Two years ago, I partnered with an awesome CTO, Alex Lines, to start a company called Path 101.  We didn’t get enough traction on the product and business to continue it fulltime, so we’re now working on it as a nights and weekends project as we take on other jobs.  This is the 2nd of a series about what I learned starting up a company. First one is here.

A few months ago, I wrote about the three types of deals VCs do.  One thing I realized was that aside from just betting blindly on an experienced entrepreneur or funding a later stage project, was that when VCs put money into something that's innovative, they tend to do it in an innovative sector.  So, it's not just about the idea, but they want that idea to live in an ecosystem that is in flux or generating new and interesting approaches.  For example, BazaarVoice (a First Round portfolio company) helps power social commerce with a variety of applications that help amplify customer voices to both sellers and to other customers.

No matter what they started with, social shopping was definitely an interesting area when the company started in 2005 and got funded in 2006.  It was clear that reviews and social media were helping sell product, so a bet on a suite of tools that helped companies create conversations around commerce would seem to have the wind at its back.

That's exactly what we didn't have at Path 101 in the jobs space.  In fact, what was fascinating to me, and unexpected, was how negative VCs were on the jobs area--especially for something so monetizable.  There there had been very little innovation in the way that companies hire and the way people find their jobs online in the last 15 years--except for LinkedIn--and investors largely saw that industry as a hopeless dinosaur.  Sure, there were business model innovations, like TheLadders and Indeed, but these were mostly about subtle changes in the way these companies made money.  It was still job ads and resumes at the end of the day.  The average VC didn't quite believe there was a disruptive job play to be had, so the idea of thinking of us as that play was a stretch. 

I can't exactly blame investors either.  Often times, investors bet on the "pivot"--the ability for a startup to stop what they're doing and have a strategic shift in the product or business plan.  It probably happens a majority of the time, and so an investor needs reasonable assurance that the team is going to pivot into something good.  If you're in a dynamic industry that is primed for innovation, not only is it easier to see where the next big thing is going to come from, but you get more experimentation from customers.  They're more willing to try new things because they know business is changing, but they're not sure exactly now. 

On top of that, it's easier to get press if you're in an industry with some buzz around it.  If you were to do a new geolocation startup, like Hot Potato, everyone will want to talk to you because there's obviously something happening in this space.  No one was really that excited about talking about new models in the job space.  Heck, the only blog actually covering new models in the space, Cheezhead, stopped publishing over a month ago.  

The other thing was that ideas don't happen in silos.  It helps to surround yourself with a vibrant community of entrepreneurs--and in the job space, there were only a handful of people I felt like I could talk with about new models.  Everyone else was basically minting cash on businesses that I couldn't understand how they'd even be able to exist in five years.  That meant that our inflow of new ideas and great feedback was pretty limited.

It's hard, because there wasn't another industry that I really wanted to change so badly.  Careers was my thing.  I'm extremely passionate about helping people figure out what to do with their careers, but ultimately, creating a startup in this space was an uphill battle from the beginning.  I'm not saying this was a fixable problem--just more like a warning to new entrepreneurs.  Take a look at your space.  Wipe your finger on the tables.  If it's too dusty, you may want to wait a little bit before trying to move the furniture around.

Two years ago, I partnered with an awesome CTO, Alex Lines, to start a company called Path 101.  We didn’t get enough traction on the product and business to continue it fulltime, so we’re now working on it as a nights and weekends thing as we take other jobs.  This is the 1st of a series about what I learned starting up a company.

Raise money--That's the first thing many entrepreneurs think of when starting a business.  They plot world domination schemes that hinge on their ability to get an angel round together, without answering a lot of important product questions first.  That's fine if you're Rich Barton from Zillow and Benchmark gives you 7 million bucks to go do to real estate what you did to travel at Expedia.  If you're running leaner and you're raising "Get something up" or "just feed ourselves for a little while" money, you need a lot more questions answered. 

That was our first mistake at Path 101 and I'll take the blame for that one personally.   Or, you could think of that mistake in a different light and say that I should have realized that we were going to have to be a lot more experimental and iterative.  That would mean needing closer to a million dollars than the 350k we raised—and we definitely could have gotten more.  We just had this innate desire to be lean and only take what we thougth we needed.  Nowadays, I tell people to take twice what they think they need, especially if they’re doing this for the first time.  Maybe it should have been a little of both, but regardless, wireframes, specs, etc  should all be done before you take money.  Granted, these will all change, but you can go a long way to honing in on the product roadmap in great detail on your own time. 

For example, Aardvark worked on their product design and user interactions for 8 months before writing any code and before taking a big slug of cash.  The social answers platform started out with a dude on the other side of a chat account manually interacting with users in a structured way in order to product test.  They knew a ton about how their product was going to work and what it needed at the onset of development--and that's something you can do nights and weekends or bootstrapping.  It doesn't need a designer either.  Just tell me your best thinking on exactly what the product will do, in detail--talking basic wireframes here--at each milestone and how much money it will take to get there.

Milestones are important because not only does it help to estimate cost, but it helps figure out revenue and funding potential.  You can (and should) take a wireframe to a customer and say "If we build this, will you buy it...and if no, why not?" 

VCs may be a little different.  They probably won't take a vaporware presentation very seriously unless you know them or someone vouches for your ability to build something.  Get a warm intro.  Scared that they'll take your idea?  Someone can steal your idea a month after launch anyway, so what's the difference?

At Path 101, everyone we talked to thought that the idea of pulling resumes off the web to figure out career paths was really interesting.  We talked about what data you might want to pull out of the Resume Genome Project but not a lot about what the data actually needed to look like to be useful to a user.  There was no way we were going to get that right on the first try, but there's no reason we couldn't have had three or four iterations of that done--not just to show investors but to show developers, too.  This would have helped us get a sense of technical challenges that maybe we weren't considering or just to generate more interest in our vision.

There wasn't a good model out there for what we were trying to do, so answering a lot of the questions about how users were going to interact on the site would have gone a long way.  Instead, we did a lot of this research (and made more mistakes) when we should have been developing to more specific, vetted milestones.

That was lesson number one--more to come.

Last December,  Owen Davis from NYC Seed decided to make my company, Path 101, the fund's first investment.  Given my recent announcement that I'm taking a full time job at First Round Capital and that the Path 101 team is going part time, I have to imagine we've been written off as an investment--from a financial point of view.  God help the next company that has to pitch to the NYC Seed board now.  The board is a room full of about a dozen folks, which is about ten people too many for making early bets on seed stage companies.    Undoubtedly their mindset after the news will shift even further to risk mitigation versus additional risk taking, especially after what our experience might be saying about the funding environment. 

That would be a mistake, however.  Experienced angel investors know that a 50% loss rate is about average--they expect half their portfolio not to return any capital.  That's how the business works.  So, if another NYC Seed company fails soon, that would pretty much be well within normal expectations.  I feel like a group of government folks isn't really going to buy that, but they have to.  The Bloomberg administration trumpeted the fund as a way to spur on innovative technology ideas and fill the funding gap for cutting edge startups.  If it had to only pick from companies that could break even on $200k, you'd see little in the way of large scale market disruption coming from these companies.  In other words, you don't pick the next Google by mandating that the company generate enough funds to cover itself within the next nine months.  You might as well invest in a couple of accounting firms or food stores--very little chance of losing your money on those. 

In fact, one could easily make the argument that a heck of a lot of good could be done while still losing the whole entire fund--laying a big fat goose egg.  People learn a lot from failure, and having a culture that excepts high failure rates is critical to a truly innovative scene.  Also, when companies don't work out, founders and employees often move on to other startups, taking their experience and making themselves more prepared for the next challenge.

Take the investment in Path 101, for example.  By enabling us to continue an extra year, we were able to build better relationships with the innovation community and investors.  I was able to pitch and continue communication with Josh Kopelman from First Round Capital.  In turn, First Round is now opening an office here in NYC.  There's no doubt in my mind that First Round will invest *at least* $2 million more dollars in NYC than they would have anyway now that they have an office here--so this development is actually a net positive for the city.  We all said there wasn't enough early stage capital located in NYC, and now, we have a new top tier VC fund setting up shop right in the Union Square/Shakeshackville area.  Add in the fact that my partner Alex Lines is joining Betaworks.  Who knows, he could hack something up that winds up becoming huge.  In a way, NYC Seed enabled him to find someone to fund his hacking.

