Doing What You’re Good At

Seth Godin posted a nice little piece today, as he frequently does, about passion and expertise in whatever you do. Very timely, as I’ve been facing this very question in the past few weeks.

CitySquares has a tribe member who’s been with us for about a year now. She’s a rock star in so many ways. She also really enjoys her job and is proud to work at CitySquares. This is partly what makes her a true member of the tribe.

For the last year she has filled some big shoes, and performed in a job that was not well defined for her. She kicked ass at it, like I never thought possible. And over the course of time she’s naturally filled a role within the company that not only has been a bit of a vacancy within the organization, but is something she’s simply really good at.

No one asked her to do these things, no one pointed her in that direction. Instead, she saw a need in the company, and then filled that need. She’s done so with poise, enthusiasm, with total ease. Today, she was formally moved into that role.

What she did over the course of time, perhaps unknowingly, is what she’s good at, and what she enjoysvoluntarilyon her own. She did so because she has a natural expertise with it, and because she has a passion for it. You just can’t buy that.  The result, and hopefully the result of good observation by management, is a permanent move into that role. This will result in even better performance in this role, it addresses a need within the company, in a happier, more efficient, effective successful company, it results in happier customers and better retention rates, and best of all – a member of the tribe who’s even happier and more successful.

Fight or Flight

better-angry-bear-pictureEveryone is talking about the bad times that are here, how difficult things are and how difficult things are going to get. It’s ugly out there – no doubt about it. As an entrepreneur I have to listen, read, and watch all the headlines, reports, and opinions. It’s also my job to pick and choose which sides of the arguments I want to take. Just as a smart consumer would take in all the facts about prices of goods, and investors will take in all the facts about the stock market, entrepreneurs need to take in all the facts about their markets and the rest of the climate. The tricky part, though, is not just taking in the facts, its forming an opinion and then a plan based on the facts and your perspective. This is when leadership is tested the most – in the face of adversity. And this is when choices are made – choices that are the difference between life and death. Look around people – those decisions are happening right now, everywhere you turn. Companies, homeowners, consumers, investors – those decisions are being made for better or for worse.

Our primal fight-or-flight response – something that’s deeply ingrained in our primal instinct – is tested during times like these, among others. Fight-or-flight theory suggests that

“animals react to threats with a general discharge of the sympathetic nervous system, priming the animal for fighting or fleeing. This response was later recognized as the first stage of a general adaptation syndrome that regulates stress responses among vertebrates and other organisms.” – Wikipedia

Basically it means this – when faced with a challenge that threatens your survival, what do you do? Do you fight? Or do you flee? Either answer could be right. For example: If you are in the forest and face-to-face with a mother-bear in the woods, you’re natural instinct may be to flee – run for your freaking life! And you may be right, but do you take that risk? Or do you just stand still and don’t make a single movement. That’s also the right answer. Or, do you stand tall, wave your hands like a maniac and create the illusion of size, height, strength, fierceness? Either way, what you’ve decided not to do is to fight the bear. Yet if you’re face-to-face with someone who’s invaded your house in the middle of the night, you’re natural instinct is to fight the attacker off with a weapon. That might be the wrong answer. Either way, we’re talking about instinct here – our primal reaction to what challenges our survival.

There are fine lines here too, subtleties. For example, some people face very tough challenges in their lives. Maybe a child lost her parents when she was very young – does that child now stand up on her own and claw her way through life, taking care of her baby brother? Or does she give up, and rock back and forth in a fetal position? Hard to answer, hard to say. How about an adult who loses everything to a gambling habit instead of safely learn from these slides, or to drugs? Do they claw their way back or do they slide into the downward spiral? And when do they decide to start fighting? Hopefully before it’s too late.

OK, you get the point – sorry to be so depressing but these are examples that shape who we are, these are decisions we all face at one time or another, in our respective ways. They define people for the rest of their lives.

This now begs the question – what does a company do when faced with hard times? When an economy is slowing down, when the chips seem to be on the other side of the table, what decisions does the company take? How does it respond? How does its personnel respond? How about its sales people? Management? What about the Board of Directors, or the shareholders? How do all these stakeholders respond? And do they all agree?

I was on a flight the other day thinking about this very subject while flipping through the recent issue of Inc. magazine when at page 28 I came across a little quote from famed management guru Tom Peters. To quote Inc.:

Tom Peters is most associated with managing during bad economic times. His In Search of Excellence was published amid the sharp recession of 1982, and Thriving on Chaos debuted on Black Monday in 1987. On he recently wrote about running a business in a time of “significant and sustained economic disarray.”

