I Know A Guy: How Adam Guy Built A Business On Connection | Ep. 101 Artwork

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I Know A Guy: How Adam Guy Built A Business On Connection | Ep. 101

April 06, 2026 • Aliya Cheyanne • Season 6 • Episode 101

0:00 | 51:55

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In this engaging conversation, Adam Guy shares his transformative journey from a successful career in nonprofit marketing and fundraising to founding I Know A Guy NYC Tours. He discusses how the COVID-19 pandemic prompted him to reevaluate his career and take the leap into entrepreneurship. Adam emphasizes the importance of connection, authenticity, and storytelling in his work, as well as the joy he finds in creating meaningful experiences for his guests. He offers valuable insights on navigating career changes, the power of word-of-mouth marketing, and the magic of New York City.

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A 2 A.M. Wake-Up And A Leap

SPEAKER_07 0:35

And six days in, I just woke up about 2 a.m. in a cold sweat. And I knew something was wrong. And I had been there for six days. It was a great job and really good people. And I knew I could do a good job, but something wasn't right. And so I woke up and I was sweating for a while. I came out to the living room, and about six in the morning, my wife comes out. She's like, You've been up all night. And we chatted. We chatted for like an hour and a half. And at the end of this long chat about what I was feeling, she's like, Look, I know you many, many years now. I see you all the time. You are Tigger. And for the last two, like Tigger, like Winnie the Pooh Tigger. She said, You excite people. You're a firecracker. You have tons of energy. You bring good out in everybody else. For the last two years, I've seen you evolve into an Eeyore. And if this job isn't gonna help you get back to being Tigger, it's not the right job. You're just gonna continue this cycle. And I I mean, those words were the most important words I heard probably in in many, many years, because they were they were right on the nose. And it also gave me permission. Now we were in a we were in a fortunate position that financially we were secure enough that we could take this risk of quitting my job. Terrifying, by the way, terrifying. I'm a yeah, I come from a place of security. Like my parents have drilled in security, security, security, have the job. And then I called my boss at 8:30 in the morning and I had that conversation. And what I expected to be like a tongue lashing, well, you would be, you know, you'd be angry. He was the most supportive guy I've ever come across. He's like, you know what, Adam? I actually went through the same thing. I get it.

SPEAKER_00 2:08

Wow.

SPEAKER_07 2:08

And and I I I'm grateful to him for this day. And then and then you do what you do is you hang up the phone, you breathe for about an hour, and then you go, What did I do?

Aliya Cheyanne 2:28

Hi everyone, welcome back to Music Mastery. Thank you so much for joining today's episode. And I'm so excited today to be joined by Adam Guy. Hi, Adam.

SPEAKER_07 2:37

Hey there, Leah. How are you doing?

Aliya Cheyanne 2:39

I'm doing great. I'm so excited to have you on the show. We were chatting a little bit before we started recording, and it's really nice to see you again. It's been a while since we have, even virtually, so that's really nice. And for folks who are listening, Adam is a super cool person. Many years ago, many careers ago, we crossed paths at an affordable housing intermediary. We were working there at the same time. Adam was on the marketing team. I was on the policy and program team. And I have just watched and admired Adam's transition from working in that role and other roles to really founding and launching his own business that feels very much aligned with his personality. He has a big personality and very knowledgeable. And I'm super excited to get into all of the things today about I Know a Guy, NYC Tours. And with that, I want to pause though and kick it over to Adam. And Adam, if you could share more with us about who you are in the world today and how you'd like to be known.

COVID, Identity, And Finding Joy

SPEAKER_07 3:40

Yeah, well, I'm Adam Guy. That's why it's I Know a Guy, NYC Tours. Kind of that's the that's the hook. And yeah, I've I had a long 25-year career in fundraising and marketing for some great organizations like Boys and Girls Cubs of America. With you, we worked with enterprise community partners, some really meaningful, positive work. And then uh, and now I'm not doing that, of course. Now I'm doing something totally different. And that's really a result of COVID. I'm that story. I'm the guy who was in his tiny New York apartment, you know, all day long on Zoom. And I, uh, as you said, I'm I'm kind of a bit of a firecracker. Even in an office, I can't be contained. And so that really changed who I was and and really helped me rethink about what are my priorities. And while I worked throughout COVID, I at some point I knew it was time to change. And it was a scary, scary, terrifying leap. But I did it and I started this thing called I Know a Guy Tours without ever knowing how to be a tour guide. What is it about, how to start a business. But I I took the big leap. I had a sense that this might be the right thing, but you never know until you you jump in the pool. Um, and now I'm I'm three and a half years in and I am full-time. I'm my own company. I had the most successful year I've ever had in a business last year, and I'm uh I have found my joy. I'm my own boss. I I deliver joy out to my guests. I show people this amazing city and I make them laugh, and we have meaningful moments, and I'm in a good place. It's a really, really healthy, spirited place to be.

The Six-Day Job And Tigger vs Eeyore

Aliya Cheyanne 5:07

Yeah, and I feel that a lot, even through witnessing the stories that you share on LinkedIn about your guests and the stories that you tell. It I'm always so interested and excited when I see a post of yours pop up in my feed and to like read about your guests, where they're from, like what you related on. You shared a really fun post the other day, actually, about someone who was in a small airport somewhere else in the world, and they had one of your marketing items, and another person recognized it and said, I know a guy. And I was just thinking to myself, that is so cool. And it really does, as an outsider looking in, feel like you're walking in alignment with what you're meant to be doing in this season of your life. And that's really exciting to witness. So it's exciting to hear you talk about it so passionately and to talk about how you've had one of your most successful years yet, wishing you many, many more years of success. But I want to get into all the things and I want to jump in a little bit more about what you shared about how COVID really sparked this transition for you. I think for many people, that was such a time of reckoning. Many of us were trapped at home. We didn't have a choice. Um it put a lot into perspective. A lot of people started asking questions about like, what am I doing? What is my purpose? How can I feel more fulfilled? What is more exciting to me right now? Even thinking about your work, just the need to get back outside, to do something outdoors again. And I, you know, it's just really powerful to think about how that time impacted so many people. Not as many people can say that they've successfully started and run a business for the last three and a half years, but that time really planted a seed for a lot of people to really want to try to do something new. So I would love to talk to you a little bit more about what are some of the smaller markers that were leading up to this big aha that made you want to take the leap, like the quiet pings that were kind of nudging you along the way.

