itself because of trademark and domains can take a little longer. When I name companies, it usually takes about a month just for naming, but the whole brand strategy process you could do, if you're a really early stage company in a matter of weeks.

Arielle Jackson (00:42:15):

And I think whatever time it takes you actually is going to save you so much time down the road. It's going to help you save time on company decision making. It's going to help you save time, writing your website. Literally your web copy almost writes itself, if you get this all done right. So it's a small investment of time up front that actually saves you a lot of time down the road is how I would sell it to a skeptical PM.

Lenny (00:42:40):

You've sold it. That sounds very high ROI. Let's get into it.

Arielle Jackson (00:42:43):

High ROI.

Lenny (00:42:43):

So purpose is the first piece. What is that? And then what are some examples of really good executions of purpose that you've seen?

Arielle Jackson (00:42:50):

Sure. So your purpose is why you do what you do. It makes people want to root for you. And it has a big role in aligning people to come want to work for you and to have employees all feel like they're part of something. I like to think of it as we exist to blank. And whatever that blank is your purpose. Do you want to hear about examples or do you want to hear about what makes a good purpose?

Lenny (00:43:14):

Both would be most excellent.

Arielle Jackson (00:43:16):

So a good purpose, it explains the change you want to see in the world irrespective of financial gain. So people often get hung up on mission and vision and values and all this stuff. And values are fine. They're internal. I'm not going to talk about those today, but I don't care about mission and vision. I just want one thing because people can only remember one thing and it's your purpose and it's why you do what you do. And when you articulate this really well, it helps you make company decisions, it exists on a 10 year frame. So everything we talk about with product positioning, it's pretty malleable. It exists on an 18 month frame if you're a early stage company, so it can evolve, whereas your purpose is pretty much going to stay the same for 10 years. It's that north star.

Arielle Jackson (00:44:03):

And it helps align people in the company and it helps the public want you to win. I worked at Google right out of grad school and Google's purpose was to organize the world's information and make it universally accessible and useful. And I thought every company had a purpose that everyone at the company knew. I just thought that was my first real job. It turns out that's not true. And Google's actually been amazing at this. I had a person in my last cohort who had recently left Google when they were like, I don't know, 80 or a hundred thousand people. He said everyone still can say that. That's amazing. But I joined, it was like 1400 people. And by the time of your first day, you already knew that. It was part of your hiring process.

Arielle Jackson (00:44:51):

It was part of your onboarding. It was in your offer letter. It was everywhere. And I just thought that was really cool and a good purpose. One that is kind of related to financial gain, but I still think is cool is Stripe's, which is to increase the GDP of the internet. I think that's really well said and cool and just gets you thinking about the internet as a country. I don't know. If you're an internet person, it makes you want to root for them.

Arielle Jackson (00:45:21):

Nike's is awesome. I wrote Nike's down because I don't remember it, to bring inspiration and innovation to every athlete in the world. And if you have a body, you are an athlete. It's not just about LeBron it's about me and how was my Peloton ride this morning too? So those are some famous companies. I could tell you a little bit about some that I've worked on that I think are pretty cool that are companies you may not have heard of yet, just because sometimes we get hung up in like thinking Stripe and Nike and Google are awesome names because of all the meaning we have behind them. And I want to talk about some companies you may not have heard of because you can have a good purpose and not be Stripe and Nike and Google.

Lenny (00:46:07):

Yeah. That'd be awesome. And by the way, the purpose, should it be a sentence? Is that the general-

Arielle Jackson (00:46:08):


Lenny (00:46:08):

... guideline. Great.

Arielle Jackson (00:46:09):

So you can introduce yourself at a conference. You're the keynote speaker at a conference and I want you to introduce yourself and I want you to go, hi, I'm Lenny, I'm the founder of the company X, and we exist to blah and say it and have that feel natural.

Lenny (00:46:21):


Arielle Jackson (00:46:22):

And it should make people want to hear what else you have to say. And the other thing it should be able to do is be the header for your about page. So meaning we exist to blah, blah, blah, blah, blah. But you would just take out the we exist and say the verb and start there. That could be the header for your about page. So one company I worked on, First Round company, they're called LogicLoop and it's an operations automation company.

