Kat Shortsleeve, combining her expertise in wealth management and education from Columbia Business School with a deep-seated passion for travel, narrates how she funded her journeys to over 40 countries through various side jobs during her college days. She talks about her experiences as a New York Times Campus Ambassador and Spanish tutor, highlighting how these roles not only fueled her travel aspirations but also shaped her professional path in wealth management and real estate private equity. This episode offers a captivating look into leveraging creative job opportunities for achieving travel and career goals.
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Kat Shortsleeve, combining her expertise in wealth management and education from Columbia Business School with a deep-seated passion for travel, narrates how she funded her journeys to over 40 countries through various side jobs during her college days. She talks about her experiences as a New York Times Campus Ambassador and Spanish tutor, highlighting how these roles not only fueled her travel aspirations but also shaped her professional path in wealth management and real estate private equity. This episode offers a captivating look into leveraging creative job opportunities for achieving travel and career goals.
Instagram @katshortsleeve
Tik Tok @katshortsleeve
Youtube Shortsleeve Travel with Kat Shortsleeve
Welcome back to the short sleeve travel podcast. I'm your host cat short sleeve. I have worked in wealth management for five years. I recently completed my MBA at Columbia business school and all at the same time I have traveled to over 40 countries. I have a major obsession with personal finance and travel and how to use money because I realized if you can manage your money, that will provide you with power and personal freedom. I always try to make every trip feel first class without the first class price tag, and through some inspiring stories, curated guides, and insightful investing tips, short sleeve travel will be your compass, pointing you to experiences that are elevated yet attainable. So are you ready to redefine luxury travel on your terms? Dive in with me and I'll help you fill in your life with as much travel as you desire. I am so excited about this episode because it has been Requested many times. This is the topic. I get probably some of the most questions about and that is side jobs What side jobs have I had to help me create some income to fund my travel addiction? So I will dive into all of the different side jobs. I've had just in college of which there are about six I'll explain how I got each of these jobs how much it paid and what I had to do And then, at the end, I'll ultimately explain how all of these jobs helped me to land my dream career at a wealth management firm and later at another real estate private equity firm. All of the skills and all of the experience that I built up during these different internships when I was in college helped me to build an incredible resume, which wasn't even the goal. The goal was just to create as much side money as possible to fund my travel. But I will get there. So, first things first, when I was in college, I was at Georgetown University, and I traveled to 20 countries during that time. This was all self funded through these various side jobs that I had. My junior year, I really wanted to go to Asia, but it was going to cost about 3, 000, and my parents were definitely not funding this. I needed to figure out a way to make money on my own to fund this, and so I needed to get creative. Up until that point, I had had some side jobs, but I knew I really needed to kind of hit the ground running and make some more money. Because the money I had previously been making helped me just to live day to day, week to week in Georgetown. It was my spending money. And now I needed to make some more money so that I could actually save that and go on this incredible trip. The flight was somewhere around a thousand dollars. And for three weeks we had budgeted and found the right hotels and accommodation and transportation, everything where it was only going to cost 2, 000. And on this trip, we went to so many places. I think it's incredible that we did this on 3, 000, but you can even do it on less money. We went to Hong Kong, Cambodia, Vietnam. Thailand, we had layovers in Singapore, not Singapore, in Seoul, South Korea, which was so cool. I am still obsessed with that airport. I actually am really excited because I'll be flying through that airport again in two weeks and hopefully someday I can actually get out of the airport in South Korea and go explore. We were able to keep this trip so cheap because we had four girls and so we shared one hotel room, we shared one taxi. It's the perfect number because you get two queen beds, you fill up an entire taxi, one in the front seat, three in the back. And you're able to split everything four ways, which is the maximum way really to split things. We got really comfortable with each other because this was a three week trip, but it was amazing. And we saw and did so much. If you have an opportunity to take an extra week or two off around spring break, when you're in college and do something like this, I highly recommend doing it on my podcast or on my blog. I have a. Detailed itinerary as to what we did, places we went. And if you have any questions, please feel free to reach out to me. Happy to help you plan a trip to Asia. It really changed the way I was thinking about travel. And this one trip in particular grew my bucket list tenfold. when you're traveling, you learn about all these other places that you eventually want to go to. And we were spending all of our money on experiences. Going island hopping when we were in Thailand and going to temples, temple hopping when we were in Cambodia. We went kayaking, we got on different Vespas and rode through the cities, or the streets in Hanoi, Vietnam. I have a friend who I grew up with in the summertime who actually lives in Hong Kong during the year, so we went and had dinner with her and her family. It was an incredible trip. But anyways, all of that was only possible because I had these side jobs to help make some money. So I'm spending money and some travel money. I'll start at the most basic and I'll start with what I actually began doing. And then later you'll see when I was in college, I got some more high paying internships and job opportunities because I had had previous work experience with these more basic things. So the two most basic things that I did and really require absolutely zero experience whatsoever. First of all is I babysat. I