Finn O'Brien

Finn O'Brien

@demofinn

Fly cheap. Stay legal. Live anywhere.

Ex-Dublin accountant, full-time nomad since 2019. 54 countries on under $1,400 a month - I teach the flight hacks, visa strategy, and city playbooks that got me here, minus the mistakes that cost me a year.

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Doors to the August cohort of Runway open Monday, July 13 - 40 seats, and the last cohort sold out in 3 days. Everyone on the waitlist also gets a free seat at the Aug 14 live flight-deal workshop. Grab the free Flight Checklist below to join the list.

Why I teach this

In 2019 I was an accountant in Dublin with 23 vacation days and a spreadsheet of places I would visit 'someday'. I quit, made every expensive mistake available - overstayed a visa window by accident, paid 1,100 euro for a flight I later learned to get for 300, burned through my savings in month four - and then spent seven years turning those mistakes into systems. Fifty-four countries later, my average month costs less than my old Dublin rent. Here is what I believe: long-term travel is not a money problem, it is a skills problem. Flights, visas, and city choice are learnable skills with rules, tools, and repeatable routines. Everything on this page is something I personally use - the checklist I run before booking, the visa playbook built from 200+ border crossings, the launch sequence that gets you out the door in 90 days. No 'quit your job and follow your dreams' fluff. Just the mechanics, tested.

What travelers say

“I used the error-fare protocol from the Playbook and flew Dublin to Bangkok return for 211 euro. That one flight paid back everything I have ever bought from Finn, several times over.”

Sarah Keane · Graphic designer, Berlin

“The Schengen chapter saved me from a genuine mess. I recalculated my days, caught an overstay I was about to commit, and restructured two months around Croatia instead. Worth 100x the price.”

Marcus Feld · Software engineer, remote

“Took Runway in January, handed in my notice in March, landed in Lisbon in May. I live on 1,380 dollars a month all-in and my salary did not change.”

Priya Nair · Content strategist

Common questions

Is this only for 22-year-old backpackers with no responsibilities?+

No - the median student in my course is 33, and I have alumni in their 50s. Most people I work with have a remote or remote-able job, some savings, and a life they need to unwind carefully: leases, cars, partners, sometimes kids. The whole system is built around leaving well, not running away. Backpackers can afford to wing it; you probably cannot, which is exactly why the planning matters.

Do the flight tactics work from smaller airports?+

Yes, with one adjustment: the positioning flight. If your home airport is expensive, you price your long-haul from the nearest major hub (often 150-400 dollars cheaper) and add a short hop to get there. The Playbook covers how to do this safely - buffers, luggage rules, when to overnight in the hub. Alerts, error fares, and booking windows work identically everywhere.

How much money do I need before going nomad?+

My rule: three months of your target city's real monthly cost, plus your entry flight and first month's accommodation. For Chiang Mai that is roughly 4,500 dollars all-in; for Lisbon closer to 7,000. The first lesson of the course is building this number for your specific city with current data - most people overestimate the cost of living abroad and underestimate the cost of leaving badly.

What is your refund policy?+

Fourteen days, no questions, on every digital product and the course - if it is not useful, I do not want your money. Live calls can be rescheduled free up to 24 hours before, and the membership cancels anytime, effective at the end of the billing month.

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