How to Run a Business While Traveling the World (My Guide)

By Stefan Ciancio on 2026-03-27

TL;DR: Running a business while traveling requires building robust, asynchronous systems for your team, tech, and finances. Focus on a business model with low operational drag, like SaaS or content, hire autonomous people, master remote communication tools, and get professional help for legal and tax compliance to make it sustainable.

Quick answers

What is the best type of business to run while traveling?

The best businesses are digital and not tied to physical location or inventory. Software as a Service (SaaS), like my company WebinarKit, is ideal due to recurring revenue and scalability. Content businesses (blogging, YouTube), digital products (courses, ebooks), and high-ticket consulting are also excellent choices. Avoid businesses that require shipping physical goods or have intense real-time client demands, as they create logistical nightmares across time zones.

How much money do you need to start a business while traveling?

This splits into two buckets: business startup and personal runway. You can start a lean digital business for under $1,000 using smart tools. Your personal runway is more critical. I recommend having at least 6-12 months of living expenses saved. If your monthly burn rate in Thailand is $2,000, you need $12,000 to $24,000 in the bank. This buffer is your freedom to build without panicking about immediate revenue.

Is it hard to manage a team while traveling?

It's challenging but not hard if you hire correctly and build the right culture. The key is hiring self-starters who don't need hand-holding and establishing an asynchronous communication model. We use daily stand-ups in Slack and detailed project briefs in Asana. If you need to micromanage people in real-time, you've already lost. Trust, clear KPIs, and good systems are more important than being in the same time zone.

How do you handle taxes and legal requirements?

You hire experts. This is the single area you should not DIY. I run my businesses through a US-based entity for simplicity and access to payment processors, but my situation is unique. You need a good accountant who understands remote businesses and an attorney for contracts. Trying to navigate international tax law and corporate structures on your own is a recipe for disaster. Budget for professional services from day one.

What is the biggest challenge of running a business abroad?

The biggest challenge isn't Wi-Fi or logistics; it's the mental grind. Time zone fatigue is real and can burn you out. It's difficult to be creative or strategic when you're constantly doing mental math on meeting times. Loneliness and a lack of routine can also kill productivity. You're not on vacation. You must build a disciplined structure for work, or your business and your well-being will suffer.

What are the essential tools for a traveling entrepreneur?

Your tech stack is your office. Mine includes Slack for communication, Asana for project management, Google Workspace for collaboration, 1Password for security, and a reliable VPN like NordVPN. For marketing, my own tools like Maker AI and PressPitch AI are central. For finance, Wise (formerly TransferWise) is non-negotiable for international payments. A solid laptop and noise-canceling headphones are a given. I cover my full gear list further down.

Stop Dreaming, Start Systematizing

Everyone romanticizes the idea of running a business from a beach in Bali. The reality is sand in your laptop, terrible glare, and no power outlets. The dream isn't the location; it's the freedom. And freedom isn't found in a plane ticket; it's built with systems. Before I could even think about traveling, I had to fire myself from the day-to-day operations of my businesses. In the early days of WebinarKit, I was the head of customer support. Every ticket, every question, every refund request came through me. It was chaos. We were growing, which was great, but I was chained to my desk for 12 hours a day. The business owned me. The shift happened when I realized I was the bottleneck. My goal changed from 'doing the work' to 'designing the system that does the work'.

We started by creating a knowledge base to answer the top 80% of questions. Then, we hired our first support agent and gave them a detailed playbook (Standard Operating Procedures or SOPs). The playbook didn't just say 'answer tickets'; it showed exactly how to handle the 20 most common scenarios with template responses and escalation paths. It specified the tone of voice, the expected response time, and who to contact if they got stuck. Suddenly, 90% of support issues were handled without my input. This single system freed up 30-40 hours of my week. I replicated this across every function: marketing, development, and finance. You don't get to travel the world by working harder; you get there by building a machine that runs without you turning the crank. Your job as the founder-nomad is to be the architect of that machine, not a cog within it.

Your Business Model Dictates Your Freedom

Not all businesses are created equal when it comes to a nomadic lifestyle. The wrong model can chain you to a location just as effectively as a 9-to-5 job. The key is to choose a model with low operational drag, high-margin, and recurring revenue potential. Let's break it down.