think some people forget that they can still do this when they're in college. I lived in Georgetown, and so there's a whole neighborhood of people, young families, who are looking for babysitters. I babysat for a few different families when I was there, but I had some referrals come in through friends who had graduated, and they were looking for people to take over their babysitting gig. And if you can find something that's more consistent, that's obviously the best. I know some people who were nannies while in college and so they're babysitting three times a week and actually managing their class schedule around babysitting because it's going to be tax free money. It's all under the table. And something incredible about babysitting is it gives you a lot of time to do homework, so it's kind of perfect for high school kids and college kids. You can get a lot of homework done or readings done while the kids are going to bed. Or while they're playing. And you don't need any experience, of course, to do this. There are so many platforms nowadays where you can sign up, create a profile for yourself, and find out who in the area needs to find a sitter. But you can also just look at local newspapers to find out who might need a sitter. You can look at Facebook groups online. Do your research and find out which Facebook groups are going to be the best in your area. But that's an easy thing to just do on the side, and you can also be productive with the other things in your life at the same time. So that is number one. The second thing that you are able to do really easily, and this is what I did, is I tutored Spanish. Similar to babysitting, this made me a couple hundred dollars a week, and I would just tutor classmates, and when I had experience tutoring classmates, so people just in my Spanish class who needed extra help because that was one subject that I was actually good at, the school realized I was a good tutor, and so I went to one of the tutoring departments and actually got a job there. And unfortunately, I was taxed at that point, so if you can try to find some ways to make connections with people who need tutoring without having to go through official programs, you'll make the most amount of money that way, but either way, I ended up going through the school, and what I didn't realize is I then had someone who could write a great recommendation for me, so I got a letter of recommendation from the head of the tutoring department, for one of my later job opportunities. It was really great to be tutoring Spanish to people just in my class because it helped me to study anyways for the upcoming exams and I was able to make deeper connections with people in my class. I ended up doing really well in my Spanish class I think partially, of course, because I was I was helping other people study, so it made me study even more. But also the professor of the class found out that I was tutoring other people, and she really liked that. She liked that I was helping other people just excel in the subject. So my participation grade was pretty high. Even if you're not in college, or you live close to a college, so if you're in any major city, you are close to a college, you can still find people to tutor that way. There are jobs where you are able to tutor kids that are in second grade. You basically help teach them how to read and read books with them. In my opinion, that kind of tows the line between tutoring and babysitting, but that's always an option. So after I had these first two experiences of babysitting and tutoring, I then found my next job opportunity, which was one of my more real job opportunities, and this was at the alumni house on campus. I had found out from someone who was living in my dorm about these job opportunities at the alumni house where you could do different things, but the most attractive and interesting to me was kind of a more salesy role, and essentially the job was to call alumni and ask them for donations to the university. It's a bit of an easy sell because they went to the university, you go to the university and you can kind of just tell them about new things happening on campus, where the money is going to be invested and just ask if they'd like to make some sort of contribution. And it was nice because the year was 2018 and we were only asking for 20 and 18 cents. So it wasn't a huge sell and some people would just say, Hey, call me later. Hey, not interested. Or yeah, I'll give you 20 bucks or a hundred bucks. The conversations were easy, but it was a good introduction to sales and I didn't realize this at the time, but it was giving me great experience in selling over the phone. So interesting, actually, at first when I applied, you have to have three rounds of interviews, and I got through the first two rounds, they're both in person on campus at the Alumni House. And in the third round, I went in for my interview, I was excited about it, I was eager to have this job at that point, because it was paying something like 25 an hour. And after my third interview, I went back to my apartment, thought that I had nailed it, knocked it out of the park, and I emailed asking for an update a week later, two weeks later, and finally two and a half weeks later, I found out that I was rejected, I did not get the job, and I was pretty upset, and I was also so bold at the time that I decided to email them back and say, you know, I'm really disappointed, I thought that the interview had gone really well, and this is ridiculous, but then they actually emailed me back and ended up saying, you know what, we re looked at the notes for your interview, and you actually Can't have a job here. We'd like to offer you the position. So simply rejecting my rejection letter helped me to get a job there. So many things that I have done, I just kind of push and push and push, so always ask for feedback and explain why you think you're a good candidate for a role if you are rejected. That's what I learned from that experience. Another great thing about this job is because you're on the phone calling different people, a lot of times it would ring and ring and ring and it would take time for the system to boot up to call people. And so you can also do homework while you're there. The easiest thing for me to do was I just had a stack of flashcards. I remember from one of my history classes and I would sit there and just flip through the flashcards while the phone was ringing. And sometimes it would be five minutes in between calls. And so you can get through quite a bit. So I liked being able to be productive while making money at the same time. And people there