Ten Conference and Networking Tips

The Kelsey Group, or should I say BIA/Kelsey, held their annual Marketplaces conference this week in sunny San Diego. A heck of a show it was. So good that I probably was only able to sit in a handful of sessions. I say that because when I first started going to Kelsey shows in 2005 I was a newbie to the local scene, a newbie to local search conferences, and I probably sat in on 90% of the sessions, and soaked up information like a dry sponge. And that was the intent – to learn as much as possible, and then learn more. While my desire to learn at these shows hasn’t changed, my priorities have – it’s all about networking now and prospecting and establishing business relationships, of all types.

My colleague, Todd, and I had back-to-back-to-back meetings from even before the preconference started on Monday morning. By the time I left the hotel late Wednesday night, it wasn’t without three more impromptu meetings that kept me busy and well fed right up until I had to leave for the airport at 7pm. Here I am, 1:30 the next day, 60 minutes away from a follow-up meeting.

I wonder sometimes how some businesses in my industry (vertical? space?) are even able to stick around or grow without attending shows like these. These shows are sort of like annual or biannual checkpoints for many companies; are you still in it? are you thriving? surviving? ready to grow? growing? ready to do that deal you put-off last time around? changing models?

Since I started attending these shows almost five years ago now, I’ve seen many companies come and go. It’s exciting to grow alongside other companies, competitive or complementary or otherwise – it really is something to have those brothers and sisters to grow up with. It’s also sad and disheartening to see some of them vanish, never to be heard of again – to reminisce with others about those brands, faces, names, stories.

Perhaps the one point that really stands out for me though is how clear it is to me that these kinds of conferences and trade shows are so vital for me as an entrepreneur, and for CitySquares as a business. Some thoughts I’d like to share while they’re still fresh:

  1. Never judge a book by its cover. It’s so easy to dismiss a company because their slides may have seemed boring, or overly complicated, or the speaker wasn’t charismatic enough, or was even too charming. It’s easy to dismiss a company because their booth wasn’t fancy enough, or because someone was shy or anxious and didn’t have a drink at the mixer. I’ve been surprised so many times. Be bold, be brave – talk to everyone – but don’t be too aggressive about it. Just be there. Being there is the first step. Before you know it you’re deeply engrossed in a conversation and discovering common denominators.
  2. Don’t go to bed. I mean this. You didn’t spend your or your company’s money to go to bed when the best stuff happens. The best time to meet people, to learn, and to establish relationships and prospect for deals is during the hours following each day’s show. Whether in the bar, the restaurant, in the lobby, in the hallways, or outside the hotel at dinner and bar meetings – that’s when it happens. Simply put, be available. Don’t drink? No problem – but be there. You can make up the sleep on the plane or when you get back to your hometown. This way you’ll really be taking advantage of all the networking opportunities.
  3. Be real, be curious, be yourself. Don’t know about a topic being discussed, ask the panelists questions when the mic goes around. If the mic doesn’t make its way to you, stick around after the panel and track down the people you want to talk with. They’re at the show for the same reasons you are!
  4. Have business cards. I know it’s a no-brainer, but there is nothing worse then meeting someone and not getting their business card, or vice versa. Bring three times as many business cards as you think you’ll need. I can assure you that if you’re doing all of the above, you’ll use them. You may even need to run up to your hotel room to get more cards.
  5. Ask for time. If you meet someone you’d like to get to know better, or learn more about their business or talk about some ideas you have for working together, just ask them to meet with you. This is so easy – whether its an early breakfast meeting the following day, a chat in the hallway at a table, outside in the sun, at the bar that evening, over lunch or dinner, or even out in town – just ask them for their time. You’d be surprised. I’ve never been turned down. Sometimes you meet with someone and you find there’s just not a fit. OK – now you know! Time wasted? Absolutely not! More often than not though, there’s a synergy somewhere – but don’t force it either.
  6. Follow up. LinkedIn is the best way to follow-up. If you’re not on LinkedIn – get with the program! Really though. When you gather up all those cards every day, before you finally close your laptop at the end of the night, set them down, search LinkedIn for each person and write a personal message to them – remind them who you are and add some context to the message. A lot of names and faces get mixed up, business cards are just the reminder. Mention the topic you were discussing, be it business or even something casual that was discussed. It’s hard to remember who everyone is, but when you add context it jogs the memory and make it a lot easier for the recipient to accept your request. Follow up again a few days later with an email or a phone call.
  7. Go to the sponsored parties and events. Most evenings after the day’s events, there are company sponsored parties and gatherings. Go to them! If you find out its exclusive, and invitation only, just find out who’s doing the inviting and ask if you can attend – its rare that you’ll get turned down. Again, that’s what these events are for and the more people that show up, the better off that company looks – they want a good turnout! They want to be sold out and want people talking about it.
  8. Relax. This is especially important because no one wants to talk business 100% of the time. Be yourself, talk about where you’re from, learn about where others are from, talk sports, schools, family, hobbies. You’d be surprised when you do – often times you’ll find that you have a lot in common, and what was at first perhaps an awkward introduction turns into laughter, common interests or connections.
  9. Keep it simple. You’re wearing a name tag. People will look at it. After shaking someone’s hand and introductions the first question will be “so what does [your company name] do?” Don’t go into a 10-minute monologue about your special patent-pending technology that’s going to change the game and disrupt the whole business. First, no one likes to hear that their business is threatened by yours, and two, no one likes a bore. Be able to explain in less than 3-4 sentences what you’re business does – specifically what problem it’s working to solve. But don’t be secretive either. No one likes a spy or stealth company being sly.
  10. Know the right people. This is huge. Get to know a few people who run the conference, or who seem to know the right people, the folks at the booths, and others. If you see someone talking to someone you’d like to speak with, just ask for an introduction! They’ll be flattered you asked them. Knowing the right people does not mean shadowing people, tagging alongside them like a pet dog though either.

