Hey there 👋

If you’re an OG reader: welcome back!

For those of you who are new here, I’m Ben, a solo founder and expat from the USA although I’ve been living in Bangkok, Thailand for the last year and some change.

With that said, this is going to be a bit of a different post, deviating from my usual “how to do something interesting and technical” post format, but I think this information will be equally interesting and maybe even more enlightening for those of you who might be considering a move overseas or making major life changes.

This is going to be a fairly long explanation as the reasons I ended up here are complex, so let’s start from the beginning, shall we?

So how did you end up in Thailand anyway?

Well, it’s a long story. Thailand was actually the first place I ever traveled on my own over 10 years ago, so it wasn’t my first time in the country when I landed here a year ago.

I was dealing with some serious family issues at the end of 2013 which was affecting my mental state, self-confidence, and relationships with other people in a number of negative ways. This was all happening right when I was getting ready to graduate university and take a bunch of final exams, so there was added stress from multiple angles.

As a result, and pretty much as soon as I graduated in December 2013, I decided that I wanted to get out of the country entirely and do a trip on my own to mentally reset. Pieter Levels talks about this idea of resetting your life in his own blog from many years ago and I did the same thing, coincidentally right down to the same choice in country.

How did I pick Thailand as the destination? Well, almost at random. I had never been to Asia or Thailand, I didn’t speak Thai, and I didn’t know a soul there. Really, I barely did any research and simply committed to the idea after a quick Google search for “good countries for solo trip” and noticing Thailand looked cool and was at the top of the list.

The other tricky part about this was that I had an engineering job already lined up for post-graduation and they were expecting me to start work within a few weeks, but I managed to convince the recruiter (hey ex-coworkers from Qualcomm if any of you are reading this) that I needed extra time before starting “to wait for my apartment lease to finish.”

You’re probably wondering how I managed to convince the recruiter using that laughably weak excuse, and I have no idea, but it worked. I was able to successfully delay my start date by 6 months! With that problem solved, I booked a one-way ticket, booked 3 nights in a random hostel, hopped on a 24+ hour economy flight across the world, and landed in Bangkok at 3 in the morning.

Let’s say that “culture shock” was an understatement when I landed. The first thing I noticed was how many people there were on the street - I had only lived in small towns in the US my entire life, so this was a completely different universe. I then had to navigate past a million speeding motorbikes, half of them driving past me from both directions on the sidewalk in order to find the hostel I had booked, then step over about about a dozen sleeping backpackers - because half of them were passed out drunk on the floor - in order to find my assigned bunk.

But after that crazy first night in the country, I quickly got used to things. I ended up meeting a bunch of cool travelers throughout my time in Thailand, toured the entire country (Bangkok, Ayutthaya, Chiang Mai, Pai, Chiang Rai, and so on) with the same people I had met staying at various hostels, and then acquired a last minute visa and flight to Burma to see Bagan, Yangon, Inle Lake, and a bunch of other unique places and met even more people.

But after a few months in Southeast Asia, and although I was heavily considering moving to Chiang Mai where my friend was paying less than $100/month in rent, I decided it was time to come back to the US. I really did want to get some work experience and get good at being a Software Engineer, so I decided to prioritize that over backpacking Southeast Asia indefinitely.

Well then, what brought you back to Thailand?

After 10 years working in software full-time, including my most recent almost 5 year stint at DoorDash in SF and NYC, I felt it was time to start my own business - again.

I say again because I’ve been starting businesses from a relatively young age. I’ve always been drawn to business and leadership for some reason even though no one in my direct family operates a business.

For example, my first venture was flipping web hosting accounts to random people I met on some kind of pirated software forum when I was 17. I ended up making around $500 in total revenue with only $10/month in expenses, which felt like big money in high school, but I ended up getting hacked and doxxed by a black hat hacking group and being forced to refund all of it as the web hosting account got deleted. That was a crazy experience to go through keeping in mind I was still in high school.

A few years later, I followed that with a liquor app that helped people navigate the commie liquor system in Virginia. When I say commie, the liquor stores are state-owned, and the government sets the prices for all the liquor sold in those stores. You cannot buy liquor anywhere but these specific stores either. Very commie.

In any case, I indexed all of this stuff and made it searchable via an app:

This liquor app effectively paid my share of the electric bill in college due to people buying the app for $0.99. Of course, I again thought I was rich with ~$100-200 in total revenue and I remember getting recognized as “that guy who built the liquor app” at a house party once or twice. Best of all, no hacks occurred and I got to keep the money.

Most recently before quitting my job at DoorDash, I had attempted a motorcycle safety business that only made $10 in revenue. I shut it down for a while, but I actually just relaunched it a few months ago after a fellow founder gave me the idea to relaunch it as a SEO experiment.

Anyway once I quit by job at DoorDash, I decided I wanted to make a real effort at starting a business. Not a toy project, something that would actually generate real and consistent revenue and that I could say I came up with myself.

But there was a problem.

What was the problem?

I was living in NYC at the time after just having quit my job at DoorDash. I love NYC, but it’s also incredibly expensive for a founder starting from scratch with $0 revenue and no desire to get VC funding.

