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Ep. 206: How this former Uber employee became a remote business consultant and startup founder with Jen Hong

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In this week’s episode, I speak with Jen who is an experienced Go-to-Market consultant who launched a travel tech startup (Levantr). 

Jen became a digital nomad and started a consulting business after being laid off from Uber due to the pandemic in 2020. 

Due to her upbringing, she had to travel often even as a kid, and strongly believes that early exposure to different cultures is crucial to reducing prejudice and bias in the world. 

Listen on to find out how Jen has been able to become a digital nomad and launch a travel tech startup.

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My Offbeat Journey: Make your lifestyle the goal, not your income!
Ep. 205: How this mompreneur built an online coaching business that helps badass women with Cat Del Carmen
Ep. 204: How this remote travel and non-fiction writer helps badass women connect to their personal power with Kelly Lewis.



Hey, everyone. Thank you so much for being here. I am so excited for my guest today. Her name is Jen. 

Hey, Jen, how are you? 


Good. How are you? Thank you for having me, Debbie. 


Thank you so much for being here. Can you tell us more about you and why you live an offbeat life? 


Sure. So I lived in New York for most of my 20s and after going through corporate job after corporate job, just really felt like this felt really unhappy and wanted to take a year off and kind of figure out what I really wanted to do.

So I decided to travel around and move to Australia temporarily. I just traveled around for a bit with my main base being in Sydney and took a bunch of classes, courses I’ve always wanted to take that had nothing to do with my job. 

I’ve always kind of liked freelance a little bit just because sometimes I felt like I wasn’t really learning much at my current job and just wanted to connect and broaden my horizon. So I took on projects and when I was done with my gap year, I was thinking about moving back to New York City to get into the startup scene and then ended up getting a job at Uber here in Australia. 

So kind of sort of went back to that corporate life ’cause Uber is now a huge enterprise. And when I got laid off in May because of the pandemic, that really kind of pushed me to explore the remote options. And it was scary: looking for clients and trying to figure out what my online business needs to be. 

And after kind of getting into the rhythm of working remotely and kind of getting clients for my remote consulting business, I really realized that I never want to go back to the corporate environment. So really kind of committed to being that digital nomad while traveling across Australia because now, here in Australia, traveling is relatively back on. 

So just kind of going to different cities and experiencing what this great country has to offer while kind of building up my remote consulting business as well and also kind of launch my own startup. So it’s been an interesting time. 


I love that and it’s such a huge thing because we’re so familiar and so used to the hustle and bustle of New York City. And to leave that all behind and to do something else so completely different and because you were able to do that it took you pretty much around the world and the opposite part of the world. 

When you were deciding that you wanted to do this, I know you got a job for another big company, what was it like to prepare for that change? Did you do anything that allowed you to get into this new lifestyle much more smoothly, especially when you left Uber and now you’re doing something on your own?


Yeah. I think that the first step was talking to other people. Kind of finding a community of digital nomads and freelancers to understand what this lifestyle actually entails and how you kind of navigate. Like, how do you even go about finding a job? ‘Cause we all have to, especially if you’re a digital nomad who wants to travel while working, have a revenue stream. 

So just kind of understanding what other people have done and that reduces, I think, the fear of the kind of getting into the lifestyle of a digital nomad. And that’s how I started and I think the pandemic really forced a lot of interesting trends in terms of a lot of companies started creating products and improving products to cater to remote work. I think that was really helpful.


It’s so great when you’re able to find communities, especially in the digital nomad space, because it seems really great when you’re looking at it from the outside. And you see beautiful photos of people working from everywhere and then you talk to actual digital nomads and you see and hear the reality of it all.

It’s not just all rainbows and sunshines, it’s also real life. There are also struggles that you have to go through. 

So when you finally did this, you’re on the road, you’re in a new country, what has been a reality starter for you? ‘Cause it’s different, right? Was there anything that shocked you, surprised you during this journey?


Yeah. I think there are a lot of things that I was surprised by that sometimes pleasantly surprised and sometimes not so much. Certain people who are, for instance, writers, you can have a pretty steady gig as a digital nomad.

