David Elikwu speaks with Arielle Jackson, who is the marketing expert in residence at First Round, and also an amateur jewelry maker.

Arielle built a well-storied career working in marketing at Google, Square and Cover. Now sheโ€™s a force multiplier at First Round, helping startups pop! Sheโ€™s also teaching a course on Maven called Startup Brand Strategy.

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๐Ÿ“น Watch on Youtube

๐Ÿ‘ค Connect with Arielle Jackson:

Twitter profile: @hiiamArielle

LinkedIn: Arielle Jackson

Maven: https://maven.com/arielle/startupbrandstrategy

๐Ÿ“„ Show notes:

Where Arielle grew up [2:11]

How bad we are at calculating odds [9:17]

One of Arielleโ€™s favourite books [10:40]

The psychological games [10:33]

Paradigm shift of how I had previously thought about email [17:38]

The framing of a future world [21:16]

How Arielleโ€™s early habits helped her [24:10]

Where Arielleโ€™s industriousness came from [26:40]

How important early work experience is [30:51]

Learning what you don't want to do [35:23]

The secret to being great at math [37:21]

Arielleโ€™s early days at Google [39:04]

Breaking out of her comfort zone [48:22]

The reason she left Google to join Square [50:19]

Staying in a role too long makes you stale [53:09]

The impact as an individual when the company is smaller [57:09]

How Arielle ended up at First round [1:06:16]

The future of work [1:09:08]

The personal Category Pirates [1:13:09]

Reid Hoffman, The startup of you and The Alliance [1:13:42]

Should you optimise for reputation or skill? [1:14:29]

Emperorโ€™s new clothes effect [1:18:39]

๐Ÿ—ฃ Mentioned in the show:

Rory Sutherland


Robert Cialdini


Dr Harvey Karp

The Happiest Baby on the Block

Mike Maples Jr.

Malcolm Gladwell



First Round

Josh Koppelman


Brett Berson

Chris Lochhead

Reid Hoffman

The Startup of You

The Alliance

Full episode transcript below

๐Ÿ‘จ๐Ÿพโ€๐Ÿ’ป About David Elikwu:

David Elikwu FRSA is a serial entrepreneur, strategist and writer. David is the founder of The Knowledge, a platform helping people think deeper and work smarter.

๐Ÿš€ Career Hyperdrive

Career Hyperdrive is a live, cohort-based course that helps people find their competitive advantage, gain clarity around their goals and build a future-proof set of mental frameworks so they can live an extraordinary life doing work they love.

During this course, you will make the leap from 'going with the flow' to actively crafting your journey. And youโ€™ll join a community of ambitious peers who will hold you accountable for betting on yourself.


๐Ÿงญ The Knowledge

On The Knowledge Podcast youโ€™ll hear from the best and brightest minds in business, entrepreneurship, and beyond. Hosted by writer and entrepreneur David Elikwu, each episode features in-depth interviews with makers, thinkers, and innovators from a variety of backgrounds.

The Knowledge is a weekly newsletter for people who want to get more out of life. It's full of insights from psychology, philosophy, productivity and business, all designed to help you think deeper and work smarter.

Website: theknowledge.io

Podcast: plnk.to/theknowledge

๐Ÿ“œFull transcript:


Arielle Jackson: If I stay here until I'm 30 and don't go do something else, I'm going to be here when I'm 40 and 50, and like, I just need to leave. I need to go do something else. At some point, staying at the same company becomes a liability. I knew how to operate at Google. I was very effective there. Did I know how to operate anywhere else? Could I take what I learned there and be back on that exponential growth curve rather than what had become a plateau.

David Elikwu: Hey, I'm David Elikwu, and this is The Knowledge. A podcast for anyone looking to think deeper and work smarter. In every episode, I speak with makers, thinkers, and innovators to help you get more out of life.

This week, I was speaking with Arielle Jackson, who is the marketing expert in residence at First Round and also an amateur jewelry maker, which is equally awesome. And we really dug into some of her experiences at Google at Square, at [00:01:00] Cover, which is a startup that she built with her husband, which eventually was acquired by Twitter.

You know there's so much going on. This was such a fantastic conversation and we talked about her early inspirations to potentially pursue a medical oriented career, but then eventually being led into marketing where she's built a well storied career. You know, she's probably been behind or seeded some of the marketing for a lot of great startups that, you know, and love.

And I am equally as excited to share this with you as I am for the followup conversation, which surely needs to happen because there's so much more that I didn't get to ask.

You can get the full show notes, transcript, and read my newsletter at theknowledge.io.

You can find Arielle on Twitter @hiiamArielle, and also you can catch her awesome course on Maven, which is called Startup Brand Strategy.

If you love this episode, please do share it with friends and strangers. And don't forget to leave a review wherever you listen [00:02:00] to podcasts, because it helps us tremendously to reach other people. Just like you.

I wanted to know where you grew up and then we can talk a bit more about your background.

Arielle Jackson: Sure. So I grew up in LA, which is actually where I live now. I came home after, a while away. But I grew up in LA in this kind of weird neighborhood in west LA that's like between a lot of things. But it's probably closest to this neighborhood called Palms. And it's, it's like a kind of normal neighborhood right in west LA.

David Elikwu: Okay. What was it like growing up there?

Arielle Jackson: It was nice. I went to a private school that actually my son now goes to, which is one of the reasons we moved back to LA in Santa Monica. And so it was interesting being the child of, you know, I was definitely like upper middle class family, but I went to school with a lot of people who were very, very upper-class. And So it was interesting being, you know being in a world where I didn't have what all those kids had, but I had a lot compared to like most of LA. So that was kind of interesting experience. I [00:03:00] think you know, being a parent at that school now is the whole, whole nother level of interesting, but yeah, we would like, you know, drive to Lake Arrowhead for our vacations And my friends would like fly to Hawaii first class and stuff. So it was an interesting time, but I actually am still best friends with the girl I went to. I met her in kindergarten and we're still like, best friends.

David Elikwu: Do you feel like your kids fit in now more with that cohort than you did when you were growing up?

Arielle Jackson: It's interesting. I mean, I definitely have more as an adult than I did as a child, so I worry a lot about it spoiling my children And, it's really important to me to raise them in a way that they understand the privilege that they have. That's like really important to me. In fact, yesterday we went over to one of my, well, my older son he has he's in second grade and he has a lot of friends, you know, same kind of thing I grew up with, you know, like we're going on a road trip for our summer break. and his friends are like, you know, flying private to Aspen and stuff. We went over to one of his friend's house, really nice family, but they live [00:04:00] in like a giant house with a trampoline and a zip line in the backyard. And it's super fun to go over there. But, you know, we, we have a nice house. We live in LA. It's like, you know, we're quite fortunate, but when you have friends like that and you're eight and you don't really know the difference and you ask your mom and dad, like, why don't we have a house like that and a zip line in our backyard and it's interesting to navigate those conversations. I think it's really important for him, for my older son to know, you know, everyone lives differently and what's important in your house is that, you know, you have parents who love you, you have food, you have clothes, you know, you can make yourself entertained. You have a brother, like all this stuff that matters and not like how many Beyblades you have in your collection or whatever. But yeah, it's, it's, it's interesting as a parent to try to navigate that, even from a place of privilege.

David Elikwu: Yeah, I think that's so interesting. What you were saying. Just reminded me of a memory that I have from when I was a bit younger. So I think probably when I was maybe 13 or 14, so we had [00:05:00] these just some family friends that I think my dad had gone to school with years and years ago, but we're definitely now not in the same or at the time anyway, not in the same kind of like social class. And I had gone to their house to go And play essentially. So we were just like having to get together, but also with a few other friends. And so there was a time we were supposed to get there and we were running late. So I remember we drove up so we're pulling up to their house. Their house is not even necessarily close to the road. you have to go on this winding path full of like trees and foliage off the main road. And so you pull up to the house and I just saw like a bunch of cars and I was like, oh my gosh, we're so late. And I hadn't met. I, don't think I'd even know. I think I had met him, but I hadn't met anyone else. So I didn't know, who else was going to be there. And like, you know, it was a bit anxious and I was like, oh my gosh, all these cars are here. We must be so late. And then we get there and we were the first ones there. And all of cars, all of the cars were his dad's cars.

It's funny when you get to see, I guess, I don't know, like the breadth of experiences that different [00:06:00] people have and in some ways it doesn't necessarily make people any different, because I think if I hadn't seen that in terms of my relationship with my friend, like. Well, first of all, I don't think it necessarily changed, but also I wouldn't necessarily have seen him any differently or, but I think when you have that wider context it maybe changes how, you see yourself within that broader spectrum.

Arielle Jackson: Yeah. I mean, kids are kids. They just want to play with their friends. Right? Like in the end, you just wanna play with your friend. You don't really care how many cars his dad has. But it creates a interesting conversation about your place in the world and what you know, and what is normal. And you see all these like polls, even that say like, you know, have you seen these questions where they're like, what percent of your country do you think makes more money than you? What percent of your country has this degree? What percent? And people are really bad at actually like predicting the truth. And I think that's the kind of warped sense that it gives kids. You know, what percent of the country has five cars and maybe you would think higher after you went to your friend's house. And really he was such an outlier, right?

