Listen to the Podcast About Uptown Social

Podcast for Uptown Social

Podcast Summary

In the latest edition of Eventful Endeavors, Mike Sherman of Felix and Fingers Dueling Pianos interviews Jeremy Rossi, the Chief Operating Officer of Uptown Social, a lively and dynamic venue in Michigan City, Indiana. Rossi is the driving force behind the highly regarded culture of Uptown Social and orchestrates multifaceted tasks that contribute to the venue’s exceptional operations.

Rossi’s role at Uptown Social extends beyond merely managing the operations. He becomes an intrinsic part of any event hosted at the location, from managing kitchen operations to serving VIP tables personally, thus playing an instrumental role in making each event a remarkable experience.

His tireless dedication and unique involvement at the venue create memorable experiences at each event. One such experience was ABBA Mania’s performance at Uptown Social. Rossi shares the fond memory of the incredible performance by the international touring band and the wide age demographic it attracted, enhancing the vibrant atmosphere of the Uptown Social.

Under Rossi’s leadership, Uptown Social continues to leave an indelible mark on its guests, creating an amalgam of great food, classic music, and a jovial atmosphere making it a go-to venue for diverse events.

If you are planning an event and have been searching for the perfect venue that exhibits a meticulous balance of professionalism and personability, Uptown Social is the perfect place to consider.

This interview was provided by Felix and Fingers Dueling Pianos.

Podcast Transcript

Mike Sherman (00:25)
Hey everybody, welcome to another exciting edition of Eventful Endeavors. I’m your host, Mike Sherman, with Felix and Fingers Dueling Pianos. This is of course the Easter edition of the show, which basically means it’s the one week of the year I can wear this brightly colored flannel shirt and people don’t give me weird looks. So for no other reason than that, this is the Easter edition we’re calling it today. I am here with a very special guest, Jeremy Rossi, who I’ve known for several years. He is the Chief Operating Officer of Uptown Social, one of my very favorite venues in Michigan City.

Indiana, he wears so many hats there every time I’m there I truly don’t even know what he does because he’s pretty much just doing everything He implements the SOP’s does all the behind -the -scenes stuff He manages the team culture and they have a big culture of values recognizing and generating high performance supporting innovation fostering growth I mean which is exactly the kind of things we do at Felix and finger. So I just love to hear that He went to Ball State University. I’m even learning this myself right now. This is great And he states that in his words he says

Jeremy Rossi (01:20)

Mike Sherman (01:24)
He’s founded an Uptown Social. Over the years, he’s mastered the art of event planning. He takes great pride in making someone’s vision come to life. And that’s absolutely what I see whenever I’m over at the Uptown, not sorry, Uptown Social. We just talked about that. It’s not the Uptown Social, it’s Uptown Social. I’ve done weddings over there. We’ve also done a lot of fun events where they just sell tickets and we just have like a fun dueling pianos night. So I’ve been over there probably, I don’t know, I bet six or seven times over the last few years and I always have such a great time. So.

Jeremy Rossi (01:36)
Word of that.

Mike Sherman (01:51)
Jeremy, thank you so much for joining us today. That was kind of the abridged version of everything you do anything else you want to throw in there that I missed out about kind of like what you do and who you are before we get into the fun stuff.

Jeremy Rossi (02:01)
God, no, hearing all that again, it’s like, oh yeah, I guess I really do all that. I mean, wherever I’m needed, that’s where I go. I’ve bartended, I’ve served the VIP tables for some of our large concerts. I mean, whatever it takes, I’ll do. So people are like, wait, you’re the COO and you’re serving our table? Like, that’s kind of cool. I’m like, oh, whatever it takes, you know, whatever it takes to keep the event going. And we want our events to go off without a hitch.

Mike Sherman (02:25)

Jeremy Rossi (02:31)
So whenever I meet it, that’s what I do.

Mike Sherman (02:33)
Yeah, and I always see, you do have some really cool names come through there. Just offhand, like who’s your favorite? Like what’s the coolest person or group or whoever you’ve had there that you’ve got to interact with?

Jeremy Rossi (02:44)
I think my favorite was when we had ABBA Mania here. They’re a national touring band, actually international touring band. And they do all the covers of our favorite ABBA songs. And the reason I like to, well one, I love the performers. I invited my grandfather to this show because he’s a huge ABBA fan. He even said, he’s like, wow, it was like watching ABBA like, you know, 30 plus years ago.

Mike Sherman (02:48)
Oh nice.