I hope these 10 points ring true for you, or inspire you to get out there more. And if you have any tips you’d like to add to this list, I’d love to hear from you, as would my readers.

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No

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.

Four Years

iStock_000002119635SmallToday is a special day for CitySquares. It was four years ago today that Bob and I launched the CitySquares.com website. We launched it with only 7 neighborhoods: Porter, Davis, Harvard, Central, Kendall, Union, and Inman. We actually held a launch party in Davis Square, invited local businesses, residents, artists, musicians and others to come and join the festivities. It was a blast! Check out the CitySquares.com Launch Party on YouTube.

When I look back at the entrepreneur I was four years ago and compare that guy to the entrepreneur I am today, I see two very different people. The entrepreneur in 2005 was much more naive and immature. I was so much more of an idealist, so much more pie-eyed, and I had a sharp tongue and quick trigger-finger that I had a hard time controlling. I’m still an idealist, I’m still pie-eyed, and I’m still naive and probably still a bit immature, but today I’m much more rooted, more grounded, more focused, and much more thoughtful about how I communicate and how I handle stress. That’s been a real battle for me – balancing life, making sure that my work does not define me, and hence dominate me.

So much has changed in the local search arena too. When we started many of the players we hear about today were as small as we were. Citysearch was really the only major player. We hardly knew what we were stepping into and local search is a more crowded and competitive space than I ever anticipated, and rightfully so, the market opportunity is massive. That kind of competitive environment has only kept our edges sharp and kept our eyes keenly focused.

The business itself has matured in many ways yet the model itself is still largely intact. That’s a real testament to the market opportunity and do our original business model. While the economy has presented a number of substantial challenges, we’ve been able to navigate our way through the choppy waters and in some ways its actually helped us sharpen our tools. It took us a few years to understand a number of the most fundamental parts of our business model and test them, and now, through some amazing partnerships and alliances we’re about to unleash some powerful solutions to a core problem in the marketplace.

Some of our identity changed over the past four years too. Unfortunately, as a small business with limited resources, there are only so many things we can accomplish. Our heart is big here at CitySquares, and we want to do so many things, want to give and contribute so much to society. If we were a non-profit, we could focus all of our time on these things, but we’re not – we’re a business. We’re in business for a reason, to tackle the market, solve a problem, deliver value for our customers, and along the way make money and provide a return for our investors. It’s not complicated, but realizing that took some time. I look forward to returning to those ideals at some point, be it through CitySquares or other channels.