Arielle Jackson (00:46:48):

You can think of it almost stuff like a no code, low code platform to automate a lot of the operations data based work that people have to do. And we did this whole brainstorm and I really liked their purpose. You can look at their about page. It will be right there it's to make operations data work harder than operations people. And if you ever have worked in operations or have friends who have, they work really, really hard and it can be kind of thankless. So it gets anyone in that field to root for you. Your data should be working harder than your operations people.

Lenny (00:47:21):

Disclaimer, I'm an investor in LogicLoop, and I love that you worked with them.

Arielle Jackson (00:47:24):

Cool. Awesome. And then another one that I worked on of another First Round company, they're called Woolf. They're informed by the UC model where there's a bunch of individual schools that all exist by themselves, but they get something from being part of a larger organization. And what they do is they provide accreditation through being part of the larger Woolf University, but every individual college can still operate as their own independent college.

Arielle Jackson (00:47:52):

And so their purpose is to increase access to world class higher education and ensure that it is globally recognized and transferable. So this idea of you should be able to take a class from the best instructor online and then go travel to Australia and take a class there and then go to China and take a class there and get the best education that the world can offer.

Arielle Jackson (00:48:15):

Another one that I worked on a while ago is Alt. I think they've recently gone through a little bit of like a rebranding, but theirs was to increase the transparency and liquidity of alternative assets. And in their case, the product positioning was really about making sports cards as easy to invest in as stocks. So the idea of alternative assets in this case are not private equity and hedge funds in real estate, but alternatives to alternatives, like sports cards and Pokemon cards and art.

Lenny (00:48:45):

Awesome. Those are so many awesome examples. That's going to be useful for people to wrap their head around what a purpose might be. Execution wise, do you just kind of open up a Google doc and just start writing out ideas and brainstorm a little bit and just kind of keep refining with your team?

Arielle Jackson (00:48:58):

I actually stole this exercise or borrowed it from [inaudible 00:49:03] that I actually think adds some structure to that. If you do it that way and it works for you, that's awesome. But if you want to go in and go through a process to get there, what I like to do is list all of the cultural tensions that are happening in the world that are relevant to your business first. And so for Alt, that would be things like there's an increase in interest in alternatives. People who are now in their 30s are nostalgic for things that happened in the '90s There is at the time really low interest rates and people are not getting any sort of edge off of investing in the things that their parents used to invest in. So those would be examples of cultural tensions. Cultural tensions are zeitgeist, their things that your audience might be thinking of.

Arielle Jackson (00:49:51):

They're things that they may be even subconscious to them, their current events. So you make a long list of all of those. Then you make a long list of all the ways that you might describe your brand's best self. And this is related to your product positioning, but let's say you haven't done yet, so just think of it as your brand's best self. How would we want someone to describe us? When everything works perfectly, and our product really delivers, what does it deliver? And again, bullets, just ways that you would talk about that. And then you pick one from each side, that's really the best articulation of what's happening in the world, what your product delivers, and with that context, now you're primed.

Arielle Jackson (00:50:30):

With that context in mind, now you do the brainstorm of, we exist to let me finish this sentence, and even before you get there, sometimes it's helpful to do the world would be a better place if. So for my company, the world would be a better place if, and finish that sentence and then go into the we exist to.

Lenny (00:50:49):

Wow. I'm so happy I asked that question. By the way, is there also a place we can point people to that want to do this exercise? Is there another First Round interview post, or I know you have a course on this too.

Arielle Jackson (00:50:59):

Yeah. There's another First Round review article it's called Three Moves Every Startup Founder Should Make, something like that

Lenny (00:51:07):

Great. I will find it and I'll add it.

Arielle Jackson (00:51:09):

Yeah. Okay. Awesome.

Lenny (00:51:10):

Amazing. Okay. Let's move on to the next part, which is around positioning, which is a big deal. First, just what is positioning? And then I'd love to know just what tells you may have a positioning problem, that's something you should really focus on?

Arielle Jackson (00:51:23):

Okay. So positioning is the space that you occupy in your target customer's mind and everything you can do to influence how they describe your product. You have a positioning problem if I ask 10 of your customers or 10 of your employees what the company does or what the product does. And I get multiple answers. And unfortunately that's the case for most companies. It's okay if the answers are tiny slight variance on the same thing, but I have actually done this with some later stage companies [inaudible 00:52:01] my first step is often I go in and I interview 10 people, and the 10 people are everyone from execs to people who talk to customers to a few customers. And when you get 10 people saying 10 wildly different things, you have a positioning problem. Other ways you might know that if you have a positioning problem is if you can't explain what you do to me in a sentence that's, you have a positioning problem.

