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You Need a Little Crazy
In this conversation, Denis Keane shares his journey from a corporate career to entrepreneurship, highlighting the challenges and lessons learned along the way. He discusses his experiences in the nightlife and restaurant industries, the importance of people skills, and the role of adaptability in navigating the ever-changing landscape of startups and technology. Denis emphasizes the need for risk-taking and the value of understanding business fundamentals, while also reflecting on personal growth and self-worth.
Show Notes
This episode presents a profound exploration of career transitions, personal growth, and the entrepreneurial spirit through the lenses of Maricela Herrera and her guest, Denis Keane. The narrative begins with Maricella's honest reflection on her struggles with motivation and the emotional toll of returning to her routine after a significant hiatus. Her vulnerability lays the groundwork for a rich discussion with Denis, whose dynamic background as an entrepreneur in the nightlife and technology sectors illustrates the multifaceted nature of career journeys. Denis recounts his experiences navigating the challenges of establishing a successful nightclub in a gentrifying neighborhood, offering insights into the importance of risk-taking and seizing opportunities. The conversation further delves into the lessons learned from both industries, emphasizing the value of people skills and the necessity of adaptability in the face of uncertainty. As the episode unfolds, listeners are invited to reconsider their definitions of success and the paths they choose, ultimately reinforcing the idea that both personal and professional growth often emerge from embracing chaos and uncertainty.
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Takeaways:
- In the podcast episode, Dennis Keane discusses the necessity of adaptability in business, emphasizing that the ability to pivot is crucial for success in rapidly changing environments.
- A significant theme addressed in the interview is the importance of understanding financial metrics, which is essential for running any business effectively, including restaurants and startups.
- Dennis highlights that personal connections and people skills are indispensable, as they enhance communication and foster a productive workplace culture in both the restaurant and tech industries.
- The conversation reveals that fear of failure often inhibits individuals from pursuing their passions, and Dennis advocates for embracing risk as an integral part of the entrepreneurial journey.
- Dennis's journey illustrates how experiences in the restaurant industry can provide transferable skills that are extremely beneficial in the tech startup world, particularly in managing teams and understanding customer dynamics.
- The episode also touches upon the evolving role of AI in business, suggesting that those who adapt and learn to leverage technology will thrive, while those who resist will likely fall behind.
About Denis Keane:
Denis Keane is an entrepreneur and investor who has founded multiple businesses, backed early-stage startups, and advised companies on growth and business development. Most recently, he served as COO and investor in an AI startup that successfully exited through acquisition. Denis now works with founders and leadership teams to help scale operations and unlock new growth opportunities.
Transcript
Have you ever felt like the script you're following doesn't quite fit anymore? Then you're in the right place. I'm Maricella Herrera, and I started. Sh*t I Just Quit My Job after walking away from a job I thought defined me?
Forget the highlight reels. Here we talk about the messy middle, the doubts, the detours, and the chaos that come with rethinking who we are.
Because the truth is, it was never just about quitting a job. It was about questioning everything I thought I knew. Hi, everyone. Happy New Year. This is Should I just quit my job? And I'm Maricella Herrera.
Thanks for joining me. And I know it's the end of January, so saying Happy New Year might feel like it's a little. A little late for that, but.
But I always tend to think of the start of my year as later than January 1st because I'm usually gone for long periods of time during the holidays. I didn't come back to New York until a couple of weeks ago. And then after coming back, I had to slowly try to bring myself back to a routine.
Because when you've been gone for a really long time, when your life has been, like, on pause, so to speak, it's hard to get back into it. And my life was really paused, like, for the time I was away, my life was just hanging out with my niece and my nephew. And it was awesome.
I had a lot of fun. I love those kids, and I miss them very, very much. So I. When I'm with them, they're my whole focus.
And it's almost like a. I don't know, like a hangover, I guess.
I. I don't even know how to explain it, but, like, the whole idea of coming back to New York and feeling the pressure of, like, I have to do stuff because I've been gone, but at the same time feeling zero motivation to do it and feeling really tired and feeling all the feels for both what I had, but also what I left behind. It's. There's a lot of emotions that I probably should write something about or create a minisode about.
And that was what I was expecting myself to do. I thought I was going to do a minisode and talk about coming back, talk about my vacation, talk about all these things.
But, y', all, I could not, for the life of me get myself to start. The last two weeks, I've felt this just lack of motivation that has been so deep. It was almost like apathy. Like, I just. I didn't want to do anything.
I Didn't feel like starting anything. And I didn't start school until this week. So I, I just, I don't know. I, I, I couldn't.
And I was talking to a friend of mine who kept being, you need to start to get momentum. Like, you need some motion for it to really kick off.
And before I left in December, I was actually really pumped about ideas and about projects and about things I was doing. So it was almost sad that I felt, like, this lack of motivation. So I was dealing with both that sadness, too.
Like, I, I had lost something, which I guess I had. But she was right. You need some motion to build that momentum.
So I think starting school helped, and, like, I started doing little things that would get me inspired again. And here I am. I was editing. I was like, I really love this. Like, I did start getting that spark back.
So I'm excited now, and I think I picked the right interview to start with, because the person who I talked to, Dennis Keane, who you're going to meet in a moment, is completely opposite from the whole unmotivated state that I was in. He's someone who does a lot. He can't be really still. He needs that constant, like, doing many things, doing many interesting things.
He's an entrepreneur, an investor advisor. He started this entrepreneurial journey in the restaurant business, which is what kind of led me to want to talk to him.
He's a friend of a friend, and I knew from her about, like, him and having owned this, like, massive nightclub in the Lower east side years ago and, like, started it when the Lower east side wasn't even the Lower east side, like, back before it gentrified, back before everything. He's just really cool.
It's really interesting to listen to how the lessons that he learned from that industry, from those times, then informed a lot and transferred into the skills he took to all the other things he's done. His last gig, I would say, was being the COO of an AI technology company. So very interesting background. Anyway, I'm not doing it justice.
I'm just excited to tell you about it. I'm just excited to be back now, and I missed this feeling. I really missed this feeling. So thanks for that. Okay, I'm gonna go now.
I'm gonna let you go listen to the conversation I had with Dennis. Thanks again for listening. I'm back. You can expect me in your podcast abs every other week this year.
I think it's what works the best right now for me, as I'm trying to do and explore a lot of Other ideas and projects, but I'm not going anywhere. So happy to be back. So happy to be able to continue to do this work. I would love to hear from you. You can leave comments.
