Your Entrepreneurial Spawn

Recently I found myself going through a bit of a ‘thing’ – in a good way. Certain forces within the confines of the CitySquares fortress have forced me to think about some exciting opportunities on the road ahead, as well as some challenges that I’ve never had to face before. And just as I’ve had to think about these good and exciting things, I’ve also had to think about worst-case-scenarios, as the market and economy put a damper on things and forced us to have backup plans. These things, coupled with a few family emergencies and close-calls, have caused me to shift my focus a little bit. You know how if you look at something bright for a little too long it can stain your vision for a short while? Well, think of entrepreneurship as the source of bright light, and the rest of reality as the backdrop to the stain. Let me explain…

As this company grows and gets closer to cash flow positivity, and as we continue to rack up traffic numbers, questions come to mind, like, “what next?” and “what does this really mean?” On the flip side, when the economy nosedives, and our primary markets stop cooperating so well, I’ve also been forced to ask those same questions but in a very different context. What a conflict! Furthermore, there was a very close-call with a member of my immediate family. These personal/family moments have a way of acting like gravity and pulling you down to earth very fast and hard sometimes.

So, these things have forced me to pause for a bit and think about who I really am. Because in either scenario, entrepreneurial success or failure, I am left with one single common denominator – me, myself, and I.

When you a third of your life dedicated to entrepreneurship, you inevitably become party defined by it. Things change. Your perceptions change, as well how others perceive you, including friends and family. Suddenly you’re no longer defined by the things that always defined you, but now you’re defined by what you spend 24/7/365 on – your business, your entrepreneurial drive. You are truly and without a doubt, true and through, an entrepreneur.

This changes you, and I’m not so sure it changes you for the better. Why? Because you lose a part of yourself. It’s unavoidable. When you put so much of yourself into one thing, for so long, you inevitably have to sacrifice other parts of yourself. It’s simply impossible to be an entrepreneur without sacrificing other parts of your Self. And when the business you create starts to take on it’s own life, its own characteristics, its own heartbeat and blood flow, suddenly you realize that it’s not a part of you anymore, it’s an entire entity unto itself. This entity is a being, if you will, that is the very personification of your entrepreneurial passions – its the result of it. It’s your entrepreneurial spawn, and it embodies everything that defined you.

I experienced this event, if you will, over the past several months, or rather, this epiphany. I had to ask myself, what if this thing actually, really, seriously takes off!? What if it really, actually, seriously becomes something!? What if it actually meets or exceeds my most realistic expectations? Or contrarily, what if it flops? What if the economy strangles it? What if outside influences and forces suffocate us? In either event – what happens to me? What do I do? Who am I, then?

So, here I am now, writing this post post-entrepreneurial-identity-crisis, I think. And I also think I’ve figured it out so some extent. I’m working hard now at trying to gather some of the missing pieces back together because I am not defined by my business, by my profession, by my entrepreneurial passions. I am defined by other things, who I am, how I treat people, how my family and friends view me, how my community views me. That is who I am, for better or for worse. I’m getting back to more balance in my life, and so far, I’m loving it.

The moral of the story is probably obvious – but just for the sake of clarity: As an entrepreneur, do not lose yourself. Do not lose sight of who you are and of the big picture, and of what’s really important in life. Maintain a balance in life. Many many years from now, when you are on your death bed, breathing your last few breaths, you will not utter words about how you wish you made more money, or how you wish you accepted that VCs terms, or shouldn’t have sold your company to Big Corp. You will think about family, about friends, about places you’ve been in the world, about those most simplest of things. So enjoy what your doing right now, and if you’re not, make a change.

I’m still trying to figure all this out, I definitely don’t have the answers. I may never have the answers! This is probably one of the big questions in life, ya know? I just know that I found a new perspective, and it’s working in the most meaningful ways.

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Right Now…

Right now is the most important moment in your business.
Right now is the only chance you’ll have to have right now again.
Right now is the moment you’ll wish you had in a few minutes, a few days, or a few years.

Go thank a staff member for something they deserve a thanks for, right now.
Call that investor you’ve been nervous to talk to, right now.
Ask that board member to hear you out, right now.
Thank your better half for putting up with you, right now.
Call a customer to say hello and offer your help with something, right now.
That thing you’ve been putting off? Yeah, do that, right now.

If you’re an entrepreneur, and you’re not doing something important for your business, for your company, right now, than piss off – because you’re wasting your time, and your wasting everyone else’s time.

I’ve been seeing a lot of tweets, emails, and so forth, lately from “entrepreneurs” who are moaning and groaning, and carrying on. They’re quite vocal about how shitty things are for them, how tough it is out there for them. YOU POOR THING! How can the rest of us help you?

Bullshit. Get off your ass and deal with it, like everyone else. Help yourself, like you need to. Earn it, like everyone should.

