425 Madeline Jhawar: Beyond The Obvious

Ever loved a hobby or activity so much… that you turned that love into a profitable business? The most successful entrepreneurs and business owners start out with a burning passion and today we talk about how to make that passion and purpose profitable.


I’m Melinda Wittstock and today on Wings of Inspired Business we meet an inspiring entrepreneur who turned her passion for traveling in Italy into a thriving company creating custom vacations for curious travelers.

Madeline Jhawar runs Italy Beyond the Obvious, founding her business 11 years ago, after living and working in Italy for 5 years and she guided weeklong hiking and biking tours in the luxury sector.

Today she shares how she made the leap into entrepreneurship – plus her innovative business model and now how she is scaling her business.

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Madeline has created a unique business model – unlike the traditional travel agency and its commissions-based fee structure. Beyond the Obvious has an unusual fee-for-service business model – serving high-end clients who want to connect deeply to the culture with customized and magical experiences. Madeline has attracted a lot of attention from travel publications and podcasts – and says she regularly gets contacted by destination experts who tell her “you have my dream job! Please teach me how to do what you do!” After many years of requests, Madeline launched an online course in October of 2019 that teaches anyone with niche travel expertise how to create an online business creating custom vacations.

Madeline has lived in 11 cities and now resides in the heart of Silicon Valley with her entrepreneur husband and teenaged children.

So are you ready for Madeline Jhawar? I am. Let’s fly!

Melinda Wittstock:         Madeline, welcome to Wings.

Madeline Jhawar:            Hi Melinda. Thank you so much for having me.

Melinda Wittstock:         I’m excited to talk to you and about all things Italy and travel. I love to travel. Italy’s one of my favorite places in the world. And I’m curious how you got into the travel business to begin with and how you’ve grown this business. So let’s start with what was the spark?

Madeline Jhawar:            Sure. I lived in Italy for five years, so I spent a year there as an exchange student and then I went back as a hiking and biking tour guide. I worked for Butterfield and Robinson, guiding week long hiking and biking trips. And then I went back as a Corp, I joined corporate America and I went into international operations and I went back as an expat, as a southern European operations manager based out of Milan, for a couple of years. But once you work as a Butterfield and Robinson tour guide, everybody was like, “Where should I go? What should I do? Where should I go? What should I do?”

So while I was working at Arrow Electronics in international operations, I was on the side, I was planning vacations to Italy for my friends and family and that was for about 10 years. And then that job just had a lot of travel and I just couldn’t. I had a couple kids and I was like, “I cannot travel 50%.” I mean, my region was, by that time we moved to Boston and my “region” was Singapore, Bedford, England, and Reno, Nevada, which was a weird region, but it was too much travel.

And so I just was like, “Well, this thing I’ve been doing anyway for 10 years might, maybe people will pay me for it.” And I looked into becoming a travel agent and I didn’t understand the business model. The travel agent business model is about selling pre-created packages that someone else created. And there’s a lot of middlemen and it’s about charging the client and then getting commissions. And I was like, “I don’t need middlemen. I don’t need packages. I already know the local farmers.” I’d already been a tour guide on these bucket lists. These trips that I was guiding were five star trips. They were luxury trips. And so I knew that client very, very well and I knew how to put together a trip like that. And so I just said, “Let me put up a website. Let me charge fees.” Because I had a professional income and I was not going to take a pay cut. I was like, “Let me just charge these so that I get paid what I’m worth. And then let’s see what happens.” And that was 11 years ago.

Melinda Wittstock:         And did it just take off?

Madeline Jhawar:            Not at all.

Melinda Wittstock:         What were some of the biggest moments where you’re like, “Oh my God! Am I doing the right thing? Ah!” In those startup birthing pains, I guess.

Madeline Jhawar:            Totally. So I was afraid to say, “Pay me, hire me.” That was a big … So what I started by saying, “Okay, I’m an Italy expert. I’m going to showcase my Italy knowledge.” And so I started writing a blog and I was like, “People will just ask me to plan their trip once they see how much I know about Italy.” Well, that didn’t happen. People would read my blog, take the information on my blog and go plan their own trips. They didn’t even know that I was offering a service because I had one little-

Melinda Wittstock:         Because you hadn’t said, right? Yeah. So many people, so many women do this, right? We forget to ask for the sale.

