What Matters?

A Homecoming Story

The winter of 2003 was a particularly cold one in New York City. 20” of snow fell on Central Park. In one night! It was December, exam time. From a small, warm town in the south, I was not having it. Procrastinating studying as per usual, I remember lying on my bed, looking at the classic dorm room tropical island photo.

“Effff this,” I literally said out loud, “I’m going there!” I spent the rest of the week planning my exit.

I was a freshman at Columbia. I’d just graduated valedictorian of a fancy boarding school I’d attended on financial aid — I’d played soccer and tennis in the state finals, sat first chair classical sax, had a profitable photography business, traveled the world on its earnings, learned a handful of languages, and won nearly every department award upon graduation. I wrote my ticket into whichever Ivy I wanted. The world was my oyster.

But no, not like this.

I scheduled a meeting with my guidance counselor for the Monday after exams.

I walked into her office, smiling ear to ear…“I’m going to take next year off and…”

She interrupted, “you can’t do that…”

“Oh yes I can ☺️,” I replied, “shall we discuss the terms 😉?”

Apparently I had to drop out. So I did. Right then. Right there. Didn’t think twice.

I was going places!

I was going to be a surf bum in Central America!

My high school Spanish teacher was a local from the country where I wanted to go. Her brother had spent six months at our boarding school learning English during my senior year. He and I got into a lot of trouble together 🙃.

He was my first email. He’d pick me up from the airport. I had a one-way plane ticket.

I landed in May of 2004, spent a week with him in the city. I found a beater 1984 Chevy Blazer for $700 in the classifieds — 4-speed, busted a/c and tape deck, dark blue with accents of rust. The seller was friends with the owner of a fancy 5-star hotel on the surf beach where I wanted to go. I got a job waiting tables there, touting that boarding school experience 🤣 (I only dropped two bottles on my first day!).

I was surfing every morning, making friends, partying at night. Not a bad life.

I’m pretty chatty in the water (kinda taboo amongst hardcore surfers…p sure they forgot the point of all this is to have some fun 🤪!) and struck up a conversation with the best local in the lineup. I mentioned I was looking for somewhere to live. He was looking for a roommate. Rent would be $90/month.

After a couple months of living with Pindeco, he asked me if I’d ever been down south. I hadn’t!

“Vamonos,” he said…”te enseño mi pueblito,” “let’s go…I’ll show you where I’m from.”

After a 2-day drive through the coastal jungle, followed by a couple hours in a boat, we made it to a remote corner of the world that shall remain nameless. We hiked up a hill to the most beautiful piece of nature I’ve still ever beheld. It was love at first sight. There were a few huts overlooking the ocean and an island in the distance. Humpbacks were breaching. Not a person in sight.

Every morning Pindeco, his friend Sandro, Guille (son of the owner), Mario (Guille’s friend), and I hiked down through the jungle to a rivermouth that fed an awesome lefthand point break. And surfed alone. All day.

Piña coladas over sunset. A candle after dark. Falling asleep smiling before it burnt out.

At dawn, the monkeys would howl to let us know it was time to get up and do it all over again!

Paradise.

I pulled the owner of the hotel aside after a week. I offered to translate for the ocassional (mostly European) tourist — I could speak English, Spanish, French, Portuguese, a little Italian. I’d cook, I’d clean, whatever it took. Could I pretty please with sugar on top do that in exchange for a room and food!?

He smiled.

I drove Pindeco north, got my things, and headed back.

Guille, Sandro, Mario, and I shared a room with 4 small beds. We mostly surfed and laughed, made up silly games, and laid around under the tin roof during the afternoon rains. We’d work the restaurant during meal times, carry guests’ luggage up the hill, take them through the park on tours, Sandro making use of the four English words he knew best, “you knowwww…tucan…it’s like…tucan!” Even though it was so long ago, memories from this time are crystal clear. Many times I had the thought, “I could die happy now.”

A few months later I ventured back to “civilization” for the first time — the closest town, where at best a few hundred people lived. A cute waitress at a local restaurant caught my attention, super cool, smart. Rebecca was her name. I started coming up with more and more excuses to head into town. She had this funny way of talking about nearly everything that always made me laugh. And she fed me! Lots! It was a family restaurant, the home attached. Eventually I left the hotel and moved in with her. Helping Rebecca and her mom and sisters in the restaurant, still carving out plenty of time to surf, of course! One of my favorite memories was making Christmas tamales as a family. It was such a warm, loving household. The central gathering place of the town.

