🔥Controversial Email TAKES! Jay vs Jessica Best!!🔥 GUEST!! Jessica Best | Ep. 460

0:00Welcome to Do This Not That, the podcast for marketers. We share quick tips, things you can do right now, and then we add a little bit of chaos at the end of every episode. We also keep it short, like this intro. Let's check it out. We are back for Do This, Not That podcast, and we've got somebody on the show that I've been wanting to have on the show for a long time because I've listened to her speak on podcasts, all the things. She's a big deal. So who's here? We've got Jessica Best. And I want to make some sort of cheesy reference that she's the best, but I'm not going to do that because I would never be cheesy like that.

0:34But who is she? She is like it in the world of email marketing. And for more than the last 15 years, all right, she was client side, agency side, all the things, helping some of the biggest brands on the planet, like Dairy Queen and Spirit Airlines and Planet Fitness and Delta Faucet and Water.org and so many others. She has experience in the B2B side, the consumer side, nonprofit side. When it comes to email marketing, she is one of the people that knows all the secrets all this stuff she was named a 40 under 40 search engine journal said she was top 50 people that are most awesome all these things she is here we're gonna break down all things jessica welcome to the show that's one of the best intros i think i've ever had like you did your homework and i appreciate it so thank you i'm super excited to be here the homework was easy because he's done a lot of stuff um and you know before we get into we're gonna be ripping through some hot takes as relates to email marketing uh but before we do that you know a lot of people out there listening maybe they're a marketing manager or whatever they are and you've done something i think a lot of people think about but actually haven't done which is you said screw it i'm not going to work for an agency i'm not going to work on the client side i'm not going to work for someone other business i'm going to go out on my own and here it is this we just celebrated your third year anniversary going out on your own how is it going how is how did you do it what is the secret uh The secret is to bet on yourself and to be a little bit more mad about what you're doing now than scared of what you're going to do next.

2:07Truthfully, I mean, I was always happy to fly under somebody else's flag. And 2022 was a hard year for everybody. I mean, this isn't really even my old agency's fault. We were just short staff. We couldn't fill open positions. And at some point, I remember thinking even about the accounting team, like the contracts weren't getting to clients. And I was like, just let me do it. Let me do the whole thing. And so at some point I was like, instead of being afraid of those things, I didn't understand about running a business. I thought I can give it a go. Like I can at least try to figure those things out because I'm smart and I'm going to bet on myself.

2:39And the truth is I've never been happier. Don't let my old agency pals hear that. But, um, you know, if you're in a position where you're like, God, this just does not, I can't, I can't find a job. I mean, the job market right now is so brutal. Um, consider consulting, even if it's just as an interim thing to keep you fresh while you're applying for 2000 jobs a month. I have loved being my own everything. I'm the only person that can sell my time. I'm the only person that fulfills the strategy. So I never have to worry about whether somebody else's work needs checking. So I love it. I love the control that it gave me.

3:14And I wish I could say it was for some like powerful reason. Like I believed in myself. I was just mad and overworked. So it just took me believing that I could at least do as good of a job as every other tired person could do and kind of betting on myself. And so far it's worked out great. All right. Let me ask you a very real question. So it's going to sound terrible, but when somebody changes their LinkedIn and they call themselves a consultant, okay, I'm a bad person. And when I see that, I say to myself, okay, they don't have a job. They don't want to say, hi, I'm unemployed. they're calling themselves a consultant.

3:54Now, they very well may be an actual consultant. And the problem, whenever I'm talking to somebody that says, well, I'm consulting right now, that's what they say. But I'm not really able to get any of the clients or whatever. I'm looking for a full-time gig, whatever. What is it that you have to do if you're actually going to have a successful business like what you have as a consultant? How intentional and how aggressive do you need to be? How do you get clients? Yeah. That's actually the biggest thing most people are afraid of for going out on their own is keeping that pipeline full. And what I do is really project-based.

4:30So I have to keep a full pipeline pretty much all year long. Like each of my projects might take four to six weeks. Let's say I do an email marketing audit. I check out your stuff, whatever. It's like a window. Like I hang out with you for a window of time and then I got to have somebody lined up at the end of that. So admittedly, the new business piece, like fill in your own funnel is maybe the scary part. For me, I've had the benefit of I've been speaking and teaching on stages for, you know, like you said, over 15 years. So people know I might be the only like email dweeb most people in Kansas City know.

5:02So my first sort of ripple was the people in Kansas City that were like, oh, wait, you're not at my old agency anymore. I can maybe afford you now, you probably can. Let's talk. So I think picking up the phone or reconnecting with people on LinkedIn, my first ripple was just going out to the people who already knew that I was probably great at what I do. And that filled my funnel for about a year. So I would say the other thing is I am maybe like you, the word consultant makes me itchy because I think that businesses can pay a lot of money for consultants that don't say a lot. And so the word consultant is sort of poison for me.

