The last 10 years. 30 countries. Dropout to ESL teacher to software engineer making $300k+ (w/ paystubs)

Ok. Let’s get the money stuff out of the way.

Here’s my YTD pay from my W2 Software Engineering job through June 13th, 2024.

$142,614.69.

I’ve paid $43,587.18 in taxes already, which is nearly the salary of my first ever software engineering job 😢.

We’re almost half way through the year so you can simply double that number above, add a bit, and see that I’m just above $300k from my W-2.

I sold a SaaS to a lawn care company last year for $36,000 USD. The client made a $2,000 deposit and paid the remainder over 10 months. You can see the $3,400 payments below.

(I’ll tell you exactly how I sold this SaaS later on in this newsletter)

The deal was structured like this:

• $2,400/month to build the app

• $1,200/month, 10 hours at $120/hr, for maintenance on the app once it’s built

Again, more on why it was structured like this later on.

After those 10 months, the client wanted to renew the maintenance part of the contract for another year. We agreed on $1,000/month. We’re coming up on month 3 of that right now. You can see those payments below.

I made $28,626 in 2023 from my web development agency.

I wanted to get this out of the way because:

1) There’s simply nothing that I hate more on Twitter/X than someone posting screenshots with zero back story, or context, other than, “you can do this too if you buy my course” and then it’s just a series on how to sell courses to people who… wait for it, want to sell courses. 2nd place is the coach who coaches coaches who help other people become coaches who coach coaches. Don’t get me started.

2) Some of you probably clicked this just because of the “w/ paystubs” in the title 😉

So, how did I get here? Here we go…

My life changed forever my junior year of college in my Business Ethics class.

The professor was famous at my University. People either loved him or hated him… and when I say loved him or hated him, I mean it. He was controversial, to say the least. My grandma still refers to him as “that one professor.” And to this day, anyone I’ve ever met that went to my school knows him, or of him, and has a story about him.

He made me question things for the first time. He mocked everything you held near and dear to your heart but yet he did it in a humorous way so that you never felt insulted but inquisitive instead. “Hmm… that is kind of odd/funny when you put it like that.”

He had a top 100 books list and I read 80-90% of it. All the classics. You name it, it’s on there. I started skipping my other classes just to finish reading them. I want to say that I was completely absorbed in “something” for the first time but if you asked me what exactly that “something” was, I’m not sure I could put my finger on it. Philosophy? The meaning of life and/or the best way to live? Something like that.

I was 21. More of a kid than an adult still, like most college kids in the US of A, completely naive to the world that awaits on the other side of a few more years. I was just 1 year from that “other side.” And for the first time ever, I was truly forced to think about what I wanted to do with my life. And to be honest, I had no fucking clue. I had less than a clue. Scary.

I was 3 years into a business degree that I’d only chosen because that’s what all my friends chose. I’d accumulated ~$45k in student loan debt (thankfully I went to state school, this could’ve been much worse) and now I was second guessing it all… not just my degree but everything I thought about everything.

Business administration? What does that even mean? Administering a business? Is that something you can even learn in school? I’m 21. No one is gong to hire me to do any kind of “administering.”

I’m going to be an intern making $32k organizing manila folders in some cubicle in Dallas or Chicago. Forget that. I wanted to be a teacher instead. Yeah, I’d probably still be making $32k, but I didn’t care about the money. My professor had changed the trajectory of my life forever and I wanted to help other young kids do the same.

But! But, but, but, but… I’d also started learning to code on the side.

Business. Teaching. Coding. Business. Teaching. Coding. What to do. What to do.

This was literally me.

We’re towards the end of the school year, March/April of 2013. My friends and I needed to find a place to live for Senior year. We had a few leads from Craigslist, word of mouth, and from driving around in the evenings looking for “For Rent” signs in front yards.

One of those nights, I thought “this should be an app.”

I’d never written a line of code before. I was a Business major! I didn’t even really know what “code” was… something nerds in San Francisco did.

Like I said, I was skipping my business classes to read my professor’s top 100 books. I stopped reading those books and started (trying) to learn how to code instead.

Apple used Objective-C at the time (Swift came around the next year in 2014). I had absolutely no idea what I was doing… I didn’t know where to start, couldn’t tell forwards from backwards, but I suppose that’s how we all start anything, right?

There was simply too much to learn and not enough time.

As with any idea you think is good, the sense of “I need to do this right now, ASAP, or else someone else will” can be overwhelming, whether it’s true or not.

I ended up hiring someone to help. I had something like ~$3-5k in a ROTH IRA that my dad had help me set up after I got my first job at 16. I cashed out the whole thing to pay for it.

