Posts tagged entrepreneur
Shark Tank Auditions Part Three - The Evolution Of Expectations


On Wednesday May 1st I will be making my 3rd attempt at landing a spot on the popular TV show Shark Tank. The first time I auditioned was in 2015 the first year of our company. I was fresh out the gate with this luggage storage disruptor idea with billion dollar expectations. Oh how the times have changed. Now you can find me panhandling on the street for money. Despite the cold harsh reality of what it actually means to be an entrepreneur tightening its icy grip around my dreams, the pursuit continues. However just so you know, I am not doing this because I want (all though I can use) funding (as you can see by my blog post Why Should Billionaires Have All The Fun? ). Instead I am doing this audition as a way to measure my personal and professional growth. Let me explain…


In my last audition I was but a step away from making it to the show taping in L.A. After my initial application submission on the Shark Tank website, I received an invite to audition in person at a private venue for diverse entrepreneurs (which I am doing again this Wednesday). I was fortunate enough to make it past this first hurdle and within a week recieved a call from one of the show producers asking me to submit a video audition tape, (which you can see on our YouTube Channel. ) This would be followed by an email from that producer…

Once delivery of your submission, it's usually about two weeks or so that the producers will reach out if they're interested in moving forward with you.

For me this was two weeks of constantly checking my emails (“does this thing work?”), reaching out to previous show contestants (“how quickly did it take for them to call you back?”), and even sending follow up emails to the producers (“Did you get my video link?”)

I was a mess.


In each of my previous auditions I had delusions of grandeur of making it on the show so that I could prove all my doubters wrong. This included my ex’s, my family and friends, my competitors, people who ignored or rejected me, even people who didn’t celebrate or encourage me at a level that I thought was sufficient for my efforts. I had a Michael Jordan-like drive to make enemies even where they were none if it gave me even the slightest edge. It was all about look at Me! Me! Me! See how I made it!


There is something about building a business that humbles you. It is survival of the fittest (state of mind). It weeds out unnecessary baggage, trashes all your hangups, and purges the extraneous and unnecessary. Despite what I thought I knew about entrepreneurship through pop-culture (Steve Jobs/Bill Gates/The old Robber Barons/go down the list), my reality was much different than the myth. It seemed to me that it was more likely that if you were fortunate enough succeed in business, that it was in spite of your baggage not because of it. Vanity, pride, fear, self loathing, selfishness had no place in my business, I needed to not only survive, I needed to grow. I haven’t had the fortune of having kids yet, but I imagine that it has a similar effect on ones growth. If growing your business is what is important, then trivial matters fade into the background. This has been my experience.


Now that I have auditioned twice before over the lifetime of my company, looking back at the trajectory of my growth from the first audition (where I was convinced that Free Your Arms was destined to be the next Airbnb), to today’s version of Free Your Arms (as a company that connects with each neighborhood, each shop owner, each customer, as if it was our only neighborhood, customer, shop owner).

I have “grown” from having dreams of global domination, to bringing a small town community based approach to the big city.

Here is an excerpt from one of the early versions of the business plan for our relaunch this past February. It cites the experience of my parents “Clyde and Dallis” (immigrants from Trinidad and Tobago to New York City (Where they had me), to now living in a small town in Florida called Spring Hill) as an example of what we lost in big cities and with technology. (At the time The Shop was called “Our Small Town”)

Decades before Airbnb or UBER, Clyde and Dallis were always happy hosts
to anyone in need of a room or a ride. From family visiting or migrating to NYC, to the troubled children of friends and family, to students studying abroad. There was always someone in that extra room. And those visitors had to look no further than Clyde's Yellow Cab for a ride to or from Church, work, the airports, you name it. And yes sometimes guests or passengers would offer payments as compensation for time or fuel, but always there was something beyond the monetary exchange that made this less a transactional experience and more a communal one. In return guests would help with the cooking, the cleaning, the yard work, picking up groceries, or just contributing to the daily dialogue that formed the fabric of their home and community.

As time has passed this organic support system has slowly been replaced by a digital one. Now if you need a ride you call an UBER, when you need a place to stay you find an AIRBNB, when you need items picked up from the grocery you use POSTMATES. All great services that have made most of our lives easier, but for the Clyde's and Dallis' of the world, they are finding themselves increasingly isolated as that old support system erodes around them.

OURSMALLTOWN restores that old support system and provides communities on the fringes of technology with the tools that help them bridge the digital divide, transforming what was a purely a digital exchange into a more communal one.

Some might look at this downshift in expectations as a step backwards, I don’t. I know that if I am doing something (for the right reasons) that matters that it will connect with even the toughest critics (or judges in this case). This audition is just another hurdle to gauge that growth.





