IAM826- Founder Shows Travelers Around Washington, DC

Podcast Interview with Rob Pitingolo

Please Note: This is a rescheduled episode from earlier this year (recorded in February 2020) with Rob. Due to COVID-19, we pushed back the schedule of this podcast but thought it was a great interview and wanted to publish it with Rob agreeing. While we published a special episode in place of the original podcast, and business hasn't picked back up for Rob. He's currently running tours by request but not at nearly the same volume.

Rob Pitingolo founded Trip Hacks DC to share his best tips and travel hacks with Washington, DC visitors. He hosts the Trip Hacks DC podcast and YouTube channel and is a tour guide who loves to show travelers around the nation’s capital once they arrive. Trip Hacks DC tours has hosted over a thousand guests since it launched.

  • CEO Hack: (1) Book- Side Hustle by Chris Guillebeau (2) Think a little bit outside the box
  • CEO Nugget: Think beyond me
  • CEO Defined: Making sure customers gets exactly what they want and leave happy



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Full Interview:


Intro 0:02
Do you want to learn effective ways to build relationships, generate sales and grow your business from successful entrepreneurs, startups and CEOs without listening to a long, long, long interview? If so, you've come to the right place, Gresham Harkless values your time and is ready to share with you precisely the information you are in search of. This is the I am CEO podcast.

Gresham Harkless 0:30
Hello, hello, hello, this is Gresh from the I am CEO podcast and I have a very special guest on the show today I've Rob patina Lowe of trip hacks DC Rob is also having a show.

Rob Pitingolo 0:39
Thanks, Gresh. Glad to be here.

Gresham Harkless 0:41
Super excited to have you on Rob. I really appreciate you for hopping on the show. And what I wanted to do is just read a little bit more about Rob so you can hear about all the awesome things that he's doing. And Rob founded trip hacks DC to share his best tips and travel hacks with Washington, DC visitors. He hosts the trip hacks DC podcast and YouTube channel isn't it is a tour guide who loves to show travelers around the nation's capitol once they arrive? trip hacks DC tours has hosted over 8000 guests since it launched. Rob, are you ready to speak to the imcl? community?

Rob Pitingolo 1:09
Absolutely. Let's do it.

Gresham Harkless 1:10
Let's do it. Let's make it happen. So I wanted to kick everything off and hear a little bit more about what I call your SEO story. What led you to get started with your business?

Rob Pitingolo 1:18
Sure, absolutely. Well, I've been a tour guide now for eight years. And I've done trip hacks DC for three, we're about to start year four just at the time that this podcast goes live. And so as a tour guide, I have been showing folks around Washington, DC, I love doing that. And I always kind of wanted to branch out from just being a tour guide working for a tour company and to do my own thing to have my own company. And it took a while to get there. Because the big challenge in this industry is that it's so heavily driven by advertising. And it's hard to outspend the big guys when you are just getting started and when you don't have a lot of resources off the bat. So that's why I started the trip hacks DC YouTube channel and podcast that you mentioned, I give my best tips, tricks and travel hacks to folks who are visiting Washington DC. They get to know me a little bit. And then hopefully they you know, watch enough videos, listen to enough podcasts that they decide, hey, I want to have this guy show me around when they come.

Gresham Harkless 2:11
Yeah, it makes so much sense. And I know it probably varies, you know, I'm sure you talk with the people that come to DC and how long they're gonna be here. But there's literally I grew up here. So there's literally so much that you can do so many places you can go that sometimes you get overwhelmed and you need somebody that has that expertise, they can kind of probably guide you as you're able to go through your your visit.

Rob Pitingolo 2:31
Absolutely, it's very overwhelming when especially if you've never been here before, when you're just looking at a list of all the things that you can do all the museums you can go to on the sites and the fact that there are over 100 hotels in Washington DC, not even to mention the suburbs. So just trying to navigate all of that when you're planning a trip is challenging. And I get that and I think that's what's appealing to a lot of people when they find the YouTube channel and podcast.

Gresham Harkless 2:53
Yeah, absolutely. Me too. Anyway, you can find an easy button. That is always the way to go. So I know you touched on it a little bit, I want to hear a little bit more on like some of the things that that you might have on the YouTube channel, the podcast and some of the content that we could find there.

