Sullivan Finlay is a comedian and content creator who transformed years of corporate experience into one of social media’s most recognizable voices on workplace culture. After careers in accounting and enterprise software, Sullivan now creates comedy that captures the quirks of modern business while helping brands understand what truly connects with online audiences. In this conversation with Zack Oates, he shares practical lessons for restaurant operators looking to build stronger content and deeper engagement.

Consistency Before Virality (08:18)

“I didn’t have anything go viral until like seven months after I first posted.”

Sullivan explains why successful creators often publish hundreds of pieces of content before finding meaningful traction and why consistency matters more than immediate results.

Authenticity Creates Better Content (09:15)

“People are looking for that authenticity.”

As AI-generated content becomes more common, Sullivan believes genuine human stories and lived experiences are becoming even more valuable for brands.

Why Relatable Content Wins (08:51)

“Truth in comedy.”

Sullivan discusses how the most successful content comes from experiences audiences immediately recognize, making relatability one of the strongest drivers of engagement.

Building Better Social Media Hooks (15:27)

“People want to see the second thing.”

From watch time to content structure, Sullivan shares practical techniques creators use to keep viewers engaged through the end of a video.

Collaboration Expands Your Audience (10:16)

“Let’s expose each other to each other’s audiences.”

Sullivan explains why collaborating with other creators helps brands reach new audiences while creating more engaging content.

Who Deserves an Ovation?

Unlike most episodes, Zack asks Sullivan to recommend comedians and creators he enjoys following rather than a restaurant industry leader. Sullivan highlights creators including Will Angus (Almost Friday), Kylie Brakeman, Jeremy Culhane, and the Artist on Artist on Artists on Artists podcast as standout voices in comedy.

Links:

https://www.instagram.com/sullyfinlay/?hl=en

https://www.tiktok.com/@sullyfinlay

https://www.youtube.com/@sullyfinlay

https://www.linkedin.com/in/sullivanfinlay/

https://sullyfinlay.com/

Transcript

00:00:00:12 – 00:00:25:04

Zack Oates

Welcome to another edition of Give an Ovation, the Restaurant Guest Experience podcast, I’m your host, Zack Oates and each week, I chat with industry experts to uncover their strategies and tactics to help you create a five star guest experience. This podcast is powered by ovation, the AI feedback and operations platform built for multi-unit restaurants. Learn what’s actually happening in your restaurants and exactly how to improve while driving revenue.

00:00:25:05 – 00:00:48:08

Zack Oates

Learn more at ovation. And today, we have a most unconventional yet most inspiring guest, Sally Finley. He is someone that if you haven’t checked him out. Actually, I’m probably sure if you are an Instagram or TikTok, you have seen him. He’s an influencer with hundreds of thousands of followers. He is a recovering CPA. He’s now a full time comedian.

00:00:48:08 – 00:01:10:00

Zack Oates

He’s worked with brands like Delta, Salesforce, LinkedIn, Old Spice, Gillette and I love that. He’s got this basically mocking capitalistic tropes. And I think it’s just so funny. And the way that I think of is, if you have not seen him yet, is he’s like created the TikTok version of Dilbert for the new generation without the controversy of the creator.

00:01:10:00 – 00:01:30:01

Zack Oates

And I think it’s been amazing to watch. But I gotta say, Finley, I, you know, sometimes don’t always appreciate how you portray CEOs in the space. And I think it’s a it might be a little bit to, you know, do characterization, but there is a lot of synergies if you really think about it. But yeah. So let’s circle back on that later on.

00:01:30:02 – 00:01:34:18

Zack Oates

Yeah. Anyway well welcome to the podcast Sally.

00:01:34:20 – 00:01:42:11

Sullivan Finlay

Thank you. Thank you for such a nice words. I’m honored to be compared to Dilbert. So.

00:01:42:13 – 00:01:51:15

Zack Oates

Well, by the way, I saw your face when I started making when I started, like, coming down on you, you’re like, oh, my gosh, is this, like, a totally hit piece? Like, is that why he had to go to this podcast? Is this.