David Elikwu: Yeah, that's a [00:07:00] really interesting point that you bring up as well. I think particularly in this age of social media now, it's interesting how widely our baseline gets skewed. And actually, I was just thinking about this earlier. Not that long ago, I was thinking about the fact that I think because I'm in this weird startup world now, which is very different from the world that I grew up in and I listened to loads of podcasts and I seen loads of people when everyone has these big exits and makes millions and millions. And then I think I saw a story of someone else that had you know, start a business and raised a few million and it was on Twitter and someone was commenting about whoa, how much this is. Oh my gosh. It's like generational wealth and I felt bad, but my first reaction was like, oh, that's not huge compared to some of the rounds that you see.

Like that's just a evaluation of, I think it was maybe like 15, 17 million. And that was not necessarily the main point. The point was someone commenting about, how huge, a number that was. And of course that is so true, like over $20 million for anyone that's a, that's a colossal amount and that [00:08:00] is generational wealth. But in my mind, the first reaction that came to, my head is like oh, you're not overreacting. This is not huge. Compared to working in tech, seeing tech multiples all the time, where every day, you know, if your seed round doesn't start with more than 2 million, then it's almost like you're a failure. And I think, you know, at the company that I work at, we just did a series C, it was about 128 million. So again, you very quickly just have this skewed perception of what success looks like and what wealth or money or privilege or any of these things can look like.

Arielle Jackson: Yeah. I mean, that happens with everything, right? Like even I was thinking about like a kind of dumb example, but like with coffee, right? Like if you are into coffee and, you know, I used to in high school, I would like get a Starbucks latte once in a while. I thought it was amazing. And now it's like, oh, Starbucks, I got that.

It's not that great. You know And like you, you go after, like, if you're going to spend money on coffee, you go for like a really good coffee. And so like kind of what the bar for what good is shifts. And then the more [00:09:00] you drink, good coffee, the more you're like, oh, I can't, you know that Starbucks latte, I'll have it in the airport if I have to, but it's not special to me anymore. As it once was.

David Elikwu: Yeah, No you're completely right. And I think even more, we were just saying, reminds me of just in general, how bad we are at baselining things.

So in my newsletter, just this week, I was writing about how bad we are at calculating odds. for example, like the odds of flipping a coin and getting consecutive heads, most people would think like if you were betting on whether it would be heads or tails, if you had to flip a coin five times people's automatic assumption is that coincidences are rare, and it's not going to be head several times in a row. If it's been heads twice, it's probably going to be tails next time. So if you've seen two heads, you're going to switch. But actually it's actually almost technically more likely that it will be another heads. And so it's almost better if, if you had to pick 10 coin flips, you just pick one thing and stick with it the entire time, because the odds of each successive coin flip is equally likely.

So anyway, I know I just went on off on a rant, but the point [00:10:00] is just in general, how bad we are at baselines. And it makes me think about, I dunno, it's like psychologically, it's really interesting. and I'm interested in your perspective because I was just listening to Rory Sutherland on a podcast. And I think actually you just tweeted something from Oglivy recently and Rory Sutherland works at Oglivy.

Arielle Jackson: He's amazing. I'm excited to hear what you heard him talking about, It's amazing. Yeah.

David Elikwu: Yeah, No, so many things. So I I couldn't even summarize everything, but I just learned from listening to him. But I think the main thing is just how easily, first of all, the massive connection between marketing and psychology in the brain, and also just how easily we can be skewed by certain things.

So I think the first thing that comes to mind is Coke had... coke, got in a lot of trouble quite a few years ago now, but they tried to have these, they wanted to have these vending machines where during the summer the cost of a Coke would increase when it was hot. So based on the temperature that the cost [00:11:00] of a Coke would start rising, whereas if they had done it the other way and said, when it's cold, a Coke will be cheaper and just had a higher baseline price, no one would have a problem with it. And so it's interesting how, again, this idea of having baselines, And I know that a big idea in marketing, it skews our perspective of what value is.

Arielle Jackson: Yeah, for sure. I mean, framing is sort of the psychological, I guess, terminology for that. So if you think that the coke costs a dollar. And in the summer, it's going to be a dollar 50, you think like, oh, they're ripping me off. But if the coke always cost a dollar 50 and you're primed and frame to think a dollar 50, and now in the winter, It's a dollar. you feel like you're getting a deal. It's the same exact, you know, economic situation. It's funny.

So I studied psychology. I studied human biology in school, and then I did a master's in psychology, almost became a clinical psychologist. And when I was doing that I took this class on social psychology and, I'm going to butcher his last name. Robert Cialdini was a visiting professor that year. Just happened to be.

And so I heard, he wrote that book Influence, which is like one of the things that's like his number one [00:12:00] bestseller. And he, I think he was teaching in Arizona at the time, but he, he became like a visiting professor and I got to hear like one lecture from him about social psychology and influence. And I remember being Like this is so awesome. I want to do this. Like, this is what I want to do. and it was that intersection of how the brain works and how humans work in group. Mixed with persuasiveness and business that I thought was like, so cool. And I remember just like, you know, it was one of those like eyes light up moment as a student. And I think it's pretty cool, like roundabout way but I kind of in some ways, get to do some of that now. And you know, psychology is really, really connected to marketing and a lot of ways.

And I think you know, Rory Sutherland, he and his book Alchemy was one of my, probably my favourite books I read last year. But like, he is like the godfather of this too. It's like another one of these guys who just really applies things from behavioral economics and psychology and applies it to great examples in branding and in policy. [00:13:00] And really shows you how things like, you know, the Coke example, it's the same economic output, but people feel so differently about it. So it changes their behavior. I'm like fascinating. I nerd out on all that stuff all the time. It's so fun.

David Elikwu: Yeah, same. I think another great example was, and again, it's, it's just so incredible how, like you say, changing the framing completely changes how you think about something. So right now I don't pay for TV at all, just because I pay for all these streaming services. And I think what's the point of paying extra for TV on top of that, just because. By the time you pay for Netflix And Disney and Amazon prime video and all of those things there's enough to watch. I'm fine. But he was talking about how he convinced his dad to get sky sports, like the equivalent of ESPN here. And essentially it was quite expensive, but then he was like, oh but how much do you spend on a newspaper? You spend 20p on a newspaper, actually sky sports, even though it's however much for the month, it's actually 67p a day. And you know, the equivalent value that you get from being able to watch this compared to how much you spend on newspapers, it's actually [00:14:00] very economical, and so It's a really weird framing thing because in my mind, if you told me the top level price, I'd be like, whoa, that's way too expensive. I don't need to spend that. But actually when you break it down like that, and even when I think about all the other things, I probably spend 67p a day on, but just in my day-to-day life is less than a coffee, it's less than almost anything else you can buy. If the marginal value you get from it is more than that, then suddenly it's a great idea.

Arielle Jackson: It's a great way to take things that seem expensive and make a reference point to something you already do. And there's some nice examples in marketing too. Like that example that Rory Sutherland, I think he, that was in his book too. And he was trying to get his dad was in a retirement home or something. Right. And he was like trying to get him stuff to do.

Yeah. Anyway, there another example just as like a high price point item that does that framing to like a daily cost. Is this Snoo, do you know about this Snoo it's like this it's basically like a tech enabled cradle for babies. So, it's a smart cradle, think about it like that, like a bassinet. And you put your newborn in it and it rocks [00:15:00] and it shushes the baby and it's based on this pediatrician, his name's Dr. Harvey Karp. And he came up with this book, The happiest baby on the block. and there's these five S's. and it's like, what you do when you have a newborn who's like inconsolable, it's shushing sucking, sideline, whatever. There's like five of them. Okay. And he invented this cradle that does this for you. And it's like connected to an app it's very expensive. It's like $1,500 or something for this cradle. And usually you can buy a little bassinet for, I don't know, a hundred bucks, something like that. Like it's like 10 X or more than a regular cradle, but they've done a lot of analysis on it and like actually published in scientific pediatric journals and showed that it actually increases.

His goal has like purpose for the company is to increase baby's health through better sleep. And then to also increase family's health because there'll be less, his theory is like less postpartum depression and all of that if mom's actually slept more too. And so, when the cradle first came out, they were talking about it as $5 a day because you could rent it. So I rented one for my second kid. I never [00:16:00] bought my, it wasn't around for my first kid. And he said for less than the price of a latte per day, you can get, I think it was like two hours more of sleep. I was like, oh, okay, well now it's worth it. but like at $1,500 compared to the bassinet, that's a hundred, $150. That seemed nuts to me. Like I would never spend 10 X for a cradle, but I spend $5 on a latte and yes, I would pay that for two hours more sleep per day.

David Elikwu: That's incredible framing. And it's so right. So a friend of mine had twins not too long ago. Well, actually, oh my gosh, it's coming up to a year, but anyway, not too long ago, a friend of mine had twins and I am a godfather to them. And I remember the early months when you're spending time with them and trying to help.

It's a lot of work. And just thinking about what you just said. Suddenly that sounds like crazy value, even though like you say.

Arielle Jackson: Yeah, my sister-in-law had a baby,

Yeah. literally a few less than a month ago. And she's calling saying maybe he's not sleeping. What am I doing wrong? I'm like, well, it's really normal, but you could consider this Snoo and she's like, but it's so expensive. Well, you can rent it. And she [00:17:00] gets the $5 lattes too.

