What’s Missing from Your Event Playbook? Jay Schwedelson Has the Answer

[00:00:00] Jay Schwedelson: No one knows what the hell they're talking about. No one's an AI expert. Anybody that calls themselves an AI expert is a clown and a loser because there's no such thing. And here's the game. You don't need to know a lot about AI. I don't know anything about AI.

[00:00:14] Alyssa Peltier: Great events, create great brands, but pulling off an event that engages, excites and connects audiences? Well, that takes a village. And we're that village. My name is Alyssa.

[00:00:26] Rachel Andrews: I'm Rachel.

[00:00:27] Felicia Asiedu: And I'm Felicia.

[00:00:28] Alyssa Peltier: And you are listening to Great Events, the podcast for all event enthusiasts, creators, and innovators in the world of events and marketing.

[00:00:37] Rachel Andrews: What is up in the wide wild world of events, my name is Rachel and you're listening to the Great Events podcast. I am going to do my best today to channel my inner Jason Kelce for his epic intro. So get ready with me, get in the right mindset, because we have a very, very great guest today on our podcast. So ladies and gentlemen, strap in and turn up the volume and get ready, because today's guest is an absolute legend in the marketing game. He's the founder of SubjectLine.com, the go-to spot for anyone who wants their emails opened. He's the president and CEO of Outcome Media, leading the charge for next level marketing. He is the powerhouse behind GURU Media Hub delivering insights that marketing can't get enough of.

And then I think probably a lie, he's running the number one marketing podcast in the world. I'm pretty sure it's North America, but we'll take it. But who's arguing with me, right? I guess you could Google it. Give it up for the man, the myth, and the inbox icon, Jay Schwedelson, welcome.

[00:01:40] Jay Schwedelson: I'm fired up to be here. I listen to this podcast. It's a great podcast. It was a great intro. None of it is true, but beyond that, you are awesome. This is awesome. We're going to have fun. 

[00:01:50] Rachel Andrews: I'm pumped. We're doing like a doubleheader guest speaking on each other's podcast, but I'm excited. Different content for both, but we are here fired up and we look ridiculous. Can we talk about that?

[00:02:00] Jay Schwedelson: Yes. So Rachel hit me up and she goes, "Okay. It's going to be, this is right around Halloween. Let's wear costumes." And so I said, "For real?"

And then she messages me last night,this is what I'm wearing. And she sends me a ridiculous costume and I didn't have one. So I learned that I could go on Uber Eats and I Uber Eated a banana, so I'm a giant banana right now, and I'm as excited as I've ever been to be a banana. And you look amazing.

[00:02:26] Rachel Andrews: I'm Wonder Woman. Hey, I'm wearing a cape, everybody. You Can't see it on Zoom, but whatevs, you know. Well, I guess we should say do this, wear the banana over Uber Eats. Maybe not this costume, but I don't know who's the bigger loser. I have this on hand. You ordered that on Uber Eats. You decide.

[00:02:47] Jay Schwedelson: That's a good question. Yeah, you own that, so good for you.

[00:02:50] Rachel Andrews: Oh my God. Well, we're going to dig right into it. We don't want this podcast to be forever because people probably don't want to listen to us for a million years. Who knows? Maybe they do. You have a lot of followers. They must love you.

[00:02:59] Jay Schwedelson: Nobody wants to hear us. They already want it to end. They're like, "Oh no."

[00:03:02] Rachel Andrews: They want to hear from a giant banana and a Wonder Woman. Right?

[00:03:05] Jay Schwedelson: There you go. Yes.

[00:03:06] Rachel Andrews: Let's dive right in. Let's talk about all the things that you're working on. I mean, obviously, you have been in the marketing space for a long time. You're doing a lot more with events now. This is a Great Events podcast. So let's talk about events. You're doing some funky things. Tell us all the things you're doing on the event side.

[00:03:23] Jay Schwedelson: So this past year we launched, my media business launched a new event called Eventastic. It's the first time we put on this event, and we didn't know anything really about the whole event world, but we said, "Screw it." And we said, "We think that the event world, people that are event professionals, whatever, they need a virtual event that doesn't suck."

And so we started Eventastic and we didn't know what we were doing. It was this past few months ago, and it turned out great. We had like 13,000 people there and it became bonkers. We did all these weird activations. We had a huge show up rate, and I made a lot of new friends in the event space, and I realized that event people, A) are really nice, and B) there's a huge appetite for looking at events differently. So that got me excited, so we're doubling down, more events about events and all of that.