00:01:51:16 – 00:01:56:23

Sullivan Finlay

Here we go. Total hit job for 45 minutes. Yeah.

00:01:57:00 – 00:02:17:22

Zack Oates

Okay. So, Sally, tell me about this journey. Because you were CPA, you worked at Salesforce, you’ve worked at some of these big companies, and then you went full time into comedy. And I’m sure that, like, your parents were like, oh my gosh, what’s happening? But be supportive. Like, how did you make that transition and what was that like?

00:02:17:24 – 00:02:36:17

Sullivan Finlay

Yeah, I mean, it was tough. Had kind of started doing comedy in 2020 when, you know, nothing else going on. And I was still in county at the time. I started doing content in 2021. So before that I was doing like improv and sketch and all that and just wanted another outlet to do characters and things I did on stage.

00:02:36:18 – 00:02:42:11

Zack Oates

Wait, by the way, had you done this all in school or like, had you been acting in school or college or anything? Nothing?

00:02:42:11 – 00:03:05:05

Sullivan Finlay

No. To be honest, I’m also very stereotypical accountant and that I was probably too socially anxious to do like theater or improv or anything in school. And then eventually I was like, I had a friend who was just like, hey, let’s do this improv class. And like, sure, why not? And then he bailed. Last second. I am suddenly a midwestern accountant in an improv class, and the rest is history, I guess.

00:03:05:05 – 00:03:25:05

Sullivan Finlay

But yeah, so had done content for a few years before going full time with it again. Very stereotypical accountant, very risk averse. Like, should I even do this full time? And thankfully my wife is a very good support and was like, yes, you should do this. You will regret it if you don’t. And yeah, it’s been a couple of years of doing it full time, which is great.

00:03:25:06 – 00:03:26:07

Sullivan Finlay

I’m so glad it.

00:03:26:08 – 00:03:46:01

Zack Oates

What’s your process for coming up with content? Because you come up with some funny stuff, man. And I told you before we hit record, we share your stuff at ovation. I mean, we’ve shared it for like the last few years because it just is so spot on. It’s like Silicon Valley, except like today. Like, it’s just it’s so real.

00:03:46:02 – 00:03:48:02

Zack Oates

How do you come up with that stuff?

00:03:48:04 – 00:04:04:19

Sullivan Finlay

Thanks. Yeah, I think a lot of it is, I’ll have to say, training, like coming out through like Second City, UCB, a lot of these schools that are really good at teaching comedy. When I was doing more of that, I think has just enabled me to have like a writing process. I’m a little weird. This is getting very in the weeds.

00:04:04:19 – 00:04:20:08

Sullivan Finlay

But coming from an improv background where to write, I will have to talk. Like I’ll have to improvise something interesting to hear it, and then I can write it down and like the jokes come. But yeah, it’s truly just writing, writing and writing as much as I can trying to do that. Like.

00:04:20:09 – 00:04:27:07

Zack Oates

Would you be like, turn on your camera and then just like start talking to the phone and then be like, oh, that one. That was pretty good.

00:04:27:09 – 00:04:45:24

Sullivan Finlay

Sometimes a lot of it is like with my hair, I have it here, my notebook out, and I’ll have like a pen in my hand. And as I’m going to write, I’ll just start talking. So if say, you know, I’m wanting to do some sort of like meeting thing, I’ll just start from the top of where I think like a meeting.

00:04:45:24 – 00:04:55:19

Sullivan Finlay

So maybe I just start going like, hey team, how are we doing? I think we’re just waiting like 1 or 2 more here and then. So I’ll just start writing this down and then, yeah, the jokes will come from that, but.

00:04:55:20 – 00:05:05:04

Zack Oates

Oh, that is so what did your like colleagues think? Like, did this ever get you in trouble when you were working full time and making your content?

00:05:05:06 – 00:05:35:02

Sullivan Finlay

Yeah, it’s a great question. I was terrified of them, like finding out. And then one by one, everyone when I was at Salesforce, everyone did find out. And it was just people were like so supportive of it because I think I was around other accountants who were also like, I would never do that. Oh yeah, and and there it would be the one off comments that like random company events, like there would be some sort of all hands and then like there’s a party after and one of my coworkers like, hey, the microphones right there.