SPEAKER_07 7:15

Yeah, I think, you know, recognizing where I am in life, I'm a 100% extrovert. Like when you look at that spectrum of where I sit on the introvert, extrovert, and you know this because when we were in our office, we have at the office I worked with, you we were very cerebral, very thinky, very like in the book kind of people. And I'm this guy who's like popping balloons and like didn't fit in into the culture, but I will say that I know that I needed to be with people. And so that need as an extrovert is really important. And while you're here in your apartment, Zoom as a medium for two years didn't really cut it. I needed, I needed to have that water cooler chat. I needed to be like, so what was your did you see that Broadway show or uh what's going on with your mom or whatever that thing is? That is the that is the the connection that I'm looking for. And I think at the center of what I was doing then, and even now, and I think it even sits harder, is that idea of connection and how important that is to me and and what I want to foster with my guests, right? And I get guests of all personality types, all over the spectrum of older, younger kids, and I need to find a way to connect. And I tell you what, the tours are important, the information is important, the stories are important, but the connection is the most important thing. And and that feeds me, and I know at the end of the day it feeds my guests.

Aliya Cheyanne 8:34

Yeah, I love that response actually, because we hear that a lot. Like, I've I've been on the other side of it as a more introverted person, where a lot of folks are like, uh, despite the state of things when COVID was happening, like it wasn't the worst thing in the world for the introverts to be at home. But I've also thought about people who have more extroverted personalities. Like, that's such a daunting time to just be in isolation, like stuck in a way where you can't have the connections you're used to having with other folks. So it's really powerful to hear you talk about that as well.

SPEAKER_07 9:10

You asked a lot of there were a lot of moments of that, like missing that. And I think it was more, it wasn't many things, it was just a lot of beats, a lot of drum beats of, and that beat got more and more and more as COVID, even as we exited COVID, I learned we weren't going back to the office. In fact, I got a new job for six whole days, and at that point I was like, okay, it's done.

unknown 9:29

Yeah.

SPEAKER_07 9:30

And there's a good story behind that. We'll get to later.

Aliya Cheyanne 9:32

Yeah, yeah. I mean, I would love for you to jump in and out.

From Nonprofit Pro To New Guide

SPEAKER_07 9:35

Oh, yeah, yeah. Well, so it's funny, there was a moment. There was a moment. So I had I'd started a brand new job um in COVID. Uh-huh. And I was in there there six days. It was a really good job. It was the Goodwill industry. So another continuing on my my enterprise or my um nonprofit track, and I'm really passionate about doing something meaningful for the world. And six days in, I just woke up about 2 a.m. in a cold sweat. And I knew something was wrong. And I had been there for six days. It was a great job and really good people, and I knew I could do a good job, but something wasn't right. And so I woke up and I was sweating for a while. I came out to the living room, and about six in the morning, my wife comes out. She's like, You've been up all night, and we chatted. We chatted for like an hour and a half. And at the end of this long chat about what I was feeling, she's like, Look, I know you many, many years now. I see you all the time. You are Tigger. And for the last two years, like Tigger, like winning the poo. Tigger. Yes. She said, You excite people, you're a firecracker, you have tons of energy, you bring good out in everybody else. For the last two years, I've seen you evolve into an Eeyore. And if this job isn't gonna help you get back to being Tigger, it's not the right job. You're just gonna continue this cycle. And I I mean, those words were the most important words I heard probably in in many, many years, because they were they were right on the nose. And it also gave me permission. Now we're in a we were in a fortunate position that financially we were secure enough that we could take this risk of quitting my job. Terrifying, by the way, terrifying. I'm a yeah, I come from a place of security. Like my parents have drilled in security, security, security, have the job. And then I called my boss at 8:30 in the morning and I had that conversation. And what I expected to be like a tongue lashing, well, you would be, you know, he'd be angry. He was the most supportive guy I've ever come across. He's like, you know what, Adam? I actually went through the same thing. I get it.

SPEAKER_00 11:25

Wow.

SPEAKER_07 11:26

And and I I I'm grateful to him for this day. And then, and then you do what you do is you hang up the phone, you breathe for about an hour, and then you go, What did I do? Yeah. Oh my God, I don't have a job. There's no income. What do I do? I like I have no plan. I have no idea. And my wife and I had chatted about the idea of the tour guiding thing. It had been something that was sort of a kernel in my brain. I had volunteered for four or five years with a great organization called Big Apple Greeters, which is the volunteer group where you take first timers around in the city, a lot of them international, just to make people feel comfortable how to use a subway. And I did it like 20 times a year for five years, and I loved it. But what I loved about it was the connection. So the the leap to getting to Tour Guide was simple. Now, how do I monetize it? How do I learn the stories? How do I market myself? How do I create a company? I didn't know any of that. And I I freaked out for about eight weeks.

SPEAKER_01 12:22

Yeah.

SPEAKER_07 12:22

And then so we'll I'll pause right there.

Aliya Cheyanne 12:24

But yeah.

SPEAKER_07 12:25

Yeah.

Aliya Cheyanne 12:26

Yeah, that's a really powerful story. Even just going back to you having the many moments and then waking up and having that realization six days in is really powerful. And like answering that call, but also having the support system that you have, because not many people could go to their spouse with these feelings and and be received well. And to have someone say, I see you, I know you, and what a beautiful analogy of Tigger and becoming an Eeyore. Like that's they're gonna that's gonna resonate with somebody right now, like listening to this. So that was really powerful.

