Posts tagged panhandleitforward
From Pitching to Panhandling - My Journey from Boardroom to Street Corner


A few weeks ago I launched a Live-Stream series called Delivered With Love - The Truth in Three Acts - Each Tuesday through Friday (three times a day) I would try to be as truthful about my business as my pride would allow. Shortly after launching the series in what might be described as a temporary moment of insanity, I announced that each Friday my company Free Your Arms would be donating all of our revenue to folks in our community who needed it more. I wanted to see what would happen if I applied the principles of giving even if it hurts my business.  I called this day Pay It Forward Friday’s. The challenge I faced is this charitable mission would come at a time when we could least afford to give money away. You see, Free Your Arms is not yet profitable and under financial stress. This left my friends, family, and partners (all who I either owed money to or could use my help financially) scratching their collective heads. To promote this event I thought it would be a good marketing strategy to panhandle on the street for donations which would also go back to the community.

After a week of heavy promotion on our social media the time was finally here for me to hit the streets. Dressed in my Free Your Arms Jumpsuit, Doc Martens, Warby Parker glasses and winter coat at about 3:15 pm last Friday I headed for the intersection at Meeker and Metropolitan Avenues in Williamsburg Brooklyn. This is the main thoroughfare between the Lorimer L stop and all points Williamsburg (including my home/office). I decided to panhandle on the East side at Meeker Avenue under the BQE overpass which is opposite the more common panhandling spot on the westside of Meeker Avenue under the overpass. I parked my van about half a block away, pulled out my cardboard sign, my bottle wrapped in paper tape and placed my phone in a hidden compartment on my sign to livestream the entire pitch.

The sign which by the way read …


OK I was ready. I hit record on my phone held up my sign and started pitching. From this moment everything seemed to speed up and a dozen questions I didn’t consider were rattling off in my head. Which way do I walk first? Do I pitch the stopping cars?  Do I approach the crossing pedestrians? What about eye contact? Do I ask for change or just shake the cup? Is the camera recording? What am I doing here? Should I have authored a more realistic sign? Was I sufficiently prepared? Will I get any donations dressed like this?

Then out of nowhere I felt it - the first dollar was dropped into my cup. It came from a young hip girl with a friendly smile. Then only a few minutes later a truck with two men inside pulled up alongside me.  Out came a muscular hand holding a loosely wrapped sandwich. I hesitated for a split second as it never occured to me that people would donate food. The sandwich was bigger than the donors hand and it almost fell apart as I tried to grab it while holding my sign in one hand and my donation cup in the other. After securing the beefy delicacy I became elated “I got a sandwich!” I shouted as the truck drove away.

At this point there was a small crowd gathering at the crosswalk and inside a restaurant observing the happy panhandler. A tad embarrassed to be making a show of begging and yet joyful that I had experienced these spontaneous acts of kindness, It dawned on me that I was this afternoon’s street entertainment.

My plan was to stay on that corner for another 20 minutes before I left for my next delivery. During that time I was mostly ignored by pedestrians and drivers getting variations of the canned response ‘I have no change’. But what really irked me was that no one seemed to be reading the sign that I so cleverly crafted.

This reminded me of the scene in The Amazing Spider-Man when he was trying to find the owner of a stolen bike. One New Yorker walking past Spidey so fixated on his phone that he never realized that the superhero was standing in front of him soliciting his help. His reflexive response to Spidey without ever lifting his gaze was “I have no change”.

This is the refrain I would hear repeated to me many times in the next few minutes, many of whom also avoided making eye contact with me. All though it would have been nice to be acknowledged, The truth is it didn’t bother me if I was ignored totally. In sales I learned that cutting my losses with uninterested prospects quickly is preferable to engagement with no reward.

15 minutes passed and frostbite started to settle in (I wore my open fingered driving gloves). At this point I was just waiting for the experience to be over. It was then that another millennial stopped and almost tore his Whole Foods bag apart just to find a tangerine for me. It was another unexpected gesture of kindness. This time I was able to contain my joy.

It was now time to wrap-up today’s entertainment and head back to the warmth of my van and head off to my next delivery. In the minutes immediately following I was buzzed with adrenaline. It was as if I was floating above my own live-streamed experience. I knew in that moment that I would be back.