00:05:35:02 – 00:05:42:22

Sullivan Finlay

And I’m like, okay, like I’m probably not going to perform just at a work function.

00:05:42:24 – 00:05:47:17

Zack Oates

But yeah, this isn’t this totally isn’t you, Jerry. Like. Yeah.

00:05:47:18 – 00:05:48:12

Sullivan Finlay

Right.

00:05:48:13 – 00:05:59:24

Zack Oates

Right. I know, I could just I could just imagine in one month you’re like, what it’s like to be a CEO, having a podcast and be like, hey everyone, I’m Jack boats, right?

00:06:00:01 – 00:06:08:24

Sullivan Finlay

Yeah. There wasn’t any, like, me impersonating a CEO. And then like, Marc Benioff comes up to me like, hey, man, cut it out. You know, that would have been cool, but.

00:06:09:01 – 00:06:19:03

Zack Oates

That’s amazing. But I mean, like, you did some work with Salesforce afterwards, right? Like, so it obviously ended well and they like played into it. They were like, oh, this is funny.

00:06:19:05 – 00:06:27:19

Sullivan Finlay

The funny thing about that was the the first partnership was Salesforce was when I was still working there and they didn’t know I worked there.

00:06:27:20 – 00:06:29:24

Zack Oates

No way.

00:06:30:01 – 00:06:41:22

Sullivan Finlay

Yeah, they reached out and it was through my agency and they like, hey, just want to see like it’s totally like a user of Salesforce. And I literally respond, I’m like, I’m an employee.

00:06:41:23 – 00:06:43:21

Zack Oates

I’m saying, here’s my badge number.

00:06:43:23 – 00:06:44:08

Sullivan Finlay

Right?

00:06:44:08 – 00:06:45:13

Zack Oates

Right.

00:06:45:15 – 00:06:57:07

Sullivan Finlay

I have benefits through you. So then later, like a week later, somebody from the social team, like messaged me on slack and I was like, hey, I think we’re working together on this campaign. But yeah, they’re great to work with.

00:06:57:08 – 00:07:18:12

Zack Oates

Oh, that is so funny. I mean, what a compliment, though, of like, you nailed that demographic. And so as you’re thinking about and this is one of the reasons why I thought it’d be great to have you on this podcast is because we have thousands of restaurants that listen to this podcast, and they’re thinking to themselves, how do I create content that’s going to break through, that’s going to talk to like, the new generation?

00:07:18:12 – 00:07:43:19

Zack Oates

And what advice do you have for them on both the creation of the content and then like coming up with new ways, because there are a few people like Fry the Coop, they’re in your hometown of Chicago, where he does a great job with his social, and that doesn’t mean that every single post is a killer. But eventually he gets to one that, like, gets into the hundreds of thousands, the millions.

00:07:43:19 – 00:07:57:14

Zack Oates

And like that helps the brand grow. And so Sean Walsh is another great restaurateur who does amazing content. But like, what advice would you give to those who aren’t as comfortable in front of a camera?

00:07:57:16 – 00:08:18:03

Sullivan Finlay

Yeah, I think well, to the comfortability, like it’s just a hurdle that you have to get over with time if you just do it enough up front eventually, like I have nothing else to lose at this point. I’ll just keep recording myself. But I think the other thing with that is the consistency in posting. I mentioned starting content in 2021.

00:08:18:03 – 00:08:23:21

Sullivan Finlay

I didn’t have anything go viral until like seven months after I first posted. And like, how many.

00:08:23:23 – 00:08:25:11

Zack Oates

Did you do?

00:08:25:13 – 00:08:29:16

Sullivan Finlay

Oh my gosh, I could find it somewhere, but it’s well over a hundred.

00:08:29:19 – 00:08:31:04

Zack Oates

Oh my gosh.