I liken Tom’s quote to this very subject – fight-or-flight. My favorite line, and the same line quoted in Inc., is in bold text below:

While many businesses will fail amidst the current economic crisis through no fault of their own, some will survive in spite of the odds—and a few will surprise by turning a messy situation into economic-competitive advantage. The requisite winner’s attitude is expressed by former Ritz-Carlton chief Horst Schulze, commenting on his decision to launch his new high-end hotel business, Capella, despite the market madness: “I do not accept the explanation of a recession negatively affecting the [new] business. There are still people traveling. We just have to get them to stay in our hotel.” And, indeed, getting an “unfair share” of “what’s left” is near the heart of the matter. Schulze’s remarks also remind us that instant, mindless cutting of R&D or training or salesforce travel in the face of a downturn is often counterproductive—or, rather, downright stupid. Tough times are in fact golden opportunities to get the drop, and the longterm drop at that, on those who respond to bad news by panicky across-the-board slash and burn tactics and moves that de-motivate and alienate the workforce at exactly the wrong moment.

Tough times indeed require tough and unpleasant decisions—but thriving, not just surviving, is an option for those who mix wisdom and boldness of leadership with transparency and maximized employee involvement and engagement. Without suggesting that there is anything humorous about the pain that bad times cause, one can say that “this is when it gets fun” for truly talented and imaginative leaders at all levels and in businesses of every sort and size!

I frequently hear words of doomsday and panic from those I’d expect to hear it from – backseat drivers and people who’ve never really done anything, or who’ve never really  been there and done that. From people who’s claims-to-fame are an MBA, or who rode a wave at a time of great opportunity and when everyone else was riding the same wave. I hear words of fear, reactionary language, strong opinions from those who don’t see beyond their own horizons, from those who lack vision. Yet I hear words of encouragement, of calmness, an almost harmonious philosophy, more proactive and forward thinking language, and open-mindedness from those who have been there, who have done that, who are glass-half-full, those who have vision.

The hard times in life test people – test our instincts, like our will to survive. Hard times test our humanity, shape us into who we are. Hard times make us stronger, but only if we choose to fight.

Companies are no different. We must choose our battles wisely, but we must forge ahead. We assess the battlefield, have a battle plan, fortify our properties, and attack the weak spots of enemy lines. We put the sun to our backs to blind our competition, and we fight! We do not run! We do not hide! We attack in waves, one powerful wave of attacks after another.

Entrepreneurs, you’ve arrived at this destination by your own choosing! You cannot control the climate, or the environment, you can only control your reaction to it. Smarten up, stiffen up your spines, and get to work! When the going get tough, the tough get going. Fight! These are opportunities!


I made a mistake this weekend – I forgot about balance and paid the price. Actually, it’s not so much that I forgot about it, rather that I neglected to enforce it for myself and I know now that it’s been happening for a while. If there’s one thing that’s certain about these stressful times, with the economy and, for me, with CitySquares being at such an exciting precipice, it’s more important than ever that we all keep a healthy balance in our daily lives. Everyone is a bit more on edge these days than normal. People are inevitably going to be a little short-fused, or edgy. Myself included.

As an entrepreneur, my work tends to take over everything in my life – literally everything. When I hop out of bed in the morning, it’s game time. In fact, I don’t sleep much, because in between sleep phases I’m still gaming. When I sleep, I often dream of work. When I’m in the shower, I’m thinking about CitySquares. My iPhone is only an arm’s length away, always. Throughout the day I’m full-on. When I get home to see my wife, I’m full-on. When I eat dinner, when I watch TV or a movie, when I’m out and about, my mind is spinning about CitySquares. I may fake it well, but I’m constantly working. It takes a lot to bring me back down. Like, horse tranquilizer strength to bring me down.

Now, this is mostly expected from an entrepreneur and founder of a company – it’s actually normal in the world I live in every day. But as it pertains being a human and living out my life, it’s not normal – it’s harmful. It hurts. It hurts my relationships with others, my mental health, emotional and physical health. It’s literally caused me health problems – some I’m watching closely. In very rare circumstances it can affect others, even hurt them.

This weekend I had an eye-opening and very plainly realized that I’m on a path to self-destruction if I don’t correct this right now. I must get back to balance. I have some hobbies that I’ve neglected lately, some friends and family that I’ve neglected, some passions that I’ve ignored. Maybe I need a long weekend away on a beach somewhere. I’m not sure, but I’m going to figure it out fast.

As with everything in life, there must be moderation. And that goes for entrepreneurs too! In this fast-paced, web 2.0, always-connected, get-ahead entrepreneurial way of life it’s so easy to get lost in it all.

I believe it was Buddha who said, “everything in moderation, even moderation.”

‘Nuff said.

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

Startups are Families

CitySquares isn’t the first startup company I’ve been a part of, but it’s certainly the most special, because it’s my creation. This company has taken on a life of its own. It took some time for it to develop this heartbeat and to get this personality. No doubt it’s is an entity all to itself, more so than just a tax ID with the government. From the very beginning in August 2005, a culture was starting to take shape. We’d sit at my kitchen table in Davis Square and talk about what this could be, how it would work, what kind of future should we plan for, what kind of company do we want this to be. Even when it was just three of us, and even when we had sales people making minimum wage out on the streets all day, every day, it was forming a personality. It was largely out of my control too. I could influence the culture a bit, just by being a part of the business, and setting the vision. But the personality, the culture that the company takes on is essentially a manifestation of the personalities and cultures brought into it by its staff, even those that come and go. Continue reading Startups are Families


resilience |r??z?li?ns| |r??z?lj?ns


• (of a substance or object) able to recoil or spring back into shape after bending, stretching, or being compressed. See note at flexible.
• (of a person or animal) able to withstand or recover quickly from difficult conditions : the fish are resilient to most infections.