My partnership with Bob has grown so much, and it’s just been awesome to watch him grow as a professional in parallel to my growth. Bob has stepped up, challenged himself, and done so through some very difficult circumstances. Not only has my partnership with Bob grown and blossomed into a very solid and loyal one, but our friendship has strengthened immensely. We may not hang out as much as we both would like but we don’t need to. I see Bob more than I see my own wife, and our friendship is evident to those who work with us and evident in our ability to work together through thick and thin.

I’ve also had the pleasure of seeing my colleagues grow as people, as life inevitably happens, and see them grow as professionals. Start-up life is not for everyone! That’s a fact! People who I work alongside, like Justin, Kim, Michael, Amber have proven themselves not just as contributors to the business and the company, but as loyal companions who continue to illustrate every day what tenacity and perseverance is about. They are the embodiment of these characteristics. They’ve also become friends and I’m so proud of them, and I’m excited to work with them in the months and years to come, and be able to provide for them and support them as they grow.

I’d like to point out some of the folks who’ve joined the team, stuck it out, and supported us in any number of ways. These people are not all necessarily employees, they’re friends to CitySquares too and their contributions to the company and the business have just been awesome. These folks continue to support us. The list is long, they know who they are. I’m not sure that this anniversary merits thanking them publicly, not quite yet – that day will come, I’m sure of it.

Along the way over the past four years we’ve made friends in the business too, with competitors, industry experts, vendors, service providers, consultants, press and media, and fellow startups and entrepreneurs. They’ve all added to the fun and the experience of CitySquares. Along the way we’ve also seen companies fail to succeed, entrepreneurs see their dreams crushed, and see the underbelly of entrepreneurship, startup life, and even see unethical behaviors by people and companies. These things have all taught us, made us stronger, and made us wiser. No different than a person going through life – learning lessons and becoming wiser in the process.

We’ve made mistakes, of course. I’ve made mistakes, no doubt. But today, on our 4th anniversary I can proudly admit that we’re doing something right. It takes a team to make that happen. No one person is responsible – everyone and everything listed above, and more, is just one of the puzzle.

So while an anniversary such as today’s is special, its just a milestone. There’s still so much work to be done. We can celebrate briefly, but the work continues. Every day is another day in the trenches and we need to advance our lines.

Onward and upward we climb, into our fifth year, heads held high, humbled, courageous, wiser, and focused more than ever.

Thank you for reading.

Angels are Good, Right?

6a00d83421dda453ef00e54f2e25558833-640wiFinally, someone is calling attention to those angel investor groups who charge entrepreneurs unfair amounts of money to pitch to them, and it’s not someone with a small microphone or with no following. Jason Calacanis has announced a “jihad”, as it seems, and is stirring things up. This topic is not a new one for many entrepreneurs but many more don’t know what all this means or what the fuss is out, and could use a bit of a primer on Angel investing and how it works. Given that most of the people who read my blog are aspiring entrepreneurs and those doing it for their first time I thought I’d shed some light on the subject. This is a bit lengthy, and not for vanity – I think it’s important to cover the subject thoroughly.

In our great country, the US of A, there is an overwhelming spirit of capitalism that trickles down to every street corner and school yard. Over the decades that spirit has become what it is today – the spirit of entrepreneurship. Once upon a time “entrepreneurship” was actually a rare thing, but today it seems that everyone knows an entrepreneur in one form or another. People like Bill Hewlett and David Packard, Bill Gates, Paul Allen, Larry Ellison, Steve Jobs and more recently Larry Page and Sergey Brin, among countless others, have made entrepreneurship what it is today – something that many actually aspire to become. It’s a radical new time, a very different one than those my parents grew up in.

One of the most misunderstood part of entrepreneurship is also one of the most critical parts – the part of fundraising. Over the past few years as CitySquares has raised money, it never ceases to amaze me how many people ranging from self proclaiming “entrepreneurs” to family and friends just don’t have the slightest concept of what raising money for a start up actually means. I’ve often heard some people inquire “wait, you got so-n-so to just give you money?” Just the tone of that question makes it sound like an entrepreneur is like a street corner pan handler begging for charity.

