Episode 233 Featuring Alex Bond

Solo Entrepreneurship with Jessica Totillo Coster

Solo Entrepreneurship with Jessica Totillo Coster

Jessica Totillo Coster is the Founder and CEO of eCommerce Badassery as well as an eCommerce & Email Marketing Strategist for scrappy entrepreneurs. After 20+ years in retail, owning her own multi 6-figure brick & mortar boutique, and 3 years as the only employee of a 7-figure eCommerce store, now she’s sharing everything she learned the hard way… so you don’t have to.

On this episode, we discuss a wide variety of topics including customer acquisition vs retention, general email marketing and eCommerce strategy, and much more.


What is eCommerce Badassery

Jessica Totillo Coster: So I actually started this business by accident a couple of years ago. It was when MailChimp. And Shopify broke up and a lot of entrepreneurs didn't really know what to do about their email situation. 

And so I started talking to them about the Klaviyo platform because I had already been using it in my day job and people started reaching out to me asking for help. And it was in that moment that I realized there really was not a lot of information for that mid level e commerce entrepreneur.

And based on my 20 plus years in retail, which is so scary to say that I've done anything for 20 years. But between that and my experience in my previous day job, I realized I had so much information and ways that I could help people. And so that's how eCommerce badassery came about. 

And so my number one goal is to put more money in the pockets of small business entrepreneurs teaching them how to grow their traffic sales and profit because I think that there is this idea on the internet that eCommerce is just really easy and you just like put up a website and then everyone comes and buys stuff and that's just not really how it works. 

So the short story is I take everything I learned the hard way, right? And teach it to these entrepreneurs so that they don't have to learn it the hard way. 

Alex Bond: No, that's great. And I think there's a lot of value in your, in your business model in terms of finding that in between that middle class of entrepreneurs, if you will, where a lot of the people that I talked to and a lot of the brands that I see their services are generally either for someone trying to start their business or bring in six figures. There's not really a lot to get from A to B. It's kind of like, come call us when you can bring in six figures.

So I think the service you're providing is very valuable. Is there a certain way that some of the techniques that you talk about or some of the services you provide and the strategies that you go over? Are there certain ways that they're just not applicable to bigger brands or smaller brands? Like how is it specifically catered to middle class entrepreneurs as I'm calling them? 

Jessica Totillo Coster: Yeah, for sure. No, I think that's a great way to describe it. You know, I think the big thing that I learned early on after talking to so many entrepreneurs is a lot of them, you know, they caught some traction and they're doing well, but they're not.

Like a hundred percent sure how they got there. So they don't know how to repeat that success. Like how do they get to the next step? And so there was a really big disconnect in understanding data. And so, you know, when I first came on the scene, it was really all about educating of the power of email, which I still do because it's still the highest ROI that you'll get from any marketing channel.

It's so important, but if you don't have people moving through the email, they can't generate you money, right? So then you have that traffic aspect and then you can't build your entire business on newly acquired customers because they're not as profitable. So then it's about how do we retain them?

Where do we go? How do we show up? And the only way you're going to figure out the answers to all of those questions is if you know how to read your data and take action from it. So that's sort of become the foundation. And I think when you're just starting, you don't have data, right? You just need to like show up and find people who will buy your stuff.

And it's funny because when people are just starting out, I'm like, that's the best advice I can give you is just like, go to where your customer is at. And talk to them and see if you can get them to buy your stuff. And then when you get to those really big businesses, then it's really all about how do you obviously continue to acquire, but it gets really nitty gritty in conversion optimization and that sort of stuff.

But in that middle place, you really need to just be able to read the data and make decisions from it. And so that's sort of the foundation of everything that I like to teach. And then it's figuring out, okay, if the data is telling me I have room for improvement in my email, how do I do that? If the data is telling me I have an opportunity for SEO. How do I actually implement that? And so it really does start with those numbers. And I think that's the big difference. 

Alex Bond: I totally get that in terms of the education being the foundation, because a lot of people say I need to do email marketing, do it and not really know if it's a success or not. And it kind of feels like shooting from the hip a little bit where you're kind of just like, doing what you're supposed to while kind of navigating blindly if that makes any sense.