SPEAKER_07 13:03

I uh I know I couldn't do this without her, not only without her, just structural support system-wise, but but just like go for it. She said, like in two years, if you haven't figured it out by now, you can go back. And she was right, I could go back. Funny enough, now I'm almost three and a half years in. I think I've forgotten all the skills. So yeah. So so I don't know. Now I don't know that I want to go back.

Aliya Cheyanne 13:24

But uh that's the thing about venturing out on your own and doing it well too. It's like it's it's hard to go back to what you were doing before, especially when you found something that you love.

SPEAKER_07 13:33

Yeah, very much so. Very much so.

Building A Business On Connection

Aliya Cheyanne 13:35

Yeah, yeah, that's really powerful. And I would love to talk about some of the more nitty-gritty aspects of that. So, like you said, you had the conversations, got off the call, took an hour to yourself and was like, what did I just do? Didn't know any of the things yet, lots of uncertainty for several weeks, maybe for months, you never know. I would love to talk to you a little bit more about that transitional period because, like you said, it was a leap of faith. There was a lot of fear involved, there was a lot you had to learn. So, how did you navigate that period of time? How did you set yourself up for success? What were your tools and resources and things that you made sure you built into your routine to realize your vision?

SPEAKER_07 14:20

Yeah, it's it's a great question. I'll say for about two or two weeks, it was a lot of for the first two weeks was like, okay, start writing lists. Go take tours. I took probably 25 tours. Like, what is a tour? Like now look at it from a tour guide, but what does that mean? What is it, where should I go? What do I like? What do I not like? Uh go look at a bunch of other websites. What I need to build a website. How do I do that? What's the name of my company? Now that had a little bit of a jerk a germ already started because I had the name as a marketing company as an idea a long time ago. But that was a nice little bit of a leap to go to I Know a Guy, NYC Tours. So I kind of had that. But what I also said is you know what I do like? I like the greeter experience, that small, intimate, small group. I like the personal connection. How do I make sure that whatever I deliver, and there are all sorts of tours, food tours and group tours and international tours. How do I do the thing that I want to do in the way that I think guests want to have it?

SPEAKER_04 15:12

Yeah.

SPEAKER_07 15:12

And I just felt like there was this place in the market for that kind of experience. And there's nothing wrong with the person with the flag and the microphone and 30 people were that's fine, perfectly great. Wasn't me, because again, the thing that I wanted most out of all of it, connection. And the second you can't remember somebody's name is the second you lose the connection. So there was that germ there. So I did websites, I took tours, I started making notes, and then I came across, and I had vaguely been familiar with something called Trip School. And Trip School is like a program, and it's based in New York, all they do it all over, that it literally teaches you how to be a tour guide, and they have lots of channels. So there's there's uh a boot camp, which is like one intensive week on how to become a tour guide, and then there's the entrepreneurship side, like how do you sound a business? Then there's there's a couple of other channels, marketing for the and just as the universe would roll out in front of me, six weeks from that point, there was a boot camp in New York. And I signed up. Now, the interesting thing is most people who sign up for that are very similar to me. They're going through some transition, not a lot of like 18-year-olds in that. There's like 30 or 40 year olds who have a lot of teachers, things like that. And I went and I did this one week intensive, and it was amazing. And what was great about it, funny enough, is it literally puts you out in the field. The training is okay, you're at Central Park, Adam, you're in charge of Central Park, go give us a tour. And it gives you that real world in the city experience, and everyone got little assignments. And you do that for two days, and then they teach you about some of the technology and they talk to you about storytelling. And at the end of the day, while I learned a lot, and I didn't learn how to do everything because I had had been doing some work on that a little bit, but I went in there and at the end of it, what I felt was okay, I'm not crazy. I'm in the right place. Like I know I can be on this path. I'm okay. Like I'm gonna be okay. Now, did I know anything yet? No. Did I have any business yet? No. But I I knew that I I knew that I had landed on soft ground.

SPEAKER_04 17:05

Yeah.

Learning The Craft At Trip School

SPEAKER_07 17:06

And then after that, it was really, now, let me put that into practice. And I started building tours, and I got a couple of tours. When you I put a big announcement down there on LinkedIn, right? And Facebook. And like any small business, you start with your family and friends. And I'll tell you the most validating thing I got when I put that first big announcement, here's what I'm doing with my life, guys. Like thousands of people, like, why didn't you start this years ago? I can see you in this doing that right now. Everyone I know, I'm gonna send to you, oh my God, I know a guy. Like it was as if the universe clicked in a minute, and all of my friends said, What have you been waiting for? Yeah. And so things got rolling. Now I did work for another company for about two months because I didn't have any business. I was like, let me get some experience under my belt. And I learned some things that I liked and things I didn't like. And I think that's good. Sometimes it's okay to learn the things you don't like. And then after about two months, I said, okay, if I do, if I work for this person, I can't invest the time I need for myself. And then I said, Okay, like the training wheels are off, go. And the first year I got like 50 tours, which is insane. I don't do any paid advertising. You should know that. It is 100% social media or word of mouth. Word of mouth, of course, at the beginning, and that that phrase, I know a guy, really does come up. It's oh my gosh, you're going to New York. I know a guy, it happens. And then, and then I really up my social media game, which you're you get to see. I'm thank you for liking all those posts. And what I realized about six months in is I need to figure out a way to express not the sites of the city, although I do a lot of that too, but there's tons of people who do that. How do I show somebody who wants to take a tour with me what being on a tour is like?

SPEAKER_04 18:42

Yeah.

SPEAKER_07 18:43

And so I listen to my guests, I chat with my guests, we get to know each other. Now I'm not out there sharing their whole personal world. I want to help people understand that we have moments. And sometimes there are moments together, sometimes there are moments with a family, sometimes there's moments of them ingesting the city that you go, oh, yeah, that feels great. And sometimes it's silly, but I'm always trying to find that connection. So that's what I share. And I think what I have seen the world respond to me is that.