Sometimes being an entrepreneur sucks. It’s not a dream job, you’re not an astronaut – even astronauts don’t want to spacewalk sometimes! Sometimes it can be thankless. Sometimes your sacrifices go unnoticed, sometimes your just not happy. But that’s part of being an entrepreneur! You made the decision you sicko! You’re the one who’s been calling yourself an entrepreneur, networking, grooving and moving, shakin’ shit up, makin’ things happen. But now, what? Times are tough, and you’re kickin’ pebbles around like someone just stole your lunch? Bullshit! Get off your ass and get to work! Maybe you need some time off… WRONG. Get to work.

It’s not how you handle the good times, how much fun you had when things were great, how great you looked in that picture for that article, how awesome the feedback was at that demo, or what Arrington said about your business model at a party, it’s what you do when things are hard, when leadership is needed the most, when those around you judge you the harshest, when your product is screwed up, when people aren’t around, when even the local paper forgot who you are.

Right now is the most important moment in your life. If you’re really an entrepreneur, you’ll close your browser right now – or close your email client – and you’ll do something you’ve been putting off right now, you’ll snap out of it and get with the program – right now!

P.S. – That’s Eddie Van Halen – a reference to his song Right Now

If You Can See It, You Can Get There

I believe that if you can see it, you can get there. I was reminded of that notion this morning. I was on my porch early this Sunday morning enjoying the crisp silence of this last day of summer. I looked up and saw a beautiful half moon staring down at me against a sharp blue sky. I stared at it for a moment and remembered how close the moon really is to us, no matter how far away it might seem. But it’s all relative isn’t it? I imagine that during the Apollo missions NASA said the same thing to itself – “We see it. It’s right there. We have the ability, we have the technology. We understand the laws of physics. All we have to do is get there.” And sure enough, one step at a time, they not only got to the moon, they not only orbited the moon, they not only landed on it, they walked on it. Then they drove vehicles on it. Not once, but several times! All it took was some technology, some ability, imagination, innovation, teamwork, and belief in success.

(Wow I just made the Apollo missions sound really simple didn’t I?)

I was raised to believe that anything was possible. Both of my parents are good like that. No matter what crazy idea I had, they supported me, as long as it wasn’t harmful, but they didn’t indulge me too much either. When I wanted to be a fighter pilot, they supported me. I’d study the G force and read about Chuck Yeager. When I wanted to be a major league pitcher, my father taught me proper form and challenged me during little league practice. I could go on. The point is, I tried, and I worked at it very hard. No matter how far off the destination seemed, I believed in myself and I had the support of my parents. I may not have been capable of being a fighter pilot, because of my poor eyesight, but that didn’t matter – anything was possible. My fastball was pretty nasty, but that was all I had. Yet I had the potential.

Entrepreneurship is very much the same way. Continue reading If You Can See It, You Can Get There

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.

My Definition of Entrepreneurship

Ali and I are moving to a new home in a few days, so naturally our current place a mess. Boxes everywhere, dust bunnies skating across the hardwood floors, the smell of packing tape is in the air, and the sound of tape guns can be heard from one room to the next.

I was packing up a room this morning, and I came across an old boombox. I noticed there was a CD in it. It happened to be Neil Young’s Harvest Moon, a slow, acoustic, melancholy album. Among the songs that came on was “One of These Days.” It really took me back – I mean way back. The last time I heard this song was probably in the mid 90s, on a snowy day just like today, with an old friend. A friend I miss dearly. There are many friends who I miss dearly. It’s ironic that the last time I heard it was with an old friend who I miss dearly. Among the lyrics of the song:

“One of these days, I’m gonna sit down and write a long letter, to all the good friends I’ve known…

I never tried to burn any bridges. Though I know I let some good things go…

From down in L.A., all the way to Nashville,
From New York City, to my Canadian prairie home,
All my friends are scattered like leaves from an old maple.
Some are weak, some are strong.

One of these days, I’m gonna sit down and write a long letter to all the good friends I’ve known, and it won’t be long.

Songs mean a lot of things to each of us, and to many there is nothing more powerful than a heartfelt song. Today I had one of those moments.I was reminded of so much – so much that I’ve tried to forget, so much that I’ve tried to move on from. And for the most part I have, but much of it’s still with me, mostly good stuff. I guess as life goes on, so much sticks to you, other things don’t. And we don’t get to pick and choose. All we can do is make decisions about right now. Those decisions influence those we’ll be faced with tomorrow.

I guess what inspired me to sit down and write this in the middle of packing is that it really reminded of what I’m working so hard for. I’m working for a better life – for myself, for my wife, for a family that I’ll build. I’m working to make sure that I’m the best person I can be. To live right. I didn’t set out to be an entrepreneur. I didn’t get a degree in business. It’s not intentional, this entrepreneurial thing. And It’s not about the money, it’s not about having a notch on my belt, it’s not about being an entrepreneur, or being connected to wealthy and powerful people, or an ego. It’s about building the best life I know how to build.