Rob Pitingolo 3:07
Yeah, so the YouTube channel, I try to do about five to 10 minute videos typically closer to five minutes. And they're just tips that you can use for your trip. So my most popular video by far, it's always been the most popular video is how to ride the DC metro. And to you and me, we live here. We've lived here a long time, it's it seems obvious, it's just something that's second nature. But I realized that a lot of people who visit their you know, this is a big city. And you know, we take that for granted, but they have maybe have never written a metro or subway before. And so it can feel overwhelming. They want to make sure they're doing it right. And for every person who tells me that they stood on the correct side of the escalator because of my videos. I take a little bit of pride in that.

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Gresham Harkless 3:47
Yeah, well, we laugh because I know exactly what you mean, I've been in so many times where I've gotten on the wrong side, and you have to run all the way over because the train is coming over. But I know that could definitely be frustrating, you know when that next train comes. But you're absolutely right, those, you know, simple things that we take for granted. Sometimes you need to have that information. So again, it's great to have kind of like a resource that allows you to do that.

Rob Pitingolo 4:09
Absolutely, for sure. Yeah. And the podcast is great, too, because it lets me just like this podcast that we're doing now. It lets me have guests who bring their own unique perspectives and experiences. So for example, I'm not a restaurant expert, I don't eat it very many restaurants. And people find that surprising. But you know, it's tough to eat at restaurants all the time. They're expensive, and we've got lives we've got stuff going on. So I've been able to bring in people, for example, who do eat it, a lot of restaurants, restaurant editors, food writers to talk about the best places to go. And to me that's great because I get to share some expertise that I personally don't have.

Gresham Harkless 4:41
Yeah, absolutely. And I think that's really like the beautiful thing for like podcasts and YouTube channels. Again, opportunity to connect with people is that you don't have to know every single aspect but sometimes you just need to know who to call or who to reach out to or what video to go to or podcasts to listen to in that case and you have people that really focus on that and really have tried, you know, all the time. For restaurants, so you can just kind of lean on them for their expertise.

Rob Pitingolo 5:03

Gresham Harkless 5:04
Awesome. Awesome. Awesome. So now I wanted to ask you for what I call your secret sauce. And it can be for you personally or your business. But what do you feel kind of sets you apart and makes you unique?

Rob Pitingolo 5:13
Well, I think what the reason why people sign up for tours, with me specifically is because they get to know me, that's not something that you typically get when you're traveling to a new place. You look up, you know, tours in whatever city you're going to, and you find a whole bunch of tour companies, and options and all that. But it's very rare that you actually know who the tour guide is before you show up. And so that's one of the that that was the secret sauce that really got this going and made it work initially. Now, of course, one person doesn't scale. I know a lot of your guests are one person operations. And so eventually, I had to bring in a team. And that was a challenge at the beginning. But I've really been able to start building some trust around my team so that people are now excited to go on tours with them as well, in addition to just me.

Gresham Harkless 5:55
Yeah, absolutely. And definitely and correct me if I'm wrong kind of sounded like you said this before. You also even I guess before somebody actually goes on a tour or college, it sounds like you start to build a relationship through some of the the mediums that you have the podcast, because you said they get to learn a little bit more about you.

Rob Pitingolo 6:10
Yeah, absolutely. I think there's always this debate in the business world about how many touches you need to make with a potential customer before they eventually buy from you. And I've heard anywhere from seven to 30. Who knows what the real number is. But you know, there's over 100 videos on that YouTube channel. There's 20 podcast episodes right now. And so if people watch 20 videos, are they listen to 10? podcasts? That's a lot of time that they're spending with me, and really building that relationship before they even get here.

Gresham Harkless 6:36
Yeah, absolutely in it. And then it just kind of shows your expertise. And I think, again, that's a beautiful thing about this day and age is that we have the opportunity to kind of showcase our expertise, you know, and interview people. And then of course, take people on tours, which is the fun thing to do, I'm sure. Absolutely. Awesome, awesome. So I wanted to switch gears a little bit. And I want to ask you for what I call a SEO hack. So this could be like an app or a book or habit that you have. But what's something that makes you more effective and efficient?

Rob Pitingolo 7:03
Well, the the book that kind of launched this whole thing was the book side hustle by Chris guillebeau. Because I did start it as a side hustle, I didn't just quit my job. And you know, jump into this, I really built it up, in addition to my job, and it worked perfectly, because my day job is a typical nine to five office job. And most people who come to Washington DC, want to take tours in the evenings. And so it worked out perfectly where I could work my job, and then leave the office and go right out to the National Mall, give them a tour. So it was really great to just have that, you know, idea that this can be a side hustle, it doesn't have to be something that you go all in on. And I was able to build it up slowly, but surely, and I'm really, really happy that I got going that way. The other thing, you know, my SEO hack is to always think a little bit outside, you know, outside the box. And I know that it's probably something that a lot of people say but for me, you know, I think about SEO, you know, there's tons of tour companies in Washington, DC, and they're all fighting over the keywords washington dc tours, Washington, DC walking tours, and it's it's tough, you know, I'm not gonna say it's impossible, but it's tough, no doubt about it. And so I thought, well, you know, maybe I can't correct Google. But I think I can correct you too, because none of these companies are over there. And so I focused on SEO, but I focused it on YouTube instead of on Google. And really, that was the hack that really put me over the edge.

