The best brands do things differently. Jimmy Kim has taken a unique approach to growing Sendlane from obscurity to becoming one of the fastest-growing ESPs on the market. As both a former brand owner and a current tech leader, Jimmy brings a fresh perspective to DTC. He explores what he refers to as the "retention revolution," the need to rethink email strategies, and the changing landscape of DTC.

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Key topics explored:

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• The critical distinction between marketing to prospects versus customers, and understanding when to “hammer” and when to “nurture.”
• Why sending more frequent emails can counterintuitively improve deliverability and engagement.
• The growing importance of financial literacy and data-driven decision-making in the DTC space, with examples of brands excelling in this area.
• How to effectively leverage click data as a powerful feedback loop for understanding customer preferences and refining your marketing messages. Most brands think they are utilizing click data, but they aren’t.
• The benefits of an omni-channel approach and why successful brands are expanding beyond pure DTC to include retail and marketplace presence.

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Chapters:

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(00:00) Introduction

(08:14) Transition To Sendlane

(12:43) The Importance of Email & SMS Marketing

(22:40) Indicators for Rethinking Email and SMS Strategy

(26:03) Common Mistakes in Email and SMS Marketing

(29:17) Diving into ISP Levels

(30:27) Rewarming for Deliverability

(33:06) What Sendlane Offers

(37:35) What Are The Best eCommerce Brands Doing?

(42:46) The Importance of an Omni-Channel Approach

(49:11) Conclusion

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Show Notes:

• Jimmy Kim (LinkedIn) 
• Jimmy Kim (X) 
• Sendlane
• The ASOM Podcast
• True Classics
• Cuts 
• BYLT
• Jacques Spitzer (LinkedIn) 
• Raindrop
• Jimmy Sansone (LinkedIn)
• The Normal Brand

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Connect With Brett: 

• LinkedIn: https://www.linkedin.com/in/thebrettcurry/ 
• YouTube: https://www.youtube.com/@omgcommerce 
• Website: https://www.omgcommerce.com/ 

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Past guests on eCommerce Evolution include Ezra Firestone, Steve Chou, Drew Sanocki, Jacques Spitzer, Jeremy Horowitz, Ryan Moran, Sean Frank, Andrew Youderian, Ryan McKenzie, Joseph Wilkins, Cody Wittick, Miki Agrawal, Justin Brooke, Nish Samantray, Kurt Elster, John Parkes, Chris Mercer, Rabah Rahil, Bear Handlon, Trevor Crump, Frederick Vallaeys, Preston Rutherford, Anthony Mink, Bill D’Allessandro, Bryan Porter and more

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Transcript:

Jimmy:

It's not about just top line revenue, it's not about just your click rates, it's not about your revenue that you make. It's about understanding that flow and how that is ultimately driving your business and the time and energy that you're putting in to create it.

Brett:

Well, hello and welcome to another edition of the e-Commerce Evolution podcast. I'm your host, Brett Curry, CEO of OMG Commerce. And today I have the man, the myth, the legend, Jimmy Kim from Sendlane. He's the founder and CIO, Chief Innovation Officer. Just passed on the torch of CEO to someone else, which we'll hear a little bit about on the pod. But Jim and I connected at Ezra Firestones Blue Ribbon Mastermind recently. And when you're in one of those rooms and somebody walks in and everybody's just like, Ooh, I want to talk to this guy, that's what happens when Jimmy's around. Everybody wants to talk to him, be around him, things like that. And so I knew this is the guy that I need to get to know. And of course, I've heard the hype and the buzz around Sendlane. And so really excited to dive in. We're talking tension marketing, loyalty marketing, future of D two C and other fun stuff. So with that, Jimmy Kim, how's it going man? And welcome to the show.

Jimmy:

Yeah, hey man. Thanks for an introduction. Always flattering to hear these things, but yes, thank you and excited to be here today.

Brett:

Yeah, yeah, for sure. And now first things first, you are a podcaster now as well. So I know you've been a guest forever, but now you and some of your buddies, you've launched the awesome podcast, spelled a SOM. So describe what that is and why are you guys doing that?

Jimmy:

Yeah, it's a show about perspective. We recognize there's all these siloed shows, but there's not a show that kind of brings in the three elements of, to me, the three, four elements of what really is entailing in D two C and e-commerce in general, which is not just the marketer, or not just the operator, but also bringing in the agency and the SaaS that kind of thinks about it. And we talk about different topics and something like AI, for example. And we all have a different viewpoint on that because everyone thinks about how these things are applied. And what we've learned ultimately at the end of the day is everything all kind of comes back to the center where we all realize we all are achieving the same goal, but we have a different goal in mind. But it all in the principle of things ultimately is aligned. So it's been a really cool show. And yeah, it's a video first podcast. It's a little bit different and unique, but we're getting some good feedback, so we're pretty proud. Yeah,

Brett:

I was checking it out earlier and really, really great. You guys have a good chemistry, good flow and tackling, really important stuff. And I love that approach. Where, yeah, agency, which that's my background, own an agency now for going on 15 years, a little bit over D two C, brand owner, SaaS owner, all trying to solve some of the same problems and do some of the same things, but coming at it from a different vantage point, different perspective. So getting that all in one room or around one table, it's

Jimmy:

Kind of cool. That's exactly right. No, thank you for allowing us to plug that. But yeah, check us out. We're on YouTube.

Brett:

Sweet. So Jimmy, one thing I'd love to know is, and I've heard a little bit of your background, but we would love to hear a condensed version of the highlights, but when did you first realize, Hey, maybe I'm an entrepreneur? Maybe you didn't have that label or that title, but when did you know, I think I'm going to be an entrepreneur? I

Jimmy:

Think I knew I was going to be an entrepreneur really early in my life. And not to bore everyone, but I have the typical stories, the lemonade stands, the car wash business, the grass mowing business. I did anything I needed to do because at the early days it was about how do I get to my goal? And the goal was to get cash. I can buy stupid things like video games and cars and stuff. It's not that different today anymore. But really early on, that's what got me to start doing things to try to figure out how to create my own wealth and money because I couldn't work or whatever it might be. My first real business stint into entrepreneurship happened after I left the car business. I joined the internet world in 2008. So I'm a dinosaur when it comes to this world of internet. I've been around since 2008. I discovered affiliate marketing. That's actually where my roots started. I learned a little tool.