And when kind of, I I'm using that line now, you know, it's good marketing. When you kind of the people who endorse the product are actually saying that, you know, that's really well-framed. So when I explained it to her like that, she's like okay, I'll try it. I'll try it. I can always return it if it doesn't work, you know?

But yeah, in those early days you'll spend whatever you want, whatever. You could get someone to spend whatever, especially with twins. Right.

David Elikwu: Yeah, exactly.

Arielle Jackson: Sorry. I cut you off though. Go ahead.

David Elikwu: No, no, no, no, it's fine. I was going to say it's incredible how certain brands managed to integrate themselves into our lives. So I know that one, in some ways am deeply ashamed of, and in some ways I don't care and I'm also very proud is Superhuman. And I think this a great example because I think they did some work with you. I am just so unapologetically. I love Superhuman and I will convince people to get it. And I, I get nothing out of it. I'll talk about it all the time, just because it's so good and it works and the best and worst thing about it is it's so hard to explain to someone, you know, I sound like I'm convincing people to join a cult, but [00:18:00] to the uninitiated, it's so hard to explain and to quantify the value that you get. All I can say is that it's fast. And I know that's what they want me to say. Cause that's all they message, but it's true, it's really fundamentally true and I don't have metrics to back it up. I don't have anything else, but the product experience that you have, that this is just faster and easier and better, and everyone should be doing it that way.

Arielle Jackson: Yeah, Superhuman's an interesting one. Actually at, at first round recently, I don't even know if I think we can probably say this. First Round led their seed round. And I worked with Rahul really early on, on some of that messaging. And anyway, I'm not a convert yet, but recently FIrst Round sent an email, that's like, we're rolling out Superhuman for all of our employees.

And like, we encourage you to get it but I'm still so loyal to Gmail for having worked on Gmail many, many, many years ago. So it's funny like, I know people love Superhuman and I totally see the value in it. And you know, I guess maybe someday I'll make the switch, but I'm going to be one of those late adopters. Cause I'm still [00:19:00] like into Gmail. It's just like, seems second nature to me at this point.

David Elikwu: Yeah. I mean, I guess if you've worked on it and spend so long, you probably know a bunch of the g-mail secrets that the rest us don't. But I genuinely think that, part of, it was the, it's a paradigm shift of how I had previously thought about email. So I still remember I had over 19,000 emails at the time that I signed up for Superhuman and I wasn't necessarily looking for a new email.

A friend of mine had just got it and she referred me and she was like, oh, we'll try it if you want.

And what they do as you will know is that they book you in for a live session and someone is going to walk through the whole white glove experience of showing you the product. And even during it, I was like, yeah, you know, not necessarily buying it. I think it was just the paradigm shift of a bit like Apple in a way, forcing you to make decisions and forcing you to think of your thing the way they think of your thing. Because so I used to use Android. Now I use an Apple but I used to hate the constraints that Apple has, where they tell you, You can [00:20:00] only do things one way.

This is the only way to do it. This is the best do it. We don't care if you want to do something else, once you do it our way, you will understand it's the best way. And I hated it at first and now I get it at now. I trust that the fact that they say there's only one way they want to do it is because they have a high bar of quality for doing it that way, rather than giving you loads of choices and with varying levels of quality. And I with Superhuman compared to using a bunch of other emails, stuff that I've tried, they do one way really right and if you do it that way, then it works. Don't try and do any other thing. It's, it's not for that. It's for doing things in this way. You triage your email like this. And I just remember the feeling of in my head, I was saving email because what if I need it one day?

And I wasn't thinking of the fact that. there was over 19,000 of them. I was just thinking, Of hoarding and you know, what if I need this, what if I need to refer to this? And I do something like just the other day, I had to refer to An email from 2015, sometimes it's useful. but I think just sweeping everything under the carpet, I think going through that [00:21:00] onboarding experience, sorry, I don't want to turn this into like,

Arielle Jackson: Superhuman ad

David Elikwu: Yeah, but going through that, that, that experience, but I think it, goes to marketing in general and the way that you can frame a certain view of the world and get customers to buy into it.

I wrote about this as well, but I was thinking about Mike Maples Jr. Who is a VC and he's really awesome. And he has a podcast. And what he was talking about is the way that great founders are like time travelers and they bring people into the future and they are able to position this framing of a future world and bring you into it. They're not building something for right now and trying to iteratively convince you to change from what you're doing to something else.

Arielle Jackson: Yeah. it's interesting. Cause when, when Gmail first launched, one of the ideas was like everyone who worked at Google got a ton of email, right?

We sent a lot of email, we got a lot of email, both in our personal lives and our work lives and the belief of what the future would be like is in the future. Everyone's going to be like this. We're [00:22:00] just on the bleeding edge of it. And so the AOL or Hotmail or Yahoo account you have where you get like, you know, two or four, six megabytes, and you have to delete your messages in order to get more, wasn't going to work. That's just not the way the world was going.

And so. At Google, gmail was built as an email product for people who got a ton of mail and Superhuman was built for power g-mail users, right? Who were the people who got all the extensions and Rahul had built some of those extensions in the past. And I am, I'm one of those like power g-mail users, you know, keyboard shortcuts, and the undo send extensions and all, all of that stuff schedule emails for the future, all these bells and whistles that like, if you're a power g-mail user, you can kind of make Gmail work for you. but he said, what if we just rebuilt email for just the super-duper power users? And what would that look like

And so the idea that a lot of great founders do that you either take something that exists and there's a very top percent of the market like that, you're building for power users and you build a better [00:23:00] product that meets their needs. And sometimes you have to force them into doing things one way. Or you take something in that, it's hard that very few people are doing and you make it much more accessible and everyone can do it. So super humans, definitely an example of that, like, let's serve the power user, let's build something even better for them. We can charge for it. We can create this beautiful onboarding. We can make it super fast but really build a product for power users again, like the power users had shifted, you know, the power users in 2006, 2007 looked really different than the power users in 2022.

David Elikwu: Yeah, you're completely right. And I think the other part of the reason that I brought it up is because the pricing is ridiculous and somehow they make me do it anyway, because there's no other world in which I could imagine paying

Arielle Jackson: What is it? $30 a month or something?

David Elikwu: Yeah. $30 a month, which sounds crazy.

Arielle Jackson: But then if you frame it as like, if you had to hire a virtual assistant or an actual assistant $30 a month is actually like Super cheap.

David Elikwu: Yeah, So I know we skipped a [00:24:00] few steps. I'd love to let's go back.

You were mentioning with your career, for example, coming out of university, you had the guest lecture with Robert Cialdini.

Was that the first time you'd considered doing marketing or was that something that was already maybe a twinkle in your eye before then?

Arielle Jackson: I think I didn't really know that it existed to be honest. I was always kind of somebody who was interested in business as a kid. Like I was the kid with the lemonade stand and the garage sale. My parents had this giant box of change that I think they had inherited from one of their parents. Like it, was a huge cardboard box. Tons and tons and tons of coins. And they used to tell me that if I rolled the coins, I was like, you know, six years old. If I rolled the coins and took them to the bank, I could keep half the money. And I would, I would do that.

You know, I was always babysitting. I had a job, I got a work permit when I was 15. I worked at a clothing store on the weekends. Like I was always kind of industrious and I always like to work. I like to work and I like to make money. Like that was always something that I like to [00:25:00] do. But I never really thought of like, well, what does that mean for a career? So I think, I always thought like, well, I'm interested in science, I'm interested in psychology. Maybe I'll go be a clinical psychologist. I taught preschool for a little bit while I was in grad school. Kind of just like dabbled in a lot of things, but I never really thought of marketing as a career.

I guess when I was deciding if I wanted to do a PhD or not, I realized like that's seven years of research. Seven years of research on a really esoteric topic that like three people in the world care about when I was doing my masters and I was researching, it was researching The understanding and display of emotion and preschool children and cultural differences in it. It was an interesting topic, but like five people in the world cared and it took me a, year to publish like one thing, you know, and I didn't like how slow it was. That was sort of the it was like seven more years of this. I dunno, like fewer and fewer people are going to care.

And I wanted something that was moved faster. And so I got, I got two jobs, basically. This was 2002, I guess that would have been applying to jobs. [00:26:00] It was, it was not a good time to be looking for jobs. And I guess I was deciding between doing that PhD or working. And the two jobs I had was one was in a psych lab at Stanford, like as a research coordinator type person. Kind of continuing on what I was doing, but as a job, rather than as a student and the other one was like an entry-level thing at Google. And I literally couldn't decide what to do. It was a really hard choice and ended up taking the job at Google, just because of, that, that slow pace of research. And I was like, well, Google will move faster.

So that's kind of, I just started in like a really entry level job there and kind of fell into marketing. And I guess didn't look back or did look back it kind of all worked out in the end.

David Elikwu: That's really interesting. I'm interested to know what your parents did for work and maybe where your early sense of industriousness came from.