Jeremy Rossi (03:12)
And so he was shocked how good they were. I love the fact that for that particular show, the age demographic was so far spread out. So we had people in their 70s, we had people in their 60s. We also had kids in their 20s at the show because ABBA has kind of brought back some of their classic songs that everyone loves because of movies that have come out.

Also, TikTok is huge. There are so many artists that we haven’t heard from in a long time that are kind of coming back to us through social media. So I just enjoyed the fact that we had such a broad demographic at that show. I got to see everyone party and there for the same reason, just to have a good time.

Mike Sherman (03:42)
TikTok, I know, like, what’s the?

Yeah, that’s so awesome. Right, I mean, what is it? The, the, gimme, gimme, gimme. Like, I never even, I mean, I kinda knew that song, but then suddenly, like one day, even at our show, everyone’s just asking for this song, I was like, what happened? And it’s just like, right. You’re mainstream, right. I know, no.

Jeremy Rossi (04:11)
Well, so they did a TikTok dance. And once you do a TikTok dance, you know, it’s viral. So it would hit the mainstream again. Yeah. Like Kate Bush with running up that hill when it was Stranger Things. And then it was all over TikTok. And then she was like at the top, you know, of the Billboard charts. It was nuts.

Mike Sherman (04:20)
Yeah! Uh huh.

Right, I know. Well, that’s like the new one from, I forget the name of the movie it was in, but the Murder on the Dance Floor was just like in a movie and now suddenly it’s this like song that’s 30 years old and everyone’s like, oh, this new cool song. You’re like, no, it just kind of blew up suddenly. It’s just, yeah. Oh my God. It reminds me when, it reminds me of when, not High School Musical, was Glee, when Glee was on TV. Like suddenly like all these like 14 year olds are singing Don’t Stop Believing and like all these cool like classic hits. And it’s like, it’s just cool, you know? It’s a different world. Well, awesome.

Jeremy Rossi (04:43)

Mike Sherman (04:59)
So let’s talk a little bit about Uptown Social. How long have you been there? I don’t remember if I was ever there when you weren’t there, but I know a few years ago there was a transition, maybe an ownership, and a lot of changes were made. Talk to me a little bit about that.

Jeremy Rossi (05:15)
Sure. So I’ve been here going on five years. I was here, I started working here when the previous owners had Uptown. It was called back then, and when I started here, it was called the Uptown Center of the Performing Arts, which it was mainly a private event venue. I think we did maybe one or two public events a year. And that was just because of the restrictions of the liquor license we had at the time. We were just a catering hall, essentially.

Mike Sherman (05:40)

Jeremy Rossi (05:42)
So we have limitations on how many public events you can have with that type of permit. So with that being said, we mostly did weddings and we did a few fundraisers, things like that. But it was great. I love weddings. I’ve always loved being a part of weddings. I think it’s just a magical day and it’s all about this one couple that gets to showcase their love in front of all the people that are in their lives that support them.

You know, I love the idea of weddings. I think it’s important. And then when later on, you know, towards the end of the previous ownership, I started realizing, you know, there’s so much more potential here than just private events. So we really need to get into concerts and comedy shows. And because I saw I I lived in Vegas for almost five years. So I saw venues that were doing all these big shows and how much, you know, revenue they were bringing in because of that. And like, that’s revenue we’re missing out on right now.

Mike Sherman (06:31)

Jeremy Rossi (06:39)
And all we have to do is change a few things, add some more sound and light. And so I talked to the owners about this idea and they said, you know, we’re actually to the point where we want to retire and get out of this industry. So that’s great, but it’s not really for us. And so, you know, it was disappointing to hear that, but I was determined to make this happen, not only for the venue, but for Michigan city. Cause there’s really nothing like that out here.

Mike Sherman (06:49)



Jeremy Rossi (07:04)
I think Blue Chip was the only place at the time that was doing live entertainment. And then when things kind of transitioned over there, they stopped doing so much live entertainment and started doing more private events. So I was like, well, there’s a need for it out here for sure. Now I was going to find someone who’s going to kind of buy into the concept. So I met with these two gentlemen from Chicago who have houses in Long Beach and Beach Walk, which are got a good stone’s throw away from the venue.

And I met with them in our wheelchair at the time. And I just said, you know, this is what my vision is for this place. And I would love for you guys to buy into that, but I’m going to be honest with you. It’s, you know, this building was built in 1867. So there’s a lot of work that needs to be done. It was later on that I realized that we did need like a new roof and new gutters, a lot of brick work. Some of the ivy that was so beautiful was actually like destroying the building. So there was a lot of work to be done.

Mike Sherman (07:53)
Mm -hmm.