Brett:

I know many by the way. I know so many great marketers, business owners, several brand owners, agency owners, got their start in affiliate marketing. Do you have any thoughts or theories? Why does affiliate marketing breed what I consider to be a really successful class of individuals?

Jimmy:

Yeah, I think people have mistake affiliate marketers for this negative connotation, but you know what they are. They're all growth hackers, man. We're all growth hackers because we do everything unconventional, different, unique, and we have to find our way around a lot of regulation ultimately. And that's kind of where people are really scrappy problem solving. And I think that, yeah, to your point, I know a lot of great affiliate marketers now that have become so much into the world that you are surprised when you hear the background was that they were slinging eBooks or promoting Amazon products, and you're like, that's what you're doing. I mean, we talked about EZ or Firestone, that's where he came from too.

Brett:

Totally, totally. It's true. And I think, yeah, unconventional you, you've got to find opportunities and no one else is exploiting if you just do what everyone else is talking about, there's not going to be enough margin in there for you, correct affiliate marketer. And so yeah, I think that affiliate marketer mindset is pretty similar to an entrepreneur mindset, so that's great. That's great. So awesome. So

Jimmy:

Yeah, so I started there. I worked for a great guy, his name was OnX Ngal. He taught me a lot of stuff early on about the internet and things. And I quickly fell in love with email. And I started my journey in 2011, roughly starting my first business. And that started off as an affiliate marketing business. I learned all this stuff, I applied it, I started making money, and then naturally like everyone else, I became a content creator, started teaching what I was doing because I realized that made me even more money. And then where I fell into Sendlane and everything else is that I had this love with email. And one day a friend of mine hit me up and he was like, Hey, I've got this PO for $50,000 for my clothing company, for this retail purchase, and I don't have the money and the banks won't give it to me, but I have this new brand that I'm building out at my clothing store.

Can I get 50 grand? And I was doing well. So I let him borrow it, and I walked into his store just a couple months later to start talking about how we're going to get repaid back. And I looked around and I was like, man, this is cool. You produced this great basic, that's really nice. It's the unique style. Well, how are you doing online? And he looked at me and he was like, we're not doing anything online. And that was kind of the moment I was like, Hey, how about I take you online and you let me launch this thing and I become a partner of this thing instead of paying me back and let me invest some money and grow into it. And that's kind of how the brand started. So it was a men's street, it was a streetwear boutique first, and then we became a men's streetwear direct to consumer business apparel business. And in 2013 I joined it. And over the next four years, we scaled that thing to about 10 million of revenue annually. And it was quite a good learning. I didn't make any money because I learned apparel. Business sucks, and it's really hard to make margin and money

Brett:

Super hard. Yeah,

Jimmy:

You miss a season and you get screwed. There's so many things that we learned from that. And I mean, I say this and I'll probably end up in the apparel business again one day, but I say that now, I wouldn't do it because it's just so hard to make money off of it. You can grow it, but making money is hard.

Brett:

There's so much appeal or so much attraction to it because the total addressable market is huge. Everybody wears clothes, and so you can kind of carve out something interesting there. But yeah, predicting what's going to be hot, what's not, and ordering enough inventory, being able to liquidate the inventory that doesn't sell. It is a different business model. And I don't think it's, for me, man, I don't think I could get there, but I do admire those that have figured that out. It's impressive for sure.

Jimmy:

No, a hundred percent. So yeah, so I had that thing going on and I had this content creator business that eventually evolved into this software business. So when I was a content creator, I would hear from my customers the problems and struggles that they would have. So we started creating products to solve those problems, to sell to them. And it ended up becoming this great model eventually becoming a software guy. And so all of that stemmed into this need and necessity. So I mentioned earlier I was an affiliate marketer, and even today is the same problem, but back then even affiliate marketers were shunned from a lot of channels, including email. And so we said with myself and the two guys who built it said, how do we do this ourselves and stop paying someone else to do it? Why don't we pull our money together and build this thing?

And that was the first day of Sendlane, and it wasn't the business who was selling the product or the deliverability engine that we built today, but that's how it started for us. And then for four years, we used this tool internally, not as a business again, but just really just internally as a tool to make money for ourselves. And then in 2017, I had the big kind of moment. That was kind of my big moment where I exited my other two things. I sold my software company, I exited my partnership on the brand side and sold my partnership back to him as he wanted to kind of take it a different direction. And then of course, I looked at everything that I had and I said, I want to go do something. And naturally, coming off of two really good successful businesses, I was like, I could go build software now.

And that's when the day of Sendlane started. So we built that company in September of 2017, was actually the official incorporation date. And that's when we started to build what we looked into. And I know what most people will think right now is like, oh, so you wanted to build another ESP? The honest answer was no, it was never the answer to build an ESP. The problem that I saw when I was coming off the brand side was that we were using too many freaking tools. Man, if you think you're using tools now, back then it was like the backend stock app, the little widget for this, the Swatch color app we're using 30, 40 different apps. And I realized, and it's really funny, but I realized I had an issue because there was this weird app, and I don't even remember the name of it, but all I remember was $4 99 cents. And I didn't know how to contact support. I didn't know how to cancel it, and it would just keep rebuilding me. And as an entrepreneur and as a founder, it bothered the heck out of me that I was paying someone. That entrepreneur

Brett:

Was like, our stick rate is incredible. Cancel. Yeah, because you can't people, they just don't leave because

Jimmy:

Yeah, exactly. We would file chargebacks, it was a mess. Anyways, I ended up realizing that the future of what I wanted to do and how I wanted to look into the future became a unification story. And then I looked at retention because I've always loved email as a side of that and said, how do I go out and unify it? So even down to my first pitch deck was always about building the unified future. So first thing I learned was it takes really long to build software. So it took me three years to build the software almost or almost four years. And I came out launching in e-Commerce in 2021. So it took me that long and during that time, I had to sell and do whatever I needed to do, sell to whoever with this old platform. And then we launched a new one in 2021, and first one was email.