Lenny (00:52:25):

That's a high bar.

Arielle Jackson (00:52:26):

Yeah, it is. And when I first started consulting, I would spend the first meeting with a founder, just totally cold. Hey, tell me about your company. And they would take 30 minutes to tell me about their company. And at the end of 30 minutes, I would pretty much get it, but it always took the first 30 minutes. So now when I engage with a new company, I have them fill out this little worksheet beforehand. And one of the questions is what do you do? And they have to write in a box that's kind of paragraph length.

Lenny (00:52:55):


Arielle Jackson (00:52:56):

And then I go in and I ask questions about that. And ultimately we get it to sentence length.

Lenny (00:53:00):

Amazing. Okay. How do you go about figuring out your positioning? Big question.

Arielle Jackson (00:53:05):

Yeah. So I start with your audience. Who's this for? And we really think about what's the broadest set of customers or users that you might have and narrow in from there to a target audience, which is who are you outwardly going to try to acquire for the next 18 months?

Arielle Jackson (00:53:25):

You can think of it like concentric circles. The biggest circle is your TAM. As you get smaller, there's five parts to it. So the biggest circle is circle one, circle two, circle three, circle four is your target audience. All of the circles have to be contained within the bigger circle. And then the dot in the middle is your model persona. So this is actually like a person with a name and an age and a location and a job and feelings and priorities and interests and all of that.

Arielle Jackson (00:53:54):

And so we talk about the model user and the target audience, the target audience again is who will you outwardly try to acquire for the next 18 months? If you're an early stage company, it's very possible that you're going to acquire people outside of that circle, in the next circle or even the bigger circle, but they're not who you're actively going out to try to acquire.

Lenny (00:54:15):

Can I ask you a couple questions on the person?

Arielle Jackson (00:54:17):


Lenny (00:54:18):

I'm doing some writing and research into this stuff. How specific do you suggest people get with this person right at the middle? I love that it's an actual person, I guess not a real person, but a very descriptive [crosstalk 00:54:29]

Arielle Jackson (00:54:29):

Can be a real person or an amalgamation of not real people. So with the target audience, I like to think of it as something you could name. So with Eero, it was tech savvy dads. It's a category of people. And then the model persona, or that individual user who represents a tech savvy dad for them was this guy who had teenage kids lived in suburban St. Louis, had a 2,800 Square foot house that was made of brick, worked at home on Fridays. His kids were into gaming. He was the VP of sales at a company that was tech adjacent, but not tech. He was more of like a tech enthusiast than an actual software engineer. We knew a lot about him. I could tell you a lot about him. It's kind of robust, but tech savvy dads was the way to represent him and other people like him, that would be their target audience.

Lenny (00:55:22):

A lot of founders have trouble recognizing that going very focused and niche is a good idea versus man, I'm just going to have these 10 people in the world that really want what I want. What have you found to be the reason it's very powerful and important to start really focused?

Arielle Jackson (00:55:37):

Yeah. So when you are an early stage company, the worst thing you can do is try to be everything to everyone because you don't have enough runway. You just don't have enough of anything to do that successfully. The best thing you can do is find an audience that is big enough, that if you got your significant market share among that audience, you'd be a giant business. And tech savvy dads is a pretty big audience. Also that's just who your outbound going to try to acquire for the next 18 months. I'm a tech savvy mom. I live with a tech savvy dad. I have an Eero system. It doesn't mean everyone you'll ever acquire must be in that audience, it means that is who we're focused on acquiring.

Lenny (00:56:24):

Awesome. I took us off course around the positioning process. I think we kind of went off course with concentric circles model. So I'll give it back to you to keep going.

Arielle Jackson (00:56:36):

Yeah. Okay. So the way that I like to run positioning exercise is to start with who is this for? And then what is the problem that they have? There's some problem usually that these people have, they may not even be aware it's a problem, or they may not be experiencing the problem as particularly troubling, but there's something going on for these people. And then how do they address that problem today? So they do something, they're buying something, they're have a workaround, they're doing something today. And that something might not be another startup or your direct competitor. It might be the old way of doing things, but they're doing something. So we go through who is it for? What's their problem? How do they address it? And then what do you make?

