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.

A Tough Week

On a personal and professional level, this was one of my toughest weeks since the company was launched in the autumn of 2005. It was made especially hard because this week saw the departure of an employee who’s been with us since the start. It was awful in many ways and I found myself physically affected by it to the point of nausea, loss of appetite, sleeplessness, and when I could sleep, I had nightmares. It was truly a shitty week.

Additionally, I had to pitch the board on something and it didn’t go over with showers of rose pedals and applause. C’est la vie – I get my 2nd swing at it in a couple of days.

On a broader level, not just isolated to this week, we’ve had a hard time finding qualified sales people and in a couple instances made offers to people who just decided to not show up on their first day. Nice huh? It seems, though, that the dust has settled now. We’ve a couple new people who started with us this week and they appear to be taking well to their jobs and to the company culture – two things I watch very closely in those first few days.

Yet, Tuesday we had our monthly company lunch and morale is good and healthy! At lunch we went around the table and told stories about our most embarrassing work moments, or most demeaning jobs. There were some good stories told!

We’ve got a marketing intern starting with us on Monday and I’m actively interviewing to fill the newly opened role. We’ve got two more sales people scheduled to start over the next few weeks.

Anyway, the point of all this is that my job, for the past couple of years at CitySquares, has been entirely about building a business and a company, and it still is. We’re in ‘build’ mode, there’s no two ways about it. I enjoy that work greatly. Now that our staff is in the double digits my job is becoming increasingly more about managing the organization. I also enjoy that work greatly. I think I’m good at both of these things, which is why, ultimately, I enjoy being an entrepreneur and CEO. My previous company saw about 12 full time staff at it’s peak, but dozens of contractors around the country, nearly all who reported directly to me. I also was the direct contact for most of our customers. I greatly enjoyed that work, the hustle of it all. It makes me wonder too though, about those entrepreneurs that aren’t able to make the transition from founder/builder to manager/CEO.

So back around to tie it all off – it was a tough week, the worst yet. Unfortunately, as a manager, tough decisions need to be made. Unfortunately as a CEO sometimes you gotta take a few jabs from your board. But at the end of the day, this is a business, that’s the bottom line. And at the end of the day I need to be able to look at the books, look at my board, and look at my staff confidently – knowing that I’ve done the best job they expect from me. I have to be accountable. It’s not easy, I didn’t sign up for easy. And I also need to be able to look at my own reflection and know that I’ve done the best job I expect of me. And the two are not separate – they are the same.

So to wrap it all up I thought I’d share a funny video that someone sent me on Monday – the timing was great. This person had no idea that I was entering a shitty week either, just really good timing on their part.

See you on the other side

2007 was a pivotal year for me in so many ways, mostly professionally. But as is the case for an American entrepreneur, my personal life hinges on my professional life. It’s now 7:30 on New Years Eve and Ali and I are settling nicely into our new home. Carmina Burana appropriately just came on the speakers. I’m working on a tasty Belgian beer, but it’s not quite cutting the edge. What edge? The front edge of 2008.

I’ve been a little edgy today (not unusual for me – I’ve been called “edgy” before, among other things), but unusually edgy. I feel slightly less in control than I’ve felt for the past few months. 2008 is supposed to be a big year for local search, and if Citysquares can innovate properly, can achieve some measurable success with sales, and expand aggressively (yet cautiously) we’ll be in excellent shape. But those are three big tasks for a maturing startup company. Make no mistake about it – I’m confident. I’m confident, first and foremost, in my own abilities to kick some effing ass. That’s not blind confidence (a.k.a. cockiness), that’s self-assured confidence – it’s just a matter of fact – I will get this done.

I suppose what’s got me most anxious is the changes. The foliage is changing, for the better. When the foliage changes, I get a little fucked up. It’s the unpredictability of it all, the change from comfort to the unknown that gets me a little uptight. It reminds me a lot of Michael Gerber’s E-Myth – the Technician vs the Manager vs the Entrepreneur. When I first read Michael’s book, back when I was running Atomic, I was struggling with the different ways an “entrepreneur” can run a business. The book was recommended to me and I read it front to back, listened to the audio book on the subway, and soaked it in with an open mind – then I did it again. I learned so much! It wasn’t long after that I started Citysquares – with an entrepreneurial mindset. And it happened naturally.