There are primarily two types of investors in the entrepreneurial and start-up worlds – Angel Investors (and Angel groups) and Venture Capitalists (and venture capital firms, a.k.a. VCs). I won’t be discussing VCs, just Angel’s, as they’re affectionately called. Angels are indepenently wealthy individuals who invest their own money in a business and usually do so in exchange for equity (usually Preferred Stock) in the company, or sometimes in the form of a Note – effectively a loan that will convert into Preferred Stock – loan companies help a lot (visit their website here). It’s not that complicated really. Some angel investors are professional angel investors, others are current or former entrepreneurs themselves. For example, one of my Angel’s built and sold his high-tech company to Yahoo! in the late ’90s for several billion dollars in stock. Another of our Angel investors has been an executive at several multi-national high-tech companies and did extremely well along the way as these companies exited (went public or were merged or acquired). Angels are also “accredited investors” as defined by the Securities and Exchange Commission. Sure, anyone with some money can make some investments and call themselves an Angel Investor, but to truly be an legitimate investor they really need to be an accredited investor (SEC definition, Wikipedia definition). I should also briefly note that the term “Angel Investor” is not a legal term, it’s more of a term of endearment that seems to have stuck throughout the years.

The most famous angel investment that I’m aware of is the $100,000 check that Sun Microsystems co-founder Andy Bechtolsheim cut to Google after watching Larry Page and Sergey Brin demonstrate their technology. The funniest part of this story is that the founders couldn’t do anything with the check for weeks because they didn’t have a legal entity formed under which the check was made out to.

There are other famous Angel investors like Andy, including Mark Cuban, Mark Andreessen, Ron Conway, and others. There are thousands of mostly unknown Angel Investors too. At the end of the day they all want the same thing – a return on their investment. Fair enough.

Some Angels work together, in what are known as Angel groups. These Angel groups typically form out of a shared sense of fostering entrepreneurship in a specific city or region or industry, among other reasons. The Angels might meet once a month to discuss their investments, invest together in companies, and invite startups to pitch them.

Here’s where it gets sticky. Imagine, for a minute, that you’re a young and budding entrepreneur. Let’s even say that you dropped out of college (like so many famous entrepreneurs have), you live in a house that you share with seven other young people, and you barely make ends meet. You make enough money waiting tables to cover your share of the rent and bills, to go out with friends, to take your girlfriend out, and afford yourself a cell phone and other bare essentials (by today’s standards). In addition to your part time job waiting tables at a nearby restaurant, you, in your spare time, have an affinity for cars and technology. And in this spare time you conceived a new technology that can power automobiles using carbon dioxide and have a very simple prototype designed. Pretty cool right? Probably a market for this? Maybe sell it to GM, if you can just prove that it works well, and that it’s affordable? Solve a climate problem? OK, so you need money. Your Mom and Dad are tapped, and they’re also pissed because you dropped out of college. Your uncle is good for $2000, so is your girlfriend’s parents. But you need more than $4000 to really build a working prototype, to hire someone to help you market it to car manufacturers, to hire a patent attorney to help you protect your Intellectual Property, etc. Sitting alone at a local pub you put some numbers on the back of a napkin and calculated that you really need $200,000 to get this idea off the ground and build a product and go to market. So… where do you go?

You have some friends who know people that have raised money from investors and had some success – you get the introductions and before you know it you’ve gone from playing Wii at home with your roommates to being thrust into the world of entrepreneurship, IP, angel investing, venture capital investing, business models, business plans, etc etc. But you need capital – plain and simple. Where are you going to go? You need to meet some Angel investors.

How do you move forward? You need to present your technology and business model to an Angel Investor, or more likely to an Angel group. There are many of them out there. A quick gander on the ACA website shows that there are actually a few right in your city. So you email an executive summary to these groups at their general email address and hope for the best. What usually happens at this stage is that you receive some responses from the Angel groups asking you to fill out an online application. The application process is a tedious but excellent exercise, forcing you to refine your concepts into just a few sentences, and to present your financial forecasts and capital requirements. The application process isn’t fun, especially when you have to do it for 4 or 5 different groups. Then, you wait. You wait while your information is being circulated among the angels or a committee. Then, after a few weeks (yes, weeks) you get an email telling you how wonderful your idea is, how excited some investors are, and you have an invitation to present to a committee representing the Angel Group. This is very exciting! But there’s a catch… you need to pay $750 first.