Looking back, this was way too cheap. I’m sure it was a bunch of Indian devs from Fiverrr. Who knows. The app worked. That’s all I cared about.

It was called “StudentShare.” Think AirBnB but for student rentals.

Again, this is 2013. AirBnB had been around a few years but there were still only ~400k listings total on the app. It wasn’t mainstream yet. I hadn’t ever used it before. No one I knew was using it.

We launched it to the App Store. I was stoked. I cold called every single listing on Craigslist in the area and asked the homeowners if they wanted to list their house on the app for free. Around ~70% agreed. It was free after all.

I went to the University registrar and they (surprisingly) gave me a list of every single landlord in the area! Talk about a jackpot. I called every single one.

The university had an event coming up for incoming freshman and asked if I wanted to pass out fliers at one of their booths. Of course I did!

Some buddies and I made fliers and we went around sticking them on every single dorm room door on the entire campus.

This feeling of building something, of being on the verge, is the best drug there is. There’s absolutely nothing like it… and I’m still chasing it to this very day.

The app got a little bit of traction but I had no idea how to monetize it. It failed the “toothbrush test” miserably (users use it 2x a day). The app only had housing, which students only look for 2-3x a year, max. I had plans to add a marketplace to resell furniture, used books, etc. Blah blah blah.

The school year ends.

The professor I mentioned before has a week long summer course on Entrepreneurship in Chicago every year. You already know I’m going.

Everyone is asked to come up with a business idea, make a pitch deck, and then pitch it to some prominent alumni that worked there in Chicago on the last day.

Long story short, I already had the app up and running. I used that. I won 1st place.

Funny side story, I was so bad at public speaking during my initial practice pitch that my professor actually made one of the other students pitch my idea for me in front of the alumni!

You’re probably thinking, “Wow, Isaac! 1st place! Was it like Shark Tank? Did you get a sponsorship? Some type of investment? That must’ve been your big break!”

No. None of that. It was nothing more than something to put on my resume and a little bit of networking. Sad.

So, what did you do next?

I dropped out!

You dropped out, Isaac? What? Why? Oh… yeah, I know why! It’s because that’s what all the tech legends do and you bootstrapped the app in your mom’s garage and then sold it for millions of dollars, right?

Absolutely not. I wish that’s what I would’ve done.

You ready for it?

I moved back to my hometown. I rented an apartment for $600/month and I got a job at Dick’s Sporting Goods making $9/hr.

Yeah… you weren’t expecting that, were you?

You see, that professor (and his book list) essentially destroyed my world view I’d had up to that point, and it was depressing. Everything felt like a lie. I was completely lost. The last thing I wanted to do was sit in a classroom and rack up more debt.

So, what did I do?

I sold baseball gloves and shin guards to kids and their parents instead.

I’d go to work, come home, smoke weed, read more books, and spiral further into the black hole I’d created for myself.

I did this for ~6 months.

This might be me trying to justify it, but I think this phase of my life was completely necessary in the grand scheme of things. I’m about 97% sure that I wouldn’t be who I am today if I hadn’t gone through that. Everyone needs some “dark” times to appreciate the “good” times.

Luckily, my Mom was always there to support me and she somehow, some way, got me to re-enroll the following semester.

I took 19 hours the first semester of my senior year and 21 the second. Straight A’s. I didn’t enjoy it, but I knew it was better to finish. A sunk cost, so to speak.

Way to go, Isaac! Then you got a job making a bunch of money and lived happily ever after, right?

No. C’mon now. That would’ve made way too much sense.

I moved to Sydney, Australia with my girlfriend at the time and did absolutely fuck all for 2 months.

Am I keeping you on your toes? Good. I hope so.

You see, I was still pretty depressed and mad at the world. I was the cliche naive libtard.

“Fuck capitalism! Fuck the system! Poor me, poor me!” was the sentiment of the writing I’d do on my latest model iPhone and/or MacBook.

Classic.

I made the mistake of thinking I could simply up and move somewhere else and instantly be happier… what they don’t tell you though is that no matter where you go, you’re still you!

An absolutely mind-melting concept. I know.

I’d sold my car for ~$10k before I left and bought a 1 way ticket. No plan. I just wanted to get away. Anywhere but here.

I’m sure my parents probably thought I’d spend all my money and be back within a few months… but I was gone for 5 years.

Like I said, I did pretty much nothing the first 2 months there in Sydney. I wandered around, drank coffee, rode my longboard, and wrote. I was one “hey, you got a dollar?” away from being a full-on bum.

I vividly remember going to the ATM one day and seeing my bank balance dwindling to dangerously low levels and thinking to myself, “I’ve got to do something.”

Yeah, no shit buddy! But what?

I found a staffing agency and they set me up with a “forklift spotting” job.