SPEAKER_01 19:10

Yeah.

SPEAKER_07 19:10

Especially moms. I take a lot of kids around. Moms want to see that there's going to be someone fun and safe that can take on any kid.

SPEAKER_04 19:18

Yeah.

SPEAKER_07 19:18

And to that point, I'm always trying to find out where and with everyone, kid or adult, I'm going to meet them where they are. We are going to find that connection. Whether you are the most introverted person in the world or you an extrovert like me, we are going to find that thing somehow. And I'm going to get it.

Aliya Cheyanne 19:34

Yeah. I love that. That's so beautiful and so powerful. And I love what you said exactly around when you made the decision, when you jumped in the deep end, made the decision, like the universe responded to you. But it rose up and conspired to support your dreams. And I think that's so powerful too. I love you honing in on the fact that there's no paid marketing. It's all either social media or word of mouth. And that speaks to the brilliance of creating, I know a guy and locking that in early and really running with that because it's an easy phrase to remember. And I think that's so brilliant too.

SPEAKER_07 20:11

Thank you. I'll say this to any any marketing person who's like a real pro will tell you that is the hardest and most the worst you can't run a business on word of mouth. And I would agree, it's taken a lot of heavy lifting, but now I have a lot of momentum. Don't get me wrong, people do find me like Google searching sometimes. That's great. Some people find me because of uh I just some other I've been on a few podcasts and there's been an article or two, and that's lovely. But at the end of the day, most people are they hear that idea and then they do come to my presence and that presence being a website or social media to understand what it is. And and I say that because if you go to my website, which is Inowaguide.nyc, most reasonable tour guides would have here are the five tours I do. Pick one. I don't do that. I'm like, here are all the neighborhoods we can explore. Let's chat, let's figure out the right ones for you and your family. Yeah. Let's figure out the right ones for your group so that we can really make it sure it's the best experience possible. So that's a little unorthodox, but again, there's there are people out there wanting that. And I found them.

Aliya Cheyanne 21:10

So yeah, and I think that speaks volumes to you really being intentional and serious about prioritizing connection. Because if you're keeping that at the center of your business, if that's a core value for your business and you always stay like focused on that, everything else falls into place. You're prioritizing connection through your website, through the way that even people can even get in contact with you to figure things out. You're very accessible to guests, very accessible for people to learn more. So I think that really speaks volumes to prioritizing connection. I think that's powerful. And you talked about marketing, how for some folks it's it's bad advice to rely on word of mouth. It's working very well for you because it's it's very aligned, but it's very clear as well that you have not completely left your marketing hat behind. You're still applying tools and tricks to your work now. And I think that's really cool too.

Social Media, Word Of Mouth Momentum

SPEAKER_07 22:06

Well, thank you. So and to reference back your story, so you you started this by saying you read the story online. I'll give you that story. So there was a woman who had been on a tour with me about five months ago, and we connected and we had her family was here. And one thing you should know about all of my guests is when they arrive at their hotel, they get a welcome kit from me, which is a nice personal connection. And it has some nice trinkets in it, a card and some gummy bears, some things like that. But one of the things I also include is this it's a hand sanitizer right there. See, with my little face on it, cute little thing, right? Right? And and it's just a nice thing and very appropriate for New York because if you're gonna ride the subway having hand sanitizer, and people love this stuff, it's great. But I know it's a nice welcome thing, and I like doing it for people, and it's a good, it's a good leave behind, right? Well, this woman who had been on a tour six months ago texted me out of the blue the other day. She's like, Adam, I just left Antarctica and I was in the airport in Argentina flying home, and I reached into my purse and took your hand sanitizer out, and I was using it, and I set it down for a minute, and a woman saw it from across the room, and she came over to me and she said, Is that I know a guy? She's like, Yeah, I know a guy. She's like, Oh my god, I follow him. When I go to New York, I'm booking a tour. Like just this little thing.

SPEAKER_04 23:16

Yeah.

SPEAKER_07 23:16

And it was in Argentina from Antarctica, like, even I'm like, you know, and so this is marketing, but this is also a reminder of connection. So she didn't just she didn't have to text me from Argentina, but she was like, We we now have a connection enough that she's willing to do that. To me, I'm like, my heart, my heart's full. Yeah. I mean, this is amazing. The heart part is it got me.

Aliya Cheyanne 23:42

So yeah. And do you find that many of your guests or some of your guests occasionally reach out in that way, like months after you're wow, that's really beautiful. Yeah.

SPEAKER_07 23:52

I mean, I'm very friendly. I usually friend everyone on Facebook or Instagram or something just to follow their lives. You know, we I'm not saying that we're we're embedded in each other's lives, but I think at the end of four, eight, sometimes eight hours, sometimes two days, you make a meaningful connection with these people. And I think um, and it's authentic, and I think that's really important to know. I go out there every day as me. Like there is no, you know, this is tour guide Adam, and then this is not. You get what you get, and that is always me. And and the good thing about being with my guests is for me as an extrovert, guests bring out the best in me. So sometimes I walk to them and I'm I don't have the energy, or maybe I did have a rough day. Or man, being with guests brings the best Adam out, and they all see that, and that's very fulfilling. So my point is like there is no, you know, there are tour guys that are great show people because lots of them are actors, because it's a good side gig when you're an actor.

SPEAKER_04 24:45

Yeah.

SPEAKER_07 24:45

And they are great storytellers in that. And I I do okay. Um I can I can hang in there with the best of them, but but I but I also know that I'm coming to the table as me every time.

Aliya Cheyanne 25:38

Yes, yeah, that's really beautiful. Speaking of acting, so one of the things that I have always remembered about you is your love of Broadway. And you mentioned even at the top of the episode, like during the lockdown, like missing the connection, like being able to ask someone, like, what show did you see?

SPEAKER_04 25:59

Yeah.