And we knew how important it was, not only because of my background, but also because just the story needed to have that base foundation built in order to go into the future. 2022, we launched SMS 2023, we launched reviews 2024 so far we launched forms and we'll continue to launch into the future into 2024 into 2025 with more channels like WhatsApp and push notifications, we'll be building a loyalty motion, a customer service motion. And ultimately the goal that I've always had on my initial pitch deck vision was how can I get all the retention touch points of a lifecycle to repeat and create the second purchase faster? Because in my clothing stores, everything was eaten up on the advertising on the first sale, and I realized that that 20 30% of those repeat purchasers, that's where my money and bread and butter was. And we needed to figure out how to get that in faster. And the faster I can bring that in, the more I could invest into the future. So that's always been the vision. It's been the vision since 2017. It's never changed. I've always wanted to build the unification story, and that's what we do today. And our typical customer today is consolidating from two, three platforms and bringing it into one platform and driving their business, having better success, better vision, better visibility, but ultimately a tool that is really building for the future of innovation of how we think about things.

Brett:

Yeah, it's really smart. I see consolidation on the agency side as well. There was a period of time back, back when you had a million different apps to do a million different things. Agencies were very specialized at that time. And now it seems like push there is for consolidation as well. I want one agency or I want fewer agencies for sure on the D two C and SaaS side, I want fewer tools to do the same thing because I can just get there faster, get results faster and that sort of thing. What are some of the tips or suggestions you would give? So getting to that second order faster, what are some of the tips from the suggestions, some of the ideas, obviously the tools going to enable you to get there faster, but what are some of the practical things that people can do to get there faster on their own?

Jimmy:

Yeah, I mean, some of the things that we see in the market, and what's funny is the thing about email has been for the last 20 years, the playbook hasn't evolved that much. We started back 20 years ago and we would do two things. We'd do newsletters and drip campaigns. So those are these weekly things we sent out. And then you would just have these automated flows. What's happened now and 20 years later is the playbook hasn't evolved that much. In fact, the data is muddier, the information is a little bit more misleading, attributions at all time high because I say everyone's attributing. So it's on a high. And the thing that comes down to it is it always has come down to core principles of what email and retention really offers. So two things happen, and I'll dig on these two things. Number one, the first thing that people don't seem to understand is a difference between a customer and a prospect.

And this is a big failure point that I see in this market because a prospect who's never purchased before is not the same goal to create a repeat purchase. The goal is to create the first purchase where the second purchase is often a different motion and skill. So separating those people's core number one like that, if you can just uncover that, you will start to unlock a lot of different things because you'll realize your prospects are not where your money's made. You need to be sending them more messages, more emails, more SMS, because you need to get'em convert or get the heck off of your list. This is like your buy or die kind of mentality. It very much lives in email especially. And the number two thing that I'm seeing in this market on why people aren't successful or they're not doing enough is actually just a simple thing of not sending enough.

And I say this in the funniest way because I think there was this core principle, again, going back 20 years, oh, if I send too many emails, my customer be bothered if I send too many emails, people do this and that. But what's changed is now if you don't send email, people forget about you now because there's so much, and not sending email does not get you brand equity. It gets you brand loss that's ultimately happening. So the second thing that I tell people quite often is if you're not emailing every day to some segment of your list, you're probably missing out on revenue dollars and brand awareness and noise. So it's an overarching theme that comes into place, especially with all the changes in deliverability and all the things that have happened, they're incentivized you to send more. All these changes that happen right now with deliverability in June, those are basically, and the people who are the least affected are the people who mail every day. The people who are most affected are the people who don't mail at all or mail very irregularly.

Brett:

It's such a good point that the paradox, so to speak, of email is actually the more you send, the better your deliverability, the lower your opt-out rates. Because yes, sometimes, and I've done this before where I've signed up for something, they never email me, they email me a month later and I'm like, wait a minute, who are they? Did I sign up for this? So it unsubscribe? Maybe I hit as well if I'm feeling real salty. But yeah, it's like I don't remember now, but if you email me regularly and you're providing value, then I'm potentially going to remain subscribed. Now I want to talk about a couple things related to that. So you talked about segmenting prospects and returning customers. How does the language change, the offers change the email strategy change in SMS strategy between prospects and customers?

Jimmy:

Absolutely. So look, a prospect, too many people are trying to build value in their emails and have focus on content. But this is why I always say I give a very simple thing. You need to hammer or push on your prospects and you need to nurture your clients. And what I mean by that is very simple. When a person is in a prospect funnel, there's only one objective to get them to make a purchase because the longer it comes from an opt-in because they're usually opting in from a newsletter, 20% off coupon, whatever that intent is, that intent is dying fast. And so your goal, obviously we've got those automated messages and things that are going out, but your goal is to get them to make that purchase and do something about it or get off. So that's a very simple focus. It means the messaging should be very clear.

Direct sale offers things to get them to convert, not content, not information that they don't care about. They haven't bought into your brand, they don't give a crap about your founder store right now. They don't care about your social media. All they care about is why they came to the product. Why did they most likely click on that social media ad and why did you hook them in? And that problem that they're trying to solve or that solution, whatever that solution is, to whatever their need is, should be the focus and we should be pushing on them aggressive. Then you flip over the customer and suddenly they're already bought in. This is where you're just building relationship and you're focusing on letting them know more about your customer. You're building advocacy, you're building loyalty within the user. And if you're going to build that, that requires a very focused message around who are you? What are you doing? You still need to showcase products. You've already identified what they've purchased. You should be able to start picking that up a little bit. Is it a men's or women's item, categorize it, whatever it might be, starting to use that information. That's where you're segmenting and you're driving more effective messaging, and that's really the best personalization you can do today in this world.

