Jay Schwedelson: We are back for Do This, NOT That! podcast. And we got somebody on the show that I've been wanting to have on the show for a long time 'cause I've listened to her speak on podcasts, all the things. She's a big deal. So who's here? We got Jessica. And I wanna make some sort of cheesy reference that she's the best, but I'm not gonna do that.

Jay Schwedelson: 'cause that's just, I would never be cheesy like that. But 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 of Planet Fitness and Delta Faucet and water.org, and so many others she has experienced in the B2B side, the consumer side, nonprofit side.

Jay Schwedelson: When it comes to email marketing, she is one of the people that knows all the secrets, all the 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.

jessica.best: 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.

Jay Schwedelson: The homework was easy 'cause 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 it 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, you've done something I think a lot of people think about but actually haven't done, which is you said, screw it. not gonna work for an agency. I'm not gonna work on the client side. I'm not gonna work for someone other business. I'm gonna go out on my own. And here it is. This, we just celebrated your third year anniversary of going out on your own. How is it going? How is, how did you do it? What is the secret?

jessica.best: Uh, the secret is to be, um, to bet on yourself and to be a little bit more mad about what you're doing now than scared of what you're gonna do next. Truthfully, I mean, I, I was always happy to fly under somebody else's flag. And, um, 2022 was a hard year for everybody. I mean, this isn't really even my old agency's fault.

jessica.best: We were just short staffed. It 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.

jessica.best: I can give it a go. Like I could at least try to figure those things out because I'm smart and I'm gonna bet on myself. And 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.

jessica.best: 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. Um, 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. Um, so I never have to worry about whether somebody else's work needs checking.

jessica.best: Um, so I, I love it. I love the control that it gave me and, and, um, I wish I could say it was for some like powerful reason. Like, I believed in myself. I was just mad and overworked. So, uh, it, it just took me believing that I could at least do. As good of a job as every other tired person could do. Um, and kind of betting on myself and so far it's worked out great.

Jay Schwedelson: All right. Let me ask you a very real question.

jessica.best: Yeah.

Jay Schwedelson: uh, this is gonna sound terrible, but when somebody changes their LinkedIn and

jessica.best: Yeah.

Jay Schwedelson: they call themselves a consultant, okay?

jessica.best: Yeah.Jay Schwedelson: 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 am unemployed. They're calling themselves. A consultant now 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,

jessica.best: Yeah.

Jay Schwedelson: but I'm not really able to get any of the clients or whatever. I'm looking for a full-time gig, whatever. is it that you have to do if you're actually going to do, be a, 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?

jessica.best: 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, so 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.

jessica.best: I check out your stuff, whatever it, it's like a window, like I hang out with you for a window of time and then I gotta have somebody lined up. At the end of that. So admittedly the new business piece, like filling your own funnel, um, 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.

jessica.best: So, um, people know I might be the only like emailed Weeb. Most people in Kansas City know. So my first sort of ripple was the people in Kansas City that were like, oh wait, you're not a, um, my old agency anymore. I can maybe afford you now. You probably can. Let's talk. So I think, um, 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.

jessica.best: Um, and that filled my funnel for about a year. So I would say the other thing is, I, I am maybe like you, the word consultant makes me it.

Jay Schwedelson: Yeah.

jessica.best: 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. Um, I call myself a strategist, so I, I will say, um, owner and chief strategist of BetterAve, when I introduce myself.

Jay Schwedelson: Well, I do like, like on your LinkedIn, you know, you make 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 turn, 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 and 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 'cause I don't agree with anybody about anything. So I'm curious to see, Jessica, let's hit it up.

Jay Schwedelson: Gimme a hot take in the world of email marketing that you are probably wrong about, and I'm probably right about.

jessica.best: Oh, I can't wait. Okay. First of all, I'm gonna start gentle and I'm gonna say resending to non openers is crap.

Jay Schwedelson: Oh, you're totally wrong. This is amazing.

jessica.best: Okay? Hear me out. So I'll give you mine and years.

Jay Schwedelson: 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.

jessica.best: 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, uh, some of the opens are fake, whatever. Um, and then you have automatic, uh, 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.

jessica.best: 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, uh, 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.

jessica.best: All right, Jay, tell me I'm wrong.

Jay Schwedelson: disagree with you. I'll tell you why. So, uh, and by the way, 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.

jessica.best: I love it.