Aliya Cheyanne 25:59

And I wanted to ask you if there are any takeaways or things you've learned from Broadway and theater that really has supported you, that you've been able to apply in your business, especially when it comes to storytelling.

Designing Personal Tours, Not Templates

SPEAKER_07 26:13

Yeah. I mean, a couple things that really jump out at me is the shows I always like the best, or or I should say I'm always in the best frame of mind to see a show when I know I'm present. And I say that because when I'm with my guest or when I'm I'm I'm noticing my guests, I'm always aware of my ability to be present with them and hopefully their ability to be present with me, the each other, and the city. Right. And some people are drifting off, and yeah, there's the occasional teenager who might love their phone too much, but being present is important. That's how you get into a show. That's how you get in the mindset, right? I don't sing and I don't dance. So there's none of that. I just want to make sure you know. Um, I think there's also some things, um, little things that you wouldn't think about, but I'm always punctual. I don't think I've ever been late to a tour. It matters a lot, right? I'm always thinking of what happens at the beginning, what happens at the middle, what happens at the end, and all the parts in between. You can't just start a show and get to a place and then go figure it out. I gotta, I gotta be thinking two scenes ahead. Yeah. And that's about building the show. And then it's about delivering the show too. And I want to make sure you're I the show is an improper word for the tour because I don't think about it as a show. I don't do the same thing every time. But I I want to make sure that full experience, all those notes, if you will, that you hit it in a show, the big notes, the meaningful notes, the silly notes, they have to be there. Your experience that you give a guest has to, it can't just be this. It has to be so that they are with you and you're taking the journey.

SPEAKER_04 27:41

Yeah.

SPEAKER_07 27:41

And that journey is the city, which is man, you step onto that Brooklyn Bridge. Yeah. You want it, you want them to feel that awe. You, you go by the 9-11 memorial, you want them to tighten that chest. Like, how do you, how do you bring that to them? You know, so there, there's there's I'm thinking about that.

Aliya Cheyanne 27:59

Yeah, yeah. And I think that's really powerful too. And it speaks volumes to the fact that you really are intentional and get to know your guests and really curate tours that are applicable to them, like their interests, like what they want to see, what they want to learn about, and really creating space for that connection. So that's really powerful.

SPEAKER_07 28:19

I'll say one other thing to that point. There are also things I don't do. And I think what's important about that is understanding your own boundaries, but and not comfort zone, because I want to continue to learn and grow. But like, I recognize that there are things that you can do in the city that having a tour guide like me doesn't help.

SPEAKER_04 28:34

Yeah.

SPEAKER_07 28:34

You don't need me for the Empire State Building. You just don't. It's enough there. There are neighborhoods that I have yet to learn, and the few that I'm a little reluctant to do. Like, I think Harlem is one of the most meaningful neighborhoods, but I also recognize that as a middle-aged white guy, it is a two-hour journey through the black experience in New York. And am I giving the authentic experience that it deserves? I don't know that I do. And I can do it respectfully and can do it with all the right stories and on the right frame, but I think there are people well more suited to do that. So one day I might take that leap, but in the moment, I feel like the a couple of the African-American guides I know who I have taken their tours, they do a great job. Learn from them. They are gonna give you that lived experience that I can't do. And not that I don't talk about Latin American issues or African-American issues or issues with immigration, that's all over the city.

SPEAKER_00 29:24

Yeah.

SPEAKER_07 29:24

Yeah, but there are certain pockets where I think, you know what, this is more appropriate for someone else. Or let's go another direction. You love comic books, Aliah? I've never read a comic book. You don't want to take a tour with me about comic books. But you know what? There's gonna be someone who does. Yeah. And let's help you find that person. I think that's important.

SPEAKER_01 29:42

Yeah.

SPEAKER_07 29:42

It's about getting them to find the right experience. And I think that's good. I'll give one last one though, but I I love Broadway. You said it, I do it, I see tons of shows. I give a lovely tour of Times Square as part of my journey. But if you really want to go deep on Broadway, there's this guy named Tim Dolan who runs Broadway up close. I'm plugging him. He does seven tours about Broadway. I take them, they're great.

Aliya Cheyanne 30:03

Yeah.

SPEAKER_07 30:04

Go to his tour. I and I've people like, you know what my tour? I'm like, I want you to get the right thing.

Aliya Cheyanne 30:09

Yes.

SPEAKER_07 30:10

That's the most important thing. And you know what? People remember that just as much.

Authenticity, Energy, And Guest Care

Aliya Cheyanne 30:14

Yeah, I think that that kind of goes into what I wanted to ask you next in terms of your business growing and scaling and what are some decisions that you're making to maintain the integrity of it, prioritize connection, maintain the integrity of it. And I think speaking to the fact that there are other tour guides who hold certain lived experience or expertise that you are willing to refer guests to, because it would be more appropriate for them to go to someone who knows more about Harlem, who has a lived experience, who is black, and who can relate to that experience because you have the self-awareness to know that that might not be the best space, particularly in times like these. Or even thinking about as much as you love Broadway and tours, there's someone else who has incredible tours and maybe go see them. So I think that's really, really important. And keeping those things in mind help to maintain the integrity of your business and your authenticity in building and forming connections with people, showing them that they can trust your word. You have good advice, you have good tips for other opportunities as well. So I think that speaks to building those connections as well.

SPEAKER_07 31:26

And that's not to say I'm not going to continue to learn. There are a few neighborhoods that are on my list to grow, get better, more stories. And I will do that. I'm three and a half years in. New York is 400 years old, and you know, eight and a half million people. I know about 5% of the 100%, you know, and that's really good. So if I can get to 10% by the time I'm done, I'm smarter than 99% of the people here. So um, and again, as much as it is about the knowledge, it's also about the experience as a whole.

SPEAKER_04 31:56

Yeah.

SPEAKER_07 31:56

When do you when do you stop and tell the story? When do you stop talking? When do you just make it about breathing? When do you make it about the jokes? When do you make it about let's just take a bunch of pictures? This is really, this feels right. Let's stop and capture the moment. Like that's as much of what I'm thinking about as I am getting to the next spot.

