This transcript was generated from the episode audio and may contain minor errors.
[Music]
Personalized travel itineraries for digital nomads. Welcome friends. Welcome to Side Hustle School. Welcome to Throwback Thursday, where we take an in-depth look at someone whose story has evolved since we first featured them. Now, last week we heard from a micro brewery tour guide in Chicago who turned their passion for craft beer into a hands-on business.
Today, we're gonna go from Chicago to Lisbon. We're gonna hear specifically from a travel lover who begins crafting personalized itineraries for remote workers, remote workers, other digital nomads, people who are out and about in the world. This travel lover helps them find co-working gyms and local culture and is able to earn pretty good income for themselves. I love that. Being helpful, being useful, finding a way to get paid for it, that seems pretty good to me.
Again, personalized travel itineraries, that's today's focus. Let's hear directly from Finn. He is our case study. He's originally from the UK, but is now living in Portugal. Gonna pass the microphone to Finn.
[Music]
I'm Finn, a travel-obsessed expat who moved from the UK to Lisbon a few years ago. I fell in love with this city's balance of old world charm and modern energy. And I noticed a trend. Digital nomads were flocking here in search of affordable living, solid wifi, and a cultural scene beyond generic tourist traps. Many of them had no idea where to find the best co-working spots, which neighborhoods had budget-friendly short-term rentals, or where to grab an authentic meal.
I realized I could solve these problems with tailored travel itineraries, focused on exactly what remote workers need. I began by making a few free sample itineraries for friends, like a remote designer from Berlin and a freelance writer from Vancouver, who were each planning to spend a month in Lisbon. I highlighted reliable co-working cafes, noted which apartment blocks offered monthly leases, and included a list of local events where they could meet like-minded professionals. My friends loved the concept and raved about it. Next, I created a landing page featuring a short questionnaire, preferred neighborhood vibe, budget, dietary preferences, and interests beyond work.
For 75 euros, I had to deliver a personalized PDF, packed with accommodation leads, a curated list of working spots, weekend excursion ideas, and cultural events. In the first month, I sold 10 itineraries, mostly to friends of friends, making about 750 euros. Well, not bad for something that had cost me nothing but my own time and local know-how. To reach more digital nomads, I posted in Facebook groups and subreddits dedicated to remote work. I offered a Lisbon Starter Pack discount, 60 euros for the first five people who booked.
They snagged the deal, left glowing feedback, and I raised the price to 100 euros. By the end of the month, I hit my first 1,000 euros in profit. I realized I could scale this beyond Lisbon. Some clients asked if I knew other European hubs. I didn't know Barcelona as intimately, but I didn't know a local who could help.
We agreed on a small referral fee, and suddenly, I was offering Lisbon plus Barcelona digital nomad packages. Each package sold for 150 euros and included itineraries for both cities. This cross-city approach encouraged repeat customers who wanted to hop between remote work hotspots. With more sales rolling in, I started adding small upsells, like a weekly itinerary refresh for an extra 30 euros, or introductions to local freelancers who knew the scene. I kept it simple, focusing on what people actually needed, and some of them worked better than others.
Now I'm averaging about 1,500 euros a month. Well, it's still a side hustle, but it feels like a real business, one rooted in my personal experiences as an expat who understands what digital nomads crave in a new city. Occasionally, I get odd requests, like someone asking where to meet other digital nomads who only drink tea after 6 p.m. Surprisingly, I managed to find them a Tuesday night meetup in a quiet cafe. It's not glamorous, but it's profitable, practical, and a lot more fun than sticking to tired old travel guides.
[Music]
Hey, Finn, thank you for sharing these updates. Definitely seems like the kind of hustle that once it's set up, you can continue to earn from it for maybe not forever, but at least for a long time. And maybe that's a good point about sustainability. I haven't said this in a while. Sometimes people are like, hey, is this side hustle scalable?
Is it going to last forever? And the answer is often no and no, but that's okay. Like it doesn't have to last forever. Do you work at the same job forever for your entire life? No, people make changes.
So the same is true for businesses and side hustles. You can do something for a while and it earns money and that's great. And maybe three years from now, you'll be doing something else, but you've earned that money in the meantime. You've had that experience. You've been able to make something helpful.
So I think it's okay to think about projects in terms of a limited lifespan. Listeners, thank you for being out there. We've got so much more coming up. If you've got a question or an update about your hustle and you know where to go, sidehustleschool.com. There are notes pages for every episode, free resources and more.
And of course, more is coming up. For now though, I'm signing off. My name's Chris Guillebeau. You're listening to "Side Hustle School." [Music]
from The Onward Project.
