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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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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Getting it Done

This week ADP stated that 693,000 jobs had been lost in the month of December, and the U.S. Department of Labor stated this morning that unemployment has reached 7.2%, a 15-year high. Those are some gigantic numbers – terrifying actually. And the Fed says it’s only going to get worse this quarter, and potentially longer. Is it any surprise? Americans have been spending spending spending for years now, piling up debt, and living their lives on a credit score. Is it because of deregulation? Who knows. The fact of the matter now is that we’re now paying dearly for this recklessness in the form of job losses, bankruptcies, foreclosures, homelessness, and much more to come.

Everyone needs to smarten up, fast. Individuals, companies, no one is excluded fro this. If you weren’t aware of this a few months ago, in late Q3, you better damn well wake up! I was shocked the other day to learn that a friend of mine is actually quite clueless about all this. He’s a bit insulated from it where he lives and in his line of work, but no one is really insulated from this. My wife works at Harvard University, which recently saw its endowment cut substantially, losing 8% or $12B. For the first time in a long time, people are losing their jobs at Harvard, seeing their pay cut, seeing bonuses and scheduled raises off the schedule. Harvard, one of the most stable employers in Massachusetts, is having these kinds of problems. Again – no one is insulated.

This applies to startups too, of course. In fact, I’d say it hits us harder and faster than most other businesses. And that brings me to my point. CitySquares has been hit by all this. Sales are down as small businesses were reacting to the news in September and October, and as they refocused their energies and also smartened up. Sales are down, cash flow is down, some of our customers have gone under, some have been unable to pay their bills. Nevertheless, we’re seeing our way through this. We have an amazing tribe here at CitySquares – some extremely dedicated and passionate people. These qualities were demonstrated this week when I asked everyone to take a pay cut. The result? Some people took bigger pay cuts than they were asked to! And another thing – everyone stayed. Attitudes are great, everyone is as committed as ever. It’s just amazing to me.

I learned so much this week, as a CEO and as a Founder. I learned about employee psychology, I learned about my own abilities as a leader, as a CEO, as a founder. I learned even more about buy-in, about the difference between a decision and a choice.

So, CitySquares underwent pay cuts this week and I can honestly say that on this blog with pride, and with my head held high. Because I know that our team is prepared to do what it takes to weather this storm. Because they understand that paycuts for everyone means no one gets let go, everyone stays. And this tribe is aware of the same goal we’ve had for the past two years – the goal that’s now within 5-6 months from happening – the goal of cash flow positivity. The only way we can make that happen is if everybody here is on the same page, and that has not changed. Everyone here must work towards the same goal! Cash flow breakeven, in this market? In this economy? Outstanding! Show me a business that’s within 12 months of cash flow positivity, and I’ll show you a business that gets it. But show me a business that’s not making changes, not making the necessary cost reductions, not doing everything to ramp revenues and I’ll show you a business that’s in a lot of trouble.

Another thing, we wouldn’t even be here talking about this right, nor ever even arrived at this moment in time, if it weren’t for our investors, our angel investors from eCoast Angel Network and other outside investors like Jonathan Kraft, Mark Cuban, even my own father, among several others. We’re truly fortunate to have such fantastic individuals behind this company. Angel investors are special and its easy to forget how important they are to the economy, to the capital systems, and to the world of entrepreneurship. Angels make it happen.

So, there you have it folks. The truth as bare as it comes! And that’s what my blog entry from earlier this week was about – the difference between decisions and choices. Decisions I had to make, and choices that I had to give to the staff. There were difficult, very difficult, decisions that I had to make, along with our board of directors. These decisions lead to other decisions, and choices, for the tribe – and this week they all chose to help each other, to make the necessary personal investment, to protect each other.

Monday was one of the hardest days I’ve ever had at CitySquares. Today is one my proudest.