Aliya Cheyanne 32:17

Yeah. And I think that's really powerful. It makes me think, obviously, we all have intuition and we kind of know, but are there specific things you see sometimes on your tours? Like with guests where you're kind of like, okay, like maybe this is a minute to pause here. Like maybe, like, what are some of the behaviors you kind of pick up on that let you know how to pivot or adjust?

SPEAKER_07 32:37

Yeah. So right off the bat, I think the first thing is how quickly can you make your connection? And that's that's really that doesn't mean I don't mean like we're gonna be best friends right away, but I try very quickly to break down that Adam is a stranger barrier. And the good thing is there are a few bullets before we ever meet that that happens.

unknown 32:52

Yeah.

SPEAKER_07 32:53

Like whoever's getting the tour for me, we always have a conversation. We always have a phone call where we actually plan their whole trip, not just the tour with me. Yeah, and I help them, that's a good added value. So hopefully they know me. And then I say, funny enough, I say, stalk me, check me out online, make sure you know. And then we meet, they get the package, that's another little barrier, and then we spend time. And part of the journey is I meet them at their hotel and we subway together. So I teach them the subway, that builds trust. We take the ride on the subway, which always is allowed for some fun and and chatty things and cute moments, you know. Um, and then we start moving. And then I I am watching, I call it reading the room. Yes. How are people walking? How are they observing the world? Listen, this is the most important thing on any of my tours. Are they hungry and do they have to go to the bathroom? Those two things are strangely, if those two things are not addressed all the time, the fun stops, right? So checking in with them on that stuff. I think how fast are we going? You know, New Yorkers and you're a New Yorker, we walk fast. Or, like I say, we we actually don't walk fast. I want to make sure you know, we walk with purpose. Okay. We know where we're going, we are getting places. So we think about that. It's not so much about accomplishing 100% of the things in the plan. Although I have a plan and I know how long it takes.

SPEAKER_03 34:10

Yeah.

Broadway Lessons For Storytelling

SPEAKER_07 34:11

But how do we how do we read that room, right? Or, you know, we're going along the way and I listen to somebody says something about, oh my God, there's I love graffiti. Oh, you don't think I'm gonna pivot and find that graffiti? I sure am, if I can. Or, oh, I can sense this person needs a sugar break. Let's go get a chocolate shop. Or this person, you know, I it happens, of course, at like the 9-11 memorial a lot. Some of those meetings really, everyone, somebody who knows somebody, somebody who was there. What's what I think is most important to me is when so before we hit the memorial, we always step aside from the memorial and I talk, I typically talk about the story, like what happened on the day. And I always make the parents or the adults when there's kids there, where were you? Tell me about it. And I sometimes it's the first time the kid has heard what their parents experienced. Because that sometimes just isn't what and so I try and I want the kids to hear from their parents, I want them to understand. And then once we do the memorial, I ask the kids all the questions. What do you think? What do you feel? My hope is that when it goes back, they're having more conversations. And inevitably, there's a few where a mom or a dad knows a person and they they tell me, I'm like, let's go find their name.

SPEAKER_03 35:24

Yeah.

SPEAKER_07 35:25

And so as a family, as a group, we go find their name and we just sit there for a minute and we just reflect, and it creates meaning. And there are other places in the city. I don't want to minimize that, but that one, of course, is a moment of trauma and healing. And uh, and so yeah, those are the kinds of things I'm watching for.

Aliya Cheyanne 35:42

Yeah, and those are all really important. The basics hungry, bathroom, sugar break, yes, but also really listening to the interests that your guests have, things that you might not have known before, but it comes up in conversation, being open to pivoting and adjusting to show your guests more of that, what they're interested in, and really taking a moment to have that connection at many places, but also at the memorial, because it's so interesting to me. Because I imagine you get kids like of all ages, of course, that attend these tours, but some of them probably aren't even like born yet and don't even know that history and like really learning a little bit about it and hearing their parents' accounts of that, I'm sure, like creates a bonding moment for them too, just as a family. So it's really powerful that you can usher them into that space.

SPEAKER_07 36:33

And there's spots all over the city like that, like Roseau Island. That's a really mysterious place that nobody knows about. I love it. I used to live there. How do we make sure that kids get excited about the smallpox hospital? First of all, we got to talk about what smallpox is. Yes. What in the world is that? And so I'm a little goofy around there, despite its seriousness. And I'm like, okay, did everyone eat breakfast today? Because you you might get a little sick. I'm gonna show you a picture of smallpox. Yeah. Now I have a picture of somebody's hand. It's a very safe picture. Yeah. But like, then we have that ooh moment as kind of a funny thing to break down that. So there's little moments like that.

Aliya Cheyanne 37:06

Yeah.

SPEAKER_07 37:07

But those are those are pretty cool too. And I'm trying to where how many moments can we see stick?

Aliya Cheyanne 37:11

Yeah, yeah. I love that. And I don't want you to give all your special tour secrets away. But like, thank you for sharing those. And even as a like native New Yorker, I think I've been to Rose Allen like once.

SPEAKER_07 38:05

So great.

Aliya Cheyanne 38:07

And it was very cool. I really enjoyed it. I was like, oh, I need to come out here more often, taking the little lift thing out there. And yeah.

SPEAKER_07 38:14

For some of your work from some of your work from home days, yeah. My secret spot to work from home, go to Cornell Tex Cafeteria. They got Wi-Fi, they got restrooms, a cafeteria. Yeah. Just four or five hours there, you're good to go. That's you and me. Nobody, nobody, just between you and me.