Jay Schwedelson: pres. 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.

Jay Schwedelson: Nobody's paying attention

jessica.best: Yeah.

Jay Schwedelson: 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? Within 48 hours, we say send the non openers, but we say change the subject line to, in a very aggressive posture subject line that says something like. you miss it. Or Yikes, you scrolled past this, or, uh oh, you don't wanna miss this one. It's all the non openers where you're hitting them in the face saying, listen dude,

jessica.best: Yeah.

Jay Schwedelson: it, and you don't wanna miss this one. And the reason I believe that is you get huge number of people opening up, right?

Jay Schwedelson: Interacting, and they signed up for a reason. They're on your list for a reason. Give 'em another shot. So there you go.

jessica.best: Okay, so I love it. Counterpoint, 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.

jessica.best: 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, um, maybe like in a more aggressive way.

jessica.best: Um, I will, I 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 AB split tests already built in, I want the controls to spread that out.

jessica.best: 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 AB 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.

Jay Schwedelson: You're, you're much more sophisticated than I'm, I just say screw it and I press send.

jessica.best: Well, okay.

Jay Schwedelson: I wanna hear the next hot take. Gimme

jessica.best: I was gonna say that gets me to my next hot take, which is I think you can over test.

Jay Schwedelson: Oh, okay. I could agree with this. Explain to

jessica.best: Okay. 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 gonna drive yourself crazy and like one in 10 tests even has statistically significant results.

jessica.best: 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.

Jay Schwedelson: Okay, so that's a great question. 'cause everyone calls it, you know, stat sig, which means it's statistically significant. And I ki I know this is terrible. I kind of don't care if something is statistically significant. 'cause here's the game is that I'm trying to inch forward,

jessica.best: Yeah.

Jay Schwedelson: directionally, if I could see something or a client could see something, hey, you know what, we did this thing. It actually, uh, 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. Your brand is different, your offer is different. How people feel about your brand is different from one day to the next.

Jay Schwedelson: So trying to hang onto these stats as as we should do it because it does this as garbage. But I think directionally, I do believe every time you hit send, you should either be testing something. Or, or revalidating, uh, a test that did something to make sure that it actually did the thing that you thought it was gonna do.

jessica.best: Okay, so I am, I worship at the altar of statistical significance and partially 'cause 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.

jessica.best: So I just wanna, I, 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.

jessica.best: It's something you can, um, learn from. Like, I, I remember, um, listening to one of your previous episodes with Daniel, where you guys were talking about we need to be able to like. Learn from learn, not just learn. This specific copy worked because you're never gonna use that same subject line again. So I need to know whether this, uh, or this wording.

jessica.best: Yeah.

Jay Schwedelson: 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 how.

Jay Schwedelson: How in the weeds do you get with like outside of this email garbage?

jessica.best: 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 Hy-Vee. Like I did a spreadsheet, Jay, like this is, this is who I'm, uh, but that's also why people hire me. You don't have to be a nerd, you just have to have access to nerds.

Jay Schwedelson: Okay. And and did we find that Whole Foods was more expensive? I'm guessing that's the outcome.

jessica.best: Do you know overall it was, but on about a third of the ingredients, it was actually less expensive.

Jay Schwedelson: Get outta here.

jessica.best: I know. See, this stuff is interesting. I'm not the only nerd on this phone call.

Jay Schwedelson: No, no, no. I, I, I am, I, I wanna be a nerd. I'm not smart enough to be a nerd. Okay. I went into, when I was in college, the, uh, the, uh, in order to be in the business school, you had to be able to take calculus. So I

jessica.best: Oh.

Jay Schwedelson: the journalism communication school. 'cause you didn't have to take calculus because I couldn't do it.jessica.best: Okay. A, I literally took calculus in high school, so you are gonna hate me on this front. But BI actually was a journalism major too. I switched from business, uh, marketing to journalism because I felt like I could do more good by writing.

Jay Schwedelson: Oh, right, you did it because you actually thought it out about the major. I did it because I couldn't do math, so,

jessica.best: You know, we all have our reasons. That's okay. Okay. Okay. Okay. So I'm gonna give you one more and then I want you to gimme 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.

Jay Schwedelson: I couldn't agree more. I, I

jessica.best: Yeah.