Yeah, riveting stuff. I know.

It was either that or holding traffic signs at construction sites. $19-$20/hour. Wages in Australia are ridiculous. I chose forklift spotting… and I quit after the 1st day.

Lol.

The next morning, I started googling ways to make money online/abroad. Teaching English as a second language (TESL/) appeared. I’d never heard of that before… but teaching! That was something my professor had got me interested in, maybe this was my start?

But wait a minute, Isaac. They speak English in Australia. How are you gonna teach English there? Yep. You’re spot on. I took a 120 hour online course and bought a 1 way ticket to Saigon, Vietnam!

Yes. You read that right. Saigon, Vietnam. Are your toes sore yet?

Why there? How the heck did you find a job there of all places?

C’mon. You should know better than that by now. I didn’t find a job there before I went. I’d simply read on a few different online forums that they paid ESL teachers well in Vietnam and it was the closest/cheapest flight from Australia.

I got off the plane and found a cheap hostel to stay at for a few days. I remember checking in, setting my bag down on the bed, opening the window that looked over onto an extremely busy street full of scooters and thinking, “what in the fuck am I doing?”

I asked the front desk if they knew of any cheap apartments nearby that I could rent for a month. If I didn’t find anything within a month, I’d have to go home. They recommended a place around the corner. I moved in. It was just off of Bui Ven street. If you’ve been to Saigon, you know this street. Madness.

Ok, so how did you find a job then, Isaac?

Well, I knew about the scooters before I went to Vietnam but it’s one of those things that you can’t really imagine until you experience it. It’s absolute chaos.

There are so many people on scooters that I once saw a wreck happen and no one actually touched the ground… they all just toppled over like dominoes, one on top of the other, until they came to a complete stop, and then pushed off one another to prop themselves back up. Look up “Saigon scooters” on YouTube if you don’t know what I’m talking about. It’s incredible.

Anyways, I say all of that to tell you that for the first week or two I was completely mortified to try and ride a scooter. So, yes, I, a 6’4” white male from the US of A, walked around an enormous Southeast Asian city handing out paper resumes to people in person, one by one.

I want you to take a second and imagine this.

Hilarious, right? The door to door sales bros honestly have nothing on me.

I didn’t hear back.

I’m running out of time. Out of desperation, I finally work up the courage to get on a damn scooter.

I’ll never forget pulling over after the first few minutes on that 125cc hog and just looking around. A stranger in a strange land… it was nothing short of bliss. I was running out of money. I didn’t have a job. But this… there’s something magical about being on 2 wheels in a foreign country and not really having a destination. I was headed to the MeKong Delta but I had no idea where I was staying that night.

Somewhere along the way, I stopped for a in a small town for a “Cà Phê Sữa Đá”

In front of the store I stopped at, there happens to be an English school. There’s a white guy out front watering the front lawn. I figure this has to be the owner. It was.

I asked him if he needed any teachers. Of course he did. Low supply! Go figure.

He told me to go get my shit from Saigon and come back. I can start immediately. Wow.

The purpose of this trip wasn’t to find a job. I simply wanted to explore a bit and de-stress. But, life is funny like that. You (often times) get what you want when you stop caring so much.

I throttle it back to Saigon. Can you hear the scooter in your head? Wahhhhhhh.

I pack up and head out for one last dinner on Bui Ven street.

I’m sitting at the bar overlooking the street, minding my business, and a guy named Phil appears out of nowhere.

“Hey, do you want to be an English teacher?”

Pardon me, Phil, but for the love of God… where were you the last 3 weeks?

I told him I’d just found a job in the MeKong Delta and that I was leaving first thing in the morning.

He said, “no no no. I’ve got a house 15 minutes from here. It’s basically a resort. 40 other English teachers live there. Meet up with me in the morning and I’ll personally take you to every school in town. Here’s my card. No one has ever not gotten a job!”

Well damn, how could I say no to an offer like that?

That’s twice in 2 job offers in 2 days without even really trying. Life.

Phil was true to his word. I moved in. It was around $350/month for a room, if I remember correctly. I taught my first class only a few days later. It was in the living room of some random lady’s house to only 6 students. I didn’t care. I was finally doing the damn thing.

A random living room in Saigon! Me, the 23 year old kid from the Midwest. Again, the door to door sales bros have nothing on me.

Here’s a picture of me with the students in front of the house.

I do this for about a month to get some experience and eventually get a job at one of the big brand chain schools in town.

I’m coming up on the 90 day limit for a tourist visa so I need to do a visa run. What the hell is a “visa run”? Yeah, I didn’t know either at that point in time. It was my first time ever doing one.