Software as a Service (SaaS): This is the holy grail, and it's no accident that my main ventures like WebinarKit and Maker AI are SaaS products. You build it once, and sell it thousands of times. Revenue is recurring and predictable. The marginal cost of a new customer is near zero. Support can be systematized, and the product works for customers 24/7, regardless of your time zone. The challenge is the high upfront investment in development and the long road to profitability, but the freedom it provides is unmatched.

Digital Products & Content: This includes courses, ebooks (like my Sell More With Webinars book), and paid communities. Similar to SaaS, you create it once and can sell it infinitely. It's often easier and cheaper to get started than a full-blown SaaS. The downside is that revenue can be spiky, relying on launches unless you build powerful evergreen marketing funnels. My entire book launch was managed from abroad because the 'product' was digital and the marketing was systemized.

High-Ticket Services/Consulting: This can work, but you must productize your service. Instead of trading hours for dollars, you sell a specific outcome for a fixed price (e.g., 'Website in a Week' for $10k). This contains scope creep and frees you from the tyranny of the timesheet. The trap is taking on too many clients and ending up on calls at 3 AM. Be selective and charge a premium.

E-commerce/Physical Products: This is the hardest model for a nomad, in my opinion. Even with a 3PL (Third-Party Logistics) service, you're still dealing with supply chains, inventory management, customs, and returns. When a supplier messes up an order, or a container is stuck at a port, you need to deal with it. It introduces a physical-world complexity that is the enemy of a location-independent life.

The Non-Negotiable Tech Stack

Your tech stack is your digital headquarters. Skimping here is like building an office with a leaky roof. It will eventually cause a catastrophe. My stack has evolved over the years, but it's built on the principles of reliability, integration, and asynchronous capability. I don't chase shiny new tools; I stick with what works and what my team knows.

Communication: Slack is our virtual office. We have channels for everything: #general, #development, #marketing, #wins, and even #random for team bonding. The key is setting notification boundaries. It's for quick updates, not deep work.
Project Management: Asana is the brain of our operations. Every project, from a new feature launch for WebinarKit to a blog post for my personal site, starts as an Asana project with a clear owner, deadline, and detailed subtasks. A task that just says "update website" is useless. A good task is "Update /tools page: add new section for AI tools, include Maker AI and PressPitch AI with description and links, draft due EOD Wednesday". This clarity allows people to work autonomously.
Collaboration: Google Workspace is the foundation. Docs for SOPs and content, Sheets for financial tracking, and Drive for file storage. It's simple, universally understood, and just works.
Content & Marketing: I use my own tools heavily because I built them to solve my own problems. We use Maker AI to generate first drafts of blog posts, social media updates, and ad copy, which my team then refines. This has tripled our content output. PressPitch AI helps us automate our PR outreach. These tools are force multipliers.
Security: 1Password for managing hundreds of logins across the team. Non-negotiable. A good VPN (I use NordVPN) is also essential, especially when using public Wi-Fi in cafes or airports. It's basic digital hygiene.

The goal of your tech stack is to create a single source of truth for your entire company. When a new hire joins, their onboarding should be pointing them to the right tools and SOPs, not asking me questions. If your business depends on information stored only in your brain, you don't have a business; you have a job you can't quit.

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Building and Managing a Remote-First Team

You can't achieve location independence alone. You need a team, and learning to hire and manage remotely is a skill in itself. The biggest mistake founders make is trying to replicate an office environment online. Forget 9-to-5. Forget constant supervision. You have to build a culture of trust and autonomy from day one.

My hiring philosophy is simple: I hire for resourcefulness and communication skills above all else. During the interview process, I give candidates a small, paid test project with a deliberately vague instruction. I want to see if they ask clarifying questions, if they can figure things out on their own, and how they present the finished work. Someone who needs their hand held through a small task will be a massive drain in a remote setting. I'd rather hire a B+ developer who is an A+ communicator and problem-solver than an A+ coder who is a black box.