Now you pause, and you think long and hard. You ask yourself why you, a bootstrapping, young, starving entrepreneur who’s living off of peanut butter and jelly sandwiches, who’s put so much on the line, should have to cough up $750 just to present your idea to a committee! Absurd right? But what choice do you have… either you pay it and maybe raise some money, learn in the process, make some connections, or you don’t and hope something better comes along.

This is not unusual. Most angel groups want you to pay something to present to them. And they have their reasons, usually good reasons. But doesn’t it seem unfair? Absolutely! Despite their reasoning, it’s just unfair!

When CitySquares was barely six months old we paid to present to an investor group. It was our first time. It was almost the same scenario as I presented above. It cost us about $750. It was a total waste of money. We had a bunch of old timers vet us through their committee, and blow smoke up our asses. So far so good, or so we thought. Two months later we finally presented our business to a room full of 50 or so Angel investors. As it turned out, 90% of the people in the room had no idea what we were talking about. Zero, zilch, nada. They were in completely irrelevant industries, and in the twenty minutes or so that we were allotted, with a ten minute Q&A, it became painfully obvious that not only was our idea way over their heads, but that we’d just wasted $750 and a whole lot of time. And to make matters worse, it was soon made clear to me that this specific angel group had made very few investments and had zero successful outcomes.

How did that leave me feeling? Angry, frustrated, mislead, and a bit more broke.

This not just my story, but the story of many many other entrepreneurs who just don’t know better, who don’t know where else to turn, who have to learn the hard way. This is so much more common then most people realize. But it’s just part of the territory. Just as with any advisors I’ve attracted to the company, the best people I’ve come to work with are those that don’t ask for anything up front. They are genuinely interested in you and your business, and they want to help.

Now let’s get something straight – Angels are investors, and they’re in business as investors for one reason – to make money. Any other reason is secondary. So then, it seems that charging entrepreneurs a fee for pitching them likely has some justifying, right? Sure! But the entrepreneur doesn’t care what about those things. The entrepreneur is in business to make money, but he/she is not rich! And there’s the discrepancy. That’s where it becomes “unfair” – that’s where it’s skewed. Some Angel groups charge a lot more than $750. And there are even some people out there, predators, who prey on entrepreneurs and charge them for introductions to Angel investors. Fred Wilson points this out on his blog as well.

Generally speaking, Angels are not bad people and they’re are not milking entrepreneurs. I think its safe to say that this statement applies to 99% of angel investors and angel groups. It’s a scary place out there for entrepreneurs, especially when you’re being taken advantage of by wolves in sheeps clothing – and there are a lot of wolves and no shortage of sheepskin. The key, as with so many other things in life, is to sift through the bullshit, the noise, and use your instincts and intuition. That’s not easy, because all the signals can be confusing. In addition to using your basic human intuition is associating with the right people, good people, people who from the start do not want to take advantage of you, and people who are genuinely interested in helping you move to the next checkpoint. CitySquares was fortunate enough, after learning some of these lessons, to meet these of people. These folks guided us in the right direction, brought us into the right meetings, made the right introductions. And they didn’t do any of this for a fee.

My advice? Do your homework. Find out if the angel groups have had success, and if there’s a genuine interest in your kind of business or industry. Find out if they’re the right profile of investor you’re looking for. If not, then move on – don’t waste your time or money. Another piece of advice is to find a back door into an Angel group. Don’t follow the same protocol as every other company. Find a way inside the angel group through a connection – perhaps one of the angels in the group is active in your industry!

I think Jason Calacanis is doing a great thing by calling some of these groups out, because some charge a very unfair amount, and some of them have developed reputations for being egregious in these regards, and for wasting entrepreneurs time and doing little to nothing for the entrepreneurial scene. And Jason has a great platform to do this. These Angels and/or Angel groups definitely have a knack for ruining it for the others, and spoiling the bunch. That’s a damn shame.

Angels are fantastic resources beyond their financial capital. They’re intellectual capital is often priceless. They contribute a lot to the economy, providing financial capital for hiring people, for creating industries, and much more. Don’t let the bad ones spoil what can and should be a wonderful entrepreneurial experience for you and for the world.