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Gresham Harkless 8:23
Yeah, that makes so much sense. And I definitely, you know, appreciate you for, for breaking that down. For one. I mean, even just from understanding, I think sometimes we get that we want to start a business or we might want to do this or take whatever step and we almost feel like we have to do it at a snap of a finger. But the process that it takes to do that. And it is crazy that the the schedule that you have perfectly aligned with the schedule that every that your target market had as well, too. So you were able to kind of hit that that very sweet spot. But I think that is, you know, remarkable and that you were able to scale that. But then to like you said, I think when you get into your industry, you start to see that there's certain opportunities that you want to be aware of, so that you can kind of take advantage of that.

Rob Pitingolo 9:03
Yeah, and in many ways, it's just lucky that the schedules aligned that way. But I also knew that that was the case, because I've been a tour guide for years prior to that. And I knew that for the company that I worked for the most popular tour by far was the evening monuments tour. And so if I hadn't done that I might have been, you know, thinking, Oh, people want to go in the morning or they want to go with lunchtime, but because I already had that experience. I already knew what was going to work in Sunbury. I'm very happy that I had that experience going in.

Gresham Harkless 9:31
Yeah, absolutely in any and that's why, you know, a lot of people that start business, they do have some type of interning or you know, maybe working with a coach or consultant or something so they can kind of elevate and get that expertise and that information so that they can shorten the learning curve, so to speak. So you're not doing, you know, morning tours for six months and then trying to figure out why it's not working as well as you would have hoped. You already already have that kind of leg up on getting started. Yep. Awesome. Awesome. Awesome. So now I wanted to ask you for what I call A CEO nugget. So that could be like a word of wisdom or a piece of advice, or something you might tell your younger business self.

Rob Pitingolo 10:06
Yeah, one thing I would tell my younger business self is to think beyond me. And what I mean by that is, you know, I built this company around me, and me as the face of it, I'm in all the videos, I'm the host of the podcast. And so there's only one of me. And during some busy times of the year, like during the Cherry Blossom Festival in the spring, people book up my tours, you know, weeks in advance, and then people contact me and they say, hey, I want to go on a tour with you, what can I do? And I said, Well, sorry, I'm already booked. But I've got this other great tour guide who can go with? And at the beginning, they would say, and now No, thanks, not interested. And so that was really discouraging, because I realized that there's only one of me. And when one time, you know, booked up, then that's kind of it. So I would tell my younger self to think forward to think, to train people to train the potential customers to think beyond me as well.

Gresham Harkless 10:55
Yeah, that's definitely a huge nugget. And kind of just reminds me a lot of the E myth where you know, you're really great at what it is that you do. So you have that business and you start the business. But a lot of people want to, you know, work with you, they want you to kind of have that hands on. And there's only so much we can scale ourselves, we only have the 24 hours in a day, as much as we have. So it definitely sounds like you've been able to do that as well to have you found like there's certain, I guess, things that you've done that has really, you know, helped you to be able to build that connection with other team members, in addition to yourself?

Rob Pitingolo 11:28
Yeah, well, one of the great things about the videos is that people can watch those before we start talking about having them give tours for me, and they can decide, hey, this is something that I'm aligned with that I'm on board with, or now this isn't, this isn't for me. And so it kind of makes it easier for people to decide whether they want to do this or not, before they even get started. It's also good. Now I have a lot of reviews for some of my other tour guides. And that's a big thing in this industry. And you know, when you're researching, travel, you're going to the reviews, you're seeing what people are saying and the reviews are overwhelmingly positive. Now, at the beginning, every single review said, hey, my tour with Rob was great. And I'm very happy, very proud of those. But I really needed some that said, Hey, the other people are great, too. And I finally have those. So when people are researching, they're saying, Oh, it's not just Rob, it's these other people as well. And if I get a tour with them, I'm gonna be perfectly happy with it.