Brett:

Man, that's so good. So hammering your prospects, nurturing your existing clients. Yeah,

Jimmy:

Love your customers and push on your prospects, right?

Brett:

Yeah, and it's one of those things, I'll use an analogy and it probably isn't the best analogy, and there'll probably be some pushback for people listening, but I think the urgency is the same here. You look at some of the selling timeshares or my 22-year-old son is selling solar for residential door to door. And in both those environments, they know that if the prospect doesn't close in that meeting, they're not going to close. Correct? It's not going to happen. If they were like, well just get back to me in a week, okay, it's done. It's dead. Maybe one out of a thousand or one of a hundred, I don't know what the numbers are, but pretty much doesn't happen. And I think you got to look at your prospect list that same way they are expiring and expiring quickly. You don't get them to take action in a very finite window and it's over. You missed it, right?

Jimmy:

That's it. It's over the longer, I mean, most purchasing cycles and everyone knows their own purchasing behavior cycles around initial opt-in identity to purchase, but most of 'em are happening within the first two weeks. And once you're at a two week window, slower and slower and slower, and yes, everyone can tell me about their story, how there was 180 day person who reactivated and purchased. I get that. It's a bonus, man. It's a bonus of, it's a game of mass audience and it costs money. So you've got to try to think about that because right now, prospect is actually negative ROI until it becomes ROI, and people spend and focus most of their time in that bucket. But the moment, as I kind of gave on tip one, the moment you separate your audiences and you look at a prospect, the mind blowing thing that happens to merchants when we suggest such a simple change in the way that do nothing but send the same email, just segment them out differently so that you can at least look at how the revenue and the actions are driving their click behavior and you'll suddenly see, wow, suddenly all your money's actually coming from your customers.

Why? Because that's where actually what email marketing does plays into the picture, right? Email plays on acquisition and retention acquisition on the popup and the follow-up, but really the focus is retention. And I know the stat that people always talk about in the world is always about, oh, what's my percentage of revenue? But that's a really flawed stat too, because if you have a pop-up, for example, and people are opting into that pop-up, making a purchase, you didn't do the work. I hate to tell the retention person, but that work was done by the top of the funnel guy. You just supplied a tool to help create the thing. The thing that you need to be actually looking at is your overall store repeat rate. Your job in retention is to increase the repeat rate of the business, not of the email single channel. And this is where people lose the sight of what we call an email and SMS marketer to what I consider a retention marketer because a retention marketer, which to me is the evolution of what an email and SMS marketer is becoming. They're thinking about the inventory customer support, they're thinking about feedback, they're thinking about the overall business needs of retention and how to increase that number. That to me is the future of what email and SMS drives

Brett:

So good. And so yeah, it's not just about how do I maximize email as a channel and how do I maximize the email stats and KPIs? How do I maximize retention? And I think, honestly, Jim, I think this is a trend that we're seeing across channels and across platforms. So we do a lot with Google and YouTube and a lot with Amazon ads and stuff. And really there was a day when it was all about what's in platform roas, and then it was like, well, let's look at some third party tools, but it's still about what is Google and YouTube contributing? And that's fine, but it's really more about what is our incremental growth and what is our contribution margin and are we profitable in all of our ad spend? And then how does Google and YouTube and those things ladder up to that? And I think in a very similar vein, what you're talking about is how does email and SMS lead to more retention? And if it's not, then we've got to retool, right? Yep,

Jimmy:

That's absolutely correct. And it's retool re strategy, redo everything. It can be anything that comes into your business. It could just be, and Brett, I tell merchants this, and I mean in the nicest way it could be a product problem. People hate to admit that they have a product problem. The reason why, look, I'm going to tell you something, Brett, when you see great products, it doesn't matter if they have an email SS program that's good, bad, whatever, the repeat purchase rate is incredible. And you're like, why? Because the product is so good. It doesn't actually matter what you say. The consumer has already made up their mind that they're going to come back and make that purchase.

Brett:

Yeah, it's so true. It's so true. Marketing cannot fix a bad product for retention, marketing and fix a bad product. You may have low LTV because your product needs work. And so that's something we got to look at for sure. So if someone's looking at their business, what are some indications from your point of view that would lead someone to say, okay, I got to rethink my email and SMS strategy, I've got to retool my retention. I've got to look for the retention revolution like you guys talk about at Sendlane. What are those indicators?

Jimmy:

I think there's a lot of things that indicate, and there's no one magic bullet that comes into this place, but if I'm thinking about it at the simple thing, I'm looking at revenue that I'm generating, however I'm tracking it, right? I'm looking at the output. Are we getting, it comes into a 1, 2, 3, right? Everything is important still in the data side of things. So if we're going to get granular, the open is giving you the trend line of interest. The click is telling you how your message isn't resonating and the conversion is telling you how your product resonates through the message of interest that they've gained, right? It's a funnel. And a lot of times people only look at certain parts of the funnel and they drop off and pretend that it doesn't exist. Like an email marketer often doesn't really care what happened on the conversion of the page, but often that is the place that you need to be optimizing or you need to be working or you need to be working on the copywriting and message across both sides of that.