Plus, we've now unleashed machine learning PhD/scientist Hilary Mason's data mining expertise on the NYC startup market.  After moving here to NYC, she's now looking for neat data projects to work on, particularly locally.  She has a highly soughtafter expertise and our company attracted her back to NYC in the first place. 

By allowing the Path 101 team more time to be out there in the market, NYC Seed unintentionally deposited some innovative human capital back into the innovation ecology here.  The results are likely to be way better than anything just our one company had a realistic shot at, but I wonder how this fund will be measured...  Net returns or overall economic impact.  I hope the board will take a broader view of the impact of the fund and even extend it's life past the mandate for $2 million.  It certainly can't help the portfolio's risk profile if Owen is making bets thinking he's only got six bullets left in his gun and that's what he's going to be judged by.

Whether you realize it or not, as a jobseeker you are participating in a marketplace.   Even when you're not a jobseeker, you're part of the equation.  Employers are the demand and workers (or resumes) are the supply.  In this economy, demand is low and supply is high.  Employers have more workers in their ranks than they need, so layoffs and cuts continue to pile up.  They also have stacks and stacks of resumes from people wanting work--even willing to work for free.  Right now, most HR departments could probably recruit from their own inboxes without ever spending a dime on job postings or resume databases.

Actually, I'm not kidding.  That's probably closer to reality than many big job boards are willing to admit.  Revenues at Monster, Careerbuilder, and Hotjobs have taken a nosedive recently.  Because these companies have totally inflexible business models, jobseekers who post to those boards are feeling the hit, too, but they might not realize it. 

Many people aren't getting any bites on their resume  and assume that's because companies aren't hiring.  That's partly the case, but it's also because those job boards are charging fees to look at your resume and contact you.  In today's market, this is a bad deal for companies who already have plenty of resumes in their inbox.  The market had decided that the incremental value of *another* resume in their inbox is near zero, if not zero already--so why pay for something you already have?  More and more people are uploading their resumes to Monster and the big job boards when fewer and fewer companies are willing to pay Monster to see them.  That's right--receiving your resume is essentially worthless to an employer right now... and the big job boards are making it even harder for you by trying to charge companies to see them.

It's the same with job postings.  Why pay to post a job when you can just email your network and ask "Does anyone know anyone good who needs a job?"  You know what the answer to that is these days.

In any transaction, one or both parties needs to pick up the tab for the cost of the exchange.  If companies are less and less willing to pick up that cost in a tough economy when it comes to jobs, it's really going to have to fall on the consumer.  Lots of people recognize that cost will mean additional time and effort on their part, but how many people are actually investing real money into their job search?

On the higher end of the market, users of TheLadders are paying to see only the best jobs and many are paying getting their resumes edited as well.  Is that helping them get in front of employers or getting them a better shot at a job?  Jobs on TheLadders aren't necessarily exclusive, but one would imagine that it does indicate some level of seriousness if you're paying in to see a job. 

What else is out there?   There are lots of conferences and career coaches--essentially content, but the thing with content is that you don't really know if it's worth it until you consume it.  Career content can't be advertising backed in this economy, because as we said before, companies aren't paying to reach you and see more of you now. 

If I were job seeking now, I'd be paying for a Google and Facebook AdWords campaign--putting money behind my efforts at getting in front of the right employers.  Apparently, I'm not alone in that.  In a recent survey that we took at Path101.com, 55% of job seekers would pay to promote themselves online.  Even more interesting was that 23% of people would pay to promote themselves even if they weren't job seeking.  

What do we mean by that?  How about making sure you're ranked first in all the places people might go to look for you?  Take WeFollow.com for example--the Twitter user directory.  If you were an athlete trying to generate a bigger fan following, paying up to be the "Featured User" on a list of top Twitter users tagged "sports" would be worth it.  I think this is where MyBlogLog could have gone, too.  How many people would have paid a little extra to be a profile that lingers longer on Fred Wilson's blog, for example, perhaps with a direct link to their blog.  What about Disqus?  Featured comments?  You could argue that would lower the quality of these lists, but on the other hand, wouldn't you make sure you had a quality/relevent listing if you were paying to make sure it ranked high?

I think there's an untapped market here--to bring the power of sponsored search to the job seeker and individuals to help them promote themselves in the right places--similar to what Indeed.com does on the job side.  I wrote about this about a year ago in relation to people putting cash behind their best blog posts to gain exposure.  Enabling people to get more active about their own self promotion is something we're working on now at Path 101.  Uploading your resume to a big job board is like sending it into a black hole--and candidates can't do anything to actively get noticed as part of that process, even though they want to.  

I had a fascinating conversation with an early/seed stage investor yesterday who basically described the market as follows...

He said that, over the course of all of their deals (over 50), they've done a very good job figuring out what a team will need to do to raise venture capital.  Their investments are basically meant to supply a team with about 9 months of capital to go out and build something and "jump 9 feet", because that's the milestone they see for VC--whatever 9 feet is for that particular comapny.

That had been going pretty well up until deals that were done in the first half of last year--right around the time that Path101.com got it's first angel financing.  Now their companies are coming back into the market, as planned, for financing.  They're reporting that instead of the 9 feet they were training for, they're now being asked to jump 15 feet by the VCs.  Somehow, companies are supposed to get straight from product to revenue--without iteration or even traction in between.

If you're an investor and you can get a Series B company--one with revenue traction--for Series A prices, why would you ever do a Series A?  It's not unfair--it's just good business.

Welcome to raising capital in 2009.  Go straight to Series B or do not pass go.

This investor was basically doubling the size of the rounds he was doing--splitting them with a partner fund--in order to give companies longer runways to actually make it to sustainability.  He described your angel/seed funding like a rocket ship.  You need to decide how big of a fuel tank you need to take you into orbit, because, these days, if you run out before you get there, there's no refueling mid-flight. 

We'll be talking to our board tomorrow and the theme of the conversation is more or less "If financing happens, great, but we're not going to wait around for it."  We're still in conversations with investors, but our product plan has prioritized immediately monetizable features.  We're shooting for 45 days, give or take a few bug fixes here and there, to launch both recruiter and candidate services we can sell.  We've cut our burn pretty low and we're working on some in person job search seminars to help extend the runway.  We're not going to disappear tomorrow, that's for sure--but we want to still be here six months from now and beyond.  That takes a solid plan and some rolled up sleeves.

What am I telling startups now?  Forget raising 250-500k.  If you can raise a million, do it--because the chances of you creating a break-even business on 250k-500k is pretty low.  If you can't raise a million, then only focus on building something that a customer is willing to pay for TODAY.  (That should focus your product roadmap just a bit.)  Anything in between will be a bridge to nowhere. 

UPDATE: Fred wrote this post yesterday about becoming the default behavior for your market--ahead of figuring out how to monetize it.  I think the problem with that thinking is that it basically only gives you one shot.  You're playing startup Russion Roulette when your goal is to become the default activity and you have no Plan B.  At least of you monetize in some way, if it takes you two or three tries to become the default, you have the runway to iterate.  We're all aiming to become the default activity for our consumer base and the service we provide--but it's not always clear how to do that.  Lots of people wanted to be the Google of events--it never happened, but not for lack of trying.  In new markets, it's not always clear what model wins out, and often times the last one standing wins.  It's hard to be the last one standing if you're not making money.  The key is to make money in a way that doesn't hinder your growth. 

In hindsight, I wonder if perhaps we at Union Square Ventures did the world a disservice back in 2005 when we started blogging as a fund--opening the kimono on the world of venture capital and making it seem like it was within arms reach.  Maybe the world was better off when businessplans@venturefund.com was the black hole where your ideas went.

We have a new black hole where all the ideas go today--but this time we call it the economy.

Before all the transparancy, those who really wanted to pursue their ideas, out of necessity, went and got paying customers for their business day one.  If you built a great business, the VCs would find you, but short of that, you didn't have all of these conferences, bootcamps, etc. making you feel like you're just an investor away from the next big thing.

People would tell me, "Oh, you're lucky that you used to work for a venture fund, because you understand what they want."  In hindsight, I don't know about that.  I might have been better off not knowing that venture capital existed, aiming for profits from the beginning--and then just being nicely surprised if some dude shows up at my door with a few million in cash asking to buy a minority stake in my business.