00:08:31:06 – 00:08:51:06

Sullivan Finlay

Yeah. And so it was, it was wild. And then the first one was something about living in Chicago and the kind of part two of this that I’d say is, I think why that hit and why I think a lot of things hit is, is deeply relatable. It was just a conversation about like when you moved to Chicago, this is the conversation you have with everyone you talked to.

00:08:51:07 – 00:09:07:10

Sullivan Finlay

And I knew it because I had just moved to Chicago two months prior. And so I think just knowing what you’re good at and like creating content from that, or knowing your lived experience and creating content from that, it’s the old adage to like truth and comedy. That’s what will break through more than anything.

00:09:07:16 – 00:09:15:13

Zack Oates

And do you feel like this new generation? Are there things that you found? Hey, these types of things work and these types of things don’t? Yeah.

00:09:15:13 – 00:09:40:15

Sullivan Finlay

That’s a good question. I think what we’ve started to see a little bit with kind of Gen Z starting to get into general for like, is that there’s this weird thing in the last couple of years where you’re almost penalized and I think it’s starting to break back, which is good. You’re almost penalized for looking like you’re trying because then it’s dubbed as like cringe, like it’s something that’s like, oh, this is okay, cool.

00:09:40:15 – 00:09:58:21

Sullivan Finlay

You really went for it here. And I think that’s one of the hardest things at first. But again, it’s just something you have to push through where it’s like, just do the thing, just be your authentic self. Because I think why it’s starting to break back, because now people are looking for that authenticity. Contrasted with like AI and the rise of AI.

00:09:58:23 – 00:10:03:24

Sullivan Finlay

They want to hear that human voice and that human story. So I think it’s starting to break back, which is good.

00:10:04:00 – 00:10:16:04

Zack Oates

And when you think about collabs, Howard collabs. Helpful. Is that something that you found increases followers or is it something that’s kind of like, you know, something that used to work back in the day?

00:10:16:06 – 00:10:19:14

Sullivan Finlay

Yeah. With brands or with other creators.

00:10:19:14 – 00:10:21:16

Zack Oates

Yeah. Like with other creators.

00:10:21:18 – 00:10:51:03

Sullivan Finlay

Yeah. I think for me, more than anything, I just think they’re so fun. Like, it’s fun for me to create with friends of mine because it’s just so much of this job is you creating by yourself. And so it’s fun to have different voices writing, performing together. I think, too, it does definitely help with growing a following. There was a group of like 5 or 6 of us who are doing a number of videos together with kind of the main purpose of like, let’s just expose each other to each other’s audiences.

00:10:51:07 – 00:11:08:18

Sullivan Finlay

And we definitely found that there was even in ways I wouldn’t expect, I had a friend who’s not in content creation at all who was telling me, like, yeah, I saw that video you did with like, other creators. And a lot of these creators are like bigger than I am. And he was like, I went and followed them because I was like, I want to support them.

00:11:08:18 – 00:11:26:22

Sullivan Finlay

Like, that’s so wholesome. One, two. It is kind of wild that, like, these are all people who are like pretty well established, but sometimes people just haven’t seen them. And so I think that was a pretty good example of working with other people, collaborating with them. And it was helpful for, I think, all of us.

00:11:26:23 – 00:11:31:20

Zack Oates

Who are some of your favorite comedians that you follow in kind of like similar veins?

00:11:31:22 – 00:11:58:19

Sullivan Finlay

Oh, that’s a good question. There’s the group almost Friday and like Will Angus specifically, they do a lot of great sketch stuff, especially on YouTube. There’s Kylie Brickman and then Jeremy Culhane, who got on SNL this year. They have a podcast called Artist on Artist on Artists on Artists, which is just very it’s all improvised, very inside baseball, like Hollywood and the arts and all that, that I think is very funny.

00:11:58:20 – 00:12:00:18

Sullivan Finlay

Yeah. This would be a couple that come to mind.