But then surfing one day, I paddled out next to this leather-skinned white guy, sun-bleached hair. The waves were so perfect. The view majestic. And this guy was miserable.

“Shiiiit, I don’t wanna be thaaat guy.”

I paddled in, re-applied to school, and bought a plane-ticket.

I cried when I unpacked my things that next January in New York. I’d been gone 9 months. There was just so much I didn’t need. And it was worth more than what all my friends back in the jungle owned, combined. What am I doing? Why am I here?

Little by little, I forgot…and fell back into “the swing of things” <- civilization

I didn’t hate it all, at the time. I loved computer science. I got some amazing internships. I partied. A LOT. I got 26 job offers before Christmas of my senior year. By civilized standards, I “had it all”.

But na, not really…so…road trip! Summer of 2007. NYC to Panama. With an amazing girlfriend I’d met the summer before (Latin American, of course). More surfing, more jungle. ALL the food. Asking locals from town to town for directions.

We made it back to Austin after a few months on the road and settled back into…the grind. I lasted 11 months at a big company before I was ready to eject. Joined a small startup this time. After winning the Genius Grant there for building something that helped them go public, back to the beach — Australia and Indonesia…for a year!

My super “successful” uncle wrote me an email telling me I “was throwing [my] life away for the veritable beach towel.” Now I knew I was on the right track!

I liked Australia but didn’t love it. Same for Indo. I missed Latin America. I’d spent my first summer there when I was 15.

It was the first, and really only, place I’ve ever felt welcome, like I belong, safe, loved, wanted. Rebecca was always convinced they’d confused me at birth in the hospital, certain I had “sangre latina”, Latin blood.

Hmmm, what if I could find a tech company in Austin that would pay me well, and I’d spend most of my time on a beach in Mexico!? Recruiters had gotten word I was back on the market, and the emails came pouring in. I had a canned response describing what I was looking for. I didn’t hear back from most, shocker! Until one day, I got my first nibble. He invited me to coffee.

Marc Davis was smiling ear to ear when we met.

“So, do you have something…” I eventually asked.

“Nope!” he was now full on laughing, “but I just had to meet the guy who wrote this email 😂!”

We had a good chuckle and later said our farewells. Cool dude, I was glad to have met him. Running recruiting for Trilogy, there’s a reasonable argument he’s responsible for a solid chunk of the tech talent that’s made its way to Austin over the years.

And then a couple weeks later he called me out of the blue, “you know what, Andy, if there’s one person who’ll hire you, it’s Chris Taylor.” He put us in touch (and surely got a nice commission)!

Chris was one of the early guys at Trilogy, too. He had branched off on his own to live a more relaxed life. He hired me to lead product at his 8-person startup that’d been coasting along profitably for years.

Working less than 30-hour weeks, making ~$200K a year, I spent 3 months of my first year out of the country (mostly in Mexico), surfing duh!

And after a couple years of that, nope, still not it.

It was time to try my own thing.

Chris smiled when I gave a 3-month notice, “We were taking bets on how long it’d be before this happened. We both know you belong on my side of the table, tell you what, why don’t you hang out around here as long as you want, get your venture off the ground, I’ll show you the ropes in the meantime?”

Yeah, he’s just that kinda guy 🤌🏻

Mike DeBonis gave a warm send-off in front of the company when it was time, “we can’t wait to read about you in TechCrunch!”

Also that kinda guy 👌🏻

While this wasn’t “it” for me, I was definitely getting warmer. Surrounding myself with better people, enjoying what I did more, working fewer hours, producing better deliverables, and still surfing!

So I did it, started my own thing. With some friends. We had a great idea. It helped people. We had a lot of fun. And I’m proud to say I made good on Mike’s wish.

But my motivation was wrong ⁠— it was mostly about filling out a lottery ticket. I burned out. I just wanted to get back to paradise, for good. I kind of resented it. Thanks for that “fierce conversation” Nils Marchand.

And so, not so surprisingly, it all fell apart in a span of just 3 months in 2017. My new wife was having an affair, my biggest investor filed a frivolous lawsuit to kill a big acquisition, a family member threatened me until I paid them every penny to my name.

Woof.

“Okay Universe, I’m listening! Not like this, either, hey?”

My grandad had taught me to meditate as a kid. I fell back into my practice. I surfed. I cried. I laughed. I screamed.

It was a tough year.