Venture capital is like winning the lottery.  Somebody wins, but statistically, it's not you.  Don't wait for an investor to go build the business.  We're not--not anymore, anyway.

Penelope Trunk is supposed to be some kind of expert on generations and the workplace, but I don't think she could get the following more wrong:

"Do you know who is using social media? Gen X. The average Twitter user is in their 30s. The median age of LinkedIn is 40. The majority of people who are joining Facebook right now are over 35. This is because Gen X wants to meet new people online and reconnect with all the friends they lost along the way. Gen X is using social media to network. "

Actually, the average age of internet users--and the US population in general, is around the mid 30's.  To say that Gen X is doing more networking, and disproportionately so, is just misleading--it's just flat out wrong.  Social networkers pretty much reflect the makeup of the US internet user audience.  Gen X isn't any more networking savvy than any other group.

"Gen Y doesn’t need to. They never lost their connections because they’ve been online since they were ten. They do not need to meet more people online to expand their network because they are native networkers – they have had the tools and the predisposition to use them since before Gen X even knew what Facebook was."

This is just utterly ridiculous.  Gen Y doesn't need to meet more people online to expand their network because they've been online since they were 10?  I don't know about you, but nobody I know basically made all the career connections they ever needed to make between the ages of 10 and 21.  If anything, Gen Y needs the most networking help because they grew up with "Stranger Danger."  They got taught that people they don't know are likely to try to hurt them, so they tend to connect online to people they already know.  Facebook reflects that and it's the reason why Gen Y is so much less likely to use LinkedIn.  On Facebook you connect to your friends, and on LinkedIn you build your professional network, often reaching out to new people.  Getting Gen Y to use LinkedIn is like pulling teeth.  Perhaps Penelope should teach a class of college students over a full semester like I do to get a better sense of how Gen Y really networks online.

"So while Gen X is busy using Twitter to let people know what they are up to and promote the hell out of whatever they are doing, Gen Y is using Twitter for tweetups – meetups set up via Twitter. Which is a way of making genuine friends offline."

So Gen Y does tweetups more than Gen X?  Most tweetups are tied around some kind of professional group--not likely to be attended by a majority of Gen Yers.  Disagree?  Flip through who is actually Tweeting Up right this minute.  On top of that, most people on Twitter aren't really promoting anything.  Sure, the "gurus" and social media mavens are, but by number, most people on Twitter just follow a handful of people they know and just Tweet about their life.

Sherry Mason from Bowdoin College wrote "College kids I work with need coaching on tone & style" and she's absolutely right.  Just because a Gen Yer may have 1000 Facebook friends doesn't make them an expert at networking any more than following 10,000+ people on Twitter does so they follow you back.  (I always thought networking involved listening... I'm sorry, but you can't listen to 10,000+ people at once, even if you're using Tweetdeck.)

Networking involves the following basics, none of which I've found Gen Y to be particularly good at:

• Self awareness: How are people perceiving you?  Gen Yers, because of their lack of experience, don't have a great sense of professionalism and professional appearence.
• Storytelling: How can you package up your experiences, interests, goals into something memorable that others take with them and remember.
• Listening: I don't think any generation is good at this, Gen Y included.
• Outreach: Reaching out to the right people to build relationships--this is where Gen Y majorly falls down because those kids aren't any good at going outside the comfort zone of their own network--unless their mom schedules a playdate for them. 

Gen Y sucks at networking.  Don't let their Facebook friend list fool you.

Someone sent a note to the nextNY list about how he was unemployed and looking to work for a startup--how it was really hard to find something.  He sent a link to a piece he wrote on a site about being unemployed.

This was my response:

"So the one link you send us is on a site about being unemployed?

Why on earth would you market yourself as an unemployed guy?  In your first instance of participation in this group, you cast yourself as laid off and desperate.  Who wants to hire an unemployed person?

No one.

If I showed up to a date and the girl introduces herself by saying, "I've just been going on nothing but first dates and they never work out...   I'm so desperate to find someone" I'd be looking for the door in a heartbeat.

We all want to hire someone who kicks ass at something.  If you do not kick ass at anything, you should at least be in the process of learning how to kick ass at something.  Startups, or frankly any company for that matter, cannot afford to hire a non-asskicking generalist.

Think of it this way...  If you know the media, perhaps you could have spent the last five months doing free PR and marketing for a handful of startups.  You weren't working anyway.  The goal would be to be so good at it that one of those companies can't help but hire you--or some other company would hire you because they noticed how good you were at it--or worst case you'd suck at it but you'd really learn something.

Forget pursuing.  Spend 110% of your time honing some kind of value proposition that you'd be a no-brainer hire for.

Forget the "I'm unemployed" shtick and work on the being awesome without advertising the fact that you are awesome to everyone.  If you do not know what awesomeness is, try and figure out who the top 30 most awesome people in the NY tech scene are and interview them.  Publish the interviews on your blog.  Make a list and publish it.  Here are my suggestions:  David Karp, Anthony Volodkin, Chris Hughes...

And God help you if I see your blog and it's yourname.blogspot.com.  To be awesome, you must splurge for the $13 domain name."

Ask the average venture investor how excited they are about the recruiting space--you'd get more enthusiasm in the waiting room of a dentist's office.  I don't blame them.  There are a million "Me, too!" companies and the space is nearly devoid of innovation. 

How many ways can you smuch a resume against a job post?  Turns out... tons... or really just one, dressed up as tons.  On top of that, there is a severe lack of focus on behalf of the job seeker--and if you're not helping people with their career, just what are you doing? 

Early in 2008, my partner Alex Lines and I finished raising a small angel round and got to work on building a company called Path101.com.  We're a small team working on an innovate approach to career guidance--and we're getting closer and closer to meeting our potential each day, but we're still not there yet. 

The career space still haven't solved really basic problems of helping people find jobs and careers--and each year the potential of the technology pushes forward, the industry falls further and further behind.  The future is coming much faster than the current players are preparing for it. 

It's clear that five to ten years from now--everyone is findable on the web.  Every job is nearly already findable through aggregators like Indeed.com and Simply Hired.  Just like the market specialists on Wall Street who disappeared when electronic trading came into maturity, many of the players adding friction in the middle of this marketplace will go away.  We're seeing this happen on college campuses, where employers are connecting directly with students and visits to career centers are way down.  Sure, there may be some people still finding niches to connect people--but surely a lot less in a hyperconnected, seemless world. 

What we're heading to, like it or not, is a form of electronic trading markets for people--where exactly who you are and what you can do can get instantly mapped to exactly the company and role that makes the most sense for you and your interests.  Unfortunately for most of the existing players--a resume and a job post not the kinds of data infrastructure that will get us there.  A resume doesn't tell you nearly enough about who I am and what I can do, and job post doesn't tell me anything about the path that post leads to or what my experience is likely to be in that position.  That's why all these "eHarmony for jobs" companies are failing to get the job done.  Trying to get everyone in the right place seemlessly with such poor data building blocks would be like trying to run a stock market ticker with refrigerator magnets.

There are all sorts of incentive issues and missteps in the job space.  Here are just a few, as I see them, from both sides.

First, here are five ways job sites fail the job seeker:

1) The job boards like Monster, Careerbuilder, and Hotjobs fail to give job seekers the data they need to make adjustments and navigate opportunities.  How many people already applied to this job?  How does my resume compare to the other applicants?  What were people search for when they found my resume?  How many views did my resume get?  Did anyone even look at it after I sent it in?

2) LinkedIn is masterful at making you think you should be on there, giving you the impression that you'll be networking, and then having you scratch your head as to what the point is.  The problem is that Linkedin has the incentive to get you on, but not have you actually do anything.  Don't take my for it... these people were pretty easy to find on Twitter:

I personally use it a ton, but if everyone used it the way I do, it would be a noisy mess.  Since they broker access to your profile information, the fact that everyone's on it, without really using it, means maximum profits for the company.  Sure, they have a section about using it somewhere on the site, but if they really wanted you to get the most out of it, they'd take you right into, "Ok, so let's start contacting some people."  Instead, they leave you off right after, "Ok, so let's start adding some people."

3)  Got your resume on VisualCV or Emurse?  These resume on the web sites are supposed to help you stand out and get noticed.  Sure, they come up high when you Google your own name--but if someone's searching for your name (most likely you), then they already know you and most likely have your resume.  What about using these sites you actually get found and contacted?

