Ep. 006 | The Cost of Delivering Growth: A Conversation with Uber’s Global Lead of New Verticals

May 23, 2022

Where you won’t find trendy business tactics, but you will find truthful insights and timeless stories from leaders to look up to.


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Ep. 006 | Curate Conversations With Pia Beck

“If you are totally focused on that top line, you may not be making sage choices…making sure you know why you’re growing and tying yourself to the right metric is really important..”  — Jessie Young 

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In this episode, we host Jessie Young, who leads Global New Verticals at Uber, which means launching new products, categories and operations around the world.

Jessie is an Aussie in New York and loves her job because she gets to solve difficult pioneering puzzles. She’s also a yoga teacher, amateur surfer and lover of coffee and red wine.

With a background as a lawyer, management consultant and finance leader, she boasts a host of failed and flourishing start-up experience as both a founder and an advisor. She believes she’s here to experience the depth and breadth of life, so she has an itch to solve problems.  She’s a commercial leader and strategic operator with deep experience scaling B2C businesses where she breaks down complex problems into practical, commercial solutions and rallies teams around strategy.

Our conversation centers around the cost of delivering growth: Jessie’s leadership lessons from launching and growing a global grocery online delivery business through COVID. 

Her take is that we problematise our sometimes blind celebration of growth for growth’s sake — so we spend this conversation unpacking the cost of growth. We discuss the paradoxes and tradeoffs of growing a business, including when topline growth comes at bottom line cost, why peaks necessitate troughs, and how to balance risk and rigor.

We talk about putting the consumer at the center of the questions we’re asking about growth, untethered growth and making decisions based on the wrong metrics, and how to entrench the loyalty of our consumers.

I hope you enjoy this episode.

Links mentioned in this episode:

Special thanks to our sponsors, Parker Clay (code CURATE15) and SeaVees (code CURATE20). Music created by Queentide.



 [00:00:00] [00:01:00] In this episode, we host Jessie Young, who leads global new verticals at Uber. Which means launching new products, categories, and operations around the world. Jesse is an Aussie in New York and loves her job because she gets to solve difficult pioneering puzzles. She’s also a yoga teacher, amateur surfer and lover of coffee, same and red wine. With a background as a lawyer, management consultant and finance leader, she boasts a host of failed and flourishing startup experiences as both a founder and as an advisor. She believes that she’s here to experience the depth and breadth of life. So she has an itch to solve problems. She’s a commercial leader and strategic operator with deep experience scaling B2C businesses, where she breaks down complex problems into practical commercial solutions and [00:02:00] rallies teams around strategy.

 Our conversation in this episode centers around the cost of delivering growth. Jessie’s leadership lessons from launching and growing a global grocery online delivery business through COVID her take is that we problematize our sometimes blind celebration of growth for growth’s sake. So we spend this conversation unpacking the cost of growth.

 We discussed the paradoxes and trade-offs of growing a business, including when top-line growth comes at bottom line costs. Why peaks, necessitate, troughs, and how to balance risk and rigor. We talk about putting the consumer at the center of the questions we’re asking about growth. We talk about untethered growth and making decisions based on the wrong metrics.

 And we talk about how to entrench the loyalty of our consumers. I hope you enjoy this episode.

Before we get into the episode, let’s hear from our partners.

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Welcome Jessie. I am so excited to have you. I cannot wait for this conversation. I’ve been looking forward to it for weeks now. I can’t wait for our listenership to hear everything that you have to say about your experiences. 

Thanks so much for having me Pia. I’m really excited to meet you and likewise have been really excited to have a chat with you and.

 So the first question that I like to ask is in your own measure of success, qualitative, quantitative, whatever you want, tell us what you’re [00:04:00] proud of. So for example, this could be your top or bottom line metrics. It could be go to bed, go to market benchmarks, it could be growth or learning lessons. It could be anything about your journey that you’re really proud of.

How do you measure that success? 

I think, invariably the first thing that comes to mind is how I measure it from a business perspective. So I don’t think that that is necessarily the same, uh, measure of success for postal life. And that’s probably something that’s worth interrogating at some point too.

But when I think about how to measure success in a business sense, I would really think about it in terms of sustainable advantage. Which to me means three things. It means how do you grow your top line? How do you scale your bottom line and how do you entrench the sources of your competitive advantage? And ideally you can do those three things in a re-investing loop.

So when I think about what I’m really proud of or what success looks like in my role at Uber watching some of our new [00:05:00] verticals over the last year, I think about how we have almost 40 X, our top line growing a business that really, Didn’t exist sort of 18, 24 months ago in terms of this hyper fast on demand grocery offering.

I think about how we responsibly scale the bottom line and what the trade offs between cost control and investment look like. And I think about how we have really come to know and own what the sources are of our competitive advantage, whether that needs, because there’s something really unique to our business. Or because that’s something that we can do that we know is going to be really hard to replicate. How do you really double down on that to get the most for your consumers.

So I’m really proud of, of those things in terms of how we’ve been able to grow our business. and then I think when I look forward it’s how can we continue to do those things in equal measure?

 I love that three-part answer. And I think that we’re going to get more into the first two and kind of how they work together, which I’m really excited about. [00:06:00] And what I want to say right now is that, that last point about almost like building a moat around what you’re doing really, really well is something that’s super interesting to me.

