(The) Startup Depression

I wrote this to my email list on Saturday the 27th of 2008. Two days before the single largest drop in the history of the stock market. 

Now, I promised myself I was retired from blogging to focus on my email newsletter, but I’m getting pounded with so many requests for this essay that I’m giving up and posting it here. This does not mean my retirement from blogging is off, this means I’m posting this so I don’t have to respond to hundreds of emails asking for a copy. If you want future missives like this signup for Jason’s List: Jason’s List signup.

For background, the goal of this post was not to spread fear, but rather inspire folks at startup companies to get focused and to save as many as possible from hitting the wall. Myself? We’ll I funded Mahalo for the long-term and while the market down turn isn’t good for anyone, we’re largely immune from it because we are building on a five year plan that we’re only 18 months into.  

Doesn’t mean I’m not hyper focused, I am…. I’m just not panicking. Great entrepreneurs build value and market-share in down markets. They go to work seven days a week and the breakout when other folks check out. 

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(The) Startup Depression
Since stock market gyrations and the elections seem to be making
everyone rightfully nauseous and depressed, I thought I would take
this email to discuss the biggest ramifications of these challenging
times: depression.

It’s my believe that the economic downturn will be much worse than it
is today, and that 50-80% of the venture-backed startups currently
operating will shut down or go on life-support (i.e. 3-4 folks working
on them) within the next 18 months.

Make a list of every Web 2.0 startup to raise an A or B round and
cross 80% of them off the list, because they will not make it to their
next round of funding or profitability.

Now, I could be totally wrong. No one can guess or time the markets
perfectly. However, planning for the worst is a virtuous idea, so I
encourage you to read on.

Everyone I talk to is feeling confused, paralyzed and anxious–many
are in full-blown depression. People are scared, and they should be.
This could be the start of a very difficult time for our country and
the rest of the world.

In this email, we’ll focus on the entrepreneurial and startup
depression and economic downturns/depressions–and how you can deal
with them.

Some background to get us started
Few things in the world are as exhilarating as starting a new company.
Metaphors abound, and we’ve all heard them: starting a company is like
having a baby, falling in love, and running a marathon. Few folks,
however, want to continue the metaphor when things go bad at a
startup. If they did, we would be having discussions about running a
startup being like divorcing your spouse, collapsing from exhaustion
in the 20th mile of the marathon, or–God forbid–losing a child.

Metaphors swing both ways.

Anxiety and depression from a failed, or failing, startup can be
intense–even debilitating. When outside factors such as markets or
buildings collapsing are added to the mix, I’ve seen great
entrepreneurs just fold.

Now, I’ve never folded, and I don’t say that as some badge of courage.
No, sometimes it’s really, really stupid to keep fighting. Most
consider it especially stupid to fight when you know you’re going to
lose. I don’t.

The result of never folding is that I’ve had my ass kicked pretty bad.
Multiple times.

Depending on your DNA, getting your ass kicked is either complete
torture or deviantly rewarding. Truth be told, I like getting my ass
kicked because it makes me angry, motivated and focused. If I look
back on the couple of moments of success I’ve been lucky enough to
have in my life, they all seem to come after a good ass-kicking.

The darkest hour is–in fact–right before the dawn.

Brief Disclaimer
I’d be lying if I said I understood the complexities of depression or
depressions. I’m not a psychologist nor am I an economist. I’ve never
suffered from clinical depression and I didn’t live through the last
depression. However, I do have a BA in Psychology, have read many
books about the psychology of happiness, and I’ve felt the sting of
the last huge correction (2000-2002).

Consider these one (hu)man’s notes on “entrepreneurial depression and
anxiety.” They are worth the price you’ve paid for them, but I hope
they are helpful to you–especially if you’re suffering right now. If
you are suffering from depression or anxiety, go see a professional.

Really, it’s the best thing to do. Feel free to print this out and
bring it with you and ask your newfound therapist what they think of
my observations and advice. Then email me back what they said… I’m
curious where my thoughts rank.

Kurnit’s Three Reasons Why Companies Fail
Scott Kurnit of the Mining Company (aka About.com) told me there are
three reasons why a business will fail: it’s a bad idea, bad execution
or outside factors. If you examine your business with these three
filters right now, you can baseline where you’re at: one, two or three

His theory correlates well with the attribution theory in psychology.
The theory concerns itself with how an individual attributes the
things that happen to them (or others). For example, if you were
pulled over by a cop for speeding, you can attribute that to number of
factors, both internal and external.