Pay It Forward Friday Profiles - Julius The Genius


In my quest to find inspiration for my own entrepreneurial pursuits, last Sunday while doing deliveries, I ran across a charismatic entrepreneur who was counting more cash on hand than I had made that entire week. I am not sure what it was, maybe it was the way he was counting the bills in broad daylight in a carefree manner, but he struck me as an individual that marched to the beat of a different drum. Determined to gain some insight into his genius I pulled alongside him while still sitting in traffic and gestured for him to approach my vehicle. I then asked him if I could do a quick interview - he said yes.

As I pulled in to park and started to set up my camera - he approached, suddenly launched into a high kick that would make a Radio City Rocket Blush, and before I could fully gather myself he started my interview for me - “Now what you wanna talk about?” he said. Seemingly eager to get back to his days work.

I asked him his name. “My name is Julius, I was born on a leap year “ - he proudly proclaimed, even showing me his Identification as proof. My hunch was right… Julius was a showman with a Phineas T. Barnum like flare. So I cut straight to my question. What is your genius?

— Julius The Genius

This answer was more Master Po than Gary V - Surely there must be more to his genius than that. I listened on like a patient young grasshopper as he continued… Julius went on to explain that no matter the religion we all serve one god. He then asked me if I wanted to hear a song?

Yes I said.

Julius started

I learned how to live, and depend on jesus,
I found out if I did, we will survive.

And then another

I’m comin' up on the rough side of the mountain,
I’m doin' my best to make it in.

Great voice I thought. And there is a theme of survival that I immediately picked up on. After all the tagline of this series is Survival Tales of a Founder. It was then I noticed something else - It was not me who was engaging Julius, instead it was Julius who was engaging me. Was this show one big MacgGuffin? Was I being wooed? It seemed like Julius was courting me like a Paradise Bird doing a mating dance. So is this his genius? He puts on a show, his mark (me in this case) drops their guard, and he goes in for the close. After all who could say no to that voice. As I stated in the article that launched this series.


You might call this a street hustle and it probably is. Or you might call him a panhandler and you might be right. Some might even use a less flattering description for this pitch. However you label him I see the same entrepreneurial drive in Julius that I see in myself. And amongst his competitors I could see that he was not employing the same tricks I have come accustomed to and even employed myself . What Julius did was he sized me up (What we in sales call qualifying), lured me in without me knowing (What some call a soft pitch), put on a show (The presentation), and led me to his close (which he had not yet accomplished - read on). These are all skills I have been employing on my own daily pitches (which I am documenting on the Free Your Arms social media channels (see links below)).

GEN · IUS /ˈjēnyəs/
2. a person who is exceptionally intelligent or creative, either generally or in some particular respect

Finally I reached into my wallet pulled out a $20 and paid it forward to Julius, only asking that he share his love with others. (And there you have it - The Close). I actually did not mention that he made his ask at the top of our encounter (which you will see in the video posted below). The ask is the most important part of any pitch. And presenting it at the very beginning is how you do it (Don’t you watch Shark Tank?). This is a strategy that I did not learn about until recently.


This seemingly unselfish act of kindness I am displaying by paying it forward, may be more self-serving than it appears. It is not dissimilar to the final scene in Pulp Fiction. The Jules Character (No relation to Julius) played by Samuel Jackson and his sidekick Vincent (Played by John Travolta) voluntarily gives Pumpkin (Played by Tim Roth) $1500 while holding a gun to Pumpkin’s head. This after Jules thwarts Pumpkin’s attempt to take his MacGuffin.


…Now How much is there?

About fifteen hundred dollars…

Put it in your pocket, it’s yours.
Now with the rest of them wallets
and the register, that makes this a
pretty successful little score.

Jules, if you give this nimrod
fifteen hundred bucks, I’m gonna
shoot ‚em on general principle.


I ain’t givin‘ it to him.
I’m buyin‘ somethin‘ for my money.

Like Jules I am also “buyin‘ somethin‘ for my money”


If you were misled at the beginning of this article into thinking Julius was your archetypical entrepreneur we have grown familiar with, I propose that it is in these archetypes where the seeds of bias are planted. For the initiated his genius hides in plain sight. As an educational resource, his genius at the “soft close” is the type of low hanging fruit of knowledge I hope to harvest for the Everybody Is a Genius series.

Enjoy the video below.


A few friends have reminded me that by paying it forward good things will come back to me (which isn’t the goal btw). I do believe in karma. Anecdotally it makes sense that putting out good energy leads to more good things happening. Where I’m more skeptical is in a belief in a higher power. Some call this power God (Btw why is God almost always a man? -  A topic for another day - I digress) I'm not a believer or disbeliever in God but since paying it forward I have been encountering some strange coincidences.

