Andrew Henderson is a world traveler, investor, entrepreneur and founder of Nomad Capitalist. He is helping young entrepreneurs create their nomad strategy, set up foreign bank accounts, move their business overseas, obtain the second passport and invest in foreign markets.
Recently, I connected with Andrew on the Nomad Capitalist Podcast and talked about my nomadic journey, mindfulness and entrepreneurship.
Today, I’m thrilled to share my interview with Andrew Henderson talking about his habits and routines. It’s one of the longest, honest and value-packed interviews I’ve ever done. Get a cup of coffee and read on.
Born and raised in the United States, Andrew Henderson is an investor, world traveler and an entrepreneur who left Arizona State University to start his own business and 4 US businesses later, sold everything and decided to travel the world.
While his search began with an idea and a few bucks to invest, he now is investor, entrepreneur and the managing director of Nomad Capitalist. He has a remote team from all around the world and travels around 15-20 countries every year. His mission is to find best places to live and start or move your business, strategies and obstacles regarding getting a second residency or passport, save up and pay less tax and become a global entrepreneur and citizen of the world.
Andrew describes himself as “a border security nightmare who travels from country to country to cherry pick the best economics.”
What Are the Most Influential Habits in Your Life?
One of the things that people who are looking to get into the Nomad Capitalist lifestyle often tell me is that they want more freedom. What I always have to stop and ask them is what the term “freedom” even means to them. Defining freedom – both “freedom from” and, more importantly, “freedom to” — is a first and necessary step to creating the kind of life you desire.
For example, before I became a Nomad or even began traveling frequently, I ran several businesses in the United States. My first business was in broadcasting and, because I structured it to be efficient, there were days that I could sleep late, wake up at noon, and then work during the afternoon. In my early twenties, being able to run a successful business while sleeping late was my personal definition of freedom.
As I got older and more accomplished, I raised the bar. I realized that having a routine is not only important, it is crucial for being successful and having a soul-fulfilling life.
Often, people who want to get into the Nomad Capitalist lifestyle think that it is all about traveling the world dragging a bag behind them, waking up whenever they want, and experiencing something new, different, and exciting every day. I know from personal experience that this is definitely one of the approaches many Nomads choose to take.
After several years of doing this, however, I have found greater fulfillment in creating and following a routine. Now, no matter where I’m at, I wake up at a certain hour, go to bed at a certain hour and do certain things every day.
These daily routines don’t have to be complex to be important, either. For instance, I have chosen to make myself some kind of smoothie or juice every day and to take the time to enjoy it. Every day, I make time to take a one-hour walk without my phone. I take time to be mindful and to focus on what’s going on around me and to enjoy the beauty of the world. And I choose to do certain things at certain times.
Additionally, now that I’ve been to almost 100 countries, I’m starting to slow things down a little, spend a bit more time in each place, and really focus on mastery. I’ve been to most of the places that I wanted to visit and check out for potential clients, and I’ll continue to do some trips to new places, but what I’m really focused on now is mastery.
With that new end goal, having a routine of basic, healthy habits that allow me to take time for myself every day is my new definition of freedom. I have already seen how it is impacting my wellbeing and success.
I have also found that, to make all of this possible, it is important to learn to keep a calendar and delegate certain things to certain parts of the day. Once you do, turn off the notifications on your phone so you are not getting messages at 10 o’clock at night and then wondering why you are anxious about responding.
Instead, set a specific time for when you will wake up every day, when you will handle business, and when you will take time for your personal life. I’ve learned to stick to a calendar, get into routine, slow down my travel a little bit, focus on mastery, and choose to take time for myself.
How Do You Set Goals and Manage Time?
This is an area that is personally in constant evolution. I don’t do post-it notes, but I do believe in the power of writing things down. I also don’t do things like Pomodoro. I keep it simple.