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The Anatomy of an Entrepreneur

There’s been a bit of buzz in entrepreneurial communities about a recently released study released from The Kauffman Foundation titled, “The Anatomy of an Entrepreneur.” It’s available here. It’s worth the read. Entrepreneurs of all shapes and sizes will identify with some of the statistics, and find some quite surprising. It’s a decent report from which my own take-aways were the following:

74.8 percent of respondents indicated desire to build wealth as an important motivation in becoming an entrepreneur.

66.2 percent said the appeal of a startup culture was an important motivation.

Definition of founder: We allowed company executives to tell us if they were a founder. The guidelines we provided for defining a “founder” was “an early employee, who typically joined the company in its first year, before the company developed its products and perfected its business model.”

Age: The average and median age of company founders in our sample when they started their current company was forty.

Company founders tend to be well-educated Company founders in the industries we researched tend to be well-educated. More than 95.1 percent hold bachelor’s degrees or higher. A higher percentage of respondents had just bachelor’s degrees (48 percent) than advanced degrees (47 percent), however.

Among respondents, 36.9 percent described themselves as lower-middle class, and 21.8 percent described themselves as upperlower class.

Further, the results indicate that extreme poverty is a significant barrier to
entrepreneurship.

There are some great charts and graphs in the report too. I urge you to check it out but do not let this deter you from becoming an entrepreneur! These are statistics, nothing more.

Decisions, Decisions

iStock_000006048082SmallAh, decisions decisions. They never end in life, unless you just decide to spend your life as a lump on a log. But even then you still have to make decisions, starting with “I’m going to be a lump on a log.” If, however, you’ve chosen a life beyond lumping on a log, your life is full of decisions. Every day we’re faced with them:

Should I get out of bed?
Should I eat?
Should I wear the wrinkled shirt?
Should I get gas?

Those are routine daily decisions that we all have to make, and there’s nothing  exciting or risky about them – we all make them. We’re not paralyzed by them, unless we suffer from a disorder, as some do.

There are other decisions that are far more important, that we don’t face every day, decisions that affect our lives and the lives of those around us. Decisions like…

Should I marry her?
Should I have children?
Should I buy this house?
Should I get that operation?
Should my child get that operation?

People who are in business for themselves, whether they’re a self-employed contractor doing roof work around town, or an MIT scientist who discovers a new  vaccine, face a whole different set of decisions. These entrepreneurs make a huge decision once they decide to go into business. Some decisions entrepreneurs face…

Should I start my own business?
How do I get my first customer?
Can I afford to pay a staff?
Can I afford to pay myself?
Do I really have a business here?
Can I make money?
Should I raise money?
Should I incorporate?
Should I trade equity for money?
How much control do I give up?
Should I keep doing this?
Should I fire this person?
Should we expand the business?
Can I keep doing this?

The list goes on and on. These decisions have a way of putting an abnormal amount of stress on an entrepreneur because they’re piled on top of the routine/daily decisions, the big life changing decisions, and yet at the same time an entrepreneurs decisions affect herself, her spouse, her children, her family, her social life, her employees, her partners, her customers, her investors, shareholders, board members, etc. There are more people who have a stake in an entrepreneur’s decisions than one might first realize. It’s facing those decisions every day that partly define an entrepreneur. Some are good at these decisions, some aren’t. Some can make these decisions with little help, others need lots of help.

The hardest decisions I’ve faced as an entrepreneur have been the ones that affect individual people – like having to lay someone off, or fire them. There is just no way around it – it hurts the entrepreneur, the employee, and those around the employee.

Recently I faced another hard decision. This one pertained the direction of my company and pertaining those who were at the helm with me. You might say that I was at a point where I felt like my number of options were becoming more and more limited. And for an entrepreneur like me, who’s a fast decision maker after a quick risk/reward assessment, there’s nothing worse than being out of options.

Over the last few months I’ve had to face a reality that was hard to come to terms with – that the company that I’ve built with Bob over the last four years, that I’ve put so much of myself into, was slipping from my grip. I was not pleased with the direction it was going and my vision for the company was moving towards my periphery instead of where it had always been – straight in front of me. Something had to change, and some decisions needed to be made. Others agreed.