It would be awesome to know feedback, but also just send me a note. Quitmyjobpodmail.com Anyway, I hope your year is off to a great start.
Thank you for taking precious time out of your day to listen to this, Sending you all lots of love. And now, here's my conversation with Dennis. If I met you at a party, what's the one story you tell that you feel showcases who you are?
Denis Keane:That's a tough one. I don't know. There's, you know, like, there's so much difference in a person. Right. Like, parts of me thinks I'm funny.
Parts of me thinks I'm pretty serious. Parts of me thinks I'm a good entrepreneur. Parts of me questions whether I'm a good entrepreneur.
I love working with people, but at times I can really hate people. So it's a really, you know. Yeah. So sometimes I'm just like, I hate everybody. And I really feel that. And then other times I'm.
But then when I'm working with people, I love the people I work with, and I always want to get the best out of them. So I. I love working with people, but I don't like people.
Maricella Herrera:So it makes. It makes a lot of sense. I actually feel that way a lot of the time.
Denis Keane:Okay.
Maricella Herrera:So that, to me, resonates. You can love people but also hate them at the same time.
Denis Keane:Yep.
Maricella Herrera:Okay. That was not a fair question. I know. It was a hard one. So I'm gonna go back to just my normal. But I. I'm trying new things in the podcast.
Denis Keane:Yeah, sure. Why not?
Maricella Herrera:But my first question always is, what did you wanna be when you were growing up?
Denis Keane:So I actually had no idea. I mean, I knew what I didn't wanna be.
Maricella Herrera:What was that?
Denis Keane:Okay. Cause when I was young, I had bright red hair, big freckles. I was skinny and lanky, and I was terrified I was gonna grow up to be Howdy Doody.
So that was my big fear as a kid. Now I probably really dated myself there. So anybody in your audience who wants to look up, howdy, do you get to see how I looked when I was young?
But all, like, the typical boy things. I wanted to play hockey for the New York Rangers, but I couldn't skate, so I kind of made it a little difficult.
But even, like, up through college, I really had absolutely no idea what I wanted to do. I went to business school at Villanova because I was thinking business is broad and I'll do something in business.
So it's kind of like leaving my options open. And even when I was graduating, you know, got different job offers and I got an job offer from Procter and Gamble.
And my thought process wasn't like, oh, this is my dream job, this is my dream company. It was just like, P and G is a good company, they're reputable. I should probably take that one. So I kind of just like fell into starting a job.
Cause I need to make money. So I really had no direct path of anything I knew I wanted to do.
Maricella Herrera:So it was more about security at that point.
Denis Keane:Yeah, I think a lot of it too was more about this is what I do at this stage of my life, you know what I mean? Because I was always kind of a reasonably well behaved. My parents didn't have too much trouble.
And it's kind of like, you know, you go to college, you get a job, you get married, and you get the white picket fence. So it's just kind of more of that.
At the time, I didn't realize I was going through the motions, but I guess in a way I was going through emotions of just, here's what's next. Here's what, you know, you graduate college, you get a job. So that's just kind of where it was for me. There was no passion, there was no excitement.
It was just like, here's the next step.
Maricella Herrera:Yeah. Knowing the little bit about you from when we talked and about your story, it does feel like, not, I don't know, like you.
It feels like you would want that excitement, but I understand that, like going through the motion.
Denis Keane:I mean, I got a lot of excitement after my. And once my career, once I got into my own things and.
Maricella Herrera:Right, right, right, exactly.
Denis Keane:But at that time it was just like. It literally was like, okay, P and G is a good company, I should go work for them. That was really my thought process.
But I also, I also knew then I couldn't be corporate after a little while because after about a year and a half of Procter and Gamble, they offered me a promotion and it was in Alabama.
And I was kind of like, okay, now, I knew a friend of mine from down south and he was like, oh, the Alabama, they're not going to like a northern boy like you down there. And I went, yeah, I went to my mentor in Procter and Gamble and I was like, okay, I'm being sent to Alabama. He's like, this is a great opportunity.
You're getting promoted fast. And I knew I couldn't turn a gap down because you just can't do that. I was kind of like, I don't really want to move to Alabama.
I'm like, what do I do? He's like, you go down there, you do really well, and then you get promoted someplace else. And I'm like, where would that be?
And he says, well, it could be wherever the company needs you. And I was like, so what's my final goal out of all this?
It's like, to get to Cincinnati, of course, which is where Procter and Gamble's headquarters is. So I'm literally like, holy shit. Like, my whole life is going to be dictated by this company.
Where I'm going to work, where, when I'm gonna live there. It could be sent to Europe. And it's just like, if they offer you a promotion, you gotta keep taking it if you wanna keep moving.
So that's when I was like, I gotta get off this train. And I quit Procter and Gamble and went to get my mba.
And then I realized after the first year, it was just corporate again, you know, it was like Procter and Gamble was recruiting me for a different position. ExxonMobil, whoever.
And I was like, wow, I'm just going, if I stay in this path, I'm always gonna be in a corporate where cooperation's always going to tell me how my life is going to go.
Maricella Herrera:It's interesting that you went for an MBA thinking you needed a change. And you're right, once you get there, it is. Can be a change, but it's going to be a change in the same.
Denis Keane:Yeah, the same realm. Yes, the same realm.
And I said, what really got me is, like, when Procter and Gamble came back and was like, oh, you know, we want you for this position now. And I was like, what am I doing? This is going back to, I don't.
Maricella Herrera:Know, feel the same.
Denis Keane:Yeah. Like, I'm just back on the treadmill, you know, running. And I just.
Maricella Herrera:Until you got to Cincinnati.
Denis Keane:Until I got to Cincinnati. And that was woohoo. So, yeah, that's when I knew I better make a change.
Maricella Herrera:So how did you actually approach that? Because if you know, you don't want corporate, I guess you knew you had to do.
Denis Keane:I mean, I kind of felt to it because my mother owned a restaurant, so I was working there part time for money just while I was getting my mba. And it was kind of like, yeah, but I guess I'll do this for now.
And I worked for her for a number of years and then started opening my own places and then just started branching out the different fields and, you know, just trying different things. And some. Some successful, some not so successful, but overall, it's been a great journey.
Maricella Herrera:Did you work with your mom for a long time or did you quickly.