Meet Carol Anderson.  She has her resume on VisualCV--it won an award as one of the best ones out there.  She's a Heathcare Consultant in Fredericksburg, VA.  It says so right on her VisualCV.  Try Googling for "Heathcare Consultant  Fredericksburg, VA".  She doesn't come anywhere.  In fact, you can't even find her until Page 3 of Google search results for Carol Anderson!  Sure, it's a pretty common name, but isn't the point of using one of these profile sites to rise above the rest?  You're certainly not going to rise above the rest on Google--VisualCV only has 9,000 pages on it's site exposed to the search engine.  Either only 9,000 people have created VisualCVs, or the site is keeping all of the people who joined under wraps--certainly not what people who wanted to "STAND OUT!" and get noticed probably want.

Emurse is a bit better, exposing nearly 200,000 profiles to Google.  However, they're not optimized to get you found for much more than searches for your name.  Brian Robertson sure wants you to hire him as a freelance web developer, but good luck finding his Emurse resume in Google searches for "freelance web developer st. charles, missouri" on the first page.  How many could there be? 

4) TheLadders has a great business model...for TheLadders.  You pay monthly to see jobs paying over $100,000.  It doesn't take a genius to figure out what their incentive is--to keep you on the site as long as possible.  If you get hired, you leave and TheLadders loses out on it's revenue.  That's not really the kind of model that makes me feel like a site is trying really hard to get me a job.

5) Jobfox tries to be a lot smarter about matching you to the right opening, but unfortunately they suffer from a classic chicken & egg problem.  The only jobs you can be matched for with Jobfox's highly scientific approach are openings on Jobfox.  In the current economy, those are some pretty slim pickins.  It would be better if candidates could see what positions they would be best for even if there weren't positions open in those areas right away.  At least they'd have a clue where to look--on other sites.  

...and here are five ways job sites fail the recruiter:

1) No site actually understands the full picture of the candidate that the web has to offer versus just aggregating it.  Zoominfo just aggregates everything it thinks it found about you (and some stuff it finds about other people) all in one place.  LinkedIn doesn't understand that even when you don't write "Python" on your profile, someone with a link to their "py.hack" blog and who tags things python in del.icio.us should come up in a search for Python developers. 

2) Search is horrific...everywhere.  Try to find the resume of someone with two years of sales experience with a Chemistry major who worked for a large company in a certain geographic area who can speak Spanish.  This should be a lot easier--and it's why you tend to get spam from recruiters on job boards.  It's not that they want to spam you--they just can't target *and* scale at the same time.

3) No reptuations:  A spammy, underhanded recruiter looks the same as a recruiter who takes the time to get to know candidates and send them relevent stuff.  In nearly every other kind of marketplace, both buyers and sellers have reputations.  Why not in recruiting?  (And no, a few "thumbs up" notes in LinkedIn doesn't count--I'm talking something that says 78% of candidates feel that this recruiters offers are relevent).   

4) We all know that someone updating their LinkedIn profile and adding people is an extremely strong signal that they're packing up to leave their job.  Why not expose this data and let recruiters search on it--maybe even pay a little extra to get out in front of the pack with exclusive access?  Recruiting is falling behind in "real time search" and the "now web".  The whole thing is based not on the blog post that a social media marketer posted just a few minutes ago, but what someone listed on their resume as their job six years ago--and that needs to change.

5) No "soft" data: We search resumes as if candidates like everything they did in the past and want to do it again---even though we know that isn't even close to being accurate, maybe not even half the time.  Doing something simple like asking people if they liked their job would be a huge leap in helping recruiters find people enthusiastic for their offering--not to mention collecting more descreet data about the types of situations they find more satisfying.  Now start laying on things like work values, personality, etc., and for a lot of jobs, you might not even care to see a resume.

Have we solved all of those problems at Path101.com?  Not yet--but we have key data infrastructure in place.  The very philosophy on which we are building out our product and laying out our roadmap is fundamentally about this data-driven, candidate centric future marketplace.

That's one thing that we believe strongly--that unless every single line of code, every business decision, every design choice is made with the jobseeker and their data in mind, you're going to get left far behind.  Imagine creating a "green" car company from scratch versus thinking you can make GM green tomorrow.  It's probably already too late for the existing players, but this market represents a huge business opportunity for anyone that understands that the candidate comes first and depth of data is your business--and the only way you get there is by getting the candidate to want to give it to you because they're getting something useful back.  

What's the last time you got something useful back after submitting your data to Monster.com? 

Exactly. 

How long do you think that lasts?

Are you stuck in a rut?

Don't like what you're doing, but can't figure out how to get ahead, or get out?

Ask for career advice on Path101.com on May 1st -- May Day -- as part of Path 101's "Career Mayday" Advicefest.

Path 101 has built up a community of career experts and experienced professionals to help get answers to your most pressing career questions.

What's even better is that when you ask or answer a question, you can connect your Path 101 account to Twitter or Facebook to help get answers from your network.  Check out some of these great questions and answers from our site:

Best tips for interviewing

Are unpaid internships worth it?

Staying in touch after an interview when there isn't an opening right now

Tomorrow, when you ask a question and connect your Twitter account, the Tweet will look something like this:

Mayday! Mayday!  My career needs help!  Please help me get an answer to my Path 101 career question.  http://bit.yl/32vwesd #mayday Plz RT

When you answer, it will look like this:

Just rescued someone through Path 101's Career Mayday.  Save a drowning career, give advice: http://bit.yl/32vwesd #mayday Plz RT

Just make sure you connect your Path 101 to Twitter...   After you ask or answer, at the bottom of that question, you can click a link to make a connection.  If you ask anonymously, we can't publish the tweet either (but that shouldn't stop you from just asking a question, of course). 

Sometimes, it takes you longer to realize things about your own business--especially somewhat obvious (in hindsight) business analogies.

I was thinking about Mint.com, the personal finance site, and I never realized how similar our goals are at Path 101.

Mint is building a suite of free tools to help manage a mainstream problem that effects everyone--in their case, managing your budget.  Their target audiance?  What about... everyone who makes money?  Spends money?  Wants more money?  It's a pretty huge potential audience and we feel the same way about our career guidance site.  Path 101 is targeted at anyone who works and wants to figure out what's next.

Now, the argument could be made that not a lot of people who make money actually manage their money well, which is what I thought initially about Mint.  However, Mint is making their tools so easy that they're not just converting the beancounters, they're helping people who have never ever kept a budget before--introducing people to the concept of budging and personal financial management.  We want to do the same for careers.  Thinking about your career can be an intimidating thing and we want to shed some light on the process and make it easier. 

Mint.com makes it easy for you to upload your financial data to the system, but moreover they give you a compelling reason to--to get recommendations and gain insight into your budget, the same way we want someone to get value from uploading their resume and other information.

This enables Mint to gain a tremendous information advantage from a business standpoint.  By working hand in hand with their users in managing their finances, they are the best positioned to broker offers from people who want to access those users.  That's ultimately where we want to be with Path 101.  By getting to know our users better, because we helped them manage their career, we'll ultimately be the best place to broker recruiter and employer access--particularly given that we'll know so much more about each user.

They're also using the network effects of having all that user data to improve the product.  The more Mint users there are, the more insight they get into trends and norms, which can, in turn, be presented back to the user in a useful, comparitive way.

It's a business and product model that no doubt works in other areas, too, but I feel like Mint is a particularly relevent comparison given the size of the potential market, the importance of this aspect of someone's lifestyle, and the focus on data.

Path 101, the company I started with our CTO and Co-Founder, Alex Lines, is looking to hire a developer.

Over and above anything else, here's the kind of person we want:

• Someone with a sense of ownership and pride in their work.  We get that nothing can ever be perfect, but you need to constantly strive to make things better.  This means not only making stuff works, but that it's easy to use and makes sense--and that you try to make it easier to use and more interesting everyday.
• You see the bigger picture--you realize that there are really exciting things to work on and then there's bug fixing--but at the end of the day you're happy we're moving forward as a team, as a company, and as a product. 
• You really hate when stuff breaks or it sucks and it keeps you up at night.
• You're friendly and/or interesting and are just cool to hangout with--not too uptight to break for a snowball fight in the park or to randomly pass funny images to the rest of the team on chat.