[00:04:09] Rachel Andrews: Okay, I love events about events. I also love that you're just doing... You're like, "You know what? Let's just think of any crazy idea we could possibly think of."

Maybe we ask everybody to wear a banana costume at the next fricking virtual event and say, "Everybody, we're all bananas." I mean, I'm sure anyone would follow you into the fire doing that.

[00:04:26] Jay Schwedelson: Well, I will tell you, we try to do any, like you said, we actually have a meeting,a standing meeting called, Does this Suck? And what we do is everyone comes to the meeting with ideas and any person in the meeting has veto power. There's about nine of us in the meeting. And if one person says it sucks, then we don't do it. But everyone brings the craziest ideas. So things like we've had Joey Chestnut at our virtual events eating spam against people. We've had live skydivers. We've had Debbie Gibson from the 80's singing karaoke against us. So we've done anything we possibly can, but on an event level, as an event professional, we also do things like we don't do on-demand. We do what we call earned on-demand where if you don't show up for an hour, you don't get the on-demand link because I think so much crap in the event industry is a Ctrl+C/Ctrl+V, we just copy and paste and do the same thing over and over again, and that's a recipe for failure. So we try not to follow any playbook and just go with that.

[00:05:16] Rachel Andrews: Yeah, I'm a big fan of testing, breaking things, begging for forgiveness later. It's probably easier at a smaller company than a bigger company, because a lot of people are really afraid to fail. I just wish people were less afraid to fail, because that's the way you learn, right?

[00:05:32] Jay Schwedelson: Listen, not only are you not going to get anything out of not testing new things, but the other big mistake is testing things that are too small. Like, "Okay, at the expo hall, let's have this weird little networking spot over here."

And that's our big new test. Really? That's not going to do anything. When you're out there and you're testing things, you have to test significant things or else you're not going to see a significant change.

So I agree with you a hundred percent. Every time you're doing an event, every time you're doing anything, if there's not a significant test component, even if you're just pressing send on one email to promote your event, if you're not testing something significant, you're wasting the time and exposure and effort of that motion.

[00:06:09] Rachel Andrews: You kind of touched on this, but talking about why safe equals boring. You're talking about testing things. What could you tell event profs about getting the confidence to test things? I think that we are just so busy as event pros, like either on the marketing side, event marketing side, or on the logistics side. We're just busy. And so we always try to, I want to infuse things into my events. Sometimes we just don't have the time to, but I don't think some ideas don't have to take a lot of time.

[00:06:36] Jay Schwedelson: A hundred percent. And the problem is everyone's checking boxes. "Okay, we have to get out these social posts on our company page. We have to get these emails out about early bird to check the box." And what we are doing is we're just trying to get it done. It's not actually going to move the dial. And it's not only is it a waste of time, but it's a negative signal, because when you don't get a response to something that you do, it's not just, "Oh, we didn't get a response." It's the person that you're marketing to try to get them to do the thing is looking at it and say, "Oh, this is generic, this is wallpaper, this is just like everything else. I'm going to ignore this."

Not only now, but subconsciously, every time you then go after them again. So you're creating a negative signal by checking boxes. You're better off doing less stuff, but doing it more awesome and changing things up and not using the same templates that everybody is using and not going to Canva and downloading the same garbage and doing the same. "Oh, our agenda's live and we have early bird and the hotel discount rate."

And you're following the same stupid thing you did last year. You need to do things differently or else the outcome is not going to be any different.

[00:07:38] Rachel Andrews: Right. Holy snoozefest, right? 

You follow the same methodical thing and everyone knows it. And I'm probably guilty of that too. We're trying to go out there and crowdsource more. We know people are getting so sick of the same shit. And so it's like literally everybody, every single leader I talk to. What's the number one thing on their event survey, from their post-event survey? More networking. More networking.

Nobody wants to be talked at, talked to for eight hours a day, but then people can't figure out the best way to network at these events, because they just gravitate towards just drinking or whatever. And we got to think of new ways for people to engage with each other

in a more meaningful way. That's what I want to test more of.I love your obsession with the Guinness World Records and just doing stuff around that. That's cool. When you bring together people, you're creating this connection. What else can you do together? Right?

[00:08:32] Jay Schwedelson: Always. And it doesn't have to be something crazy. So one of our events, our GURU Conference is about email marketing, we have a theme every year. So the theme this year is 90s versus 2000s. And people are like, "Why do you have a theme? It's about email marketing."