But how you generate leads, you could try to, for instance, start your own company or just find clients for your consulting business or whatever services that you can provide. Just learning about how to actually go by finding clients and finding the work opportunities for yourself. 

When I first started freelancing work, I still kind of had a corporate job. And then when I was traveling and freelancing before I joined Uber, I had savings and felt less pressure. But when I felt like I’m really committing to this, the uncertainty was scary, but I was very pleasantly surprised by how many opportunities you can come across for yourself. 

If you kind of just network and talk to a lot of people online and reach out to people – a lot of great tools for that now. Like, I met a lot of good people through this app called Lunchclub, have you heard of it?


No, tell us more.


Lunchclub has been for a while but, I think, during the pandemic it really took off. It’s remote. Networking site. It matches based on your interest and space you’re in, your previous work experience, and your LinkedIn profile, basically. 

They connect you with a random person somewhere and you just basically have lunch with them, connect with them for like an hour, and just chat. And that kind of intimate networking in a remote environment is obviously very appealing during the pandemic.

I met a lot of people through that, 2 or 3 people, every single person basically has done something for me and I’ve done something for them. In the current gig that I have as an independent remote business consultant, I was able to establish a more steady leap through somebody I met who introduced me to a remote-based consulting firm. 


That is incredible. I love how you’re able to still network even though you’re doing it remotely. And I think, honestly, it’s so much easier when you do it that way and you don’t have to leave your house, especially if you are a digital nomad, that’s such a great tool to be able to use.

So thank you so much for that tip, Jen, that’s awesome. 

So when you finally left Uber and you decided you needed to do something else because obviously, you have a life, you need to support yourself, how did you figure out what to do after that? Because I know you didn’t want to go back to corporate and you decided to do something on your own, what was that process like for you?


I think after I got laid off I probably slept for like 3 days just because I was mentally exhausted. And then, afterward, I kind of had to take a couple of weeks to really think. 

I think, in my heart, I knew that I wanted to expand the freelance work that I’ve been doing here and there but also have to kind of really ask myself like, “Are you ready for this?” I knew that, in my heart, I wanted to launch a startup. 

So there is this travel product idea that I’ve had for years and I just kind of, when I got laid off, thought that this is probably the best time to work on that. I have to push and I felt like things that were happening in my life were pushing me in that direction. 

But to make that jump, to finally decide to commit, that took a while and a lot of thinking, talking to my friends, talking to my family, even asking strangers on different forums. 

And what really kind of got me was, again, like asking people who’ve done this, launched their own startup and just kind of being like, “How do I get started? What do I do? I can’t just start building a product so what do I do now?” And understanding and just kind of like trying it out. 

So for instance as a start, they’re like, “Why don’t you just start with sketching out what you want to create?” So I learned a great tool called Figma, super intuitive. There’s a tool called Sketch that’s used by UX designers, the professionals.

Figma, anybody can quickly learn and pick up on it and I just started basically creating wireframes with what I wanted to build. It got interesting and then I started socializing that with different people and then found people who were interested in that idea who pointed me in different directions. 

So it was a very step-by-step kind of journey that’s like dipping my toes in and see. And after like a few different steps, taking a couple of different actions, I actually realized I can do this, anybody can do this. 

It’s just kind of that hurdle of like you don’t really know what’s on the other side was the initial blocker. 


That is incredible and again so many great resources out there. And also if you just put yourself out there and ask questions, it’s always going to happen. More people will just give you so many great tips on how to do it and do it well because they have been there and done that already.

So when you have started it, you finally took those steps, how did you land your first client, Jen?


I think, for the travel app, it’s more of a free tool. So there is no sales and lead generation but I can speak to kind of my remote business consulting gig. I used Upwork as a start obviously and took on projects that I thought would look relevant to the type of consulting work that I could do and obviously, initially, charge a very low fee so that I can kind of get my foot in the door.

And kind of work with clients and build relationships and got a couple of referrals. And, again, most of the gigs that I got, I got through networking.

For instance, I was looking for my first kind of really big consulting project that I did after Uber. I was looking to hire a designer for my travel app, and then I spoke to the design agency and we had a couple of calls. 