Once they're on board, it's all about setting clear expectations. We run on a system of KPIs (Key Performance Indicators) and asynchronous check-ins. For example, my support team has a KPI for first-response time and customer satisfaction. My marketing team has KPIs for lead generation and conversion rates. I don't care if they work at 10 AM or 10 PM, as long as they hit their numbers and communicate effectively. We use a simple daily stand-up in a dedicated Slack channel where everyone posts their top 3 priorities for the day and any roadblocks. This takes 5 minutes but provides total visibility across the company. It's about accountability, not control. This is how I've been able to build and scale multiple teams for my projects, from my full portfolio, to my live event brand Epic Marketing Events, and my SaaS companies.

Mastering Asynchronous Communication

If you want to run a business while traveling, 'asynchronous' needs to become your favorite word. It's a communication strategy where you send a message without expecting an immediate response. This is the only way to work effectively across multiple time zones without going insane. The default in many companies is synchronous: a Zoom call, a tap on the shoulder, an urgent Slack message. That's a trap for a nomad founder.

Instead of scheduling a call to explain a task, I record a 5-minute Loom video. I share my screen, walk through the exact steps, and articulate the desired outcome. The team member can watch it on their own time, re-watch it if needed, and all the context is there. This is 10x more efficient than a 30-minute meeting that requires coordinating schedules across a 12-hour time difference. A call that could have been a Loom is a cardinal sin in my company.

The same goes for project management. We treat every task in Asana like a self-contained briefing document. It includes all necessary background info, links to relevant files, a clear definition of 'done', and the deadline. The goal is that a developer in Ukraine or a marketer in the Philippines can pick up the task while I'm sleeping and complete it without needing to ask me a single question. This took years to perfect. Early on, I'd wake up to a dozen 'quick questions' that blocked my entire team. It forced me to be more disciplined in how I delegate and document. The burden is on the manager to provide clarity upfront. Mastering asynchronous work is the true superpower of a remote-first company.

Financial Plumbing for the Global Entrepreneur

This is where the dream meets the harsh reality of spreadsheets and wire transfers. Getting your financial infrastructure right is not sexy, but getting it wrong can kill your business and your travel lifestyle. You need to solve two problems: how to get paid by customers, and how to pay your team and yourself across borders.

For getting paid, Stripe is the gold standard. It's developer-friendly and recognized globally. However, fees can add up, and it's not available in every country. It's critical to research payment processors before you even decide on your corporate structure. I built a whole side project, ProcessingScoop, just to compare the labyrinth of options and fees because it's such a complex topic. You'll likely need a corporate entity in a Stripe-supported country, like a US LLC or C-Corp, to get access to the best financial tools. This is a foundational decision.

For paying my international team and moving money, Wise (formerly TransferWise) is an absolute game-changer. I can't overstate this. Traditional bank wires are slow, and they hit you with terrible exchange rates and hidden fees. Wise uses the mid-market rate and charges a small, transparent fee. I pay my developers in Eastern Europe and my virtual assistants in Southeast Asia through Wise every month. It's fast, cheap, and reliable. I also use it to transfer money from my US business bank account to my personal accounts abroad. It has saved me tens of thousands of dollars in fees over the years. Setting up multi-currency accounts within Wise is also a huge benefit for holding balances in EUR, GBP, etc., without getting crushed on conversion.

The Digital Nomad's Toolkit (Beyond the Laptop)

Your laptop and phone are the obvious essentials, but a few extra pieces of gear can make the difference between a productive work session and a frustrating nightmare. After years of trial and error, I've refined my 'mobile office' to a small set of high-impact items. This isn't about having the fanciest gear; it's about reliability and removing friction from your workday.

My philosophy is to invest heavily in anything that stands between you and your work. Good headphones aren't a luxury; they are a necessity for deep work in a noisy cafe. A portable monitor isn't just extra screen real estate; it's a 30% productivity boost when you're deep in code or spreadsheets. Here's a look at my core gear and some alternatives.