One of the things that has really helped me run my business is getting rid of all the “stuff.” I ran numerous off-line businesses in the US and sold them all before I got into the online world. When I did, I thought it was going to be really tricky and complicated and have a lot of moving parts. However, I soon discovered that the secret to success for getting the end results for the people I’m helping – getting their taxes reduced, getting their second passports – was fewer moving parts.
I found that whenever I ran around like a madman and took on too much, I didn’t get success. When I focused on keeping it simple, the success flowed easily. So I removed almost all the moving parts in my business, including Pomodoro and all the applications.
I largely use Google Calendar to keep track of everything because I can have different people on my team, from personal assistants to people working with clients, all in one place. I can schedule all my activities, whether its clients, a flight, or any other activity. In fact, my flights are automatically posted to Google Calendar by my flight-tracking system.
I try to keep it very simple in terms of managing time. This also helps me with what I said earlier about sticking to a calendar and defining what you’re going to do between, for example, 11am and 1pm every day.
For me, I wake up every morning and I take some me-time. I get ready, then I go for a little walk, then I come back and do some journaling in what I want to accomplish that day. Then I’ll do a lesson in language or something else. After that, I dedicate time to work and I schedule weekly calls if I need to spend time discussing things with anyone on the team.
For me, managing time is a matter of committing. I recently hired a personal trainer and I told them that we would meet Monday, Wednesday, and Friday at a specific time that we are never going to change. It’s the same in every aspect of my life. When I hire someone to teach me a language, I say, “Monday, Thursday, here’s the time, we are never going to change it.” That is the key for me: committing.
That gets me results and it gets my clients results, too. When a client comes and says that they want to get a second passport, but they are disorganized and want to take their time, they don’t get the results they want for months or even years.
To avoid this, I’ve created an organized system based on scheduled communication. For example, my clients can expect some type of interaction with my staff and me every Tuesday to get what they need done. We are not going to exchange 17 different emails at all hours of the day. We are going to follow an organized system and put all the steps in order. We are not going to deviate from that.
Specifying when communication needs to happen is crucial. Setting specific times every week that never change – whether it is for your personal life or for working on your business – has really helped me streamline my life. I do all my calls with clients on Tuesdays. If you want to work with me, or if you are working with me, it’s Tuesday. I don’t travel on Tuesday and unless it’s a half-an-hour flight, I don’t travel on Monday either because I want to be rested and refreshed for Tuesday.
Because I focus everything on Tuesday and I work with a very limited number of people, I’m able to spend the rest of my time doing my stuff, learning things that my clients want to know about, working with my team, and developing myself personally. But Tuesday is untouchable. As a result, I get all my goals accomplished.
How Are You Modeling Your Life?
As a little kid, all my role models were business people. Oddly enough, one person whom I found very entertaining and who made business seem very exciting was Donald Trump. Nowadays, that’s a real shame. I have no comment on the Donald Trump of today, good or bad; he’s a politician. However, it seems like the 80s Donald Trump (real or imagined) was interesting.
Personally, I feel that when we focus too much on a role model, we tend to look superficially and not at what actually works for them. A guy came to me once and told me that he wanted to emulate “Frank’s” business. He wanted to emulate everything that Frank was doing. The problem was that he didn’t know why Frank was doing any of it.
If you don’t know why your role model is doing something, how it works for them, or how it serves them, and you’re just copying what they’re doing on a surface level, then that’s not going to work for you.
That’s the challenge of role models.
Tim Ferriss, who wrote The 4-Hour Work Week, is like a god to many people who are living nomadically. What I’ve learned is that when you’re new at something and you’re trying to start a business and you don’t have a lot of experience (not to any fault of your own), there is a tendency to rush towards Tim Ferriss and do everything Tim Ferris does, despite not knowing why he does it all or whether it will work for you. You’re not Tim Ferriss, and what he does isn’t necessarily what you should do.
So, what I’ve found is that when you get to the level of guys who are really crushing it in business – I mean, high six figures, seven figures, multi-seven figures, even eight figures – what they do the best is to cherry pick and adapt. They focus on learning very key concepts. That’s what I try to do too.