 And it’s something that we’re really focused on at Curate Well Co too. And you mentioned those are knowing what you’re really good at. And really leaning into those things and also pursuing things that are, you said, like hard to replicate. So tell me more about what that looks like in practice, right? Like this is something I’m thinking about, and I have certain ways that I’m like digging this moat around our community and what I think we’re doing really well and almost making it so that, you know, we’re not even.

 Really sitting on the competitive landscape in some ways we’re kind of like on this island, right. Surrounded by this beautiful moat. and I want to hear your perspective on like maybe one or one or a few ways of what that looks like in practice. 

Yeah, it’s a good one because I. I think [00:07:00] often the actually strategy and in particular competitive strategy is what happens in the gaps.

It’s what you choose not to be just as much as what you choose to be. And so when you think about building a moat, it’s almost thinking about where you are going to choose to be bad in order to be excellent, not bad in the service of mediocrity. Bad in the service of great. And actually that’s where the depth of your moat comes from.

If you are just seeking to hit the floor of consumer expectations, you will only ever exist along out of the mediocre parity of a, of your competitive set. But if you can choose with bravery to say, this is what we stand for. And in fact, in doing that. We can’t be all things and we will choose not to be something else.

That’s where you truly embed sources of competitive advantage. And I think when you’re launching a new business, it’s so easy to get distracted by everything you could be rather than choosing what you really are.

I love that answer. And it’s also a really [00:08:00] confronting answer for me because I’m someone who really likes to be good at things I’m like, I don’t want to be bad at anything.

 And I’m sure there’s a lot of, uh, entrepreneurs and business owners and leaders that can relate to that. Can you give us an example at Uber of one thing that you chose to be bad at in your work? 

 Yeah, it’s too good. It’s another, it’s another really good question. I. I think first about how we stratified, what delivery of e-commerce needs meant. And, that probably sounds a lot more erudite than it was, but it’s really, it’s really trying to decide where do you go first based on what matters to your customer most?

 And so as a company, we could say, we have this delivery network are independent contractors who can theoretically move anything from A to B. And if that’s the case, then why don’t we just move everything from A to B? Why don’t we think about fashion? Why don’t we [00:09:00] do books? Why don’t we do pharmaceuticals, why don’t we do food, let’s do it all. And instead we said, what are the things that matter most to our consumers? And where will we really outperform on those expectations and more on, but not just then, where do you play? But how do we win in that space is to say, and where are we uniquely positioned to deliver on those needs?

And so an example there is, we used to, we used to talk a little bit about this idea of a share of stomach. If you imagine like the pie chart of your market share is actually just your share of stomach. And you would say, well, you know, if eating restaurant food was one sliver of that share of stomach, where else is the consumer filling this stomach?

And do you want to go to try and services much of those eating occasions as possible? Or do you want to serve as, as much of a delivery occasion as possible? And what does that look like? And think Uber made the choice to say. The next step out of restaurant delivery is into this grocery delivery space.

And [00:10:00] when I first started playing around in the concept of on demand grocery, this was pre COVID and, it was very much still a nascent space. I think on-demand grocery delivery has erupted over the last year in particular. There has been over $10 billion of funding and this hyper fast, quick comments proposition around, you know, sub 20 minute delivery of groceries.

But we chose to, to extend to what mattered to our customers rather than spread ourselves really thin across everything, and then add to that proposition over time. But it’s a question not just about what you offer your customers, but I think how you think about your overall marketplace as well, you know, Whenever you have a marketplace eucharistic that is fundamentally about balancing supply and demand.

One side, wins at the cost of someone else. And so understanding the elasticity of both sides of the marketplace and knowing how to trade off on where Eden needs to pay less or where a delivery partner needs to be paid more. And what that trade off looks like also becomes really important. 

 I can get [00:11:00] that the elasticity that you’re talking about is something.

 Is not as talked about as it could be in small and medium-sized businesses. Right. I would imagine that at a very large company, like Uber, there’s a lot more of that conversation. And speaking from my own experience, working with, much smaller businesses, I think that’s something that people don’t realize can be an advantage.

I think that there’s this like false sense of r igidity of it needs to be both. And how do we make it both? And I think that there’s so much freedom and choice, which is something we’re going to talk about again later, this idea of choice that comes with recognizing that the elasticity and it holds so much room for creativity and problem-solving and ultimately a better outcome.

So that was super interesting. And your answer actually queued up my next question perfectly. So. You recently launched Uber’s first series of quick commerce, grocery stores in Japan and Taiwan. And that means that Uber eats customers can now get groceries and alcohol [00:12:00] delivered in under 15 minutes. So, correct me if I’m wrong, but in your last, little spiel that you gave, you mentioned leaning into what you know, your customers really, really want.

Right? How do you outperform on expectations? And it sounds like the delivery time is one of those things that’s really important to your customer. So that 15 minute window. The sub 20 minute window is the thing that you decided to really lean into and be exceptional at. So. I want to talk about the culture of like urgency and instant gratification that we live in and how you think that dictates just business growth in general.