Travel-Tested Gear Comparison

Category	My Choice	Why I Use It	Alternative Option
Noise-Canceling Headphones	Bose QC Ultra Headphones	Unmatched noise cancellation for flights and cafes. Comfortable for all-day wear.	Sony WH-1000XM5
Portable Monitor	ASUS ZenScreen (MB16AC)	Lightweight, single USB-C cable for power and video. Doubles my screen space.	Lenovo ThinkVision M14
Portable Power	Anker 737 Power Bank	Massive 24,000mAh capacity with 140W output. Can charge my MacBook Pro.	Shargeek Storm2
Travel Adapter	EPICKA Universal Travel Adapter	Works everywhere, has multiple USB-A and USB-C ports to charge everything at once.	Anker 521 Charger (Nano Pro)
Connectivity	GlocalMe G4 Pro	Portable Wi-Fi hotspot with flexible data plans. A lifesaver when Airbnb Wi-Fi fails.	Using your phone's hotspot (can be expensive)

This setup fits into a single backpack and allows me to create a fully functional workspace anywhere in the world. The key is redundancy. I have backup power and backup internet. It's about anticipating points of failure. The one time your Airbnb Wi-Fi goes down during a critical product launch for a tool like PressPitch AI, you'll be glad you spent $150 on that portable hotspot.

Staying Productive and Avoiding Burnout

This is the part nobody likes to talk about. The Instagram posts show a laptop by the pool. They don't show the 3 AM anxiety about a server outage, the loneliness of eating dinner alone for the fifth night in a row, or the paralyzing burnout that comes from having no separation between work and life. The 'always on' nature of travel combined with the 'always on' nature of entrepreneurship is a dangerous cocktail.

My first year of trying this was a disaster. I had no routine. I'd work odd hours to match US time zones, sleep poorly, and feel constantly jet-lagged even when staying in one place. My productivity plummeted. I learned the hard way that you must create structure when none exists. My solution was to implement a strict 'batching' and 'time-blocking' schedule. I batch all my calls into two specific days a week, in a block of time that reasonably overlaps with my team's hours. The other three days are 'no-call zones' dedicated to deep work. I work from 8 AM to 1 PM local time, no matter where I am. This is non-negotiable deep work time. Afternoons are for exploring, errands, or hitting the gym. This separation is crucial. Without it, you feel like you're always working and never working, and both your business and your experience suffer.

I also aggressively seek out co-working spaces. While working from a cafe is fine for an hour, a proper co-working space provides reliable internet, ergonomic chairs, and most importantly, a community and a mental separation from your living space. The cost (usually $100-$300/month) is a high-ROI investment in your sanity and productivity.

Marketing and Sales from Anywhere

You can have the best systems and the most productive routine, but if you don't have a steady stream of new customers, you just have a very expensive hobby. Keeping the marketing and sales engine running while you're on the move is all about building evergreen systems. You can't rely on tactics that require your constant, real-time input.

For me, the foundation has always been content and automation. This is why I built WebinarKit in the first place. An automated webinar is a perfect nomad sales tool. It's a sales presentation that runs 24/7, educating potential customers and converting them into buyers while I'm on a plane or asleep. We drive traffic to these webinars using paid ads and SEO. It's a system that, once set up, generates leads and sales with minimal weekly oversight.

SEO is the other pillar. My blog is a long-term asset. We create ranking-grade content that attracts our ideal customers through search. It's a slow burn, but it creates a durable, defensible traffic source that isn't dependent on me actively 'posting' every day. We leverage my AI tool, Maker AI, to scale our content production, turning one idea into a blog post, a Twitter thread, and a newsletter, all managed by my team through our Asana content calendar. When I launched my book, Sell More With Webinars, we didn't do a massive, stressful live launch. We built an evergreen funnel around it, using the content from the book itself to attract buyers. Your marketing must be a machine that you build and oil, not a hamster wheel you have to run on.

Ready to Build Your Own Automated Sales Machine?

The single most powerful tool for selling digital products and software from anywhere in the world is an automated webinar. It's how I scaled my businesses without being tied to live launches. I built WebinarKit to be the simplest, most effective platform to do just that. Check it out and see how you can build your own sales machine.

Legal, Taxes, and Staying Compliant

This is the most boring section, and also the most important. Getting this wrong can result in massive fines, legal trouble, or being denied entry to a country. My advice is simple and absolute: hire professionals. Do not try to figure this out from a blog post (even this one). I can tell you what I've learned, but you must get advice tailored to your specific situation.