Arielle Jackson (00:57:20):

How does it work? And what would you want a user of your product or service to tell another? And that's kind of if you answer all of those questions, it ultimately leads into this classic four statement, which is not something I invented, it's something that's been around for 40 or 50 years. And I learned it when I was 22. And I think it's one of the most powerful tools in marketing. It can feel like mad libs if you just approach it cold. But if you've gone through that work of defining who is it and what's their problem, all it is a distillation of that. So that statement is for target audience who there's a statement of need or opportunity. And then you say our product name is a category that has a benefit, unlike the old thing they were doing, our product works this other way.

Lenny (00:58:10):

Awesome. And we'll link to the post that actually has that so people don't have to write this all down. That last piece you mentioned, I hadn't heard before, the idea of what will they tell other people or how will they describe it to other people? Is that right?

Arielle Jackson (00:58:22):

Yeah. So I believe that great benefits if you've defined your benefit really, really well will actually be the thing that will be the H1 on your homepage and will be the thing that you want someone to tell someone else. Think about Square Stand and turn your iPad into a point of sale. Turn your iPad into a point of sale. Yeah. If I went to a small business owner and they were having drinks with a friend, who's also a small business owner, what would I want them to say about the Square Stand? Oh yeah. I just got the Square Stand. It's this really cool new register that turns my iPad into a point of sale. That's pretty much exactly what I want them to say. And so if you can write that line, that is your ideal benefit, what you want people to say, and it's something that your target audience would actually say, that's great.

Lenny (00:59:12):

Interesting. I love that. That makes a lot of sense. For people trying to go through this exercise, you always have such a good answers to how actually the process of coming up with say you're positioning this case, is it again, you pull up a doc and start writing things or is there something even more structured?

Arielle Jackson (00:59:28):

Yeah. There's something more structured. I have kind of a worksheet that goes through all those things we just talked about. So it's like, who is it for? What are they doing today? All those questions we just talked about, it's more like a structured brainstorm. There's an exercise I really love that I've called the bar test that is helping you get everything you've written into human language because one of the really big pitfalls I see, especially for B2B companies, but really for everyone is they write in a way that people don't talk. So the document, when I get the first draft back from founders often has things like leverages and empowers and nobody talks like that. And so getting this into turns your iPad into a point of sale blankets your home in fast, reliable wifi, records your screen and cam at the same time, really basic stuff that it describes your product in a way that someone would actually say that's the type of language that I think people want to use.

Arielle Jackson (01:00:28):

First of all, you defined your target. Now you pretend to be someone in your target, having drinks with someone else in your target at a bar and you have to be able to say, hey, I just started using product name. It's this really great category, that benefit. And the other person goes, hm, tell me more or that's cool, what do you mean? Or some other similar prompts. And then you have to say your differentiator. You actually have to say it out loud. And if you run through that test and it's actually stuff people would say out loud, then you've done a pretty good job and you can start using that copy publicly.

Lenny (01:01:07):

That is very cool. I have not heard this bar test before and I like that it might happen at an actual bar. Is that also something people can find online or is that they write it down right now?

Arielle Jackson (01:01:18):

Ooh, I don't know if that's online.

Lenny (01:01:20):

Okay, cool. This is it. Exclusive.

Arielle Jackson (01:01:22):

Yeah, that's in my course, and we talk a lot about that and we go through the exercise like a real role play in the course, but yeah, take some notes.

Lenny (01:01:31):

I like that a lot.

Arielle Jackson (01:01:33):


Lenny (01:01:33):

Your point reminded me of an email I just pulled up that I got from ADP, your point about just you want to make sure you're branding is something that feels like something you would say to a person. So it's like ADP, which is a security service for fire, like alarms. I got this email, summer's on with fun or our free secure app and more. And then it's like make summer safer and more fun at home or away. ADP, you're not going to make it more fun. What are you talking about?

Arielle Jackson (01:02:01):

See, that's an example of trying too hard. They tried too hard to make it sound colloquial and fun. They're a security system, it should be more like secure your home while you're away. Feel safe when you're on your summer trip. Stuff like that.

Lenny (01:02:16):

They even included a gif of this TikTok'er being like ADP is my MVP.