So to me, every one of those metric points is telling your story and understanding where the break of that story happens is where the data is useful. It's not about just top line revenue, it's not about just your click rates, it's not about your revenue that you make. It's about understanding that flow and how that is ultimately driving your business and the time and energy that you're putting in to create it. I mean, if you're using a simple thing, it should be an ROI metric email and SMS is driving 40, 60, a hundred times ROI to your tool and costs of your entire thing, not just your tool, but your agency or your marketer and having your entire team. You need to be understanding that because if it's truly going to be a big driver of business, you should be putting focus, which is where the agency recommendation always comes in for me, because most businesses shouldn't own this. In-House for example. I have a big thing about that because I believe that unless you are someone like me who's just got this obsessive love for email, go hire somebody that already knows and does things and it should be an agency because you're going to get a team wrapped around that. You know what I mean?

Brett:

Those, and I love that so much, not just because of an agency owner, and we do have a retention and email and SMSA department and a division, and we recruited a guy, kind of a top email marketer almost two years ago now to kind of build out that offering for us. And we agree there's so much that goes into it, constant need for creativity and graphic design and copywriting and then breaking down the data. And then there's both the creative side and the tedious side of email marketing that unless you've got someone that just absolutely loves it on your team, better to hire a pro. For sure.

Jimmy:

It's even simpler. Like the math, Brett, I always tell people to bath, I've got a $10 million business and three to $4 million is supposed to become from repeat purchase and retention. Why you got a $60,000 person in charge of that thing?

Brett:

Totally.

Jimmy:

Yeah. It's insanity. And even saying someone's paying 150 grand to an agency, that's still nothing to the end outcome of what that channel is supposed to produce for you. But sometimes brands are shortsighted about this and they don't think about it because they think that they're saving money or they have better control. But the reality is, and this is the other hot take on it at $10 million, honestly, it just doesn't matter. Just getting 'em a message is all that really matters.

Brett:

So good. So good. Awesome. So what are some of the other mistakes you see? So as you talked to a lot of D two C brands, you look at a lot of email accounts obviously. What are some of the other mistakes that you see? Obviously we're not sending enough, we're not segmenting our prospects from our customers. What other mistakes do you see?

Jimmy:

I mean, optimizing for the wrong metrics is always a big thing that we see. So we know the famous thing about open rates, and everybody in this market at this point knows that open rates aren't reliable. In fact, Brett, 2019, when you got a 12% open rate, that was great and somehow we're at 50, 60% and no one's questioning it. It's not because people are opening more emails, it's because there's less information. And that data is the pixel of what an open rate is, is the most rudimentary thing you can think of. You send an email, there's an invisible pixel. When it loads an image, it fires an open. That's all an open rate is, there's nothing magical about it. So optimizing wrong for the wrong rate, you should be optimizing for the click through rate because it's saying that people are seeing your message, it's relating, it's working, and they're clicking through right then it's their job on the landing page or the PDP to make the job happen.

So that's number one. The number two thing that I see is actually something I talk about a lot too, is segment and hygiene. And what I mean by that is there's an old adage of delete your old list. I'm not telling people to delete their old list. What I am telling people is to really reconsider the things that you're doing within that list and the understanding of data. Again, I talked about it, a 90 day customer who has open and active and as a customer who's made a purchase is highly valuable. But a 90 day person who is a prospect who's never purchased is very low in value. In fact, you've lost a lot of money on that person in human at this point, but people don't look at that data and really drive a decision around that. And so when I talk about this, it's like, okay, if a customer's over 30 days, and I mean if a prospect's over 30 days, great, we should still be emailing.

We should still be trying to activate, but maybe we slow 'em down, maybe we message only the hard hitting stuff towards, and maybe we just realize that they're out of cycle today and really understanding what those mean and then how to drive the hygiene of your effectiveness of your list. And so that's something that I see a lot of mistakes on. I see a lot of mistakes on too heavy of image focus. I think something that brands have forgot about is copywriting is probably more important than the actual image and words. When brands tell me direct responses, the plain text email is working so great for me, I'm like, it's not that it's working great for you, that you actually wrote copy instead of posted the picture with a 50% off sale. It's because you made someone read the words and drive the narrative to create the action.

Old school marketing, but it's 1 0 1 and people forget the 1 0 1. It's not about pretty images. It's actually about driving experience, teaching, educating, and getting someone to click on that email or SMS. And that doesn't happen through images. As always, it happens through words, which is why plain text works really well. Is it good for the brand? Absolutely not. Is it good for deliverability? Absolutely. Great because again, you're writing words against that. And then the third thing is actually deliverability. I think all the changes that have happened, it's continuing to happen right now. People are not focusing under deliverability. So I'm going to give you the one tip that everybody should be thinking about, which is simple. People look at the overarching numbers, they never dive into the second layer of numbers. You need to be diving into the ISP levels. So that means we call 'em top level domains or TLDs or ISPs, but these are like Gmail, Verizon group, Microsoft.

If you're not diving into that second layer of data and identifying what's going on there, because here's the thing, you can have a great open rate, but a really crappy delivery on a single vertical. And if it's your Gmail that's getting hurt, your revenue is down in the toilet and you can't figure out, my open rates look good, but my revenue is down. It's because your Gmail users are about six times more likely to make a purchase, spend more money than Yahoo or a OL or Hotmail. But too often we're looking too high without digging in. So deliverability is really a big driver right now, and that's changing in the market.

Brett:

Yeah, that's an area that I don't hear people talking about enough deliverability, but I would argue it's the single most important thing you can do, right? No one's going to open respond or purchase from an email they do not see that does not land in their inbox. And I think it's one of those things where a lot of the numbers mask that, to your point, that deliverability may be in the toilet and you just don't know. So how does somebody kind of dig into that and then what do they do to improve deliverability? I know there's a lot of technical things there, so we can just touch on the high point.

Jimmy:

Yeah, I mean, look, it's pretty straightforward. It's like one, obviously identification is number one. So being able to see the metrics, breaking 'em down and noticing the lack of trend. So I'll give you the trick that we think about your Gmail, your Yahoo and a OL or your Verizon, kind of our trend line. They should set the pace. They should look similar, two to six points off on your open rate and they should look similar. So that's trend line number one. The other ones will always be declining. Apple, a hot Microsoft, they'll be about half usually, and that's normal. Okay, so number one, you identify. Number two is just kind of checking through everything, the technical side, D, K, MD, mark, dude, everyone's an expert, now go hire five, Fiverr guy for $5, and he'll go do and fix your stuff if you need to or go use tools that are out there to do it or ask your ESP.