First, corporate structure. Most digital nomads operate through a legal entity, not as an individual. The most common structure is a US LLC, often based in a business-friendly state like Wyoming or Delaware. This provides liability protection and access to world-class financial tools like Stripe and US bank accounts. Setting this up is straightforward with services like Stripe Atlas or Firstbase.io.

Second, taxes. This is a minefield. Where do you pay taxes? The country where your company is registered? The country where you are a citizen? The country you're currently living in? The answer is... it's complicated. The rules vary wildly. Many nomads leverage the Foreign Earned Income Exclusion (FEIE) in the US, but it has strict requirements about how long you're out of the country. You need an accountant who specializes in expats and digital nomads. They are worth every penny. Trying to do this yourself is foolish.

Third, visas and residency. You are not a 'digital nomad' in the eyes of immigration officials. You are a tourist. Most people operate by entering a country on a tourist visa and working quietly on their laptop. This is a massive grey area. You are generally not allowed to 'work' on a tourist visa. This is becoming a bigger issue as countries crack down. More nations are introducing 'digital nomad visas', which are a great option if you qualify. Be aware of the rules. Overstaying a visa or getting caught working illegally can have serious consequences. Don't be reckless. My approach is to be discreet, follow the rules, and consult with immigration professionals when planning longer stays. You can find some of my trusted resources on my tools & resources page.

FAQ

How do you choose a good country to work from as an entrepreneur?

I look at four main factors: cost of living, internet reliability, time zone, and visa policy. A low cost of living buys you runway. Fast internet is non-negotiable. The time zone needs to have at least a few hours of overlap with your core team or customers. Finally, a simple and long-stay tourist visa or a dedicated digital nomad visa is crucial. Places like Portugal, Thailand, and Colombia are popular for good reason.

What's the best bank account for a traveling business owner?

Ideally, you want a combination. A business bank account in the country your company is registered in (e.g., Mercury or Brex for a US LLC). Then, a multi-currency account like Wise for sending/receiving different currencies cheaply. For personal use on the ground, a fee-free debit card like Schwab Bank's High Yield Investor Checking or a Revolut card is essential to avoid ATM fees.

How do you handle health insurance while traveling the world?

Standard travel insurance often doesn't cover you for long-term travel or in your home country. You need specific expat or digital nomad health insurance. I use and recommend SafetyWing. It's a monthly subscription designed for nomads, providing a global safety net for medical issues. It's affordable and gives me incredible peace of mind.

Should I tell my clients or customers that I am traveling?

For most of my businesses, like WebinarKit, customers have no idea where I am, nor should they care. The service just works. For my consulting or higher-touch engagements, I am transparent. I frame it as a positive, showing that I have the systems in place to deliver results from anywhere. Honesty is the best policy, but the context matters. The goal is for your location to be irrelevant to the quality of your work.

How do you deal with loneliness as a solo traveling founder?

It's a real issue. The key is to be proactive. I immediately join a co-working space to meet other professionals. I use Meetup.com to find groups with my hobbies (hiking, tech, etc.). I also schedule regular video calls with friends and family back home. You have to actively build a community in each new place; it won't just fall into your lap.

What happens when something goes critically wrong with the business?

It happens. I once had a major WebinarKit server go down while I was on a tiny island in Greece with spotty internet. The keys are: 1) Have systems in place. My tech lead had the authority and access to fix it. 2) Have redundant communication. I used my phone's hotspot to get online and coordinate in Slack. 3) Stay calm. Panic doesn't solve problems. Trust the systems and team you built.

Is a 'digital nomad' lifestyle sustainable long-term?

It depends on your definition. Constantly moving every few weeks is a recipe for burnout and is not sustainable for most. However, 'slow travel' - spending 3-6 months in one place - is very sustainable. It allows you to build a routine, a community, and truly get to know a place while still having the freedom to move. That's how I approach it today. It's less 'nomad', more 'global citizen'.

How can I see examples of the businesses you've built?

I'm an open book about my projects. You can see a full list of my active and past companies, from SaaS ventures like WebinarKit to media brands, on my portfolio page. It gives a good sense of the types of businesses that are well-suited for this lifestyle and how they fit together.

FAQ