Jeremy Rossi (08:02)
And so I brought that to their attention and I was completely transparent and they said, you know what, I think, especially with all the new things happening in Michigan city, there was like this five year plan about the train station, the double track getting built, making this a one hour commute from Michigan city to Chicago. There were a lot of great things that were happening in the future. So they said, yeah, let’s capitalize on this now, get the renovation done before, you know, we get really busy.

So they bought it, they signed on the dotted line in February of 2020, which as we all know was right before the pandemic. So I was like, well, I couldn’t have predicted that one. But you know what? It ended up working out and they realized that because we needed time to do the renovation, there was a lot of work to be done. And as they were kind of, you know, doing the demo of it at the very beginning of it,

Mike Sherman (08:35)
Good timing, right?

Jeremy Rossi (08:56)
We realized, hey, you break down this wall, there’s a whole problem behind this other wall. And so it was, was a whole thing, but we were able to get it done. It was hard because it was hard to find materials at the time. A lot of places were shut down. So just like, for example, stall doors, having doors on your stalls was hard to get. We were able to get up in time, thank God. But we started the renovation in March of 2020 and we finished in August of 2020. And we had our first event.

Mike Sherman (09:00)
Yeah, I’ve been there.


Jeremy Rossi (09:24)
Um, coming out of the renovation, which was the Michigan city class of 2010 high school reunion. And that went really well. And then after that, it’s just been great ever since. Now it wasn’t perfect at the beginning. There were a lot of restrictions the state was placing on venues like us, you know, in terms of limiting your capacity, social distancing. Yeah.

Mike Sherman (09:41)

Just as far as COVID was concerned, basically? Yeah.

Jeremy Rossi (09:48)
Yeah, exactly. So, you know, yes, we got out of the gate, we opened, but then right after we opened, it was like, oh, you can’t have more than 50 people in your venue. You have to submit a floor plan to the state and you got to have social distancing and you have to mark how you’re going to have social distancing. And so it was we had to adapt. I mean, at one point I was like, if I get one more email or letter about the things you have to change in order to satisfy what the, you know, the CDC is recommending or requiring.

I was like, I’m gonna lose my mind because I’m like, how do we make money with 50 people, you know, in this 501 person venue capacity? And we did it though, we just thought of things, we did virtual stuff, we did smaller events that didn’t cost us very much. We brought back dueling pianos, which was when you guys came into play.

Mike Sherman (10:19)


Yeah, I remember the first one, there was still the restrictions and I remember like we have to do this and keep people apart and how they would get drinks and I mean everything, yeah.

Jeremy Rossi (10:41)
Exactly. And I remember like we chose you guys, um, cause we were uncertain, like how bands are to react to, Hey, we got to do this. We can’t have this many, we can’t have this many people, but, um, you guys have such a great reputation. Like you’re easy to work with. You do a great job, no matter what, you know, what the ticket sales are. Like you guys are in it to win it. And that show actually sold out. Um, it was such a great, it was the first time I ever got to put a sold out sticker on the web poster out front.

Mike Sherman (11:07)
Oh, I didn’t know that. That’s awesome.

Jeremy Rossi (11:10)
Yeah, it was really neat. I was, that was like a proud moment. I was stressed because that was our first public show coming out of COVID. And, you know, I want to make sure everything was, we were doing everything we were supposed to do. And it was a great show. You guys killed it. And I think we brought you back time and time again after that. And you guys always, I mean, you and Robert always do a great job and we always request you guys, not that your other, your other performers are amazing too, but we just have, we kind of built that relationship with you and Robert.

Mike Sherman (11:14)
Public show.

Yeah. Well, it’s fun to show up and know who’s there and just like, oh, hey, like, yeah, I like I know people. I’ve met them. It’s just it’s a different kind of experience. I mean, we look forward to getting there because we actually feel we have kind of like friends that work there. So it’s great.

Jeremy Rossi (11:38)
And we know that you guys.

You’re a –

Exactly, and our standards are the same. I mean, the expectation is the same. You know what to expect when you come here. You’re going to be taken care of, great hospitality, everything’s going to work well, you’re going to have someone there to help you plug into the system, no worries. Same with us. We know you guys are going to get here on time, you’re going to have great show. It’s just stress free. I mean, you guys really just make it to where our jobs are a lot easier when you guys are here, and you guys have a great show. So…

Mike Sherman (12:13)
That’s great.

Jeremy Rossi (12:15)
You know, all that being said, it’s been a roller coaster. I mean, I’m going on five years and I’m so glad that we’re in a position now that we can have sold out shows at maximum capacity. And that’s a great feeling. We’re actually coming back from that whole athlete week at the very beginning, which I the owners, I promise, just stick with me. It’s going to get better. And it has. So we’re doing great. We’re still doing weddings, but we’re doing a lot of concerts, comedy shows.