I’d gotten paid a couple times by then but still didn’t have very much money. All the other teachers told me to just go to Cambodia for a few days and then come back and they’d give me a fresh 90 days. It was the cheapest way.

Cambodia! What?! Isn’t that where… yeah.

I take a bus to Phnom Penh. Add that to the list of places I’d never thought I’d go.

From Phnom Penh, I take another bus to Angkor Wat. I’ll never forget this bus ride. It was the first time I ever experienced real, third world, abject poverty. I’d seen some things on my scooter trip to the MeKong Delta but it wasn’t as bad as this. I don’t even want to go into detail.

Angkor Wat is incredible though, you should definitely go if you have the chance.

On the way back to Vietnam from Angkor Wat, I make 1 last stop in a beach town called Sihanoukville.

I meet a girl from Hanoi (and catch my first case of yellow fever).

We talk until 2 or 3 in the morning on the beach. I don’t remember if it was right then, or a few days later, but I decided to move to Hanoi. The school I was teaching at had a branch there. I was a little worn out from living in the “resort” with all those other teachers. There was a ton of drama. It felt like the show “Big Brother” or some reality show. Not for me.

I went back to Saigon, told my boss I was moving to Hanoi, and surprised the girl a few days later.

I spent the next 80ish days there in Hanoi with her and had a blast, but it was time to get out of Vietnam.

Where to next?

Some of the English teachers at that house in Saigon had told me about this thing called “Workaway.” It’s a website with job postings where you work for “free” in exchange for a room and food.

I found a job posting on the northern island of Japan in Niseko at a ski resort. Ive skied my whole life so I had to go and check out that world famous powder (Niseko has the 2nd or 3rd highest snowfall in the world). I had a month to kill before I had to be home for my sister’s birthday and Christmas. Why not?

I go.

Every night after dinner, me and the guys working there would sit around and talk.

Somehow, someway, teaching English in Central/South America came up. Someone had been there. I can’t remember the specifics. I’d be lying if I said I did. I start applying to schools all over for the following school year (starting in January): Mexico, Costa Rica, Colombia, Peru, Chile, etc.

The first one to reply was a government program in Colombia. The only countries I’d been to at this point were: Australia, Vietnam, and now Japan.

I didn’t know anything about South America, let alone Colombia. Isn’t that where Pablo Escobar is from? I’d always wanted to learn Spanish, mainly because I wanted to read Gabriel Marquez in his native tongue, why not?

You’re probably starting to see a theme here. Most of my 20s is most easily summed up by those 2 words, “why not?”

I accept the job.

I go home for a few weeks for Christmas to see my family for the first time in a year and then it’s off to Colombia.

We’re now in January of 2016. 

I get placed in a small coastal town a few hours south of Cartagena.

I’m the first foreigner that a lot of my students have ever seen.

There were 6 or 7 of us total that were placed in the town. I have 2 roommates, 1 guy from England and 1 guy from Canada. Great guys.

This is when I first start learning Spanish.

Like I said, it was a small coastal town. Most people had never seen, let alone interacted with, a foreigner before so it goes without saying that almost no one spoke English. Every day was a bit of a struggle, but immersion is 100% the best way to learn.

Every morning, I’d buy a newspaper from the corner store and work my way through it, highlighter and all, slowly but surely.

The first week, we have an orientation at a hotel in town. A very attractive girl is working there and helping with the event. Turns out she’s the daughter of one of the managers at the hotel and she’s only working there that day because she speaks English.

As the event ends, I go to the bathroom and drop my phone in the toilet.

Why are you telling me about your phone in the toilet, Isaac?

Well, because my opening line to this very attractive girl was “do you know where I can get a bag and some rice to put my phone in?”

She couldn’t stop laughing.

We talk for 20 or 30 minutes and end up going to a Juan Valdez (coffee shop) nearby. We’re there all evening… and a few hours in she finally decides to tell me that she has a boyfriend. Classic Colombiana move. Great.

We stay in touch and practice Spanish here and there but things never really go anywhere for the first several months (we’ll come back to her later).

I go on teaching. I keep learning Spanish. I make weekend trips to Barranquilla, Cartagena, Bogota, Medellin, etc. All over the country.

Colombia is an incredibly beautiful country and has some of the nicest people you’ll ever meet anywhere in the world. Do not listen to what the passport bros say about Medellin. Colombia is much more than Medellin.

If you’re going there simply to swipe on Tinder… yeah, you’ll probably have a bad time.

I’ve never talked to more abuelitas (grandmas) sitting in plastic chairs out front of their houses and been invited into more homes for dinner than in Colombia. They’d send me off with a full bag of mangoes from the tree in their backyard! What’s better than that?

