Notes on being Different

Today I had a fun chat with Dave Lukas, the curator of the Misfit Entrepreneur podcast, to see if I would be a good fit for his podcast (turns out that I am because we scheduled one - stay tuned!) and we got to talking about the theme of his show that I really resonate with - essentially the idea that all Entrepreneurs are Misfits or in maybe more likeable terms - different. We are out of the box thinkers and people who see the world at a unique angle or viewpoint and find inspiration in that space between.

Sure I think a lot of people are born a little more ballsy or with a larger appetite for risk, and yet I think too commonly people think that if they aren’t just "that way", then they never will be. I believe it’s a spectrum and so much of that business chutzpah can be learned, encouraged, and molded into a person if that is something they are wanting for themselves.

On the flip side, as someone who always had that “Misfit” quality deep in their bones, I can attest to how difficult that “gift” can be most of the time. With just a seconds thought, I can bring to mind 3 specific times in my life where my audacious quality left me so far outside the traditional circle, that it was uncomfortable.

The first real nail biter for me was when I decided to drop out of High School and pursue a GED instead. Let me set the scene. Right before I started High School, my father had the bright idea to move the family from Maui to Miami to be closer to his first son, my half brother, and his kids. We moved and I started at a massive school that offered an Ivy League education compared to what was available in little, sleepy, ‘ole Wailuku. Unfortunately, 2011 rolled around, the Twin Towers fell, and my family felt like they wanted to return to the quiet safety of slow paced island living. So I was ripped away from my mega school and friend group there and was plopped back into the State of Hawaii Education system. Let me tell you, it left a lot to be desired.

At the time, I was a Sophomore, 15 years old, and entering a new school mid-year. I enrolled in some Honors classes, but found myself bored and wanting more. I don’t exactly remember how I found out that a GED was even an option and bless my mom for always being my cheerleader, but once the idea was in my head, I ran away with it. I did all the research, found out what was required and where the prep classes for the test could be taken, got myself set up for the exam and even looked into how soon I could start up at the local community college. My oh my, was I naive about the shitstorm that was about to rain down on myself and my poor mother at the announcement of this decision.

Despite all the concerned looks and all the jive spoken by the haters, saying that I would be a “dropout” and would never go to college, I tested in the top 5 percentile in the country and enrolled in the Winter semester at Maui Community College, becoming one of the lead students in my classes there. It was such a joy to be in the more free-form education system that college provided and to be excelling when everyone expected (or wanted) me to fail.

The second time was when I decided to start using Airbnb. I was in Massage School at the time and had two close friends in the program whom I always sat with, confided and chatted with so I naturally shared that I was considering trying it out and upon deciding, that I was actually going to move forward with it. Both of them were older than me and had major reservations/hesitations around it and with good reason, but that little voice inside me had me press on, and despite some minor setbacks, it helped me climb the mountain to where I’m at now.*

The third time of likely many of these examples, was when I decided to buy a home in St. Louis to use as an Airbnb rental. I had only been to St. Louis once, for about a day and a half, was committing to purchasing the home sight unseen, and it was only the second home I had ever bought, but that strong intuitive guidance to march to my own drummer sang louder than the naysayers, so onward I moved until it was mine. And although my mother had passed, my sister stepped in when I a had a moment of second guessing myself, below is a facebook post about what she told me.**


The conversation with Dave today brought to mind a Vox (an audio clip, from the walkie talkie app Voxer) I had sent to my friend last week. In it I was sharing about an reading I received from some close friends of mine who are Astrology Wizards, that they gifted to me in a critical turning point in my life (right after my mom passed away). One of the major takeaways (of which there were many) was the grounded knowledge that thinking, acting, and just being different was a core thread of who I am and didn’t make me bad or wrong.

So if you ever feel different see if there are ways in which you can embrace that. It’s definitely a little tougher when you are still living with parents and you are expected to conform to the general society norms or their rules, but trust me, you will have your time. And if you are looking for ways to nurture your entrepreneurial edge and branch out more, send me a message. I am training up people to become co-hosts and house managers all over the country, to learn to create their own businesses like mine.


*I made the paragraph about my journey with Airbnb short, as I am preparing a blog post with an in depth look into how I got started with Airbnb. Keep on the lookout for that, it will likely be the next one I post.

**I will also write a longer post about the acquisition of my second home. Lots to come.  


  • Create your Airbnb listing today (We earn a referral bonus for up to 5 new listings per profile)

  • Track your Net Worth (get $sign up, it’s free!)”20 when you