Lessons from 2 CEOs That Started From Scratch

0:00I've done everything here from fix the espresso machines to plunge the toilets to everything. on that because I talk about this at VaynerMedia. The reason I'm always calm is I know if David starts a coup and takes every employee with him, I have no fear because I know how to do every job. I think a lot of entrepreneurs make that mistake. VaynerNation, I'm extremely excited. I'm actually excited because visually this will be an interesting episode as well, so go check YouTube if you want to watch this one because we're in this incredible setting here in Midtown Manhattan with a fellow entrepreneur from the East Coast I admire very much, Gregory's Coffee.

0:35I actually tell the story pretty often when I talk about VaynerMedia, like how we moved offices, and Gregory's Coffee is actually in that story. Because when we moved to 23rd, 24th and Park, literally every day, it was kind of like when we started to somewhat grow up into like the alpha, not just complete scrap in the mud ridiculousness of the first couple years. Every day there'd be 100 Gregory's Coffee's Cups because everybody would go downstairs multiple times a day. And so we are here to talk to Gregory from Gregory's Coffee, really talk about entrepreneurship, his journey. I want you to know about him because I think a lot of you actually should be going on a similar path.

1:13And we're also here to talk about the incredible VFriends, Gregory Coffee's collaboration. Gregory and I just did Good Day New York, but we're really excited about the Jolly Jacko pumpkin spice chai latte collab that we're doing that's running here in October. So if you're visiting New York City, get to a Gregory's, find a Jolly Jacko beverage, pick up a collectible sticker, flip it on eBay or whatever else. And so I've just been really fun. We're about a weekend seeing all the tweets and the pictures of people having this cup in their hand, the QR code. We'll get into all of that and more. But first, let me say hello to Gregory.

1:45How are you, my friend? I'm doing well. How are you? I'm good. Why don't you tell the Vayner Nation a little bit about yourself? Literally comic book number one. Take the floor for two, three minutes, four minutes. Where you grew up. What kind of kid were you? just give us the zero to day one of opening your first Gregory's kind of story. Let's ground you for the audience. Son of an immigrant, you know, my father came here from Greece at a young age. Both my parents are from Brooklyn. That's where I started my journey. Sort of grew up in this sort of New York entrepreneurial household. So my father was a serial entrepreneur, left college to pursue his dream, which was running his own business.

2:20So he was working at a donut shop at the time. When the opportunity was there to take over that, he decided to leave school, take over that donut shop, and that was the first of his many forays into the food and beverage world here in New York City. Where was that donut shop? That was all the way down in Bensonhurst area. I believe it's still there, but it's probably changed names quite a few times since then. But he went on from donuts to the classic New York City delis you probably saw all over the city in the 90s. They sold everything. When I was probably in my teens, he had launched this panini press sandwich concept, which there was about seven of them at their peak.

2:52So I sort of I grew up watching my father grind every day. You know, I probably didn't see him as much as I would have liked, but that was the deal back then. Plus, like, not as convenient now with phones and connectivity. So definitely loved my summers, going to work with him. Tell stories of when I was seven. He used to have me down in Lower Manhattan doing deliveries for him in the summer. So he had a store down by Wall Street. He'd send me to send bacon, egg, and cheese and coffee across the street, and I'd show up with my Yankee hat, little kid, and these people would be surprised to see their delivery boy probably being in second grade.

3:24I have a son who's now eight, and I could never imagine him letting him loose in lower Manhattan, but my father thought it was a good idea. You got good tips, right? I got some tips. I mean, inflation at the time. I probably got two bucks, and I thought I was the richest guy in the world. But at the time, I didn't realize what was happening, but my father was sort of giving me a lot of the tools that would later help me in life, which was, you know, showing about hard work, dedication, all the experience in F &B. So, I mean, my whole life is not necessarily about F &B, but it has really been the fabric.

3:56Were you a good student? I was. Okay, so you were getting good grades, working for dad's stuff. My dad, also, immigrant family, good grades were, that was it. A real thing. It was like, you know, if I got a 97, it wasn't great. It's like, what'd you get wrong? You know, I got very fortunate. I got very bad grades. And I was born in the Soviet Union. So I'm like first gen. And my mom would ground me, but there wasn't that, which is so common in immigrant families. My mom didn't play that game. She had a different point of view that I had it, and she wanted me to be accountable to bad grades. But it's really been interesting, as I got older, I didn't realize that I was in an incredibly small minority of immigrant families where the mom and my dad worked, like sounds like the way your dad did, and my dad wouldn't have known if I got A's, F's, or Zs or Ws.