5:40I call myself a strategist. So I will say owner and chief strategist of BetterAv when I introduce myself. Well, I do like on your LinkedIn, you make it its own company page, which it is a company and you're not calling yourself a consultant. I do think that that's a hack that anybody out there that's going out, even if you're looking for your next job, instead of just being like, I'm open to work and I'm a consultant, flip the script a little bit like what you're doing. Talking about flip the script, let's get into hot takes in the world of email marketing. Now, Jessica and I have not talked about what these hot takes are, and we probably won't agree because I don't agree with anybody about anything.

6:17So I'm curious to see, Jessica, let's hit it up. Give me a hot take in the world of email marketing that you're probably wrong about and I'm probably right about. Oh, I can't wait. Okay. First of all, I'm going to start gentle and I'm going to say resending to non-openers is crap. Oh, you're totally wrong. This is amazing. Okay. Hear me out. So I'll give you my name. Let me just bring that again so everyone understands what we're saying. Explain what you think, what that means, and then I'll tell you why you're exactly wrong. I can't wait. Okay, so resending to non-openers, when you send an email out and the campaign does okay, it gets some opens, it gets some clicks.

6:50Some of the opens are fake, whatever. And then you have automatic setup in some email platforms where you can resend that email two or three days later to those people who didn't open or click it. And my logic is those were the people who were the least interested in whatever was in your subject line or the topic of your email. So my counter offer is resend to those who opened but didn't click or those who clicked but didn't convert if you have that data. Because those were the people that you almost got but didn't make it. For me, the reminder going out to people who were like, oh, maybe that's maybe a hotter audience.

7:27All right, Jay, tell me I'm wrong. I totally disagree with you. I'll tell you why. Okay. So, uh, by the way, even though I'm disagreeing with you, you're, you're wonderful, you're smart, you're probably right, but I'll tell you why I don't agree. So you are presuming that the person cared, uh, saw your subject line, had the time to consider whether to open it or not. And they didn't, nobody's paying attention to anything. So what we do is what we suggest with all of our clients is you send out the email a hundred thousand people. Great. You got a 40 % open rate, 60 ,000 people didn't open. All right.

7:56Within 48 hours, we say send to the non-openers, But we say change the subject line to a very aggressive posture subject line that says something like, oops, you missed it. Or yikes, you scrolled past this. Or uh-oh, you don't want to miss this one. It's all the non-openers where you're hitting them in the face saying, listen, dude, you missed it and you don't want to miss this one. And the reason I believe that is you get a huge number of people opening up, right, interacting. And they signed up for a reason. They're on your list for a reason. Give them another shot. So there you go. Okay. So I love it.

8:29counterpoint because I think this is actually we're getting to something where we might actually kind of agree on something. I actually think that resending, even if you resend to the whole list, does have value. Just because somebody opened or didn't open doesn't mean that they aren't interested. Two days later, they might not have even gone through their inbox yet. So I think resending in general, like sending reminders, people are too busy. They don't remember. You aren't the best thing that happened to them today. So I think resending in general has value. I love that you're saying that you kind of redo that subject line in maybe like a more aggressive way.

9:02I will admit that for me, part of the problem with resending automatically through your email platform is two days isn't enough time. I don't think two days is enough time. And when you get into like, especially like platforms that have great A-B split tests already built in, I want the controls to spread that out. So like maybe I do a 50-50 test and then it doesn't matter. I'll know the results at the end. But an A-B test that's like the 10-10 and then send the rest, the winner to the rest of the list. Doing that after 24 hours makes me super nervous because I don't know that we have all of our data yet.

9:36You're much more sophisticated than I am. I just say, screw it. And I press send. All right, we'll hear the next hot take. Give me another hot take. That gets me to my next hot take, which is I think you can over test. Oh, okay. I could agree with this. Explain to me what you mean. So for me, we, God, 10 years ago, we used to say test with every send. That's a terrible, that's a literally terrible idea. Like you're going to drive yourself crazy. And like one in 10 tests even has statistically significant results. Or let me ask you, cause you do a ton of testing out of the bunches of tests that you do, what percent have statistically significant either lift or failure?

10:16Okay. So that's a great question because everyone calls it, you know, stat sig, which means it's statistically significant. And I know this is terrible. I kind of don't care if something is statistically significant because here's the game is that I'm trying to inch forward, right? And directionally, if I could see something or a client could see something, hey, you know what? We did this thing and it actually worked. It got us a little more juice. We got some more clients. We got some more action. Let's do more of that because I actually don't think the output of the actual statistics really matter because every day of the week is different.