Or I’d buy a beer and chill with the old guys sitting out front of the corner store and play dominoes while one of them played accordion. This is what traveling is all about.

A quick back story before we move forward. One of my best friends in high school studied Mandarin. The entire time I was in Vietnam, I’d tried to get him to move to Asia with me to teach, but he was stuck in a sales job and scared to move. I get back home to my apartment in Colombia one night and he calls me up on WhatsApp. He tells me he’s finally gonna do it. He’s going to China to teach English and keep practicing Mandarin. Sick! He tells me they’re going to pay him $4k / month! My jaw about hit the floor.

I was only making $500/month in Colombia.

It was technically a “stipend”, rather than a salary, to cover: rent, food, basic transportation, etc.

I’d never even come close to making $4k in a month before.

Naturally, I ask him if he could get me a job.

He does.

Things are happening.

I have a month or two left in Colombia and then I’m going to Shanghai, China to teach.

Shanghai! What?!

Rght as all this happens… guess who doesn’t have a boyfriend anymore!

Women. Gotta love them.

We start hanging out again, but I’ve had enough of this small Colombian town. Shanghai is calling my name. Talk about a change of scenery. A town of ~500k on the Colombian coast to one of the biggest cities in the world with ~30 million people.

I arrive in Shanghai.

There’s 3 of us in a 2 bedroom apartment. The roommate I was supposed to replace ended up having to stay an extra month so I’m on the couch until he leaves. Who cares! I’ve been making $500/month and now I’m about to make $4k/month! I’m riding a state of the art subway everywhere. There’s incredible food on every corner for $3-4. I would’ve slept in a dumpster if I had to.

I could easily write a few articles on China, but walking around Shanghai there’s one thought that persists… “how in the hell does this all work?”

Amazing place to live and visit for a short time but not long-term. If you’re particularly interested in China, DM me anytime. You didn’t come here to read a travel guide about Shanghai so I won’t go much further into detail on that.

Anyways, you remember the girl from Colombia? We stay in touch the whole time I’m in China. We get to know each other really well.

One day, she tells me that she was laid off from her job and had been looking into being an Au Pair in the United States. Cool. I didn’t think much of it.

A few weeks go by. She gets accepted and placed in Seattle. She needs to be there in 10 or 12 weeks. Wow! That was fast! 

My brain immediately thinks, “you’ve got almost 3 months to kill. You should come to China in the meantime.”

Why do I do this to myself?

Keep in mind, this woman has never left Colombia before!

She was obviously excited, but hesitant. Her family was extremely hesitant. But, I’d met them all. They knew me.

Long story short, she comes. She stayed with me for my last month in Shanghai.

Crazy, right?

Were getting very close to how my career in tech started. Hang with me.

During that last month together in Shanghai, she convinces me to move to Seattle with her. “I’m an English teacher though”, I’d say. “What am I going to do for work there?”

Maybe this had been my plan all along. I don’t know. As you can tell, planning ahead wasn’t a strength of mine at this point of my life.

I start looking for jobs in Seattle.

I create a LinkedIn. I’m on Indeed. JobRecruiter. All the sites. I start offering English classes on Italki in my free time (great website if you’re wanting to learn another language, not just English) to try and make some extra money. But we’re talking $1k - $2k/month. That’s barely enough to cover rent in Seattle, if that. 

I rent a micro studio in West Seattle right off of Alki Beach. $900/month. We’re talking micro micro. Full bed. A TV. A sink with a cabinet above it and a shower and toilet. There was a communal kitchen on the floor that all the other rooms shared. It was maybe 250 sq ft. And to be honest, I didn’t really care at the time. I’d had a pretty nice 1BR apartment back in Hanoi for 3 months, but besides that, this was the first time I’d ever lived on my own. 

I end up finding a “Bilingual Paralegal” job at a personal injury law firm just outside of Seattle.

$36k. $2,400/month after taxes.

They needed someone that spoke Spanish.

I was only ~2 years into learning Spanish at this time. I could have basic conversations but didn’t know any legal jargon. I was flying by the seat of my pants. 

Let’s do some quick math. 

$2,400 - $900 = $1,500. Without buying food, paying phone bill, any kind of entertainment, etc. that’s only $50/day to live. In Seattle of all places! No bueno.

On top of the shit pay, the job sucked. The worst kind of job is when you have to dress up nicely but yet barely make more than a fast food worker. You feel like a LARP. It’s only saving grace was that I was able to improve my Spanish quite a bit.

I started doing Uber in my free time and make more per hour than at my damn job where I have to wear a suit! 

I made an excel spreadsheet of all my expenses and showed it to my boss. I think he simultaneously respected me for that… but also hated me at the same time.

I was single. No kids. Some of my co-workers had families! How were they surviving? 