Ah, decisions decisions. They can halt you in your tracks. Some people can go their whole lives regretting one decision, and it becomes something of a curse. I knew I was at one of these splits in the road but I couldn’t be hasty. This decision required a lot of thought, and it required a lot of smaller decisions along the way, like playing a game of chess or poker.

A couple of weeks ago, the decision was made and almost immediate effect at many levels. And at the risk of being secretive, but in light of the fact that this decision was a sensitive one, I’m unable to explain what the decision actually was. It’d be inappropriate of me. Also, not knowing the ultimate outcome yet, it’d be reckless. But what it pertains is the very course that CitySquares takes in the near future and long term future. It’s the difference between surviving and thriving. It’s the difference between growth and prosperity or slowly suffocating. It’s about change. And change starts at the top.

Sometimes you don’t know if your decision was the right one for quite a while, and sometimes you know instantly. Sometimes you can go back and change your decision, other times they’re finite. This one was finite.

I learned something during this process, and it was something that I knew but hearing it from one of my investors, hearing him articulate it, and having him look straight into my eyes while saying it, really drove it home. What I learned was this: I am the founder of this company. While I have shareholders and a board of directors, it’s me and my vision that the investors bought into. It’s my passion, my knowledge of the space, my guts and gusto, my vision that got us this far. And if I believe in myself at least as much as my investors believe in me, then I must have an equal amount of conviction and gusto when presented with decisions that do not align with my vision and strategy of the business.

At the end of the day, when I have to rest my head on my pillow, I have to be able to say “I made the right decisions today.” Not making the right decisions, and not making them in timely manner, is the difference between sleeping well and not sleeping well – the difference between doing right by my own Self, doing right by those that trust me (from investors and shareholders to staff and customers) and one day living with regret.

I’m extremely pleased with my decision so far, and I’m proud that I turned this corner as an entrepreneur. Time will tell if they were the right decisions, but I refuse to be a lump on log and let others make them for me.

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When the Going Get Tough…

I’m posting this blog entry in two ways – video and the usual text blog entry. I thought I’d try this out and see how it goes. Please let me know your thoughts on all this, I’d love to hear from ya. Video is below, followed by the text.

[viddler id-2b584a47 h-370 w-437]

No doubt life is full of challenges, pain, suffering, obstacles – and all those things define who you really are. It’s not the good times that define you, shape your character, and test you, it’s the hard times, the darkest days.

This recession is doing exactly that to millions of people, if not billions. It’s global, and everyone is being affected – every day citizens, worker bees, small businesses, entrepreneurs, investors – no one is safe from this. And if you are not feeling the pain, than either you’re clueless and not paying attention, or you own a pawn shop.

CitySquares has felt the pain, pretty substantially. It started in the second half of September 2009, when the stock markets took a nosedive in the worst way. Our Q3 pipeline was a hefty one, and we were just on the verge of closing tens of thousands of dollars in new business. When the economy began collapsing, our pipeline just fell out from underneath us. It was pretty ugly. The first thing we noticed was the immediate and extreme reaction that everyone had to the economic downturn, but for us it was the small businesses that really highlighted the severity of things. They reacted as human beings, as real people – they reacted emotionally. So, over the next few weeks and into the holiday season we observed small businesses all across the country go totally radio silent. But what were they doing, aside from freaking out? They were trying to secure credit lines to pay their bills, trying to make payroll, keep their lights on. And all this right when the credit market was seizing up – no money for them. Then the holiday season showed up, and what do you have but small businesses with overstocked stock rooms, shelves loaded up with product that over the course of the weeks preceding the holiday season stayed that way. Now how are these businesses supposed to pay their vendors for those inventory orders? They weren’t able to move any product – and they’re stuck with all this inventory. Now it’s January and the invoices start showing up.

lifeboatThen it really got ugly for them. They started shutting their doors, turning their lights off, letting their employees go. All those businesses, those local merchants, who give so much of themselves to their businesses – closing their doors for the last time. It was painful for us to watch. And we too, felt the pain. Those local merchants, they’re our customers. So we got hurt pretty badly too.