Some folks might internalize the event and curse themselves for being
reckless: “I should have known better!” Others might blame an external
source, such as the cop or the bankrupt city they work for: “Gosh darn
Los Angeles cops! They’re just trying to balance the budget by
harassing us!”

Kurnit’s theory, as told to me, mentions two internal factors (bad
idea and execution) and one external (outside factors). When faced
with massive market uncertainty, like we are today, it’s a virtuous
idea to assess each of these factors.

Right now, every single one of us has HUGE outside factors we must
consider. The market collapse is going to make the next couple of
years impossible and frustrating for many entrepreneurs. Even the
great companies – like Google, Microsoft and Apple – are going to hit
hard times.

One of the most important philosophical minds of our time summed it up
best: “I never blame myself when I’m not hitting. I just blame the
bat, and if it keeps up, I change bats. After all, if I know it isn’t
my fault that I’m not hitting, how can I get mad at myself?” — Yogi

Viktor Frankl’s Search for Meaning
John Brockman, my dear friend and agent (if I ever get around to
writing a book), handed me one of the most important books of my life:
“Authentic Happiness” by Marty Seligman. That book led me to the most
important book of my life: “Man’s Search for Meaning” by Viktor

Frankl was a psychologist and Holocaust survivor.

He studied how people react to horrible circumstances that are beyond
their control. He studied why some people give up and others carry on.
While few of us can understand the level of suffering of people during
the Holocaust, Nanking or the Killing Fields, Frankl put his theories
forward so that we could carry them into our daily lives.

Logotherapy was what Frankl called his theories, and their major
tenants are that we choose how to find meaning in our circumstances
and that our experiences all have meaning.

My interpretation of Frankl is that you actually get to choose how you
feel about your circumstances.

The Worst Year of my life
It’s still hard for me to talk about it seven years later–and I’m not
going to talk about it in too much detail right now. In the early
months of 2001, I watched my first business, Silicon Alley Reporter,
crash from 70 employees to 12. The $20m offer I’d received to buy the
business was a distant memory, as was the $11.6m in revenue we had in

Money was evaporating from the bank account, dotcoms were going bust
and we–the dotcom kids–went from visionaries to charlatans
overnight. I went from hosting multi-million dollar conferences, doing
Charlie Rose guest spots and being featured in a 6,000 word article in
the “New Yorker” to not being able to meet payroll.

Many folks said I was lucky with Silicon Alley Reporter, while others
said I was fraud who had finally been found out. I was broke, no one
cared about my work, and my life really sucked.

… and that was just the start.

Then, the stock market crashed and the accounting scandals set in.
Enron, Adelpia, Worldcom, and Arthur Andersen made the fallout from
the dotcom bust look like nothing.

… and that was still just the start.

While lying in bed listening to the radio, I heard that a private
pilot in a small plane had accidentally crashed into the World Trade
Center. Then, I watched the second one hit. Then, I watched them come

To say things went from bad to worse would be a gross understatement.
As I started in disbelief with my fellow New Yorkers, I wondered where
my brother, a NYC Firefighter, was. Then it hit me: he was probably

Due to a simple twist of fate, he wasn’t dead–but many of his friends
were. It was at that time I really took a deep look inside and found
meaning in what happened that day and what happened to me when my
first business collapsed.

In my mind, I was being tested. Horrible things happen in life and I
was faced with several at the same time. From that point forward, my
goal was to not only get back to the level I was at when I was at the
top of my game, but to exceed it.

My goal was to be truly happy every day doing what I loved: running a
startup company. A year later, we started Weblogs, Inc., and 18 months
after that, we sold it. The darkest hour became the dawn, and it was

If you’re failing right now, and if you’re suffering, you need to take
Kurnit’s test. You need to access where you’re at and you need to
fight on. You can give up, sure, but the truth is that when you give
up, you have to live with that fact for the rest of your life. For me,
living with having given up in tough times is a much worse fate than
certain failure.

If you fail, then by definition you have tried. But if you give up,
you didn’t.

