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.
PANHANDLING VS. SELLING
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.
SO WHY DO IT?
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.
THE SOCIAL EXPERIMENT
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 FreeYourArms.com and Vertoe.com (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.
TELL THESE PEOPLE SOMETHING THEY DON’T KNOW ABOUT ME
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.