Hi, I’m Aaron.

I’m a serial entrepreneur. I founded and sold a digital agency, led product development for a Tokyo-based software company, and built digital experiences for NBCUniversal, Condé Nast, and Coca-Cola. These days I invest in projects in Costa Rica — and explore its parks, beaches, and mountains with my rescue dog, Chase.

Get in touch More about me  →
Aaron Bailey in Iceland
Me chasing waterfalls in Iceland.

My life in Photos.

More on the blog  →
Chase’s first waterfall hike in the mud. He had no problem with the slippery path but he almost caused me to fall a few times with his excitement.

2026-04-02

This goofball has brought so much joy, a ton of chaos and even more hair into my life.

2026-03-11

I’m grateful for this quiet life I’ve built. Even the dirty puppy.

2025-11-28

I always love visiting the kids in Wisconsin but it was extra special to be part of the first communion of the second godson. I’ve been blessed to know Sam from birth and am impressed by the human he’s turning out to be.

2025-05-06

This is 48. 47 was a quiet year. I invested in friendships and myself and my businesses. I suspect the fruits of this past year will take years to bear. I’m feeling my age. I’m no longer as spry as I used to be. The gray hair is more pronounced. The years ahead both bring some dread but also some curiosity. I wonder who I’ll be in my 50s. 48 will be more of the same. Continuing to learn how to better love myself, my adopted Costa Rica and the greater Universe that continues to amaze me at every turn. My intention for 48, paraphrasing Rumí: Stop acting so small. You are the Universe in motion.

2025-01-04

POV: when you grow up on a seed corn farm in the 80s.

2023-11-14

45 was about finding peace. 46 is about seeing this incredible world through a fresh perspective. It’s about loved ones. And one loved one! It’s about continuing to orient myself towards peace… …and finding joy in the small, mundane things like walks around the park. It’s about reading glasses (seriously?!) and more gray hairs. It’s about the jungle and the beach and missing the corn fields, but not the snow. It’s about stuttering my way through a new language and being called “Aarón” more often than “Aaron.” It’s about starting new things, and clearing out the old. And it’s about wondering in gratitude, “how the heck did I end up here?”

2023-01-04

A great quick hike up Cerro Pelado this morning. I’m really happy I have @saltamontico to take me to places like this.

2022-12-27

Happy solstice.

2022-12-21

“Beginnings always hide themselves in ends.” — @mikeposner Three years ago this week, I came home to learn my five-year relationship was over. I was devastated, in shock, unable to feel anything. Not knowing what to do, I hopped on a plane to Wisconsin and sought solace with dear friends who graciously invited me to spend Christmas and New Years with them in Costa Rica. That trip led to another trip which led to buying a vacation home which led to me moving to Costa Rica earlier this year. Now I’m investing in a business in Costa Rica and dreaming about producing a couple of TV/movie projects here – all with a dear friend. I am surrounded by friends, love and a beautiful (yet still messy) life. If you would have asked me on that painful day where I’d be on November 29, 2022, I wouldn’t have been able to dream of the love-filled place I am today. (And I certainly wouldn't have predicted the difficulties of grieving and healing during a pandemic!) Had I not visited those Wisconsin friends or agreed to go on that first trip to Costa Rica, who knows where I'd be? Sure, it might be just as beautiful, but I'm happy this is my new beginning. (Cross posted from https://aaronbailey.com/beginnings)

2022-11-30

Working on something cool? Let’s connect.

Get in touch →