NOTE: I did live-stream the Panhandle session but forgot to save the feed on IG so it disappeared after 24 hours, I will be sure to save the next session.


At the end of the first day I generated $228.10 from and from panhandling I was able to get One Dollar, a tangerine, and a sandwich.


Later that night after the adrenaline high dissipated it became very real what I was sacrificing - with so many of my personal and business bills unpaid, my utilities and phone on the brink of getting shut off, my bank account in the negative, it occured to me that Pay It Forward Friday could really tank my business.  A business that I put 12 - 18 hour days, seven days a week for the better part of 4 years. That’s 4 years not going on a single date, almost filing for bankruptcy, having two vans repoed, tanking my credit, often not being to pay my vendors or my crew. Then I had a mini panic attack.

This was a whole new level of irresponsibility.


One of the goals I listed when I made the initial announcement about PIFF was to document the similarities between a street beggars hustle and an entrepreneurs hustle.  I found that at least at first there was no real difference between begging for money in the streets, selling hand-warmers in a mall, T-shirts in a flea market, video services to a fortune 500 company, delivery services to hotels, or pitching my business on national TV.  All of which I have done over the past 20 years.

I felt empowered knowing that if I ever hit the kind of rock-bottom that puts me out on the streets that I would not be above doing what it took to survive.

On this first day I would say it was easier begging in the streets than I expected. Keeping in mind there were no monetary targets in place. Aside from that little detail I didn’t have to rehearse a pitch, and I was dealing with a more receptive audience than the typical gatekeepers I encounter while selling. Ironically the thing that made begging in the streets more difficult than typical sales was the public spectacle I made of it all.


There were two main motivations for why I decided to giveaway a large chunk of my company precisely when we can’t afford it.

First - I wanted to leap into an experiment about social values as it pertained to business. I am 48 years old and there is probably more road in my rear view mirror than lies ahead. If I am not going to build my ideal business now then when?

Second - I knew that if I hadn’t made such a public show of doing this, I would have started the process of gracefully bowing out once the risk of losing my business became real. I needed to put it out there so that the pain that would come from pulling out would exceed the pain I would feel by moving forward with this idea. So far so good.


If you have been tuning into my live-streams then you have heard me harp-on about the joy that comes in giving more than I take, my struggle with not having to find validation through material wealth or approval from my peers. You heard me describe the natural high that comes from living each moment doing the things that I love…

what happens when you weave aggressive social values into the fabric of a for profit company? How would that impact the surrounding community? How would that impact the members? How would that impact me?


Over time I have seen a profound change in my thinking. For one… my perspective on social norms were being transformed. When I first launched this startup I hoped to launch the next Airbnb or UBER. However In the past few years (thanks in big part to my mentors at SCORE NYC) they showed me that even if I could raise venture funding (and that is a big if) venture money may not be the path for me, they were right, I would have been miserable. So I decided early on to bootstrap. About a year later my choice to bootstrap our growth would soon be called into question…

while working to form a potential luggage disruptor partnership between and (who launched a different luggage storage disruptor model years after we opened up this category in New York) - Sid a co-founder at Vertoe and I often discussed or debated about the merits of venture capital vs bootstrapping. Months later Vertoe would join one of the top incubators in the country (Techstars) and raise 1.8 million fueling their expansion nationwide. Meanwhile I was still trying to keep our lights on.

After Vertoe raised their millions, the competition for market share in luggage storage disruptors was heating up and it felt like everyone was throwing their luggage in the ring and raising millions, It was a real test of my fortitude and not good for team morale. Thankfully my team stood by me and we soldiered on. The truth is with venture money comes expectations of exponential growth that would have changed the DNA of our business. While some seek this type of transformation It is not the kind of growth that I would find fulfilling. Venture Capital investor Chamath Palihapitiya has a less flattering description for this kind of growth. He describes it as a ponzi scheme (listen to in the link below for more on that).

Looking back over my 20 plus years of entrepreneurship I could see a pattern. At every crossroad where I had to make a choice between growing big faster, or being the narrator of my own slow organic growth, I chose the slow organic path. But I still couldn’t help but ask myself this question… Am I really growing, or am i becoming the dreaded “cautionary tale”? The ironic answer is… I no longer care if the latter is the case.