It's not that hard anymore to do this stuff. It's really easy and you need to go follow 'em and make sure that you're doing it across your entire business, not just your email stack, but your external tools you're using, your external communication you're using. All of these are important because reputation has been really big. Three, you should set up some monitoring tools. So one thing that people don't know is Google doesn't report spam rates back to an ESP. So the spam rate that you see inside tool is actually not Google, it's everything but Google. Now the data correlates with Google, so it's not too bad, but you should go install something called Google Postmaster Tools, again, completely free. Go install it. Look at your domain reputation, your spam complaints, your history, and you'll be clearly understand if something is going wrong before it's all wrong and in the toilet, which is going to lead you to number four, which is cleaning and fixing it up.

So once you've got technical, all that stuff, it really comes down to a principle of rewarming. Oftentimes the simplest fix is to stand up a new subdomain for your sending and then rewarm properly and rewarming properly is painful. It sucks, but the reality is, is that's the only way you can fix it. There is no magic hot button to just fix your deliverability if it's not a technical problem. Generally it's a volume and warming up problem that you've got to go reset up. And I saw this happen with all the changes this year between this from the start of the year to now, June. People didn't warm up after they've changed and authenticated their sending, saw their revenue tank down in toilet, not sure because they see good open rates. But then I dive in and I see that their Gmail is in the toilet, and when their Gmail is in the toilet, it's not driving revenue and results. You fix the Gmail, you start and start seeing the revenue. It's just a simple, big kind of flywheel that comes into play. So that's what I recommend without getting super deep into

Brett:

It. Love it, man. That's super, super clear and high level, very valuable. So I want to talk a little bit about features and benefits and what simlan offers because I think that there's a few things at play here. One, you entered a very competitive space. This is an industry that is rich with competitors, and it's one where there's a couple of very clear leaders, but we were talking about before we hit record that Moiz Ali, friend of mine, founder of Native, we've had the privilege at OMG of working with Native now for going on six years on the Google and YouTube side. And so I still keep in touch with Moiz, but he's kind of a D two C influencer now hosts a podcast. His tweets, her his posts on X, I guess is the way he say it now. Sometimes, man, he just calls people out on X. And so he did that recently with one of the biggest competitors in the email space and he said, Hey, I posted this a year ago on, it would've been Twitter at that time, calling you out for not having these three basic features. And guess what? It's a year later. I'm still waiting. I'm paraphrasing a little bit, but that was kind of the post, right? So a

Jimmy:

Little bit more hot taste.

Brett:

It got a lot of attention for sure. So what are some of the features that Sendlane has that you're proud of that maybe others don't?

Jimmy:

Yeah, so on that list, two of the three things that he mentions we've had for over a year. So we had those principles because not because he tweeted it, because we've already had 'em, because I've had a marketer mindset of those principles, which is where that's exactly what it was. Dynamic segmentation, everything should be real time. And I think the other thing that he talked about was why is there not a one-on-one, personalization prediction time. In fact, I get burned often right now for that because I have that, but I didn't build the old school time travel thing because I didn't believe that that worked. But everybody wants time travel, which is like localized time zone sending, right? We built something called machine learning, open optimization, which takes 50 events, open clicks, purchase behavior. We congregate a time within a 24 hour window where we believe the user will be at the top of the inbox, most active in their thing.

We use it through data. And so we built that tool a while ago and it's very successful for our users today. But it's definitely something there. There's a lot of things that our tool does different. I think that the thing that I focused on, one was this because I had the vision of unification from the early days. My product feels like it's together. It doesn't feel like we layered things on. So number one, people, the biggest difference is that it's everything you do in our platform feels the same, right? Number two, we have all these little cool features and tags. One of the things that I love is something called tags. And tags to me is this malleable tool that floats across the entire application. So we can do as simple as when you click a certain link on an email, it can tag a user for that identity of the intent that they might be giving the contextual data that they're firing back that they clicked on a men's product or whatever it might.

You can do it because they made a purchase or a web browse behavior, whatever. And then you can take those tags and fire off of those as triggers. So if they clicked on men's three hours later and they did not purchase, I could fire a men's SMS off to them and say, Hey, you looked at these men's shoes here, don't forget, go make a purchase. So we have more contextual data and we think about it. And then the third thing I think that's pretty interesting is that we're actually a pure play ESP. Again, you asked a question, why would you go into competitive? We were naive man, and when we were super naive in the early days, a I didn't know even a SendGrid existed. So what did we do? We did the most painful thing and learned how to deliver email. We built our own infrastructure.

Now, early on I was stupid, but now it's become our superpower. Not only does it allow me to pass great pricing to the user because I don't have all these cogs in my back system, but two, it's allowed me to evolutionize what deliverability is by adding more machine learning, adding more AI into it and trying to make it better and better and improve it. Right now, I'm not saying it's perfect, but we definitely have better line of sight. I can go ahead and something that I know that my competitors can't do often is I can call the head of Google, I can call the head of Yahoo. I can call them and say, Hey dude, what is going on with this customer? Why are they doing that? What can you help me and tell me and how can I drive that result for the customer? Then we bring it back down to the customer, which is something that people love, is that we have deliverability expertise at a core. We're not just a platform sitting on top of a platform. We are literally the platform. We own our own infrastructure

Brett:

Today. So good. Jimmy, you've got a unique perspective. You founded and own some brands. You were in other industries now, SaaS, founder, podcaster. What are some of the things that the best D two C brands are doing right now that others aren't? And obviously related retention is great, but just any observations you have I think would be very helpful.