Denis Keane:Go, no, I did. I did for a good few years. Probably about close. Eight, maybe eight, nine years.
Maricella Herrera:That's a long time.
Denis Keane:Yeah, it is a long time. And it's. It's very difficult to work for, you know, work for a parent especially. My mother was a tough woman.
her own Irish pub back in the: Maricella Herrera:I love that.
Denis Keane:Yeah, so she's definitely. If you work for her, you could work for anybody. She was. No nonsense. She was tough. So, yeah, every other restaurant loved getting.
Trying to steal people from her because they knew they were well trained and they could do a good job. But, yeah, it did get to a stage of like, all right, this is gonna probably really ruin our dynamics if we stay working together.
Cause we definitely have very different ways of handling people and doing things. So, yeah, I eventually got my own place and then kind of went off from there.
Maricella Herrera:And it's not just working with family. It's also working with family in a very, very high pressure type of environment and industry.
Denis Keane:It's a lot of hours. You know, it's weekends, it's nights. It's, you know, you're dealing with people who are drinking.
There's men and women fighting over each other or can be somewhat violent at times. You deal with drunk people.
Maricella Herrera:Drunk people and idiots. Yes.
Denis Keane:Yeah, yeah, exactly.
Maricella Herrera:So you went ahead and started your own thing. I would really like you to tell me the story of it. Because you were working with your mom for a long time and wanted to get your new place.
Why was it. Was it mostly because you wanted that independence or did you want to change and then how did you go about it?
Denis Keane:Yeah, it was a little both. I mean, I. I was still working for. When I. When I actually opened my first place, that was, you know, that was on my own type thing.
So I kind of kept both feet in the door, and then it just got to a stage that's not gonna. It just wasn't working with us too. So then I wound up opening another place, and then I kind of. They were all in Queens In New York.
And then I went into the city. That's when I started really blowing up.
So I opened a small Irish pub in the city and then from there I wound up opening this really big nightclub down on the Lower east side. Like Big three story, all celebrity, all crazy antics. It was a wild time.
I'm glad I did it and I'm glad I got out of it because I'd probably be dead if I stayed in that business. Because nightclubs don't get really busy till 11, 12 o' clock at night. So you're really, you know, you're going from 11 to 4 in the morning.
By the time you get everybody out, it's, you know, it's at least five before you count the money, do everything like that. And a lot of times we'd have the celebrities. A lot of times you can't say no to them. So they'd want to hang out after hours.
So you're with them till 5, 6 o' clock in the morning before you get up to get out. So it was a very, you know, I'm getting home 7 to 8 o'clock in the morning. Sometimes it was a wild experience.
But it was, you know, again, I'm glad I did it. Cause I met so many interesting people and it kind of then led me to different other career paths after that.
Probably got into different types of businesses like event production and then. And eventually then into working in technology startups. You kind of like depends. Nothing was.
I didn't certainly have a plan that, oh yeah, I'm going to be in tech startups one day. But it's just kind of one breadcrumb, you know, we just keep picking up and we can meet different places and that's.
Maricella Herrera:I love that. That's why I love doing this podcast.
Because I realize how much we don't see until we're kind of looking in hindsight, how things connect and you're just going down a path, but then you have no fucking clue what's going to happen.
Denis Keane:No clue. I mean, I guess if you stay in the corporate world, you can. Yeah, right.
You can kind of be like, okay, I want to be vice president of so and such and such one day. Or yeah, you can kind of like plan it out. Right.
Maricella Herrera:I mean, which is why I don't have that many corporate people on my show.
Denis Keane:But. Right. It's true though. If you, if you work, it's kind of like a lot of who you are. Right.
If you're a person who likes stability and knows what's coming next, which there's nothing wrong with, then it's, we need those people too. Yeah, it's great. And that's what they're there for. But me, I'm too, I, I'm all over the place.
I get bored easily and I need to be always doing something different. You know, the restaurants and bars and nightclubs that certainly provided that on a daily basis.
And then when you go into the startup world, I mean, you know how that is. I mean, one day you're the accountant, next day you're the marketer, the next day you're head of, you're doing head of hr.
You're doing, you know, all the things, all the things. So I find that exciting.
Maricella Herrera:I want to talk about the difference between the bar and restaurant scene and particularly technology startups, because I think that that's probably, I'm sure there are lessons that translate, but it's also very different in many ways. But first I want to talk about your club because you started that club when the Lower east side was not the Lower east side.
I mean, it was the Lower east side, but it wasn't what it is today.
Denis Keane:Yeah, the Lower east side back then was, you know, a lot of burned out buildings and a lot of factories. The building that I actually took over was a, was a burned down building that was just, you know, pigeons were living in there.
Pigeons and rats are basically the tenants. So we, I went down there and the community board to this day still hates me.
Maricella Herrera:That's how, you know, you did a good job.
Denis Keane:Yeah, I guess so.
No, to this day I think they still shudder when they hear my name because they're, because they blame me for kind of gentrifying the area, which I, it was coming no matter what, you know, that, that area had a lot of big factory type buildings which lends itself to hotels and nightclubs. So I just happened to be like in every other place down there. Before me there was, you know, a few music places and there was a lot of dive bars.
That's what the Lower east side was, just dive bars and some music venues. That was just the nightlife down there.
And then I came in and I opened this huge three story club with lines down the block and celebrities coming in and they would bring me down to community board meetings and just because they assumed I was opening an Irish bar, because that's what my history had been.
So when I went in front of the board to ask for my liquor license, you know, it was kind of like they knew my history of Irish pubs and they're like, oh, this guy's gonna open an Irish pub. And all of a sudden I came in and did this huge nightclub. But certain, certain days would be like police outside keeping the crowd under control.
And then right after me, within a year or so, just hotels and clubs and it just really changed around. And then they of course blame me for increasing rents and all the gentrification things that follow. I was first and I have to blame somebody, right?
Maricella Herrera:Yeah. What made you think, was it mostly just because of the space lent itself for that? Because again, it's like if it's.
You're the first, there's something that has to have.
Denis Keane:Yeah, you know what, it's definitely the space. It was something that I could. It was burned out so I could afford it. And I was able to get construction loans from the banks at the time.
And it definitely was something too. It was a very edgy neighborhood.
And a friend of mine, he was a police officer and back in a few years before me, he's like, all I deal with down there is drug addicts and prostitutes. What are you doing? What is happening?