4:43I had no clue. But my mom, she grounded me for every bad report card, which was four times a year. The summer one, she was lenient a couple of days and I'd go out and play. So the pressure to get good grades was there. Yes. And did school come easy to you or did you have to really work at it to get those 97s? It's odd to say, but it did come easy to me. I ask it that way because there are just a lot of people who are naturally good at school. They understand the system. They understand what they need to do. I was able to achieve good grades. I was, you know, top of my class even in college in the honors program at Boston University undergraduate business school Ironically, I was about to reference my brother AJ who barely worked and got great grades and he went to BU as well Oh really?

5:24So maybe there's a trend there I did enjoy my time at BU, but also probably the one time it caught up with me was law school where I was able to Manage time and you know get the grades. I always expected but then I get to law school and the workload was so much more, I couldn't just approach it the same way I had done previously. So when I went to, got to law school that first semester, when I was getting towards finals, I was realizing it was a little different. I still wound up doing well, but it was just, for me, it was a transition as to how to approach it. And that was probably the most pivotal time for me learning that I couldn't just rely on natural ability that, or, you know, ability to kind of recall things, think through things.

6:04Law school taught me, you have to work really, really hard if you want to achieve what you really expect to. It also taught me about writing and a lot of things that also, for whatever reason, in business and all these things, business school wasn't as critical. Did you go to law school thinking you were going to practice law? I did. You did? Yeah. Oh, interesting. Go ahead. So again, I went to school not thinking I was going to work in the food and beverage industry. It wasn't necessarily cool back then. Yeah, it wasn't. You'd go to work for my dad. I'd come home smelling like with ripped jeans, but not because it was cool, because they got caught on a nail at work, you know?

6:37And it was like, you know, not glamorous. You know, I admired my father, but it wasn't something that I... You thought there was almost like most immigrant families, when dad or mom is working in that environment, there's almost this subconscious, if not outwardly conscious conversation of like, well, you're going to use this as a stepping stone, and you're going to do this more bougie thing. Oh, my mother cried when I told her I wasn't going to be a lawyer. Cried. My grandmother, years after I completed law school and I was working at Gregory's, used to call me her grandson, the lawyer. Because they were that mentality of office job, professional.

7:12Whereas the stigma about being an entrepreneur, but an entrepreneur in the food business did not have the same sort of cachet. I tell a lot of kids now, you can't imagine what being a chef means today compared to 25 years ago. Being a chef 25 years ago was the help. Exactly. Now there's celebrity chefs and the culinary explosion in our society, and that's wonderful, thank God. But to your point, I'm very aware of... It seems crazy. How long ago was this? When did you start, Gregory? 17 years. Yeah, I mean, it's just actually profound to think about entrepreneurship and food and beverage entrepreneurs rebranding in our society today as completely the other side of the pillow.

7:55I think it started with fast casual. Yeah, I think that's right. Literally the nomenclature getting away from fast food, where you could start saying things that people used to associate with just quick service, grabbing a salad, grabbing a coffee, to now it's an elevated experience. And they started designated as fast casual or fine casual, whatever it was. But getting away from, oh, it's just like another, you know, deli, you know, McDonald's-esque type business. So you're in law school. Yeah. I assume there's the great entrepreneurial story. Like, what's the moment that you're like, fuck this, I'm doing Gregory's?

8:29I was working my first law job first summer after school. They offered me a position. And I kept saying to myself, I can do this job. This then kind of reverted to how things were in the past. They would give me a mountain of work in their eyes. I would complete it in two hours. And then I would go back and be like, what else do I have to do? It just felt very easy to me what the tasks they were giving me to complete. So I felt like I could do that job. I could make money doing it. I really had no passion for it. The more I was in it, I was like, this just feels like work. And it wasn't something I enjoyed to do.

9:00I kept saying, you know, my whole life, seeing my father run his own businesses, I guess there was this thing in the back of my mind that maybe one day I would open my own business. I didn't know what it was. So I stopped and said, you know, I've got all this experience. I've been doing this thing my whole life, but I've always been working at my father's locations, thinking I'm helping my dad, not could this be something I actually want to do as a career. so it was the moment of talking to my father saying like you know I don't think I want to practice law he had one of his locations it was a sandwich shop literally across the street from my law school so he was a customer my first year he needed help he needed a manager so would you let me run the store he thought it was a little odd request but at first he's like if this is what you really want to do sure so my grades did suffer second year when I did that but the business picked up quite a bit under my, you know, leadership tutelage.