Mike Sherman (12:37)
Ha ha.

Jeremy Rossi (12:44)
drag shows, we’ve done 5Ks, we’ve done festivals, vendor fairs. We’re always, and that’s what I people too, I’m like, tell us what you want us to do and we’ll try to make that happen. Like.

Mike Sherman (12:55)
Yeah, well that’s the great thing about being in a town like that. Like in Chicago, it’s like you’re not gonna poll the city to say what do you want, you’re just gonna guess. But like, Michigan City, like yeah, you can be a part of the community and give the people what they need and want.

Jeremy Rossi (13:07)
Yep, exactly. That’s what we want to do. We want the whole point of this was to provide the community with something that they needed. Also, I should probably mention this, most of our events that we do benefit a local nonprofit. So we’ve donated lots of money to Stepping Stone Women’s Shelter, Interfaith Community Paths, which provides shelter for men, women, and children 365 days a year.

Mike Sherman (13:21)

Jeremy Rossi (13:34)
and we’ve donated to Doonbrook, which helps, which is a child advocacy nonprofit. Here in Michigan City, we’ve donated money to the Chamber of Commerce, several of the Aliveness Project, which provides free HIV and hepatitis C testing for our community, and Pride, PFLAG, and we’re always partnering with new organizations. Actually, I just partnered with…

Indiana Youth Group on some of our events, which they’re kind of, they’re mostly in Indianapolis, but they’re making their way into Northwest Indiana. And what they do is they provide shelter and support and counseling for LGBTQ plus youth who have been kicked out of their home because of their sexual orientation. And so they help them get a job and or finish their education.

And get them in a situation where they feel supported and loved. And when I met with Buffy Adams, who’s in charge of the Northwest Indiana part of it, she said that this was definitely something that our community needed. And I said, well, because we do a lot of sold out events and we do a lot of LGBTQ plus themed events, like Pride events, I said, I think we could give you the necessary exposure that you need.

to really make a mark here, let people know and raise awareness of what you’re doing for our community. So again, I put that out there because I want other people to reach out to me and say, hey, this is another organization that needs help right now. And we’ll try our best to partner with them to help raise awareness and some funding for them.

Mike Sherman (15:19)
Oh yeah, that’s amazing. That’s so awesome. I think some of what you’re saying sounds familiar to me, but I didn’t realize to what extent that was a big part of what your mission and everything you do out there. So, oh my gosh, that’s amazing. So yeah, well, so tell me this. So now you mentioned, obviously you still do weddings. How does it work at like a venue like yours that does concerts and things? Like, are you kind of booking the weddings and then filling in the empty dates with the concerts or do you kind of have selective dates? Like how does that generally work? Oh, cool.

Jeremy Rossi (15:26)
Yep. Yeah.

You’re 100 % right. The weddings are our bread and butter. I mean, that is where, that is why we continue to operate, you know, years later. Um, because yeah, that’s, that’s definitely our bread and butter or the wedding. So what we do is typically weddings are booked out a year in advance, not always, but for the most part. So what we do is we look at our calendar about three months out and we see what dates haven’t, that are still available that haven’t been booked by a wedding. And, um,

we’ll fill in those dates with concerts, comedy shows, you name it. So yeah, weddings are a priority. And especially because one, everyone here, all of our management team love weddings. And it’s not because they keep us afloat. It’s also because the people that we work with, these clients, they become like part of our family. And I know it sounds probably a little cheesy, but it’s true. We watch these couples at us on social media. We follow them.

see their journey take place here, start here, and we see where it goes from here. And they have their first house, they have their first baby together. We get to see all those milestones happen for them. And then they come back to the venue, they see us, they come to one of our shows. And it’s just great. You don’t really get that with concerts, you know, it’s mostly the weddings that we have that with, because we work with these couples for sometimes a year or more or longer.

Mike Sherman (17:02)

Jeremy Rossi (17:08)
because they booked so far in advance, which is great. So yeah, I would say what we do is we fill in the gaps with the concerts and public events, and then we make sure that our weddings get those prime dates, which in Indiana, especially in Northwest Indiana, your wedding season is gonna start around May and go into maybe mid -December. Actually, yet it gets iffy just because you don’t know if we’re gonna have a snowstorm in January or.

Mike Sherman (17:30)

Heh. Mm -hmm.