And he just liked me in the way I kind of talked about product and how different research I’ve done and clearly indicated that I’ve invested a lot of time and effort into understanding what I want to build and thus, kind of show different skills related to app design and go-to-market strategy.

And he actually reached out to me and said, “Actually, we want to hire you if you’re interested because we’re working on building our design agency and build a new platform. Would you be interested in that?” 

And that’s how I landed my first gig.


That’s incredible.


Yeah. And then afterward I just kind of network through Lunchclub and got somebody who had a consulting gig through a remote consulting firm called Fidelman & Co. And they only work with contractors and freelancers and they do the lead generation for you. 

I don’t think that’s very common but I think that business model will soon become more popular even after the pandemic.

I wish I could give an answer that’s like if you do this, this, this – it’s guaranteed. It’s not really like that. You just really have to talk to people and have confidence in yourself that you know what you’re talking about. 

Like, you had enough experience, you’ve done your research, done your homework, you studied, and you’re able to talk about a subject intelligently. And that is something that they pick up on immediately. 

So once you do that out there, if they don’t have opportunities to hire you right away, they will find people in their networks to introduce you to. And that process is guaranteed to produce some results. 

There’s no formula that’s like if you do X, you can get Y. I think that if you actually invest the time into speaking with different people. Just talking about yourself, talking about the subject, and just really add value to that person, you will be able to find opportunities.


Yeah. And also when you do that you are authority building, right? Like you said, if you know what you’re talking about, people will see that because you’re not BSing anyone. You are skilled at it and most likely if they know someone they will recommend you.

So that is such a great way to build up your network to really prove your authority and to get people to notice you that way. 

And it seems like you have been building up your clientele. From the beginning with networking, for someone who is intimidated by that because that is a word that a lot of people are scared of, what would you say would be the best thing to do if you are not familiar or you’re just not used to putting yourself out there yet?


One way to establish authority without having to talk to a bunch of people, ‘cause I know that’s difficult for some people especially if You’re not so extroverted, what you can do is kind of write a blog post about a topic.

You can send it to other people, try to kind of promote that content. A lot of startup founders that I spoke to, that I have gotten to know over the past couple of years, startups than big companies hire more people because they’re looking for information.

They’re like, “Well, how do I do this? How do I do PR? How do I manage my social media accounts effectively?” 

And if they come across your content and they can tell that what you’ve posted isn’t written by some hired writer that a website kind of created in order to generate because of their SEO strategy and your article goes into details about your strategy or tactics and whatnot, they will hire you.

That happens more often than you think.

So there are ways to establish authority and bring the traffic to you directly rather than going about the way I did which is just kind of going into the void and go networking just to see how opportunities will present themselves. You can kind of do it that way.


Yeah. I love that. There’s a lot of different strategies to do it and there’s just no one way to create those types of networks and attract clients. That is awesome.

So, Jen, when you left your day job and before setting off to being location independent, how are you able to save and budget your money to make sure that it lasts? 


That’s a great question. First, you kind of have to look at the project. For instance, ’cause I’m a remote business consultant, projects that you have in the pipeline and then say, “Well, how much can I earn?” 

But the thing is when you’re leading your own project, one of the biggest risks to your revenue stream is like somebody potentially canceling a contract whereas, in a full-time job, there’s more certainty there that you’re guaranteed a certain amount of income each month. 

So you need to make sure that, in your contract and when you’re budgeting with a client, you set your terms correctly, clearly, and align on exactly what your rates are,  the number of hours should be if you want to have set hours or make it fixed. 

And then have cancellation terms so that you are getting paid. For instance, two weeks cancellation fee so you will have enough time when somebody cancels abruptly. Like you will have enough time to find new projects. That’s kind of how I looked at the top line in terms of making sure that I have enough money coming in.

And then in terms of actual spending, it was more of just kind of looking for deals, I think – deal hunting. 

And spreading out the expenses, the challenges that I had was not only am I supporting myself, my travels, and other activities in my personal life. Because I started a company, I have to spend my own money in terms of hiring a designer, content creator. A lot of different things in terms of costs that are required to build a company.