Jessica Totillo Coster: Yeah, absolutely. And a lot of times too, you know, this happens to me too and other things, like you try something and it doesn't work and it's likely because you're doing it wrong. You know, so you may try something in your business and you're like, Oh, that doesn't work for me. But really you are probably missing out on some particular strategy or best practices.

There's no one size fits all marketing for e commerce businesses. And so the email strategy that I give to one client is going to be different than the next based on their product, their customer, the kind of business that they want to build. So I think, and this is just entrepreneurship in general is we all kind of give up a little bit too quickly.

Transitioning from the fashion and design industry to eCommerce

Alex Bond: I want to talk about your story. And a lot of that predominantly was in kind of the fashion industry, right. And kind of the design industry. And I'm interested in how that led to the e commerce world. Was that like a right place, right time thing, or did you look around and say, I don't want this anymore? How did that turn into e commerce for you?

Jessica Totillo Coster: Yeah, great question. So the majority of my background is in brick and mortar. I owned a brick and mortar boutique back in the day. I always worked for retail companies. You know, when I was going to school and studying fashion merchandising and all this stuff like Facebook, Instagram, these were not things right.

Like eCommerce was barely a thing. And really what happened was I was kind of looking around and seeing what was happening and how things were changing. And I was like, I just don't want to get left behind. So if I want to keep up and I want to, at this point, I was still about how do I create a career here?

I was like, I need to just start learning about this stuff. And so I just really started diving in and very much self taught and then was like, okay, let me go take a course in this, or let me work. Or learn from this person. Right. And so I just kind of immersed myself in it. And it was actually in my previous day job.

I started there in their marketing department for their brick and mortar stores. And they just had a, like a white label e commerce site, which is essentially just a, an affiliate site. You send traffic and you get a cut, but you don't do any of the work.

And we decided we're going to actually take e commerce in house and create a real e commerce business. And I had already worked for the company for so long and I had had some previous experience. And so for the first three years, I was the only employee of that division and I was literally running everything.

So when I tell entrepreneurs, like I know how it feels to wear all the hats. It's because I was the marketer and the social media person and the email person. And I uploaded the products and wrote the product descriptions and photos. And bought a lot of merchandise. I literally did everything. 

Alex Bond: And we're kind of figuring out as you went along, right? 

Jessica Totillo Coster: Yeah. And you know, I obviously the principles of retail and selling product are the same. It's all about what is the outcome that your customer is looking for from the product that you sell and how do you articulate that to them so that they know that it's the product for them. 

And then we did start working with some consultants and things like SEO and whatnot. So I definitely learned a ton from them. You know, I cried so much at that job. It was so overwhelming and stressful, but I wouldn't take any of it back, you know, not for a minute because doing is the best way to learn anything.

And there's so much nuance between the different businesses and. We sold a restricted product that could not be advertised on social media. And so email was a huge art and it was such an important revenue driver for us, which is really when I just started diving so deeply into that and testing so many things and learning as much as I could.

And that experience. It's really taught me like this was a business that had already been around for a really long time, right? They had a built in customer base, but it was an in person customer base. And so we struggled just as much to get those people to place orders online or, you know, to get in front of people who were not part of our local communities.

So It doesn't matter, like, what level you're at, how many smart people you have. Like, at the end of the day, it's testing, trying, optimizing, and using the data to drive your decisions. Like, everyone's doing the same. That is the baseline of running an eCommerce business. 

Alex Bond: I can totally agree. I'm interested, you were kind of working on your own under this arm, this division in the eCommerce space. When did you realize that you had more to offer? Independently as Jessica of eCommerce badassery instead of under someone else. 

Jessica Totillo Coster: This wasn't the first time I've had my own business, right? I had that brick and mortar boutique when I lived in New York, and then I decided I was over winter. So I shut the business down and then I moved across the country to Los Angeles where I live now and really kind of started over.

I had a subscription box. I did personal styling online because that was sort of my thing for a bit too. And I always knew that I wanted my own business again. I just didn't know what it was going to be. I assumed it would end up being a product based business because that's just what I've always done.

And it was that accidental. You know, the MailChimp Shopify situation and just talking to eCommerce entrepreneurs. And I think so many of us, we take our own knowledge for granted and you just kind of assume that everyone knows what you know, and that couldn't be further from the truth. So it was sort of that I know I want to do my own thing, but I don't know what it is.