Madeline Jhawar:            Yeah. And so early on somebody said to me, “I don’t even know that you are running a business. I think you’re just offering free Italy advice. You have to be clear. You have to put it out there. You have to say like, ‘I am awesome. I am an expert. Here’s what I can do for you. Here’s why you should hire me. Hire me please. Or hire, I’d love to work with you.'” So there was that. So I really had to change the entire positioning of, it was really a blog with like a one line that said, “Hire me.” And I had to change it into a website that said, “This is a business and click here for the blog.” and so it was a total flip. So that was a big one. And now I have absolutely no problem. Now I’m like, “Here’s what I can do for you. I can make a fantastic dream Italy …” I have no problem saying what I can do. But that was a big shift for me.

And then the other big thing that I spent a lot of time and effort on is really the internet is so crowded. There are so many people looking for so many answers to their questions. And I have spent a lot of time targeting the exact right client. There’s a client that is a really, really, really good fit for me. And when that client finds my website, they recognize themselves and they say, “Yes, this is what, this is the service I need. This is the price point. This is the …” I have a travel philosophy on there. They read my travel philosophy and they contact me.

So I have really spent a lot of time honing the services and honing the message on the website over the years. And it’s very effective because I get a lot of people who find … so first of all, we’re at 50% for, I don’t do any paid advertising. I get, right now, I’m at 50% clients who find my website and hire me and 50% referrals. And very often, those clients that find my website are just ready to go. They read the travel philosophy, they’re like, “Yes, yes, yes.” They see the services. They’re like, “That’s what I need.” They read the testimonials. They say, “I want that.” And they call me and they’re like, “Hey Madeline, I’m ready to go.” So, and that took a lot of fine tuning.

Melinda Wittstock:         Right. I mean, that is the best way to sell. And particularly for women, I think when we’re very clear about our unique differentiation in the market and we say so in a way that’s really clear and we’re very clear about the benefits people get and we know exactly, exactly the people we’re selling to. We’ve done that work. We’ve taken the time to really dig into that. What are their three o’clock in the morning moments? What are the things that are going to allow them to purchase? When you do that work, oh my goodness! Selling becomes super, super easy and I think it’s a weird, I don’t know whether it’s … I’m just going to pick up there. It’s women attract quite easily. I don’t know whether we should or whether we’re at … I’m going to say this again, sorry. I’m not sure whether we’re at our best when we’re out there with a spear hunting the wildebeest, but it sounds like you got this system in place that just brings you leads, brings you the right people, qualified people. How long did it take you to really get that perfected and in place?

Madeline Jhawar:            I mean, it’s an ongoing process. I just … so I was probably working … so I’m in year 11. Probably in year two, I was working full-time, but I wasn’t working efficiently. So I was working lots of hours, but I didn’t have a lot of clients. And then I would just keep raising my fees. So I would be working full-time and I couldn’t take any more clients and I’d have the demand. And so I increased my fees and I think I increased my fees in year four, five, six, something like that. And then in about year seven … actually no. It was year five, I hired someone because I was solidly in the luxury category, but I was continuing to tweak. We did raise our fees again in 2018, but I was continuing to kind of tweak the services based on what the clients told me they wanted.

So, for example, about five years ago, I added a pre-programmed GPS to one of my services where I would take the GPS program it with all the client’s destinations, and then I would ship it to them in the mail as part of my highest end service. Well, travelers don’t need that anymore. Because data, international data plans have gotten so reasonable that you just use your smartphone and you plug it into your Italian rental car just like you would here. So then I removed that service based on clients were telling me, “Well, I don’t really need that. That’s not really a value add.”

And then the other tweak that I did just recently, just about five months ago this year, is I removed my lowest end service because what I find that, I don’t know if you found this too, is that the people that paid me the least were also the most work and the least-

Melinda Wittstock:         Oh my goodness, yes. I found that too. Whenever I’ve really kind of discounted or waived my normal price or gone too low, those people are more likely to not value or complain about the money or they’re going to be in a scarcity mindset or of nickel diming.