On a personal level, I have really gotten into mindfulness. I make an effort to focus on what’s happening now, which allows me to kick out all distractions. This is a challenge for a lot of people, especially in business. I know it was for me. You’ve got 92 million things running through your mind, your thoughts are racing, and you can’t focus on solving the problem.
Sometimes, I can’t help those folks, or I refuse to help them because I don’t need that kind of stress in my life. I prefer to work with individuals who can be mindful and focus on how to solve the problem at hand.
So, for me, mindfulness has been good, but I’ve become averse to adopting role models and have focused more on a model of hiring mentors and coaches in every level of my life, from personal trainers to business coaches to emotional coaches (helping me with anxiety and focus). I’ve hired many different coaches over the years and I’m a big believer in the value they add.
It took me a long time to come around to that, but they teach me very simple concepts that add exponential value to my personal wellbeing and professional business success. You can easily find this by hanging out with people who are just a few steps ahead of you. You don’t need the 1980s version of Donald Trump as a role model (someone so big that they will inevitably “let you down” in one way or another). You need someone who can help you see how to take the next step forward.
That means that I may choose to hang out with guys that are making millions simply because they will often make comments that really stick to you. I may also learn one very simple thing from a ten-grand mentor that you wouldn’t think was worth the money, but you take that one thought with you wherever you go and it totally colors your world and refills your mind.
So, for me, the mental model is just about a very simple actionable thing, like how to deal with anxiety by going out and taking a walk once every day. I prefer simple principles over superficial role models. Principles can be applied to personalized circumstances, whereas trying to emulate a role model can lead you to trying to become someone else and do what works for someone else instead of focusing on your individual situation, gifts, and needs.
For instance, I see people who have role models who moved to Bangkok and then they just want to become them so badly that they move to Bangkok. But maybe Bangkok isn’t for them. It worked for their mentor and that’s great, and maybe it could work for them too, but first they need to assess why the role model went to Bangkok and why they’re going to Bangkok as well.
The same thing applies to people who start offshore companies or want second passports. So many times, people call me to say that their friend who’s an Amazon seller told them to set up a company in Hong Kong because it worked out for them. However, often times these guys have literally made their tax situation worse by taking their friend’s advice. What worked for their friend who is British doesn’t work for them because they’re American. These folks can cost themselves a lot of money by simply having the role model when in reality they needed to follow the right principles.
In summary, instead of looking for role models, ask yourself, “What do I need? What are my challenges? How do I operate?” Then simply find people who can provide you simple solutions with which to operate.
Can You Describe Your Work Process and Thinking Behind It?
This is one of the things that I’ve had to improve because I’ve been an entrepreneur since I was 19 and there was a lot of inefficiency when I was younger. There were a lot of things I didn’t know and that’s why I like mentors — they help you shortcut the system.
It took me a lot of years to get my first second passport, then the next one came within months, then the next one was also fast. It’s similar to becoming a millionaire, the first million is the hardest, but after that it gets easier and easier because you’ve learned the principles that keep the money rolling in.
I found that there were a lot of lessons I could have learned from people early in life that would have helped me shortcut the system even more quickly. I have no regrets about what I did, but when you ask me about my working process, I really focus on prioritization where I say “Is this urgent and is it important?” There are certain things that are urgent and important and those get handled first, then there’s urgent but not-important, and so on.
A lot of us, my past self included, put every to-do on a list and then we try to knock it out any way that we can. For me, I try to prioritize what’s the most urgent and what’s the most important.
I have also found that communication is one of the most effective things in terms of a work process. You have to let everyone know what you are doing. For example, Tim Ferriss explains that when somebody calls him and wants to chitchat he’ll just say, “What can I help you with?” He gets right to the point.
What I found is that when I tell someone I am helping that every Tuesday we are going to send them a list of what we have accomplished for their case and what we need from them before the next Tuesday (a copy of their passport, a notarized document, etc.) they know exactly what to expect from us and what we expect from them. They know to expect an email every Tuesday. They know that if they send us an email on Monday morning we are going to reply to it on Tuesday. I’m not running an emergency room in my business.