I decided that there was no real point in paying $3,200/month in condo rent to live there while having exactly $0 MRR and having no idea which business idea would start to make consistent revenue. I wanted to lower my expenses and my risk while I figured out what I was doing.

So, fresh out of a relationship that had ended right around the same time, I decided it was time to consider moving. I had previously traveled all across the US and I liked Austin, Denver, San Diego, and some other places I had been to or lived in before - but again, I felt it was time for a more drastic change as I needed to significantly lower my expenses.

Where else did I consider?

Before I decided on moving to Thailand, I decided I should do some scouting of other locations in Asia to make sure it was the right fit.

On X, everyone talks about the dream of moving to Bali as a software founder and living that DiGiTaL nOmAd LiFe, so that’s the first place I decided to fly to. I heard a lot of high praise from people who had been there 5-10 years ago, but as it turns out places change.

Let’s just say I was severely disappointed when I got there. The most famous destinations on the island were absolutely overrun by tourists, developers just keep building beach club after beach club, the traffic is the worst I’ve ever seen (I’ve been to Hanoi so I know what a lot of motorcycles looks like, this is worse), the sidewalks are very small and falling apart, and there’s generally no infrastructure to support the massive influx of tourists.

There’s also poor internet freedom in Indonesia - you’ll need a VPN to access most things and you’ll be IP blocked by either the ISP in Indonesia or the service you’re trying to access as many websites simply blanket ban all Indonesian IP addresses.

Finally, the food, as the kids say, was pretty mid. There seemed to be lots of rice + chicken + egg dishes which were bland, but I did really like Babi Guling which is a must try if you go there. My favorite part of the whole trip was traveling to a nearby island (Nusa Penida) and exploring it by motorbike, and I felt the local people in Bali and Nusa Penida were really nice. Overall though, just not the vibe I was looking for at all. Too many obnoxious tourists and influencers everywhere.

I then visited Kuala Lumpur, Malaysia and multiple cities in Vietnam. Malaysia is an interesting country because the visa situation is generous (90 days per entry, plus they have a 1 year visa, as well as longer term options), everyone speaks near perfect English and the local food is seriously great. But as a place to live, I felt it would be a bit too low key for me and it has a fairly “dead” energy to it. Hard to describe but I felt it as soon as I got off the plane and rolled into the city. That said, it seems like a great place for families, less so someone in my position who feeds off the energy of the place I’m living in. That said, I’d like to go back and explore some new places outside of KL since Malaysia is so close to Thailand. I’ve heard good things about Penang.

Vietnam was also a very nice experience. Hanoi in particular has a lot of character to it and there’s a ton of history, cultural sites throughout the country. Food was good as well, and Vietnamese food at least feels healthy to me as there’s a lot of vegetables incorporated. However, the visa situation for anything outside of a tourist visa is difficult. Even the longer term visas have stay limits of only a few months per year. I like to be in one place while I’m focusing on business stuff, so Vietnam didn’t seem to be a good option for this reason alone.

In the end, mostly due to visa flexibility, food options, safety, internet freedom and speed (I rarely if ever need a VPN in Thailand), and general ease of living or at least my estimation of how all of those things would be: Thailand won.

So did Thailand live up to my expectations?

In a word: yes. Thailand is great, and it was absolutely the right move while I was getting started with business, and still feels like a nice place to live. But there are some pros, neutral points, and cons you should be aware of when you move here, some of which have become more painful for me recently.

Again, I should note that these items are unique to me, and you may have a very different set of pros/cons depending on your situation, but here they are:

✅ Great community of expats and bootstrapped founders. This is what I really wanted moving to Thailand as these groups are less common in the US. Join Hackumvit if you want to meet some of them, I’m a member so you’ll meet me too.

✅ Really nice and technologically advanced condos at reasonable prices. I’m paying $1,000/month and my building has a sauna, steam room, rooftop pool with a full view of the skyline, 2 coworking spaces, gym, automated parking, and the list goes on. Security is really good with facial recognition + fingerprint scan. The same condo in a major American city would be 5-10x the price or might not even exist with the same set of amenities. You can find apartments as cheap as $200/month here if you don’t need amenities and don’t care about being near public transit - good luck doing that in any major city in America!

✅ Friendly local people. I think the “land of smiles” thing is a bit fake, but people are really nice overall and society is a lot more cohesive and less individualistic than it is in the west.

✅ Lots to do with ancient temples, plenty of great local food options (BKK is famous for street food), really good international food from pretty much every country around the world, and tons of outdoor activities. You can take a cheap plane flight to see islands with crystal clear water, go hike mountains, stay in BKK to experience city life, etc.

✅ Very safe. I can walk anywhere in Bangkok any time of the night without needing to be too careful. I haven’t seen any kind of crime here and even the few homeless people I’ve seen in Bangkok act respectfully and don’t bother you.