Madeline Jhawar:            Yes. Yeah, exactly. And I was getting plenty of high end clients who were happy to pay me. So grateful. And I was like, “I don’t need these whiners.” I mean, I don’t want to call them whiners. They were still … They’re just much, they weren’t the right fit client. They were just a lot of work for me and not as appreciative. And I was like, “I want to work with people who are super appreciative and happy to pay me and not trying to nickel and dime me.”

Melinda Wittstock:         Absolutely right.

Melinda Wittstock:         So we’ve been talking about your ideal avatar and the fact that you’ve done all this in depth and to who your ideal customer is. How did you learn that and who are they?

Madeline Jhawar:            So I started with the Butterfield and Robinson traveler that I had gotten to know. I had spent 24/7 with these travelers. I did three seasons for Butterfield and Robinson because they’re hiking and biking tours. They’re spring and fall. And so each season is six trips. And so I do six trips back to back and then I take the summer off and then I do six trips back to back and take the fall off. And so I spent a very, very intense amount of time with these types of travelers and I knew them very well. And so that’s who I created my, and that’s who I still service. That’s who I created Italy Beyond the Obvious for because I knew the types of trips that they loved and I knew the types of trips that would really wow them.

And that traveler is, first of all, very culturally curious. And that’s what I love about what I do is the people that I work with really want to connect to the culture. They are very intellectually curious as well. So they want to … They’re curious about archeology and art and history, but also nature. They’re usually very active. So they love hiking and biking. And we do a lot of active trips, but they also, a lot of them say “I’m on vacation. I have nothing to prove. And so I want to go for a hike to a winery and then I want to have lunch at the winery and enjoy some wine and then I’m done. I don’t need to hike 12 miles a day for seven days in a row.”

And so we do a lot of, we work with a lot of people, as I say, who are culturally curious and intellectually curious, but they also are busy people. They don’t have much time off. And so, first of all, they don’t have time to create a trip, but they also appreciate how much work goes into creating a custom vacation. And because often they have backpacked through Europe when they were younger. We actually don’t work with very many people who have a brand new passport and say, “I’m leaving the US for the very first time.” I work with people who are quite well-traveled and they understand the challenges of being in a foreign country, in a foreign language, in a foreign currency, and jet lag and all of that. And they also value expertise. They’re always professional people. They are often consultants themselves where they offer a deep, specific service to their clients. And so when I tell them about my service, they totally respect it, understand it, and they’re happy to pay for it.

And then the other thing is back to the point about the limited vacation, they also, not only do they not have time to plan their vacation, but they also, the vacations that they get, I do a lot of like bucket list trips and dream trips and multi-generational family trips where grandpa’s taking the kids and the grandkids. And so these are really, they’re really important trips and they can’t afford for things to be going wrong and they can’t afford to be problem solving on their vacation. And so again, they turned to me and they just value the work that I do.

Melinda Wittstock:         That’s fantastic. And so much so that you have people coming to you saying, “Hey, how can I do this too?” So you’re spinning out, training people to spin out a whole bunch of businesses like yours. How did that come about?

Madeline Jhawar:            Yeah, I, for years, I’m all about sharing and uplifting everyone. I really believe that a rising tide lifts all boats. I don’t believe in competition. I don’t believe that are secrets. I don’t believe that if somebody says to me, “Hey Madeline, who’s your Rome guide?” I’ll tell them. I really believe in sharing information and that everybody sharing really helps everyone and which is a little bit of a different approach. If you talk to some travel agents, they’ll say, “Oh no! I can’t share my secrets because you’ll steal them.” And I’m like, “There’s no, my secrets are not better than your secrets. They’re different. And I can share them with you” and you’ll share, you’ll give the information to the right client. But the point I guess I was, is I’m trying to get across is I’ve always been very open with how to do what I do.

And so people, for years, have been saying to me, “Madeline, you have my dream job. Teach me how to do what you do.” And I say, “Fine. Send me some questions.” So they’d send me some questions. And I really thought, because I kind of built this based on what I thought was common sense over the years, I would just say, “It’s really not that tough, just do this, this and this.” And they’d write back and they’d say, “Okay, now I have 10 more questions.” And I’d write back and I’d say, “Okay,” and I’d answer the questions. And I was, I really believe that a fee for service business where you’re a destination expert and you’re putting together custom vacations, I believe that this can be an industry. It’s not an industry now, but it can be an industry. I see huge potential.