Knowing Limits And Referring Out

Aliya Cheyanne 38:29

Between you, me, and us, and everybody listening. But yes, I love that. That's so good. I need to make another trip out there. That's really good. Yeah. So we're we're getting near to our end, but you've shared so much incredible information about how you got started, answering the call, listening to your body, how you felt, really connecting with your support system, your wife, anyone else around you. And this show is all about creativity, alignment, purpose, and all of those things. And something I've spoken about on the show before is really listening to yourself when you hear that call, that something needs to change, something needs to shift. So for anyone who might be listening right now who's considering making a change, who's considering doing something different, what advice would you kind of tell them about timing and taking the leap?

SPEAKER_07 39:24

Yeah, I think um it is scary. You should know that. And you know, we see we keep saying take the leap. There's an expression beyond that that says leap and the net shall appear. And I got that a lot. And it's a really, it's a really profound statement because sure enough, when you take the leap, it does appear. Does it always appear? Of course not. Or maybe doesn't appear the first time. But I think you gotta do it smart. You gotta plan. You can't just expect things to happen. It is about your proactive effort. It is, it is walking three steps and taking two steps back. It is, oh gosh, I have to pivot to the left. I I pivot it to the left, and I really needed to stay straight. It's oh, I need to be confident and stay my course. It's not going well, but I'm not giving it enough time. All of that trepidation, I think it's not easy. And there is no right answer, and there's no exact course, and you're gonna make a lot of mistakes. And the sixth time gets easier, and the seventh time gets easier, and the tenth time gets easier, and then you have another 10 to go. I'd say just give it a shot and try and get over that fear. You're gonna feel like an imposter, no matter what you do. If you got 25 years of doing it, you gotta build up that confidence. Sometimes you gotta sort of fake it till you make it, and it'll come. But I'll also say that in the end, and and and it took a lot of work to get to where I am today, and know that that first year was a hard year. Like I'm walking with my shoulders back now. I I don't feel that same kind of stress that I did working for somebody else. My stress doesn't feel like the weight of the world, my stress feels like busy, and that's a different kind of stress because at least I know where the busy's going, and I'm also in control of that busy.

SPEAKER_04 41:03

Yes.

SPEAKER_07 41:05

I genuinely feel joy when I do the things I do, and that doesn't mean I don't work a lot. If I turn the screen around, you would see an entire desk set full of packages and books. And I mean, sometimes I'm up at five in the morning and sometimes I'm working till midnight, right? I have global clients. But when it's working for yourself, it feels different. Yes, it's it just does that that 80-hour week week.

SPEAKER_00 41:30

Yeah.

SPEAKER_07 41:31

Because tomorrow I can put it down if I want to. Now, as an extrovert and somebody who doesn't sit still very well, I like to stay busy. It's important to me to stay busy. So I write a lot of social media and I write a lot of blogs and I I'm doing a lot of research and doing a lot of notes, and I like to be busy. I mean, I you know, I can go 10, 12, 14 days in a row giving tours every day. I'm good.

SPEAKER_00 41:54

Yeah.

SPEAKER_07 41:56

Physically, I need to I need to slow down a little bit too. I I did almost you know 3400 miles last year walking alone. It's great. Um, but to to to sort of people listening is is you can you can do it. You can do it. You have to plan, you have to try. It's an inertia thing sometimes. It's you need to keep moving forward or backwards or forward, but the second you stop, you stop. Yeah, keep moving forward. I'm I'm really proud of myself at this point. Like that sounds like a weird thing to say. It's not, right? I I'm I'm earning a living in New York City. That's crazy in a tough industry, a competitive industry. I did it, it's wrong to say by myself, because my wife, who's the guy behind the guy, right? Absolutely supportive. My friend network, incredibly supportive. Now my tour guests are telling the world about me. How do I not just feel so prideful of that? It's it's amazing. But I I just feel so proud that I I found my thing for now. People say you found your dream. I don't know if this is my dream. This just is my purpose now. Listen, I did nonprofit work for 25 years. I did really amazing stuff. I feel great about that. Yeah, but that was my purpose then. Today is my purpose now. And I just, you know, yeah. Anyway, uh, I just I I it feels great. It feels great.

Reading The Room And Pivots

Aliya Cheyanne 43:18

Yeah. Um, I think it's really incredible that you feel proud of yourself. You should. You've accomplished really cool things. I know you feel super grateful as well, just for your community around you who have supported you, lifted you up, your guests and your clients who continue to tell the story of their experience. And um, I think that's really profound. And I love your advice about how there's never a perfect timing. You have to take the leap, the net will appear. And just really listening and encouraging people to tap into themselves. Like your purpose can evolve. I've talked about that on the show too. Even what you said about your purpose then for 25 years was doing incredible work at nonprofits and marketing and fundraising. Your purpose now is I know a guy, NYC tours. This is your purpose now. It might change in the future, and that's okay. It's okay to be present and do what you love and enjoy now and be okay with pivoting in the future if you need to.

SPEAKER_07 44:19

Yeah. Yeah. For me, now it's about connection and putting putting a little joy into the world. I'm in the joy business. I'm in the making people laugh, making people smile, creating meaning. And when you do that for others, I think no matter what you do, people know when you actually care. And when you actually care, I don't care what you're doing, construction, nursing. When people see that you genuinely care, they want to be with you, they want to connect with you. And that's that's everything.

Aliya Cheyanne 44:43

Yeah, that is everything. So on that note, Adam, you also mentioned you hit 3,400 miles last year walking. And I've seen the transformation even in your pictures about how like doing these tours has even impacted your health. Can you talk a little bit more about just how this has helped to support your routine and prioritizing movement? Because something I've realized in a lot of conversations with creatives and entrepreneurs is a lot of people, because of that 80-hour work week or that 12 to 14 hour day, like they're not set aside that time for self-care and movement.