Anyways, he clearly didn’t care because I didn’t get a raise. I put in my 2 weeks and started doing Uber full-time.

I made about $1,200/week. After taxes, it was a ~67% raise!

So here I am, a bilingual 25 year old male with a Business degree driving Uber in Seattle. Not ideal, but I was still young and dumb. I should’ve known better, but I didn’t. I was just trying to survive.

As I’m sure you know, Seattle is a tech hub. Maybe the biggest outside of San Francisco. Definitely top 3.

It seemed like every other passenger I picked up was a software engineer at Amazon or Microsoft. My mind started to drift back to StudentShare, the app I’d built in college. It had been 3.5 years…

What if I would’ve stuck with it? Where would I be now? 

I looked into all kinds of courses, boot camps, internships, etc. They were all too expensive. I had maybe $3k in my bank account at any given time during this period. They all charged $30k+ and/or garnished your wages for X number of years once you were hired.

Not only did I not have the money, but I still had $30-40k in student loan debt from a degree that I wasn’t using. I didn’t feel like doubling that for something I wasn’t even sure if I liked.

So, I kept trying to learn how to code in my free time but I stuck with what I knew. Uber and teaching English online.

I find a Master’s program in Madrid. Linguistics. It was split 50/50 between in-classroom teaching and actual courses (as a student). The $ I earned from teaching essentially offset the tuition. It seemed like a no-brainer.

I enrolled. 

The Colombian girl and I have been dating for a little over a year now, from Shanghai to Seattle, and her contract is coming to an end.

We have 3 months to kill before my Master’s program starts so we decide to head to Spain early. I sell my car again. I’m back up ~$10k in savings, just like before I left to Australia.

It’s funny how life goes in cycles like this.

We arrive in Madrid in June. I’m set to start my program in August.

We get back to the AirBnb after our 3rd of 4th day there and I get on my computer and I see an ad for a coding bootcamp in Barcelona called LeWagon.

Its supposedly the #1 ranked bootcamp in the world, whatever that means. It’s $6k USD. Wow! That feels very affordable compared to Seattle.

You can do the math. I had $10k to my name. $6k for the bootcamp. It’s 9 weeks long.

My girlfriend and I find an apartment in Barcelona with 3 other roommates. They’re all in college. $600/month. That’s another ~$1,200. I’d be damn near broke by the end of the program, but I think it just might work.

If I don’t give this a go now, and I do the Master’s program, then I never will. That’s it. Teaching is my career and I’m stuck wondering “What if. What if. What if. What if?” for the rest of my life.

I can’t do that.

I enroll.

I’m in class every day from 9AM - 5PM. I teach 2-3 hours of English classes online at night when I get home.

Almost zero free time. It’s hard as hell. Nothing makes sense. But, from learning Spanish (I was pretty fluent at this point), I knew that if I just stuck with it, it would eventually click.

Throughout the course, I’d been telling my best friend back home all about it.

He works in HVAC sales.

One day, he sends me a random website and asks if I could make one like that for $500 for one of his clients. I wasn’t 100% sure that I could, but I sure as hell was going to figure out how to for $500!

$500 for typing on my keyboard! What’s better than that? This was the exact moment in time that I became exposed to wifi money.

The bootcamp ended on my 82nd or 83rd day in the EU/Schengen Zone.

We’re in August of 2019.

I had 1 week to deport myself.

I didn’t want to go home.

The Colombian girl and I go to Istanbul.

We book an AirBnb for 1 month. Incredible city.

I’m working on the first few websites for the agency while in Istanbul. They turn out good. Not great. But, they get the job done.

Our first few clients give us a few referrals. Those referrals give us some referrals. The word spreads fast. You can see where this is going. It felt like taking candy from a baby! Why didn’t we do this sooner?

I’m completely absorbed in my work. I’d be looking at an incredibly beautiful Mosque, but in my head I was thinking about the business.

How can I improve the websites. How can we get more clients.

Like I mentioned before with the StudentShare app in college, that feeling of building something… of being on the verge, there’s nothing better.

We’re in October or November of 2019 now.

Without going into too much detail, things with the Colombian girl aren’t going well. We break up. I head back home to focus on the business with my best friend.

It’s end of November 2019.

We’re building 3-4 websites a month and  I’m making ~$3-5k/month.

I am on cloud nine. I’m coding 8 hours a day, getting paid to learn.

A few nights after I’m back home, I go out to a bar.

I hear 3 girls speaking Spanish. I’m back home now, I need to keep practicing. Plus, anytime I hear Spanish in the US, I almost always go and chat up whover it is.

1 is from Spain. 1 is from Colombia. 1 is from El Salvador.