Jeremy Rossi (17:35)
you know, a hailstorm in February, you just never know. So typically January, February, and March, and April, that’s concert season, especially because those are the months that people want to be inside anyway. We are an indoor venue, so that’s really peak time for us to host those public events here. But yeah, so I would say if you, and we also have, which is kind of neat, April is going to be darts tournament month, so we’re…

Mike Sherman (18:03)

Jeremy Rossi (18:04)
Kind of interesting, we are hosting a darts tournament for the championship darts corporation, which we have never done before. We’ve never done a sporting event here. Um, but so this is the first, but darts is actually a big deal in Indiana, in the Midwest, I should say. Uh, there are a lot of darts fans out here. And so this opportunity came across my desk one day and I said, let’s, let’s do something with this. Let’s try to make it happen. So the president of the CDC, his name is Peter Satara came in.

Mike Sherman (18:10)

Jeremy Rossi (18:34)
and looked at the venue and said, yep, this is it. This is where we want to have our tournament. So it’s USA versus Canada. And that’ll be on April 12th and 13th. And it’s kind of neat because, again, we’ve never done anything like this before. But also USA versus Canada is kind of a neat thing to be able to host here.

Mike Sherman (18:43)

Well, even as you’re telling me about it, I’m imagining this just like guys coming and playing darts, but it’s like this is like a national, like this is like a big thing. It’s not, I mean, that’s very, very cool. Yeah.

Jeremy Rossi (18:58)
The Olympics of darts. I mean, it is a big deal. And so for us to be able to host something like that and Michigan City to be able to host something like that is kind of a big deal. And then the week after that, there is a movie being filmed here, which is also about darts. It’s called Bowls. And it is about a group of guys that play darts for fun at their local bar.

Mike Sherman (19:09)

So well.


Jeremy Rossi (19:27)
And you know, they’re kind of getting older and they say, you know what, let’s, let’s do something. Let’s do something fun. Let’s, let’s go play darts and let’s make this a thing and go into the darts championship and see where it takes us, see how far we get, you know? And so that’s what the movie’s about. Some hometown friends that decide they want to take it a step further and be a part of the darts championship world. And they go on to the championship and I can’t say anything more than that.

But so the last part of the movie, which is the actual darts tournament, will be filmed here. So we’ll be doing some B -roll footage during the actual tournament, and then the rest of the movie will be filmed the week after. And we’re not sure which streaming service it’ll be on, but as soon as it gets picked up, we’ll announce it to everybody. But it is neat to be able to be in a movie like that.

Mike Sherman (20:01)
Oh wow.

Yeah, well that’s all, and I totally believe it. I mean, someone walks in and be like, this is where it’s gonna be. I mean, the space is so beautiful. Like, everyone check out their website. I’m sure photos won’t even do it justice, but there’s these pillars, this stage with this, I mean, is it like a pipe organ? Or what is like this giant thing on the back wall? Is that what it is? I’m trying to remember correctly.

Jeremy Rossi (20:37)
Yeah. So I encourage people to like go to our website, UptownSocialMC .com. You will see a lot of our concert and wedding albums on there. So you can really see what Mike and I are talking about right now. You have to really, and honestly, the pictures don’t do it justice. You have to come into the space to really see what we’re talking about. But it is the original pipe organ. So this building started off as a church. It was St. John’s United Church of Christ in 1867.

Mike Sherman (20:53)
Yeah, it’s so cool.


Jeremy Rossi (21:06)
Now St. John’s is Down the Road from Us by Marquette Mall. And then it became the Canterbury Theater in like 1960s and then.

Mike Sherman (21:15)
Oh, and that I think I remembered. Yeah, reading a little about that. Okay, sure.

Jeremy Rossi (21:18)
Yes, they did plays and musicals here and then it turned into the Uptown Center in 2009 when the previous owners bought it. They did a small renovation on the building just to give it some paint, make it look good enough to be a wedding venue. And so they ran it as a wedding venue from 2009 to 2019. And then like I said, the current owners bought it in 2020 and turned it into a live entertainment. But…

So when we renovated, that was actually the idea was to maintain the historic character of the building, but give it that modern, you know, technology and look that it needs to be efficient and to be able to host concerts, you know, national acts, and also be able to compete in the wedding venue industry. So we did a lot of work. I mean, new, new, new flooring. We got a brand new ballroom floor, which I don’t think you’ve seen yet. So we did the entire ballroom floor in December of last year.

Mike Sherman (22:10)
Yeah, I don’t know.

I feel like I remember you telling me that was going to happen because that sounds familiar to me, but yeah, yeah. Oh my gosh, so cool.