Arielle Jackson (01:02:21):

Yeah. This kind of relates to brand personality where the brand personality for ADP, I don't know, it's pretty not fun. And so for them, when they put on fun hat, it seems awkward and forced.

Lenny (01:02:36):

That's exactly the feeling I got. And so, yeah, personality, that's our next topic. It's not something I you think about when you think about brand and marketing and plans and so I'm really curious to hear why I think that's important then how to figure out your own personality for your brand.

Arielle Jackson (01:02:51):

So I think personality is one of those inputs that will help define your visual design and it will definitely help define your written copy. And it really comes from this idea of brands are like people. And if you start thinking of your brand more like a person, it's quite obvious that it needs a personality, because all people have personalities. And these days, especially when brands show up in places where people show up, like TikTok and Instagram, your brand certainly needs a personality or else you end up like ADP trying to be fun for the summer, which just feels really off and weird. So personality is one of those things that it's actually the easiest part. I think it's the fastest part. It often ends up an hour and you can get it done. But I have some frameworks I like to use that really just get at are you Mountain Dew or are you Rolex or are you somewhere in between?

Arielle Jackson (01:03:46):

And when you think about brands that have a lot of equity, they really do have a personality. I often talk about Mountain Dew marketing as that marketing that's like trying really hard to be cool and rugged and edgy and fast and kind of teen and Rolex, it's very like Gray Poupon, oh, roll down your window and do you have any Gray Poupon, it's fancy and sophisticated and a little bit aspirational and maybe even a little British. And those two things are really, really, really different. And there's a lot in the middle and not everyone's going to be a Mountain Dew or Rolex, but where are you? And so you can just write it down. I think a lot of these answers come back to like, if you are good with just opening a blank Google doc and like writing down who you are by all means, go for it.

Arielle Jackson (01:04:36):

And if that feels daunting and hard for you, use a framework. And the framework that I like to use has two parts. The first part is based on some academic research by Jennifer Aker and it basically analyzed the top brands in the world and figured out that all brands can be segmented into five dimensions of brand personality. And that really strong brand spike in two of the five. So the five dimensions that she found were sincerity, so this is like, is it down to earth and honest, excitement, it's spirited, this is a Mountain Dew thing, competence, reliable and intelligent, sophisticated, sophistication, which is a charming and upper class and rugged outdoorsy and tough. So sincerity, excitement, competence, sophistication, and ruggedness. And going back to those two brands we just discussed Mountain Dew is rugged and exciting, Rolex is sophisticated and competent and you can do this with any brand who admire or just think about brands you like and kind of deduce them to their two of those five.

Arielle Jackson (01:05:39):

So that's the first step. Which two of those five are you going to spike in? And it turns out a lot of tech companies end up spiking in sincerity and competence just usually does happen that way. Amazon is sincere and competent. Google is sincere and competent. Apple is not, Apple has a little more of that sophistication to it. But in any case, if you just did that, we would end in a world where everyone's sincere and competent or maybe sophisticated and competent. It's like a really boring world. So the next step after you do that is to define five attributes, five brand personalities, thinking about those two dimensions. I like to think about this as a star, five point star and brands need tension to be interesting. So if you tell me we're helpful, we're nice, we're approachable, we're competent, and we're reliable.

Arielle Jackson (01:06:37):

You basically haven't told me anything because you just use three words to say one thing and two words to say another thing. Whereas if you tell me, oh, well we're really savvy, but we're also really approachable. That's kind of cool. Because people who are expert are always approachable. They have to have a little tension and then you want to write them as statements that say we are X, but not Y, where Y is taking X too far. So in the example Google is playful but not silly, so they would say we are playful, but not silly, or maybe Mountain Dew would say we are daring, but not stupid. So taking that attribute a little too far. And so yeah, then you end up with these five statements that are we are X, but not Y. And those are really useful in informing how you write and maybe even what your visual design would look like, and certainly what your illustration style photography style ad copy will be like.

Lenny (01:07:39):

Once you've gone through that exercise and in maybe the other two pieces, where do you put this? Is this just like in a doc that's like here's our brand overview, here's our personality, here's our positioning, here's our purpose. And then you refer back to that whenever you're designing and putting together strategies? Is that how it works?