I’ve found that people can clear their heads a lot better and get a lot more accomplished, and so can I, when we have clear communication about expectations. If you are working with me to get a second passport, there’s no need for you to send me three different emails a day with your random thoughts.
So my work process is prioritizing and communicating how I prioritize what’s important and what’s time-sensitive and then, from there, the plan falls into place.
As to my personal stuff, I do outsource a lot. However, I had a mentor once tell me, “You know what, you can’t outsource your anxiety, you can’t outsource everything”. I’ve found that we tend to think that if we hire that property manager, or Person X to handle Issue Y, it will solve everything. It doesn’t always solves the problem, there’s still management going on.
Again, for me, removing moving parts has been key. It’s not just about building the work process, but also removing all the moving parts that are unnecessary. After that you can prioritize, communicate, and then whatever is left you can outsource. But you have to be careful what you outsource because if you outsource too much you’ll create a bigger challenge.
You don’t want to be one of those people who hires a personal assistant and then becomes frantic trying to find work for them to do just so you can say you are outsourcing. Outsourcing for the sake of outsourcing is a waste if you are not eliminating the nonsense or communicating properly.
What Do You Eat for Breakfast?
I’ve never really eaten breakfast in my entire life. The only exception is if I wake up at four in the morning for some reason, like if I have to go to the airport, I want a hot breakfast. There are other little exceptions, for instance if I fly to a new place and I have jet lag.
Once, when I was staying at the Ritz Carlton a while ago, I had a lot of jet lag and was sleeping at crazy hours for the first couple of nights. I woke up in the morning about 3:30 am and by the time 8 o’clock arrived, I remembered the free breakfast and so I went and had this phenomenal hot breakfast. In those cases, I’ll indulge and get one of those hot breakfasts. But, in general, I’ve never really eaten breakfast.
I actually came across a study recently (although I really don’t follow studies because they are often more contradictory than anything else), but this one said that there’s actually a benefit from fasting about 14 hours at a time. If you finish eating diner at 9 pm, and you don’t eat again until 11 am or afternoon the next day, then your body starts to cleanse itself out, and that’s exactly me. I don’t want to wake up in the morning and eat breakfast; I wake up and I want to get to work. I wake up with a sense of purpose and I want to get stuff done. So, breakfast is really not for me.
How Do You Train Your Body and Mind?
I’ve focused on reading more. The problem is, and again this is a matter of me scheduling my time, there are times when I don’t schedule enough time for reading. I tend to leave that one aside, but I have been listening to a lot more audio books.
The less time you spend on a plane, the less time you seem to want to listen to audio books. When you are a Nomad, you don’t commute, so you do miss out on the time that most people who are used to living in a city listen to audio books and podcasts. If you are not taking the metro or driving to work in your car, you have less time to listen to this stuff, but reading is good for me.
I also hired a personal trainer and I started to feel really good about myself. I started to feel healthy. I’ve also hired people to teach me a language. It’s very important to develop yourself.
I’m not into yoga and I don’t do much meditation, but I have enjoyed focusing on mindfulness. I’ve benefited greatly just from being able to sit and say, “How does this food taste in my mouth?” or, “How does the breeze against my cheek feel right now?” Learning that “right now” is the only thing that really matters has helped me immensely. The thing that you think might happen a week from now isn’t happening now; it’s in your mind, it’s a figment of your imagination. It’s all about training your mind.
There are times when I do get caught up at some stress of the moment, but that’s when the mentors come in. Sometimes they give me little phrases, or if I remember those phrases on my own, they work as triggers to help me say “Hey, I need to be mindful.” We should all have personal triggers like that.