Arielle Jackson: Yeah. So my, my dad's a pediatrician, so he, he sees babies and kids and He's like, he's one of those people who like loves his job, He's been doing the same, he's in private practice. [00:27:00] So, I mean, he runs a small business. He has maybe like 15 people work there, something like that. But he's not very like business minded. He's kind of like, I like seeing my patients and he gets the joy out of it. He was made a good living, but he didn't like, you know, he wasn't really motivated by that. My mom is a therapist. She was the director of a preschool for kids with autism high functioning autism, for the most part. So she specialized in family therapy for kids who were intellectually normal or even gifted, but socially having issues that was kind of her thing. So our, a lot of our dinner table conversations were about like kids and health and families and all of that. Now I joke my parents are like professional grandparents.

So we moved back to LA when I was pregnant with my second son and when my husband and I go out, we leave my two little boys with a child therapist and a pediatrician. And we know they're in good hands. So yeah, they're really good grandparents. My mom is also not very like business [00:28:00] savvy or interested in, business. I mean, she now runs a little private practice. She does mostly zoom therapy. She retired from the job at the school.

I honestly don't know where it came from. I think maybe it was that my parents did instill in me like a good sense of, you know, you can be whatever you want to be. You can do whatever you want to do. You know, if you work hard enough kind of thing. And I never really like knew what I wanted to do, but I knew I could work hard. They also didn't like, give me everything I wanted, but they gave me enough that I felt supported that I could do what I wanted if that makes sense. So there's another thing that's really important to me as a mom. Like I had an allowance as a kid, but it was like pretty small. I don't remember what it was. Maybe like five bucks, something like that. Like, it wasn't enough to like, do everything I wanted, but it was enough that I could like go buy a soda with my friend or something. But they were always like, well, if you want more, you can get a job. Like we'll help you. We'll take you to the place and get you a work permit, you. know, that kind of stuff. So it was, it was like a good balance of always feeling like they had my back, but also like I could have my own back if I wanted more than what they provided [00:29:00] for me.

David Elikwu: Yeah, I think that's so important to have. And funnily enough, I think even for me, it's something that I probably underestimated that I got from, from my dad, which is probably ended up being one of the most valuable things is that, because I genuinely think, like you say that birth's a sense of industriousness where you are willing to go out and create things for yourself.

And I think even just believing that things are possible and believing that you can work hard and achieve things, and you can go out and do things whatever it is is such a critical thing that a lot of people just, unfortunately don't have.

Arielle Jackson: Yeah. Yeah. That's one of the things that going back to what we were first talking about about like entitlement and, you know, private school and going to an environment where kids are given everything by their parents. I remember like when I was 16, I wanted a car and a lot of my friend's parents were, you know, giving them a hand-me-down car or buying them, you know, a little car. And my parents were like, we're not doing. We're not going to buy you a car. Part of it was like, they probably couldn't, you know, and part of it was, they wanted me to work for my own car And I [00:30:00] ended up saving, I think it was $1,500 And I ended up buying like a 1983 Volvo, 240 DL that was belonged to my photography teacher in high school. She was getting a new car and like mentioned she had this old beater that she would sell to me for $1,500. So I saved up the money and bought it And I was so proud of that car. Like, it was such a big achievement to have buy your own car at 16. And it was, you know, it was a solid car. I've pretty much had a Volvo ever since.

David Elikwu: No, but that's a massive achievement, particularly if you're not getting like a, a massive allowance, you actually have to work for it. And from 15 as well, what were you doing for work at the time?

Arielle Jackson: My friend's mom owned a little clothing store and I worked Sundays at the clothing store. It was mostly like a kid's clothing store, just it a little like boutique and I babysat mostly, I think that was mostly it at that point. Yeah. 15, 16.

David Elikwu: Yeah. But again, I think some of those early working experiences. Again, I think it's one of those things we probably underestimate. They have such a massive impact on [00:31:00] just your ability to fit in with people, work with people. I think when you start working and I'm going to ask you in a second about your early days of Google, but I was just thinking about my early days in corporate law.

So I'd already been working for a little bit at this point, but now I'm in my quote unquote dream job working at one of the biggest law firms in the world. And it's all great. And then I remember like joining and I have been working for so many years to get to this point, even though age wise, we're probably similar with some other people, but I've just been working since I was like, yeah, like 15, 16. And there was another person in my cohort that actually, I think they joined six months after me, but technically it's the same cohort, but this was their first job. They'd just never worked before. And I just can't imagine never having to work, never having to do anything. You don't know how to interact with people in the workplace. You're figuring out everything for the first time.

On this kind of stage. I don't know if I could have coped with that, but I think having all of that experience just in being industrious, in trying things and learning things, getting some things wrong just helps in whatever context [00:32:00] it is, even if you're just, putting mail through people's letterboxes. I think it's all useful.

Arielle Jackson: Yeah, it's totally useful. And even to know, I mean, part of it was dealing with hard situations. Like I had a few hard situations even as a 15 year old in that clothing store. But like hard situations, how to navigate things independently. Even customer service, like facing different people who have different needs, who are mean to you sometimes I don't know, like I've worked as a hostess in a restaurant. That was another thing I did in high school. I worked as a barista in college. You know, getting those kinds of jobs early on, I asked my son, you know, what do you want to be when you grew up? And now just like every other eight year old, he wants to be a YouTuber, is what he calls it, like a YouTube content creator.

I'm like, oh gosh. Like he starts that at, you know, 15, 16, and doesn't ever have the like barista job or the, you know, restaurant job, I think they're going to miss some interpersonal world skills. But yeah, I think it's way easier to go into your first, you know, post university job having had five other jobs first, as opposed to just like going in cold.

David Elikwu: Yeah. [00:33:00] Those are genuinely the best jobs. I can't imagine. Yeah. If when I have kids. They have to do this jobs, just even if you do it for a summer, like any kind of serving job or a sales job. I remember doing so many of these random sales jobs where either you're like, whether it's for a charity or for a company like doing door to door staff doing, just raising money for charities in the streets, doing things indoors, all of that, like sales, and then this actually led to when I was working in advertising as well. I think all of that is working with people and dealing with the different facets of human personalities. And Like you say, sometimes people will be mean, sometimes they will act like they hate you for no reason. They've just met you. but then on the other hand, so I can give you an example of when I was in this really bad sales job, probably one of the worst jobs I've had. It was like really this slightly shady sales company where pretty much every day. So a working day was like seven to seven. You start at seven. And you're doing door to door sales, but you're selling a different [00:34:00] thing every day and you don't even know what you're going to be selling until you get to the office and then they tell you, okay, this is the thing for today.

I don't know if it's, if it's shady or anything, but I think the company was just very, you know, not always forthcoming with the details and stuff, but it's fine. like sometimes you're raising money for a charity. Sometimes you're selling something to people and they will also send you to a different area of the city every day. So you just have to, you know, so that's the reason you start at seven, so that by the time you get to where you're going, it's. nine. So, yeah, they just send you off to some part of the city. They give you the details about what you're raising money for today or what you're trying to sell today. And then you just have to go, you just have to go knock on people's doors.

You have to find a way to sell as much as possible. And it's all commission-based. And I also remember at the time I didn't have much money, because I think I was at university at this time, so I didn't have a lot of money, so I didn't want to be spending money on lunch. So my trick was to find someone that would invite me in to eat. And so that was, so that was like my north star metric. That was the ultimate goal.[00:35:00] And so I was, you know, obviously you're being nice to people you're, but you're also trying to like, oh, kind of, you know, do you wanna come in for some tea? Oh, of course. Why not? And then while you're there, then you also make the sale. That's the double whammy.

Arielle Jackson: That's like improv sales improv, right?

David Elikwu: Yeah, exactly. But I think it just teaches you great interpersonal skills it's the same with with serving or doing any, any service job.

Arielle Jackson: Well, some of it also is learning what you don't want to do. Like my son's doing this project, at school right now and he's learning about what it takes to open a restaurant. And one of the things they're teaching them is you have to write like a little paragraph about like, should you pay minimum wage or should you pay a fair wage?

And what is the, difference? And what if you're, you know, they're teaching them about like margin on there. He's opening a dessert restaurant and, you know, one of the dads in the class owns a restaurant and comes in and talk to them about stuff. And anyway, they're learning all the homework. Last night, he got sent home with a stack of papers to fill out, and the teacher had sent an email about this already.

And she said today we're sending [00:36:00] them home with their government paperwork. We're trying to teach them that some work is not fun and that work can be tedious sometimes, But you have to do it anyway. And the work was like they had made up government paperwork where you literally just had to fill in like your home address, your phone number, your school, address your school phone number on like 10 different forms.

Like manually by hand, just to show them, like on one, said like permit for work permit. One was like restaurant permit, you know, they hadn't named all of it, but it was literally just copying and pasting your address. And the last page was like did you enjoy the work? Did you find it challenging, like reflecting on the experience.

And it was funny cause like the, the luck that the lesson was supposed to be, some work is tedious and you have to do it anyway. It's not fun, but it's a cost of doing business and getting to do what you really want, which is to open this restaurant. And the question said like, did you enjoy the work? And he was like, yes. And I was like, oh gosh, well, I kind of lost the point of this, but, I like that they're teaching them that even at a young age.

David Elikwu: That's the greatest thing I've ever heard. I want to send my kids to [00:37:00] that school.

Arielle Jackson: I mean, that's part of the reason we moved back LA. I really did love going there and

David Elikwu: No, that was a very wise decision. I mean, aside from being in LA, that sounds incredible, but it also makes me think about, so, and again, it's something I wrote about quite recently, but, I can't remember the global point I was making, but I use some examples of studies and there's a really, really interesting one.