Step One: How are you executing
It’s fairly easy to tell how well you’re executing, so let’s tackle
that up front. First, take a look at your plan and see where you are
in executing against it. Are you ahead, behind or on schedule? Second,
you can have everyone in your organization rank your product and its
various features on a scale of one to ten. Third, you have an outsider
rank your product and features.

If you’re executing at an seven or eight or above, then you know
you’re doing well, but could be doing a little bit better. If you’re
executing under a seven, your problems could be execution-based. You
just may not be delivering the goods. If you were a restaurant, the
analogy would be that you’ve got the right ingredients and product,
but you’re just not preparing them well. This means you need to focus
on making the product better.

Another way to get a handle on how you’re executing is to take your
product and put it up against your two top competitors and do the
one-to-ten rating process. Rate yourself and your competitors on the
top 10 features of all three offerings. How many are you winning? If
you’re winning more than three, you’re ahead of the game. If you’re
three or behind, then you’re average or losing.

Execution is the easiest thing to fix, and you can do it one of two
ways: get the people in your organization to perform at a higher
level, or get higher-level folks into your organization.

It really is that simple: folks can either step up or step out.

Step Two: How good is your idea
Determining if you have the right idea is a little more complicated
since most great businesses do not finish where they start. Google
started as a search engine but bought Applied Semantics in order to
create their real business: text-based advertising.

Microsoft started by building programming software (Altair Basic), but
went on to make it’s business in operating systems, Microsoft Office
and servers.

If you’re idea is wrong, it really doesn’t matter. What matters is if
the original ideas allows you to evolve into your big idea.

In order to evolve, you must think like Darwin. Ask yourself: have you
adapted to your market? Have your customers asked you for something
different than you’re currently providing? Have you given it to them?
After you give them what they want, can you anticipate what they’ll
ask for next? Are those items following a theme?

At Silicon Alley Reporter, we started with a magazine and people loved
it. However, they wanted to get more frequent updates and asked us to
make it weekly. We reflected on this “ask” and came back with
something they didn’t even know they wanted: “the Silicon Alley Daily”
email newsletter. 40,000 folks subscribed to it in the first year and
it was a much more usable product than the magazine or the requested
weekly print newsletter that we passed on doing.

The market will tell you what it wants.  You just have to really
listen. Clearly, there was a market for the DEMO conference since it’s
being going on for years. However, they never listened to the “ask” of
the market: let the companies be selected based on merit, not their
ability to pay almost $20,000. Yes, I know it’s a self-serving
example, but those are the best ones. 🙂

When Mike Arrington and I founded the TechCrunch50 event, we didn’t
think it would grow to be 2-3x as large as DEMO after only one
year–but it did. The market had MASSIVE pent up demand for a
merit-based show and we tapped it. We evolved DEMO’s business model,
not our own.

Now, I’m left asking myself, “if I was trying to evolve TechCrunch50,
what would I do?”

Another example from personal experience with start up evolution has
been with Mahalo. When we started, we were just doing hand-curated
links. The pages had very little actual content on them. In our user
lab, folks told us they loved the links, but they kept asking for more

We studied the situation and realized that we could evolve and help
our customers more by writing more content on each page. To do this,
we studied what were the 10-15 things people wanted to know when they
did a search–then we put them on the page. Doing this drove our
traffic from 300k monthly users last year to 4.6m uniques in August (a
record month).

Bottom line: Your first idea is rarely your best.

The first step in a journey is never the best either! Most folks hit
their stride two hours into the marathon. Don’t be afraid to nuke your
first idea and run with your second–or third, forth or fifth.

Evolution is the revolution.

Step Three: Outside Factors
Outside factors are the toughest to deal with because, by definition,
they are outside of your control. Despite our deepest wishes, we can’t
reverse the housing bubble, put the Towers back up or reverse the
accounting scandals.

All we can do is deal with outside factors, and knowing how to deal
with them is critical.

When the market is in the middle of correcting, as I believe it is
currently doing, people tend to underestimate everything including:

a) how bad it will be
b) how quickly it will get worse
c) how long it will take to recover

Chances are the market will get worse and that will happen sooner
rather than later. Watching folks on CNBC last month talking about a
two or three quarters of down market was just sad. It takes just as
long to clean up a mess as it does to make it–typically longer.