The day after panhandling I had what alcoholics would call “A moment of clarity”. Were the beggars and panhandlers of the world the ones who are truly free and fulfilled?  And if so what does that say about our capitalist culture and our obsession with material wealth? What does this say about the current “fake it until you make it culture”? Is Pay It Forward Friday an experiment in socialist values?

Something happened to me as I started to reveal the truth about myself on my live-stream and as I stood on the street panhandling for money. Unlike every other time in my life when I was stressed for cash, I was happy. This was a first for me. It was at that moment that it occured to me that I was freeing myself from the expectations of society.

If I am able to panhandle on the street and in my neighborhood It would be safe to say that I cared less today what people thought of me than I did last week. I started to see things from a new perspective. I could see a power dynamic changing. I realized how many people in my professional and personal life used my economic and social fears of being embarrassed or humiliated as a weapon against me. It wasn’t intentional, it was systematic. Once I revealed my truths to the world, I would start to disarm my naysayers, my critics, my competitors, my bill collectors. With this one public display of humiliation there was nothing left for them to use against me, external expectations floated away, and my journey to freedom began. Now I was able to smile at the world.

Then I remembered this scene from 8 Mile. I saw the Anthonie Mack character (Papa Doc) as the trappings (the naysayers, the critics, the competitors, the bill collectors, the expectations) and I viewed the Eminem character (Rabbit) as the one choosing to let go of the trappings of wealth by revealing his truth, his failures, his humiliation.


A few months back I considered giving up my apartment, moving into a motorhome and living a nomad’s life. It is the kind of freedom that I have entertained for much of my adult life but was never able to take that final step. About 10 years back I went as far as packing my bags, calling my girlfriend while she was at work to let her know I was about to hop on a train to travel the states. The following lines from my favorite scene between Vincent and Jules in my favorite film of all time Pulp Fiction sums up my feelings at that time...

So if you’re quitting the life, what’ll you do?

That’s what I’ve been sitting here contemplating. First, I’m gonna deliver this case to Marsellus. Then, basically, I’m gonna walk the earth.

What do you mean, walk the earth?

You know, like Caine in “KUNG FU.” 

My girlfriend at the time (God bless her for putting up with me) talked me out of that attempt to walk the earth like Caine (cried and screamed is probably a more apt description). Yet this feeling to free myself from the trappings of societal norms has never quite left me. Even as recently as a few months ago while texting with my cuz, I shared my impulse about moving into a Motorhome and traveling the country. He then shared his own short-lived experience living in his car…

I had just gotten back from backpacking in europe. which was a liberating experience. military folks live in camps, so staying in my car didn't seem like a big deal... after a few days of doing it, I got a perspective of life that can only be acquired by doing that. It was the life of being homeless… it wasn't long before I could spot other homeless people because we had similar routines and spent time in the same sorts of public places. It felt strange to not have a home to go to at the end of the day….

And then came the warning that scared me straight.

I would caution one thing though. it is an experience that can normalize living in the margins. It could lead to a slow progression towards accepting less and less. be aware of that.

So what next? I am not ready to go all-in living a homeless existence, but I have been granted over the past few weeks a new perspective on what is important. Right now that means helping others, and seeing where this social experiment takes me. The goal for me as an entrepreneur is to find a way to make it all self-sustaining without the need for the validation that comes with material wealth and collecting trophies. Hopefully you can help me achieve this by making purchases on our store. If your purchases are made on a Friday, we will pay that forward to the folks in the community who need it more. Any other day goes to the business and hopefully helps keep the social experiment going. Plus we have some really great and innovative products. I forgot to mention that part.

In the short term (this week) I will be back out panhandling it forward hopefully a bit more prepared than I was last week. Also I will be paying those funds raised on the last Friday of each month. I will be live-streaming that process along with our fundraising efforts and I will need your help. If you want to join this experiment or help out in any way message me at

In the meantime BUY, BUY, BUY Friday’s and everyday.


Trevor Bayack - Free Your Arms Owner/Operator

Delivered With Love

Money Raised To Date

Money Raised To Date

P.S. I would advise everyone to try panhandling for a day. It will set you free.