Actually, I think I stole this from Malcolm Gladwell, cause he talks about this and there's this study where they look at, this international math tests that kids do. So they kids take them around the world. And then they look at the data across these different countries. And in this one particular study, what they found is that you can tell how good a kid is going to be at maths without looking at any of their maths. They give you the questionnaire as they're giving out the paper, the questionnaire is not mandatory.

The questionnaire is boring and it's boring because it's long. It's not intentional. They're not, You know, they weren't actually trying to test anything with it. They are actually genuinely interested in getting data about these kids and what they [00:38:00] enjoy, blah, blah, blah. But it's this really long boring questionnaire. And they found there is a correlation between the kids that were willing to stick with the questionnaire long enough and actually fill it in. And the kids that were going to be good at maths, because that's all math is right. A lot of the time there's a single right answer. You just have to find it, and you have to be willing to stick with the problem long enough to get to the answer. And realistically, a lot of people particularly the way that other schools teach math is you're just optimizing for getting as many points in as quick, a time as possible, and so if you don't get it, okay, just give up, give up really quickly, go try something else. And I think in, in so many ways, so many paradigms, not just in maths, but I think that is a consistent message that a of people are taught. If something doesn't feel right, just quit, go do something else. It must not be for you.

And I think it's so interesting how ingraining that mindset of being able to stick with hard problems and working on something that's really difficult. It might be tedious. It might be boring, but learning to stick with problems just has these huge impacts in other areas of your life.

Arielle Jackson: Yeah, [00:39:00] it's like teaching grit and resiliency over actual math content and a lot of ways.

David Elikwu: So I'm interested to know what were your early days at Google like.

Arielle Jackson: Yeah. So I think I was part of the second. So I joined Google, actually, my first job, the one that I got, like I got into the company, I had it for three months. I was doing customer service for ad words. So I was literally answering the phone ad words was a brand new thing, which is now Google ads. And they were hiring like so many people straight out of university to go do these customer service jobs. It was a terrible job, but it was such a good learning experience. So, I mean, hilarious stories, like there was a guy who sold Pearl necklaces and he was advertising on Google and he was like an old guy and he was calling in, why is it so expensive to advertise on this term Pearl necklace?

And we would have to explain to him that they're was like porn term related to Pearl necklaces and that his actual pearl necklaces were competing with that, but do it in like a very informative and what they would say. Like Google-y proper way of explaining to this man who wasn't familiar [00:40:00] with this term, that it also meant something else and how he could, you know, put a negative keyword of like X, X, X, or sex or video or that kind of stuff. So that he wasn't competing with people who were looking for a different type of content.

So I did this job for three months. I realized like this taught me a lot of good skills, kind of similar to working in a restaurant, but it wasn't what I wanted to do a long term. And I had gotten that job because a friend of mine at school he had said, why don't you come work at Google, they're hiring for this and blah, blah, blah. And he was in that job and about two months into it, I was like, I'm not going to last at this. This is, you know, this is a good experience, but it's not really meeting what I wanted to do with my life. And I applied to transfer to this Google APMM program, which was the Associate Product Marketing Manager.

And I got it. It was a really competitive program at the time. I don't know if it still is, but it was like I didn't even know about it when I was applying to Google, but once I was there, I was like, that, looks fun. I want to do what those people are doing. And I applied to transfer and got it. So after three months I moved [00:41:00] into marketing, it was similar, like a super entry level marketing job.

It was really fun. I mean, it was like, I think there were 12 of us maybe in all of marketing and like a couple of senior people and everyone else was like 22, 23, a lot of recent college grads people had done teach for America. People had some of them had a master's degrees and other, other university studies or a couple of years of work experience, a lot of ex-consultants, but it was a good crew, just like other young smart people who didn't know anything about marketing yet, but we're excited to learn.

It was really fun and people say it's sort of a replacement for business school in a lot of ways. And I kind of felt like it was, it was learning on the job we had managers or mentors who were kind of more experienced marketers and we rotated around on products. So I worked on ad-words at first, which was, you know, the ad product. And then I worked on Google books for awhile. And then I moved over into Gmail and worked on a bunch of other things. But it was amazing.

I mean, Google in 2003, on a 12 person marketing team, when the whole company was 1400 people, it was such a cool [00:42:00] experience to like, you know what they say about joining a rocket ship? Like those friends you make in the trenches when things are really crazy, but really hard. Those are like lifetime friends. Kind of got to do it again at square, which was pretty cool too. Like joining a company like that. That's super intense, but doing really well if you also are good at your job, you just like grow on the rocket ship.

David Elikwu: I really want to get to square, but before that, just, okay. So at Google, you were there for almost years, eight years. How your experiences developed? You know, as you learn more, as you became more senior as Google grew, because again, like you say, 2003 is so different to where Google is now, all the companies that they've added, everything else that they do. Yes. I'm interested to know how that experience changed over time. And also what you learned during that period.

Arielle Jackson: Yeah. I mean, I learned so much and I think I stayed there for so long because every couple of years it was like a new company and a new. There were a lot of things about Google that I think they got right. That I assumed all companies got right. [00:43:00] Because it was my first experience working at a company like that. I'll give you an example. Like when, even before I got the job, as part of the interview process and the onboarding process, like you learned about the purpose of Google, you learned about this idea that Google's purpose is to organize the world's information and make it universally accessible and useful. Like everyone knew that and then in your onboarding they reinforced it. And then when you actually had a job, you had to understand how your job connected to that greater purpose. And I just assumed this was how companies ran like that, that made sense. And now having worked with hundreds of companies, I realized like most companies don't get that, right.

They don't have a purpose that everyone at the company knows and everyone understands how their individual layers into like their team functions job layers into that grander purpose. And it's so powerful to get people to root for you externally, but also get your employees to rally and to feel good about what they're doing and to understand how, it connects to something bigger than what they do every day. So I kind of assumed everybody did that right. Or did it like they did.

And in fact, that was pretty [00:44:00] unique and special. There's a lot of things about Google in those early days. I think hearing from the founders, you know, we, we all knew Larry and Sergei. They came and talked every Friday to us and, you know, we would go and present things to them and the way they made decisions and just even that kind of exposure to like a founder led company was really cool. I'm trying to think what else was great about it? Oh, the rotating aspect of that job for the first two years where you get to work on a different project or different product with different people, but you take what you learn and you move into the next thing. a lot of companies do that, especially in marketing and in brand management.

You know, Procter and Gamble, and General Mills and all those companies operate that way too. But I think that keeps young, smart, hungry people motivated whenever year or six months, you get a new problem and you were your problems kind of layer on each other. So the first time your people joke now, like when you're a product manager at Google, you're working on like a feature of a product of a feature in a country. Like it's very, very specific, but back then it would be like you're working on a new app [00:45:00] ad format. Okay, good. You did that. All right. Now you're going to go work on a new search thing. Okay, now you learn that Now you're going to go work on something totally new and different, which is we're trying to index all the world's books. Good luck. But they wouldn't have given you were trying to index all the world's books before you have had the first two experiences. So they kind of layered the challenges on one another. And then I think if you did a good job, you got a bigger, a bigger project the next time. And that, that type of learning environment where it's, like. Take something that you're given and you do a good job with what you're given and maybe you go outside of the scope of that job and people see that and then the next time you get a bigger project, and a bigger project, and then a team who's doing those projects. That was just, I thought normal. But in retrospect, I realized a really great first learning experience.

David Elikwu: Yeah, I think going back to the first thing that you mentioned is really interesting for me thinking about building culture and how it can be so easy to miss the mark with that. And I think part of the reason is because you have to get it right at the beginning. And a lot of people think they don't [00:46:00] have time for it at the beginning and they'd rather focus on you know, potentially building, building what they're building. Maybe they've got VC pressure. Maybe they've got market pressure. There's a sense of urgency. Every startup you're trying to grow as much as possible. And very often people can focus completely on what they're building and forget or neglect to also develop a rocket ship culture simultaneously.

And I think even at the startup that I'm at, so currently I'm in product strategy and operations, but prior to that, I was chief of staff and I was working directly with the president and it's so what the president of the business, but one of the things that I did have to look at one point was onboarding because we were planning to double in that year and we've pretty much doubled almost year on year, when I joined, we'd probably just gone through a massive hiring run So we just got into around a hundred people or so, and now we're just over 300 in the last two years. So I think we're like 350 or so. And it's so interesting.

First of all, how many revolutions we've gone through as a company, culture wise. And how much things change almost every [00:47:00] six months. It's like a new company in a way, just like you said, just because the way that we report changes, the way that we do this changes, but I think the constant has been, and I think our founders had been really good with this, having a strong set of values and actually our values have changed once during that time, but we've been led by those values and they tried to bring them up and they try to introduce them.

And I think I can easily see how, if we didn't have such a strong focus on that, like when I had to work out onboarding and how we did that and how do we get people on board, if you don't do that stuff at the beginning. In just a short time span of two years, suddenly you're a 350 person company. You can't do it now. I think there's so many things that would take so much more work to fix now, if you didn't get it right before.

