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Should Every Restaurant Have a $5 Beer? Plus the Industry Tipping Point, ADHD as a Superpower, Frequency always wins

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About this episode

Josh, Mike, and Matt sits down with Keith Benjamin, nightlife operator and co-founder behind Uptown Social, Share House, Bodega, By The Way, and The Waverly, for a conversation about betting big, building brands, and turning hospitality into a true long game. Keith shares how his journey started with Penn State tailgates, fraternity social life, and bartending in New York before evolving into ownership in iconic Manhattan watering holes like Stumble Inn and Hair of the Dog. From there, he opens up about the leap to Charleston, why he saw an opening in the market, and how Uptown Social became the kind of unicorn venue most operators only dream about.

The conversation then shifts into the realities of nightlife economics, including the now-infamous $9 Modelo debate, how serious operators actually think about pricing, and why beverage-first businesses can be so attractive compared to labor-heavy food concepts. Keith, Josh, Matthew, and Michael dig into frequency, guest behavior, hospitality, and the brutal cost structure of modern restaurants, all while reflecting on what makes certain places worth returning to. Along the way, Keith talks about entrepreneurship, ADHD, risk-taking, and the compulsion to keep building, offering a clear look at the mindset behind one of Charleston’s most successful hospitality operators.

Links and resources 📌

Visit meez: https://www.getmeez.com

Follow meez on Instagram: https://www.instagram.com/getmeez

Follow Josh on Instagram: https://www.instagram.com/joshlsharkey/?hl=en

Follow Josh on LinkedIn: https://www.linkedin.com/in/joshua-sharkey-406965b/

Follow Keith on LinkedIn: https://www.linkedin.com/in/keith-benjamin-4bba57396/

Follow Keith: @keithbenjamin

Follow Bodega on Instagram: @eatdrinkbodega

Follow Uptown Hospitality Group on Instagram: @uptownhospitalityevents

Follow Michael: @michaeljacober

Follow Matthew: @conbeazie

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What We Cover

03:13 Michael Jacober Introduces One Of His Oldest Friends

05:37 From Penn State Tailgates To Bartending In New York

10:03 The Stumble Inn Era, Golden Handcuffs, And First Ownership

16:39 Why Keith Left New York And Bet On Charleston

19:44 Opening Uptown Social And Building A Nightlife Unicorn

23:41 Bodega, Share House, By The Way, And The Waverly

30:10 The $9 Modelo Debate And The True Cost Of Doing Business

54:22 Beverage-First Concepts, Margins, And Why Frequency Matters

01:14:06 Why Hospitality Economics Are Reaching A Tipping Point

Transcript

Keith Benjamin (00:00.105)connecting them because it's gonna be 80 degrees here this weekend, which is quite nice.

Josh Sharkey (00:04.826)It's wild that like it's ice today and like literally it's just our whole our whole driveway is ice and I think it's gonna be like 65 on Sunday, which is good. My daughter's birthday is on Sunday and my wife planned an entire outdoor outdoor camp birthday. I live in Westchester, so in New York. I know if you know the area.

MJ (00:07.702)come on.

Keith Benjamin (00:21.309)Where do you live, Josh?

Keith Benjamin (00:27.015)I do, I do. I moved from New York City eight years ago.

MJ (00:31.436)no, something's not working.

Josh Sharkey (00:32.897)Are you from New York?

Keith Benjamin (00:34.727)I'm from Short Hills, New Jersey.

Josh Sharkey (00:37.371)alright.

Matthew (00:37.78)A Rangers fan!

Keith Benjamin (00:39.623)Yes, not the best year to be a Rangers fan, but we're okay. Yeah, yeah, we'll be back. I'm in Charleston, I'm down the road from Matt.

Matthew (00:44.63)Love them anyways.

Josh Sharkey (00:48.174)Where do you live now?

Josh Sharkey (00:54.159)I'm sorry about that.

Keith Benjamin (00:55.466)Yeah, he followed me down here. didn't even know it.

Matthew (00:59.512)Whatever Keith does, I follow. Sounded like a good idea. No.

Keith Benjamin (01:01.395)There you go.

Josh Sharkey (01:01.754)Did you guys know each other before Charleston?

Keith Benjamin (01:05.191)We met, we met, gosh, when did you move here, Matt?

Matthew (01:09.496)2020. March.

Keith Benjamin (01:11.035)Yeah, we met shortly after he moved at another local wine shop. Not his, but a place that he likes to spend time.

Matthew (01:20.736)And he's known Lonnie Sweet forever, so we connected because I knew of him in New York because of Lonnie Sweet. So there was the connection to say hello. But here we are. All four of us. MJ, I haven't heard a word from you yet.

Josh Sharkey (01:24.314)I'm bunny.

Josh Sharkey (01:30.722)I love Lonnie. He's a good dude. Mike, you have Riverside open in two.