And he was even told me a friend of his who's also a cop bought a building and every night he had to sleep in it with his gun to make sure that people didn't break in while he was renovating it and stuff. So he was just like, you're out of your mind. But to me, it was like, it was just, it was that.
It had that, that personality to the area and I definitely thought it was going to be up and coming. So I took a chance and, you know, rolled the dice and it worked. It worked out.
Maricella Herrera:That's the, I think, little bit of crazy that you have to have if you're going to have. If you're going to do something like that.
Denis Keane:I think almost every entrepreneur has to have a little bit of crazy, right? Yeah. You could lose everything. I mean, you don't know when you open something that it's going to work no matter what business it is.
You can't be guaranteed that it's going to happen.
Even like the last tech startup I was with, that should have been a billion dollar company, but we just couldn't get our Series A and you know, we got acquired, which is a win. But you don't know. You're always taking a chance, right. It could have been nothing or it could have been a billion dollars.
It wasn't either one of those, but you just have no idea.
Maricella Herrera:But it could have, you know, like you're taking that Risk and that, that's the whole point. You're.
Denis Keane:I don't know if too many entrepreneurial things you could do that don't involve risk.
Maricella Herrera:I don't think there are any.
Denis Keane:Yeah, all of them. So you, you either gotta be crazy, stupid or both. And I think I'm a little of both sometimes.
Maricella Herrera:I think, I know. I think you have to be crazy and actually smart if you're gonna do it right, to be honest.
Denis Keane:Well, I mean stupid in way of like sometimes you just ignore the, the high risks.
Maricella Herrera:That is true. You have to have. I laugh cuz I've. Since I teach entrepreneurship, I'm not teaching it this semester, but I do all the like theoretical words come in.
I'm like, you have to have an internal locust of control. Like doesn't matter. You have to be nuts. Yeah, that's basically it.
Denis Keane:And you just have to go for it sometimes. And sometimes they don't, they don't work. I've started things that crashed and burned and you just gotta be able to pick your pants up and you know.
Maricella Herrera:Can you tell me about one of those?
Denis Keane:Sure. I started a CBD company. So I had connections, you know, somebody was going to help me out there. And it was great timing.
We called it Wisdom Essentials and my college roommate came in with me on it. So we partnered up, we put together a great brand, we had everything good.
But then right as we were going to launch, Covid hit and that kind of just put the brakes on everything. So our website was six months delayed being done, but you're still paying money for things.
So then by the time Covid ended and we started getting going, kind of CBD kind of lost its luster. People got more into like doing if they're going to do cannabis, they're going to do the whole cannabis and not just the CBD portion of it.
There's a few companies out there still doing okay in cbd, but I don't think it's. The market just kind of collapsed.
So just, you know, we did it for a few years and at the end of it just had to kind of turn off the lights and, and walk away. So that was a pretty recent one, pretty big one. I've had places I've opened up and I don't think I've ever opened like a restaurant or bar.
That was exactly how I envisioned it.
Maricella Herrera:Oh, interesting.
Denis Keane:Yeah. I find like you, you go in and the place kind of tells you what it, what it has to become, if that makes any sense.
You have your vision, but Maybe my vision's just not that great or whatever it is. But I go in and most times I wind up changing. Maybe it's. I open as a regular bar and then I realize, shit, I should be a craft beer bar.
And then I'll. I'll make it a craft beer bar and that'll be wildly successful. I don't like karaoke, personally. I didn't like, like it at all.
I opened the place Cornerstone Tavern, and this Scottish bartender of mine convinced me, like, he loved karaoke. He's like, please let me do a night, whatever. Now we do seven nights a week.
You know, we did, you know, we did seven nights a week because it just, people wanted it and it became very, very successful and it brought business in. Like, you don't start to like 10, 11 o' clock at night. So I put that late night crowd in. So you.
I never would have, not a million years, if somebody said to me, you're going to have a place that does karaoke. I'd have been, not a chance. And next thing you know, I was doing seven nights a week.
Maricella Herrera:But that is thinking of parallels. That's just like pivoting. Right. Like you're listening to what people want and then you pivot towards that.
At the end of the day, you're not necessarily your customer. No, right.
Denis Keane:No, you. I think people get stubborn or think like, this is my vision and this is what it's going to be. They're either really lucky if it works or they're.
Or they're brilliant and they just, you know, they really sort saw it ahead of time.
Maricella Herrera:Yeah.
Denis Keane:I think 90% of times, or maybe more than that, entrepreneurs have to just pivot and do what needs to be done.
Maricella Herrera:Yeah. Follow what people are telling you.
But it's good though, what I think in what you just said about people who get really stuck on their vision because you're saying your bartender convinced you to try out the karaoke. And that I think is important to like, listen to people who might be more.
In that case, probably seeing the people interacting with them day to day in a way that can give you more information.
Denis Keane:Yeah. I had a different place called the Stag's Head that I opened as an Irish bar. It was named after bar in Dublin.
And I had a manager working for me and she convinced me to go craft beer. And it was really early in the craft beer stage. I was kind of like, what? I'm like, she's like, you know, no Guinness, no bud.
And I'm like, that's sacrilege how can I have no Guinness? Seemed like sounds. And I was just like, how about we do half and half? And she was like, no, you know, it has to be.
If you're going to do a craft beer bar, it has to be a craft beer bar. And she was right. It turned out to be. We got right in the movement when craft beer was taken off. And it was a very.
It was very successful for many years. And if I'd left it as an Irish bar, I'd probably just an oh so ran so so place.
Maricella Herrera:Like just another Irish bar.
Denis Keane:Yeah. Just.
Maricella Herrera:Again, smart of you to actually listen to people. Like, you can't be stuck in your little own echo chamber.
Denis Keane:I think no matter how smart I think I might be there, other people are smarter and. Or at least maybe have better ideas, and you gotta listen to them.
Maricella Herrera:I used to say that my job was to hire people that were smarter than me.
Denis Keane:I always said that. I always said that if I. If I'm working for a company, I'll always say if I'm the smartest person in the room, I'm in the wrong room.
Maricella Herrera:Yeah. I mean, why wouldn't you want that?
Denis Keane:Oh, yeah.
Maricella Herrera:I think a lot of it is ego for some people, but it's.
Denis Keane:It is. And it's silly because it's. I always try and hire people that are better at what I'm not necessarily great at.