10:52Your brand is different. Your offer is different. How people feel about your brand is different from one day to the next. So trying to hang on to these stats as we should do it because it does this is garbage. But I think directionally, I do believe every time you hit send, you should either be testing something or revalidating a test that did something to make sure that it actually did the thing that you thought it was going to do? Okay. So I am, I worship at the altar of statistical significance and partially because I've had clients of a lot of different sizes. I mean, you talk about if your list is a hundred thousand, you probably don't have to go calculate statistical significance often, but if your list is like 5 ,000 for some of my B2B clients or nonprofit clients, they might have small enough lists that if one more person woke up and did the thing that day, it skewed their results.

11:40So I just want to, I love your reframe of, you know, maybe we're not testing something new. We're validating something that we think we got a lift on last time. I think if you don't get statistical significance, it still could be valuable directionally, but I'm a big fan of putting that back into a split test or learning it again the second time or third time, because then you actually can kind of trust the results. It's something you can learn from. Like, I remember listening to one of your previous episodes with Daniel, where you guys were talking about we need to be able to like learn from this not just learn this specific copy worked because you're never going to use that same subject line again so i need to know whether i need to jump in here before we get into the next hot take are you a massive nerd in your real life with stats and numbers and stuff do you like go to the grocery store and say this soup is 12 times better than this, I have no idea.

12:34How in the weeds do you get with like outside of this email garbage? Okay. So I feel really called out right now because I literally just did an analysis of the cost of my groceries at Whole Foods versus the cost of the groceries at Ivy. Like I did a spreadsheet, Jay. Like this is who I am. But that's also why people hire me. You don't have to be a nerd. You just have to have access to nerds. Okay. And did we find that Whole Foods was more expensive? I'm guessing that's the outcome. do you know overall it was but on about a third of the ingredients it was actually less expensive get out of here i know see this stuff is interesting i'm not the only nerd on this phone call no no no i i i am i want to be a nerd i'm not smart enough to be a nerd okay i went into when i was in college the uh in order to be in the business school you had to be able to take calculus so i went into the journalism communication school because you didn't have to take calculus because I couldn't do it.

13:30Okay. A, I literally took calculus in high school. So you are going to hate me on this, right? But B, I actually was a journalism major too. I switched from business marketing to journalism because I felt like I could do more good by writing. Right. You did it because you actually thought it out about the major. I did it because I couldn't do math. You know, we all have our reasons. That's okay. Yeah, right. Okay, okay, okay. So I'm going to give you one more. And then I want you to give me one of yours that you get the most pushback on. Okay. I believe that there is no one right day of week or time of day to send an email and that good, ready content beats timing.

14:08I couldn't agree more. I double down, triple down on this. Send it on on Sunday. Send it out at 9 p.m. at night. Send it on a Friday. Anybody who says that this is my best day and time, immediately, that is the first thing you should be testing because that is garbage, in my opinion. Yeah. And there was always that, like, again, you've been in the business a while, like I have. We're very young and spry, but we've been doing this for a while. And for a few years, people were like, Tuesdays at 10 a.m. is the best time to send, which immediately, as soon as that was announced at a marketing conference, was the worst time to send because that's when everybody in that room scheduled their emails.

14:45It's going to vary for industry, for your list. It's going to vary for, I mean, even in automation, like if somebody literally signed up, like filled out a lead form at 9 p.m. on a Friday, I want my one-week check-in to go out at 9 p.m. on a Friday. Why is that the time of day that they were thinking about this? I think I can hit them again at that same time and have some value to them. But no marketer thinks, well, I should probably send that at 9 p.m. on a Friday. So I think letting the content and the readiness of that content or timeliness of that content guide your sense, not some perfect day of week.

15:19So on that topic, though, what do you think about this take? See, I don't believe that, let's say you send it out on Tuesday at 10 a.m. and you get your highest open rate and click-through rate. And then you send it out on Thursday at 6 p.m. You get a much lower open rate and click-through rate. And then you sit back and say, okay, Tuesday is better than that Thursday late in the day send. We should do more on Tuesday. And I think that's really wrong. And I'll tell you my two cents on it. In that different people in your database interact with your emails in different ways. So there's a population of people that interact with emails early on Tuesdays, but there's all these other people that interact with emails late in the day because that's when they're able to get to your emails.

16:00And it's not about which one had the highest, you know, aggregate open rate and click-through rate. It's in general, what is the unique audience within your database on a weekly or monthly basis that you're getting to actually engage with your emails? This idea of one day or time is better than another, I think is really misleading. Yeah. And it kind of goes back to what we were just talking about, which is, frankly, that person will get to it at whatever their perfect time is anyway. Like I know a lot of email platforms have rolled out send time optimization. Good in theory, but remember your phone's kind of opening your emails for you now.