And, you know, I loved what I was doing at my previous day job, but we were kind of a midsize company. So there was really only so far I could go there. And I just have a soft spot for small businesses. And it was one of those, like, I'd rather make them money than like make this corporate company money.

So it was just sort of a little bit of all of that rolling into one. It was quite the journey for sure. And I was getting ready to leave my full time job and my husband is also an entrepreneur. So I was the one with the insurance and the paycheck and the 401k and the quote unquote security. So it was a slow roll and I was getting ready to quit. And then the pandemic happened. We were like, hmm, maybe you shouldn't quit just yet. Like, let's just hold off on that.

And so I ended up working basically through September of 2020, but it really did give me the time to really hone in on what that my perfect client needed and create so many people, even if you're just starting an e commerce business, a lot of people will say, well, just jump, right? And the net will appear. Well, no, I'm like old and I have responsibilities and I needed to have a cushion and you know, it's okay to take it slow to be more intentional about what you're building.

Customer Acquisition vs. Customer Retention

Alex Bond: And so we're going to bounce around a lot for the rest of this conversation and kind of hitting all these different points.I don't want to call it a pop quiz cause you won't be graded, but that's kind of what I see in my head is kind of these, like not quick, but question and answers of just like, for example, which do you consider to be more important, customer acquisition or customer retention? And which do you think is more difficult to master?

Jessica Totillo Coster: Oh, definitely the acquisition is more difficult to master in terms of which is more important. It completely depends on where you're at in your business journey and what you sell. And I like to use extreme examples for this, right? If you sell mattresses or cars, People are only buying those ever so often.

So for you, it's always going to be about acquisition, right? And the same is true the earlier in your business, you can't create repeat business if you have no first time business. So when you're just starting out, it really is all about acquisition.

And then as you grow and you build up that customer base, then you lean more into the retention. But typically I will say never go 60 less than 60 40 in either of the directions early on. Even if your focus is acquisition, you want to make sure you have that retention game in place. Otherwise there, it's like having a leaky bucket. 

So you, when you do all the time, energy and effort that it takes to get a new customer to come and make that first purchase, oh, make sure you have the mechanism to keep them coming back and then for consumable products, it's really about retention, right? Because you have the opportunity for such a long term relationship with that customer. And so you definitely want to always lean a little bit that way. 

Alex Bond: And in regards to the retention part, while I really appreciate your example of a mattress or car, which is probably being purchased, you know, once every five to 10 years or something like that. I'm interested in how you recommend to entrepreneurs the best way to get repeat purchases for their eCommerce store.

Jessica Totillo Coster: Email, email, email, email. It is the best. It is the most profitable. It is the least expensive. It is the easiest. And I know you've probably heard things like email is dead.

And that is just not true, right? Like every couple of years, someone says email is dead, yet it continues to outperform every other marketing channel. So it's definitely not dead. There is obviously space for it's, I like to call it, it's younger, cooler cousin SMS. There is a place for that as well, which I think it's funny because the business that I used to work for, they had tried SMS years ago before I even worked there.

And I started working there, I think it was 2013. So they had tried SMS before that. They were too early. And their customers just weren't into it. And so they just had this like negative connotation with the idea of SMS and we could never get them to implement it again. Whereas now people are into it, right?

The consumer is ready. They're on board. So there's definitely room for that, but it doesn't replace email. It's a compliment to email. So that is the absolute best way. And you know, at the end of the day, What I try and remind people of is every touch point, every conversation, every interaction you have with your customer is not necessarily about getting the sample.

Sometimes it's just about being top of mind so that when the consumer is ready to buy a product like yours, you are the first person you think of, they think of, right? There's a reason why huge brands that people already know and love will Spend millions of dollars to run an ad during the Superbowl.

You already know who they are, right, but they just want to make sure that you're thinking about them. And so email, SMS, social media, retargeting ads is all accomplishing that same goal. 

Benefits of email marketing automation

Alex Bond: And you're touching on something that is wicked fascinating to me is like, why does McDonald's spend money on marketing? You know, because it is one of those things where it's like, everyone knows you. Everyone, everyone buys from you. So it's like, what's the real end goal is it's we need you quicker. You know, I may go to McDonald's this month, but their advertising makes me go there this week instead.

I like what you're touching on there, Jessica. And just to kind of stay on the email train, what's the major benefit of email automation and how can an entrepreneur actually take full advantage of that? 