Right? Obviously it played a really important role for your work and what you and your team are doing inside Uber. And I’m curious to learn a little bit more about that. And if we think even broader than that, we’re living in a culture of instant gratification and I’m super guilty of this too, right? I’m like 15 minutes, done. So I’m curious how you think that that really dictates how businesses grow or how businesses choose to grow and what that means for their relationship with consumers. 

Yes. I think it’s [00:13:00] in many ways, the need for a hyper-fast delivery is a beautiful or twisted I’ll agree for her, millennial mentality more broadly, which is this kind of right off sometimes between the push for that, which is instant and the push for that, which is highest impact. And I think we are in particular, such a generation that is in such a rush. We are so keen for the, the next thing. and we are, we are unashamed in how aggressively and, uh, basically we push towards that next thing.

 I think what is fascinating about that is that the next thing sets the floor for the present rather than the ceiling of the future. So what I mean by that is like you are, we are often living two or three steps ahead of where we are currently and striving to the next life goal that we might achieve.

And that sets these artificial expectations for where we need to be right now [00:14:00] and sort of an, an itchiness or an unhappiness with where we are right now. So you start to want things that you never really knew that you needed, but having had access to it, you now believe in your right to have. Whether that is impact or not.

But the instantaneousness of it is something that you demand and it’s like, nobody knew that they wanted their groceries delivered i n under two hours until the 30 minute option was available. And then suddenly when you can get your oat milk and your bananas and your shampoo delivered in sub 15 minutes, you would find the 30 minutes unacceptable.

 So we’ve reset kind of the floor of expectations around when you should be able to get your needs satiated. Um, but what we haven’t necessarily done is elevated people’s gaze into, you know, what that means or w hy they need that. And I think that’s a really fine line in the mentality that we have. On the one hand, I have immense respect for the ambition and the hospital of always wanting to push this data score.

Be faster, be better, be more optimized. Push into something [00:15:00] else. On the other hand, I think we see our generation and the generation underneath us having a reaction against that and starting to push back into really conscious mindfulness. Movements like, conscious capitalism to say, where am I trading that need for more, with the need for more impact and where can I sit and be mindful in what I have.

And I think that’s like a, that’s an interesting thought for businesses to be operating in. It’s an interesting spot for individuals to be operating in and it’s also interesting for consumers. What I would say is that when I think about it, if we take the idea of like how fast you can get something delivered as an allegory for all of this, I actually don’t think encouragingly that super fast necessarily supplements, uh, the scheduled or next day or more mindful consumer activity. I also don’t think that it replaces people’s in store behaviors. I think what it does is it creates an incremental use case for how people engage. And if I [00:16:00] could extend that allegory to that kind of hustler mentality, I think ultimately you probably want to get to a point where you can balance both where you are pushing and the time to push, the time to hustle, the time to sit ahead of yourself. And also the time to sit back. And those two things can exist side by side.

 So much to respond to there. That was like, so beautifully said you hit on, like all of the things that I was curious about. I’m going to pick one thing to like hone in on and, acknowledge about everything you just said, which is this idea of like instant versus impact. And I think that you totally nailed it with like the generational, perspectives in which of those things is more important in how that changes over time.

And what that sparked for me was this idea of impact. And, I think it’s pretty clear what the impact on the consumer is. And one thing that I didn’t necessarily hear you say that I’m really curious about is the ripple effect of that impact into, you know, our supply chains into the people who [00:17:00] are working in the system into where we’re sourcing the material, just like how does that like affect all of the layers that go into delivering something in two hours and then 30 minutes and then 15 minutes and then five minutes. Right? What is that? How does that leave our world on a grander scale than how it makes the consumer feel? And maybe we don’t know the answer to that question yet. It just really got me thinking about the bi-product impact in addition to the direct to consumer impact.

 Yeah, totally. I mean, we all know that like supply chains generally have been really distressed by a lot of macro economic factors over the last year that have fundamentally changed the way that businesses can operate and serve their customers. I think it’s really fast delivery model is certainly an interesting one because in a lot of ways, and you see a lot of companies almost gamifying that whole order fulfillment [00:18:00] right through to delivery mode, where it is, faster and faster.

And, companies are very, you know, companies incentivize people to move as fast as they can. And is fast better for the individual? Does that mean things get missed? You know, how, what you think about all of those things? Actually, what, one thing that I’m really passionate about and, why? I think, a company like Uber uses its scale really well, is that with access to scale comes access to data and with access to data comes the ability to optimize your operations much, much more effectively. So that you aren’t just rushing mindlessly. You are moving quickly and efficiently, and actually that speed generates better efficiency and drives down wastage.

 I’ll give you an example. If you are on these kind of quick commerce style offerings, typically what you’re talking about is actually a very curated product range. So if you were to go on to one of our grocery [00:19:00] locations in Taiwan or in Japan, you wouldn’t necessarily find a 20,000 product menu like you would if you went on to your online grocery, big basket shop. Instead, you could probably find, one to 2000 of the products that matter most. So you might not have all ranges of oat milk. You’ll just have the oat layered milk because that’s the one that you really want. And what we’re able to do is work out what customers really want. And nail in on our supply chain to reduce wastage by a factor of sometimes three X lower than what traditional merchants do. And that’s not because of anything, particularly more erudite than being able to use data, to understand what your customers need and how they need it, and then optimize your operations for it.