The housing mess took two or three years to develop (2004-2006). It
will take three years to unravel (2008-2010) from what I can see.
We’re gonna be dealing with a bad market for at least two years.

10 Specific things you can do
Since the outside market is out of your control, the best you can do
is focus your energy inward. Here are some things you can do after
you’ve assessed where you company is at.

1. Execute better: This is fairly simple, as I describe above. Rank
yourself and your performance and improve it.

2. Grow the talent you have: When the market is down, it’s a great
time to get your team educated and to the next level. Invest in
training and education of your top people, because they are the ones
who will lead your company through this mess.

3. Firing the average people: Again, it’s totally politically
incorrect, but I highly recommend firing anyone who is good or
average. Startups are an Olympic sport and every slot on your team is
critical. You wouldn’t put a “good” swimmer in a relay, would you?
Don’t have one in your startup. Fire the good and replace them with
the great.

4. Cut spending every where you can: Recurring costs like
connectivity, phones, rent and insurance are things that you can
easily cut. Go to each of your providers and ask for 20% relief
immediately or you’re leaving. Most, not all, will give it to you.

5. Find a revenue stream and ride it: If you don’t have a revenue
stream right now, you’d better find one on Monday. Seriously, by the
end of the day. Once you find this revenue stream, ride it. Put at
least 25% of your effort into bringing in revenue.

6. Focus on your profitable clients: If you have revenue, start
focusing on which clients are most profitable. Take them to lunch and
figure out how you can over-service them and sell them another product
(or more of your current product). You’re gonna want to protect these
accounts because the folks reading Point Five are going to be calling

7. Make your top ten 10% better: Look at the top ten aspects of your
business and come up with a plan to make each 10% better in the next
30 days. Ask everyone in your company to make suggestions for the 10%
better program and execute on the ones that will provide the most bang
for the buck. Sometimes, there are things you can do today that will
make something 10% better for free–you just haven’t brainstormed

8. Hold an optional off-site breakfast meeting on a Sunday and see who
shows up: If folks don’t show up for you to grow/save the company on a
Sunday for a two hour breakfast, they probably aren’t going to step up
when the sh#$%t really hits the fan. You need to know who the real
killers on your team are and you need to get close with them now.
Again, it’s fine to have 9-5ers on your team–if you’re the Post
Office. You can’t have them at a startup company. Note: if you reading
this and saying I’m anti-family, save it. Folks don’t have to work at
startups and some of the hardest working folks I’ve met have families
and figure out how to balance things.

9. Build marketshare: One of the best things to do in the down market
is build marketshare. Look for competitors that are going out of
business and buy them or just “steal” their clients and talent (i.e.
pick them up).

10. Raise money: I know I said above most folks won’t be able to raise
money in the down market, but that’s not because the money isn’t out
there–clearly it is. The issue is that the big money out there
doesn’t want to fund small ideas that are in the death spiral. Build a
plan based on revenue and taking market share and folks will consider
funding you.

What ideas do you have for winning in a down market?

How do you stay inspired in bad times?

Send me your response and if you would like it quoted in a follow up
email, attributed or not.

all the best


160 thoughts on “(The) Startup Depression”

  1. Hi Jason, interesting analysis of the current situation and good tips.

    I liked the Darwin reference and fire the average people advice. I’ve always tried to apply evolution to how I run my business.

    I agree on focusing our energy inwards, solid well thought and executed ventures will
    survive the hard times to come.


  2. Firing average to good people sounds very harsh.
    I opt for more sympathy and respect.

    Further: Training for top dogs only? I disagree.
    10 managers and 1 code monkey won’t get you trough
    dark times. It’s 1 manager and 10 code monkeys.

  3. Hey, thanks Jason for posting this email on your blog.
    (I tried a few times to get on your email list, but, a invalid
    confirmation number error kept appearing.) This was a post
    that got back to the bare essentials, of what being a startup
    company means irregardless of the economic conditions.
    Maholo nui loa


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  5. This was a great read. I took this from the angle of someone who is in a changing business (newspapers), but the same things ring true. Execute better, ride rev. streams, cut expenses, growing talent in-house. Ironically, the old giants now must follow these same steps now because they were not nimble enough to follow the steps for growth during the good times.

