People often ask me why I moved to Kauai, which usually warrants a short and generic response.
But someone asked me recently how I knew I made the right decision to move to Kauai.
The answer was simple, I knew beyond a shadow of a doubt when I first kissed Prajna, who is now my wife.
But before that moment, I had plenty of doubt and fear that I had made the wrong decision.
And that’s something I find happens with many decisions—we don’t know if we made the right decision until we’re far past it and we can look back at how it turned out.
The full story of why I really moved to Kauai is one that I haven’t told many people, but it’s time to share it…
It was February 2014, and we were still running things at Gigawatt, my company in Silicon Valley.
I was attending a business conference and I met this woman, let’s call her Sally. I had this intuitive sense that I was supposed to know her.
There was no attraction, it was simply a deep knowing that I was supposed to connect with her.
Upon connecting with her, she explained that she is a Medium—she connects with your Divine guides to share their guidance with you.
To that point in my life, I wasn’t into psychics or anything that I would’ve categorized as "woo-woo." I thought it was all just a bunch of BS.
But again, my intuition was driving the bus here.
She invited me to a group session she was doing that night.
So I went, and she made some really impactful insights and had some amazing messages for people in the group,
Which led me to schedule a one-on-one session.
I had no idea what to expect, but I figured "What the hell"…
One of the first things she told me was that I would be going on a great journey.
At that point, growth was stalling at Gigawatt, but I had this sense that the world of crowdfunding for non-profits was virtually untapped in South America, so I was thinking about making a trip there to expand our business.
So I blurted out, "Oh, yeah! I’ve been feeling called to South America to exp…."
"No…" she cut me off
"You will be going to Kauai, Hawaii."
I thought "What the hell is this lady talking about? I’ve never had any desire to go to Hawaii. Isn’t it just a bunch of tourists?"
She continued, "You are to go to Kauai and get your hands in the dirt. Get reconnected with the land, and disconnected from the world for a time."
She proceeded to share more about what would happen on Kauai, told me some things about my health, and shared that Gigawatt wasn’t going to last, that we’d be done in a couple of months.
I left the session a bit shellshocked. My head wanted to say that it was all a bunch of crap, but something inside me resisted that complete dismissal.
I mostly forgot about it and moved on.
A couple months later, in late April, my cofounders and I decided that we would shut down Gigawatt. It was a difficult decision, but I wouldn’t trade the experience for anything.
After a bit of soul searching, I was still feeling called to South America, so I decided that I would drive back to New Jersey from California, sell my truck, sell most of my stuff, put my life in a backpack and head down to Rio de Janeiro for the World Cup.
On July 1, I was on a plane to Rio.
The World Cup was an amazing experience. After spending two weeks in Rio through the end of the World Cup, I spent another couple of weeks backpacking south through Brazil and then spent six weeks through Argentina.
I was partying, meeting people from all over the world and enjoying myself. Life was good.
I was in Cordoba, Argentina and had just bought a motorcycle. My plan was to ride down to the Southern tip of Argentina to see Cape Horn, and then ride all the way up the West Coast of the continent.
I had never rode a motorcycle before, but my new friend in Cordoba was teaching me to ride and helping me with the paperwork.
I was getting the hang of it, but struggling a little. He was pushing me to ride the winding turns up into the mountains, and I had dumped the bike a couple times on those tough curves.
I had even begun mapping out a path to travel around the entire planet, as I felt my journey was to travel all around the world and share my experiences.
Then I got a message from Sally. I hadn’t heard from her since we met back in February, and it was now September.
"We need to talk. I don’t normally do this, but it’s a matter of life and death."
We got on the phone and she launched right in:
"Your team is very clear. If you continue on the path you’re on, you’ll be dead in two months."
In that moment, I had a flash of myself on the motorcycle and knew that’s how I would go.
At this point, I was lying on the floor of the apartment I was staying in, absolutely stunned.
"You’re getting the same message—you’re supposed to go to Kauai, find a place to live and work on a farm, give up drinking and partying and women, and reconnect with the Earth."
"The Silver Lining? She’s waiting for you there."
I knew that Sally meant my soulmate.
Deep down, my wanderlust had always been about finding my wife.
Deep down, I knew the message was right on, but my head was in tatters.
I was raised Roman Catholic, but had grown apart from it over the years.
However, I always appreciated finding beautiful churches in my travels.
A couple of days prior, I had found this beautiful church in Córdoba,
So after getting this message, I went first thing the next morning to pray.
The church was mostly empty as I dropped down into a pew and began asking God to give me a sign that this was real…
I must’ve sat there for hours, talking with God and trying to discern if I should actually listen to this guidance I was given.
At one point, I had my head down on the pew in front of me with my eyes closed for a while.
When I picked my head up, there was a guy sitting just a few pews in front of me,
And the shirt he was wearing said “Kauai Legends” on the back.
I might’ve let out a scream in the middle of the church because I was in such disbelief.
I scrambled for my phone and took a picture because I thought no one would ever believe me.
I wanted to yell to the heavens, "I GET IT! I HEAR YOU!"
The next week, I was on a plane to Kauai.
The day after arriving, I was walking around Kapaa town and saw a Yoga studio.
I had never been called to check out yoga before, but something in me wanted to check it out.
After the woman shared about their intro packages, she asked me "What’s your story?"
I told her that I had arrived the night before and that I was looking for a spot to live and work on a farm.
She responded, "My husband and I live on a farm and we need people! Let me connect you with the manager."
I couldn’t believe it.
The next day, I did a working interview on the farm, and that night, I was sleeping in my new home.
During my time on the farm, it felt like every woman I met, I’d have this sense of "Is that Her?!," only to be disappointed.
After almost a year on the farm, I got connected with an inventor that was looking to do a crowdfunding campaign.
On the day we launched the campaign and were showcasing the product at an event in Hanalei, I met a woman and we connected deeply.
She mentioned, "I have to introduce you guys to my business partner."
A couple of days later, I met her business partner, Prajna.
After connecting, we met another time to learn more about each other’s businesses, only to have our conversations come back to family and life.
Then another business meeting was a hike…
Then a day at the beach…
And then, I kissed her.
And in that moment, I knew.
I knew it had all been worth it.
I knew I had made the right decision.
And I knew I would spend the rest of my life with her…
So, you see, this is why I don’t normally share the entire story of how I ended up on Kauai, because it’s a long one!
But I hope you enjoyed reading it as much as I enjoy sharing it.
Remember, we often don’t know if we made the right decision until long after the decision is made.
For me, that was over a year later...
PS - If you know anyone looking to buy a motorcycle in Cordoba, Argentina, let me know. I still own one there 🤣