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Gresham Harkless 12:20
Yeah, that makes so much sense. And do you find if you know, a lot of times, you know, when building a great team and having people in place, you always want to have complimentary people as well, too. Do you find that, you know, as you said, I'm not I don't know if one of your restaurant guys is like specifically focused on food, but something along those lines where you have your strengths, and they have their strengths, and they kind of gives you that full complement of people that they can reach out to?

Rob Pitingolo 12:43
Yeah, haven't quite gotten all the way there yet. That's that's kind of a next step is to using people's skills. Right now. We're all kind of just leading the same tour. It's just a monuments tour in DC, which is very popular, don't get me wrong, but it's also not really that unique. Whereas like a food tour, or a coffee tour, things that people might be really good at leading. And I've kind of had conversations about doing that. We haven't really branched into it yet. But your idea is a very good one. And I'm definitely working towards that. Awesome, great,

Gresham Harkless 13:13
great to hear and definitely, you know, wait for it. And I agree, I think that's definitely great, you know that you are already thinking about that you already have that. So you plan. And so that just means that it's going to be sprouted sooner rather than later. So definitely appreciate that. And now I wanted to ask you my absolute favorite question, which is the definition of what it means to be a CEO. And we're hoping to have different, quote unquote, CEOs on the show. So Rob, what does being a CEO mean to you? It means making sure that every single customer

Rob Pitingolo 13:38
gets exactly what they want, and leaves happy. And so as CEO, I'm lucky, this is still a small business, I can have a personal interaction with every single customer, whether they go on tour with me or not. And I truly believe that that's one of the reasons why when you go and look at the reviews on TripAdvisor or Google, that they're so overwhelmingly positive, but to me being CEO means being in charge of the customer experience, and making sure that it's an excellent one, and that they're all going to leave happy and that they're going to tell their friends that this is something that they need to do when they come to Washington DC.

Gresham Harkless 14:09
Absolutely. That makes so much sense. And I think so many times we get lost in the sauce, I guess you can say and we're not looking and reminding like why we do what we do to have that sort of satisfaction from the customers. And starting with one customer than two, and so on and so forth. It starts to build and it starts to grow. But I think if we lose that focus, no matter you know, if we have a small business, medium size, whatever size our businesses, and we lose kind of like the essence of why we started and what it is that we're doing.

Rob Pitingolo 14:35

Gresham Harkless 14:36
Awesome. Awesome. Awesome. Well, Rob, truly appreciate that. And I truly appreciate your time even more. What I want to do is pass the mic so to speak, just to see if there's anything additional you can let our readers and listeners know and then of course how best they can subscribe to the YouTube, find your podcast and find out about all the awesome things we're working on.

Rob Pitingolo 14:52
Yeah, I hope that anyone who's listening and wants to jump into this just just jumps in. And just like me, you don't have to quit your job. You You don't have to spend a ton of money. You just pick up a few books and get some inspiration, listen to podcasts just like this one, and then jump into it now don't, if it doesn't work out, it's not the end of the world. And I've certainly had some other ideas that didn't work out. And it wasn't the end of the world. So I hope that your listeners can, can take that and appreciate it, like I did, for getting in touch. Trip hacks, DC comm is the website. And of course, the YouTube channel is also called trip hacks, DC. So as the podcast, you can find that on the website or search in some of the podcast apps, if you use one that you particularly like otherwise, we're also on Facebook, Instagram and Twitter, as well.

Gresham Harkless 15:36
Awesome, awesome. Awesome. Well, thank you so much. Again, Rob, we will definitely have those links and information in the show notes as well too, to make it easier for everybody. But thank you again for that reminder as well, too. I think so many times we get caught up in and then try try try and we don't actually do and understanding that sometimes the things that don't work out are part of the process. We all have things that didn't pan out as well as we would have hoped. But the difference is that we continue to take action. So I appreciate that reminder and appreciate you again too, and I hope you have a phenomenal day.

Rob Pitingolo 16:04
Of course you too.

Outro 16:06
Thank you for listening to the I AM CEO podcast powered by Blue 16 Media. Tune in next time and visit us at IAMCEO.CO. I am CEO is not just a phrase, it’s a community. Be sure to follow us on social media and subscribe to our podcast on iTunes, Google Play, and everywhere you listen to podcasts. Subscribe and leave us a five-star rating. Grab CEO gear a This has been the I AM CEO podcast with Gresham Harkless. Thank you for listening.

Mercy - CBNation Team

This is a post from a CBNation team member. CBNation is a Business to Business (B2B) Brand. We are focused on increasing the success rate. We create content and information focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts, ( and videos ( CBNation is proudly powered by Blue16 Media.

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