So here I am today, a little over 2 years since starting the company. We’ll be at 13 employees in January. We’re starting our expansion. The strategy is really being set into motion. And now, I’m like a visiting team’s starting pitcher facing some tough batters in the top of the 3rd with a tie score. It’s a pivotal time in the game and I’ve got to perform, got to give my team a chance to get up to the plate – but I’ve also got to keep plenty of fuel in the tank to finish the game.

I’m ready. I’m anxious. I’m motivated. I’m eager. I’m fuckin pissed off. See you in ’08.

Update (long overdue)

Last weekend I was fighting a nasty cold and decided I’d post an update up here. After typing and editing for what seemed like an hour, I accidentally hit the Backspace key and found myself going backwards in my browser, and when I clicked forward, my blog post was gone. I was pretty pissed off. So, I’m feeling better this weekend, less fat-fingered, and I’m going to take another shot. Here goes it. By the way, this is long, but as always, in the spirit of transparency and honesty, I’m going to give you all I can.

(Quick side note: Be my buddy on Citysquares.com! You need an account.)

Update on company morale: It was very interesting. About 4 weeks ago I started to pick up on a vibe of discontent among our small staff. I honed in on it for a couple weeks, listened closely and found it was true. I think it started right after the launch of the new site. The staff was really hyped up about the new launch, but it got delayed by a week. That was the first disappointment. As a result of all the enthusiasm around the launch, the staff was also hyping customers and partners. The launch went a week later and it went well, but as usual, not without bugs. And for all of the Citysquares staff, except for me and Bob, this is their first startup experience, certainly their first web startup. So they felt a little disappointed I think, because of the delay and the bugs, and because the fizz in the bottle didn’t add up to the big explosion everyone was expecting. I realized that I had to become more engaged with everyone and address these matters one by one. I was stuck in my office, helping Bob and Justin fight fires on the site. I needed to stop that, and get out in front of the team and put their minds at ease and share the plan. After opening the lines of communication, top to bottom, side to side, and working with Bob and Justin, first, to set the plan, and then once it was communicated across the company and other channels, the stress went away and everyone started to breath easier.

On top of all this, as the company continues to grow, new personalities enter the equation and new relationship dynamics sprout and change. I suddenly had flashbacks of days at prior startups, and how it’s so important to water the seeds of those relationships and keep the soil fertile, and also to clip off the thorns. When you cut right down to it, the company is only as good as our people. And people, well, need people. We spend more time with each other than we do our own families, for the most part. So it’s critical to build this company from the ground up with deep rooted relationships firmly in place – that starts now. I firmly believe that those relationships, those bonds, can be the source of greatness for the business, or the source of something devastating. Anyway, morale has gone from OK to great, and mostly because the stress of the launch is gone and also, we’re doing more together, as a company. For instance:

  1. Beer Fridays.
    Every day at 4pm, we have a beer and wind down the week, we joke around, we chat, and relax the shoulders and posture – just chill. Last week we had our first, and while most people actually stayed at their desks, the vibe was very loose. People were joking around, instant messaging each other, and friends, busting each others chops a little and letting off a little steam. Last night, we all went next door to Gaslight for a drink. It was good – lots of laughs, and more letting off steam.
  2. Monthly company lunch.
    Once a month, on a set day/time, we all either head out to lunch together in town, preferably nearby, or we order in. The purpose of this is the same as beer Fridays – don’t take things so seriously, get out from behind the desk, stretch the legs, relax the shoulders, have a little fun, and build bonds. But also, to talk about company matters, changes to any policies perhaps (yes, this web startup does have policies), and to just open up the lines of communication. This is very important. This month we went to JJ Foleys Cafe and it was a good time. After lunch, the office was in 5th gear – I was very happy to see that. This is going to last until the company gets so big that it just gets too expensive and we’ll have to slim it down a bit. But for now, it’s totally manageable.
  3. Holiday outing
    So we were all thinking that we could have a big Citysquares.com holiday party. Maybe we’d invite customers, users, friends, partners, etc. But the more I thought about this the less practical it became. Just too much, right now. Maybe sometime next year when there’s a better reason. So we opted instead for a company outing. We’re still trying to figure out where, but we’re thinking of going to F1 Boston, or to a paint ball range or something, and then a big lunch in the north end. Not quite sure, but this is the direction. We’ll do it on a Friday, perhaps December 14th. We’ll shut down the office, leave at like 1 or 2pm, and go have some fun. This way, a) it doesn’t impede on people’s personal time and b) it’s a free half-day off.

