My Truth about Entrepreneurship

You know, I’m a pretty high-energy, go-get-em kinda guy. I’m not lacking in confidence, hope, motivation, and dreams. I’ve been to the bottom before, and it sucks. I’m a little bull-headed. A lot of people have learned not to get in my way when I’m on a mission. It’s just how I’m wired. I have to tame that energy, harness it too. It’s also partly how I was raised. My folks were very good about supporting my dreams, no matter how strange they were. Although, at times, they questioned my sanity, and they were usually justified! So I learned some valuable lessons.

I remember, as a kid, probably about 10 or 11 years old, I wanted to earn some money – probably for a CD player or a new album, who knows. So I started a company called Helping Hands with some friends in the neighborhood. We were actually quite organized. I went door to door handing fliers to home owners offering to mow their lawns, rake them, shovel snow, whatever the task, we’d do it. Ultimately, my friends didn’t stick to the ‘business plan’ and I was left to do it alone, and I did, for a few months, earning some good cheddar. I kept some of those clients for a couple years, pushing my Dad’s lawn mower around the neighborhood. That sucked. Believe it or not (and it might sound silly) but that taught me some early lessons about pricing, selling and delivering the goods. After high school I worked retail, I shoveled driveways and parking lots for an entire winter, third shift. I painted houses. I worked as an insurance appraiser. I sold cars for a good while – selling new and used cars. That taught me a lot about sales, a LOT.

Ok, so fast forward to modern day Ben (do I sound pompous? Eh, too bad). The story of how Citysquares came to be has been told, and I won’t obnoxiously start on about my hopes and dreams for a better day, and a vision for a better future for me, my wife, my family, my community, my spirituality, and my time on this planet. Even I get tired of hearing it, even though I believe it all in my heart of hearts and that’s what this is all about.

Back on the point: 90% of the average Joe and Suzy Q can’t really understand this entrepreneurship thing. If you are an entrepreneur reading this, you’ll understand either from past experiences or from your current situation. Most people just don’t really get it. Some even see entrepreneurship as greed. As much as our society and capitalism makes entrepreneurship within everyone’s grasp, it’s only a vague concept to most people, it’s not something that can be lived by reading it in the headlines, or in a schoolbook. It has to be experienced. My wife is constantly amazed by it, and frightened by it, because she wasn’t raised in an entrepreneurial home. I was. My father was an entrepreneur, a small business man for many years, and long before I was an idea. His father before him was an entrepreneur, running a successful print shop in lower Manhattan for many years. My father and uncle ultimately took over that business. My mother was an entrepreneur. She was a court stenographer for many years, a grueling job, but she was the best and courts and judges all over requested her. She did this on her own, through her own little business. After she retired from court stenography she kept up with her entrepreneurial activities. So anyway, like I said, I grew up around it. Most people did not. Most people don’t understand it. They’re fascinated by it, and talk like they want to do it – but most never do and many live to regret it. Everyone has an idea, everyone has the spirit. Not all have the guts. Guts can be confused with foolishness, haste, even mental illness.

As a startup entrepreneur, who’s been at it for 15 months, boot strapping, grinding it out, with Bob, with Chris, and with my supportive family and amazing wife, I know all too well the pain that comes with it. Where there is a ton of hope, vision, passion, energy, motivation, inspiration, there is trepidation, doubt, depression, panic, hopelessness, and fear. Those later emotions are few and far between, for me anyway. But as the clock ticks, life goes on around me, those wonderful, elating emotions can sometimes become diluted, almost muted by the monotony of the days, the weeks, the months, and those big question marks stamped on every rising sun, and every rising moon. Thoughts of starting a family come flooding in, and sometimes I wonder if I’m just being selfish. Those negative emotions start to bubble up because a bill isn’t being paid, or sales isn’t going as planned, or morale is low, or that investor hasn’t called me back yet, whatever it is. There are those moments. There are many, many, sleepless nights. There are health issues too – really, there are.

Then there are moments that remind us what it’s really about – that refresh us, validate the vision, and bring it back into perspective. Those moments are rare, and they have nothing to do with dollar bills, or to do with any technology. They have to do with people, relationships. Events, like WebInno, or people who you choose to surround yourself with, who buy-in to you and the vision, and passion, and want to be part of it. Those people, the really valuable ones, are hard to come by. Very hard to come by. There are people who where the mask well, they talk the talk well, the say all the right things, but it doesn’t take long to see that they’re full of shit and they don’t really have it, like you want to believe they do. The real ones out there don’t really want anything – they just want to be involved, help, and see you succeed and even be a part of that success. But they’re willing to take that chance.

The passion we have here is contagious, the energy and spirit and tangible, and the future is bright and attainable! Sometimes these special people come along, they walk into your life, and in one conversation they can make it all better – put it all into perspective.

Ok, I’m speaking so figuratively that I’m starting to get annoyed by it. Look, it’s like this: Entrepreneurship is not easy. If it was, in the words of my father, everyone would be doing it. So true! No one ever can say that entrepreneurship is easy. Fun? Exhilarating? Wild? Fantastic? Oh hell yes! I love every moment of it and wouldn’t trade it for any other job. I mean that. But entrepreneurship has a dark side. It can be totally scary, frustrating, and one can feel hopeless at times, panicked, and uncertain of what tomorrow brings. I mean that literally – you just don’t know what tomorrow may bring. You can plan tomorrow, but you can’t plan for what tomorrow may unexpectedly bring in an unfunded, bootstrapping startup. I’ve been fortunate enough to have been blessed with 10 working fingers to type with, eyeballs that can read and understand code and the english language, very active and well exercised vocal chords, and a brain that just won’t stop buzzing – all – the – time. As a guy who loves technology, but doesn’t live and die by it, but also as a guy who understands people, what makes them tick, how to converse, how to sell and make friends and relationships, I’m truly fortunate. With these skills, I’ve managed to assemble what you hopefully see today – a startup Internet business that has a ton of potential and a very bright future. My colleagues Bob and Chris, my hombres, are still here – trusting me, through it all. We trust in each other, through dark times and bright times. With supportive family, friends, colleagues, advisers and mentors, I’m really quite humbled.

There is an old Chinese proverb, I believe, that goes like this:

The temptation to quit will be greatest just before you are about to succeed.

I have felt that temptation, I think I just went through it, over the past couple of weeks. I believe that I’ve just turned that corner and I’m now staring success straight in the face.