Because at the end of the day, we're human beings and the way you connect to other human beings, it's not just talking about, "Hi, what are you putting in your subject line?"

But it's what are you interested in, or what's a funny thing, or what's whatever.

So we do things like let's make a deal where we go on camera and say, "Okay, the first person that has a Blockbuster card from the 1990s, you come on screen, you're going to win this, that, or whatever."

And now, there's people all virtually racing all around their house, looking for this piece of garbage. And all of a sudden, you're connecting with people and it's creating these moments that you remember. You're not going to remember the tactic that you learned about the subject line,

but you might remember that rando who found their Blockbuster card and it had gum on it. You're like, "That was amazing." You need to create memorable moments.

[00:09:25] Rachel Andrews: Blink twice if you're okay. Are you in a hoarding situation?

[00:09:29] Jay Schwedelson: Exactly right. First of all, if you have a Blockbuster card,

I'm judging you aggressively. That's weird. I mean, meanwhile, I probably have one somewhere,

but that's what I'm saying. And just creating humanity, and I love networking. And also when you think about the content at these conferences in-person, I mean panels and these horrible things that we follow, these playbooks and these boring, horrendous speakers, just stop it. Stop following the worst playbooks of all time.

[00:09:55] Rachel Andrews: Let's get into AI because I've listened to a bunch of your podcasts about AI, and I love… First of all, I loved your post about being mean to AI. It was freaking hilarious. The fact that it's not about being mean, it's just about being direct and asking what you actually really need and redefining that. Talk to me about it because I feel like every single second of every day a new thing is coming out. How do you stay on top of it? What are your favorite things? Tell me all the things.

[00:10:21] Jay Schwedelson: So I think the biggest problem with AI is

I hate this thing where people say, "AI is going to take your job," or some garbage like that. It's the most ridiculous thing of all time. But what's really happening is it's creating this fear that me as an individual, I don't know enough about AI. There's all these tools, I can't keep up with it. Everybody else seems to know all this stuff and I don't. And you almost punt on it, like, "Screw it, I can't keep up."

But here's the secret. No one knows what the hell they're talking about. No one's an AI expert. Anybody that calls themselves an AI expert is a clown and a loser because there's no such thing. And here's the game. You don't need to know a lot about AI. I don't know anything about AI.

So here's what I do. I go to ChatGPT. And anytime I need something, I ask ChatGPT, "How the hell do I do this?"

Let's say I'm trying to optimize my website for AEO, answer engine optimization. Everyone's done with SEO and now we got to make sure our website is all set up for the AI LLMs and the whatever to pick up on stuff. I don't know how to make my website show up in ChatGPT. So I go to ChatGPT and say, "Hey, ChatGPT, here's my URL. What do I got to do to my website to make it show up when people ask you questions?"

And then it tells you exactly what to do, you don't need to be an expert. What you need to do is not be scared about the fact that you think you're supposed to know garbage. Nobody knows what they're talking about. Everyone is just making stuff up.

I put this stat up on my LinkedIn the other day, because it made me want to break something where, do you realize there's 750,000 profiles on LinkedIn where people list themselves as visionaries? Those people are losers. Okay? There's like four visionaries and half of them are dead. You know who's a visionary, whoever just lost their job and they're trying to say that they're important, that's who a visionary is. Get out of here. Don't listen to anybody. Everyone's clueless, including me.

[00:12:05] Rachel Andrews: I love it. I love it. And I feel like I was talking to someone recently at an event and they were like, "I know exactly when it's AI speaking versus a human."

You could tell with the, what is it, the em dash? What's it called?

[00:12:16] Jay Schwedelson: Yeah, the em dash, a hundred percent. Yeah, ChatGPT, actually, there's a stat, and this is real, ChatGPT will tell you this. If you go to ChatGPT and ask it for to write a social post or email copy, roughly 50% of all of what it gives you back will include at least one em dash. And that is the tell. And now when we see it, we're like, "That's not a human. This is garbage."

[00:12:39] Rachel Andrews: I'm actually personally victimized by this, because I love dashing when I speak. And now I can't do that anymore without people thinking it's AI.

[00:12:48] Jay Schwedelson: So you're a bot.

[00:12:49] Rachel Andrews: I am a bot. Welcome to the podcast. Yeah, exactly.