Arielle Jackson (01:08:00):

Yeah, you could do it that way. That's definitely one way of doing it. That's a good start. I think that one other place where it shows up, like we talked about that visual style guide that everyone has, that they give to an agency or copywriter who's writing on their behalf. I think these should all be inputs into that doc that you end up sharing. I think it should go into any onboarding you do for new employees so that they understand who the company is. Any partners that you're marketing with, co-branding, all of that, it should really be think of it as your little brand Bible about who you are. And also it should be revisited when you're doing, let's say a new product or to make sure does this need to be updated or does this new product need to fit into who we are?

Lenny (01:08:40):

What do you call this document/place?

Arielle Jackson (01:08:44):

When I take all those three components and then add a bunch of other stuff, I call it a creative brief, which is the thing you would hand to an agency or a writer who's writing on your behalf. It would include some other things too, that we didn't talk about, like creative inspiration direction. So picking visual clips and written clips and all these things that you like and that you don't like, so you can show both positive examples and counter examples to the thing you're looking for.

Lenny (01:09:09):

Awesome. Thank you for all of that. There's so much juice there. I think people are going to have to listen to this a couple times to get all the learnings. Before I let you go, there's two other areas I wanted to dive into. But I'll keep them brief because I know we're going long. One is about getting PR and just a question I wanted to ask you while I had you, founders and even bigger companies, they're always like, how do I get PR? How do I get press for my product, even though it's sometimes a waste of time. Do you have just any tactical advice for startups hoping to get some PR?

Arielle Jackson (01:09:43):

You mean initial coverage around a launch or ongoing?

Lenny (01:09:47):

I'd say early on, yeah, before the launch.

Arielle Jackson (01:09:49):

Sure. So the first one is to get your story straight. So, so many times I have founders come to me and they're like, hey, we need help with this announcement. I'm like, cool. What's the announcement? And back to the 30 minutes until I understand what the company is, so if you can't describe it to me in a sentence, your reporter is certainly not going to understand in a sentence and they won't be able to describe it to their audience in a sentence. And so really getting your story straight, all the stuff we talked about specifically around product positioning is so key. Almost always when someone comes to me and says, I'm ready to announce, we go back to positioning first. Also make sure that your website is ready for the traffic you're going to drive to it, that you're not driving traffic to a name that you're going to later scrap.

Arielle Jackson (01:10:32):

Are you really ready for this? So go back to all the other things we discussed first and then having realistic expectations about the outlets that will cover you and the time it will take to get them. So a lot of people will be like, I'm launching next week. And it's like, well, cool that you're doing that, but no reporters going to cover you next week. It just doesn't work like that anymore. Five years ago, eight years ago, founders could really dictate the date of a launch announcement, they could brief three to five outlets under embargo, which means like you all can't tell our secret news until we tell you at this time you can publish. And at that time, three of the five would all file a story and write, and it just doesn't work like that anymore. These days for early stage startups, we're almost always running the launch announcement as an exclusive, which means you give the news to a single outlet.

Arielle Jackson (01:11:19):

And they're the only ones who get to write about it. You can obviously still do all your owned and operated stuff, your blog, your social, your investors, your friends and family, but they're the only like news outlet who gets to write about it. So having an expectation that this is probably going to be an exclusive, it's harder than ever to secure funding for a seed stage company and funding in and of itself is not that interesting anymore. There's so many bad companies getting funding. There's so many good companies getting funding too just more than ever. And the number of reporters and the number of outlets that are covering it is just less than it used to be. So really just thinking about like, well, who writes about this space? Do they write about company's at my stage?

Arielle Jackson (01:12:08):

That's another really big one is, hey, we want the New York Times. It's like, cool, no one's at the New York Times has ever covered a seed stage startup unless it's crazy for the last five years. Who do you think is going to write about you? But there are still outlets that do. The other one is don't do a straight funding announcement. A lot of founders raise money and they're like, cool, let's announce. It's like, no, we'll use that funding announcement as a news hook to tell a larger story and a larger story might be your products available. You have reference customers, you have momentum, you have some great partnership that you're announcing. There's something else going on, not just your funding and using your funding as part of that initial launch is great, but what else are you announcing?