And so whenever somebody would contact me and say, “I want to do this,” I would say, “Yes! I would love to help you do this. I would love to help you be successful. Send me questions.” Well, there was this one woman who sent me, I kept saying, “Please send me questions.” And she sent me a six page Google Doc of questions. And I was like, “Okay, there is a lot more to this than I … it’s not just common sense, do these three things.” I mean, she really helped me see that there was a lot of things that I had answered and solved over the past few years. So that’s how the course started.

Melinda Wittstock:         And so what are some of the challenges in the online world, because it’s quite a bit different when you’re doing an online course for people. So did you do the usual like the funnel and the Facebook Ads into it and that kind of thing? Or was it more word of mouth? How did you find your clients there?

Madeline Jhawar:            So we have actually just launched. So I put through the initial five students a year ago and I said to them, “You guys are going to have to be patient because going to record lesson one and given your, then based on your feedback, I’m going to send you lesson two. And then based on your feedback I’m going to send you lesson three.” And then, I get these requests from people all the time. So I had those five initial ones go through. And then once I had the content, which was just recorded videos, then I had the course. And so then when people would contact me and say, “Teach me how to do what you do,” I would say, “I have a course.”

And so I’ve gotten another probably 10 people from that and we are currently in a soft launch beta where we’re doing testing because we put the material on the website and now anybody can access it. And so we’re actually launching. We’ve got the marketing plan ready to go. And so to answer your question, yes it’s Facebook Ads, it’s Google Ads, and it’s the SEO stuff that I’ve applied to my own Italy Beyond the Obvious website where I’m positioning myself as an expert and creating online content so people find me organically.

Melinda Wittstock:         And so it took you a while though, I’m imagining, to build up all those contacts and all that expertise in Italy and just knowing that market really well, all the hotels, the best restaurant, all the different, that some of knowledge. So for anyone, if I said, “Hey Madeline, I want to start a travel business and I want to start it in this particular country because I really love it,” it’s going to take me a long time to develop those kinds of contacts as well though, right?

Madeline Jhawar:            So not necessarily. So there’s a lot you can do. So in the, so this is the topic of one of the lessons of the course, which I call the Little Black Book. And so there are four components to finding great. There are four pieces: there’s the hotels, there’s the tours and activities, there’s logistics, and there’s restaurants. And because of where we are in terms of online research, you can use a method for hotels and restaurants rather than relationships and contacts. I teach the method for finding the best hotel for the client because when you’re not a travel agent and you don’t have this limited portfolio, you really could, you could … I’ll book an Airbnb. I’ll book a farmhouse. I’ll book a boutique hotel. I’ll book a big hotel. I’ll book an apartment. I’ll book whatever is best for my client.

And so really the key is to ask the right questions to the client and say, “What’s your price point? Do you want a suite? Do you want a view? Do you want to onsite bar or an onsite gym or a pool? Do you want a balcony? Do you want a big hotel or a small hotel?” And so you ask the right questions to the client. And then based on that, it’s really about the research method. And of course, I have my favorite hotels and a client might, based on their responses, I might be like, “Oh, I know the perfect apartment for you in Florence.” And so I do have those. But you can solve that through the method.

In terms of relationships, the guides are, the relationships are really important with the guides and the drivers. And for restaurants you can, it’s about the method. So some of it is about context and some of it is just about the way that you go about finding, doing online research.

Melinda Wittstock:         Right. Well, this is amazing. And so what’s next for you when you think of like it took you 11 years to build this amazing business and it’s going really well. Now you have this whole other business line. Where do you see it going in the next five, 10 years?

Madeline Jhawar:            Oh, I have a plan.

Melinda Wittstock:         Well, that’s good.

Madeline Jhawar:            Yeah. So for the travel course, I am, as soon as we get the marketing ball rolling and we get students enrolling on a regular basis, I’m going to be working on a certification program.

Melinda Wittstock:         Good idea.