Arielle Jackson: Yeah, that was Problems compound. It's kinda like, it's the people always ask like, oh, should I rebrand? Should I change my name? Like, you know, I'm thinking about it. It's like this, isn't going to get easier. Let me tell you that the sooner you do this, the better, because if you feel like you need to do it now, like give yourself another year and another, you know, millions of dollars in brand equity [00:48:00] that you've built and 200 more people, and it's only going to be harder, not easier. And the same is true with all that purpose and culture, and work as well. I think Google did a great job of that. I mean, they had that list of, I think they've changed it now, but like I remember one was like, don't be evil and we can be serious without a suit. And there were all these values that I mean, they really lived it and I don't think it was manufactured at all at least in those early days.

Yeah. Back to your question of like staying for eight years. And I thought of a couple of other things that made it interesting besides obviously the growth, the rotation, all of that. I never studied abroad in college. I was always working and I had a job and I, I finished college in three years while working. I figured out that like, if you TA'd college courses while you were in grad school, they paid a lot of your tuition. So I started doing that. So anyway, I never got to go abroad or never prioritized it. And one of the things I realized that like, I kind of always regretted that, like I never had that experience. My sister did it and it seemed really fun and cool. And she like speaks fluent Spanish now. And I kinda always regretted not doing that. and then I realized like I work for an [00:49:00] international company that would send me anywhere I wanted to go. And in fact they said at one point, like, where do you want to go? You could go somewhere and like, do this, do your job in another office. And so I started thinking like, what are the things that I can do here that I wouldn't be able to do if I had joined a smaller company that didn't have that footprint. And I spent some time in Tokyo working on consumer products out of Japan. And like, that was my study abroad. You know, that was my, I didn't get to study abroad when I was 20. So when I was 30, I got through work, which was super cool. So that was another thing that kept me on a little bit longer. And then I also joined what at the time Google had this thing called Autonomous units.

They were kind of like, people always say, it's not a real startup cause you had her backed by Google, but it was the feeling of a more risky adventure where whoever was the lead of it. It was often a product manager acted kind of like a, mini CEO. So you kind of got to experience like, what is it like to work on? In my case, it was a, I think a seven person team. There was an engineering leader and a product leader who I had worked with previously on other [00:50:00] products who kind of built what was now called Google surveys, which is like their research product. So I went and did that. That was like my last hurrah. And I feel like this is fun working on a seven person team. And you know, it felt really different from the big company that Google, had become. Even though we still had to do a lot of the bureaucratic things at the same time.

David Elikwu: Is that part of what made you want to leave and join square?

Arielle Jackson: Yeah, So two things that made me want to leave. One was, the learning had definitely plateaued like the learning for the first two years, it was literally like drinking from a fire hose. Like it was insane and so fun and so fast and so amazing. And then I got to be a manager of a team, and I really loved like the people who worked for me and with me and the dynamics of mentorship was really awesome. And so that was like another, you know, exponential learning curve that I was on. And then it got to be a point where it's like, well, what else can I learn here? And there was the, let me go to Tokyo and see what it's like to live this like ex-pat life for a little while. That was awesome also crazy learning in a [00:51:00] very different direction, but also learning. And then it got to the point where like, okay, I'm 30, I'm about to get married. I probably want to have kids at some point. I need to go do something And challenge myself again. Like I could see myself and some of my friends who still are at Google, like 25 years later, when the 20 years later they're still there.

And I had this feeling of like, I don't know, it was about turning 30. And it was like, if I stay here until I'm 30 and don't go do something else, I'm going to be here when I'm 40 and 50, and like, I just need to leave. I need to go do something else. At some point, staying at the same company becomes a liability. It's like when I see my friends who are still at school, I'm like, really, you're still there, it's been 22 years. And I kind of question it, you know, you're the golden handcuffs in a lot of ways it's being risk averse in a lot of ways. I know I knew how to operate at Google. I was very effective there. Did I know how to operate anywhere else? Could I take what I learned there and have be back on that exponential growth curve rather than what had become a plateau. And that was sort of one of the. Impetuses [00:52:00] for change. And then one was like, I know I want to have a family at some point. And I need like one last, really hard, crazy experience before I want to have kids. Cause I don't think I want to have that you know, I don't know that I'll have it in me to have that crazy hard experience again. So that was sort of the, that was the impetus.

I also, I made jewelry that was like always a hobby of mine. I made jewelry and I used to sell my jewelry at a bunch of galleries like around San Francisco and LA. And I did a few like holiday craft fairs and I had a friend who worked at square, who had given me a square reader, was like, take this to your craft fair. And you know, you can sell more if you take credit cards. So I took this square reader to this craft fair and it was great. Like I did sell more than I normally did. And afterwards I sent him an email and I was like, Oh, hey, that was really cool, I did sell more. The reader worked great like, cool company. He was like, come and interview with us. That was the sort of other how I, how I got there. I think being the small micro merchant and having that experience almost as the user and then realizing how great it was and [00:53:00] then being like, all right, I'm going to go talk to them. So I took that meeting and then I ended up working there.

David Elikwu: That's awesome, I think I'm going to have a question about that, but I want to take a step back to what you were just saying. I think what you were just saying as well was so interesting in your time at Google, about when you do stay in a certain role for too long, it can become a detriment in a way. And I think because the key is being able to test, I think it can become very easy to think within a limited space.

And you get this sense of competence because you are just applying yourself to the same set of problems, right? The problems might change in kind of flavor and texture, but really it's the same thing and you're kind of doing the same thing. And that's actually how I felt, I spent about five years in corporate law at one firm.

And you feel so competent and I love that feeling and I miss that feeling because I don't think you really get that in startups general, but definitely not currently in my role and at, the stage of business that we're at you definitely don't have that same level of, you know, I am a subject matter expert. Maybe [00:54:00] I'm still very far from that. but also in a company that you've been there for a long time because you know, the people, you know, the, the content and it's, you know, how the business works and you know how to get around, you know, how to do things. And So you can become very competent. You become the old hand and you, and you can do things. And I think it's really important to test yourself and be able to see how well you can apply the patterns that you've learned in new contexts and see how well you can, you can match those things and see how versatile your learnings really are, because it could be that actually.

And I, I do feel this actually, when I look back and I see a lot of people, that are still doing that, not that there's anything wrong with doing it, but there are so many things I would not have learned if I hadn't left. As much as you think you know about business, because you work with businesses, you work with some of the biggest companies in the world. It's absolutely not the same as being in the business and working on the business and particularly scaling it from, from a very small level. I think you learn things from completely different paradigms in completely different ways and, and a very different speed. So I think, you know, I'm [00:55:00] sure you probably experienced this joining Square at quite a young stage as well, that it completely shifts the way that you might have to think about working on a business and scaling a business.

I know that you, you know, you joined Google relatively early as well, but I think there's still a big difference there where one becomes almost like its own ecosystem and square at the time, I'm sure was still finding their feet and figuring things out and developing their, their messaging and their positioning and what their best foot forward was.

Arielle Jackson: Yeah, I mean, it was 10 times smaller than Google was when I joined. So Google was 1400 people. I think I was employee 140 at Square. So it was still big, I mean, compared to the companies I work with now, and the next company I went to, that was, again, seven people was like 140 is big. I think they were a series C company at the time they had a successful product. But they weren't like they hadn't made it yet. It was still a little bit risky. They had no marketing department, they had like two marketers, I think who were there. They didn't have like a function for marketing. They had the friend who gave me the card reader. [00:56:00] He was the first marketer at square. And then they had hired this woman who I'm still friends with today, from Netflix who did performance marketing, paid marketing. She's really great at Direct mail and some of the channels that Netflix grew in and she brought those to square. So she was sort of my peer in the performance area. And then they hired me to run more programs. Do things like retail distribution, and really bring kind of like a product marketing lens to the way that they were growing. They knew they were going to expand into multiple products. So they didn't even have product managers either. Actually they had like engineers and then had business people and so I was on the business team. At 140 people that's pretty crazy.

David Elikwu: Yeah, that's super interesting. I'm also, really curious about the fact that I'm noticing your trajectory of companies is going down in terms of the size of number of people. I'm wondering if there was any thought or intentionality behind that. Like you start at Google, you go to Square, which is at, at that time series C [00:57:00] and then you go to an even smaller startup which eventually gets acquired. So I guess it's kind of a, a U shape, but yeah, I'm interested in that.

Arielle Jackson: Yeah. I think the impact that you can have as an individual is greater when the company is smaller. Now there's some amount of like, okay, well, if it's a big company and you're in an executive role and you're kind of running a function or a team, you can have a huge impact. Yes. But it's really your team having the impact, not you as an individual.

Google was great as I said, like, I had an awesome experience there. I learned so much, both like what good looks like and sort of the anti examples in some regards too, but mostly what good looks like and the people were amazing. But by the time I left, I sort of feel like, okay. I'm like one of, you know, I don't remember how people was tens of thousands at that point, probably.

And like, if I quit tomorrow, is anyone going to care? You know, that started to feel a little bit like a cog in the wheel. I didn't like that feeling. And so the square thing really was like, let me go somewhere smaller where it can have a [00:58:00] bigger impact. That was awesome, it was crazy. I mean, working at Square that you're probably living this right. It's like the hundred to 800 people is the craziest time. I think, at a company it's that like growth insanity stage where you're doubling every year and you have to like rethink how you do things all the time. But it was awesome. Like I learned so much, I'm still friends with the people. There was another one of those like crazy career formative, you know, you make such good friends.

