I actually stumbled upon this podcast a couple of weeks ago when he just had about 15 episodes out and it's really motivating to listen to because I've been having the same plans (apart from the sailing) of going solo instead of staying employed forever. I'll definitely tackle this within the next quarter.
Unfortunately I never got to work with Tiago or Mathias during my stint at trivago but it's cool to hear what they're up to. :)