really become close friends with each other. You spend a lot of time in this one room, everyone's making calls, and they have happy hours and socials and things, so it's kind of a good group to be a part of. If you are an undergrad, I recommend checking out the Alumni House on campus. It's kind of overlooked in my opinion. So now with that experience, I had enjoyed it, but I became pretty tired of making phone calls all the time, and you had to be on for certain shifts, and I just got tired of the job. It was great, but I then realized I wanted a new opportunity and some new experience because I had done that for quite a while. And so this next job opportunity was pretty cool. I was very interested in entrepreneurship and I had been studying it at Georgetown. I actually did a minor in entrepreneurship through our business school. And I just needed another way to make some money. So I did some research and I created a list of entrepreneurs who had gone to Georgetown and I wrote notes about each of their companies. I found the ones that were most interesting to me and I cold emailed about 10 of them. I did tons of research in advance, and then I would email them with specific insights as to how I thought their company could do better in the future. A place where I thought that I could help them out. And something from an outsider's perspective that I thought that they could kind of lean into or weren't leaning into. So basically just emailing them and saying, Hey, I am so interested in your company, I went to the same, I go to the same university that you went to as an undergrad. I noticed looking at your website and your social media and your newsletter that, Blah, blah, blah. You can be improving in this way. I think it'd be a really smart idea if you did this. And then I said to them, you know, I am looking for work and I would love to intern with your company and work on this project that I've proposed. So essentially I was creating a role at a company that did not exist, providing them with some sort of value by saying, I think you should be trending in this direction, or I think you're overlooking this. Providing them with some sort of value and then offering to work with them. I offered off the bat to intern for free and most of the time, companies aren't really able to just let you work there for free. They need to be paying you to some degree. And so, 80 percent of the companies, these entrepreneurs that I had reached out to, got back to me and were interested in working with me. I sifted through and had lots of conversations with these entrepreneurs to find out what was going to be a better long term fit for me, and I ended up working for two entrepreneurs, one of which was so interesting. So he had started a glass bottle company, and my role was essentially to be a campus ambassador for this company, and create a bit of brand awareness on campus at Georgetown for this founder who went there. And then I also was setting up brand ambassador programs across other universities in D. C. And then I expanded to New York City as well as to Boston. And then I had left the company after about a year of working with them, but I began to expand it out to L. A. and found other people who were expanding it from there. So we created this entire campus ambassador program. It was pretty cool because I had so many glass bottles sent to me by the entrepreneur and the founder. And I just had stacks and stacks of these pretty neat glass bottles to hand out to friends. I brought them to tailgates, created a bit of awareness about the brand, and people seemed to really like them. The founder kept shipping me more and more of these glass bottles. I did a couple pop ups on campus. I did some different giveaways. It was very cool. And he ended up paying me a stipend, a stipend monthly to help him out. With that experience, I then landed my highest paying job as an undergrad, and this was working for the New York Times. I was making actually 3, 000 a month as a campus ambassador for the New York Times. This was such good money, especially for the amount of time that I had to dedicate to the role. Of course, it was entirely remote, it was entirely self directed. This is a role that still exists today, and as an ambassador, basically you are responsible for promoting and raising awareness for the New York Times on campus. You then actually help students to sign up for a New York Times subscription, which is incredibly easy, and you help them download the app. You'll do things like postering, tabling, presentations, networking. If you are organized, outgoing, comfortable talking and presenting to people. You can apply to this program and it's very easy to get accepted. A bunch of companies actually have similar campus ambassador programs. So you should look into whatever it is that you're interested in and see if they have some sort of campus ambassador program. For example, I also did a little bit of an internship with Love Your Melon. They are a hack company. Raising awareness about different pediatric cancers. And I worked with them and raised awareness for them on campus, but that was not paid. Again, great experience, but unpaid. But, with the New York Times, all I really had to do in order to meet my quotas and continue working there and making 3, 000 a month was to make sure 15 people per semester, I believe, signed up for the New York Times. It was such an easy sell, again, because it was 1 per month and who doesn't want access to great news? If you're interested in this role, they have it on their, on the New York Times website right now and you can find all the accurate, up to date information about the program, the roles, responsibilities, benefits, everything. And you can actually just contact the New York Times directly on their website as well as through Instagram and they'll definitely respond to you. Because they're looking for people all the time. There's high turnover, turnover in that role. Another little micro job that I had, I don't remember it making much money whatsoever. But in, I was in D. C. and a lot of people do this, so I wanted to kind of hop on the bandwagon and do, do it as well. I didn't love it, definitely don't want to work in politics, but I was in Washington, D. C. So I decided to intern on a congressman's campaign. Was kind of doing anything and everything they asked you to. I had to travel far for that role, so given the really nice roles that I had had previously, that was not my favorite thing I've ever done. But all of these different, Internships and all this experience added up for me, and I was on a flight going from D. C. to Boston