ORIGIN mid 17th cent.: from Latin resilient- ‘leaping back,’ from the verb resilire (see resile ).

It’s one thing to say someone or something is resilient, but it’s another to demonstrate resilience. Resilient would definitely be an adjective that you could apply to CitySquares and to it’s people. We’ve known that for some time, but as the company grows we continue to be tested, and we continue to pass those tests.

Like any company we face challenges, hurdles, obstacles. Some of them we face daily, others only rarely. Along the way this past quarter a few challenges popped up, big ones. Despite any number of factors that might work against us, we overcame them, we bounced back and with smiles on our faces. Executing falls on everyone’s shoulders, especially in a start-up company. It’s up to everyone, the entire company, the team, the tribe, to work together, pull their weight, and overcome these challenges. It begins and ends with the members of the tribe! And as the old expression goes, “you’re only as strong as your weakest link.” Well, this is one strong chain.

While this past quarter we overcame the challenges in front of us, we face others now. But we face them with a new found confidence, and with new knowledge and experience behind us. Over time we’ll face similar challenges with more wisdom, and we’ll even be able to prevent them from happening. That’s really the big challenge isn’t it? Learning from these things, gaining the experience, applying that wisdom correctly.

The Good Times & The Bad

In the eight years or so that I’ve been running businesses, and in the twelve years or so that I’ve been managing teams of people, I can wholeheartedly say that I’ve always been able to balance a leisurely work environment, one that’s bullshit-free, and one that’s productive as well as fun, with being a boss, a manager, and sometimes the bastard who doesn’t take any shit. I think the folks who’ve known me longest, and who’ve worked for me longest, know the kind of ship that I run. In fact, we just hired a guy here at CitySquares who worked for me at my previous company and part of the appeal was exactly that, “the type of ship I run.” As a manager, or a boss, or a CEO, sometimes you have to be the bad guy. It just comes with the territory. It’s hard being a manager, and anyone who says that being a manager is easy doesn’t really know management. As a manager, or a managers manager, or a CEO, you’re constantly being scrutinized. Everyone is watching and it can be a very tough crowd, with little forgiveness.

At CitySquares we have a hell of a good time. I’d say that about 80% of the time the mood in the office is good, music is playing, everyone is very productive, efficient, and everyone is communicating well. Everyone gets along well, they take their jobs personally, and they also hold themselves and each other accountable. These are traits in an organization that are extremely difficult, if not impossible, to simulate. It’s either there or its not, you can’t fake it. And that kind of morale, productivity, efficiency, etc, starts with management. We’re also fierce and extremely competitive. We’re relentless and we love the scent of blood. That comes with being a sales-oriented business. But we can be hubris too. That tone, and that mood, also starts with management.

For the remaining 20% of the time, the mood can range from stressful (i.e., the end month sales pressure) to downright high-anxiety and tense. Those are the times that you see how tough you are as a company, the times that you see how resilient your staff are, and who rises to the occasion, and who does not. It’s that 20% of the time that tests the will of the company and of those within it. Can it prevail? Can it stand back up, dust itself off, and get the job done?

Things can change very quickly in a startup. One day you can be flying high, rolling along and just steamrolling through goals and achievements, and laughing all the way, with a cigar in the corner of your mouth, and a bottle of champagne in hand. All that can change in an instant. In a startup, there is extremely little room for error. In fact, I prefer to take a no-room-for-error approach. Missing goals is not an option, and missing deadlines is not on the table. Mistakes can happen, they always will, and that’s OK, as long as we learn from them, and apply those lessons to the next day. When we fail to do that, to learn and then apply lessons, the mood can quickly change.

I hold this company, and its personnel, to very high standards. It’s those standards, I believe, that have gotten us to where we are today. Those are standards that everyone here understands and practices. The company can have all the fun in the world, listen to music, have a weekly happy hour, play games, go bowling, have company pools and contests, and eat, drink, be merry every day. But the moment that we stray from the plan, the moment we start to fall behind, that’s also the moment that the seatbelt sign goes on.

Often times people will ask how things are going at CitySquares. My answer, lately, has been the same: “Things are going very well. In fact, things are going so well that I’m uncomfortable.” That’s my take. I don’t want to be comfortable, and I want to be two steps ahead of where we should be. I want to see the clouds on the horizon, not caught in a hurricane, fat and drunk.

So it’s important that at a startup company that everyone keep perspective and remember, it’s a business. It’s OK to have fun, but at the end of the day, you have to take the good with the bad.