[00:12:54] Jay Schwedelson: We're not real. Yes.

[00:12:54] Rachel Andrews: I love it.

[00:12:55] Jay Schwedelson: I know, it's sad.

[00:12:56] Rachel Andrews: Tell me, kind of, unlimited money… You're already kind of doing this with your events. I feel like this is an easy layup for you, but if you had unlimited money, what event would you create?

[00:13:07] Jay Schwedelson: Oh, well, if it was unlimited, first of all, I'd do an unlimited in-person event, that would be the bomb.com. But really unlimited money? This is ridiculous. I think that what I would do is, first of all, I'd have 100 different rooms and every room would be some sort of weird, immersive, out of control situation. And then everybody would get a celebrity buddy and it would rotate. How cool would that be? Like, "Okay, you're paired up with Lance Bass from NSYNC for the first half of the conference. And then the second half of the conference you get to hang out with, I don't know, like Shaquille O'Neal or something." And you just get paired up with different celebrities, you hang out with them and that would be amazing, but that's not very realistic.

But even without unlimited money, you can get creative. So we did one of our events, we did the Hot Wings Challenge, and we went on Amazon and you could buy the hot wing sauce or the same one from the show and it cost like 20 bucks. And we bought the hottest ones possible, and we had a group of marketers live, do it live. And I did it and it didn't cost a lot of money. And then I didn't know that you're supposed to put a dot of the sauce. So I went really heavy with the sauce, and that night I thought I was going to die. I lost an incredible amount of weight, so I didn't need Ozempic, but it was like an experience and a half, so you don't need a lot of money, you just need a lot of stupidity.

[00:14:23] Rachel Andrews: You hear that folks, GLP-1's out, Hot One's sauce is in.

[00:14:28] Jay Schwedelson: That's it. That's all you need. Take a shot every day.

[00:14:31] Rachel Andrews: Oh my God. Well, I have to say I love following you on LinkedIn of just your no BS posts and just cutting through the bullshit. What prompted you to do that? Were you just sick of all the crap that people were doing? I mean, that's probably why you started your company, right?

[00:14:47] Jay Schwedelson: Well, that's actually a good question. So I'll tell you. Here's the true story of what happened. So back during COVID, so I have this demand gen agency and I've had it forever. It's about a 100-person company. And during COVID, I thought I was going to go out of business because all the marketing budgets were going away and I had this payroll and I didn't want to fire anybody. I didn't want to furlough anybody. And I'm like, "I'm going to legit go out of business."

And at the time, I think I had 600 connections on LinkedIn. I had never posted really. And I said, "If I'm going to stay in business, I got to meet a billion more people and then maybe I'll get more business."

So that day, I started posting on LinkedIn anything I could think of. And then it's the same day

I launched this GURU Conference. I'm like, "I'm going to put on a virtual conference to try to meet a lot of people." And that's what happened. I started doing it.

Thankfully, my agency stayed alive. Hooray, I get to eat dinner. But then I realized quickly like, "Oh my God, people gravitate towards somebody actually just being a regular human."

And it's super uncomfortable because in my regular life, I haven't posted on Facebook in like 12 years and I judge people who do post a lot on Facebook. But in my business life, the more you act like a human, the more you actually can do fun stuff, interact, meet. Look at us, we met because of LinkedIn and you get to meet and interact and do cool stuff. So that was a long answer to your question, but that's how I started with all that crap. But you're the same way, you're a very real human being.

[00:16:03] Rachel Andrews: I try to be. I don't think being super corporatey is the best for me. I've always found that I do better business, have better partnerships, do well with my co-workers just by being real. And that doesn't mean I'm not appropriate,

I just feel like that's just the way I operate in life. Can't change who I am, sorry.

[00:16:26] Jay Schwedelson: No, I love it. Look, we're sitting here as one woman and a banana, and that was by you setting this up, so I believe what you're saying that, that's actually how you function.

[00:16:34] Rachel Andrews: If we're launching this October 29th and it's my favorite holiday of the year, Halloween, you would definitely be invited to my Halloween party. There's a costume contest, all the things, so it's on Halloween. It's like the first time Halloween has been on a Friday in a long time.

[00:16:49] Jay Schwedelson: I know, this is going to be a disaster though.

[00:16:51] Rachel Andrews: Yeah. I mean, the cities will burn down. I don't even know. So last kind of question for you, the do this, do that.

[00:17:00] Jay Schwedelson: Do This, Not That.