They’re all 3 teaching Spanish at an elementary school in my hometown.

If you know anything about me, you know exactly who the 1 from El Salvador is. My wife!

So, yes. I left home in January of 2015. I’m traveling almost non-stop: Australia. Vietnam. Japan. Colombia. China. Spain. Turkey. And several other places in between. I come home, to my hometown in the Midwest, almost 5 years later, and meet a woman from El Salvador who turns out to be my wife!

Sometimes you just have to accept your fate. There’s no fighting it.

We start dating.

Believe it or not, I picked her up for our first date in my mom’s car! She was with me before I really had anything. Before I had my first “real” job.

Everything is incredible. Business is good. She’s good. Life is better than it’s ever been. 

March of 2020. COVID.

I remember it like it was yesterday. I was watching an NBA game and they stopped play half way through and they announced the season was suspended.

“Wow, what the hell is about to happen?”

I was on the final interview for 2 or 3 different software positions… and everyone announced a hiring freeze. You were there. It was as if the world stood still those first few months.

My wife gets repatriated back to El Salvador in July. The borders are closed. I have no idea when I’m going to see her again. I become slightly depressed. 

Business is still going relatively well because all brick and mortar businesses now needed an online presence. We built tons of websites for restaurants. I keep building my portfolio.

September 7, 2020 I finally get my first “real” software engineering job offer.

It was a local agency that builds custom software for various clients. I’d followed the CEO for months on LinkedIn.

I basically heckled this guy into giving me a job.

Almost every week, or every other week, I was DM’ing him. “What tech do you all use?” and I’d go build something in that and send it to him. I’d send him every new client website I launched. I’d ask his opinion on different articles I read. I swear to you the guy must’ve finally thought, “I’ve got to hire this guy or he’s never going to leave me alone!”

I’ll never forget, his last words before he hung up after he’d offered me the job were “persistence pays off” and he winked at me.

I was ecstatic. This was easily a top 5 moment of my life so far. It was validation. I was legit. I’d completely jumped into the deep end and learned how to swim… well, how to tread water at least!

My salary was $50k. ~$1,800 every 2 weeks, after taxes.

In my final interview, they’d asked me how much I wanted and that’s what I said. I almost certainly low-balled myself but I didn’t care. I was getting paid to write code! I had a company computer. My own desk. A monitor. I was in meetings and sharing ideas. It was electric.

September 20, 2020. El Salvador opens their borders. 

I’m at a crossroads. I love this woman that I haven’t seen in 2 months. I just got my first “real” job in my new career. We’re working hybrid. I’ve only been here for 2 weeks! Surely I’m going to get fired me if I ask to work remotely from El Salvador after 2 weeks… so what do I do? Break up with her?

I figured I’d ask the boss. Again, why not?

Somehow, someway, he understood and agreed to let me work from El Salvador.

Looking back, I have no clue why he did that. I guess COVID? Everyone was going through a hard time. I know that I probably wouldn’t have done that for a brand new employee… but my life would be completely different right now if he’d have said no.

I’m almost 99% sure I’d have broken up with my wife. She couldn’t have come to the US. Sure, I could’ve maybe done the website agency work from El Salvador and been fine… but quit my new software job I worked so hard for after 2 weeks…? C’mon. The first job is the hardest to get.

I go back and forth to El Salvador several times over the next 3 months. The job is great. She’s great. Even with all the COVID shenanigans, I’m back on top of the world. We’re so back.

It’s the second week of December. I’m at home in the US of A. My wife (then girlfriend) calls me.

“Are you sitting down?” 

“Yeah, why?”

“I’m pregnant”

What a rush of emotions. I’ve never been more happy and scared at the same time before.

I’m going to be a Dad?!

The day after Christmas, I move to El Salvador full-time to be with her during her pregnancy.

Bukele had been in an office a little over a year at this point. He wasn’t quite yet the famous international figure that he is now. The first thing you thought of when you heard El Salvador was still gangs. 

I’d been to Colombia and all over Central/South America. I’d been to freaking Cambodia. I was never scared. But to be honest, those first few times I went to El Salvador… I was scared.

But, if you’ve followed El Salvador at all over the last few years, you know how much the country has changed and you know this worry of mine was quickly availed.

April of 2021.

8 months after I’d gotten my first software job, another company starts recruiting me. I’m still in El Salvador. The company I was working for used Laravel heavily. This company needed Laravel devs. As much as we all know and love Laravel, it isn’t the most common backend framework for start-ups, enterprises, etc.

They offer me $80k. $80k! I couldn’t believe it.

I’ve got a baby on the way now. I need to buy a house. $50k just isn’t going to cut it.