Jessica Totillo Coster: Well, who doesn't like want to make money when they sleep. Raise your hand. Okay. I do. And automation allows you to do that, but what it really allows you to do, that's kind of the byproduct. What automation allows you to do is create a deeper, more personalized experience and relationship for your customer. 

So the automations are really triggered around the activity, right, that the customer takes. So whether they're coming to your website, adding something to car, you know, abandoning checkout. Or maybe they've lapsed. They haven't been around in a while. And so because they are directly tied to the customer's behavior, they're really powerful and they convert really well. Some better than others, of course.

So one of the things, if you put yourself in the shoes of the customer, and it really even speaks back to why McDonald's still advertises is consumers are Inundated with information and content and life and families and business and work, right? Your competition for their attention is not just your actual product competition. It's literally everything else. 

Alex Bond: Like another brand, is what you're saying. It's not just another brand that's competing. It's my kid, my wife, my, yeah. 

Jessica Totillo Coster: It's everything. It is everything, right? Like, If you think about the last time you drove around your town, you know, those, I don't remember what they're called, but they're like those wind flag things. But it's like the guy with the big arms. 

Alex Bond: The waving inflatable arm flailing tube men. 

Jessica Totillo Coster: Yeah, whatever those are called. Like they put them there to grab your attention and say, look at me like I'm here. Please pay attention to us. So email, especially the automation piece. You're doing that, but in response to something that the customer did, which makes it so much more impactful, right?

Like if they come to your website and they look at a product and then they leave because you know, their doorbell rang, my doorbell rings a lot. Like I didn't think people still came to the door. It's very strange.

But the phone rang or they got an Instagram notification or their kids started screaming. They got distracted and they walked away for whatever reason. It doesn't mean they don't actually want the product. It just means something else took them out of that buying experience.

And so the email now gets to bring them back, whether it's, you know, 30 minutes later, an hour later, two hours later, however you set it up. And so it really keeps them engaged with. the end goal of getting them to make a purchase. So it's pretty, pretty damn magical. 

Alex Bond: No, it is. And it's definitely sounds more like it's on the retention side of being reactive to something instead of acquisition side where it's more proactive is kind of what I'm learning today.

Jessica Totillo Coster: Yeah. The only difference would be, you know, with a welcome series is probably one of the most important email series that you can create in your business. And that really, takes that initial person and sort of holds their hands and nudges them down that path to purchase to get that first order. So that's also a part of it, but you know, you've got to get them in there first. 

The value of first impression

Alex Bond: And that's just because of the value of a good first impression, just to kind of piggyback on onto my next question, you know, is that the value of a first impression? Like, how do you essentially we're talking about competition earlier? Is it because I'm trying to make you buy from me instead of my competition? I mean, what's the real solution to being able to I don't know, differentiate yourself as a brand. 

Jessica Totillo Coster: Yeah. It's a little bit of everything really, right? Especially on the internet, if someone discovers you on Instagram or through an ad or a friend mentions you and this person comes to your website, they don't know anything about you, right?

And so this is your opportunity to. Introduce them to you, the brand, what you stand for. Look, people vote with their dollars. Okay. And this is becoming even more true as you know, the last couple of years. And so if a brand doesn't necessarily align with this person's particular values or Whatever, right?

That customer may not want to spend the money with them, but if they don't, if the customer doesn't know, they may be more hesitant to make the decision. Another example is how many of you have ordered something from a Facebook ad that never came. And then when you went to go check on your order, the website didn't even exist anymore, right?

Cause there's a lot of that madness that happens too. So Just like your competition is everything else going on in that world. person's life. You also have to overcome every poor experience that person has ever had with another brand. Cause most customers are coming to you with some sort of preconceived notion, or maybe it's the type of product you sell.

Like, yeah, well, you know, I kind of tried that before and it didn't really work. So I don't know. How do I know yours is going to work? And there's so much that we have to overcome. And that first purchase is the absolute hardest one to get. So we do have to work hard for it, but once you get it, right, the second, the third, the fourth, those all become easier and easier.

So it's a way to create the relationship, but also overcome all of those potential objections that that customer is having, because they don't trust you yet. They don't know you. They don't trust you. It's a lot different if you walk into a brick and mortar, even if it's a small boutique, if someone walks into a brick and mortar and you get to talk to a human being and you get to touch and you get to feel like the experience is so different.