MJ (01:35.932)Yeah, I closed it. There's something. I switched. No, I don't. wait. Yep.

Josh Sharkey (01:40.922)You just have two tabs open. That's all.

Matthew (01:46.274)Keith, just so know, every week we do this and Michael's lost every week.

Josh Sharkey (01:50.104)Yeah, he's got like all this fancy equipment

Keith Benjamin (01:51.433)And I would argue he's quite the tech savvy individual. this is, this is.

Josh Sharkey (01:55.961)He's got all this fucking fancy equipment and every week it's a thing. It's like the sound or the... And he's surprised every time. I don't know, it doesn't work.

Keith Benjamin (01:58.575)Yeah, this is surprising.

MJ (02:04.87)No, no, I don't want to fucking hear it. I don't want to hear it. What I don't what I don't love right now.

Keith Benjamin (02:04.905)I'm in the middle of a sh- I'm in middle of a shithole, Arthur.

Matthew (02:07.613)I don't want to fucking hear it, he says. Enough out of you two.

MJ (02:13.798)side browsers and something's not right, can tell something's not right.

Josh Sharkey (02:17.338)What do mean?

Josh Sharkey (02:21.028)Hold let me see, alt check.

MJ (02:21.584)I see some shit on my screen that says close your other Riverside tabs, which I don't have another tab open. Sorry. And I have, I can see that something's uploading.

Josh Sharkey (02:26.874)You're really cursing a lot too, just saying. Like, jeez. God.

you may have... I think you're fine. It doesn't say it on my end, so I think you're good. You're good. Okay. Alright, gentlemen. Welcome to another week.

MJ (02:35.822)I don't know. This doesn't-

Okay.

Josh Sharkey (02:49.54)Two of you already know our special guest today, is that right? Mike, can you introduce Keith? And also, is it Benji or is it Keith? Because they started texting me, hey, Benji's going to come on. I'm who the fuck's Benji? You said this guy, Keith. Anyways, Mike, tee us up, please. Do some work this week.

Matthew (02:50.007)I'm ready.

MJ (02:54.172)Yes.

MJ (03:13.873)I'll do a little intro and then I'll also have Keith do a short intro as well. I'll start by saying Keith Benjamin is one of my oldest friends. I've known Keith since we were eight years old. We met at summer camp when we were eight. He's

He's a best friend who I have not only known since eight years old, we've sort of grown together throughout our lives. We ended up going to college together. We played on the same college lacrosse team. And then somehow we ended up in the same industry and have just shared so much with each other over the years.

I married Keith to his first wife and then I was the best man at his second wedding. I consider him one of, if not the most near and dear person to me personally. And on top of that, he is an absolute rock star at what he does.

He has been in the bar and restaurant business for I don't know how many years. We're obviously going to find out very soon. And he's done it at a level that is very elite. I would argue that Keith is one of the top bar slash nightlife operators in the country. And I am

Absolutely honored and thrilled to have him join us today. So I think what I want to just start with is Keith, can you just give like a little bit of background on how you ended up in this industry and basically what you've been up to for a little bit over a decade and a half?

Matthew (05:35.136)Night life, baby.

Keith Benjamin (05:37.305)Yeah, that was quite the intro. Thank you, Michael. Yeah, he and I go, Michael and I go way back, way, way, way, way, back. And it's a treat to be here with him today and you guys. Yeah, know, Mike and I went to Penn State together. It's no secret that Penn State's a party school and

And as lacrosse players, we knew how to find that party. And there's certainly some backstory that's relevant here. know, when I got to Penn State, I walked onto the lacrosse team, but...

But genuinely I wanted to go there because I wanted to be a part of something that was on such another level in terms of the pageantry of a big 10 college campus and what comes along with going to a school like that. And a big part of that is the party scene. I immediately kind of became enamored with this big kind of Greek life presence and tailgate.

on eight Saturdays a year at Penn State. I rushed a fraternity while I was trying out for the lacrosse team because I didn't know how things were going to shake out. I ended up making the lacrosse team and getting a bid to my fraternity the same day. When I started pledging, I became the apprentice to the tailgate czar, which was actually a real thing. We were working in college. Michael used to come to our tailgates, but we were working with close to $100,000 budget.

MJ (07:12.136)Okay.

Keith Benjamin (07:19.839)for every football season. And that was money that was contributed by the brothers, there were some alumni funds, et cetera. But each Saturday, we would get 100 cases of Natty Light.

and we would go to the local supermarket and we would do a shop for, call it three, $4,000 worth of food. And we would go back to the fraternity house and we would prep all of the food and put a lock, we would put a chain lock on all of the reach-ins because the brothers at one or two o'clock in the morning would try to get into the tailgate food and they'd want to grill it up before we even got up the next morning.

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