I called up my boss. The guy I’d heckled for months on LinkedIn, and the guy who so generously let me work from El Salvador, and told him everything. I was incredibly torn. I’m a loyal person. And yet again, he said he completely understood and he’d accept the other job it he were me. This man is a Saint.

Keep in mind, the company that made the offer was out of California and the company I was working for was based in the Midwest. They couldn’t compete with west coast salaries for someone at my level. I was still very much a junior dev.

My wife is 4 months pregnant. I’m on my 2nd software engineering job. I’m making $80k + the web dev agency money, around $110-$120k gross. Life is good. I feel like I’ve “made it”… whatever that means.

My best friend and I make plans to build houses in the same neighborhood.

Keep in mind, I’m doing this from El Salvador. Choosing the lot. Picking interior designs and colors, etc. The whole 9 yards. 

August of 2021, my son is born. September of 2021, we close on the house. What a time.

We are still awaiting my wife’s paperwork/green card so I fly back home for a week to close and move some stuff in: couch, fridge, bed, etc. and then I fly back to El Salvador. 

The immigration process is nuts. Imagine the DMV but 10x worse. Unbearably slow. 

40ish days after closing, my best friend gets a promotion and has to move! We won’t be neighbors after all… sad. 

The next 3-4 more months are so fun but so tiring. My mother in-law moves in with us (in El Salvador) to help with the baby. This is something I wish other cultures did. What a blessing. Work is good. Son is healthy. Not much to say other than that.

February of 2022 comes around, I get another job offer. $140k plus equity! 0.5%. This might not seem like a big deal, but on a $50-100M sale, you can do the math.

I’d told them I was making $110k, not $80k. If you’re interviewing at new places, you should ALWAYS do this unless your current job is unbearable and you just want to get out ASAP. The opportunity cost for leaving a job where you’re liked, trusted, etc. is worth much more than a 10% raise.

I accept.

I’ve now gone from $50k to $140k in 3 years since I finished the bootcamp. I’m sure you can imagine how I felt. The 2nd job had been validation for me that I’d made the right choice, this was just the cherry on top. 

But, as with most things in life, we’re never simply satisfied, right?

I start wondering, “how much more can I make?” FAANG salaries. Staff engineers at Meta make HOW MUCH?

This article is already way too long. Beehiiv just gave me a warning that gmail might cut of off. We’re 95% done. I promise.

July rolls around.

Remember how my wife and I met in my hometown? Well, she was on a J1 visa as part of a scholarship and it had a “2 year home rule” attached to it. Long story short, this means she had to come back and use those skills in her home country for 2 years after her program ended. Those 2 years were fulfilled this month. 

El Salvador is great. Don’t get me wrong. But, we’re still waiting on her green card paperwork so we start looking around at places we could live for a month or two. A change of scenery. We decide on Argentina. We didn’t want to go too far away because the Embassy could call at any time… but we’d heard it was “like Europe.”

We go for 2 months. Buenos Aires. Bariloche. Mendoza. Mendoza is a 30 minute flight from Santiago, Chile. “Why not?” We go to there for 1 month. 

My mom had been to El Salvador 3-4x already to see the baby. She’s missing him a lot. We look for a “half-way” meeting point and decide on Aruba.

On the 3rd or 4th night there, the embassy calls! My wife’s final interview is scheduled for a few weeks from now on December 15th. Almost 2 years to the day since I moved to El Salvador. 

We move back into the house we built, that had been sitting empty for over a year now, on Christmas Eve of 2022.

We get to the house around 2AM. My wife sees it for the first time in the dark. We sleep maybe 6 or 7 hours and then drive 1 hour to surprise my mom! She had no idea. 

She knew we had the interview but after you’re approved, there’s a week or so delay before you actually get the passport back with the visa in it. We tell my mom we haven’t got it back yet. “It’s probably going to be after the New Year… everyone must be on holiday already.”

I’m sure you can imagine her reaction. 

The next year goes by quickly. I’m living the “American Dream.” Married. A son. Homeowner. Living near my family. All the things. Life is the best it’s ever been. 

December of 2023, the company I work at is sold. Remember the 0.5% equity I mentioned? I get a payout. $80k USD, with EOY bonuses built in for the next 4 years. Wow.

I know you’ve probably seen guys  on money twitter posting screenshots of $80k days, every day, but this is life changing for me. That’s an entire year’s salary for many people.

Incredible.

Alright. That’s my last 10 years in 8,000 words. To be honest, this is way longer than I expected, and like I said, Beehiiv is telling me that Gmail may cut this off because it’s too long, so I’m going to wrap this up right now.

A quote comes to mind to end this with:

“Most people overestimate what they can do in one year and underestimate what they can do in ten years.”

💪