one Christmas or I think it was actually later, I think it was in the springtime because I was looking for a summertime internship and I was speaking with the person next to me on the flight about all of these internships I've had, the experience I have, what I've done, and how I'm studying psychology and entrepreneurship, looking to find some Company to work for over the summertime. I was not making much progress and didn't have much luck with finding a great internship that I was excited about. And ultimately, long story short, this person that I was sitting next to ended up connecting me with a friend who I met up with in Boston two days later, had a conversation with this person. They were working on an entrepreneur center and they weren't hiring for their company specifically, but this person was such a good connection because they listened to my story, listened to what I was interested in. And they had great connections in Boston and entrepreneurship, and they connect me with this incredible nonprofit company who I ended up getting a long term internship with. So I interned with them over the summer. It was fully remote, but then what was incredible is they needed my help and they were so small that I ended up working with them for three years after the fact. And that was such great passive income for me to make while being remote, and so I was able to add on these other. Internships and opportunities and babysitting and tutoring, because I could do it remotely and save tons of time. I think those are the best types of jobs to have while you're in college, just gain experience, not have to sink all your time into it. And then better experience probably once you're out of college is more in person or you're building skills, things like that. But I worked as an advisor and a grant writer for this non profit. I helped them with anything and everything. It was founded by two women who are a bit older, they both have kids, and they felt like they needed a little bit more of a pulse on young people. Because this company essentially works with young people, helping them to rehabilitate and enter into school systems after they've had some major life event happen for them. So we built this entire program called an Alternative Peer Group, APG, where kids go and get counseling and get rehabilitation. And it's an added friend group outside of your friend group at school. It's kind of a, a middle, middle of the road stop and ground between some sort of official rehabilitation center and re entering into normal life. So it helps you transition between the two. Um, when you're really young, it's actually for kids under the age of 18. The company is focused in South Massachusetts, Southeast Massachusetts. And so being from Boston, it was nice because every time I came back home, I would go visit the founders, spend some time with them, actually be in person. We would set a plan of action for the next three or four months as to what we were going to work on, and then it was very independent and self directed, which again, I absolutely love. So all of this experience added up and essentially ended up helping me to land a job in wealth management going into my senior year in college. I was working on the business development team at Cambridge Associates and I absolutely loved that. Because I had experience in sales and with managing different people. As well as working for entrepreneurs who are managing different budgets. With all this experience I had so much that I was able to speak to during the interview process at this wealth management firm and then having that experience in the wealth management firm of course led me to be in a great position once I had my MBA at Columbia Business School to be up for a position at a real estate private equity firm. I am so grateful for all of these experiences that I had as an undergrad. And while at the time I was really only just trying to make money and travel as much as possible, it helped set me up for the future really nicely. And I'm grateful I tried so many different types of companies. That helped me to figure out what type of company I'd want to work for later. You know, I realized that I didn't want to work for an entrepreneur and at a small startup because I'd worked with entrepreneurs. I realized that I didn't want to work for something that had really small budgets or was a cost center like the Alumni House. And I did like working for the New York Times. It was a larger corporation. Much more of a foundation and stability. And it also, you know, I realized I didn't want to work in politics on a congressman's campaign ever again. I had to make a lot of sacrifices and not be a part of some sports teams and some clubs that I did want to be a part of at school. And there are endless possibilities as an undergrad and in the real world, so capitalizing on what is going to help set you up the best for the long term but also grant you the most immediate happiness, that at least is how I decided to think about it and I'm so grateful for all of those experiences. And I never think you are In too much of a stable position to never want some sort of side gig, whether it is for financial gain or just exposure, experience, or just to learn something new. Thank you so much for tuning in and listening to all of my stories about side jobs and hustles to make money while I was an undergrad for travel. Since graduating from my undergrad, I've had a few other side hustles and side companies that I started. And I had a few internships at Columbia Business School to make some money as well that I would love to speak to in a later episode. But the next episode I'm going to touch a little bit about Soho Houses, the ones that I have been to, which I have been to quite a few of them at this point. And I will give you a bit of a financial breakdown, in my opinion, if it makes sense financially to belong to Soho House. And also debunk some of the myths about the membership. And just give you a very fulsome picture of the Soho House membership and my thoughts. So tune in for that next episode. I am so excited for it. I have lots of insights to share. But thank you all for listening and thank you so much for catching up with me. I really appreciate all of you who do come listen. If you enjoyed this, I would so appreciate it if you could leave a review as well as download the episodes and subscribe because it makes a huge impact for me. And would really love to grow this platform to help more people. Who are interested in the intersection of travel and money. Okay. Next time we will chat all about Soho houses until then safe travels and cheers.