I did a lot of research ahead of time in terms of how much things would cost. Again, like going on talking to people, asking people doing research. For instance, I knew a lawyer fee for a new startup. It was always kind of a struggle for a lot of people. So I interviewed a couple of different lawyers just to get a sense of what the rates are. 

I went on sites like Startup School, it’s a Y combinator website, a free education platform for aspiring founders, you can join that and then take some courses. There is a form where you can just kind of ask questions to different people so you can get a sense of what the cost would be. 

So that’s how I budgeted things, by understanding cost ahead of time. 


So what made you decide, Jen, to stay in Australia after all of this? Once you left Uber you could have gone to other places. What was it about Australia that made you decide that this was going to be your home base instead of going to other destinations?


Australias is so big. I’ve been here two years and I’ve seen more than some of my friends in Sydney and they’ve been here and their whole life. And I still feel like I covered maybe 10%.

So there’s so much to explore. In Sydney alone, there are so many beaches – it’s crazy. I don’t think I can even make it to all of them. They have this thing called coastal walk which is one of my favorite activities. You just walk along the coast and just go to look at the bunch of different beaches and stuff. That alone will take you months. 

So I think that just wanting to explore, be more immersed in the culture and visit different areas rather than just kind of roaming known areas like Sydney and Melbourne – things like that. Just finding different places to visit, different activities, meeting locals, and learning more about it. 

I mean, when I went to this one city called Perth, I was staying at Fremantle right next to Perth and I actually looked at a couple of different tour sites, tour activity sites like TripAdvisor, and went through all of the pages. I went through every single thing in that area that I could possibly do.

And I got on this wine cruise thing. It’s basically like a commuter cruise boat ride. You buy tickets and they give you wine and you do a wine tasting. That was interesting so I tried it out.


That’s awesome. 


Yeah. It was awesome.

I was talking to the people working and then they were like, “Oh, you should go to Fremantle prison.” I was like, “What is that?” They were like, “They do Fremantle prison tours. You can  do a nighttime tour if you want to.” 

There’s an option where you can like get on the boat or something and then go underneath the tunnels. That’s like the path the prisoners took to escape and I was like, “Why is it that I haven’t seen this on any website? How is that even possible?” And they don’t promote it there. If you ask anyone that’s a place the locals would recommend.

When I kind of start feeling that I just felt like Australia has so much to offer. It’s just so different that I’m not worried about, “Oh, am I staying in one place and just kind of the same thing. Like, I can do something different on every trip, every day.

And, also, Australia did a really good job in terms of managing the pandemic so I decided to hide out here until things calm down in the States. 


That’s awesome. It’s such a beautiful and huge country that, you’re right, there’s just so much to explore. And I love that you’re doing slow travel, you have a home base. It’s much more sustainable that way at least in my opinion when you do it that way.

But to each their own. There are some digital nomads who just love to go from place to place. There’s nothing wrong with that as long as you have the energy. But I’m with you on having the home base and doing slow travel. 

I think as I get older too I’m just like, “I’m too tired for that and I have too many things to do to pack and unpack every month or so.” So yeah, I hear you on that. 

So, Jen, when you are traveling and now that you have moved abroad, what type of international insurance have you used or you use?


I haven’t really used travel insurance in particular but there was one that I came across a while ago which is called World Nomads. And it’s like a travel insurance that you can get and it kind of gives you protection coverage in multiple countries and different activities.

So if you’re a skier and you want to go on intense ski trips and hit a bunch of different cities. Like, crazy mountains in Switzerland or something, it kind of covers potential accidents specific to the activities that you’d be doing.

But I personally haven’t had a travel insurance other than my health insurance. 


Yeah. I definitely hear you on that. I hear that from digital nomads.

It’s hard to find a travel insurance that has really comprehensive plans. And as a remote worker myself, like you, it can be a headache to find the different requirements that it really requires when it comes to health insurance, especially in other countries. 

That’s why I’m really glad that I found Integra Global and their super, super comprehensive plans. They don’t ask their members to build one because how do we know what we’ll need, right? Especially when we’re traveling abroad.

Their insurance covers everything and all of these different things are built in it. So if you want to know more make sure you check out and see how they can give you the coverage that you’ll need and maybe some you never knew you would.