And that journey of having no idea who you are and then like falling in love and trusting you, it happens a lot faster in person. It happens faster in video. Well, when you're just talking about, you know random content on the internet and a couple emails takes a little bit more work. 

Strategies for creating high-impact video content to drive customer acquisition

Alex Bond: And you mentioned it being faster on video so i'm interested in what sort of suggestions you have for creating content that will attract new customers to an eCommerce business cause that's also something that you talked about. 

Jessica Totillo Coster: Yeah absolutely so why I always tell the people that I work with, you know, not everyone needs to be the face of their brand. Absolutely. You can have a successful product business without that, but you need to have some sort of human element, some sort of personality, something that the consumer can latch onto. Because people buy with emotion and justify with logic.

And that's like a whole other rabbit hole that we can go down. But the point is, if you are willing to be the face of your brand, or you have someone on your team that can, or you can work with content creators or influencers or someone, that ramp up period from discovering you to being comfortable to buying from you is going to be quicker.

It just is. People just connect better on video, right? When you're thinking about what kind of content you're going to create for that, I want you to zoom out a little bit and you know, think about the product you sell and the reason why your customer buys it. We don't buy products for product's sake, right?

We buy them for an outcome. Either we're solving a problem. We are making ourselves feel more confident. We're buying status. That's why people buy luxury goods. So what is the reason that they're buying from you? And then what else do they care about related to the product that you sell? So an example I use all the time is CBD.

A lot of people will use CBD to overcome anxiety, to get better sleep, to reduce pain. So whichever of those that you use to market your business, What other education, what other content, what other conversations can you have with your people related to that and getting that particular outcome? It's not always about your products specifically, right?

If someone just showed up in front of you every day and said, Hey, I have this thing. Do you want to buy it? Hey, I have this thing. Do you want to buy it? Do you want to buy my thing? Like you're probably not going to buy it. But if they tell you, Hey, I know you're struggling with this problem. Here's some experience that I've had.

This is what I've done. This is what I've learned. Here's how it worked for me. Here's how it worked for, you know, my friend Jen over here. Oh, and by the way, if you want to speed up these results, try this product. Wouldn't you be more willing to buy the product that way? Right? 

So when you're thinking about the type of content you want to create, whether it's a blog post, social media, even getting started with ads, Think about how you can help the person get to where they are trying to go and then use your product just as one of those ways. If you put the service and the helpfulness ahead of everything else, the revenue that just comes in naturally. 

Providing valuable education without overwhelming information

Alex Bond: I'm extremely interested in how you determine what should be that kind of forward facing auxiliary education, right? So example that pops into my head is I really like Legos, okay? So I really like the brand.

I really like personally putting them together. And I like putting them together with my son, too. So that's something that we can kind of do together that I enjoy doing with him. I enjoy independently. He enjoys independently. 

And that's very cool to me that you look on the box and it says from three to like 99 or whatever. And I really appreciate that about them is that they're not boxing. I don't feel like I'm being infantile by like infantilized is what I'm trying to say, but by a company. Yeah, I appreciate that. 

But for example, I will. Yeah. I don't know if part of their strategy is I think that is their branding but for another person for example it could be I like star wars they make star wars legos so i'm gonna buy because I heard that way my really convoluted way of kind of using that as an example and even with your cbd one it's like.

Do you give everyone all the educational information that you can and then they latch on to one or two that speaks to them or how do you kind of determine what's the most valuable education to give to people without making them feel bombarded by information?

Jessica Totillo Coster: Amazing question. And it 100% depends on the channel that you're using. So on a channel like Instagram, right, where you can't really segment the people that are following you and you can't really target content right there, you're going to kind of do a mix of everything. And I'll talk about how you can kind of simplify that for yourself. Then on your channels like email or your blog, those are going to be really specific.

Look, a lot of businesses have more than one ideal, perfect customer, right? You're going to have multiple different customer avatars that are coming to you for a different reason. And some of these tools like your email platform, it's going to be really easy to separate those people out. And so if you are sending an email, a campaign email, right? That you're just kind of blasting to your list. That's where segmentation comes in.