I’m glad I put that CD on today, I’m glad the song came on, I’m glad I remembered.

(Sorry for the cheesiness.)

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! 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 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!

Why I Will Succeed

I write this post with a heavy heart. I recently lost a close relative, in tragic fashion. As untimely as death is, this one really was untimely. My wife and I spent the past seven days with family in Florida and NY.

In the midst of all this I had a board meeting, some deadlines, and other work activities that still needed tending to. Thankfully my team at Citysquares had things well under control and I knew I could count on them to make sure things run efficiently and that the impact of my absense would be minimal. I found myself confident that I could be away from the office. Of course, having a BlackBerry sure helps.

Anyway, during the past several days, having the confidence that the company was running on its own, and disconnecting myself from day-to-day operations, in addition to mourning the loss of a loved one with my family, I found myself being reminded of why I’m doing this entrepreneurial thing. I was reminded not of fame and fortune, not of career advancement, not of fancy boats or cars. I was reminded of the importance of family. I’m 31 years old, I’m married. We want children. I have a big family, here in New England, in NY, and in Florida. I have a life to build and to live.

I’m doing this Citysquares thing for good reasons, reasons other than fame and fortune. The #1 reason is so that I can build a life for myself, my wife, my family. And that reason makes it all the more important that I succeed.

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.

Update and Apology

I must apologize – I’ve been neglecting my blog lately, something I promised to myself that I wouldn’t do. This is meant to be an update of sorts, and a promise to you.

So I’m sitting here in my new office, with my window wide open, looking out over the south end. A couple of residents are sitting on their rooftop patios reading, with their dogs sitting patiently next to them. Many thoughts are going through my mind. I’m thinking about my new Board of Directors, about Bob’s presentation that he’s doing soon, about sales, our new employees, about cash flow, about company morale and culture, about my own morale, and how strange it feels to not wake up on the edge of a cliff every morning.

Last night we attended a friend’s graduation party. She just graduated from Harvard and they had a nice BBQ with friends and family, in Teele Square. It was a nice time. I got to talking with her father about business, entrepreneurship and so forth. Turns out he had a big hand in revitalizing the Midwest during the rust belt era. Interesting guy. I told him how ever since we got funded how I’ve felt like I needed to clear my head and press my reset button and how it’s been a bit of a struggle. As someone who, through the government, seeded the entrepreneurial communities of the Midwest in the 70s and 80s, he had some wisdom for me. He reminded me of the importance of taking care of yourself – finding those things in your personal life that make you feel whole and not depending on your business to do that for you. It was an interesting discussion and it really opened my eyes. I continue to work hard, work my butt off, but I can’t help but feel like I’m still not doing enough – like I’m not working hard enough. I’m almost wondering where the pain is. It was almost 2 years that we felt pain and pressure and now that it’s gone, I almost feel like an abused dog that is no longer with an abusive family – confused, disoriented. I’m slowly coming out of it though too, out of the dizzy-spell. I’m starting to zero in on new and fresh priorities. I’m also starting to really enjoy actually running a company, not just a business. That’s probably one of the biggest changes for me – switching gears from running a tiny little business to running a company and having to manage it. Since winding Atomic down, I forgot what it was like to run a company, with employees, and with initiatives and a mission. I pretended, but I also forgot. Now it’s coming back to me. This is fun stuff. But it’s also not what life is about. It’s not the be-all-end-all of life. I must remind myself to take care of myself, to enjoy what I do and to take it seriously, but also to value my time away from the desk, from the laptop, from the BlackBerry. I must remember to sit on my own patio, read a book, hang out and just enjoy – well just enjoy.

Anyway, a bit of a ramble there, but hopefully that gives you a little insight into my lack of blogging lately – it’s been a period of transition and, like a typical guy I suppose, I keep it inside – I don’t express it – I try to work it out on my own (a little Dr. Ruth, or Dr. Phil, or Dr. Melphi for ya). But what I realized the other day was that by not blogging, I’m not staying true to myself or to my personal and professional mission, as it pertains Citysquares. I want to be transparent, honest, candid, and I think I’ve done so historically, but lately I haven’t. So, my apologies to you all.

I hereby promise that I will continue to honor that commitment to you all and to myself. This blog is not just about business, but its about people, about community. It’s about community outside the walls of my office, in the Ethernet and fiber and hard drives of the Internet, and about the community within the walls of Citysquares. This blog is about me, as your host and entrepreneur, and CEO in training. This blog is about grit, determination, honesty, hard work, passion, foolishness, and optimism. It’s about perseverance, guts, openness. I must honor that.

No more blog lag. (Like that? I just made it up. You can use that if you want.)