Eventually I took care of the lawsuit and exited the business on December 27, 2019…for orders of magnitude less than the earlier opportunity. I had a meditation retreat on December 28 I’d decided I wouldn’t miss for the world. And I wasn’t willing to operate the company after 2019. I was done.

The next 5 years were mostly healing. 7 months of meditation retreat. Dozens of Ayahuasca ceremonies. A year living alone in the woods. All kinds of therapy. Getting certifications to teach yoga, teach meditation, and coach. At first the motivation was to help myself. Then I started to realize people were asking me more about this stuff than tech. And I was helping them more. And liking it more. How cool that a part of my personal journey could be helping others with similar stuff (broadly speaking, shifting from living in fear to love) which in turn helps me more which helps them more and so on.

A lot of my crap had crystallized in early childhood; I’d been seeing therapists most of my life for it. Apparently, I was finally ready to begin to make meaningful change in 2020. The pandemic was supportive for that.

About 2 years ago I hit rock bottom (I hope 🤪). I wasn’t sure why I wanted to live. I did want to live, though, I knew that. I’m grateful I had the tools, resources, and support to navigate this phase.

Slowly, I started noticing sparks ⁠— a smile from a stranger at the grocery store, a star twinkling, the sun hitting the river, Barkley’s gaze, a random chat with a friend. These things made it all start to feel more worth it. With practice, I internalized these sparks and started noticing them within.

And then last summer, I stumbled into a retreat that brought me back south of the border. The retreat was…fine. But whoa, that feeling as I got back on my surfboard, hanging out with the locals, in the tropics…I started to re-member!

And just like that, as soon as I’d engage with the folks on the retreat, tension.

“Oh my god, I can do this now…I can come back…for good this time. All I need is an internet connection a couple days a week for clients” <- thanks Elon 🤦🏻

My thesis was that down here my nervous system would be stable and regulated enough to make the more meaningful change I’m now ready for. Something happens when I’m speaking, thinking in Spanish, so much of the trauma is just…not there 🤷🏻. Makes sense when you think about it.

And I was right.

I bounced around for the last 4 months searching for a place to call home, more easefully navigating difficulties, until this Tuesday, when I found myself back where it all started…reunited with Sandro at the hotel in paradise from 22 years ago, surfing the same river mouth all to ourselves, joking around like it was all just yesterday. I’d nearly forgotten about it and had just kept following my body, pulling me south over all these years. It was like pure magic how it all came together. And it most certainly did not come from thinking hard about it! To the contrary. Mostly practice, play, listening to my gut, saying ‘no’ to the inner critic telling me all the reasons this was a bad idea.

Oh crap! Only an hour until my first client meeting…I was an hour into the jungle, then a drive to get back to “civilization”.

When I remembered, “wait, wonder if they have internet at the hotel now…”

Of course they do!

I took client meetings from the deck of the room I’d lived in all those years before, Sandro hanging out by the bar.

On the walk home he and I reflected on how…even though we’d split ways over two decades before, me doing what I did, him continuing to guide tours in the nearby national park everyday…how nearly identical our world views always were and still are. We suffered similar wounds as kids, find peace in nature and in other sensitive and strong people, and are constantly continuing to choose the light. I want to learn which fruits he’s always picking up to offer me, how to see the animals and flowers he shows me on the regular. He wants to learn my world of working online, marketing (lol as if I knew anything about that 🤷🏻), as a coach 💫.

“Yo sabía que ibas a seguir siendo la misma persona, Andy”...“I knew you’d still be the same person” ☺️.

“Tú también,” I smiled, “you too.”

In some ways everything had changed. In more ways, nothing had.

Never in my wildest dreams could I have scripted feeling so complete as I do right now.

The naturaleza, the surf, the vibe, my long lost friends, helping people, earning what I need to live. The whole package.

If there’s an “it” out there, I’m p sure this is “it”...for me anyway…for now 😊

The obvious shadow in my life has been bouncing around, inability to settle. Some of that is great, brings growth. Some is running. But I’m pretty sure I’d just been trying to get back home this whole time. And now I am. I know it. I always knew. Just needed to learn some things and move through some crap to get back here.

Whatever is happening now, I’m definitely not fighting it anymore. I’m enjoying it. And I’m ready for what’s to come!

And even though some parts of this all have been a real cluster, I wouldn’t change a damned thing!

What about you? What’s your dream? Let your imagination run WILD! I help folks do in a year what took me a decade. 3 years and you can have it all! Drop me a line if you’d like some support 😊.