So in some ways, that’s the, it actually enables you to have a greater impact and a lower footprint because you can get to more efficient operations. But there is definitely the other flip side, which is that if you are just scaling so rapidly, there is [00:20:00] invariably so much waste that can be associated with that kind of culture of the capital markets and the top line growth story without really considering what that bottom line looks like.

 I think that that’s a really p owerful reframe for two reasons. So, number one is that I think a lot of the, and they’re related to each other, a lot of the businesses, in our community, I think, think that they don’t have access to that kind of power. Right? Like my, my community is smaller. My data is smaller.

And so, you know, I can’t optimize, I don’t have that power. Right. I’m, I’m not as, as proximal to that much data as really big companies like Uber and you know, all of the friends in that tier. So I think that it’s a really good reminder for businesses of all sizes. To remember that digging into the data is power.

No matter how much there is, as long as it’s accurate, it gives you the, it gives you the opportunity to optimize in whatever way makes sense for your business. [00:21:00] And I think that it’s also a really good reframe for how we all view t hese huge corporations. Right? And so long as those corporations are leveraging that power for good.

 It gives me a lot of hope, right. To know that like, that’s how you’re thinking about it. Right? You’re in charge of these verticals that are emerging on behalf of this big company that we all know. And it really makes me excited to know that there are people like you on these teams who are really thinking about how do we use that scale?

How do we use that data to create this downstream effect that is going to benefit our consumers that is going to help our supply chains rebound from all of the challenges that they have been impacted by over the last couple of years.

 Yeah. I, I mean, I think that’s, that’s what corporate social responsibility looks like in the inner digital age is, truly that. And, you know, [00:22:00] we have had some conversations prior to this about the role that the secular economy plays in all of that. I think that’s why I’m so passionate about like a marketplace business that reinvests in itself because I think that’s really where shared value comes from. And I think, I think that’s also how, the way we began the conversation you get to like, you get to success as a business. It’s really about that sustainable advantage and you are endemic in your community and, and it needs to ultimately benefit the community and ultimately.

I don’t use that term circular economy when you were describing your work prior to our conversation and you just use it again. So this wasn’t a term that I was super familiar with, and I’d love for you to just pause and like, define that for us. What does that mean? What does that look like? How does it work?

Sure. So, I mean, at its loftiest, the circular economy is defined as a systems or solutions. [00:23:00] And it’s often used in the lens of how to tackle global challenges like climate change, biodiversity loss, waste, and pollution. Fundamentally, and for your listeners, it’s a model of production and consumption. Which effectively involves sharing, leasing, reusing, repairing, refurbishing, recycling, existing materials and products for as long as possible.

And so you could think about that in terms of physical products, but also you could think about it in terms of, metaphysical products. Like your time or your capacity and how you reinvest like capacity back. So an example of how Uber perhaps even does that is, is taking literally the latent utilization of a car sitting in a driveway or a person with a remaining four seats as they do their commute and starting to move extra and starting to take the surplus demand of consumers who are looking for a ride share and feeding that back through itself. And actually that creates a self-fulfilling most sustainable circular [00:24:00] way of, of using resources. 

That example was perfect. I think you hit the nail on the head in terms of, giving all of us a really tangible way to understand that concept.

 And I think that this leads me to another question, which is that you have two big passions, right? E-commerce and community. And you come from the perspective. And I think that I can get there too, that they can be woven together in, in really meaningful ways. And so y our inspiration comes from the way that people consume and making it empowered and sustainable and connected.

 I’d love to hear a little bit more about your personal vision for the world. So when e-commerce and community are woven together in really impactful ways. A nd that happens at scale, there’s like critical mass adoption of this practice and this idea, what does that look like for consumers on a day-to-day basis?

 I think the reason that I really love like e-commerce and like the consumer world is that fundamentally we exist in a physical world, but we are [00:25:00] tied together by ephemeral community, all of like shared beliefs, values and ideals. And so it is this constant question of how you reconcile the ways that you consume, interact and move through the physical world.

We have these more ephemeral ties that are what bring us together that enable us to cooperate, to share, to trade and to invest, to invest in ourselves and in our futures. So I think w hen I try to reconcile those two ideas. Fundamentally, if you are then offering something in the physical world or interacting in this physical world, you need to be taking your consumers’ needs that their beliefs, their values, their ideals, and reflecting that in your product.

And if I think about them, selfishly my vision as a consumer, I then think about the kind of community that I want to be a part of and what those shared beliefs, values and ideals are. And if they are ones of [00:26:00] love and kindness, fulfillment, sustainability, growth, equal opportunity, empowerment. Than I will support the products that in turn enable that.

And so whether that is on a scale like Uber’s, which is about creating earning opportunities for people. I ncremental opportunities for local, and loved brands and restaurants to meet new consumers. Consumers to interact with new products, to get things delivered when they need them so that they can take the fuss out of their lives and continue to focus on that, which matters more. That might be one element of it. A much more micro element of it might be just the brands that I choose to consume. What they represent, how they’re manufactured. What their promise to me is, and I think. It is there, isn’t a silver bullet answer for how you thread the needle between the two, except to say that actually the two are products of each other.

The physical is a product of the community that we choose to build on the community that we choose to build is [00:27:00] invariably, a part of that product. 