Arielle Jackson (01:12:55):

The last thing is really about making what you do interesting and relevant so that it's not just interesting and relevant to you and the three other people who worked there at the time, but interesting to all the readers of whatever outlet you're trying to target. And so an example of that is I worked on this company, Vitable Health and the founder, Joseph, he created a product for hourly workers that their employer would buy and it costs like $50 per person per month. And what it does is it provides urgent care and primary care. So these hourly workers who make too much to qualify for Medicaid and too little to pay their health insurance premiums, and so primary and urgent care for hourly workers. And we tied it into this idea of the great resignation and small businesses not being able to hire hourly workers, which was like a big trend end of 2021, and the company operates in Philadelphia and Delaware, and we were actually able to get him the Sunday after Christmas, Philadelphia Inquirer story.

Arielle Jackson (01:13:57):

But it was all about making this daycare and this restaurant in Philadelphia into heroes because they offered this cool benefit to their hourly workers. And so the headline was perfect for them, but it wasn't like here's Vitable and here's what they announced and here's, it was like, hey, look at this cool new thing that local businesses are doing to attract hourly workers. And so think about your company in a way to make it interesting and relevant and don't sleep on local preps.

Arielle Jackson (01:14:23):

If you have a local business or a local story or local customers, this was a huge thing at Square. We turned all of our customers into heroes and went after local press. Most PR firms that service the tech community aren't experts in local press, but if you have a way to make some connections with some local press, they are the ones hungry for these stories more than the New York Times and the Wall Street Journal.

Lenny (01:14:50):

What a good tip and most likely they're much more open to writing about you versus New York Times or Wall Street Journal. Cool. Okay. So I want to ask you one question about hiring marketing real quick and I'll keep it short just because I know we're going to run out of time. When should a startup hire a full-time marketing person in your experience?

Arielle Jackson (01:15:08):

When you have a lot of problems that you're trying to solve that would be better solved by someone who knew what they're doing, or when you have a bunch of freelancers and agencies that are becoming too hard to manage by yourself.

Lenny (01:15:21):

When do you find that usually ends up being... Is there kind of a heuristic-

Arielle Jackson (01:15:25):

Yeah. Ballpark, it kind of depends if you're a marketing driven business or a sales driven business. So if you're a sales driven business and you don't have a repeatable sales motion, it's not yet time to hire a marketer, get that repeatable sales motion, and marketing's job is to bring you more marketing qualified leads. So that's one, so that kind of depends. If you're a marketing driven business, it generally seems to me like it happens around 10 people, the founders doing most of this themselves, they're not doing the best job usually or they've hired agency here, a freelancer there to kind of cobble some stuff together. And they now realize like, okay, if I had a person who would be able to do all of this and manage these agencies and freelancers, this would be a lot better.

Arielle Jackson (01:16:13):

It also is do you have a one point in time project? Do you need to do positioning? Do you need a website? Do you need a name? Do you need to run a test of Google ads? Those things are all discreet when it becomes this is ongoing work that needs to happen over time. It's better to think about hiring a marketer and really what kind of marketer do you need? Do you need a product marketer, a performance marketer, a comms person, a creative person? Ideally everyone wants all of that. But I kind of like that idea of a T-shaped marketer who's really deep on one of those functions, but knows enough to be dangerous across all of them.

Lenny (01:16:48):

I think we're going to need another episode just about that one topic. I have so many questions I want to ask, but I need to let you go. That'll be V2. Before we do that, we've gotten to the very exciting lightning round where I'm just going to ask you quick questions and you just give me a quick answer and we will knock through them all. Does that sound good?

Arielle Jackson (01:17:06):

Sounds great.

Lenny (01:17:07):

What are two or three books that you recommend most to other people?

Arielle Jackson (01:17:09):

In marketing land, definitely the book called Positioning: The Battle for Your Mind. It's from 1980, it's still my favorite marketing book. Another recent marketing book is Alchemy by Rory Sutherland. It's like my favorite area of reading is behavioral science, psychology meets business. And that's in there. For fiction, I just read The Vanishing Half by Brit Bennett. It was awesome. I then read her other book called The Mothers, but I think The Vanishing Half's better.

Lenny (01:17:36):

Awesome. I will check that out. What's a favorite podcast or even newsletter on marketing?