Jeremy Rossi (22:17)
Yep. And it definitely happened. We were able to get some grant money to help cover some of the cost. And thank you, Urban Enterprise Association. And we got the floor done. But prior to that, when we did our full renovation, we had to extend the restrooms out. The old restrooms had, like, the women’s had two stalls, the men’s had one stall. So it was not great for large events. So we had to upgrade those. We had to upgrade the lounge, the flooring.

Mike Sherman (22:23)

Jeremy Rossi (22:47)
We did tuck pointing all the historic brick around the building, new roof, new gutters, new sun and light system. You name it, we probably did it, but we had to. And it was something that the owners were aware of and they were definitely invested in that renovation. So, but we maintained what makes the ballroom unique and special, which is the original vaulted ceiling, the columns that are in the ballroom.

the original pipe organ. So we refurbished that. It no longer functions as an organ. I’m sorry, Mike, you can’t play. We put the opera on it, but it is a great focal point for the room. It’s a great backdrop for our weddings. It’s a great stage for our bands to perform on. When they see that behind them, when they’re performing on stage, they just love it. We light it all up. We change colors. It’s really neat. So that was the idea, was to preserve what makes this building special, which is the history.

Mike Sherman (23:33)
Yeah. Yeah.

Jeremy Rossi (23:45)
the history of it.

Mike Sherman (23:46)
Oh yeah, it’s such a beautiful space, really one of the most, I remember my first time there too, yeah, because we were up on that stage for wedding and I was like, what is this? Like, where are we right now? And that was before any of the renovations. That was probably back in, that was the old owners, so yeah. Well, awesome. Well, before we wrap up, there’s a couple things I just wanted to put on here to get a little info on. I’m just gonna lay in both that right here. You say, and I read too, that you were the Michigan City 2023 Young Professional of the Year, which is so awesome. So I wanna hear a little bit about that.

And then I also want to hear, I know you say you got engaged recently, which is super exciting. I can’t remember if I knew that or not, but I’m very excited and happy for you. What’s that like being engaged and like planning your own wedding as somebody who actually knows so much of the ins and outs of the industry already? Because I know when I got married, it was before I was in the wedding industry. And I’m like, I would do things a lot differently now. So yeah, young professional of the year and wedding. Talk to me a little bit.

Jeremy Rossi (24:38)
So yeah, I’ll start with the engagement, then I’ll talk about getting professional of the year and how that kind of ties in. So one, I get that question all the time, is what’s it like planning your own wedding when you have to plan other weddings? And I said, well, it creates an expectation, honestly, because now the guests I’m inviting kind of have this expectation this wedding’s gonna be like, full blown, decorated, like all these great things because it’s what I do. But I…

Mike Sherman (24:50)


Jeremy Rossi (25:06)
I prefer simple. Simple and elegant is what I like. I don’t like over the top weddings. I will do them and I’ll do a great job and I’ll help people plan those over the top weddings. I think it depends on people’s personalities, what they choose. I’m a minimalist, so I don’t need a whole lot. I just want my family and friends there and I want to have some great music and some good food because that’s what people remember. They remember the venue. They remember…

how the parking situation was. Which we have great parking. And they remember the food and they remember the music, you know? And so those are the key components that I want in my wedding. When it comes to decor, not super concerned about it. People keep asking me, are you gonna have it at Uptown Social? Which I’m still not sure, you know? And the reason being is I love my venue and I fell in love with it the moment I walked in the door. But at the same time, I don’t want my wedding to feel like work.

because I know how I am when it comes to those little details. So I’m gonna be walking around checking everything, make sure everything’s perfect. And I don’t wanna have to feel like I have to coordinate my own wedding on my wedding day. So.

Mike Sherman (26:03)

Well, honestly, it’s like if I’m getting married, I don’t want to know where the garbage is going. Like, I don’t want to know where the dumpster is. Like, where the, it’s like, just like, I want it to be magical. Like, that stuff isn’t happening. So yeah, I totally, totally get it.

Jeremy Rossi (26:20)
I don’t write.

Exactly. So that was my thing. And I’m not saying I’m totally counting it out. You know, I love the venue and it would be cool to get married at the this venue that I helped build and rebranded and did a lot of work on. And it would be it would kind of be like the capstone of everything that I’ve done is, hey, like I brought all this to fruition. Now I get to experience it for myself as a client. But I haven’t.

Mike Sherman (26:41)

I’m not joking, I’m getting little emotional hearing it, because it’s a cool thing.