Community is in my experience, just such a critical element of business success. Every single way. Whenever I meet business owners who say that they don’t have a sense of community, whether it’s around shared beliefs or ideals or an actual like network of resource people, or a place to go to be heard and understood it’s, evident immediately in their work, if that’s something that they don’t have.

 And so I’m totally tracking with you there. And I think that you brought up a really, really good point, which is. In our, like increasingly digital world. It’s a really easy to think about business in terms of click patterns. Right. And I think it’s really important to remember that even as technology continues to advance, even as companies are really pushing.

 What we come to expect as consumers and setting that tone that even [00:28:00] at the foundation of all of that always is the human experience is this idea that we are connected through ideals and values and shared beliefs and that that shared human experience. It can’t possibly ever go away. Despite advances in technology.

 Yeah. And I, I, when I reflect on, the last year or 18 months and the impacts of lockdowns and the way that, you know, your teams would come together or the way that even families couldn’t come together, you, we have theoretically more connected than we’ve ever been for the greater part of COVID lockdowns.

I was actually stuck in Australia and was working with my team in the Northern hemisphere. And that was, that was an incredible thing that I could continue to do my role from halfway around the world with theoretically more connected than ever, but also feel so much Penfield, so much more isolated than [00:29:00] ever as well.

And you can’t, you can’t fake that authentic connection of a community. It has to come through a very, a very honest and resonant and real place. And I think, you know, the brands that hit on that really well, they, they do it not because it’s a quick bite strategy or a marketing play. They do it because it is authentic to them.

And that’s actually also why they are so impactful in the long run as well. 

100% in our community. We say that a lot of people think about community as a now, right? It’s a thing that exists. It’s a group of people and actually community is a verb it’s generated.

 Okay. So your work across all of your ventures of which there have been very many is about empowering people with choice. That’s the thing that they all have in common among, among other things. So tell us what it looks like when a business doesn’t do this for this consumers. When a, business doesn’t empower their [00:30:00] consumers with choice. What does that look like?

 We think ultimately as consumers, what we’re all looking for is a way to express our own agency. And that means a way for us to bring things into our lives that both reinforce what it is that we do, what it is that we stand for, and also send a very clear message to. The community around us, that this is what we do in the future.

We stand for what we stand for. And that’s fundamentally comes back to who you are and putting you first. Which means that when a business loses sight of that, and then no longer putting the consumer at the center of the question, then that’s fundamentally compromising, not just on their consumers, but they will lose them and then that attraction over time. Because consumers will turn and examples of where I think companies do this all the time is f raming problem statement for their business around, the problems with the corporate. Or the [00:31:00] problems of the business. As opposed to the problems of the customer.

And if you want to put your individual customer first, what is it that they would really seek? And what does their journey look like? Because you were in ability to tap into that and penetrate that actually is like the inability of you to do your business properly. And frankly, you lose your license to operate with that community.

 So I think what it looks like very practically when a business does it. Well, it doesn’t empower the consumer with choice. It means that that consumers know local first and that consumers fundamentally compromised. But moreover, the business is fundamentally compromised. It’s a challenging world when you’re in a kind of dividend reinvesting culture or the startup, and you’re promising a growth story.

It is very easy to lose the forest from the trees on those things. And sometimes, doing what is right is not what is easy. And doing what is right is putting that person first. And that’s a, that’s a challenging thing. 

And I can give you an example. I was recently just actually, just before this, I was talking with, a [00:32:00] founder, about why they had chosen to invest so heavily in their instore support network.

That basically that is when something goes wrong with their e-comm platform. They have a group of people who sit in their office space, shocking to people going into offices. These group of people sit in the office space and take those calls. One-to-one now an onsite support system is really expensive.

Anyone would, would know that in a lot of, a lot of companies will automate that they’ll use bots style, dealt with the very leaked off offshore it. But to have these group of people sitting there was a fundamental part of how they valued their customer experience. And they said that’s because the cost of this particular product gone badly, is so bad to our customer that we won’t make that compromise. If they didn’t put their customer first, any person in finance looking at the P and L would say, this is an opportunity to slash out some costs or callbacks and margin. But I think it was a really brave choice. And frankly, I think it’s the right choice.

And I [00:33:00] think it’s why this, this brand will do really well over time. 

 Totally. I was just reading something literally like three days ago that talked about how easy it is to look at the P and L and to say like, this is a massive expense we should slash this. And though, if you consider what it would cost the company to lose a high value customer, it actually isn’t that much of a question at all.

Right. You end up losing more. If your best customer. You know, it says, bye, I’m going somewhere else because this support didn’t meet my needs.

Yeah. And I think the bigger you get the risk is at the more untethered you get from your customer? I have my own very small business as well on the side.

And I’m deeply attached to every customer. I make headbands. And every time someone orders a headband, my God, my husband and I do a dance around the kitchen. Like I am deeply, deeply connected to these people, but you think about a platform like Uber that has hundreds of millions of users and. It is easy to think about people as [00:34:00] means and mediums and statistics and averages and cohorts, and not to think about that individual experience.

So it’s really incumbent on companies as they’re scaling, particularly out of those early stages to then think about the ways that you can align the right incentive structures to come back to what matters most to your customer, because you definitely feel that with the big companies that lose their way on that basis.