Arielle Jackson (01:17:41):

I love Nick Sharma's weekly newsletter. He's a growth marketer. He started his career I think at [inaudible 01:17:48] water. So he does a lot of CPG type DTC. He has a great marketing newsletter that comes out every Sunday night. On podcasts, I love How I Built This. I know that's already really popular, but I love that one. It's not really marketing, but just general business. The First Round podcast in depth is pretty great. Lenny's podcast I've been listening to is awesome. And then my friend Jasmine from The Concept Bureau has a marketing podcast called Unseen, Unknown. And it's kind of about culture and branding and how these things and society and trends. It's not like straight marketing. It's kind of more of the culture and sociology that informs marketing.

Lenny (01:18:30):

Wow. That is a lot of good stuff. What's a recent movie or TV show that you've loved?

Arielle Jackson (01:18:35):

This is more embarrassing. How many movies have you seen in the last year? Just curious.

Lenny (01:18:41):

Me? A lot, on streaming services. Way too many also, if that's where you're going or have you seen none?

Arielle Jackson (01:18:48):

Well, I've seen maybe four and they're probably all on Disney+.

Lenny (01:18:53):

You're winning. That's excellent.

Arielle Jackson (01:18:56):

I would say I really like some of those Disney Pixar movies, Luca, Encanto. Those are all really great. I mostly only watch movies with my kids, but I'm pretty excited. I had a celebrity crush on Anthony Bourdain and I'm excited to watch his new documentary if I ever get around to it. And TV shows I'm equally bad.

Lenny (01:19:16):

Okay, great.

Arielle Jackson (01:19:16):

And there's this little Netflix show called Old Enough. It's a Japanese show with subtitles about sending toddlers on errands in Japan. They like go by themselves. It's 10 minutes. They're awesome. My whole family watched them together. It's really cute.

Lenny (01:19:29):

Old Enough. I'm going to check that out. Okay. Two more questions. Favorite interview question when hiring a marketing person?

Arielle Jackson (01:19:35):

It's probably tell me a project you're proud of. Tell me about a project you're proud of, is just really open-ended and get to hear a lot about a lot of things that way. And then maybe runner up is tell me about a campaign you recently come across that you were not involved with that you thought was cool.

Lenny (01:19:53):

Hmm. Love that. Okay. Final question. Who else in the industry do you most respect as a thought leader?

Arielle Jackson (01:20:01):

In the marketing industry?

Lenny (01:20:02):

In the marketing industry? Yeah, sure.

Arielle Jackson (01:20:04):

I guess old school thought leaders, David Ogilvy, Rory Sutherland, Seth Godin. New school thought leaders, we mentioned Nick Sharma. There's a woman named... I'm probably going to butcher her name, Anna Andjelic. She has a newsletter that I didn't mention before. It's called the Sociology of Business. That's really good. She's a CMO, chief brand officer type. She kind of turned around Banana Republic recently, which was cool. Emily Hayward from Red Antler. I also really like Ross. I don't know this guy, but Ross Simmons from Foundation, which is a content marketing agency. I'm not a content marketing expert, but he really is. And I think he puts out some good content.

Lenny (01:20:48):

Man, these show notes are going to be a long list of great stuff. Arielle, thank you so much for being here. There's just so much jampacked knowledge. I don't know if people were prepared when they started listening to this and so congrats on making it through and I hope you're probably going to go back and listen again and again. And so again, Arielle, thank you so much for doing this. Two last questions. Where can folks find you online if they want to reach out or ask questions and how can listeners be useful to you?

Arielle Jackson (01:21:14):

Sure I'm on Twitter and LinkedIn. Twitter, I'm hiimarielle. And if you're interested in this stuff, but feeling overwhelmed, I will plug my Maven course. I teach a course on startup brand strategy that covers everything we talked about in this hour, or this is more than an hour now and kind of with a little more hand holding and feedback. So it's a crash course on all this stuff. The four founders that takes two weeks and you go through all of this and that next cohort of that, I think we're on cohort four will be this fall. So you can apply for that course at

Lenny (01:21:57):

Amazing. And I guess that's how listeners can be useful to you.

Arielle Jackson (01:22:00):


Lenny (01:22:01):


Arielle Jackson (01:22:01):


Lenny (01:22:02):

All right. Well great. All right, well thank you again, thank you again and [inaudible 01:22:07].

Arielle Jackson (01:22:07):

Thanks so much, Lenny. It was fun.

Lenny (01:22:09):

Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at See you in the next episode.