So if I know, and you know, we can talk about how to get this data. I actually just did a whole podcast episode about this, but if I know that you buy this because it's something that you do to bond with your son, then I'm going to talk more about that when I send you an email, because I know that that's going to be more impactful for you. Whereas maybe someone else, maybe they use it with their grandparents, right? To like kind of bond with their grandparents.

So I'm going to speak to something different there. So when it for email, that's really easy to do for blog posts. That's also really easy to do because the goal of a blog post is to attract traffic to your website. And so you can use keywords that target all of those different uses, but let's use the, you know, creating with my son. 

Alex Bond: If you don't mind and blog posts, you're allowed to be a little more dense too, right? 

Jessica Totillo Coster: Yeah, absolutely. But what you can do, let's say for a blog post, you might want to create a piece of content that's like 10 ways to bond with your toddler son this weekend. That's a very terrible name unless someone is actually searching that, but you know, this is off the cuff. 

So keyword research, keyword research. And so you may give them some other ideas of what you guys can do together. And then one of those ways is playing with Legos. And then of course, teaching them how to put them away so you don't step on them later.

So you can kind of like, it's how you sell without being salesy, right? It's kind of like, Parents who hide vegetables in, you know, other kinds of food to get kids to eat their vegetables, right? So you're kind of hiding that salesy moment inside this other educational content. So that's a really great way to do it.

And then with something like Instagram, where you can't really target your message, that's when I recommend you create canes. So you don't have to talk about all the things all the time, right? You can just maybe carve out two weeks at a time. Maybe it's quarterly, totally depends on your business where you just kind of talk about the same thing during that time.

And here's the thing about content creation in general, whether it's content on Instagram or blogs or email or whatever, we are all so afraid to annoy people. Nobody is paying as close attention to you as you are. No one is seeing every piece of content you post or send. They just don't, you are not that important in their life.

So if it is not relevant to them, as long as it's not controversial, right? If it is not relevant to them, they are just going to glaze over it and ignore it. It's okay to speak to multiple different people. I think we just get way too hung up on this. You know, my previous day job, it was a little bit different.

There were definitely certain product categories or topics that our customer was straight up offended by. So in that case, I was sure to collect that data from them and say, Hey, you know, what do you want to hear about? 

And then if it was not on their list, I didn't send them that stuff. But that's a very unique situation. In most cases, they're just going to freaking ignore what is not relevant to them. Don't overthink it. 

Alex Bond: Most things that I check out of or unsubscribe to or say, you know, this isn't relevant is either like user generated content that is just annoying or it's cliched. It's the same type of stuff, you know, where it doesn't really have substance or value to me. And frankly, I use social media for entertainment more than anything else. I'm being totally honest. I just need to giggle every now and then.

And you're right though, is that advertisements and sponsored posts, I don't think I really unfollow any or say this isn't for me or this I don't want to see this. I either in one ear out the other or in one ear. And it kind of just sits in there for a little bit, you know? So I think there's a huge wealth in the information that you're saying right now. 

Jessica Totillo Coster: And you know, when you're talking about things like ads, I mean, you can get so targeted that you can make that ad so specific, you know, for anyone who's like worried about like Google iOS 14, like it's fine.

Marketers have kind of figured it out. The tech has figured it out. You can still target beautifully on those channels and you can just create an ad that is specific to that audience. You know, if you think about, let's like, think about TV, we'll go back to TV ads and stuff. Right now, if you're running an ad during the super bowl, that's going to be like, Pretty generic.

You're either going to make it about the Super Bowl. It's going to be funny, right? Like there's a culture of Super Bowl ads, usually either funny or going to make you cry. But when a brand is creating TV advertisements, it's very specific to where that advertisement is going to air. Right. You are not going to put the same exact commercial on every channel or sandwiched in between every single show.

It's going to be specific to the audience of that channel. And so it's the same thing when you do ads and You know, the data is there for you to utilize. So like, don't be afraid of that. Just take that little bit of extra time to create something that's going to resonate with that specific audience.

Alex Bond
Alex Bond

Meet Alex Bond—a seasoned multimedia producer with experience in television, music, podcasts, music videos, and advertising. Alex is a creative problem solver with a track record of overseeing high-quality media productions. He's a co-founder of the music production company Too Indecent, and he also hosted the podcast "Get in the Herd," which was voted "Best Local Podcast of 2020" by the Richmond Times-Dispatch in Virginia, USA.

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