For me, hiring a personal trainer was a great decision, it also reinforced for me that I’m not the boss of everything. Many believe that great customer service means that customers need to get their asses kissed. That’s nonsense. I don’t go to my trainer and say, “I’m a paying customer; I refuse to do 18 push-ups.” No! Instead, I say, “This guy is smarter than me when it comes to personal training, so I’m going to listen to whatever he says and I’m going to do it, without complain. He is the boss, I’m paying him to be the boss.” So, I’m a big fan of hiring people, tutors, trainers, mentors.
How Do You Meet and Connect with People?
There’s a great quote from a guy with whom I’ve been working that says: “The guys at the six and seven figure levels, they’ve said ‘yes’ to a lot of things; the guys at the eight figure level have said ‘no’ to a lot of things.” So, I’m hyper-focusing on what I want.
I tell people who want to work with me that it’s either a “Hell yes!” or it’s an outright “No.” I’m not going to take ‘let me think about it’ or ‘let me dip my toe in.’ ‘Hell yes!’ is doing jumping jacks and loving it; anything else is a ‘no.’
I’ve taken the same approach with friends in a social context. I have a hundred or more people adding me (or trying to add me) on Facebook every month saying “Andrew, I love what you’re doing on Nomad.” And it’s not because I don’t like them, it’s not because I want to be rude, but I don’t want to let people into my life who are just going to kind of sit there on the shelf. I want people who really empower me, who drive me, who make me think, who motivate me. And, for me, that’s just a very few people in my life right now.
I have an amazing team of staff and I really enjoy connecting with all them. I have great personal relationships and, quite frankly, I don’t add people I don’t know that well anymore. I am a Nomad, but I’m capable of living somewhere and not having any friends on the ground. When and if I meet people who share my interests in business and in operating on high levels and self-development, I’m into it.
I’m not into being labeled as part of a community. People will often say “Oh, I’m a digital nomad.” But now they’ve just wallpapered themselves into the digital nomad community. That’s fine and may even serve them. If so, that’s great. But I do think that the saying “your network is your networth” is very true. If you just hang with people who are exactly like you, you’re not going to improve.
I like people who can take me to the next level. That’s hard to find and it’s kind of lonely. They always say that “it’s lonely at the top,” but it’s actually lonely heading to the top as well. I don’t really go to conferences or do so much social media. I like to find people organically and not on social media. For me, the secret is organic rather than going around forcefully trying to meet new people.
What Are Your Sleeping Rituals?
It’s tougher when being a nomad because, even now that I’m traveling slower, I’m going to take some side trips to explore banks or passports or to do whatever I need to do every once in a while. But my thing is I want to be in bed by 12:30 pm and up by 8:30 am.
One of the things that I have overcome is the driving desire to be different. I always felt different. I was kind of the guy who people didn’t understand when I was young. I was bullied, not physically much, but emotionally when I was a younger kid. Many people made fun of me, I wasn’t understood, and I almost kind of clung to that. I wanted to be misunderstood. As an adult, I’ve had to learn when being different still works for me and when it actually gets in the way.
For example, as the Nomad Capitalist, I don’t hang out in Bangkok, I don’t hang out in Chiang Mai, I don’t hang out in Barcelona, I don’t talk about being a ball or a bra because, a) I just don’t want to, and b) I’ve just always been different. So, one of the things I had to get over in terms of sleep was waking up at the same time as everyone else does. I wanted to be different, just for the sake of being different. But, that wasn’t helping me when it came to sleep.
What I’ve found is that I’m the most proactive and the happiest, honestly, waking up no later than 9:30 am. I always want to run outside and start doing things once I get up. I want to be out with the world. So, for me, I’m in bed by 12:30 pm and up by 8:30 am. Sleep has become important.
When you’re a young entrepreneur you say “I’ll sleep when I’m dead”. But, give yourself time to sleep, stay in shape, and respect your body. Sleeping for six hours isn’t going to make you more productive because you’ll be dragging yourself through the day. I’ve really come to appreciate the value of sleep, the value of taking time for yourself, and the value of not working yourself to the bones.
What Are Your Investing Habits?