And I do have to say during the pandemic, obviously, it’s still happening now, but when it was just brand new and people we’re stuck overseas, Integra actually had coverage plans for that and there were some insurance companies that actually didn’t have that.

So they’re really incredible and they’re super comprehensive. So make sure you go to Awesome. 

So now, Jen, I have a few fun questions for you, very quick, and you have to answer in one sentence for each. Sounds good?


Yeah. I’m ready.


So what is the worst food that you have ever eaten and why? 


Oh, cow balls.  


Oh my God. Okay. Tell us more worried. I’m like, “One sentence”, but now I’m like, “Cow balls..” Tell us more, Jen, where did you taste this delicacy and how did it taste? 


I had it once in New York which was a traumatizing experience. They had like pesto sauce so it was slightly better and I had it again in Australia and there’s no way I’m ever going to like it. Just the texture. You can’t get over the texture.


I love that you did it twice though. You’re like, “Maybe it was the pesto sauce that time. This time, maybe they’ll prepare it better. 


Everyone deserves a second chance.


Yeah. I like a girl like you, Jen, you didn’t like it the first time, give him a second chance. You never know, maybe it was the chef – you don’t know.


Yeah. But now I can cross that.



What has been the best money you’ve ever spent while abroad and why? 


I think that every time I’m somewhere abroad I always find a local telecom store like Verizon and I buy a SIM card, it’s the first thing that I do and it’s super cheap and they always have a good plan for tourists. So money well spent because I hate not having internet, especially in a foreign country.


Yeah, that’s so true. I love that and just in case of emergencies that is always good to have. 

Describe what your ideal day would look like. 


I think I am already kind of living that right now. I go to the beach in the morning and kind of walk around, take naps during the day ’cause I work the US, UK hours so that’s my night time. And yeah, just how I’m living today. 

I work, I connect with the people in my team, we have meetings, we talk about what needs to get done today. Work through the day and then repeat the next day. 


That Is amazing. I love hearing that.

Now, if you could have a superpower, what would it be and why? 


Teleportation ’cause I’m always late.


Especially if you’re also an avid traveler that would be so much easier. Especially now with airplanes and stuff. 

What’s the one thing you wish you did sooner? 


Starting my own company. 


Love that. Awesome. I love all of your answers, Jen, from the cow balls to, oh my goodness, living there, the day that you actually love. Like, your ideal day is the one that you’re living now is incredible. 

Speaking of that, let’s fast-forward to around 30 to 40 years from now and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for? 


Yeah. When I thought about starting on my own, not just being a digital nomad, but starting my own company, the question that you have to ask yourself is like what you’ve just asked me, “What do you want to live by? What do you want to be known for?

I kind of had to do a little bit of soul searching but my real mission is to build something that brings people together and grows from shared experiences. I’m a connector, this is my personality. You can tell I like networking, I like meeting new people, my friends are all over the world. 

That’s why I kind of built my company, Levantr, which is a kind of trip collaboration tool, right? So that’s just one tool. That’s just one way that I’m getting started in terms of achieving that but really kind of building my own site. Hopefully, that takes off and an additional kind of products, platforms, or communities that I want to create through that. 

Hopefully, bring people together, inspire, and encourage people to travel further, explore the unknown and also have a charitable. Allow young adults to travel somewhere completely new, somewhere completely different.

And I really do think that being exposed to different cultures and different types of people and environments really reduce your prejudice, makes you more empathetic. 

And I want to kind of make sure that that experience is not just something that only a handful will experience but that’s something that becomes more and more universal regardless of your income status or your economic standing in society.


I love that legacy that you want to leave. 

Thank you so much for being here today, Jen. If our listeners want to know more about you, where can they find you? 


I can give you a link to our Instagram. You can DM me anytime. I’m also happy to provide my email address: You can email me anytime.


Awesome. Thank you so much, Jen, we really appreciate you for being here and for sharing your incredible story with us. 


Thank you.

Listen to Jen’s extended interview where she shares how to conduct customer interviews to provide the best products and services for your audience.

What you’ll find:

In this episode, Jen will guide you through the process of conducting effective customer interviews for product and service building.

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Show Credits:

Audio Engineer: Ben Smith

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