  6. As I said in reply to the mailing list, this is definitely the best email of the e-mail nenewsletter (turned into a blog for this one post) and it is extremely insiguhtful…and on a side note…I hope that everyone else is preparing for nuclear winter along with me.

  7. On the subject of not spreading fear, this was the biggest point drop in history, but far from the biggest drop percentage wise. The Dow lost 7% today versus the 22.6% it lost on Black Monday.

  8. As I have said before and I will say again, this man is brilliant!!

    I really don’t understand why people give him such grief??

    The man is passionate and he is sharing his “knowledge” wealth. I just wish I had the 1/10th of 1% of his passion. He built a company where their motto is “We’re here to help”. I truly think that is what he is doing… he is helping.

    I think most people “Can’t Handle the Truth” as Jack said 🙂

    Thanks Jason!

  9. Jason,
    Great article. I agree with all of your points, except:

    5) “Put at least 25% of your effort into bringing in revenue.”

    I’d say put at least 75% of your effort into bringing in revenue.
    That’s what Great businesses do.

    8) I agree. Make it Saturday so you don’t waste a day and
    you can still attend church.

  10. Excellent and my first time here, so it’s a pleasure. There’s always going to be problems – big or small, outside of your world. You’ve just got to worry about your own life sometimes.

  11. The “balance” that the hardworking people have found is that they have a spouse who is willing to basically be a single parent. But you are right about one thing, people don’t have to choose to work at a startup, especially not ones that pull daft stunts like loyalty tests. The problem is that time and time again people will fall for get rich quick schemes and technology workers are not exempt from that.

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  13. “They go to work seven days a week and the breakout when other folks check out. ”

    – I think you meant they instead of the breakout.

    You have a very good article, but this is by no means something
    that I was preparing for. If anything, this doesn’t really
    help me or my position. Not saying that you haven’t motivated
    me, but it is the fact that you assume a lot of people are
    beginning with a lot of resources for a start-up that has me

    I just don’t have enough money to be in the position of firing
    anyone, never been in a position that I fell to 27 employees,
    never been in a position that when our country is falling
    apart, that I would make a blog posts ordering up the
    movement of becoming a have and disposing of the have-nots.

    It isn’t that I don’t understand your speech. It is that it
    has three negative connotations that made me a little upset.

    1) A lot of what you said had to do with self. If anything,
    the reason this country is in this position is that we
    are constantly playing the “Olympic” game and trying to move
    ahead. I would feel the best thing to relieve stress is to
    try and comfort everyone around, and maybe even contribute
    to someone else’s project, instead of racing head-first into
    the financial recession. But that is just me, and I know
    nothing of business. I do know that I cannot mollify my
    sadness by trying to make my business work during a very hard
    time for all Americans, and not just the poor, or the rich. I
    feel that a more emotional approach to the matter would’ve
    been better, and more respectful to our country’s current
    situation. I know you speak of business, and that these are
    hard times for entrepreneurs, but I was hoping for some
    emotional bark.

    2)That you pose a question correlating one’s suffering and loss
    of their business upon a simplistic 10 step plan. And although
    it sounds motivating, you simultaneously point out that some
    are barred from living your dream if we don’t pass this
    “test”. I understand that some make and some do not, but is
    it plausible, or even fair, that someone will fall away from
    their dream because of a motivational essay that gave them
    a reason to give up? I find it a little negative, and
    somewhat betraying to the article’s title. I was at least
    hoping for an article that didn’t sound like so many other
    blog lists that saturate the web.

    3) I know that you are very successful, and I know that you
    are gifted, but you have reached a fallacy in your perception
    of knowledge. You believe when you write that if you compare
    your examples of starting-up ( firing people, Sunday meetings)
    that people will understand. But there are many, maybe almost
    80% of us who don’t have a workforce, or who started with
    less than $30, or who doesn’t have that cushion to prevent
    the wrath of outside economic forces. Also, you go so far
    into the business aspect that you totally overlook the trust
    and friendship aspect that may help businesses survive in the
    long run.