For example -

A few weeks back right when I posted Why Should Billionaires Have All the Fun I quoted this verse from the bible.


MATTHEW 19:16-30

Hours later we got our biggest order of the year, and I would have to make the choice between keeping the money for the business, or paying it forward. I blogged about that incident here. It was like God was saying tread carefully when you invoke my name to make a point.


I found it strange that my first Pay It Forward profile has a name that is only a few letters removed from the feature adjective in our series. It is also a coincidence that his name is also a few letters removed from the name Jesus. But the biggest coincidence is that he said his genius was G.O.D. and that it was written on a chalkboard by my own hand (See Video). I'm not claiming that Julius is some kind of guardian angel, like the ones you see in movies or on Television shows. What I am claiming is that at the very least these coincidences may be a MacGuffen in its own right.




Survival Tales Of A Founder - Finding My Own Truman Burbank


As what usually happens with everything I do, the documentarian in me kicks in at some point and everything I work on eventually becomes an exercise in storytelling. This seems to now be the case with The Free Your Arms Social Media feeds.

This also begs the question - what other aspects of my life am I producing? A question for another day - But I digress.

Ever since my first work of public storytelling that I can remember in 1999 with my Web Manifesto where I wrote...

...The world is changing in many ways.  Demographics are changing, what and where people buy is changing, and scariest of all, the power that the internet gives a small company is a cause for concern for those who hold the power now.
— Me

…ever since I posted this manifesto (ok stop laughing), exploring the truth through art was a fascination of mine that I endulged publicly because of this then new platform we called the World Wide Web. I would post my thoughts on topics ranging from race relations as it applied to a then Mayor Giuliani to Digital Art in 2000 - But I always felt like there was a barrier in the blogging medium that prevented me from sufficiently expressing the truth as I saw it.


Years later I would find a new vehicle of expression in the form of video. I thought surely here is my chance to give voice to the truth as I saw it. In depth portraits of artists struggling to create their art, entrepreneurs building their empires, families struggling to stay together. This would be my vehicle for expression, I embraced it and thrived.

In the early days when I was shooting locally in Williamsburg and downtown Manhattan, I would document the truth as i saw it with little resistance. However as I became more and more sought after as an artist, I found that the roadblocks to revealing truths became increasingly difficult. Despite hiring me based on those early works, my corporate clients held tight reigns on the content I created. One example of this creative clash happened in 2009 while documenting The Roots during the making of their album How I Got Over - One of my video submissions was flatly rejected by the label. Frustrated I posted the following on my blog.

What you see in the video… is a montage piece, highlights which I can do in my sleep.  What you don’t see is the story I really wanted to tell. The creative process, the brotherhood of the band, the truth.  The human side of The Roots, just a bunch of guys who happen to be really good at what they do, nothing more, nothing less.
— Me Again

Who knew that scenes involving weed smoking, creative clashes, or in-fighting would not go over well with their label. Needless to say they never hired me again.

You see getting to the truth of things and expressing it for public consumption was always something I enjoyed doing. Yet finding my very own Truman Burbank was always my challenge. And despite my best efforts, It is a level of truth telling in art that has always eluded me.

Until now.


When I launched Free Your Arms 4 years ago, I started a streaming series titled Your Front Row Seat from my van on Periscope. At the time I always thought it would be interesting to document my own entrepreneurial story of survival but I never worked up the courage. My challenge as a documentarian was that documenting introspect is an unnatural artistic act for me. So I kept the camera pointed outward and limited most of my commentary to the sights and sounds of the passing cityscape. Viewers would ask me almost on a daily basis for me to reveal my face - but I would always politely decline, citing my documentarians mantra to keep my camera pointed outward.  Even on my own social media feeds you were hard pressed to find any images of what I looked like (and zero on the Free Your Arms IG). Revealing any personal details about myself just made me uncomfortable.


Something happened a few weeks ago. Maybe it was recognizing that the best story I could tell might be my own. Or maybe it was out of a need to find an alternative way to market Free Your Arms due to our Adwords account getting shut down. In either case somewhere I found the courage to turn the camera inward, smile, and tell my story.


Ladies and gentlemen I would like to introduce to you Delivered With Love - Survival Tales of a Founder - giving you an unprecedented behind the scenes look into building, saving, surviving a startup. Every day I post a running tally of my pitches, my closes, my negotiations, my meetings. I am documenting my daily grind which is summarized with a running graphic charting our previous days gross revenue (In black when we reach our goals, and in red when we don’t).