Well, that’s a big one. It’s pretty detailed but I thought it was a good entrepreneurial topic that you might enjoy.

Update on the new site launch. The site launch went well, albeit late. And like any product launch, it didn’t go off without a hitch – it had it’s fair share of bugs. The feedback from folks was quite immediate and ranged from raves about the new design/look/feel, compliments and sometimes confusion about the new navigation, to complaints about certain functionalities and features. Things that people loved included: design, navigation, breadth of the site, fusion of some new social features with local search. Things that people didn’t like: search, navigation, user profiling (People Profiles). Bob and Justin were quick to fix some navigational issues, and that continues to be a work in progress, and they also quickly fixed some of the people profile problems that we launched with. Search continues to be the biggest problem, and the new search functionality is on track to be implemented at the end of November. That’s probably the biggest thorn in our side right now, as it pertains the site experience. Bob and Justin are also working hard to revamp some of the customer profile pages and upgrade some UI stuff, specifically on the city/neighborhood home pages. Too much real estate is being used by the map and the businesses are far too low. This is going to be fixed next week I believe. As always, these things are to be expected and improvements are going to become more frequent and rapid. Bob and Justin have some very exciting plans for the site, once these bugs and fires are take care of. All things considered, the new site has impressed many and is a huge upgrade from the old site and we’re very pleased.

Sales. As I’ll tell you over and over again, Citysquares is not a technology company – we’re a sales and marketing company. That’s where we invest most of our dollars. Our goal is revenue, not widgets or Facebook apps (at least not yet…). Much of my job is to oversee these efforts, and so far Citysquares is doing a hell of a job with sales. Last month we had another record month. I am becoming more and more impressed with a) our sales manager Phillip, and b) our two full time sales people Kim and Jason. The three of them work extremely well together and when they get into 5th gear, boy are they good.

We had a strange incident with the sales team this week actually. We hired a new guy who started on Monday. He quit on Friday for “another offer.” Phillip was pretty ticked off and just had him leave right away, and I would have done the same thing. Everyone took it very lightly and even laughed it off, but we have to be more careful and listen to our guts a little more. I think most, if not all, of us had a feeling about this guy. It’s caused us a bit of frustration because now we have to fill his seat and that takes time and money. It’s OK to laugh about this once, but we need to be sure this is the last time.

Other things. There are lots of other things I could talk about in great detail, but this post is going on long enough. I’ll run through a few things though, briefly:

  1. HR – Yeah, yeah, we’re only 10 people, but ya know, it wont be long until we’re 20 and handling HR matters is going to become a real pain the ass. We offer competitive salaries for everyone, stock options for most staff, and a great Harvard Pilgrim Health Care HMO plan. But two of the employees’ families are growing, we’re hiring more people and their needs are different, and we need to be able to a) offer more benefits and do so cost effectively, and b) offload some of this management. We talked with AdminiStaff. Frankly, I was not impressed. They couldn’t give me a straight answer as to how much their services would cost me, per employee. Isn’t that the bottom line??? Not for them I guess. We are talking with TriNet – much much better! We’re running some numbers and we hope to be able to use them starting Jan ’08.
  2. Marketing – going well. We decided to have less control over the tactical approach to the marketing, we accepted the fact that we don’t have a resident marketing expert and we should really let our partners have more control over the approach, and get a little less hands-on. We should help establish the strategy, the goal, the vision, help build and approve the plan, but then let our expert partners run with it. This is why we have these partners. We decided on this about 3 weeks ago, and it seems to be working well.
  3. Traffic – growing nicely. Alexa sucks. Quantcast is pretty cool. Google Analytics is rockin. I trust AWStats the most though. Uniques are growing nicely, repeats are steady, page-views are already at an all time record high this month. I want to see much more though. We’re working to tweak our SEO, and improve upon our content strategy, and marketing is a big part of this, so are partnerships with content and media partners. Speaking of which…
  4. I hope to announce a new and exciting content/media partnership in the next couple of weeks.
  5. Hired an office manager, Amber, a couple weeks ago. So far that’s working out very nicely! I can actually get back to working ON the business, not so much IN the business.

Well, that oughtta do it. Wow, this was a long post. I guess that’s what happens when you let it go so long. Sorry for the silence everyone!