    Dropping not as lucrative clients? Firing workers? These all
    have their positive merit, but not narrowly based on the
    bottom line. If I was to leave half my clients, and the
    economy came back strong, I would lose them for good. Not
    only as business partners, but in some cases as good friends.
    If I am going through tough times, I would heavily prefer a
    good friend and/or trustworthy acquaintance over solid revenue

    I am not here to bash you. My critique is harsh because I only
    expected something more from what you wrote. I think that your
    last two questions can be answered by:

    1. Winning in a down market. Make connections with all types
    of people. Write down these connections and constantly keep
    in touch. Friendship and bonding will catalyze your business,
    or remove your depression, which I feel is a no-lose situation.

    2. Watch sports. And remember that in professional sports,
    there are only a handful out of the millions that make it. Try
    to become that handful, but don’t carry with it any arrogance
    or exclusivity. Use your power and place for good, and make
    sure your ends are good, regardless whether your business
    endeavors survive. Once you feel you can help others and make
    the world a better place, you won’t feel depression because
    of finances. Emotions should be what you control, and not
    your money controlling you.

    You can erase this, I just wanted to send this to you. you
    can email me at info@juuble.com to reply.

  14. Excellent post Jason. Certainly a reality check is in order as we look to 2009. The only other thing I’d like to understand is why you make people read your posts in hard to adjust gray.

  15. Great post. The coming times will be a true test to start ups and will further separate the ones that can adopt to bad economic situations and the ones that cant. The money is still out there and everyone will either have to work harder or smarter for it.

  16. Good analysis and advices. However,
    I think,
    Great people = good people + passion + motivation.

    Hence, I would be very careful to let any
    good one go.

    Best Wishes for all..
    Subhankar Ray

  17. You bring up some excellent points here Jason, but they shouldn’t be limited to times of economic downturn. As entrepreneuers, we should always be relentlessly focused on staying lean, executing and finding that winning value proposition. We are raising money for our latest start up now (Alice.com) and I’m pleased to say that the economic downturn hasn’t killed our round.

  18. So why don’t you run on the Independent ticket? Sounds like you have more ideas and a lot of them better than what I’ve been hearing lately. We really need some new blood in Washington I think because the old stuff is just the same old stuff. If the country was run more like a business than the playground of some of those old guys that have been up there too long, then we might have a better chance, maybe???

  19. Here’s a healthy lesson from the field of stock market investment: a company with debt cannot go bankrupt. If you don’t owe anyone anything, the WORST thing that can happen is that you are forced to put the company on ice and take a job in the mean time. Remember that.

  20. You Blob might really be interesting if I could read it.
    The light gray print makes it impossible to concentrate.
    You might want to change that!!

  21. Spoken like a true Spartan! Your Greek roots run deep 🙂
    Never giving up is in the genetic make up of the selected few who will always succeed!

    The darkest hour is–in fact–right before the dawn. From personal experience, I can say you’ve got that one spot on! The most difficult time in my life was realizing that I was studying the wrong thing and dropping out Civil Engineering, and it’s at that moment where I decided to give the online world another a chance, and what a great new dawn on my life it was!

    As I move forward in the next few years, the advice you’ve given here will definitely stay in the back of my mind! When I start getting onto serious stuff. Thanks for the inspiring post at the start of these rough times.

    “The darkest hour is–in fact–right before the dawn” == Ultimate Truth!

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  23. Great article, Jason. There are some things that I disagree
    with, but on the whole, I think that you bring up some really
    good points. The only thing that I find myself wondering about,
    though, is just who you are. At times, I think that you’re
    sincere in your beliefs, and then there are times when I think
    that you’re all about “the act.” I guess in the end that it
    doesn’t matter, though — you’ve given some good advice.

  24. Pingback: Machinima Blog
  25. Great read, Jason. The one word that will continue to separate the winners from the non-winners will be “perserverance”. Not particularly profound, but a law that always sustains. Great ideas that bring great value coupled with great execution and management will continue to get funded.

  26. Enjoyed the read, Jason, but I can tell you as a cancer survivor, “depression” kills. The one word that will continue to separate the winners from the non-winners will be “perserverance”. Not particularly profound, but a law that always sustains. Great ideas that bring great value coupled with great execution and management will continue to get funded.

  27. I don’t know if the stock market is truly the sign if the economy is doing good or bad. Since most are corrupt and are just pushing money around. I think it’s what got us into this problem. I think the web is better place to determine how americans are feeling lately.

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