Jeremy Rossi (26:53)
It is, it would just be like the epitome of everything that I’ve worked for and to be married on that stage, it would be special. So, you know, a lot to consider, but the engagement, that’s the part that I’m really enjoying right now. I tell people, I’m like, I just wanna like, I just wanna enjoy this part of it. You know, I don’t wanna get into, okay, we gotta plan the wedding, let’s get our guest list going. I just wanna enjoy this moment a little bit longer.

Mike Sherman (27:14)

Jeremy Rossi (27:22)
And so that’s kind of what I’m kind of doing right now is I’m putting everything aside and just focusing on being engaged and then I’ll get into the planning. We’re looking at May of next year as our date. Haven’t confirmed anything, but I am weird with numbers. I’m looking at 5, 10, 25, because I like numbers or numbers divisible by five. It’s a weird thing, but it’s just it’s important to me. So, but so with that being said, the engagement.

Mike Sherman (27:39)
Oh, I like that. Sure.

Jeremy Rossi (27:51)
was the best part. So the guy that I’m engaged to, he brought me, he bought tickets to a concert. One of my favorite bands, one of our favorite bands is the Nicotine Dolls and they do a lot of covers. They have a lot of great originals, but they cover one of our favorite songs, which is Simply the Best by Tina Turner. And it was like, they had a set of 12 songs. I think it was the 11th song that they performed. So this whole, I had no idea, people like,

Mike Sherman (28:11)

Jeremy Rossi (28:19)
Do you know what was gonna happen? I had no idea. I thought we were just going to a concert and dinner and going home. I had to work the next day so I couldn’t stay out late. So I didn’t think anything was gonna happen. And the song comes on. I’m recording the show and he said, put your phone down. I’m like, what do you mean? Just put your phone down for a second. I’m like, all right. And then as it gets to the chorus of the song, he gets down on one knee and pulls out the ring and poses right there.

Mike Sherman (28:26)

Jeremy Rossi (28:46)
and all these people are around us watching this happen. I’m in shock and I’m like, is this really happening right now? I actually said is this really bleeping happening right now because I was in such shock, which probably like ruined the moment. But, and I just got choked up and I cried and it’s one of those things, it’s hard to describe when you get proposed to. It’s really, and not to sound like this is a fictional novel, but it feels like time just kind of stopped for that one second.

Mike Sherman (28:52)


Jeremy Rossi (29:14)
You don’t hear, I stopped hearing the music when he proposed. All I heard was what he was saying. I saw the ring and I reacted and got excited. And then when he stood up and put it on my, put it on my finger and stood up, that’s when like everything, you know, someone pushed play again and everything came into perspective. And my only guys got engaged in this crowd of 500 people. Uh, so it was, it was special. He definitely did it the right way. I was shocked.

And I was very happy that it happened because, um, you know, this is definitely my soul mate. This is the person I plan on spending the rest of my life with. But, and then when I got nominated for the unprofessional of the year award and became a finalist, it was even better because he was in the audience when I accepted that award that night. So it felt really great. I had engaged like maybe a week or two prior to that. And then the award dinner, the awards dinner happened.

Mike Sherman (29:42)

Ha ha.


Oh well.

Oh my gosh.

Jeremy Rossi (30:11)
and they said my name and I look in the audience and he’s sitting right there with a big smile on his face, so proud of me. I’m holding my little trophy and I’m just thrilled and just having him there to support me was everything. So that’s kind of how it all ties in together. The last 30 days of my life have been insane. I got engaged, won Young Professional of the Year for…

Mike Sherman (30:16)

So this all literally is in the last month. I was gonna ask, when did all this happen?

Jeremy Rossi (30:39)
Yeah, because the Chamber of Commerce is the one who, they’re the ones who create those awards and do the whole dinner. So they do it typically in February of March of the following year. So they have an entire year to see every, you know, how, cause there’s like small business of the year, there’s large business of the year, there’s unprofessional of the year. There’s a few different awards. And so what they do is at the end of 2023, that’s when they do the nominations. And that’s when the committee decides on who they want the finalists or the.

the finalist to be and then who the unprofessional of the year is going to be. So yes, this all happened within the last 30 days.

Mike Sherman (31:15)
Wow, that’s amazing. Wow, that’s like such an exciting month. That’s so crazy. I mean, oh my gosh.

Jeremy Rossi (31:19)
March has been a very exciting month. And then we had St. Patrick’s Day this month and we got to go out and have fun with that. But it was just so hard because right after that, I got engaged. Like the next day I had to be at work, we had a show the next day. So I had to hurry up and come back from Chicago, go to work. So we didn’t even celebrate it. So then the following week we actually got to celebrate it and that was really nice. So it’s been a crazy, crazy 30 days. And…

Mike Sherman (31:31)


Thanks for watching.