I basically like to live by the phrase, “Live well beneath your means.” I’ve always been that way. I can get a pair of Gucci shoes as a reward to me for a good month or for a great deal that just closed successfully and everyone is happy. Maybe I made 50k in a deal and I’ll go and buy a $500 pair of shoes. I’m not going to spend 80% of what I just made as so many people like to do.
I’ve met plenty of folks who make millions of dollars a year and yet they don’t have anything to their name. They just go and blow it all because that’s what you do. I’ve always been very self-conscious and aware that all the success could end tomorrow. For years I would wake up and say, “Oh, last month was a record month for my business, but this month it will all end. I can feel it.” And every month I made more money (with a few exceptions).
That attitude made me work more and learn more every month and every year until I finally got to a point of success where I could say that it could all end and I would be fine. I had accomplished enough and could retire comfortably if needed. So no more stressing out or getting frustrated about what might happen tomorrow.
For me, defining investments is very important. For example, investing in furniture is not an investment. I like to keep a lot of cash on hand, I’m a big believer in having an emergency fund. I’m also a big believer in having different kinds of cash like gold or physical cash, cash in the bank etc. There’s a benefit to reaching a certain level of success when you can say that not every dollar needs to be working for you and can just be available if you have to pay for something in an emergency or anything.
I also like to invest in real estate all around the world, particularly in the places where I work and visit most often. I do this, essentially because I work better, I function better and I’m more productive if I feel at home whenever I’m overseas doing business. So I buy properties, decorate them how I like, and do everything to feel at home. Before doing that, I would stay at good hotels with nice rooms and felt that was also a great decision because I tend to work better in a place where I feel more comfortable.
What Books, People, Experiences Shaped Your Thinking?
There are so many books. One of them is The Subtle Art of Not Giving a F*ck by Mark Manson. In it, he talks about chasing the highs, chasing dopamine, always looking at your phone, always treating yourself like a slot machine and thinking about the next thing you can get.
I really enjoy traveling, but I did find that I was recently planning to go to Belarus simply because it was the last country for me to visit in Europe. I thought, “Oh, that would be great to cross all of Europe off the list.” But then I realized that I didn’t have a real reason to go to Belarus. I didn’t even think I would enjoy it and I am almost positive none of my clients or people I’m working with will want to invest there. So what was I going there for? Just to cross Belarus off the list? So, The Subtle Art of Not Giving a F*ck really impacted me in that regard by helping me reassess why I do what I do.
There are so many books. There are the basic ones, like The 80/20 Principle, that are good. I have a mentor and a friend, Matt, who really focused me on building the confidence to understand what I’m offering. In my business, we have more people coming to our website than any other website of its kind, and yet people are still coming and saying, “Aww, I want to think about it.” Matt helped me create a system where I can screen those people out.
With that system, I only work with who I want to work with, which means I reject 99% of the people who come to me for help. I take only the best and I hold them to strict principles. I take command and I build up the confidence in my own business by working with mentors and solving real problems by taking control of the situation, not out of anger or ego, but out of the desire to help.
Interestingly, by doing that, what has happened is that when the rare person comes along and says “Andrew, I’m not ready to commit to getting help to my problem today,” instead of thinking that I missed an opportunity, I say, “Thank God I’m not going to be burdened with someone I have to drag through the mud all for a tiny sum of money, several thousand dollars.”
For some people it might come naturally to run their business that way, but I have had to learn all of this through experience. The “Hell yes!” and “Hell No” rule has been life changing in that regard. And all of that came from a friend who doesn’t even work for the business. The right lessons come along the way.
In a nutshell, it comes down to focusing on mindfulness, confidence, and knowing exactly what I want. The Subtle Art of Not Giving a F*ck helped me understand those principles. I also enjoyed Everyday Charisma, which basically teaches you to be who you authentically are, don’t take anything personally, and if people don’t like it, that’s on them, don’t assume what they’re thinking”. Those are lessons that have really helped me.