✅ Public transit is overall very good and very convenient here and I use it a lot… but it has some flaws. Don’t get me wrong, it’s certainly better than you’d find in 99% of the cities around the world and I like it overall, so I consider it a positive. It’s also significantly safer than the NYC subway - again, no crime or sketchy people. The main issue I have with it is that it doesn’t have the dense/extensive transportation network you’d find in somewhere like NYC or Tokyo, the fares are not flat rate so they add up quickly if you use the train a lot, and it’s relatively slow, so if you’re in a hurry or need to directly connect to your destination, it’s best to take a motorbike or chance it with a car and hope there’s no traffic. Note: The most popular train system here is called the BTS (Bangkok Sky Train) but I heard a local call it Be There Slowly and I can’t say I disagree!

⚠️ Service at restaurants is not what I would call “attentive” on average. For example, servers in restaurants here do not work for tips, so they’re not going to put in a lot of extra effort to make sure you like your meal. If there’s a mistake on the bill or something went wrong, they’ll address it - but in the US they’re usually overly apologetic and give you a free item to make up for the mistake or something like that because they’re worried about not getting a tip. That doesn’t happen here. You will also have to wave servers down to get the bill or get their attention which can take some time if it’s a busy restaurant. This system in Thailand is a better system overall as it means patrons don’t typically subsidize salaries for restaurant workers as is the case in the US, but it’s something to keep in mind. This is also negligible for Europeans who are already used to different service standards, but it might be more noticeable if you’re an American and particularly if you’ve been here a while. I personally don’t mind this that much but it’s worth pointing out.

⚠️ Pollution is not great for ~4 months out of the year, especially outside of rainy season. Most people who live here get an air purifier to help work around this which is a workable solution, but sometimes you just want to go outside and you can’t reasonably do that without killing your lungs because of the bad air quality. Then again, there are places in the US where it’s too damn cold to go outside for 4 months out of the year, so this is really a neutral point.

⚠️ Logistics is not quite as advanced or convenient as it is the US for certain items. I’ve had a great experience with Grab which is the local version of DoorDash/Uber, but for certain retail items you will likely use Lazada, which is kind of like Amazon. While Lazada has a really cool app that has minigames and rewards for shopping, it’s a miss on the logistics side of things - it’s just a marketplace for sellers who each individually pack and ship items in most cases, so it’s easier to get scammed and end up with a fake product (you need to stick to “flagship” shops, and the algorithm won’t always recommend them to you). Shipping times are slightly slower, and I’ve also overall found returns to be a pain here - you need to upload pictures of the items, provide a written justification for the return, and drop off the package with a label. The seller can also choose to not refund you the full amount after all of that.

❌ The language barrier here is a real struggle, it gets tiring, and there are many times I miss being able to have nuanced or slightly more complex conversations with locals. While there are plenty of expats here who speak English and you won’t really have issues ordering food using broken Thai or even full English, the level of English for most locals here is pretty poor, which impacts everything from relationships (if you plan on dating locals - I tried and I had to end a past relationship over communication issues, it really did get in the way) to everyday transactions. For example, I recently had a repairman on my way to my condo, and I couldn’t properly communicate how to get there or what time he should come by, and I had no idea what he was saying on the phone as he didn’t speak any English. One or two of these interactions is not a big deal, but when it becomes regular it does get more annoying. That said, learning Thai is definitely possible and I’ve picked up a bit of it, but as it’s a tonal language with a completely different character-set, it’s not anywhere near as easy as learning something like Spanish for a native English speaker. It takes more time and effort for sure.

❌ Thailand is very far from all of my friends and family back in the US. Flights back to the states are 24+ hours long assuming you don’t hit any delays, and it will absolutely wreck your sleep for a week every time you do one of these trips. This has been become more apparent recently as the last trip back was particularly brutal, and during that trip I realized I’d like to spend more time around my aging parent as well as old friends who I would like to see more often.

❌ I like trading stocks sometimes (yes yes, I should just be investing in ETFs anyway, I get it), and stock market hours are not convenient while living in Thailand. I switched to a 100% ETF strategy while living here so I could completely disconnect from the market, because otherwise I’d have to start trading at 9 PM and end at 4 AM which is just not doable in any way.

❌ This is only a negative for me personally and only showed up recently as I started making monthly revenue: my most successful business so far, Watchdog, has most of its customers in the US and some in Europe. I feel like I’m not giving my customers the fastest support I could be giving them because of the massive time difference (usually a full ~12h for US customers)*. In addition, there are certain tradeshows and events I’d like to join (related to my ideal customers’ backgrounds) that are not available in Thailand. In NYC I’d have instant access to these kind of events which I expect to lead to better connections and business growth. Of course, I couldn’t have predicted the need for this before I figured out which business idea had some promise.

*Yes, I could hire support staff in different timezones, but it’s not the right time to hire other people given the amount of revenue coming in, so that’s not an option right now. I’m really focused on supporting my initial set of customers myself so I can build the best product possible.

Conclusion and “Am I staying or what?”

Well, the short answer is: I’m probably moving back to the states, but I’ve recently signed a short term lease in a new neighborhood in Bangkok to give myself a chance to think about this a bit more and put more effort in to learning Thai before I commit to moving back.

I mentioned a few cons that I think are important to address in the next few years and those are best addressed from the US, but I want to make absolutely sure that I want to make the move and give myself a fair shot of making things work here first.

That’s it, thanks so much for reading and hope you learned something!