Well, here it is now, July 2009, and the economy still sucks. But small businesses are a resilient bunch, somehow. Lots of them managed to get through that long rough patch, and the fog seems to be clearing up a bit. Although unemployment continues to climb, and consumer spending continues to fall, those small businesses that weren’t really going to make it to begin with seem to have fallen off the tree like dead leaves. Perhaps there was a bit of a shakeout, a necessary one? I’m not a data analyst, nor do I desire to be, but from our standpoint at CitySquares, we’re seeing a bit of a lull here – less businesses shutting their doors, and more businesses just hanging in there, maintaining, and even others that are wising up to online advertising (perhaps the subject for another blog entry).

Well, here’s my point of all this. CitySquares is not unlike small businesses. We are not loaded with cash. Yes, we raised money in 2007 and again in 2008, and sure that included some big name investors like Mark Cuban and Jonathan Kraft. But we’ve never been interested in raising a boat load of cash – for lots of good reasons. And because of that we are learning some really valuable lessons. You might even gather from this that because we’re not swimming in capital that we’re learning some lessons that others may not – what its like to really be lean, mean, and hungry. Just like in 2005 and 2006, when we were bootstrapping our business, we were forced to be really damn smart about how we executed on our strategy, and how we tested business model ideas. Here we are now, three years later, basically going through the same process.

CitySquares had to make some cost reductions, and that included lots of things, from renegotiating with vendors, to trimming the fat off our budget, and the worst part of all, reducing headcount. I can’t tell you the pain that I’ve felt having to do that last part – letting people go. It’s caused me more stress, sleepless nights, and soul searching than perhaps anything else in my professional life. It wasn’t the first time I’ve had to let people go and it won’t be the last. One thing is for sure – it never gets easier.

Today, like the small businesses all across the country, CitySquares is running very lean, and running a tight ship. We learned some very valuable lessons over the past couple of years, and I also learned some valuable lessons.

It’s actually pretty fascinating to see how people react and handle these kinds of stresses. This is when you really see who people really are, beneath the facade. Investors, board members, employees, vendors, partners, friends and enemies – you see their true nature during tough times. I can tell you straight up that there are some folks involved in CitySquares that have demonstrated their strength, their will to persevere, their guts, and those are the people that I want to surround myself with. Then there are others, who have demonstrated their lack of heart, passion, wisdom, their lack of leadership. Those are the people that I would prefer to be in the other lifeboat. Those people really scare me, those are the people that cause the plane to go down, the ones that will press the self-destruct button.

But perhaps most intriguing to me is how stressful times can inspire people to do great things, and with ease and control. In times like these you not only witness the strength in strong people, but the ability to dust off and not just get back in the race, but run to the front of the pack. Human beings are really damn good at surviving.

When people say, “hey ya know, it can’t get much worse that this right!” I always find myself responding quite quickly in saying, “Are you kidding me? Of course it can. It can get a lot worse!” And that’s not a way of suggesting that – oh no we need to head for the hills! Rather, it’s a way of saying – look, things can always get worse. You don’t know the bottom until after you’ve been there. So just prepare for the worst, get ready for it, but meanwhile work hard to make things better. You can always fall down another rung on the ladder. And ya know, in my personal experience, the ladder is pretty much bottomless. The higher you climb, the harder you fall. The idea is that hopefully you only fall a couple rungs, and not the whole damn way down.

Alright, well I’m speaking in tongue again. But I think I’ve made my point, but just in case I’ll sum it up this way…

Entrepreneurs: Things can always get worse. And rest assured that things will get worse. Maybe not today, maybe not tomorrow, but some day, things will get worse. Don’t ever think that you’re insulated somehow. That’ll be your downfall. Instead of looking down and kicking the dirt, or crawling around your cave looking for a better source of fire, get outside the cave and listen to the wind – watch the tides – look at what the animals are doing – look at the horizon – the signs are all around you. Go with the tide, go with the wind, go where the horizon is sunniest. Follow the momentum that is around you.

For CitySquares, that means we’re getting back to some basic concepts and focusing a whole lot less on complexity, and entirely on core value. We’re done listening to the weak ones, the ones who’ve never really been there or done that. We’re watching the horizon, listening to the wind, and steering our boat to go with the tides.

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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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