Absolutely. That was perfectly said. 

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 So one we’re talking about that right, growing into a huge business. There’s trade-offs that come with that? And I think that it’s, again, is something that is not talked about often enough. So the examples you gave is when top line growth comes at bottom line cost and or why peaks, necessitate, troughs, and how we balance risk and rigor.

So those are some of the things that kind of queue up these trade-offs that we’re going to be talking about. And in order to transition us into this part of the conversation, I would love to read the excerpt that you sent me about your experience with this, if that’s okay with you. Okay. So, before this conversation, Jessie sent me, this excerpt, I’m going to read it word for word, and then we’ll kind of dig into some of the follow-up questions and what this looks.

 “I was laundering grocery [00:37:00] delivery in Australia. When COVID lockdowns hit in March, 2020. Within 48 hours, we were on calls with the C-suite of Australia’s biggest retailers and government officials about how to bring food to the people of Australia, if lockdowns needed to continue. Within a matter of weeks, we went from piloting a proposition in Australia to launching a new grocery product globally that grew 45 times over 24 months. I launched this product and then manage this new vertical across five countries and worked across almost every major time zone from my living room in Sydney. As my career grew, I literally withered in the space of three months. I lost 40% of my body weight and ended up in hospital with a heart arrhythmia. At almost six feet tall, I was 42 kilograms, which for those of us in the U S is about 92 pounds. I replaced food with fury and adrenaline sleep with the zoom meetings and a myopic focus on growing the [00:38:00] business with depriving myself. The business flourished, but as a leader, I floundered. And certainly as a partner and friend, I fell short, especially to myself.”

 I wanted to read that because when I read it in your words, it just resonated so significantly with me. That idea of the business flourishing, but myself as a leader, floundering is something that I’ve totally grappled with and I’m not operating at the scale that you and your team are, which I have a follow-up question about.

 And it just, it just like hit me like right where it counts. I was like, oh yes. Like, I think this is something that every person involved and passionate about growing something that they care about can relate to on some level. And one of your main takeaways from this experience was that ambition and ability are key for growth, especially hypergrowth. But intention and investment are key for sustainable [00:39:00] growth.

So I want to hear a little bit more about that. And maybe before we do that, you can tell us how big your team is. You mentioned managing your team from Sydney and the Northern hemisphere. How big is your team? 

Yeah, so my direct team, as in my like SWAT team in New York is like by people it’s crazy lane.

And then we have, uh, teams that scale that around the world. So we’ve got like, say about 200 people now in the US. We’ve got hubs around AMEA in north Asia and and so it’s all about working alongside and deploying through each of those markets. But as we launched these products, we didn’t have teams in market.

 So we actually started with this super duper lean swat team of people that were just passionate about growing the business. And it’s incredible what you can do when you combine, passion and caffeine. But we did, we did some really big things really quickly and then, and then scaled out the teams.

And now there are these, these incredible [00:40:00] powerhouse, new verticals teams that are instilled in each market that deal with our merchants day to day and you know, sit on the ground.

It blows my mind that that growth started with five people. And I think that is such a good thing to call out for all of our listeners. Because again, I think that people discount themselves. They’re like, oh, well, I’m not a massive company like this. And so it’s really refreshing to hear that it started with literally five people on your team. And that you have been able to grow it into this global initiative. So, okay. Thank you for sharing that. I feel like that’s really helpful context and circling back on my question, you had said intention and investment are key for sustainable growth. So tell us more about this experience and that learning that came out of it and, how we apply that. 

So context for how I acted this is my mom is an English teacher and therefore, please don’t hold it against me, but I’m a real like literature nerd. But there is a, there is a line that I love, um, it’s Shakespeare. And he says, “when valid praise on [00:41:00] reason, it eats the sword it of fights with”. And when I think about my experience, Shakespeare has said it, but I lived it. And I think many of us have. So there are three things that, play out is true in that. The first is that yes, you must have that valla.

You must have that ambition and it needs to be underscored by a fundamental capability to deliver growth, in the arena that you’re stepping into. But what I mean by then intention and investment as being key for sustainable growth is that eventually that valla or that ambition may eat you alive. That levity prevents you from being grounded enough to sit back internalize and pay it forward.

 Set your gaze long, but bring your sites near and don’t lose sight of the present and your immediate sphere . Because when you are not servicing that, you’re actually unable to pay forward into the future in the way that you would want to win. Even if you are incredibly [00:42:00] capable, eventually you will flounder.

So I think that’s the, that’s the first thing that I learned. The second thing that I learned about this whole experience is that, trust and vulnerability are predicated on each other in equal measure. I think most of us understand intuitively that order to be vulnerable, you have to trust. But I want that equally in order to trust, you have to be vulnerable.

And so integrating your shadow is one of the most powerful ways to step into yourself as a person and as a leader. I think a lot of the time you think that valla and courage and ambition means being impenetrable and being invulnerable. And actually when you are able to claim those parts, not just to express that, to say your team or your circle, but also to claim those parts in yourself. You become so much more powerful and trustworthy as a leader.

So that was the second thing that I. And the third thing that I learned that [00:43:00] I think resonates a lot with very ambitious people, is that perfect is not a position to defend. I n business, in fact, perfect is the enemy of good.Take bets, stay fast and grow. life, perfection is an unattainable standard and it’s a false performance.