Jimmy:

Yeah, I think that there's two things that I would say that I'm seeing more and more of that is happening. Number one, financial literacy. And it's not just financial, but it's also data literacy. I think that people are realizing, hey, you can make a more predictable business if you can start predicting with the data that you've got available to you, not only on the top of the funnel, but even on the retention side too. And building a business model that really is a plan shouldn't be waking up and saying, I'm going to go do 2 million this month. Top line and LED is going to pour it in there. You should model it, create goals, go after those goals and treat it more like a real business. So I see that being number one. And the number two thing that I'm seeing the best businesses do is they're using the click as more of a feedback loop, less than just a mechanism and purchase.

Lemme explain that. So again, I kind of mentioned it earlier. If I'm sitting out there and I'm sending messaging out and I'm able to start identifying what people are clicking on, what that's telling you is that this is what they're interested in. That call to action is driving that product is driving it. So for a company to start understanding who their customer is, what messaging is getting them to work and be able to drive is a really powerful thing. So one of the clients, I think you probably know him, but Ron over at Avi, for example, their brand, it's a weight loss supplement company. It was a supplement collagen company. But one of the things we did with them is they said, Hey, let's go find out who your customer is. Let's find out what they want and what they need. So this is one-on-one principle, but a lot of people skip this because they have a great product idea, but they don't realize who their audience is.

So Ron used to talk about how good health and good sleep and all these other things they didn't, and there were great real benefits to this product, but what he ultimately learned by watching what they're clicking on asking them the questions learning is that they cared about weight loss and fast weight loss look pretty simple to understand now, but when you sit back and you are the brand, it's hard for you to understand because you want to believe it does all these other things for your people and you want to push on those, get a better night's sleep with avi, right? No one cared, but it's lose weight in 28 days or whatever it might be. Everyone cared. So understanding their audience and continuing to test and understand through the data that's available instead of going out and surveying, but adding technology to be able to start identifying and learning what's working and then reapplying it into your business and strategically applying it.

So those two things are what I see in the market right now. People starting to really understand who their customers even better in having data and financial literacy. Those are the brands on the right and on the hook on the rocket right now. And true classics, for example, is a perfect company. That Ben over there, over there, dude, that man is a math finance wizard. That's what he is. Everything else, he's a great operator because he's a finance wizard and the way they operate in that business financially and data driven is so insane, but there's a reason why they're $500 million brand in four years.

Brett:

It's just crazy. Yeah, 500,000,004

Jimmy:

Years. That tells you that something though.

Brett:

T-shirts, plain T-shirts. Now Brett, their

Jimmy:

T-shirts that I used to make in 2013, they look so similar because we had created these great blanks, but we were too early, we were too naive, we didn't have it. And then you can also argue that there's cuts built and all these other ones that try to come up with them, but they've kind of kept to their core principle. If you think about true classes, you think about basics. I know they do all these other things now, but basic great shirts that are affordable, cheap, and if you throw it away, it's not a big deal because it was 20 bucks.

Brett:

But what's also cool is, and I was talking to my buddy Jacque Spitzer from Raindrop about this, that the true classics, I think they started at 12 or 13 bucks and now they're like 20 or 26, and they've continued to inch up that price because it is basically simple, but it's still a great value at 20 or 26 bucks. And yeah, they're just on fire. And I couldn't agree more with you on the finance piece. There was a time, especially during the covid boom where as clients were coming to us, they're like, Hey, just help us capitalize on growth. Just more customers. That's all we care about, make sales, right? And so we were just juicing campaigns and trying to get top line growth, but now everyone's like, Hey, you know what? Actually time out. We need a real business. We need contribution margin. We need to see what channels are actually driving incremental growth, and then where do we optimize?

How do we get medium mix modeling and get that all working? And yeah, the messaging on why someone actually buys, I think people would be surprised how often the founder is wrong. You think someone is buying because of the great night's sleep, and that's really like a third or fourth benefit. It's nice, but I'm really buying because I want weight loss. That's what moves me to make that first purchase. Maybe I stick around a little bit longer of the sleep aspect, but I'm buying because of weight loss. So you got to have that insight though to be able to lean into that messaging.

Jimmy:

And I think what you said there, I have a hot take on this that I always talk about e-commerce as the channel that it is, right? People who jump to e-commerce do it because it's the low barrier of entry, but the barrier of entry starts to increase pretty high. And there's this, I don't say that's a glass ceiling, but it's like a glass ceiling. Yeah, we're going to see the true classics of the world take off in this world, but many people will get stuck because really you can't get into distribution, retail, wholesale. This is what really matters. We tried to skip that by creating a direct to consumer business so that you can avoid those things. But really, let's be honest, the biggest brands in the world, those are the things that they nail with and you have to nail 'em. So my thing that I always talk about is e-commerce has immature market because a lot of the people started are not as business acclimated, and they haven't built a real business.

Often they're doing this because it's their first or second business, and they like this model, but eventually you get better and better, and then you realize that retail is important. Your retail takes off, your Amazon takes off your Walmart, all the distribution channel and your D two C shrinks. And if that's happening, that means that your business, you're going the right way. In my humble opinion, direct to consumer, as much as I love to hear a hundred million dollar direct, dude, that shouldn't exist. Unless you're billion dollar company, you should be leveraging a lot more of the retail side of things because that's where, to me, you build a real business of predictability and we build a business where you're not focused on the creative and the marketing and everything. You're really focused on the product and delivering a great product, selling to a great buyer who can position you on the right shelf to the right buyer in front of them and the mass audiences.

And that's to me how you build a true brand in the market versus e-commerce. And I think that's where e-commerce will always have immaturity in the market, the founders and the different people, and they do grow up, but it's always like everything else, man, Brett, the layers of growing up over time, and there'll be people that are as a Firestones room for example, and that mastermind, those people are growing up. There's plenty of the other ones that won't ever grow up past that, that will never make it into that room because they don't even understand that that education that you're learning is so important to the growth of your own business and your human mind. This is my third business. I'm still a nube man. I still consider my nube when it comes to business side of things. I may be out of the market, but then business side, I'm still learning every day.