Like, I don't love being a front person. You know, like when you open like a nightclub or a bar, you know, you want that owner who's like, hey, you know, and blah, blah, blah.
Maricella Herrera:Wasn't you.
Denis Keane:That's not me. But I would always hire somebody who wants so that, you know, so fine. I could be like more of the I'll run the business things and I'll be there.
Now I have my person who loves being the fun person and they enjoy that. So you always gotta find what your weakest parts are. And everybody says, you know, they're into the bar business because they want to be that.
Like, hey, I'm the guy. And I actually was kind of more the opposite.
If you surround yourself with people who like doing what you don't like to do or are better at doing what you. What you can't do, you're a better chance of success 100%.
Maricella Herrera:That's the pairing. That's. I used to. With my. In my old company, I was the CEO and the CEO, and I would always say I'm the. I'm a good COO for her.
I don't Necessarily know that I'm going to be a good COO for someone else, because the point is to kind of balance that.
Denis Keane:Right.
The last start I was with, I went in and it was a video imaging company, and it was mainly working with influencers and people who do a lot of videos and wanted to edit them and AI and that kind of stuff.
Maricella Herrera:Is that how you got there?
Denis Keane:Yes. Yes.
Maricella Herrera:Okay. I'm like, trying to see that, you know, you said going into celebrities.
Denis Keane:Yes. So that kind of. I kind of went in for that. And within a short period of time, it was kind of a thing of like, I don't know if this is.
This is really going to have a life on it. I think AI is just going so good that I kind of need.
And a few months later, we totally pivoted and changed the whole company to working for brands and agencies. And then I wound up being COO because I had the most business experience. And they were like, they were the scrappy startup, really smart people.
Super smart, really good people to be around, but the business was like, all over the place. They didn't do their books, basically. And I would always say to them, if you don't know your numbers, you have a hobby, not a business. Yes. So.
So I never thought I'd be like the COO type, but then I kind of fell into that role. That company, just because it needed. It needed the structure.
Maricella Herrera:And again. And you were the right fit for it because what they needed was exactly the experience that you had.
Denis Keane:Right.
Maricella Herrera:In the bar scene and restaurant or more nightclub scene. You said they're usually the people who end up going that route are the ones that want to be like that front person.
When you said that, I had this reaction of feeling that maybe wanting that and wanting to be that usually makes you a little weaker in the fundamentals. I don't know. You have to. I guess you have to partner with someone.
Denis Keane:I mean. Yeah. So the people who are like that need people like me.
Maricella Herrera:Yeah.
Denis Keane:Or vice versa. I'm. I'm good at business. I'm good at, you know, I'll hire, I'll fire, I'll, you know, I'll do all those things. I'll make the structure because it's.
It's a lot easier to run a business when you have.
When employees know what you're expected of them and they have written manuals and there's training and there's, you know, all the things that go along with that. So I'm very good at being organized and structured in business, but Again, I don't love the whole oh, look at me.
Maricella Herrera:So you are the COO type.
Denis Keane:Yeah, I guess. Yes, I'm very structured but I can also be part of this chaos that's, that's in the bar business.
So it's not like I'm like sitting in the office all day. I'm definitely out on the floor, I'm definitely doing things, but I didn't think I would actually be like, like a full on coo.
That's my job every day. When they asked me to take on the role, I told them I'd give him one year.
So I did about nine months before we got acquired and so I was like, I can't do this for more than a year because it's just.
Maricella Herrera:But I think that, and you know, you said it at the beginning. I do think that there's an aspect of startups with the like there is an organized chaos or maybe not even organized.
There is a little bit of chaos that is maybe a little reminiscent of kind of that more restaurant industry.
Denis Keane:Yeah, yeah. I mean, yeah, startups are chaos. They're, they just, they are.
I mean especially when you're pivoting and trying to figure out what the market wants and you go in with a thought and no matter what that thought is, especially in tech, I think your customers are going to tell you really fast whether you got a product or not. So you got to be. It's just very chaotic.
But I said so they had all the chaos going on but the only way to scale is then you have to have the structure.
Maricella Herrera:So tell me a little bit about the journey because you know, we jumped around and you, I know said event, something around event production in between here, these two, these two big ones. So I want to go back and kind of, if you can tell me a little bit about that.
Denis Keane:Sure. So from the nightclub business, you know you get to know a lot of people.
Maricella Herrera:How long were you, did you have that?
Denis Keane:Actually it was, I only, I, it was. Took me almost two years to build the building, you know, which makes sense.
It was a four, it was a four story building and by the time you get to Brian financing and so maybe maybe a year and a half, a little more than a year and a half.
I actually ran it my, you know, I was in there running it for a little over two years and I said like it was an amazing two years but I, it was just, it wasn't for me long term.
So when I got, when I was getting out of that, these guys I knew had an Event production company doing all the film festivals, Tribeca, Sundance, Toronto, Cons, and they did a lot of the fashion shows. So we would. So we knew a lot of the, you know, actors, agents, and people like that. So we then would do all the parties for the movie premieres.
So we'd have all the celebrities come in and we'd, you know, we'd set up, like, we'd take over some kind of a venue and we'd provide, you know, DJ or band or both. We'd set up the food, the alcohol. So it was a lot of. So you're doing a lot of, like, trade and trying to get sponsors.
So you want like, a liquor sponsor so their liquor will be there and they'll give you. You know, because celebrities never pay anything for anything. Like, they don't ever.
No matter how much money a celebrity has, they don't pay for anything. So you have to get everything for free and then get sponsors to come in.
And what the sponsors do is, you know, the celebrity would maybe get a picture with them holding that beer bottle or, you know, the step and repeat. You know, they had the logos up. So that's actually a pretty big business. But it's also a hard business because you're.
They're constantly hitting up brands, you know, trying to get these sponsors.
Maricella Herrera:It's a lot of sales.
Denis Keane:It's a lot of sales. Yeah.
It's a lot of unlike typical, you know, the brand that spends $10,000 on a sponsorship causes you a million times more headaches than the brand who gives you a hundred thousand. It's just.
Maricella Herrera:I remember that.
Denis Keane:So it's the ones who. I guess the 10,000 means more to them or something, I don't know. Because they're smaller, that they just demand so much more.
And the brands that come in with big money, they're just like, yeah, yeah, just, you know, make sure we get this X, Y and Z. So it's. It's an interesting business. So I did that for five years, but in the meantime, I opened another couple of restaurants and bars.
