Do you remember the first time you heard the word “no?” I doubt it. I certainly don’t. It’s a word we here often, daily perhaps, even more. Especially as children, we learn the word “no” almost immediately. “No” is a word we will hear for the rest of our lives. But very rarely is “no” truly finite.

I’m reminded of this word, this strong and intimidating word, by watching American Idol tonight. I know, cheesy, but as an entrepreneur often does, I tend to put lots of everyday observations into the context of entrepreneurship so bear with me. One of the contestants on tonight’s episode was pleading and begging with the judges (Simon, Randy, Kara, and guest judge Ellen Degeneres). The judges were resolute in their decision, there was no chance in hell she was going to beg a “yes” from them, yet she continued until it got a bit pathetic. Ellen was quite clear and concise in the way she explained to the contestant that this “no” was not the end of her life, nor was it the last “no” she’ll ever hear, rather this moment is something that she’ll look back on as just another “no” that made her stronger. That kind of wisdom, that Ellen applied, is only gained after overcoming the word “no” and having something to really show for it. Most successful people, no matter what kind of success they’ve had – be it artistic success, professional success, financial success, success through freedom – have overcome this word and made it an opportunity, not an obstacle.

I’m reminded of how many times I heard the word “no” as a teenager when asking a girl out (I did hear “yes” from time to time!). I’m reminded of how many times I heard the word “no” when I didn’t make the team, when job hunting, when selling something, or when pitching venture capitalists.

The word “no” is rarely the end of the road, more often it’s an opportunity. Hearing the word “no” automatically prompts a follow-up question that you can hear from children more often than adults, and it’s “but why not?” or “how come?” That question, that follow-up to the “no”, is the opportunity to learn more, to understand why you aren’t getting what you want.

That’s what “no” is – an opportunity to learn, to improve, to achieve wisdom. Next time you may still get a “no” but perhaps a little later in the conversation.

Being able to overcome the word “no” is a defining characteristic for optimists or idealists. On the flip-side, not being able to overcome this word is a often a defining characteristic of the unambitious, or of pessimists.

Being able to deal with this word is also a defining characteristic for entrepreneurs. I’ve heard this word the first time I hit the streets to sell a CitySquares product, and I learned from it. I bettered the product, or the pitch, and heard it again, and again, until finally I heard Yes once, then twice, then again. I heard the word “no” when raising money for CitySquares, when we weren’t ready. I heard it when I thought we were ready and thought the prospective investors were crazy or foolish. I heard it when I tried to close our first really big sale, or when I tried to establish a big partnership. Yet never has “no” been finite for me.

The word “yes” is an exciting word, it means you got something right, or got what you wanted but the word “no” can oftentimes be more valuable.

Entrepreneurial Lessons in 2009

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2009, you sucked! Good riddance to you! That was a horrible year that I just get sick thinking about. As it pertains business matters, it all started in late 2008, the second half of September to be precise, when the economy tanked. The entire country panicked, and the global economy didn’t respond any better. It really was the Global Economic Crisis, and as NPR is now reporting apparently it’s been “abated” but the effects are to linger for quite some time. One thing is certain, CitySquares was affected greatly and quite immediately. I won’t go into the details and the describe the punches we took, those we handed out, and the battle scars we have to show for it, but I will highlight some of the challenges and battles that really stand out in my mind:

  • As soon as the hard times hit I saw an immediate response by the staff at CitySquares. For the most part, the team held together and today we’re tighter and stronger for it. Like a tribe, we stuck together and hunkered down while battles and storms happened all around us. We were not well fortified but we survived and now we’re about to thrive! On the other side of the coin, a couple of our tribesmen demonstrated an inability to persevere and overcome these challenges, and some weaknesses were exposed and ultimately eliminated. Thankfully that ended rather quickly and the tribe was/is better for it.
  • Small businesses, specifically brick and mortars and mom-and-pops, got their asses kicked much like we did. Those who hadn’t yet learned to fly unfortunately fell from the nest and met their demise in ways that were hard to watch. Balances went unpaid, phones disconnected, and personal stories of financial tragedy were common. It was truly heartbreaking to see. Yet many also survived and are resurfacing with tougher skins and stronger businesses!
  • Beyond the staff at CitySquares I also experienced something completely new and foreign to me – board members and shareholders reacting in different ways. The vast majority of them demonstrated a wisdom and calmness that really impressed me and taught me a whole lot about pragmatism and experience. That, however, was not always the case. In a couple of isolated incidents I witnessed naked panic, fear, and fright and this came from the worst places possible in the corporate structure. I will not divulge the details not for lack of transparency but for reasons of respect and professionalism – that is a fine balance you know! As a result of these panicked and frightened reactions it was apparent to me that something had to change and change immediately or the company was destined to collapse for unacceptable reasons. It’s one thing to fail because a business model fails, or because of timing or market and/or economic reasons, but its another to fail because of human emotions, poor judgement, and failure to communicate and work as a team. At the end of the day, however, our shareholders demonstrated their commitments to the company but continuing to support us financially and through other supportive means. Again, we are now better for it!
  • As a leader I learned so many lessons in the past 12+ months, but two in particular that I will not ever forget. For the sake of brevity there were a few incidents in the first half of 2009 when I lost control of my emotions and let anger and fear win. These incidents are not something I care to revisit in detail and am embarrassed to detail. I have made amends in both instances. These two cases taught me some huge lessons, lessons that took me months to truly understand and apply to life and work.
  • In a tribal organization like ours, loyalty, communication, and teamwork are absolutely vital. What became incredibly apparent to me was how strong the tribe is when communication is at its best, when leadership is performing in the right ways, and when the tribesmen are truly committed to each other and to the tribe’s visions and beliefs. There is something almost dogmatic about a small company! I saw people step up to the plate in the most amazing ways. It’s still happening today. People are not willing to settle for less, nor willing to sit back and be OK with the way things are or may be heading, they expect more from themselves, from the others, and from the tribe as a whole. There is much of this happening right now, as it should always be! A sort of shuffling is happening internally, and its happening in a way that is uniting the tribe only more and making the company better and more focused and determined than ever before.

These points are the major ones that stand out for me, as an entrepreneur and as the chief of the tribe. There’s lots of business related stuff too, like how we got through the last 15 months, and what changes we made to our business/model/execution, etc. And those things are continuing to happen, but the reality is this: CitySquares is stronger, more successful, and closer to our goals than ever before! Its because of the above points, among lots of others, that we are here today.

A few of my entrepreneurial goals for 2010 are as follows, and I will soon be blogging about these things:

  1. Continue to grow and mature as an entrepreneur, as a CEO, and a tribal chief. How? Continue to identify and improve those leadership traits where I am weakest, and harness and cultivate those where I am strongest. I cannot do this alone either, I need my tribe to help me, I need to read and learn more, talk less, say more, listen more.
  2. Blog here more often, with transparency, and with purpose.
  3. Create and participate more in entrepreneurial circles, networks, and communities (e.g., The Founder’s Quandary)

I am still working on these ideas and a couple others. I will be blogging again here very shortly. Stay tuned for more!

2010 is going to be an extremely good year for CitySquares. No doubt we still have lots of lessons to learn and battles to fight, that’s par for the course. But if we can survive and unite the way we did in 2009, than 2010 is really going to be something else!

Happy new year to you all, may your 2010 be filled with new found freedom, with health, and prosperity.

The Economy: An Opportunity

Serial Entrepreneur Jason Calacanis who recently retired from blogging and started, instead, an email newsletter has always been straight-talker. His candor and quick tongue are traits I find in myself that often, like Jason, get me into trouble. If you subscribe to Jason’s newsletter you certainly received his latest. If not, you can find it here on Alley Insider.

Jason’s email has a “focus on the entrepreneurial and startup depression and economic downturns/depressions–and how you can deal with them.” He suggests that the economic downturns we’re seeing right now will kill 50-80% of startups within the next 18 months, and that entrepreneurs need to be prepared to take certain steps to fortify, but also to monitor and address their own “entrepreneurial depression and anxiety.”

I love this topic. I’ve stated many times on this blog, and otherwise, that one of the biggest defining characteristics of an entrepreneur is his/her perseverence and resiliency. Those characteristics are to an entrepreneur like water to a fish. These are traits that an entrepreneur just requires 100% of the time. Jason states,

“Depending on your DNA, getting your ass kicked is either complete torture or deviantly rewarding. Truth be told, I like getting my ass kicked because it makes me angry, motivated and focused.” Continue reading The Economy: An Opportunity

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.