Brett:

Totally. And we got to keep that growth mindset and that as Jeff Bezos talks about the day one mindset, it's always day one. We're always learning, we're always growing, which is really great. And I think you really nailed something that's super important. I think the best brands, the best brands that we see now are not just D two C, right? D two C is just a channel. Everyone that I see that's really growing is omnichannel or close to it. So just had a good conversation with my buddy Jimmy Sansone at the normal brand awesome clothing and apparel brand, but they've done studies where when they open a normal brand store in a market and they're in other retail outlets in that market and they're doing D two C marketing in that market, all channels go up. So don't open a normal brand store and then see other retail outlets go down in sales.

They go up in sales, and this is so true, and you layer in Amazon for those who do Amazon as well, the raising tide rises all ships. And we're doing this big YouTube push now for a pretty large outdoor brand right now. And we're seeing the same thing. We're kind of selecting different markets based on some reports we're in through Google, C-D-I-B-D-I type thing, category demand, index brand, demand index. And what we're seeing is as we're pushing hard on a market, we are seeing sell-through increase in Walmart. We're also seeing sell through increase on Amazon, and we're seeing a lift with online sales. And what's cool, what's interesting is that with these ads, we're actually pushing everybody to Walmart what they kind of wanted to do, but it's kind of wild improving everything. Yeah.

Jimmy:

You know what I always say? Here's a really big thing. I hear this story right here. This is the one story, and I hope any founder listening to this hears the story a little bit because it's important when you go to an Amazon and a Walmart and you start showing a retail, your D two C starts to come down, revenues will start dropping. But don't panic, to your point, Brett, they are going to the other channels often and they're making purchases and people don't seem to understand that. They freak out, they panic, they realize it because when you go omnichannel and you're no longer going a single channel, dude, people are humans. Man, if I'm buying something that's an edible, for example, like this thing here, if I see it at a Target and I like the brand, I'm going to buy it there instead of waiting for you to ship it to me in three to five days or I'm going to go to Amazon, I want it in four hours, right?

Look, I will buy everything and even as a D two CP moment and I try to buy it from them. But the reality is, man, the buying experience is just better. The trust is better At Amazon, for example, and as a consumer, that's where I'd like to go. And so even if I'm been buying your product, I'll still end up on Amazon to make that purchase later on because that's what just makes lend sense for me. That's my easy thing. I can buy a lot of things at once. This is why a Walmart or Target and Amazon's exist today is because consumers don't like buying a single product off a single site. They really want to go buy everything they need in one place. And I hate to tell people, but most people's products aren't products that go single store specialty unless it is a pizza oven or something like that, that has that need. But most people don't sell that kind of product,

Brett:

Right? Right. Yeah. And it's one of those things where what we see when someone goes omnichannel is direct attribution in all your D two C channels is going to look really crappy, right? Because now you're generating leads and they're going to close elsewhere. I think over time your online sales as a whole can still grow, correct? But you are directly attributed click conversions. That's going to get real messy, really muddy. And this happens a lot where some people keep different inventory on their D two C site than they have in Walmart and than they have on Amazon or whatever. And so you're going to see, okay, we do this big media push or this big push or whatever, you're going to see a different skew mix sell online than what you see on Amazon or in store, but you're 100% right as you lean into these other channels, that's when you got to just be good at business, right? Yeah. Understand business, not just the D two C tools and optimizing ad accounts and things like that.

Jimmy:

And when you look at big brands, and this is always a good learning from the big brands, when they go direct to consumer, they decide to open up, they do it for loyalty reasons, they don't do it to make more money, they do it because they know their most loyal customers will come to their site and find it. That's a whole different mindset than what people are doing today.

Brett:

And a lot of the bigger brands see, hey, the vast majority, once we reach a certain point in growth, the rest of the growth we're going to see as a brand is going to come in retail and going to come in of the channels. So really, really good. Jimmy, we can keep this going forever, man. I've got more questions I want to ask you. So that just means we're going to have to have you back and do round two at some point. But if people are listening and they're like, man, I need more Jimmy Kim in my life. I need some more of the awesome podcast, or I need to check out and see if maybe I'm going to get better results there. How can people connect with you? How can they connect with the pod and with Simlan? Yeah,

Jimmy:

So I very much found on social media on X. You can find me at Yo Jimmy Kim. I think it's on the little title thing here too. So if you're listening, it's just Y-O-J-I-M-M-Y-K-I-M. You can also find me on LinkedIn. You can search me on LinkedIn. I'm the guy wearing the hat and has a pink background there. The awesome pod is found all over any streaming service and everything you have, but we are video first, so if we always ask people, find us on YouTube, we've got plenty of shorts. If you don't want to consume an hour podcast, we got shorts, we do a lot of hot takes. It's a show on perspective, so you can find me there. And then for Sendlane side, please DM me if you need questions, but you can find our information on send lane.com. You can learn all about us. We've got a big social presence there too. So we're a little bit of everywhere and it's if you want to talk to somebody, even me and you're just starting off, please DM me. I do respond to everybody. So I tell people this and I think it's the most important thing. This is why I'm not the CEO because I want to do more of this and I want to do less of the board meetings ultimately.

Brett:

That's awesome. Jimmy Kim, ladies and gentlemen, Jimmy, thanks for bringing the Heat man and the hot takes super good and look forward to doing it again.

Jimmy:

Yeah, thanks again, Brett.

Brett:

Awesome. And as always, we'd love to hear from you. What would you like to hear more of on the show? If you found this episode helpful, please share it with somebody else that would make my day. And if you haven't done it, we'd love that review on iTunes as well. And with that, until next time, thank you for listening.

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