Maricella Herrera:So you were still doing.
Denis Keane:Oh, yeah, yeah, yeah, yeah, yeah. I said I. I have to keep moving. It's just that. It's that itch. That's why I couldn't be corporate, because I couldn't just do one job.
I have to have side projects.
Maricella Herrera:Is that always been the case? Like, after corporate, like, even when you were with the startup recently, were you still doing other things?
I know you still are an investor in restaurants.
Denis Keane:Yeah. And I, I've. I advise. Yeah, I still invest in some restaurants. Believe it or not, I might be investing one in Las Vegas pretty soon.
Maricella Herrera:Have you ever done outside of New York?
Denis Keane:No.
Maricella Herrera:So this would be the first time.
Denis Keane:This would be the first time.
It's a whole other long story about how it happened, but it kind of fell into my lap and I, I know somebody who used to work for me actually in the nightclub, who used to be. He actually was the front person who was the person who liked being the front person.
He happens to live in Vegas and I know that he wanted to get back into this business. So I knew somebody that wants out.
So I kind of at first thought I just kind of put everybody together and because my big fat mouth, I'm right in the middle of it. It looks like I'll be opening a place in Vegas in the next couple of months. So that's awesome. I'll take him on over. Yeah. Is it, is it though?
Is it hotter?
Maricella Herrera:Well, my own. Tell me, tell me, tell me why, tell me why is the, the. Is it though?
Denis Keane:Yeah, because I kind of thought I was, I got out of the bar business. Really? I didn't know. I really want to be working there on a daily basis.
It's still, you know, I don't know, my days of dealing with, you know, a drunk 25 year old, you know, is over for me. It's just. Yeah, for me a lot of it is. I've been there, done that so much.
If it wasn't for, you know, a friend of mine who lives there and now I kind of started the whole thing and it's actually my brother in law who wants to get out of it. So now I'm kind of like in the middle and I'm like, okay, I guess I'm doing this so I'm not looking, I'm not excited about it, let's put it that way.
I'm gonna do it, it'll be fine. But I'm not excited.
Maricella Herrera:When was the last time you felt really excited about opening something?
Denis Keane:But I did that tech, the last tech startup, one click. That was a lot of fun and that was really, it was the smart crew doing interesting things and working with AI.
I think AI is moving, we all know is moving so fast and people more my age are all afraid of it. It's like this. I don't want to do AI, I don't want to do anything about it.
e, that's just like saying in:I know what's going on. I'm not afraid of AI. So I think that's different for people around my age is to know that you can't put your head in the ground.
It's coming whether you like it or not, and you should stay on top of it.
Maricella Herrera:Yeah. I was going to ask you about this because I remember when we talked, you said that people still do ask you about AI adoption. And I just started.
I did it last week, the first workshop. But I'm doing kind of some work in that space of like, how do you get people who are very reticent and like, I don't want to deal with this.
It's going to take away the humanity, all these things. How do you get them to open their mind a little bit?
Denis Keane: always use that line. Like in:And I also try and tell people, like, listen, AI is not going to replace all the jobs. AI is going to replace the jobs of the people who don't know how to use AI. And sometimes I get people like the light bulb kind of like.
And I'm like, I'm serious. If you don't know how to use AI, you're going to get run over.
Unless you're doing, like, you know, if you're a plumber right now, until the robots come and take over. But if you have skilled labor, electrical, plumbing, things like that, at least for the next few years, that's safe.
But I think anything to do with numbers or writing or just anything else, AI is either better know how to use it and how to make yourself more productive that way, or you're gonna just. You're obsolete in a year from now.
Maricella Herrera:Just. It is scary.
I mean, I. I deal with people who also look at all like ethical concerns and the environmental concerns and all these things, and I get that. But the world is gonna keep moving, right?
Denis Keane:Yep. It's. We're not going back to the horse. Whether we. The way I look at it is it. It doesn't matter how I feel about us.
It's coming whether I feel it this way or not. I'd rather be in it and on it than watching it run past me.
Maricella Herrera:And nothing else happen. The way I've started to think about it with people who particularly ethical concerns around it.
Because I've been working with nonprofits in this space, and a lot of it is that, like, ethical. Ethical concerns is. I heard this in a podcast. I think it was like an evolutionary biologist saying it.
He was talking with some tech people and they were saying AI has an immense capacity for good. Right. And an immense capacity for evil or bad or however you wanted to say it. And so just like humans, Right, Just like humans. Exactly.
And so if you are concerned about it, then maybe it's better that you, the people who are concerned about the ethics, the people that are concerned about doing things in a way that will be good for humanity, maybe it's better that you are the ones on those trains.
Denis Keane:Right? I agree 1 million percent. You can't sit there and complain about something that you don't know about. Don't get yourself involved in.
You sit in the sideline. I don't like how you know you're not helping.
Maricella Herrera:No.
Denis Keane:If you're in there, the more ethical, strong people we can get into AI and on it, the better the odds are that the train will stay on track.
Maricella Herrera:Hopefully. Hopefully. Or at least we can try.
Denis Keane:At least we can try this. We can get our best. Yes. I think that's it. Right? We just have to give our best. I agree with you 100%.
You need people, good people need to be in on this and know what they're talking about so that they can have informed opinions on what comes next.
Maricella Herrera:Yeah, okay. That was. Our little AI went down. But no, but it's true. And I agree with this.
And it's gonna affect every single business and every single industry eventually. You know, like you said right now, maybe not electricians and plumbers, but wait till the robots are here.
Denis Keane:Yeah.
Maricella Herrera:Who knows? But it will.
Denis Keane:I'm convinced within five, six years, robots will be cleaning the house and making the beds and doing all those things. Now, that could be a great thing if people then can do a higher purpose and don't have to worry about menial tasks, menial repetitive tasks.
And hopefully that brings people to a higher plane.
Maricella Herrera:The purpose thing is, is difficult because as humans, we kind of need that. Right? We need meaning, we need purpose. We need wanting to do something. And if jobs.
And a lot of us not saying this is correct, but a lot of us get that from work. Although I've been trying to separate myself from that, but, you know, hard.
So then if AI is taking a little bit more of those jobs, you're gonna have to find that.
Denis Keane:Well, hopefully then we get more creative. Right?
Maricella Herrera:Hopefully.
Denis Keane:That's what I'm saying. Hopefully we as people instead of having to. Now I gotta clean my apartment today, my house, hopefully, then I have.