9:52I realized I was good at it, mainly because I'd been doing it my whole life, sort of that Malcolm Gladwell 10 ,000 hours. I realized I literally, from shaving carrots when I was five, making deliveries when I was seven, watching all the things my dad did. It's so crazy. We were literally just downstairs getting some coffees while the team here was prepping upstairs. I can't go into an establishment like this and not pay attention to POS, to how fast is the register moving. Think about the thing you know the most and think about how you look at it versus people that know nothing about it. I'll give you an example.

10:26Somewhere in my mid-20s, late 20s, I was like, wait a minute. Look at all these people at this restaurant, the way they're drinking wine. They're drinking it like water. They're not even thinking. I would take like an eight-minute thought process of smelling it, tasting it. It consumed me. Or when I watched the Jets and I watched casual people. Like you just, when you know something so much better than the rest. So for me, retail and restaurants and things of that nature, I don't walk in and order a coffee. I walk in and order a Gregory's Coffee, a Jolly Jacko pumpkin spice chai latte. I also though, I'm watching the staff trying to figure out why the POS is doing what it's doing.

11:03Thinking about how clean the store is, which is an incredible challenge in New York City. It was hard enough in New Jersey and the suburbs. Traffic, like watching how people were walking by the street I'm curious if they would like look at the storefront, notice like 30 of them looking at their phone, was like, oh right, like storefront real estate is kind of like outdoor media. Like 50 years ago, like the signage in your store converted better than it does now because people are looking at the phone. Just all these random things that like literally ran through my mind in two seconds downstairs.

11:31Yeah, I mean, it's honestly, as we've expanded, sometimes it can be a problem because if I haven't been to a store for a long time, sometimes I may have this anxiety as to what am I gonna see because I know I have these sensors that start firing. The minute I walk in, it's like, that's not correct. My father has one store every day. He's really just unhappy on his drive to work, which is 45 minutes, because basically he knows he's going to walk in and see something he doesn't like. And he's got one store, and he's there every day. So for you, having dozens... There's an appreciation effect, because my team knows that I will lift them up.

12:05There's things that they're working hard. Some of them are newer at this. Some of them are doing it for a while. But even that, you can get blinders if you go to the same spot every single day. So when I come in and I give feedback or point things out that maybe they were missing, it's all in the mindset of just, yeah, I'm not here trying to catch them do something wrong. That's based on delivery. This goes back to candor. I think about kind candor versus not kind candor. Everyone listening knows owner, manager, who's got a bunch of stores. We've all seen the cliche. We all are thinking what I'm about to say, which is that boss that walks in when she or he's going to look at all 10 stores and just starts yelling and leads by fear.

12:43Yeah. And I think... I don't think I've ever yelled in the 17 years. How about your dad? Was he a little more old school? No. That wasn't his disposition either. He worked as hard or harder than anybody there, and he has people who've been working with him for 40 years. Literally, the people that have stayed with him in a food and beverage establishment, which is probably the most rare... Of course. And I always took that, which was... Free people with respect. Let's bring some value to everybody who's listening and managing. Let's stay on this for a second. What do you think in the 17 years that you've been running this?

13:14Actually, let's context it for everybody. Gregory's Coffee, how many locations? Which states? 36, about to open number 37. Where? In Darien, Connecticut. Actually, we're having our final inspections right now, so I do have a little bit in the back of my mind. Hopefully, it's going okay up there. Oh, trust me, I'm thinking about nine other things while we're doing this. Go ahead. But we're in New York, New Jersey, Connecticut, and Washington, D.C. So 36 today, hopefully 37 by the end of the week. Any plans for any extra states as you? Yeah. Little Rhode Island, little Boston, a little Delaware.

13:44This Northeast Mid-Atlantic corridor certainly is right in my wheelhouse. My in-laws are up in Rhode Island, so they ask me all the time. Definitely love to get down to that Virginia market. So yeah, kind of bridging this Northeast 95 quarter. So in the 17 years from location one, which was what? 2006, 24th and Park, first one. OK. The ours? Yes. No. Yes. Is that what's so funny? Notice what I just said? That was so weird. Ours. That's amazing. Okay. From that store to the one you're about to open in Connecticut, what do you think from day one, because you, like me, had a lot of training as a kid, from day one was your biggest strength that you continue to be great at or you've doubled down or refined?