So instead aligning or intentions, rather than outcomes will up level your performance. Or without setting you like unachievable and arbitrary standards for the value that you bring to others. And I think if you can really, really sit in some of those things and you are much more willing to take the bets that you need to, and also to move on and think through them.

 Absolutely speaking from my own experience, doing the really uncomfortable personal work is A, like the thing that needed to happen as I’ve continued to step into my role as a leader in my business and in my community and [00:44:00] B, is the reason I have been able to continue to become the leader that I want to be like both of those things.

Right. I was confronted with it immediately and was like, all right. Look at this, it came to the forefront really quickly. And then have, when I reflect on the things that I feel have equipped me most to be the leader that I am, it’s the things that came out of that personal work as well. So just wanted to echo what you said.

That that is just a huge, a huge factor, I think on a very, intimate yet universal level for all of us. And you mentioned putting our focus on the intention versus the outcome, which relates to another question that I had and something else that you mentioned, which is this celebration of growth for growth’s sake and how that can be really problematic.

And so focusing on the outcome is that right. It’s celebrating the growth that comes for the sake of growth. And so I want to break down and sort of unpack this cost a [00:45:00] little bit and talk about why this is problematic. What would you say if I said, why is growth for growth’s sake problematic? What’s the first thing that you would say.

 The first thing I would say is that that growth is therefore necessarily untethered. And if you don’t know your why, then you will l evitate off. You will split yourself apart and you will frankly miss the point. So it really needs to be tethered in your why. And we talked a little bit about, your consumer, your customer is fundamentally being your why in business.

I think as an individual too, we lose sight of that sometimes because we can get so distracted by seeing what everybody else around us is doing, you know? This person’s business, just got this round of funding. This person got married this past and had a baby. This person lost this much white people doing all these things.

And you start to think about your life as a series of outcome-based goals. Perhaps they are not truly [00:46:00] fundamental to what matters to you. And so if you lose the why then you will untether yourself. So I think that’s, that’s probably the, the first thing I would say. The second thing that I would say about it is that when you are untethered, then you start to make decisions based on the wrong metrics.

So you tie yourself to the wrong hero metrics. And so that might be a growth multiple at all costs. And sometimes it is really important to invest in order to grow. And certainly, I think in early stage companies, you can chase profitability too fast and you know what the cost of reaching the right efficient frontier on scale and reinvesting in your customer base.

 But similarly, if you are totally focused on that top line, then you may not be making those really sage choices. so, you know, further down your P and L. So making sure that you know, why you’re growing and tying yourself to the right metric is really important just as, as an individual. I think knowing why you want to go somewhere and then tying [00:47:00] yourself to the right metrics is really important.

 Yeah, absolutely. The word untethered was super powerful. And I want to circle back on something you said earlier now makes complete sense to me that your mom was an English teacher, because your vocabulary is just totally spot on. And I’m just so impressed by the language that you use. It’s it’s really, really resonate.

And it was resonant when I was reading it as resonant in this conversation. So I just wanted to acknowledge you for that. You, maybe send her this episode, let her, let her listen in and she can take the compliment too. Um, so you mentioned reinvesting in somehow and that’s sometimes that’s, that’s really critical for growth and another learning.

That’s come out for you through all of the growth experiences you’ve had across businesses and ventures and contexts is this personal philosophy of failing fast growing forward and reinvesting. So tell us a little bit more about what this means and, maybe you can give us some examples 

Sure thing. Yeah. So three, three elements to it that I think a lot about [00:48:00] in the context of my team and a context of the business decisions I make. And then also in the context of the personal decisions that I make in that my husband and I make together, the fail fast. I think we both heard it, but to me it means taking risks, celebrating a learning and calling the missteps early. Clear is kind and example is you may know intuitively, or you may have been very passionate about a particular business idea, something that you should be pushing on. And then it becomes abundantly clear that, that’s actually not the right path forward.

 The ability to say the learning here is the value, not the outcomes. Stops you from f logging the dead snake. It is the expression that we would use in Australia. It’s is important to cut your losses and to move on fast. And I think, there is actually nothing to be ashamed of when that, and the ability to separate yourself from that outcome is really important.

So that’s the first thing is call it early The second one [00:49:00] grown forward. I think in terms of my team, that means that we keep out gaze elevated, but our sites near. So we build for the future, but don’t hold on to parts processes and call out the confirmation bias. Learn from the past. For sure. But know that the future is where you’re heading.

And so don’t hold onto past resentments pathways of working past missteps that others have made, or maybe wrongs you on, or that you feel wronged by. Instead learn from it and then let it go and keep your eyes forward and keep moving forward. And the third part, I think reinvestment is a really important part.

Often we can say that we failed either way going forward, but then not pay it back. And so I think to reinvest is where you really embed the sources of your advantage. Um, and they have to be self-sustaining so reinvesting your people and your customers and in the community of. I don’t pocket the upside I pay it forward.

An example of that is as [00:50:00] you really start to get your operations working well, so you’re able to drive down your consumer facing pricing. Instead of pocketing, that margin. Think about either how you can create a better experience for your customer or reinvest it to find new customers who maybe didn’t have access to you before.