00:12:00:23 – 00:12:25:01

Zack Oates

Yeah. Because I think and it’s so interesting because you there’s like this whole push, kind of this anti-establishment push right where it’s like, let’s make fun of all these corporate tropes because it’s like it’s so ridiculous when you’re in it. And the thing that’s wild is how close you are to completely accurate, right? It’s not one of these things where, yes, it’s a caricature.

00:12:25:01 – 00:12:44:07

Zack Oates

It’s a character and a caricature of like certain things. But also, I literally have said some of the stuff that you say in your videos on my hands, meetings, word for word. And that’s actually how I found you. Someone sent me a video of you and it was like, are all hands made? And I was like, oh my gosh, I cannot believe this.

00:12:44:08 – 00:13:13:02

Zack Oates

I’m like a living meme. But like when you’ve spent years inside corporate America and now you make a living making fun of it. And when you think about that, like, what’s something that corporate leaders are doing that employees secretly hate, but like, no one’s really telling them, like, what are leaders missing on that? Again, relatable because all of the content you’re doing that’s getting so, so many views, people are like, oh yeah, I totally can see that.

00:13:13:02 – 00:13:16:18

Zack Oates

But leaders sometimes are oblivious to it. Yeah.

00:13:16:18 – 00:13:39:23

Sullivan Finlay

That’s a good question. Well, I think kind of the sentiment you’re sharing, I think that’s something I’ve been wrestling with even of like I think in content in general and especially in corporate content in this like corporate comedy space, there’s a lot that does skew negative. And I’m a participant, you know, and so it is like something I wrestle with of like, how do you kind of satirize this?

00:13:39:23 – 00:14:14:20

Sullivan Finlay

Well in a way that like people find funny and find relatable, but it’s still like somewhat uplifting? I don’t know that I’ve found the answer to that, but it’s something I’m always asking myself. I think as far as like what corporate leaders do, that people kind of push back on, okay, this is somewhat controversial, but I think sometimes in an effort to seem cool or hip, corporate leaders can be like, way to chill about working from home, where.

00:14:15:01 – 00:14:16:02

Zack Oates

I think.

00:14:16:04 – 00:14:35:10

Sullivan Finlay

Where I think getting together is a good thing. I think community is good for humankind, and I think sometimes it can be in an effort to, like, seem more relatable or like cool, like it’s like, hey, like, yeah, we can just work from home. It’s all cool. It’s like, yeah, but the point is that we’re like meeting people and working with people.

00:14:35:11 – 00:14:45:19

Sullivan Finlay

And eventually if you just work from home for so long and there are great benefits to it, and some people need it and that’s great. But I think like sometimes it can go too far.

00:14:45:21 – 00:15:01:18

Zack Oates

By the way, your publicist, I think, should be so proud of how you navigated that question. I mean, that was PR training, right? Spot on. Sully. You’re like, but some people need it and that’s great. And you know, like corporates. Great. But here’s the funny thing anyway.

00:15:01:19 – 00:15:08:13

Sullivan Finlay

My PR training is just like listening to too many podcasts myself where I hear people do the same things.

00:15:08:15 – 00:15:27:22

Zack Oates

So yeah, it’s like, I know you always have that the back of your mind with everything that you say. It’s always like, yeah, don’t get canceled, don’t get canceled, cancel. Thank you. So as you think about creating content, what are some good hooks? What is the anatomy of a great video on social media? I think.

00:15:27:23 – 00:15:47:04

Sullivan Finlay

One of the biggest things on TikTok that I think about, because it’s kind of seen as like the main metric is like watch time and how many people watch your whole video. So like completion rate. And so for me, a lot of videos that I did that started working where this like checklist style, where throughout the video things would start checking like, like.

00:15:47:09 – 00:15:53:24

Zack Oates

But the CEO says all these like, you know, corporate things and like okay. And like synergy and like. Yeah, right.

00:15:54:00 – 00:16:18:20

Sullivan Finlay

Exactly. And so it’s like each time something to me and checked off and there’s something that’s like oddly cathartic to it, I guess. But like people want to see them all get checked off. And so I found that watch time was much higher for those types of videos. Another one I find is if it’s two different things, like my friend Jacob and I will do a lot of these where it’s videos, where say, it’s how white collar workers versus blue collar workers describe what they do for work.