Now it's time to do, you know what? I want to paint. I wanna know how to paint, I wanna learn how to play guitar. Or hopefully it frees us up that we can do higher purpose things.
That's at least, that's my hope.
Maricella Herrera:Yeah, I agree. I hope so too. Going back to your story, I alluded to this question at the beginning and we kind of talked about it.
High level of how restaurant industry, nightclub industry, which I'm just fascinated by because I don't talk to a lot of people who are entrepreneurs, but in more of a brick and mortar situation, I tend to talk to much more tech entrepreneurs.
And I would love to hear maybe a story or something where you could see either the parallels with your experience in the tech world or how knowledge or experience or a story from your restaurant industry days helped you with that transferable skills in a way.
Because I think a lot of the people, especially now I've been talking to a lot of people who are looking for jobs, for example, and what I hear a lot is right now, if you don't say that you did the exact same thing that you are applying to do, it's very hard because people don't see those transferable skills. So I'm like trying to get to that.
Denis Keane:Right. I mean, at the end of the day, a business is a business. Right?
Maricella Herrera:Right.
Denis Keane:So restaurants have to run on numbers. You have to know. And there's a, and there's a million numbers to know. Right.
I got every, you know, your labor costs, your food costs, your alcohol costs, your rent, your insurance, your. I mean, I can go on, you know, you know, can go on and on, on with the whole P and L advertising, computers, everything you're. You're buying. Right?
So at the end of the day, it's still a business that, that comes down to numbers. And I'm a big stickler on. Again, you got to not, not just know your numbers, but you have to know where they come from, how they developed.
You know, it's one thing to say, oh my, my liquor cost is 20%, maybe is beer at 30 and your something's at. At 10.
You know, you got to break it down into the, to the least common denominator to find out, oh, there's a problem here that I didn't even know I had until I drilled down. So I think, you know, that's no matter what business you're in, is still a business.
People skills are very much required in biz in a restaurant because you have to deal with all the customers and more importantly, you know, people that are working for you, how you treat them, how you train them, what your, what your limits are in terms of firing somebody or give people second chances or third chances. So at the end of the day, people are people, no matter what business you're in.
And I actually find that somebody who's even bartended or been a server even for six months in a restaurant knows how to deal with people way better than just sitting in the corporate capacity because you see people at their best, you see them at their worst, and you see such a high volume with people that you kind of get your people's senses up quicker. So I recommend everybody, like when you're young, work for a summer in a restaurant or bar, you'll learn so much.
Maricella Herrera:I agree with that.
Denis Keane:People. It's a lot of multitasking, right? There's nothing linear going on in a restaurant. You're dealing with the lighting, the music.
Is that guy hitting on that girl and she doesn't want him to do that. When do you intervene? When do you not intervene? How's the food? How's the drink, how's the temperature?
So there's a lot of moving parts, which is just about every, especially startup. Every startup is just a million moving parts.
So I think it's the people skills, the business skills and knowing how to work and chaos are the three main things that probably helped me in startups. I think those are probably the biggest three skill sets.
Maricella Herrera:The people skills is underrated. I think I agree with you with the business is business regardless. And you need to know those fundamentals and you need to know those numbers.
I think people don't think about the people skills enough.
Denis Keane:I agree. I agree 100%. I think people, you know, like even this, when I went into this company, they never fired anybody.
And there was a couple of dead weights. You know, I talked to the founders a couple times and I was just like, you know, you have to have standards, right?
Because otherwise if somebody's slacking off, not doing their job, that does not motivate everybody else to do their job. Yes. So that's why, that's why I was saying to them a lot and they got it. And they know the first was like, how do we fire somebody? Can you teach us?
And you know, I went through like kind of a, you know, we played we role plays firing somebody and sucks, but it sucks.
And you know, and the worst thing is when you first fire somebody or when you first start doing it, some lot of times people can talk you into keeping them on.
Maricella Herrera:I can see that. I could see that.
Denis Keane:Oh, yeah. I remember the first time I had to fire somebody. I mean, she totally convinced me, like she would, you know, and she was terrible.
And I let her stay on and it was. And like, that was bad for the rest of the morale. Cause the rest of the staff was like, why'd he keep. You know. But I was young and I didn't.
I was maybe 16, 17, you know, working. Yeah.
Maricella Herrera:Very young.
Denis Keane:But as I said, it's a hard skill. And I've seen it where people are like, oh, give me another chance. And whatever. I think when you make. When.
Whenever you make up your mind and you've given them the chances, you know, you don't. I don't think you just go up to somebody and be like, you're not doing a good job, you're out. You have to have those conversations beforehand.
Here's what I expect from you. Here's what you should be doing by next week. I need to see this. You know, whatever it is done.
Once you do those chances and they still can't perform, then you have to. And I think that's critical, especially in the startup.
But I think it's critical no matter what stage you're at, because it definitely ruins people's enthusiasm to keep working there. If they say, you know, John doesn't have to do it, but I'm supposed to work harder. No, like I'm. I'll slack off to then.
Maricella Herrera:Yeah, so that's. I had some of that in my old role, in my old job. I remember that.
Not me, but like, I remember people feeling a certain way about one person who got away with a lot.
Denis Keane:And it ruins it. Right. It ruins that cohesion. It. You don't like. You might like almost everything else with the job, but that just gnaws at you and you just.
It just kind of ruins it. So. Yeah. And you got. So I think in a startup you want to start that right off the bat.
You have to, you know, high achievers who know what they need to do and you give them the tools to do it and expect those results. And if somebody doesn't, you got to part ways. Otherwise it just ruins the culture.
Maricella Herrera:I think it's the whole higher, slow fire fast. I can't remember who it was.
Denis Keane:Yes.
Maricella Herrera:That said that, but yes, higher, slow Fire fast.
Denis Keane:Yeah. As long as you're giving people the right chances and they know what's. And they know what's expected of them.
Maricella Herrera:You know, that clarity is very important.
Denis Keane:Right. And I've also had people where they just weren't right for that job, but I've been able to place them in another role that they did great at.
So sometimes it's, you know, it's not really their fault either. You gotta try and find that fit. But if you can't, then you gotta fire. You gotta move on.
Maricella Herrera:Yeah. You have to set them up for success or if not, then what.
Denis Keane:But I think too many people talk about that and don't live that.