14:24And what do you think was your biggest weakness in hindsight that you've been able to close the gap on? And even above and beyond that, if you want to talk about that one or something else, What is the thing that you're still potentially struggling with as a manager of such a conglomerate? So I think my biggest strength from all along was just my passion, my dedication, my unwillingness to let things go awry. So I'm just... You willed it. Yes. I've willed certain things into existence by sheer efforts. Intestinal fortitude. Yeah. I would, you know, my team would probably tell you I'm, you know, the Larry Bird.

15:02I'm the first guy. I am in our stores with somebody who works for VaynerMedia up at our great location. Every morning, they open the doors. I'm there minutes before or after they open, so 6 in the morning. And then I'm here, you know, 6, 7, 8 o 'clock at night, whatever it is. I'm usually the one turning off the lights. And then weekends, too. If anybody needs me, I'm always available. My wife might have a few things to say about my unfettered availability. It's hard. My team feels it, and they appreciate it. So I think there's a lot of things that I've just been unwilling to let fail. And my team feels that.

15:40I think it kind of might tie into my biggest weakness, which is sometimes my inability to let others do their thing, give them the room. What is the balance of micromanaging or coming in and being the leader? That's the balance you've been struggling with at times, right? I mean, I think a lot of it is we were small for a long time. I mean, we had 18 locations and there was probably three total corporate employees, including myself. It's only recently where we've even started to expand in a corporate team and where I've started to have others who are capable of taking on responsibilities. But I think people need to hear this who judge like work ethic or judge what you're talking about now.

16:16I think everybody who's listening and hit me up on Twitter, Gary VEE, if you agree with this. If you own a business, it is like a dog. It's like a child. It's your baby. You know, obviously that resonates with me. I don't view you as like this crazy guy. What I view that is, I get it. This is like part of your family. When people don't have a business and aren't entrepreneurs, I'm incredibly empathetic that they don't understand in the same way I'll make the one that I do think people understand. For all the people right now who have a dog, who judge or laugh at their friends, who don't understand because they don't have a dog, what it feels like to be a dog owner and what it feels like and why you cry when the dog passes away or is sick.

16:57It's a family member. Believe it or not, that is what a business is to a true-bred entrepreneur. I mean, it's certainly how people refer to me as Greg from Gregory's. This business is an extension of me as a person. Well, you're the logo. Exactly. It's hard to get away from it. I'm pretty impressed with that. I'm actually thinking about rebranding VaynerMedia. I think Gary B needs to take over for the very, very, very, very lucky black hat. I look at the logo here, and I'm like, you know what? I think he figured it out. So I think you kind of hit it a little bit there, but that the allowing or the, you know, giving others some of the things that, again, I have another gift in a curse is I've done everything here from fix the espresso machines to plug the toilets to everything.

17:42Speak on that because I talk about this at VaynerMedia. The reason I'm always calm is I know if every, if David, our friend Rossiter, starts a coup and takes every employee with him, I have no fear because I know how to do every job. I think a lot of entrepreneurs make that mistake. For sure. Even my father would tell me when we started roasting our own coffee, he's like, don't forget, you need to know how to do that too. In the event something ever happened, because that's his old immigrant mentality too. You're the last line. That's right. You're the last line of defense. Whatever happens. I mean, there's been times where I had to drive the truck.

18:13The delivery, we couldn't deliver. It's like, well, am I going to open tomorrow? I remember a major snowstorm, probably like 2011, 12, where the city got shut down. My store on 44th and 6th, it's all hotels on that block. Nobody could leave. Everything was shut down. My store, we were baking everything out of our store at 24th and Park at the time in the basement. There were people that all the hotels couldn't get any food. So we baked the product at 24th and Park. I put on like snowsuit, carried it like to a subway, got there, carried it through more snow. And people were like grabbing food out of my hands out of the baskets because they literally had nothing to eat on that block.

18:49And I'm like, I'm walking in, carrying as much product as I could, and my team was surprised that I would do this, but I'm like, who else is gonna do this? Because I literally, it's hard for me to sit and watch something not happen if I have the ability to make it fixed. I told a story for a long time. My most famous Wine Library story is a woman in Bergen County getting a delivery to the wrong place of Behringer White Zinfandel, which is$3 a bottle, a$36 case of wine, misdelivered, she calls and complains. It's in December with bad weather. It's one of the busiest days in the store. I am the disproportionate leading salesperson in the store.