A Taste of Progress

Well I have to admit that today was probably the first really great day here at CitySquares. Today just felt like progress was in the air. From early in the morning through this hour things were just happening, all day. Phillip and Zac were just kicking ass today and they took June sales from good to great. Bob is really cooking on the IA for the new platform, the comps, and readying for his presentation the BOD on Monday. Chris is really starting to get the marketing and PR stuff moving and some really great ideas are in the oven. Our advisors are coming in tomorrow for a meeting and to discuss lots of things.

One of the coolest things that’s starting to happen now is we’re starting to really perform as a team. The office is just abuzz. People moving around, phones are hot, faxes coming in and going out, ideas are being discusses, priorities are being targeted, fires are burning, and everyone is getting along really well. The energy and morale is very positive; lots of smiles, and there’s just as much dialogue and debating.

Today felt great all around. There will be highs and lows, but my gut is telling me that this is just a taste of what’s yet to come.

TechSpace is Good Space

When Citysquares first launched as an idea I was still running Atomic Enterprises. We had an office in downtown Boston, near the Orpheum Theatre and across from the Park Street T station. It was a great location. The office left a lot to be desired though – there were break-ins, fires, junkies lingering outside, criminal activity in front of our door, and lots of shadiness.

Back in September of ’06 we (Citysquares) moved out and went virtual. Getting an office wasn’t a priority for a while, as it was saving us good money and we were still productive. But it didn’t take long for morale to take a dive. That was tough, really tough at time. Bob lives in Groton, about an hour away, and Chris, at the time, lived down the street from me. He’d come to my house and work in the basement with me – awkward, yes, but necessary for us to maintain sanity. Bob continued to work from home, in Groton.

Over time, morale took a big dive and we were losing productivity – starting to get frustrated with the situation. An office was immediately necessary but we really couldn’t afford anything, – then came the funding.

We were in the market for an office. Having had an office in the past I knew the operational headaches that come with a regular office – a lease, utilities, Internet service, phone service, parking, security, cleaning/maintenance, and all of the other bullshit that comes with it. Then, you end up spending 10-15% of your time dealing with all that – paying those bills, dealing with outages, changes, etc etc. Argh! No thank you! I need to be productive. We, as a company, need to be productive. A shared office space would be ideal.

We looked at HQ, Regus – no thanks. Too corporate, stodgy. If we were a law firm or a brokerage of some sort, sure why not. They were also pretty darn pricey. Then we checked out Cambridge Innovation Center (CIC), in Kendall Square, Cambridge. Let’s just say we weren’t treated too well so that didn’t work out. We fell in love with TechSpace in the South End, but we weren’t too thrilled with the location and needed a little added incentive.

We dealt with Paul McBride, the site manager at TechSpace. Paul was very assertive at winning our business. We put up a bit of a fight and weren’t totally convinced that TechSpace would suit our needs. We had very specific and technical requirements, especially pertaining telecommunications. Paul bent over backwards for us and proved to us that we’d be a valued tenant here at TechSpace. Eventually he had to let go and leave us to make the decision, which we did after a ridiculous amount of internal discussion.

We moved into TechSpace in one day, about a month ago. We’re extremely pleased! Paul has proven to be a fantastic resource for us here, and the admin staff, Myrna and Grace, are top-notch. There’s a cafeteria-like set-up here run by a classy old-school Southie guy named Mike. He does a great job of serving up breakfast and lunch every day here.

The atmosphere at TechSpace Boston is creative, funky, fun, communal, casual, techie, dot-commy. It’s a great place. We’ve got these giant windows at our desks that open up – thrilling! We’ve got access to 4 bonded T-1s, chilling! Four conference rooms, a parking lot, our own private suite, a full IT infrastructure, good people in the neighboring suites and in the hallways, and most importantly – we’ve been super-productive since the day we moved in here.

TechSpace is a great space. If you’re in startup mode, or if you’re a small, innovative and creative company, check out TechSpace at 580 Harrison Ave, 4th floor, in the South End of Boston. Call Paul McBride at (617) 275-7000. He’ll treat you well if you tell him Ben sent you!

2007-05-31: Quick update to this. I just learned that one of the bigger tenants here is moving out in June. Lots of new space available. We may have to relocate down the hall. But also, I just learned that yet another dot-com is moving in here. This is really turning into a nice spot for Boston dot-coms!