I'm pretty sure I'm not allowed to fundraise according to the SEC, so let's just play hypotheticals for the moment... wink wink, nudge nudge.

IF I was a startup looking to raise seed money for development of a project, ooh.... something similar to Path 101 (I think I've settled on having a space there), and raising somewhere between 250-450k, what should the makeup of that round look like?

On one side, not many VCs would even do such a round pre-product, but a few of the would.  There are
some smaller, perhaps more specialized funds that do this sort of thing.  Either way, these are people that are primarily in the business of investing in startups.  To me, the benefit is that they have experience, connections, and they (ideally) have a sense of professionalism around the way they conduct their business.  (i.e. They're not going to show up at your door one night demanding their money back.)

The one thing I don't necessarily believe is that it makes them any more likely to invest in an A round.  Sure, they've gotten a chance to get to know you, but if a VC is interested, they don't need to put in 200K to do that.  They can take you out to a few lunches and hang around the rim enough to see what you're up to.  Plus, if you don't wind up coming out with a compelling product, they're free to just walk away from the deal anyway.  At least with angels, there isn't an expectation that they're going to participate significantly in an A round, so you won't have egg on your face if it doesn't happen.

As for angels, you're likely to need them at this point, so I think the question becomes more of a question of composition.  Friends?  Family? Big names?  Angel groups?  A mix?  How many?

If you can, I think its advisable to avoid friends and family, unless you have friends and family in the business that you're going into, whether its tech or something else.  You'll need their moral and emotional support and you should let them know that's what's important.  You don't want money, or lack of it when the company blows up, getting in the way there.  Plus, unsophisticated investors, even if it's your mom, are probably going to be a little bit of a pain in the butt.  (Although, Jeff Bezos' parents turned out to be good angels...)

I think a mix should probably be in order.... the professional investors that you know best, and also a few "reach" candidates.  If you could get anyone on board--captains of industry, celebrities, etc--who would it be?  For me, I think anyone on the founding teams of Monster, Careerbuilder, or Hotjobs would be perfect.  Published authors of books like "What Color is Your Parachute?" would be ideal, too. 

But I'd like to hear from entrepreneurs.  What's been your angel experience?  Surprises?  Who's been a much better addition than you expected?  Who's been a disappointment?  VCs in angel/seed rounds?

Yesterday, my brain ceased to function for about 3 minutes.  It was scary stuff.

I was supposed to meet with a VC about Path101 (or is it Path 101?  Space or no space?) and they e-mailed me saying their flight was two hours late.  So, I figured that was the end of the meeting and replied that we could talk on the phone in the next few days.  I was at the Web 2.0 Meetup at Slate and I was starving.  So, I ordered myself a chicken panini with gouda. 

Fifteen minutes later, the VC calls while in a cab coming over from a meeting in Jersey City and asks if I'm available to meet for dinner.  He had dinner scheduled originally with someone else, but he was going to bail on it to meet with me.

Here's where the 3 minutes begins.

I told him that I had ordered a little while ago and suggested maybe we could meet up after our respective dinners.

When I got back to my conversion with Kristian, he said to me, "So a VC that you really want to work with offers to cancel his dinner to meet with you, and you pass because of a nine dollar panini?"

"Oh...  wait... . jeez...  That was really stupid wasn't it?"

"Yeah."

"Dammit... I gotta go call him back... what was I thinking?"

I'll tell you what I was thinking...  I didn't want to waste food.  Years of my mom scooping extra servings on my plate so that she didn't have to throw anything out just hardwired themselves into my brain, cementing a pattern that would be highly sub-optimal in this situation.

So I paid and bailed on the panini...  told the waitress to enjoy it... and left for dinner after calling him back to let him know I was totally free to meet up if it was still on the table.  Thank God it was.

"Yeah... I could have had a $500 million exit...   if it wasn't for that $9 ($12 with tax and tip) panini."

When I was eight, we got a computer.  An IBM PS/2 with an 8086 processor and a 20MB hard drive.  That was 1987—twenty years ago.  My only experience with coding, however, was the C-logo class I took in school that year.  Man, could I make that turtle rock and roll…  I was the C-logo master.  But, I never followed up on it at home, because our home computer wasn’t for hacking.  It was for my dad’s business.  Quite a few times, I got lectured for not reading the MS-DOS manual first before just playing around on it.  That was pretty much the end of my coding career, which means that, today, now that I want to build Path101, I need someone’s help. 

I can always go outsourced--to some team of Uzbekistanians (Uzbeks?), but I want to do more than just get something up.  I want to be able to break out of the echo chamber and work with a true partner—not someone who may be gone from this project in three months.  There’s no substitute for a real live human in the same room as you who has his or her own dry erase marker at the whiteboard.  Even virtual teams will tell you that the most productive sessions are the ones they have in person. 