As for the tech stuff, an intelligent, curious, ambitious person can learn anything, that's true, but ideally you'd be an intelligent, curious, ambitious person AND be as much of the following as possible:

• experienced web developer
• very strong understanding of python
• extensive experience with django - you know its strengths and
  weaknesses, its ecosystem of libraries and components, participate in
  django community <-- This is ideal, but if you're strong in python, let's chat.
• obsessed with performance
• you can talk for hours about caching <--Alex's criteria, not mine.  Don't talk to me about caching... ever.
• experience with mysql
• know how to properly normalize a data model as well as the costs and
  benefits of denormalization
• strong unix/linux background
• conversant in html/css/javascript
• familiarity with column-oriented / key-value stores is a plus

We'll accept a resume but prefer a link to your blog and linkedin profile.

Here are some things you might what to know about us:

• We're helping people figure out their careers.  While this might not be feeding the poor, helping someone figure out what they want to do that makes them happy can really make a significant impact in someone's life. 
• We're doing it in an innovative way--by crawling the web for resumes and laying on interesting user data, like personality, blogs, tags, anything you want to tell us about yourself--in order to figure out what everyone's really doing with their careers.  This way, we can help you put your career in a context and figure out what "people like me" do for a living.  There are around 10 million resumes out there and we're going to crawl every last one of them.
• We're funded by some seriously smart and successful angels like Roger Ehrenberg, Fred Wilson, Brad Burnham, Scott Heiferman, Jeff Jarvis, Hunter Walk, Jeff Stewart, Peter Hershberg, Joshua Stylman, Brian Harniman, Shripriya Mahesh, and others...
• We were the first company to ever get an investment by the recently launched NYC Seed fund. 
• We're really passionate and dedicated to what we're doing.
• Team:  Charlie (@ceonyc), Alex (@alexlines), and Hilary (@hmason), as well as some super awesome contract folks.

So, tweet @ us, e-mail us, or leave a comment.   But please, no recruiters.  We can't afford a recruiter, so there's really just no point to reaching out.  We're really serious.  Really.  Serious.

Whenever I ask anyone for innovative ways to reach reporters, PR professionals point me to Peter Shankman's Help a Report Out (HARO) list. It comes out three times a day and gets sent to over 50,000 people. Reporters can post requests for everything from housewives who've discovered tantric sex to people who've turned down CEO positions (not *those* kinds of positions).

This is the bleeding edge of media relations, folks--a mailing list.

And thank God for this list--lest we all depend on these hand edited media databases selling for thousands of dollars. These sites make me feel like I'm searching Proquest back at my college library in 1999--cumbersome to search though and lacking the metadata I need to find what I'm looking for. 

At least HARO gives me a sense of what a journalist as actually looking for *today*.

Do you know why there are half a dozen of these things out there?  Most of the data is public!  Media winds up on the web, so all the data is already out there.  So far, I haven't seen anything that provides really specific insight into the current topics of interest of a reporter, nor any real analysis into how much traffic, buzz, and influence a journalist really has.  The blogger information is quite rough, too.

And @microPR?   I track it on Twitter... and it seems to be mostly people suggesting other people follow it for #followfriday or talking about its usefulness.  Fail.  

PR is a marketplace--an exchange of relevant, interesting information for attention and audience. So why doesn't it have the tools of a marketplace?  PR tools shouldn't look like databases... they should look like financial trading platforms, with asks and bids on a ticker--filtered for what I'm looking for or need.  This is trading: I give a reporter information (and an angle to work with) about my company and he gives me his audience's attention--at least to the extent he influences it. Real marketplaces have transparency, quantifiability, uniform elements of exchange, and the information systems that enable both sides to make informed decisions.

Imagine if you bought and sold stocks the same way PR works today.  You'd maybe list your name (or have someone else list you with questionable accuracy) in a database.   Instead of really detailed information related to your risk tolerance, prior stocks purchased, key financial criteria like cashflow, all people could see was a general description that you were interested in "Tech Stocks".  Nevermind that you're specifically interested in bigger name plays like MSFT, GOOG, and AMZN, you now get tons of requests for you to buy tiny little biotech companies with no profits that you've never heard of.  You get these requests in your inbox...and they just keep coming.  You don't have time to answer them and there's really no good way to inform the investor relations world about your interests.

PR,specifically pitching, is just like Wall St.--in the 1780's: Manual, opaque, and lacking the tools to create real actionable information flow and analysis. 

Getting PR is all about recreating the work that lots of other people have done to find good contact lists, which will always be incomplete and never really that accurate, crafting good pitch letters, which is totally not scalable, after hours schmoozing, and brokering exclusives in a world where information just wants to be free. This is why the startup geeks can't hack it and need to hire firms to do the social dirtywork.  They're too frustrated by the archaic process, lack of feedback and randomness of success to count on it as a good way to spend their time--especially when most media drives a seriously underwhelming amount of traffic.

Here's an idea for a better system--one that treats PR like the information marketplace that it really is:

First, index all of the reporters.  A good web crawler should be able to recreate the best online media databases in a very short amount of time. Match them up with feeds for their stories, twitter accounts, del.icio.us tags, etc., and analyze the topics and keywords they talk about in real time.  Also analyze the words that other people use when tagging, tweeting, and reblogging their stories.  I don't just want a list of career columnists who give resume tips. I want to know who is reviewing career websites and who isn't--and specifically ones focused on data and analytics or who have an interest in startups and innovation.  Computers can figure that out a lot faster than people can.

Media outlets need the same thing.  They need more information to sort through the pitches in their inbox.  Who are these people?  Are they backed by the right people?  If I were a reporter, I'd want to know that Path 101 is funded by folks like Fred Wilson, Brad Burnham, Scott Heiferman, Jeff Jarvis, etc., and has recently appeared in CNN/Money, VentureBeat, and Mashable.  Moreover, the fact that I was #61 on the SA 100, or that Hilary is a regular FooCamper might be of interest, too.   I'm not bragging...  I'm saying that if I was a journalist and thought of the PR process as an exchange, I would certainly equate some value the networks of the companies I choose to write about, all other things being equal.  I know I certainly go out of my way to try to connect up reporters who've helped me out with other people I know, like angels and VCs involved with us, their portfolio companies, etc.  If nothing else, reporters undoubtedly need some kind of filter, short of a background check, to figure out who's even legitimate.  I know I needed this when I was on the venture capital side getting inbound biz plan pitches.  Just because someone has the money to hire a PR firm doesn't necessarily make them the kind of people I might want to get involved with--but the interwebs can tell me a lot about "counterparty risk"--who I'm getting into this trade with?

Create a filterable, searchable open market for requests and pitches, with APIs, like Twitter, so I can have it on the web, desktop, e-mail, etc.  Mailing lists and Twitter accounts are archaic... and force people to sift through a whole bunch of irrelevant stuff.  When a reporter asks for new resources for career guidance, not only does that person get our Path 101 info, but so does anyone else writing something similar. Give reporters the analytics around how much coverage a company is getting, how recent, etc--make the whole process transparent.

With historical analytics, I should be able to go back in time and say "Show me all of the reporters that wrote about NotchUp and sort by rating and by most recent date of relevant stories."

At the same time, reporters should be able to create saved searches for "career resource", "career guidance", etc. so that they can see a running ticker of what's being pitched.  Why should they have to wait to be pitched?  When investors want companies that have Low P/E's, they can screen for that.  Why can't reporters screen the universe of pitches?

Allow for ratings on both sides. Some reporters write really thoughtful pieces, even when negative, and others are obviously mailing it in.  Let PR folks and companies rate the reporters. Undoubtedly, some startups are a total PITA.  If you get spammed by the same startup everyday, as a reporter you should be able to ding them.  It should be easy for a reporter to find out who is generally useful to talk about a particular topic regardless if they have something to pitch. Rating expertise on both sides would be great.

The other thing about ratings on pitches would be to allow specific feedback.  If I pitch a reporter, they should be able to easily click something to move on to the next one, but at the same time give me some feedback.   A stock set of responses to choose from would be great: 

"Interesting, but I have enough for this request already."

"My mandate has changed."

"Too early."

"Not relevant."

On top of that, they could suggest future contact with another click:

"Let's talk in the future."

"Please don't contact me anymore."

"Let's talk right now.  Call me."

Otherwise, your pitches will probably go into a black hole.  Who has time to respond to every single pitch they get by e-mail?

Also, let's come up with some objective ratings on traffic and influence. Did the story drive any traffic? How much? Was it reblogged, tweeted by others?   Did the users convert?  This is really what companies care about.  It's great that a site gets a ton of traffic, but if the users from that site never convert, what's the point?