19:32Like every third customer that was gonna spend two,$3 ,000 on collectible wine came in and says, where's Gary, he's Gary here, where's Gary? And I knew that I had a moment where I did it for two reasons, one, this lady, I'm sorry, her son called and was really complaining because she was really upset because she needed her Behringer White Zinfandel for the holidays. She was elderly in her 90s. And I knew that it was an opportunity for me to show that customer over everything, no matter what kind of customer. And I took a case of Behringer from the warehouse downstairs, threw it in my car, drove to Bergen County, delivered it to her and came back, missed an hour and a half, lost tens of thousands of dollars in revenue potential during that time.

20:15but it became a story that became connective tissue for my company to speak about like exactly what you're saying. If you as a leader are able to fix, I think too many leaders would rather blame their team for it not working than jumping in and getting dirty and fixing it. Oh, yeah. I mean, there's a book that my priest had recommended me at one point and then kind of really struck a tone with me called Extreme Ownership. I don't know if you've heard of it. I can't read for shit, which is why they hit the grave. I mean, at the end of the day, the concept that it says is that if something is within your control, like within your four walls or your sphere of influence, and you can't – and if something doesn't go right and you can't honestly say, I did everything in my power to make this have worked well, then you should look at yourself and say, it's on me.

20:59It's not on them. 100%. So I've sort of taken that to heart where I don't like placing blame. I'm right in the trenches with everybody else. Especially when you're the owner-founder like you are. You hired those people. Right. Like when I look at my incredible team that I'm looking at right now, like these six people, like I hired them. And if I, you know, because even if it's indirectly, Sid who runs the team, if he's hired one of the individuals here, well, I hired him to hire them. I will never understand this obsession of blame when you have full control. What's the easy route, right? I could always just point the finger and say.

21:31What's a societal issue? I mean, I believe that so much of our unhappiness right now is predicated on that. You want to blame the mayor of New York. You want to blame the president. You want to blame a party. You want to blame social media. You want to, I had a friend who's blamed, spent the entire 30 minutes blaming social media and the mainstream media. And I'm like, what about you? Like, like what, what are you consuming? I mean, we experienced this mid to late kind of COVID where there was a, I was doing the thing where I was blaming COVID on issues we were experiencing. Well, oh, well, this store might be slow because of COVID or that's happening because of COVID.

22:05And then I felt like, well, what am I doing? I'm saying like, you know, there's people in the street. if they're not coming in, they're going somewhere else. They're going somewhere else. And it must be something we're doing or not doing. So it caused us to kind of look. We made adjustments, tweaked. What was the biggest tweak you made in that scenario? I mean, our food program, our customer service, just how we, even how we packed bags to like how we made it easy for people to access things. So we had to move things around, rearrange, even reconfigure our menu to, you know, there's points where there's less options available.

22:39So people were looking for a one-stop. People used to be comfortable bouncing to two, three different places. They'll get their coffee from here, sandwich from here, muffin from there. Got it. Now it's like I don't have the time, nor do I have the interest in going. So how can we update what we did to make it more appealing to what people today are looking for? Even like we were talking about delivery, right? We weren't very good at delivery because we didn't do very much of it. We weren't packing them very well. They would show up and product would spill just because it wasn't in our time. It wasn't in our core competency.

23:07We would maybe get one or two deliveries a day pre-COVID. Now it's like dozens a day per store. So we had to get better at it. You know, now those scores have gotten significantly better. Let's talk about collaborations, since we have one together with BeFriends and this Jolly Jacko pumpkin spice chai latte. Delicious, go get one. Yeah, I'm pretty, like, pumped with the feedback of the... You know, everyone thinks their baby is the best-looking, so I'm not going to judge on how delicious this is. I'm just reading Twitter, and you and the team have done a great job. clearly people like it. Is it still Twitter?

23:39I just call it Twitter forever. I'm old school. I still say tweets, but I'm like, what do you say? Am I doing an X? I'm X-ing something out? I don't know. I'm really lost on how to describe this. Yeah, I'm just very comfortable calling it Twitter, but I'll change if the world wants it. I'm consumer-centric. How do you think about collaborations? When was your first collaboration, if you can recall? Why do collaborations? How should people that are listening right now that may have a business that is in the kind of demo that is possible to do collaborations, even if they have one store or one product.