You've lived through these hard times together. It's almost like, I don't know, like, going to reward together or whatever. Like it's so bonding for the people who are in it together. yeah. And so then actually I was the first person to be pregnant at square, and there weren't a lot of women there.

Actually, it was like, we would always joke like that woman I mentioned who worked at Netflix, her name's Heather, she's still a friend of mine. we would joke, like there would be never a line for the women's bathroom, but there was sometimes a line for the men's bathroom. And that like never happens like in a movie theater or concert or whatever, because there just weren't that many women there.

And Jack really changed that a lot. [00:59:00] Like he hired a lot of female executives. That company is like run by a lot of women now, I think he's done a phenomenal job changing that. But when we were there, there weren't that many women, there were a lot of young people. I think the average age was probably like 25.

And I don't know how old was I 32 or something and I was pregnant and I was scared to tell them I was pregnant because it was a very intense work culture. So I waited until I was like five months pregnant. Couldn't hide it anymore and told them. I worked until I was 39 and a half weeks pregnant, like a hundred hours a week.

And I realized like, this is not gonna work after the baby's on the other side. Right. Like this is not going to, I don't know what I going to do. And that was sort of the impetus for the next change. And the next change was during my maternity leave. I started helping my husband's startup. So he had started a company with, he had worked at Google as well.

So another guy from Google and him started this Android company and I was on maternity leave and helping them, you know, unofficially. And [01:00:00] then I was like, gosh, I have to go back to work. You know, I like this job, but I don't want to work a hundred hours a week with this like tiny baby, and ultimately decided to leave Square and to join that startup.

And I negotiated with them that I would help them three days a week. And three days a week was more than I had been doing on my unofficial maternity leave helping them. So they were psyched histerically like oh three days, it's going to be awesome. And I was psyched cause it was so much less than a hundred hours a week or 80 hours a week or whatever I had done before.

And so that was kind of how I ended up joining that next company. It was, my husband was the, founder, one of the founders and this guy Ed was the other founder I'd worked with before. And it was seven people. And I worked there three days a week and did all the marketing and comms and we launched and got to 2 million users in a matter of months because we really tapped into this really interesting ethos around.

And you said you were an Android user at one point. Android users this was 2013, 2014. Sorry. They felt like second class citizens in a lot of ways. Cool apps would come out, iOS first or iOS [01:01:00] only, and then you'd have to wait like six months or a year never to get it on android.

And so we tapped into this idea of like, well, what if something could only be done on Android? And we came out with this app, it was called Cover, surface the right apps for you at the right time on your home screen. Because on Android at the time, you could actually change the home and lock screens and modify them, whereas you couldn't do that on iOS. So, we kind of very much, endeared ourselves to the Android community and had a ton of organic growth and it was a fun and fast and furious time, three days a week. Uh, so that was the startup. And then they were acquired by Twitter.

And I realized, well, I just left Square. And I don't know if I want to go back to Twitter. And I got this really great offer to go lead consumer product marketing there. And I said, you know what? I think I kinda try doing this thing where I help little startups. I'm going to keep working three days a week. And I like this little startup thing. So emailed a bunch of friends who were founders and just said, Hey, I'm not going to go to Twitter with the rest of the team. I think I'm just gonna like, help little startups.

Do any of you need help?

And every single one [01:02:00] said yes. Yes. Yes. So that was how I ended up becoming this like marketing expert in residence type person for tiny startups.

David Elikwu: That's awesome. That's a great story. And also you highlighted some of the gaps in questions I was actually going to ask because I think I did hear, you in preparing for this podcast, I was listening to you talking on another podcast and you mentioned not wanting to go back to Twitter cause you'd worked at one of Jack's companies before. And, no one asked you any more about that. And I was like, I really want to know more. So I think now that you've explained the whole story, it makes complete sense, it's very clear. And I think, I appreciate that in some ways I think we have made a lot of strides with making work places open to everyone, but at the same time, I, I really think that we haven't in some, in some ways.

And I appreciate what you're saying in terms of how things have turned around dramatically and how there's been a huge improvement, I am starting to see for myself very often. So, you know, [01:03:00] we had something similar where, you know, you have some people that go on maternity leave, for the first time and suddenly you have to create policies cause no one's ever done it before you have no, one's actually thought about what does this look like?

Okay. Now we have to figure out what is, what does, what happens on maternity leave? But also then you see the interesting thing where particularly, like you said, being at this rocket ship stage. If someone goes out for even a few months and comes back, the org that they were in is actually now completely different.

And you have to figure out how do you actually make sure that this person fits back into not necessarily because you've replaced them. I think it's very different from, in a larger company where you're doing a like for like, oh, have someone in as maternity leave cover. It's not even that, it's the entire nature of the problem has changed.

The entire function may have been reorganized in some ways, because we're from a product perspective, we're trying to change our alignment to work more on this. We've created different roles. There's this person. So now you need a new job title [01:04:00] because your old job title isn't even necessarily the same thing. We Have these other job titles and yeah, I think it does a really interesting problem there. And I actually see that, not just where around, but in general, I think it's, it's quite a prevalent problem in a lot of startups.

Arielle Jackson: For sure. I mean, on the first point about maternity leave, one thing I will say about Jack is he was amazing about this is, when I told the company I was pregnant, I said, what's the maternity leave policy. And the HR person was like, it's whatever the state of California requires. And I looked up what that was, and it was like six weeks of like partial pay and maybe 12 weeks of job protection.

It was like, no vesting, no salary. No, it was like pretty minimal. And I told them if that's, I'm just going to leave, if that's the policy, like that's, I'm not taking six weeks off. Like I know what it's like to have a baby, like some of my friends have had it. I had one. and the, the HR person was like, well, we'll look into it. You know, we'll see what we can do.

And that wasn't really good enough for me. [01:05:00] So instead I had a lot of friends who worked at what I would say are like the comparable startups to Square at the time. So it was like Airbnb and Dropbox and Twitter. And there were like a bunch of companies that now are, you know, big companies, but at the time were kind of maybe that like growth stage startup.

And I figured out what all of them were offering. And then I figured out what sort of the more established companies like Google and Facebook were offering, as far as maternity leave. I created this Google sheet that was like company policy. Like, does it include vesting? How many months off? Is it for both parents? Is it for non birthing parents? You know, all, all these rules. And I made this spreadsheet and I gave it back to the HR person. And I said, they did all the research for you. Like, this is what, you know, here are the comps. And like, I think we should do something like this. And it was, it was a recommendation and she was like, oh, okay, thanks.

Yeah. We'll take this to Jack and get back to you. And again, I was like, oh, okay. Like, I'm just going to take this to Jack. So I asked Jack to meet and showed him that spreadsheet and he made the policy even better than the one I recommended. He changed Square's [01:06:00] policy. I think it was to like three months full pay, full vesting, for any parent, whether you were birthing parent or not.

So that was pretty cool.

David Elikwu: Okay. So I'll try and keep this short. Don't worry. We'll wrap up soon. I'm really interested to know how you're finding the experience. First of all, How did you end up at First round? And then also, how have you found maybe the difference between working on the venture side compared to working within a startup within one startup?

Arielle Jackson: Sure. So everything, in retrospect, it all seems so clear, but it's all kind of random, right? So, um, I told you, like I was helping my husband with his company while I was on maternity leave and ended up joining there. So First round actually been the lead investor in their seed round. And Josh Koppelman who started First round was the board member.

And he's been a mentor of my husband's really since then. So, after we were acquired by Twitter and I had emailed the friends and said, Hey, who needs marketing help? And everyone said, yes. And I ended up working with a couple of old friends who were Google product managers, who now are the founders of an ed tech [01:07:00] company called Seesaw.

I helped them name it and position that company. I was like my first gig. But first round had sent an email to my husband saying, Hey, who did you use for marketing and comms? You guys had such a great launch. We're you know, we want to build up our referral base and he's like, oh yeah, my wife worked there part-time and they were like, can we meet with her?

And so I met Brett Berson who was one of the partners at first round. He started first round platform team, which is the services that we provide to founders to help them with the first 18 months of company building. And at the time the team was basically just Brett. This was 2014 or so and, um, I had lunch with Brett and just told him what I did at Cover, which was the Android company and what I was doing now, which was consulting with some old friends.

And he goes, well, will you do a project with us? And I was like, okay, what do you have in mind? And he's, he didn't really know. He's like, how about, because I had been spending a day a week helping other startups. I was just like, I didn't know what I was doing. So I was just like, buy out my time to pay me for a day a week and I'll come help you with [01:08:00] whatever you need.

That was how I got started. Like, I didn't know what, I didn't know what to do or how to package my services. they didn't really know what founders needed either. Like I had, two that I had helped so far. And so Brett said, well, why don't you just come help us a day a week and we'll offer your services to our founders and you can help them and we'll do it for three months and see how it goes.

And so eight years later I'm still working there. So that was how we started. It was a three month project for one day a week.

David Elikwu: I I'm really fascinated by this kind of brings us back full circle to a previous conversation that we had earlier about the future of work and the potential of both one is people working at home, working from home. You've been working from home for a while. Prior to the pandemic. But then also this idea of fractional work and then mixing into that, then this may be creator economy space, and, you know, you are selling your, your jewelry.