How might you change your pricing, your service, your quality in order to pay it forward and pay it back and keep that system going through. You know, they are as applicable in businesses as they are, as they are personally. And a lot of the time you already know all these things. It’s just about having the courage to call them out.

 Totally. The first point you made around failing fast is something that I really had to learn the hard way. And it did take a lot of courage to shift into that. So I totally relate to that. One of the things I’ve struggled with is the sunk cost fallacy. So I’ve already put so much into this do I really want to cut my losses? And then the emotional side of that, what does it mean? Like, what does it mean about me or what does it mean for me? If I, you know, admit that [00:51:00] I can’t make this work anymore or whatever it is, and learning that the hard way and learning how to call it early was r eally like clear. It was like that like kick in the gut they got learning that you need to learn so that you, that you need sometimes right of, oh my God.

If I had just pulled it quits, the first time I had this like, intuitive ping that it was just like, not going well. Think of the, not even the money so much, but think of like the stress and the like a challenge and like a friction that I could have saved myself over the last, however long it was. I totally relate to that one.

 You mentioned, you know, not pocketing the upside and instead paying it forward through reinvesting back into the business. And I know that this is right in your wheelhouse, so I’m wondering if there is a, obviously it’s going to vary situation to situation and there’s no like hard and fast black and white rule, but if someone was saying, okay, how much do I reinvest?

What does that look like? Is there like a proportion? Is there a percentage? Is there a guideline so that I can answer this [00:52:00] question for myself? Do you have any advice on that? 

I mean, I would say that it really depends on the stage of your company and what your, well one, what your, what your growth targets are and two, what your obligations are to your investors or your shareholders.

But when you are growing at a new line of business, I think. What is important is that there is obviously a path to profitability and that you are very clear on the leavers that you need to pull, but then it’s being very mindful on when you pull down on them. And a big learning that I have is that I think you can, you can race to that too fast.

 It’s going to sound strange to some people, with, You’re talking about that. But when I reflect on some of the new lines of business that I’ve managed. I was clear on how to hit that path early when actually having command of the leavers, and then knowing when I was going to pull them and maybe holding back.

To grow faster would have been a smarter play because we would have hit more customers faster. We may have entrenched more loyalty foster. And then once you have [00:53:00] that, I might’ve be more effectively able to pull down on some of the other core structures. So I would say like, no, you know, your path to break even, and then know what your end game from a margin perspective is. And know what your payback is going to be and let them the guardrails on what that time period looks like and what those margins look like. Be determined by the people that you’re ultimately accountable to for your right to operate.

But then don’t just sit outside that, willingly reinvest where it makes sense to do that. 

That was a perfect answer. Thank you so much for that. Okay. So I like to end with two questions. The first question is if you were to give one piece of advice to business owners, especially those looking to stay at the forefront of evolution in their industry, what would it be?

 I think I come back to something that we talked about earlier, which is to choose to be bad in order to be excellent. And like I said, a little bit earlier. Yeah, no bad in the service of mediocrity, [00:54:00] but that in the service of excellence. Be deliberate on what you choose not to do so that you can truly excel. Because that is where you will find the greatest impact and the greatest growth.

 I think that is something that everyone absolutely needed to hear. Thank you for reiterating that for us again. Okay. Last but not least, I like to leave our listeners with a mic drop moment and what you just shared was amazing. So maybe that was your mic drop moment, but I want to hand you the microphone and I want to invite you to say the thing that you feel needs saying,

What I’d like to say is a question. Which is what if that what you fear the most is not your inadequacy, but your tower. And how would you realign your behaviors to an ambition defined not by what you see but what you seek to achieve. What I’ve come to learn is that when you command yourself with absolute soul trinity. In the knowledge that everything you need [00:55:00] is innate that your creativity, your divinity, your lovability is enough.

Then you might just step into the edges of what is possible and you might really start to learn and to live.

 That was so powerful. Thank you so much for this conversation. I feel like I could’ve continued to ask you questions for the rest of the day, so we need to do this again so I can ask all of the other questions that we didn’t have time to get to today. Your work is so interesting and we only even touched on like one small piece of all of the work that you’ve done and are currently doing.

Thank you so much for showing up with so much eloquence. 

Jessie is a catalytic learner and problem solver with deep commercial expertise in e-commerce. She has a background in law, finance, operations, and strategy, and specializes in taking businesses from zero to 80 quickly. She is a thought partner on how to scale your business for sustainable growth. And she’s up to incredibly cool things inside and beyond her role at Uber.

This episode was a fantastic [00:56:00] look into what it takes to grow to the level companies like Uber have. And what I really loved about Jessie and her dialogue is that she broke the barrier to accessibility. I think it’s easy when talking about the companies that have fundamentally changed the way we live our lives to feel so separate from that.

And Jessie really grounded us in what we as business leaders have in common with companies like Uber. I so enjoyed Jesse’s insight on changing the discourse, that’s happening about how we measure growth. And her commitment to the conversations that need having. This conversation led me to get more curious about the paradox of interconnectedness and agency. Beautifully reminded me that when we’re strong in ourselves, we can also be stronger together.

 And created a resonant visual for me that when we press on one piece of the web, it will reverberate around the rest of the marketplace.


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