Maricella Herrera:That's true. And you know, as I were talking about this, it made me think about how we were talking about AI.
People's skills are actually going to be one of the things that we're going to need 100%. Like. Like, yeah. If the machines are going to be doing all this, like more numbers. Right. Like.
Denis Keane:Like I said, like, ultimately we did. We took a lot of the manual work out of Consumer Insights.
So our pitch was always like, our AI could take care of all this manual grunt work that nobody likes to do. So you can work on your creatives and you can, you know, you can, you can work on a.
On a higher skill set thing because the AI is at least not for a while, is not going to be creative. So.
Maricella Herrera:Right. It's just.
Denis Keane:It should do a lot of the grunt. You should use it to do a lot of the grunt work and then it should leave us to be more creative. That's ideally anyway.
Maricella Herrera:What's one chapter of your life that people don't usually ask you about?
Denis Keane:I guess nobody really cares about how you were as a teenager, right?
Maricella Herrera:No, I guess not. I mean, I asked about what you wanted to be when you growing up. How. How were you as a teenager?
Denis Keane:I was pretty, I would say not nondescript. Kind of. Yeah. I was dorky and rather shy. Was not. I would never have done something like this.
Or if I did, I'd be a bright red face the whole time because I'd be so nervous and embarrassed.
Maricella Herrera:Well, honestly, I wouldn't have done something like this when I was a teenager.
Denis Keane:But I mean, I was very shy. I mean, like, I was very shy, got embarrassed very easily, was not outgoing. I had to kind of make a college.
College made me get outgoing and I faked confidence until I got confidence. Yeah.
Literally, like we just take a few deep breaths before I walked into a room and I would, like, push my chest out, my head up, and I'd like, I'm going to walk into this room with a big smile and super confident. And I would just do that even though I wasn't feeling confident or anything. And then after a while, once you kind of.
I don't know, you kind of fake yourself into getting used to it. And then people react to you when you walk in Confidential.
So then I became more confident because I was getting the good feedback up by acting confident. I can see that you walk in and you look confident and you pretend you're confident. And for me, it was just my chest out, head up.
That was my physical. You hit something physical. Yeah. But it made me like, okay, so at least I've.
I thought you need to do something physical to make your brain also change. So I kind of just forced myself to become social and be able to talk in front of people and be able to meet strangers. But by nature, I'm still like.
My wife would be like, once you get to know Dennis, he'll talk to you forever. But I'm not like the guy who walks into the room and I'm all over the place.
Maricella Herrera:Again, you were not the person who wanted to be the frontman of the bar, and yet you still have ended up with the history of your mom, but you did end up going into a rat where you still have to be very much around people.
Denis Keane:Oh, yeah. I mean, yeah, that's the way it worked out. But even when I was very shy, young, I work in the restaurant, but, you know, you don't have to really.
It's kind of a hello and what are you having today? And it's a lot of kind of run and gun conversations in a restaurant, in a bar. So I didn't have to get deep with anybody.
Maricella Herrera:Yeah.
Denis Keane:At least strangers. I didn't. Hey, how's it going? You know, good to see you again. It was easy to fake that kind of like, not fake it, but just be, hi.
You know, where I wouldn't be able to walk up to somebody, just be like. And get to, like, a whole big conversation off the bat kind of thing.
Maricella Herrera:It's interesting. I remember when. So in my old job, we did a lot of events, and I'm an introvert.
And I would always feel like when I was at those events, I was less of an introvert, not because I was out, like, talking to people, but because I was part of the organization that was putting on the event. People are coming to me, and I feel like that's kind of the same.
Denis Keane:Exactly. Even when I did it in restaurants, everybody wants to talk to the owner.
Maricella Herrera:Right, right.
Denis Keane:In event production, whoever's running the event. I mean, I would even have, like, celebrities walk up to me, be like, oh, I hear you're. You're running this.
You know, they'd either tell you what they wanted, or they might be like, yeah, sometimes, you know, they were. Other times they were just really nice. You did a great job. You know, love this, you know, thanks so much. Whatever. So, yeah, you're.
I was always pretty. I was always in a position where people sought me out.
Maricella Herrera:Yeah.
Denis Keane:Which is.
Maricella Herrera:That's the secret.
Denis Keane:Yes, it really is. Yeah. That's a good point. I didn't even think of that about that. But yes. Yeah.
Maricella Herrera:I would always joke that, you know, we ran, I ran a networking group. I was an introvert, and most of my team were introverts. And I think that that was why we were good.
We had the, like, extroverts like you that were like, like, you know, you had that person who was. But then everyone else was kind of just making things happen, and people would come to everyone.
Denis Keane:Cause even, like, for this last tech company, we have to go to an event, and we had to try and get people over to our table. Oh, shoot me now. Like my old college roommate, actually, I brought him in with this company also, and he, he could talk to anybody, and he's awesome.
And he'll walk up to any stranger and be just like, hey, how's it going? Blah, blah, blah. Hey, you know, I want to show you what we're doing over here. I, I, you know, I was, no, I'm not doing this.
Like, no, this is, I will never do this again. I will never come to one of these events.
Like, you know, on the one, you can come to me and ask me to come over, but I'm not going to be walking up to strangers. They're mid conversation. Excuse me. I wanted to introduce you to this company, not me at all.
Maricella Herrera:Yeah, same. Dennis, it's been so good talking to you, and I know we're out of time, I'm going to ask you my last question, which is always my last question.
If you could go back and tell yourself something, and I will say, because, you know, when I asked you about what chapter of your life people don't talk about when you were a teenager, what would you tell yourself?
Denis Keane:I would have given myself the advice. I said to you just to do it a lot earlier. Like, why was I so afraid to talk to anybody? Talking to a girl, Forget it.
That was just like a way as a kid or a teenager I couldn't do that. So I wish and I look back and I'm like, what was I so afraid of? They're just people just like me.
And I wish I had known to maybe value myself a little more or have a little more of that self worth that I didn't have and that I It's going be too long to get there. Or at least I I wish it had been earlier.
Maricella Herrera:That's good advice. I feel that way too. That's good advice. Well, thank you.
Denis Keane:No problem. Thank you.
Maricella Herrera:That's it for today. Thanks for listening. If you like this episode, hit follow or subscribe so you you don't miss the next one.
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I'd love to hear from you. Come say hi on Instagram at my job pod or email me at quitmyjobpod. Add GP Female Duck. See you next time.