[00:17:01] Rachel Andrews: Do This, Not That. Oh my God, I can't even plug your podcast right.

[00:17:03] Jay Schwedelson: Not this, do that.

[00:17:05] Rachel Andrews: Do this, don't do that. What is it? Say it again.

[00:17:08] Jay Schwedelson: Do This, Not That.

[00:17:09] Rachel Andrews: Do This, Not That. It's only the number one podcast in the world for marketers.

[00:17:13] Jay Schwedelson: Oh, yeah, big time.

[00:17:14] Rachel Andrews: I love that you keep going up in the rankings. It's just because you wear banana suits and stuff. It's great. Maybe I'll switch my tactics here. On that podcast, what are some of your favorite kind of "do this not thats" that you've gotten? Maybe top two or three.

[00:17:30] Jay Schwedelson: Work-wise, or life-wise?

[00:17:31] Rachel Andrews: No, whatever. Just anything.

[00:17:33] Jay Schwedelson: Okay. Well, so on my podcast, what we always try to do is we do a serious part of the beginning, like marketing stuff and then we do stupid stuff at the end. So the stupid stuff at the end, I will tell you that I think it's really important to not talk to people that you sit next to on a plane because that annoys the hell out of me.

My go-to move there, which I just talked about on the podcast, is that I just tell the person next to me instantly when we sit down, if they say, "Hello, what's your story?" I go, "Hello, I'm not a talker." And then I don't look at them again. And so that's my go-to move for that tip.

And then in terms of actual marketing tip, and this really works well, whether you're promoting an event or anything like that. I'll tell you my number one subject line tip is that the sooner you tell somebody who they are in the subject line, the faster it is they want to engage.

What do I mean by that? So if you put—forget about putting

'Jay, check out our event!'

That is ridiculous. That's 1984. What you want to do though is tell the person who they are, their job function, their company size, their industry, whatever it may be. So for example, it could be this is great for HR leaders, this is great for small businesses that are growing. This is perfect for business owners in Miami, whatever it is, the person is that we so often target an audience, but we don't tell the audience who they are. If you tell the audience by their function, you could put their company name in the subject line, you could put their company size, you could put their geography, their interest. The sooner you do that, radically changes the number of people that want to engage with your email, so that was my boring tactic.

[00:18:54] Rachel Andrews: I love it. No, it's like direct it right at the persona, like say it. Call it out.

[00:18:58] Jay Schwedelson: Yes, say it.

[00:18:59] Rachel Andrews: I love it. Well, thanks so much for joining the Great Events podcast. Anything else you want to share with our listeners? Maybe a plug for the upcoming event?

[00:19:07] Jay Schwedelson: Yeah, so our free virtual event, it is wild, GURU Conference, it's guruconference.com. We have Nicole Kidman that's going to be there. Lance Bass is going to be there. Flavor Flav is going to be there. And we just added Nick Lachey judging a karaoke contest is going to be there. So you want to check it out at the world's largest email marketing event. I appreciate you having me on. You are awesome. You rock.

[00:19:27] Rachel Andrews: I love it. Thanks so much for joining. Our listeners really loved it. I know they did. We'll probably get great feedback. Hopefully. You're the best, the best banana I've ever interviewed.

[00:19:37] Jay Schwedelson: Oh, so nice. So nice. Thank you.

[00:19:41] Rachel Andrews: Thanks to our listeners for joining Great Events and we'll see you next time.

[00:19:47] Alyssa Peltier: Thanks for hanging out with us on Great Events, a podcast by Cvent. If you've been enjoying our podcast, make sure to hit that subscribe button so you never miss an episode.

[00:19:57] Rachel Andrews: And you can help fellow event professionals and marketers just like you discover

Great Events by leaving us a rating on Apple, Spotify, or your preferred podcast platform.

[00:20:07] Felicia Asiedu: Stay connected with us on social media for behind-the-scenes content, updates, and some extra doses of inspiration.

[00:20:14] Rachel Andrews: Got a great story or an event to share? We want to hear from you. Find us on LinkedIn, send us a DM or drop us a note at greatevents@cvent.com.

[00:20:24] Felicia Asiedu: Big thanks to our amazing listeners, our guest speakers, and the incredible team behind-the-scenes. Remember, every great event begins with great people.

[00:20:34] Alyssa Peltier: And that's a wrap. Keep creating, keep innovating, and keep joining us as we redefine how to make events great.