Madeline Jhawar:            Yeah. And I actually have somebody who has already asked me. He’s like, “I need your certified students.” And I was like, “Okay, give me a year.” He’s like, “But I need them.”

Melinda Wittstock:         Yeah. That’s one of the best ways to scale a business, like any kind of coaching or training sort of business to do that. And it’s great because it grows. You have these net, you have these disciples, right, that love what they do and they go out and it’s great word of mouth and it’s a nice way to do the marketing piece of it as well. And a nice way to get a little bit of passive income coming in also.

Madeline Jhawar:            Yes, I’m hoping so.

Melinda Wittstock:         Yeah, that’s a nice model.

Madeline Jhawar:            And I mean, I don’t know, I don’t want people to just say, “Willy nilly. I took the Travel Beyond the Obvious course and put the stamp on their website” because I don’t know who these people are and whether they paid attention and whether they know what they’re doing. So the certification also then gives me a way to give my own stamp of approval. And on the other side, I have clients coming to me every single day saying, “Who else does what you do for other countries?” Every day.

Melinda Wittstock:         Mm-hmm (affirmative).

Madeline Jhawar:            So then I can now I have someone, if I have the certification course, I can then send them to people that I respect and trust.

Melinda Wittstock:         Yeah, you can expand geographically. I mean, this is so exciting. So when you were a kid, Madeline, did you know that you were entrepreneurial?

Madeline Jhawar:            No.

Melinda Wittstock:         No? [crosstalk 00:29:18] And so what was it? Was it just really the interest? Because people, some people are just like natural. They’re like, they’re six years old and they’ve got the lemonade stand and they’re just really entrepreneurial and that’s it. I find that so many women in particular start businesses just around an interest that they have or… we have so many life changes that when the interest coincides with the life change, that’s like the optimal time and so many women go into business. Was that more your story?

Madeline Jhawar:            Yeah, I think so. I think it was just, it was something I was doing anyway and it was both Italy Beyond the Obvious and Travel Beyond the Obvious were based on people asking me to do something that they wanted me to do. And I said, “okay, if you pay me” and both-

Melinda Wittstock:         [crosstalk 00:30:08] Right. Okay. So it came to you in a way?

Madeline Jhawar:            Yeah.

Melinda Wittstock:         Yeah, yeah, yeah. Well, that’s nice.

Madeline Jhawar:            I think about my childhood and I had a dog walking business and I even went door to door selling how have you popped the dandelion head off and you split the stem of the dandelion and you put it in cold water, it curls up into a really tight curl.

Melinda Wittstock:         Oh, I didn’t know that.

Madeline Jhawar:            Well, some friends of … we had, I was about seven and we made what we call dandelion curls and we went door to door selling them for 25 cents.

Melinda Wittstock:         Okay, so I’m going to disagree with you. I’m going to say that you were entrepreneurial as a kid.

Madeline Jhawar:            Well, I think you asked me whether I thought I was entrepreneurial.

Melinda Wittstock:         Oh right.

Madeline Jhawar:            I [crosstalk 00:30:49] thought I was.

Melinda Wittstock:         Well, we probably didn’t even know the word, right?

Madeline Jhawar:            Probably.

Melinda Wittstock:         I didn’t know the word entrepreneurial when I was a kid, but I did all kinds of other entrepreneurial things.

Madeline Jhawar:            Yes.

Melinda Wittstock:         But I had no idea what I was doing. It was just sort of like a natural thing. “Oh, hey let’s go sell this” or “Let’s put on a show” or “Let’s do this” or “Let’s do that,” right?

Madeline Jhawar:            Yes.

Melinda Wittstock:         And I always liked asking childhood questions because often the clues, when we, that Steve jobs quote about, “You can’t connect the dots moving forward. You can only really connect them looking backward and you start to see all the different things that you’ve done in your life that bring you to this moment where you are now” and it’s interesting that you had like dog walkers, a kind of tourist for dogs.

Madeline Jhawar:            Yeah.

Melinda Wittstock:         Right? There are some threads there. What do you think the biggest challenges are for women in business based on your own experience and what you see around you with other women that you know? We share a mutual network with Pinnacle Global Network.

Madeline Jhawar:            Mm-hmm (affirmative).