Jeremy Rossi (31:45)
When you guys reached out to me to do this podcast, I was thrilled because one, I haven’t seen you in a while and I know you’re doing all these great things. And as I figured you would be, and, um, I follow you and Robert on, on Facebook. And so I’m really happy that we got a chance to, to touch base. I know it’s on a podcast, but it’s just, it’s just great to chat a little bit and, um, see how we’re, how we’re doing and, um, get to share my experiences with you because it’s been like.

Mike Sherman (32:06)

No, I Love it. No you this was easy. I didn’t barely had to say anything I mean, yeah, you’re you you’re I was gonna say we get we could keep this going for another two hours probably right now But oh my god. Well, really yes, sincerely. I agree. I’m so happy what congratulations one of the amazing month This has been one of the amazing five years. It’s been I mean really the transformation of Uptown social is just phenomenal and it’s every time I go there It’s so cool to see what’s new and what’s different and what’s changing and it’s also just been great to see the same people there for

Jeremy Rossi (32:14)

Oh, I can talk for an hour.

Mike Sherman (32:39)
for so long too, you know, it’s just like, it’s great. It’s unusual sometimes with a venue for, you know, for me to be there for so many years and to keep seeing the same familiar faces. So it’s, yeah.

Jeremy Rossi (32:43)
It is.

It’s highly unusual. Even our bartenders and bar backs and security, I mean, they stay with us. A lot of them have been with us since day one, but I feel like that shows if you take care of your employees, they’ll take care of you. And they’ve been with us for years now and we’re a family. I mean, we stick together. So thank you for noticing that though. Yeah.

Mike Sherman (33:05)
Yeah. Absolutely. Yeah, no, I mean, yeah, it really does. It really does show a lot about everything you all do, or you personally, and then just the rest of the people working over at Uptown Social. Well, yeah, well, great. Well, thank you so much for chatting with me today. It’s been so long. I know. I know, right? I know. We were just cruising here. Well, once again, everyone’s… Oh my God.

Jeremy Rossi (33:17)
Thank you.

That was the fastest 30 minutes ever. I can’t believe it’s already been 30 minutes. Like, holy cow. Well, it’s just too long before it’s catching up. So that’s what it’s like. That’s what it felt like.

Mike Sherman (33:30)
I know, I know. No, it’s great to see you and chat with you and hopefully we’ll get over there soon and get to do it in person. But once again, thanks everyone so much for listening. This has been Jeremy Rossi, the COO of Uptown Social in Michigan City, Indiana. Like I said, definitely check out their website. I think we even have a promotion. What do I have here? I said, yeah, if you reach out, is it if they reach out by June 1st, you’re gonna give them 10% off? Am I saying that correctly?

Jeremy Rossi (33:36)

As long as you hear from them by June 1st, it’s 10% off the venue rental fee. So if you’re booking a Saturday here for maybe a birthday or a wedding or what have you, 10% off our Saturday venue rental, which is typically $4,000. That’s $4 off. So it definitely saves you some money. And we do different pricing based on the, if it’s Monday through Thursday, it’s one price. Friday and Sundays are one price.

Mike Sherman (34:12)

Jeremy Rossi (34:21)
And if it’s a small wedding, we actually just rolled out this new thing where we are doing elopement slash micro wedding packages, because we’ve noticed the trend lately has been more intimate ceremonies. So we’re all about that. And if you want to get married here with 50 people or 75 people or less, we have a couple of different options for you. We have a beautiful courtyard you can get married in. We have this beautiful 9th Street gated.

Mike Sherman (34:30)

Jeremy Rossi (34:48)
extension of our courtyard that also turns into a patio. So we have areas within the venue that you can get married in for 75 people or less. So if you’re interested in doing anything like that or if you just want us to do a custom proposal for you, go over bar package information, whatever, we’re there for you. You can also schedule a private tour to come in and see the venue for yourself so you can see exactly what we’re talking about right now.

And again, we’ll do a custom proposal for you and go over some available dates.

Mike Sherman (35:20)
Great, that sounds amazing. Well, I definitely encourage everyone to check it out, even if you’re just curious, go to their website, reach out to Jeremy directly. I know we’ll have all the info posted, but I know you can email them at So once again, everyone, thank you so much for hanging out with us today on another exciting episode of Eventful Endeavors. I am your host, Mike Sherman, with Felix and Fingers Dueling Pianos, and we will talk to you all very soon. Thanks so much, bye.

Jeremy Rossi (35:34)
Got it.

This interview was made possible by Felix & Fingers Dueling Pianos

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