What would this do to PR firms?  The general availability of great financial research tools to the public hasn't made the mutual fund and investment manager industry go away, has it?  No.  So there's no reason to think that PR firms need to go away.  Great tools should be able to cater to PR firms and individuals at companies who want to do their own PR alike, the same as in investing.  We're far from great tools at the moment and what's out there costs entirely too much for the amount of work it still leaves you with. 

"I sent a cover letter. It should be getting me that job now."

"No, Lieutenant, your job search is already dead."

Alison Doyle defended cover letters today and was rather dismissive about the idea of finding your job by connecting to someone using social media.  I won't take up the social media debate now, but I will put to bed the idea that you should spend any time whatsoever on a cover letter.

What gets read first, a resume or a cover letter?  Ask anyone who has ever hired anybody in the last twenty years.  The answer is a resume.

Here's the short version of the proof, then:

Is your resume awesome? 

If no, then I'm throwing it right in the trash, along with the cover letter, which I didn't read, because your resume isn't awesome.

If yes, and it does not come with a cover letter, will I contact you?  Of course!  Half the resumes I got were from resume databases or LinkedIn, so much of the time, a resume or profile is all I have anyway.

Once you get contacted, then it's up to you and who you are... and that's what you were trying to do with the cover letter in the first place--get a response.  No hiring manager has ever contacted someone with a mediocre resume who wrote a really nice cover letter.  They never get to the cover letter of a mediocre resume--they don't have time!  If they say they did, they're lying to make it seem like they do extra work like read all the cover letters than come in.  I'm sure they don't rip the tags off their pillows either. 

More important than a cover letter, if a resume contains a link to a site, I am going to visit it.  If this site is a blog, and you write about your passion for the industry you're looking to get into or your insights, I'm going to be pretty damn impressed.  I certainly won't ask for a cover letter after that.  Think of this like rock, paper, scissor.  Resume beats cover letter.  Awesome blog beats resume and obviously also beats cover letter. 

No, you can't submit the link to your blog on the front end of a company website, but would Alison suggest that if I was hiring someone to run the career guidence office at a school, that being the About.com job search guide since 1998 wouldn't be enough?  Why would you even ask for a resume at that point?  When I left Oddcast a year and a half ago, no one asked for my resume, but I got 25 job leads from people who had been reading my blog for years.  Cover letters?  What's a cover letter?

Well, Alison defines a cover letter as "...a document sent with your resume to provide additional information on your skills and experience."

She suggests the following format:

1. First Paragraph - Why you are writing
2. Middle Paragraphs - What you have to offer
3. Concluding Paragraph - How you will follow-up

You know, because that's the "basic format of a typical business letter."

A typical business letter?

Has anyone actually received a "business letter" in the last five years?  (Besides ones from daughters of Nigerian generals looking to deposit money in your bank account or official looking solicitations for credit cards.)

Today, professionals are sending one line e-mails from their Blackberries that affect millions of dollars.  Have you ever seen what three paragraphes looks like on a Blackberry?  It might as well be Paul's Letter to the Corinthians.  People want just the facts, as quickly as possible.  Three paragraphes of prose and I'm either on to the next e-mail or I'm asleep.

It's funny, because, today, she expanded her definition of a cover letter to include "via email or a LinkedIn message".   Can you even type three paragraphs into a LinkedIn message?  I'm pretty sure there's a character limit, and if there wasn't, I'd think the person was just trying too hard or didn't really understand normal behavior on that site.

Twenty years ago, cover letters served a purpose.  They introduced who you were and how you found the position--because before widespread use of the internet, how you found anything was actually interesting.  Now, asking how you even know someone is becoming a joke, because we're hyperconnected.  As for who you are, we all know that your cover letter is your marketing pitch--no hiring manager takes that seriously.  They'll do their homework to figure out who you are.  They'll ask Google, Facebook, and LinkedIn who you are, who you're connected to, etc... and if they can't find you there, for a growing percent of the few available jobs, you might as well be persona non grata.

In today's world, if you're contacting someone you don't already know to get a job, you've essentially already failed.  It's too easy to find people and use your network to reach them that coming in without a recommendation reflects pretty poorly on the candidate.  If I was going to hire you to do sales for me, I certainly wouldn't expect you to just cold call all your leads.  I'd hope you'd at least figure out how to be innovative and networking savvy enough to find your say to a warm intro.

And yes, I know, not everyone uses the internet, and not everone can afford a computer, and three quarters of the world lives under the poverty line--I get it.  It's a terrible situation, but we're talking about job advice written on blogs.  There's a clear target audience here of people who have some amount of advanced education, socioeconomic mobility, etc.  For *those* people--if you're thinking a cover letter is going to get you anywhere, you're wasting your time.

There are also some jobs out there where your digital presence just doesn't matter at all because you're basically talking mass hiring of a certain particular skill.  Take nursing jobs.  Hospital systems need to hire 1000's of registered nurses a year.  So long as they have the right certifications and whatever references are needed check out, you're basically in, or at least in line.  Many civil services positions are like that as well.  However, not only does a digital presence not matter to be a police officer or a firefighter (Good thing for my dad, a 20 year FDNY vet), you also don't need a cover letter.

So let's focus on jobs that supposedly need a cover letter--jobs that are sought after enough where the candidate is looking to stand out from the crowd.  So we're assuming a crowd here.  Now put yourself in the position of the hiring manager.  Not only do you get 100's of not 1000's of resumes for each position that you have an opening for, but you're searching resume databases to find candidates, too.  It's physically impossible for anyone to read more than a handful of cover letters. 

Even resume expert Louise Fletcher says that "back when I worked as an HR manager, I never read cover letters".  Louise worked as an HR manager back in 1995.  She did say that her boss liked to read them, but assuming her boss was probably at least 5-10 years older than her, if not more, you're talking about a guy who started his career in the early 80's--almost 30 years ago.  Are we really giving advice to people on how to get hired by dinosaurs are should be dispensing advice on how to be the most innovative candidates out there and to try to get hired by the most innovative companies.

But Alison says "Innovation works for a lot of people/industries. Not others."

Everyone who wants to get hired into an industry that doesn't value innovation, raise your hand.

Ok, everyone with your hands raised, finish up working on those cover letters!

Businesspeople ask me all the time how to find a technical partner for a startup.  When they ask, it often sounds like they're asking for a product off the shelf--like, "Where can I get some cheap folding chairs?"

Finding a technical partner is more akin to finding a life partner than anything else--the difference being that neither party has any intentions to stick around for fifty or sixty years.
Where to find one is kind of an interesting question, because, like single men and women, there are certainly places they are more likely to hangout--bars and listservs versus bars and clubs--but going to one of these places is no guarantee of meeting anyone.  The key is getting out there--finding as many ways as possible to meet with people and get involved in activities around your interests.

The truth of the matter is that, actually, it starts with you.  No one wants to feel like they're joining less than half a partnership, in either sense.  Don't forget that this person is adding you as a partner just as much as you're adding them, so look in the mirror and think about what you bring to the table.  Think about it this way, if you have an idea and you're willing to give up half of your company to get a technical partner, consider the CTO's side of it.

They're giving up 50% of a company to get you as a business partner, because they probably have ideas, too--ideas they could potentially own 100% of and maybe get built in their spare time.  So, what makes you worth 50%?  (Or 60,70, or 80% if you plan on giving out less...)

Let's start with finances.  The ideal partner is financially independent.  For a startup, if you are a businessperson, a) Do you already have money to start the businesses?  b) Do you already have great investor relationships who will pull the trigger on funding pending the addition of a technical partner or completion of a product?  c) Do you already have clients willing to pay upfront for your product to see it get built?   As the businessperson, financing is just one of the things you bring to the table.  If you're answer is no or maybe to the above, what value are you to the business?  What value you are you to a partner? 

If your product is technically feasible, everyone around the table should believe it can get built.  Then, there's no reason not to have people who say "If you build that, I'd be very likely to buy that/fund that."  That would be my due diligence on you if I was a technical partner--lot's of people saying yes.

If I was a technical person with a prototype, and I was going to give up half (or more) of my company to a businessperson, what would I want?  I'd want a rainmaker.  I'd want someone with a huge rolodex of people already dying to get a piece of the action of this person's next endeavor...someone with so social capital built up with key influencers, industry partners, and investors that they don't know what to do with it.