On my livestream (which airs 3 times daily from Tuesday through Friday) I dig deeper into the numbers, and give you details about my daily strategies, goals, successes and failures. These include stories about the people I meet, the demons I fend off, my wins and my losses.


For those of you new to entrepreneurship, over the course of the series you might gain unprecedented insight into what it takes to launch, grow and sustain a business, or the pitfalls to avoid. For those of you who are well into your own entrepreneurial journey, you might find a fellow entrepreneur in which you can relate to. As we all know this journey can sometimes be a lonely one. As the series develops over time, hopefully the tools I use to share my journey will develop as well, and you will be able to track the trajectory of my growth (Or failure).

Finding the courage to tell my entrepreneurial journey while employing my skills as a storyteller will hopefully give you a point of view that is not easy to find on social media. It seems like I have finally found my very own Truman Burbank, and he is me.

Tune in to @freeyourarms on instagram or facebook and please share with anyone who you think might benefit from this series..


Trevor - Founder Free Your Arms - Delivered With ❤️

Why Should Billionaires Have All The Fun? - How to give away your money and have fun doing it!
Maybe I’m just a stubborn and idealistic dreamer with my head in the clouds hell-bent on clinging to a non-existent point. That is if bankruptcy doesn’t cling to me first.

Maybe I’m just a stubborn and idealistic dreamer with my head in the clouds hell-bent on clinging to a non-existent point. That is if bankruptcy doesn’t cling to me first.

Why In the face of financial stress, growing resentment from friends and colleagues, and my business on the ropes, why am I so cheerfully giving away one day of revenue a week?

The pursuit of happiness.

The metric I used my entire life to measure my happiness was for the most part based on the social and financial capital I accrued personally and in my businesses. The Keeping up of appearances was the daily goal I would strive for in order to maintain my pride and self esteem. To this end, wherever I thought I might be falling short, my strategy would be (to use a familiar term)… fake it until I made it. I may not have been as blatant about putting on airs as others, but as a lifetime entrepreneur, this is a strategy that I employed far more than your average Joe.

Yes, those who know me best would most likely describe me as a kind and giving person. I am always the first to ask if anyone needs help, I am always the one to stick up for those I think are being treated unfairly, and I have been told that I am better than your average listener. These are genuine traits that I’ve had all my life. Which is why in recent months, and directly as a result of the charitable initiatives that I have been retrofitting into Free Your Arms - I realized just how far from that ideal I really am.

The fear of not obtaining or losing my social or financial capital became a prison I built up over a lifetime.

I always knew that despite my cheerful demeanor, that I was at my core a highly driven and annoyingly (if not secretly) competitive person. Anyone that I deemed a threat to my financial or social status would knowingly or unknowingly get pulled into my competitive lair. This could be someone within my own social circles, or it could be someone I had no personal interaction with whatsoever. For example; One of my favorite head-games I would play with myself while driving, was randomly choosing another driver (usually someone who I thought was driving too aggressively) and silently engage them in a race to an imaginary finish line. This happened several times daily. Or maybe I would randomly select a social media influencer with lots of followers that I envy and challenge myself to surpass them one-day (not having allot of luck with that one as my tens of followers would indicate). These are the types of mental exercises that I found challenging, but over a lifetime helped nurture a cancer of resentment and envy within. Basically anyone invading my space that was not on my team I saw as a potential threat.

Over a lifetime this competitive bent built a deep well of jealousy and resentment that existed side by side with my more charitable demeanor.

In the past few months, I started to more clearly see the unhealthy effects of this competitive streak. This was a source of fear, anxiety and resentment that colored how I viewed the world. My fear of not obtaining (or of losing) my social or financial standing became a self-imposed prison that I built-up over a lifetime. It also allowed others to leverage these fears against me through withholding or removing these rewards. It wasn’t until a recent holiday trip to my parents home in Florida that I would unintentionally start down a path of growth that I find myself on today.


A little burnt out from working on Free Your Arms over the past 3 plus years, I took my annual thanksgiving trip to visit my folks in Spring Hill Florida (this is my go to destination to decompress). As I usually do when I’m down there, I try to start new and fun projects to help occupy my time. On this trip I would use my time to work on a business plan for a platform that I hoped would allow the younger members of the community to provide tasks to the older less tech savvy members of the community. It was like TaskRabbit but for the people who would not know how to use Taskrabbit. Also the taskers would come from close friends and relatives. (Most of my family and extended family transplanted from New York to Spring Hill Florida so I thought this might be a great testing ground).

