Medina, 27, originally from the Philippines, and Howe, 31, originally from the UK, have been traveling together ever since.
"People are curious about how we fund our travels," says Medina. "If you're Asian traveling the world, it's not very common. If you go abroad, it's to work and not to travel - that's the mentality. But now some people assume that Jonathan has a pot of gold hiding somewhere, or a trust fund or something."
Howe has neither. Instead, the pair makes a point of continually developing skills that help them find work wherever they land next.
They document their adventures on their website, Two Monkeys Travel, and Instagram, @Kach2Monkeys.
Here, they explain how they afford it.