So rather than trying to make it a process of "finding" you need to think about it as "attracting".  How can you make yourself, as a businessperson, more attractive to a technical person capable, at least from a product standpoint, of executing their own ideas? 

Here are a few ways:

- Get clients and customers.  The more people signed up or at least saying they're willing to pay for something if you build it, the more attractive your business is.

- Generate a buzz with key influencers.  If smart people are talking about your idea, technical people will want to be a part of it.

- Understand the tech.  You don't have to know how to code, but if your ideas are technically unfeasible or product discussions are going to be remedial, a technical person will just move on to someone who gets it.

- Be a leader in your own field.  If you want to make it to the top of the startup/tech heap, jumping from the top of your own heap is much easier than climbing from the bottom.

- Raise money from people who know you best--even if it's just a little friends and family money, a technical person will not want to be the first risktaker in the pool.

And yes, that picture is of Alex Lines, my co-founder at Path 101, which officially launches on Tuesday... and that's how I found him when I walked in at 7:50AM this morning.

We have equal ownership in the company and I'm pretty sure he got the short end of that stick.  :)

Fred Wilson recently wrote about whether or not entrepreneurs need a college education.  He wrote, "Education is critically important. But you don't have to go to school to be educated and if being an entrepreneur is your goal in life, that's even more true."

The other day I was having a discussion with a friend of mine who works in the food business.  She runs a cafe in a high-end, high-visabilty retail store--the flagship location for a very successful business.  I assumed she had a degree, but it turns out that she didn't.  She simply started cooking--went to Rhode Island and studied by working with some of Nantucket's most successful chefs.  She learned how to run a food business firsthand. 

Still, those stories are the exception.  People in most industries expect you to have a degree, and the stats show that you're more successful with that piece of paper than without.

However, the question gets a little trickier when it comes to whether or not you need that piece of paper from an Ivy League school or whether your local state school will do just as well.  Do you need an expensive degree?

Given the rising cost of a college degree and the current economy, more and more students are thinking about what the ROI of their education will be.  Does it really pay up to go to a "better" school?  And what does it even mean for a school to be better? 

If you're going to school with the goal of getting a good job, that would imply that graduates from better schools get better jobs--whether that means more responsibility, more pay, faster progression, or even more happiness.

Unfortunately, no one really tracks this.

US News & World Report tracks statistics like the percentage of professors with terminal degrees and what percent of the alumni base give back.  Given that we know that not all PhDs make the best teachers, and the alumni giving rate is a function of salesmanship of your alumni relations office more than anything else (or performance of your school's basketball team) then can we really count on these kinds of surveys to accurately measure the best schools?  They certainly aren't taking outcome--what happens to someone 1, 5, 10, 20 years after they graduate--into account.

So who knows that?  Anyone with a critical mass of resumes who understands different industries, job titles, etc. would know part of it--but you would also want more information.  Imagine if, after analyzing resumes, you could survey your alumni and ask them if their degree led to their success? 

Imagine students had that information even before they chose their college!

These are the kinds of things we're thinking about at Path 101 and we're looking to work with schools who want to get at the hard facts.  We're building a database of over a million resumes and analyzing careers.  We have a number of schools that have over a few thousand resumes represented in our database already and the results of how those resumes compare to their peers in the same industry are fascinating.

If you work for an alumni organization and you'd like to work with us to understand whether or not you are producing successful alumni, especially relative to your peer institutions, please contact me at charlie@path101.com.

Check out our presentation on this topic:

Here's the reality.  There are a lot of people out of work right now, and there will be more.  Unless you have some kind of technical skill, like brain surgery, web development or you can do some kind of theoretical math that no one else can, chances are there's someone out there more qualified than you or who went to a better school than you do--probably a quite few people in fact. 

The idea that you're going to get a job by dusting off your resume and uploading it to Monster is a pipe dream.  Even worse is trying to apply to the few job ads out there. 

Job ads are like crack.  Applying to each one is like getting a little hit.  It feels good that you're doing something, but ultimately they don't get you anywhere.  I once posted 12 positions for a company and got back 3,000 resumes.   The odds are not in your favor.

But if you apply to enough, someone will certainly see your resume and respond, no? 

Go ahead--apply to all of them.  That's what everyone else is doing--and half of all resumes that get sent to companies, maybe more, never ever get looked at by anyone.  There might not even be a real job behind that ad.  While you're at it, you might as well play the lottery.  At least someone wins the lottery, eventually.

If all you have is a resume, you're toast.  Your resume isn't special and it's not the best one.

Welcome to trying to get a job in the middle of a recession.

Oh, and e-mailing it around to all your friends?  If you look up "wreaks of desperation" in the dictionary, you'll see a page with an attached resume.  When I get unsolicited resumes from people I barely know in my inbox, I feel like I want to treat it like someone just handed me their dirty socks.  "Umm...  ew...  I know a good place for this..."

The problem with that is that the chances that someone you know is looking for your resume is so slim--plus asking them to send it around is kind of like asking them to spam people.  No one asked for your resume, so why are you sending it around?   Instead, take the time to figure out what it is your friends do, target the ones in areas you want to work in, and ask to chat with them on the phone or buy them coffee.  THEN, follow up with a resume, IF they ask for it.  That shows you know how to treat people like people, not like e-mail addresses, and you can go the extra mile to market something--yourself.  If you just blindly e-mail a bunch of people and expect a positive response, am I to assume this is how you'll act on that sales job a recommend you for?

Wake up.

You need to treat this job search like you seriously want the job--and that's going to take a different approach, some serious get off your ass effort and a little bit of time.

First off, let's be clear.  I get that you need to pay your rent and you need a job yesterday.  That's no excuse for approaching your job search like a mindless lemming--rushing to jump over the same cliff as everyone else who is out of a job.

Do what you need to do to take care of your financial priorities.  This is why it's good to have a few months savings built up.  If not, you need sure up your finances.  Immediately cut unnecessary expenses, but be careful not to cut too much--especially not the kinds of things that will de-stress you or get you out of the house everyday.  So, if you're choosing between cable and the gym...you might want to go without the tube for a while.  Sitting idly on the couch will not get you a job and will most likely make you feel bad about your situation after a while.  Besides, most of your favorite shows are available on the web for free now anyway.

The gym, however, can be a place to meet people and an excuse to get out of the house.  You need to get out there and meet lots of people, and looking refreshed and healthy goes a long way.  Get some sleep while you're at it, too... But don't sleep in--hit the sack early.  If you're sleeping in and not getting out of the house until noon, you're missing out on hours of potential job searching and networking time.

As for finances, don't be afraid to take paid work on a temporary basis wherever you can get it, even it's part time or not in your field--as long as you don't take your eye off the ball when it comes to really trying to get a job you want, in your field.  Despite the urgency of your situation, you can set your career back years if you take the wrong job just because you have to, and then give up looking for something else.  You should always be looking for better opportunities.  If you need to tap into savings, sell some extra stuff or move into a smaller place (or get a roommate) do what you can to ease your current financial situation--because being stuck in a hard financial spot can throw on a lot of pressure that will make getting a job (like being cool, calm, and collected on an interview) more difficult.

Ok, now for actually getting a job.  Let's think about supply and demand in this market.  Right now, companies have the ability to get just about anyone they want--so the question is, "Why would someone want me?"  You're probably not going to pick up some new skill between now and your next potential job interview, so the reality is that whatever skills and experience you have is what you're going into battle with.

So what else is there?

How about reputation?  Put yourself in the shoes of the person hiring.  You've probably been around a hire or had to hire someone yourself.  What's the first thing people do when they want to hire someone?  They go to their immediate network of trusted connections and see if there's anyone who might be a fit.  This happens even before they dive into the resume pile of people who are out of work--which isn't a very appealing task for most employers.

So the key is getting your name out there, far and wide, so that when that question goes out, you immediately come to mind.   How do you make sure that key people associate your name with the position you want?