And then there's lots of people that have side hustles and other things they want to do. What do you think that space looks like in the future between [01:09:00] work and also your experience with venture and, and how you see founders building things. And then also like the creative side that you have some experience with as well.

Arielle Jackson: Yeah. I mean, it does seem that COVID accelerated this for a lot of people and a lot of companies, it was already happening. Like, I, I worked in San Francisco for first round. I would be in their office most of the time when I was working with their founders. And then they started investing in companies that were like in Burlingame or Los Altos or Palo Alto or Oakland.

And it was, it's a big drive to go from like Oakland to San Francisco at like 3:00 PM on a Tuesday could take you an hour. So instead we would start video chatting, like I'd be in the first round office and the founder would be in their office in Oakland or San Mateo or whatever. And then I got to this point where.

I don't need to come in to the office to video chat. So I'm just going to work at home. And then if I'm having an in-person meeting, I'll go into the office and have the in-person meeting. But if I'm on video chat, I don't need to be in the office. And first [01:10:00] round was fine with that. So I did that and I would, you know, sometimes be in the office and sometimes not.

And then, I was pregnant with our second son and, and realized like I can't do this without those professional grandparents around and my husband had left his job and was kind of between things and we decided to move to LA and I told first round, we're both from LA. We'd been in San Francisco almost 18 years.

I told first, Sean, we're going to move to LA. I totally get it if you don't want me to work here anymore. But if you do, I'd be happy to come up once in a while and like do these in-person meetings. But honestly, like a lot of these founders are in New York or LA or all over at this point. I don't need to be here.

They were like, yeah, yeah. I'm just moved to LA and you'll fly up once a month and do a day in person. And then COVID happened and I stopped flying up once a month to do the day in person and it became normal to be remote. So, I think that accelerated, like they shut down the office, just like so many people and everyone was remote and I was pretty used to it at that point.

Like I have my little, you know, home office slash guest room that I work out of. [01:11:00] And, it worked pretty well. I think it's become more normal. And the idea of like fractional work or, doing a lot of different things has also become more normal. I see a lot of startups that are trying to offer services to hire fractional employees or contractors, in skilled professional areas.

Startups have always relied on agencies for things, And outsource dev shop to help accelerate some of the work that they don't want to do internally, creative agencies, video production agencies, content PR. There's always been a lot of things that startups don't need full-time resources for.

And so they end up outsourcing to various levels of freelancer agency. And I think the distinction between employee and like freelancer agency, it's not as black and white. There's a lot of gray now. So my relationship with first round, I'm an employee of first round, but I'm a half-time employee. And that allows me to do things that I want to do outside and still like pick up my kids at school a few days a week.

And so I worked there half time. That's my number [01:12:00] one priority has always helping First Round founders. And I work with eight first round companies at a time. That's kind of what I'm able to do in about half the time. And then I do some consulting on the side, oftentimes with later stage or growth stage companies, usually something pretty different from what I'm doing at first round.

And then I started teaching a Maven course. Like you also, that was mostly because I had helped Maven with their positioning and naming and worked with Goggin and West. And they were like, you should teach a course on this. And then I started doing that too. I don't make jewelry as much anymore, but I still, uh, I'm a pretty involved mom and, you know, I still, like I said, pick up my kids at school, make dinner, all that stuff that I probably couldn't do if I was working a hundred hours a week.

David Elikwu: Yeah, that makes a little sense. Probably one of the last questions I want to ask. You in particular is also your thoughts on the idea of maybe personal branding. I think it's something that comes up a lot. People talk about it a lot now, and it definitely fits in with this idea of, you know, wanting to essentially own your career in some ways.

And [01:13:00] what we were just talking about with fractional work and people that want to do lots of different things. And I find it interesting. Part of the reason I wanted to ask is because earlier this week I was listening to, Okay. So it was one person that it came up and he reminded me of some books I'd read earlier.

So I think it's Chris Lochhead, who is the Category Pirates guy. And, okay. So what it was linked to is I think I heard you talk about maybe in one of your, something that you'd written up, that you don't necessarily always need to own a category. And then I was listening to Chris Lochhead separately and he is all about owning the category, you have to own the category. But. He was asked a question about, personal brand and building a category around your personal brand. And he was so angry about the idea. He was like, oh my gosh, he just really hated the idea of, you know, people having personal brands or whatever but I found that so interesting as a paradigm, opposed to, for example, maybe like Reid Hoffman who talks about like The startup of you and that's one of his books and the other one is The Alliance, and he very much thinks about from LinkedIn's perspective of people thinking of their career, like a startup and being able to [01:14:00] build their career and having a very proactive approach to building it.

I'm interested in. Considering your trajectory, where you've kind of built your own, you know, a name for yourself where you are recognised in your field and people know you for this and companies will come to you for this. And you're widely regarded for that. I'm interested to know your thoughts on like where you fall on that spectrum between, should you just be focused on just doing your work and naturally building a reputation or should you be like proactively shaping and crafting your career?

Arielle Jackson: So I think early on in your career, you just have to try a lot of things and take a lot of swings and like go do a great job. Somebody asked recently, like, what do you, what should you do in the first 90 days of a new job? I'm like, do everything you said you were going to do. And then take a couple swings outside of that.

Cause like that, and just sort of separate from personal brand. But like you asked me about career trajectory and then you also asked me about personal brand. So personal to career directory, do what you say you're going to do, and then do even better than that. And [01:15:00] you'll just keep getting new opportunities.

If you put yourself in the right companies, in the right roles, if you do that and you're not seeing growth, you're not in the right place. So that's sort of my take on like career. and when you feel that the growth has plateaued, it's time for either a new role at the same company or a new company with a new role or the same role at a new company.

So, if you're growth oriented, there are times in your life where being growth oriented is right. And there are times in your life where maybe you, I personally don't care that much about like career growth right now. I'm at a place where I'm pretty happy with what I'm doing. I can keep doing this for a while.

The things that are interesting about it are the variety of companies I get to work with the context shifting. I know a little bit about a lot of things now, because I've got to work on so many different industries in so many different people. And the Psychology of all these founders is super interesting to me. Like some of these sessions ended up being like mini therapy sessions. You know, I've had a few founders cry in the meetings. Like we're getting to the heart of the story of their company and we have these like very personal connections. So [01:16:00] that's kind of what drives me right now.

So understanding like, is this a time for growth? Or is this a time for like being satisfied with what I'm doing? And I'm not like on this growth ladder. On the personal brand front, I haven't really like invested, I haven't thought about or invested in like a personal brand. There was one time that I did think about it, which is I was thinking about whether or not for my consulting company to operate as Arielle Jackson or to come up with a name.

One of the services I offer is naming. So I thought I should probably come up with a name and like, I should, you know, have a great name for my business to show that I can come up with great names. And then I realized, like I had so much equity within like my personal name that actually creating a new name for the business would hurt it, kind of like that rebranding thing we were talking about.

So I decided not to, and just operate as, as my personal name. That was the one time that I thought about like personal brand, company brand, all of that. I'm not a big, like, I don't have like, three followers on Twitter. And like, I don't really like check LinkedIn all that much, I'll check it and like, look at what people write to me, [01:17:00] but I'm not like super into those platforms in a very active way.

I think personal branding for me is more about the reputation for all the founders that I work with directly and them telling their friends and almost all of my external business is referral-based and the personal brand among that audience of like, Are you an early stage startup founder who needs help telling your story and like getting your marketing and your messaging tight, you should go talk to Arielle.

Like that's the brand that I want among the audience. I'm not like famous in any way, but among early stage startup founders, I have a reputation. Like that's good enough for me.

David Elikwu: Awesome. I think you're very right in that. I think you build your reputation by the work that you do, and if you do good work, people will know you for the quality of that work. And I think sometimes on one hand, I definitely I'm a proponent of, you know, people putting themselves out there and creating a name for themselves.

Simultaneously, sometimes people over-optimised for that and they over-optimised for having this brand. I think it's very much akin to, I see [01:18:00] a lot on Twitter, for example. Loads of people talking about like getting into tech, getting into tech, getting into tech, which is great, but I see less people maybe talking about like getting good and how to actually be going to your job, not just getting the job, but being good and staying there because that is the part that a lot of people then struggle with.

That's like the next issue that people have. And I don't think focus on enough on how to get good and how to improve and how to scale up the rest of your career. More than just like getting a foot in the door and getting your name out there. And some of those other, maybe soft touch things.

Arielle Jackson: Yeah. The worst thing about marketing is kind of the emperor's new clothes effect. Emperor's new clothes effect that you have where you see all the branding or the marketing around a certain company and you purchase that product and then you try it and you're like, it's okay. Like the products are right.

But like the marketing was really better than the product. And, I think some personal branding kind of falls into [01:19:00] that camp where you see these people with like giant followers on Twitter or who really talk a good game, or they've written the book on X and then you're like read the book and you're like, Ugh, it was okay.

You know, like, I don't want to be one of those people. What do people say all sizzle and no steak. Like, that's the opposite of what I want to be.

David Elikwu: Thank you so much for tuning in. Please do stay tuned for more. Don't forget to rate, review and subscribe. It really helps the podcast and follow me on Twitter feel free to shoot me any thoughts. See you next time

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