Melinda Wittstock:         I mean, what are some of the things that you see challenging women the most in particular?

Madeline Jhawar:            I mean, I think I’d like to just speak for myself here. I don’t want to put, I only because what I’m about to say, I don’t want to assume anything for anyone else. But I find the whole managing the household and the kids and running the business, such a tough balance in the sense of I don’t, I want to spend time with my kids and I don’t want to work 12 hours a day and I value cooking dinner and eating healthy and having a balanced life.

And I just find it such a challenge to … Sometimes people, they see that I’m at my kids, because I run my own business and I have such a flexible schedule, I can be at the kids’ concert at 2:00 PM on a Wednesday afternoon. And people see me and they’re like, “Oh, well you can’t be running that serious of a business then if you’re at this concert at 2:00 PM.” And I just get frustrated because I’m like, “No, I am super serious about my business. I’m doing really well. I make six figures. I have a team of four people and yes, I’m at this concert at 2:00 PM because this is important to me and my kids are important to me.” And so I really struggle with that.

Melinda Wittstock:         [crosstalk 00:33:12] Well, yeah. I call them civilians, right? People who do not run a business or are not entrepreneurs really have a hard time understanding this because their reality is so different. They kind of clock in, clock out in a way. There’s certain things that are demanded of them. They don’t have the flexibility to just go to an event at a school or whatever at two or 10 or whenever. Well, we do have that luxury to, but we work very hard. We just work at any old hour, any old place. It doesn’t really matter. You can still get it done. But yeah, I think juggling all that stuff without guilt or without apology is a big challenge for a lot of women. And I don’t know, I guess it just comes down to knowing what you really want and doing that.

Madeline Jhawar:            Yeah, yeah.

Melinda Wittstock:         Without fear of judgment from anybody else. I mean, that’s so, so important. I think it’s interesting, right now, women are at a very interesting place in the business world because we’re learning and getting more confident about leveraging our, what I’ll call, our feminine power, not an oxymoron, where we come at things in a, in a slightly different way. We can really leverage our empathy and our intuition and those sorts of what used to be called irritatingly soft skills, but are really, really important. And increasingly, I see a lot of men in the business world really wanting more of that and moving more towards that style of leadership themselves. So I think we have a really interesting and pivotal role to play in terms of how we remake business to suit the lives that we want rather than fitting into somebody else’s idea or a masculine idea of how a business should be organized. Is that something you’re conscious of in terms of like how to, “Okay, I’m a woman, so I’m going to do this differently.”

Madeline Jhawar:            Mm-hmm (affirmative). 100%. Yeah. Very well said. Yeah. Yeah. And I think … Isn’t there a state of California mandate that there has to be a woman on every publicly owned company board? Something like that or did that-

Melinda Wittstock:         I don’t know. But that would be cool if it’s true. And it would also be smart business because there’s some stats from NASDAQ and the DOW and venture capital funded companies where if there’s a woman on the board and on the executive team, not only do those companies survive, but they wildly, in every case, outperform those that do not have women in senior executive and oversight or board positions. And so I think that’s really encouraging. So perhaps California has just kind of figured out it’s not charity. It’s actually smart business.

Madeline Jhawar:            100%, yes. 100%.

Melinda Wittstock:         Right?

Madeline Jhawar:            Yeah, yeah, yeah.

Melinda Wittstock:         Oh, that’s so cool. Well, look, I’m going to have to get in touch with you the next time I go to Italy.

Madeline Jhawar:            I would love to help.

Melinda Wittstock:         And do that. I love it. Such a beautiful, beautiful country, like from top to bottom. It’s just gorgeous and I haven’t been back in a long time, so I will definitely look you up when we’re ready to go to Italy. And I encourage everyone else to do that as well. And also for anyone listening that’s looking for a another business or a new business or something, get in touch with Madeline and how can they do that, Madeline?

Madeline Jhawar:            For Italy travel planning, they can find me at italybeyondtheobvious.com. And anyone interested in the travel planning course can find it at travelbeyondtheobvious.com.

Melinda Wittstock:         Well, wonderful. Well, thank you so much for putting on your wings and flying with us.

Madeline Jhawar:            Thank you, Melinda. It’s been so fun.

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