16:35Like open rates are kind of not quite right anymore. And so for 40 or 50 % of your audience, their send time optimization, their most optimal send time is the second that you sent it out. Yeah. Oh, so that's just one of those things. I take it off of testing plans now. Testing for day of week is just not, it's not worth the salt. I'd rather test messaging. I'd rather test an offer. By the way, I think send time to optimization. So everyone out there within your platform, if you're not using it, I'm very against it. It was hot for a minute. In most platforms, I have something called send time optimization.

17:07You could flip a switch. And when you hit send on your emails, each person in your database will get that email basically at a different time, depending on what is deemed to be the best time for that person based on how they interact with emails in general, right? The reason I don't like it beyond what you just said, which is, you know, things are getting auto-open, which is making things not accurate in terms of the right send time, is it's confirmation bias in that, yeah, you open a bunch of emails at 8 a.m. on Mondays. Now all these other emails are going to show up there. So yours can perform like garbage because you're following the herd.

17:39So I think send time optimization is actually garbage. Ooh, is that your hot take? I don't know how hot it is, but sure. Okay, do you have any that like, do you have any? Yeah, I have a hot take here, you ready? Yes. I don't think, I don't care what brand you are, big, small, business, consumer, I don't think people are sending out enough email. How about that? Break my heart, why don't you? I gotta say, I disagree, but I also think that people think in how often they're sending exclusively on a calendar basis. I would rather send whatever, two a month, four a month, and then supplement that with segmented, personalized, automated supplement.

18:21I want what I send to be in some way a boost or more relevant to the recipient and not just go, I should probably send eight a month instead of four. They might get eight a month if they're in the right automated drip series, for example. But to me, just blanket at sending more with no, you know, maybe you're talking about adding segmentation to that, but with no segmentation, that just makes me cry on the inside. Well, no, I guess here's my take. My take is this is number one, it's not that you're sending out too much email and it's not working. It's that you're sending out emails that are boring people to tears and they're terrible.

18:52So I can get an email every single day. If the sender sending out great stuff, because I'm excited about it. I get angry when I'm in a meeting and they'll be like, okay, you know, our email marketing is not working. And so I'm like, I think we're sending out too much. We're annoying people. Let's send less. Okay. Because we're annoying people. That is horrendous math for your business. You're going to go out of business. It's not send less. It's send better stuff. Stop being a loser. I'll make sure to tell my clients that. Um, I think the sending, so I don't get a lot of people that say, should we send less?

19:25But I do have people say, are we over sending? And in most cases, what I ended up telling them is probably not. Um, I know that some people in the industry are like, you know, if it works, send every day. Don't do that. Because remember, every message may not be a fit for everyone on your list. So I think you and I can kind of overlap here where it's like, yeah, but if you send better stuff, and for me, that means more relevant stuff to each person on your list. Maybe you do hit send on an email every day of the week, but only this segment gets Mondays and only this segment gets Tuesdays or whatever.

19:54And you're listening to what people actually are engaging with or what they signed up for, like preferences center style. I can buy into this. I can buy into that. All right. Before we wrap up here, Jessica, everyone needs to get, hire you, consume your stuff, follow you. What has everyone got to do? How do they get involved with your world? Well, I'm pretty active on LinkedIn. That's the other tip I'd give our consultants considering pals is that I woke up on LinkedIn as soon as I went out on my own. And that's been a great way to connect with people just that have quick questions or that saw me at a conference or whatever.

20:26You can find me there or you can always find me at jessica.best. When the top level domain best became available, I was like, I'm going to get that. That's good. Jessica.best. I don't think there's a j.schwedelson. I don't think that domain exists yet, but if it does, I'm going to do it. I'm not sure I've seen that top level domain, but I believe if anybody has a right to it, it's you. Yeah, I'm on it. All right. We're going to put everything in the show. Jessica, you're incredible. Everybody go follow her, get involved with her. She's an incredible follow on LinkedIn. Thanks for being here. Thanks, Jay.

20:58It was awesome. Wait, the party is not over. Go to jayschwedelson.com because I want to do stuff with you. I want to partner with you. When you click on the button, partner with Jay, you let me know what you got going on. Work with my agency, work with me directly, get access to all of my free resources at jayschwedelson.com. And I got a book coming out this April. It's called Stupider People have done it and all of the net proceeds are going to the V Foundation for Cancer Research. Go on Amazon, buy stupider people have done it. That way you can help kick cancer's butt with me. And if this podcast wasn't the worst podcast you've ever listened to, it might have been, leave it a review, follow the show.

21:42You are awesome. Go out there and crush it.