SPEAKER_07 45:22

Yeah, I don't go work out anymore because I'm gonna go walk 20 miles today. So no need to do that. I I think it's been really helpful to me. I think I'm not saying like I'm the most fit person ever. I'm not gonna go run a marathon, but yeah, I have an endurance that you know, I can get out the door at seven o'clock, be home at 10 o'clock, and I'll be fine. Yeah. I can do it again the next day. Usually by about day nine or 10, I need to take a break, but there is, it is, it has been a healthful experience mentally and physically to be active. Um, the only thing that ever gets too much of a workout is my voice. Every once in a while, I'll have to like, I'll come home and I'll be like, I'm not saying anything that my wife should like, you're not talking. To me, I'm like, I've talked for eight hours.

SPEAKER_03 46:02

Yeah.

SPEAKER_07 46:02

I'm not talking for three. So and she'll she'll get that. But uh yeah, um again, I think that's also about whatever those mechanics, the the synapses, and you're firing your adrenaline, you're working out the body as a muscle as much as you are the brain. And I think um that's good, that's just healthy. Yeah, just say, I'm not doing an Iron Man tomorrow, but yeah, you know, you set me out in the day. I'm going people, and I understand when people come here, walk in New York is a different world.

SPEAKER_04 46:27

Yes.

SPEAKER_07 46:28

And I tell people all the time, like, you're gonna walk 12,000 steps with me in the first four hours. That's more than you did last week.

Aliya Cheyanne 46:36

Yeah.

SPEAKER_07 46:36

So it's okay. You've got to, you know, be here a couple days, you'll get your New York legs.

Aliya Cheyanne 46:41

Yes.

SPEAKER_07 46:42

But I think you also know walking in New York isn't walking anywhere else. It is magical. This city is, and I always tell people, especially with the parents with kids, let the city do the work. Go go go walk down, you know, Sixth Avenue and see Radio City, and then go see, you know, that weird store with the coffee shop that's spelled with a Q or whatever. Let the city do the work. And and that walking disappears.

Aliya Cheyanne 47:07

That's so true. There's a creator and an influencer that I like, and she in the summer when the weather's nice, she loves going on her 14-mile walks in the city, just going running errands, like just walking just to walk, like doing everything in between because there's just so much to see and so much to do, and it never gets old.

SPEAKER_07 47:25

So it doesn't ever get old, that's true. And there's more always more to see. I I've probably seen 10% of the city, 20% maybe. Wow. And that's a lot. There's just so much. I even, you know, as I go through social media, I keep a running list of, oh, I need to check out that neighborhood, or oh, there's this museum that I never saw. Just a week or two ago, my wife and I was at Empty Day. We went out to Queens, we live in Queens, but another area of Queens, and there's this amazing little museum. It's an old house from a guy named Lewis Latimer. I don't know if you've ever heard of him, but he's um, oh my god, he's uh he didn't invent the light bulb, but he was on Edison's team, but he created the filament that made the light bulb possible for everyone else. And you go, why are we not? So we spent like an hour in this one little house, and we're like, how great is that?

Aliya Cheyanne 48:12

And you know, so yeah, that's super cool. I'm in the Latimer House's like newsletter. So they send out stuff all the time when they have like small gatherings, events, like workshops, like shows, like things, different things going on. So that's such a cool touch point.

SPEAKER_07 48:27

There's a there's a bone museum in Brooklyn. I gotta go figure out what that's about. I don't know. There's a bookstore in the East Village that's all about animals. I gotta go find it, you know?

Aliya Cheyanne 48:35

So Yeah, there's always something. I love it.

SPEAKER_07 48:38

There's always something.

Aliya Cheyanne 48:39

Yeah, and I feel like, especially as I've gotten older too, even revisiting certain parts of the city with friends, sometimes I'm just like, wow, these are my old stomping grounds. It's like you almost forget if we haven't been there or seen it in a while. And I'm just like, it's always nice to be reminded that there's still so much magic and there's still so much to see.

Meaningful Moments At The Memorial

SPEAKER_07 48:57

So I think it was a few months ago. It's funny you said that I was I was in um Central Park. I was given a tour, and we were at Bethesda Terrace, and it was right in the middle there, and we were just, it was just a glorious day, like the middle of autumn. And I just kind of sat there and my guests were like, What's going on? I'm like, I live here, like I can't believe I I've been here 14 years, and I'm like, I can't believe I live here. And like to feel that all the time is it's amazing. And that's what I want my guests to feel. Like, I'm here.

SPEAKER_04 49:24

Yeah.

SPEAKER_07 49:24

And that's what that's what the city brings. You know, how do I how do I give that to them in the way that's best for them? And I love that you feel it. I love that you can go to the same places over and over and go, yeah, yeah, it's New York.

Aliya Cheyanne 49:36

Yes, absolutely. That's so true. Adam, this has been so good. This has been such a fun conversation. Thank you for sharing so much. Thank you for showing up. You're welcome. Such incredible energy. And really wonderful. Can you let folks know where to find you, support your work, how to book a tour with you, all of the things.

SPEAKER_07 49:56

Yeah, no, so I have a website which is Inowaguy.nyc. It's not.com. I couldn't get that. So it's Inowy.nyc. And on there, it'll show you kind of all the places I go. It'll tell you how to contact me. It'll tell you what I charge. I'm very transparent about what it is. Stalk me on social media. I'm on Facebook and Instagram. I don't do TikTok because I don't dance. But you know what's nice? I do a lot of posting and it's it's a mix of my stories of my guests, some cool things about the city, some just fun photographs, the occasional dog on the subway because that's cute. Um and so there's that. And feel free to reach out to me. I literally put my phone number and my email address on my website. Um, you're gonna get a call from me. There's no other guy that's gonna reach out to you. My cat is not calling you. Um, so there's that. Um, I'll reach out. And even if you don't book a tour, that's okay. If you need a little help, you need a little nudge, I'll happy out. You you now that you know me, you know a guy in the city.

Aliya Cheyanne 50:47

Amazing. Thank you so much, Adam. I'll be sure to link all of that in the show notes. This is really incredible.

SPEAKER_07 50:53

Awesome. Thanks so much, Leah.

Aliya Cheyanne 50:55

And thank you, everyone, for listening. Bye.