00:16:18:20 – 00:16:33:21

Sullivan Finlay

And then the white collar worker goes first and it’s like just jargon filled and it’s a lot of whatever. And then the blue collar worker comes on at the end. It’s just like I’m a welder, you know? And so it’s like it’s just people want to see the second thing because you’ve set.

00:16:33:21 – 00:16:34:11

Zack Oates

Up this.

00:16:34:16 – 00:16:55:12

Sullivan Finlay

Thing of like this versus this A versus B, I want to be able to see B, and then we just keep B short so that they complete the video. And because it’s just a quicker out it’s a quicker last joke. So it’s generally we try to make it funnier. But yeah I think anything that can increase watch time, I’m always trying to think of like new formats to drive that.

00:16:55:12 – 00:17:18:07

Zack Oates

But yeah, that is some killer killer advice there, Sally. Because like, I see those videos all the time, you won’t believe what happened next. Or they cut the videos off at number two. So that way it like prevents it. So now it makes more sense. Why? Because you watch the whole video waiting for number one. Whereas at the second I see number one.

00:17:18:07 – 00:17:37:19

Zack Oates

Usually I’m like, oh, I know what this I know what this is. Right? And then you skip it. That’s killing. Now I know why they do that because that’s so annoying. Or oh my gosh, Sulley, the worst is when you’re on Instagram and you see this video and then at the very end it’s like, like go for part two and it’s like, right, you go on to the page and you’re like scrolling.

00:17:37:20 – 00:17:58:17

Zack Oates

Like, what did I just watch? How far down is this? Like, yeah. And I saw that Instagram started to do like a click here for like the second part two video. They started interesting. They started to have that. I noticed that last week. I don’t know when it came out, but so anyway, I just think stuff like that is really interesting and that is some great advice they’re selling well.

00:17:58:18 – 00:18:02:14

Zack Oates

How do people find and follow you? What’s the best way to see you?

00:18:02:16 – 00:18:10:22

Sullivan Finlay

Yeah, it’s just at Slowly Findlay on all platforms, on TikTok, Instagram, LinkedIn, all the little things.

00:18:10:22 – 00:18:16:17

Zack Oates

So what do you think, by the way, of using your name versus like Jen from corporate or something like that?

00:18:16:19 – 00:18:31:20

Sullivan Finlay

Oh, that’s a good question because I have friends that do that like corporate Natalie or Lisa plays like corporate Aaron corporate bro like. And I think that’s great. It works for them. I personally have kind of taken the stance of, I want to be able to navigate through different things and use my name.

00:18:32:00 – 00:18:32:16

Zack Oates

For interesting.

00:18:32:17 – 00:18:53:22

Sullivan Finlay

Yeah, try to pigeonhole myself because I’ve kind of pigeonholed myself enough already where I am doing a lot of corporate things. I’m like, I want to do, you know, other types of content. But yeah, I try to just be able to use it for different things. I also perform and do like improv and sketch a decent amount where I think I’d rather have my name on a show than, you know, some character name or something.

00:18:53:22 – 00:18:56:02

Sullivan Finlay

But yeah, awesome.

00:18:56:07 – 00:19:15:24

Zack Oates

Anyway, interesting. I, you know, so I just appreciate you coming on. This has been such an awesome podcast. Super interesting to hear the journey from being changed by corporate to conquering it through comedy, and for being the real synergy here today. Today’s ovation goes to you. Thank you for joining us on Giving Ovation.

00:19:15:24 – 00:19:18:11

Sullivan Finlay

Thanks. Thanks for having me I appreciate it.

00:19:18:15 – 00:19:40:07

Zack Oates

Thanks for joining us today. If you liked this episode, leave us a review on Apple Podcasts or your favorite place to listen. We’re all about feedback here. Again, this episode was sponsored by ovation, a two question, SMS based, actionable guest feedback platform built for multi-unit restaurants. If you’d like to learn how we can help you measure and create a better guest experience, visit us at ovation.