Jay Schwedelson: down, tripled down on this. Send it on on Sunday, send it out at 9:00 PM 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 'cause that is gar bid, in my opinion.

jessica.best: Yeah, and, and there was always the, like again, you've been in the business. A while, like I have, we're very young in Spry, but we've been doing this for a while and for a few years people were like, Tuesdays at 10:00 AM 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.jessica.best: It's gonna vary for industry, for your list, it's gonna vary for, I mean, even in automation, like if somebody literally signed up, like filled out a lead form at 9:00 PM on a Friday. I want my one week check-in to go out at 9:00 PM on a Friday. Why is that the time of day that they were thinking about this?

jessica.best: I think I can hit them again at that same time and have some value to them. But no, no marketer thinks, well, I should probably send that at 9:00 PM on a Friday. So I think, um, letting the content and the readiness of that content or timeliness of that content guider sends not some perfect day of week.

Jay Schwedelson: So along on that topic though, what, what do you think about this take? See, I don't believe that, um, let's say you send it out on Tuesday at 10:00 AM and you get your highest open rate and click through rate, and then you send it out on Thursday at 6:00 PM you get a much lower open rate and click through rate, and then you sit back and say, okay, I. Tuesday is better than that. Thursday, uh, late in the day. Send, we should do more on Tuesday. And I think that's really wrong. And I'll tell you my, my 2 cents on it in that 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 interact with emails late in the day.

Jay Schwedelson: 'cause that's when they're able to get to your emails. And 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.

Jay Schwedelson: This idea of one day or time is better than another, I think is really misleading.

jessica.best: Yeah, and, 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.

jessica.best: Like open rates are kind of. Not quite right anymore. And so for 40 or 50% of your audience, their send time optimization, their, their most optimal send time is the second that you sent it out.

Jay Schwedelson: Yeah.

jessica.best: 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.

jessica.best: I'd rather test messaging. I'd rather test an offer.

Jay Schwedelson: 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. Then you have something called send time optimization. You 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 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, uh, 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. You opened a bunch of emails at 8:00 AM on Mondays now all these other emails are gonna show up there, so you're gonna, yours gonna perform like garbage because you're following the herd.

jessica.best: Yeah.

Jay Schwedelson: think send time optimization is actually garbage.

jessica.best: Ooh, is that your hot take?Jay Schwedelson: I don't know how hot it is, but Sure.

jessica.best: Okay. Do you have any that, like, do you have any

Jay Schwedelson: have a hot take for you. You ready?

jessica.best: Yes.

Jay Schwedelson: 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?

jessica.best: 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. I 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.jessica.best: They might get eight a month if they're in the right automated drip series, for example. But to me, just blanket 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.

Jay Schwedelson: Well, no, I, 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. So I can get an email every single day if the sender's sending out great stuff.

Jay Schwedelson: 'cause 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's not working. And so be 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.

Jay Schwedelson: You're gonna go outta business.

jessica.best: Yeah.

Jay Schwedelson: send less, it's send better stuff. Stop being a loser. There you

jessica.best: I'll make sure to tell my clients that. Um, I think the sending, so I, I don't get a lot of people that say should we send less? But I do have people say, are we over sending? And in most cases what I end 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.

jessica.best: Don't do that. 'cause 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.

jessica.best: And you're listening to what people actually are engaging with or what they signed up for. Like preferences, center style.Jay Schwedelson: I could buy into this. I could buy into that. Alright, before we wrap up here, uh, Jessica, everyone needs to get hire You, consume your stuff, follow you. What has everyone gotta do? How do they get involved with your world?

jessica.best: Uh, well, I'm pretty active on LinkedIn. Uh, that's the other tip I'd give our consultant considering pals, um, 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, saw me at a conference or whatever. Um, you can find me there or you can always find me at Jessica Best.

jessica.best: Uh, when the top level domain best became available, I was like, I'm gonna get that.

Jay Schwedelson: good.

jessica.best: Yeah,

Jay Schwedelson: do best. I'm, I, I need, I don't think there's a J dot schon. think that, you know, domain exists yet, but if it does, I'm gonna do it.

jessica.best: I'm not sure I've seen that top level domain, but I believe anybody has a right to it.

Jay Schwedelson: Yeah, yeah. I'm, I'm on it. All right. We're gonna put everything in the show. It's Jessica, you are incredible. Everybody go follow her, get involved with her. She's an incredible follow on LinkedIn. Thanks for being here.

jessica.best: Thanks, Jay. It was awesome.