Here are a few ways... and you should try all of them:

1) Be a leader among people just like you.  So you're out of work, or maybe you're just stuck at a cruddy job and you're looking to move up or chance paths.  Maybe you're interested in a hard to get into profession.  Either way, there are lots of people out there just like you, and if you can't just flat out beat them with your resume--then lead them.  You should get active in whatever professional society is relevant to your field.  Professional societies are always looking for more active members, especially if they can help out with events.  If there isn't a professional society, then start a Meetup.  Get other people with similar interests together in one place, and then reach out to experienced professionals to invite as speakers--or just to come to your networking events.  A friend of mine created a group for professionals interested in digital media as it relates to museums and cultural institutions, and in less than a month, it has nearly 100 members already.  What this does is not only places her in the mind of 100 industry professionals as an up and comer and community leader, but also when it comes to interviewing for jobs in this space, she has this unique feather in her cap.  She can say that she runs the Meetup for the very same professionals a company is looking to hire!

2) Informational interviews.  No, this doesn't mean going around asking people to hire you.  It means thinking of this job search as an excuse to get to know a lot of professionals.  If you're out of work, you should be meeting with, at minimum, three people a day for purely informational purposes--to learn about the different areas of your interest.  Don't go into a job interview not knowing exactly what's going on in a field.  Go in having talked to a dozen people over the last week about exactly what's needed for success and how the industry is changing.  Again, that shows interest, ambition, and it looks so much better than the person who can only say they've just been applying to a lot of jobs when asked, "What have you been doing?"   With each interview, ask the person for one or two recommendations of who else to talk to.  Never ever try to push your resume on someone... if they hear of something for you, they'll ask.  Resumes put pressure on people that they need to have an immediate job for you, versus just having a conversation. 

3) Keep your digital presence fresh, interesting, and up to date.  Be where people are online.   I told an out of work friend that she should start a blog about the tools she's using to organize herself online, since she needs to get organized to get her job search moving, and she's looking to be an interactive media producer--a position that demands a lot of organization.  She told me that she needs a job now, and doesn't have time to start a blog.   This is really short sighted, because what happens on the off chance that someone actually does find her resume and immediately googles her name.  Would she rather her smartly written organization blog be up there first, or just her Facebook profile with her silly profile picture--making her look like one of millions of other faces and resumes.  Whenever you get in contact with someone, be it asking for a job or an informational interview, they're going to check you out online, so you need to make sure you have a solid digital presence.  This can accomplish many things for you:

- It makes you seem more savvy than others who don't use these tools.

- It gives you an opportunity to write and share thoughts that can't be captured on just a resume--like a portfolio for a knowledge worker.  If you were a photographer, you'd unquestionably have an online portfolio available, so as someone being hired for your sharp business mind or what have you, where's your portfolio?  Your thoughts and options about your industry, or just about the tools you're learning about, represent an interesting aspect of you that a resume won't adequately put on display.

- It makes you more searchable.  If you use the right keywords, your blog will get a lot of search traffic after a while--and someone searching for an expert on organizing political communities might find your "How to organize a group of politically active people" post, if that's what you're interesting in.

It's also important to make sure your LinkedIn profile is up to date, and you've got your real life network on there.   Here's a post about getting started on LinkedIn.  LinkedIn is a great rainy day fund for people.  Use it to seek out informational interviews, find out if you have connections at places you're applying, and see what companies and what professionals are in your space.

A great listening tool (and publishing, if you feel like sharing) to see what professionals are talking about in your area is Twitter.  Twitter is a social network where people share shortform status updates, like where they're going or what they're reading, etc.  Knowing that there's a media exec on Twitter going to a particular event when you know you want to work at that company can be a significant advantage in the job search.  Tools like Mr Tweet can and Twitter search can help you figure out who to follow.

Want other ideas?

How about starting a project--the kind you want to get paid to do--on your own.  If you want someone to pay you to work for their advertising company, how about offering up some of your best thinking around brands and advertising to a startup--or a startup a day on your blog.  By writing up short case studies of what you think certain companies and brands should do, you'll have a good shot at attracting their attention.  Or, if nothing else, you can work on some of these case studies with people you want to do informational interviews with.  I once told a guy who wanted to be an information architect to start wireframing how Twitter would sign up groups of people at a time, and then publishing that on his blog for feedback. 

A project could be managing a fake portfolio of stocks on UpDown, but taking it very seriously and publishing your results and analysis.  It would make for a great discussion with a real portfolio manager--certainly better than, "So how did you get your job?"

At the end of the day, a job search needs to be active, and you need to be using all of the innovative tools possible to help you get what you want.  If all you're doing is sending your resume around via e-mail attachment, well, expect to get a good job...  in 1998. 

You can call in (646-929-1686) or check out the show online...   be there!

Topic:

With over 2700 blog subscribers, 1700 Twitter followers, 1000+ LinkedIn connections, and 600+ Facebook friends, not to mention IM buddies, 100+ blogs in my RSS reader, and 3000+ e-mails in my address book, you'd think I'd be a bit overloaded!

I'm going to talk about how I "manage" all of these and also take some questions around the following...Friend everyone or keep a velvet rope? Can you develop authentic relationships at scale? Where does networking cross the line to self promotion?  

Have you ever felt like you never realized how much you were capable of, because, simple as it may seem, no one told you along the way? Despite the fact that I went to a magnet school, I never strived to be a leader in high school or to discover the unique imprint I could leave on the world, mostly because I just didn't realize that I could be on the same level as the high achievers.

And yet, somehow we assume the US is going to retain a leadership position in the world over the decades to come, even though we really don't spend much effort at all on leadership training.

Sure, we have lots of leadership problems. The top of every class get special awards, plaques, and wind up on lists, but how many of those students are actually getting the leadership tools they need to impact cities, states, countries, even the whole world?

What's worse, how many are being told they can?

What passes for student leadership these days is often pretty lame. Lead a club that had been on campus for generations. Get elected to the student council and run a new program. This will put you in the top 10% of your school in terms of leadership, but that's a pretty low bar, since we all know most students don't try too hard to be leaders.

The difference between that and being one of the top 30 under 30 years of age in your profession is huge, and most people don't know how to teach or motivate for that. In fact, I'm not sure they even try, because much of that level of achievement involves reaching across institutions and changing the way things are done, something most schools aren't even good at themselves.

Imagine, for a moment, what the top 30 people in your profession under 30 years of age are probably doing. Or the 25 under 25. Maybe your industry actually has that list . Maybe you need to create it. Identifying standout performances could help motivate yourself and others by identifying just how high the bar really is.

Many people don't strive for leadership because they don't want the pressure and responsibility that leadership comes with. What they fail to realize is that it's actually much easier to be a leader than being the low person on the totem pole. Leadership brings with it the flexibiliity to do more on your own terms, and the support of others who follow you who can help lighten the load because they believe in your vision.

So if you're a college student or in your 20's, think about what you need to do to be recognized as one of the top people in your field at such a young age--part of a 30 under 30. If you don't know what that would entail, go ask anyone and everyone that you know who is involved in the industry what it would take.

Publish the answers, strive the the goal, make an impact, because who really wants to ride in the back seat for this lifetime?

I've said this before, but I'll be honest:  I never wanted to be an entrepreneur.

Well, I never wanted to be an entrepreneur when I knew what being an entrepreneur was.   Back when I was like 10, I wanted to have my own car company.  I used to draw cars and I'd make annual reports on our computer using Harvard Graphics.  I called it Impulse.  I liked naming the models. 

When I started working in private equity, it didn't seem nearly as appealing.  It seemed like a huge pain in the ass for not a lot of reward--on average.   Sure, I had done entrepreneurial things in college, like start a business newspaper, but I was never any good at delegating and so while I enjoyed my experience, it was kind of all for naught.  The paper died when I graduated, after two years.

What I didn't realize then, and what I'm realizing now, is how much I enjoy the challenge.

People ask me if I stress--if I stress about the fact that I know the very day we run out of cash.  Do I stress when investors turn us down or when we need to make difficult product decisions?  Do I stress when something on the site doesn't work as its supposed to?  Do I stress over the hours I put in?

Not in the least.

In fact, it's fantastic.  The challenge of it all has been enormously rewarding.  So as I sit here getting ready for a big investor meeting... a  "go/no go" final meeting... one where I'll be giving a pitch that could be worth nine more months of life for the company, for my partner, for my employees, for our investor's capital...  I'm really loving it. 

This is way better than the day that I was interning at a big company and I left for the afternoon after lunch and no one noticed that I was gone.

I live for this.

If you didn't happen to catch the live show, here's my interview yesterday with Sumaya Kazi of Socially Speaking on BlogTalkRadio.  We talked about social media, startups, and even the New York technology scene.