After dozens of iterations I would eventually call this project The Shop (which eventually became the website you are reading this blog post on right now). As I was building this community based platform, I could see that my world view as it applied to my business started shifting from being monetarily driven to a more charitable outlook. This led to self-examination about my role as a founder. The more I iterated this business plan, the more I realized that I felt happier working on The Shop than on The Free Your Arms Website as it currently existed. At some point I decided to merge the two businesses under the The Free Your Arms banner, with the old business adopting the values I was weaving into the new.

Immediately I started to feel happier, less stressed, and less anxious. I realized just how much fake love and true hate I was reflexively putting out into the world. I had a new interpretation of “fake it until you make it” Instead of faking success I tried to fake loving my enemies until I actually started to feel less hate. I wouldn’t be screaming at drivers on the road (as much), I stopped being obsessed with rooting against my competitors, and people on social media who I viewed as “unworthy”. I even tried to stop hating President Trump. I’m still working on that one. Still several times a day (every day) I have to literally stop myself and say out loud “stop hating!”, or “you’re such a hater!”. Like an alcoholic this might be a lifetime battle, but as they say knowing is half the battle. Now instead of seeking external validation I will never find, I have shifted my gaze within to find the happiness I deserve.


If the past is prologue then I’m guessing at some point I’ll take this new outlook on life just a bit too far before I inevitably have to pull back. My friends and family think I’ve gone way past that point already. Here are a couple of traps I might want to avoid…

  1. How do I distinguish what I consider healthy impulses (the desire to connect, the need to express oneself, or the desire for my basic survival needs), from the unhealthy ones (The desire for social and financial capital as a validation of my happiness)?

  2. How do I avoid hurting the people I care about that might bear the brunt of my actions? Just because I’m finding less meaning in financial and social rewards this does not mean that everyone else will. And if my new measure of happiness, which includes seeing others gain the same freedoms and happiness I am experiencing. The truth is I won’t be totally happy if those around me aren’t as well.

The truth is I don’t know how I’ll navigate these challenges.


Yes that little detail. The challenge I get from most who disagree with my new approach usually takes some version of the statement below…

Being charitable is great, but why put my business at risk? Why not just be charitable in private? Why not wait until I’m in a better position to give? I lean on a passage of scripture as my retort…

if you want to be perfect, go, sell your possessions and give to the poor, and you will have treasure in heaven

Matthew 19:16-30

Even as a child growing up in a strict religious household I could grasp the message in this parable. (Spoiler alert - even the rich man in this parable knew better than to “sell his possessions). I believe that once you have fulfilled the basic needs portion of Maslow's Pyramid, that the only thing separating us from experiencing the type of happiness associated with giving is to give, give and give until it hurts (As my dad use to say).

In an ironic twist, the researchers found that there is one thing that decamillionaires can do to get even more happiness -- give it away.


As I see it now, as I transition away from my pursuit for material and social validation, I hope to be able to leapfrog the whole “getting rich and famous” part and right into the “give it away” part that make the super-rich so super-happy. Why should millionaires and billionaires have all the fun of being uber-charitable? I half-jokingly ask myself.

The truth is if I’m not promoting the same kind of growth I am experiencing personally in my company, then I feel like I may be missing an opportunity that I may never have a chance to experience again.


Here is a truth that I think proves I am not a crazy person.

Every entrepreneurial fiber of my body is revolting against this new direction (in particular Pay It Forward Friday) like an addict going through withdrawal.

I hope that on the other side of this pain I will find something that I haven’t discovered in myself before. The kind of growth that sometimes only can be achieved through real pain. In the few months that I have been on this path, I have experienced the type of growth I haven’t experienced since I abandoned my childhood religion in 1991. The result, a discovery of self that is a direct result from the pain of giving, and a new measure of happiness. To ignore this path or to promote anything less in my business would give life to the cancer of unhappiness and allow it to come out of remission.


Maybe I’m just a stubborn and idealistic dreamer with my head in the clouds hell-bent on clinging to a non-existent point. That is if bankruptcy doesn’t cling to me first.


Maybe I am in ironic pursuit of exactly the type of social and financial validation I am positioning myself against. Am I secretly hoping to become the next Accidental Billionaire? Would that really be so bad?

Whether I soar or I crash, I hope it is a journey worthy of the pain and humiliation I’m putting myself through by pulling back the curtains for you to see me, warts and all.





Don’t forget to follow our daily live-streams Delivered With Love - The Truth in 3 Acts (Tuesday - Friday on our social media channels below) And don’t forget to support Pay It Forward Friday’s by purchasing items each Friday in our store.

Raised to date

Raised to date

PS: My cousin said

You know, you are kinda hazing yourself by doing this in public. You missed it in college but you are getting it now.

I lmao’d