So, in the spirit of uber anti-stealth, I’ll put my conceptual thinking for the build and the structure, as well as what I’m looking for in a partner relationship, in the hopes that there’s someone out there who not only sees the value, but has the same philsophy on how to create this. 

First of all, whoever takes this project on has to be a data jockey.  The real value of a Web 2.0 app is the leverage it can get out of its data—the data it pulls in, the data it pushes out and the mashup of data in the middle.  Every piece of data that comes in or out of this thing needs to get used 8 different ways if we’re really going to knock socks off.

Example:  Imagine a student is using a resume building tool.  You shouldn’t have to create a resume for paper and a resume for LinkedIn and a resume for Facebook.  Using standards like hResume, they should be able to use the resume wizard once, then populate a LinkedIn profile with the same structured information that we popped out a fancy PDF version to send out by e-mail.  But let’s go a step further...  Let’s say that a student participated in a special summer program related to their major at a local college—a two week immersion course on financial modeling, for example.  The enter it in the resume wizard.  However, our structure means that we know the dates, we know the location, and we can ask what this thing was—a course?  A scholarship program?  An internship?   We should allow the student to be able to publish that information to other students with similar interests.  That’s how I found out about the mentoring program at my local financial professional society.  Someone a year ahead of me went through it the previous summer and suggested I participate.  The information about that course was on her resume, but for it to get into my head, she had to bump into me randomly in the cafeteria—a lucky break for me.  Efficient use of data structures and matching would have put that program and the 8 other summer programs just like it in front of me when I was thinking about my summer. 

You might ask why would students allow that to happen?  Aren’t they competing with me for the same jobs?  Not if they’re a year ahead of me in a different recruiting class.  Plus, perhaps they understand (or we can teach them) the value that sharing a summer program with me this year means that I might send a job opportunity their way at my company next year. 
     Just as an aside, one thing that also seperates Path101 as a business from what’s out there is our philosophy of giving as much value back to the students as possible.   Think about that aggregated dataset—all those college resumes with all those positions.  Monster has them.  They know where almost every college student interned last summer.  That’s about as close to the total universe of available opportunities as you can get, but do they expose it to students?  No.  They show those resumes to recruiters who pay for the access to the students and they show you the jobs that people pay to list, leaving the larger universe of opportunities to rot.  That’s their business.  All those random little companies that you’ve never heard of that provided some really interesting internship opportunities—ones that never get posted at $250 a pop because the company can’t afford it—are being wasted by Monster and not shown to students in order to protect their own bottom line.  Millions of students worked their butt off to research and network their way to internships they couldn’t find on Monster, especially in the non-business areas.  Monster sits on that useful data, leaving next year’s students on their own to recreate that whole research process all over again.  No wonder it’s so hard to find a great internship.  That’s not the way Path101 is going to create value for students.
     In addition to trying to get the maximum value creating leverage for every piece of data, whoever works on this build needs to believe in portabilty of the application.  Its not just about Facebook either, which obviously a student needs to be able to access all of our services on.  One day, before they buy us, Monster may want our whole application to appear on the Monster site, or the NYTimes, or the PR Society of America.  Schools may want this to appear on their sites and we can’t afford extensive enterprise integrations with every school.  Integration needs to be a matter of skinning, cutting and pasting iFrames and code, and incredibly robust APIs—caveman style easy…but I’ve been beating that horse to a pulp lately.   
     Also of major importance to me, and maybe this is most important, is the platform this is being build on.  No, its not Java or LAMP or Ruby on Rails—it’s TRUST and RESPECT.  I need to be able to trust and respect the insights of someone who has built a scalable application before and that person needs to trust me that I’ve actually been in the classroom with college students, mentored them,  and talked to them about their career aspirations.  But it goes deeper than that, right?  It goes far beyond the 1’s and the 0’s.  I had a VC ask me what I would do if Facebook offered me $10 million for this site in a year once its up in 25 schools and growing.  As a co-founder, perhaps that nets me $2-3 million after tax—not too shabby for a year’s work.  You know what, though?  That doesn’t really change my life much.  Plus, I honestly don’t consider myself a serial entrepreneur.  This is my idea.  Will I have another one?  Maybe.  Maybe not, and if I don’t, $2 million basically gets me a nice apartment in the city.  I’m not really about to trade in my big idea for a nicer apartment—that’s not enough for me.  What I really want to do is to be able to tour the country talking to college students because I’m the guy who started the service they use day in and day out to pursue their passions.  I want to hear about the paths they uncovered and the people they met.  I want to get a letter from some successful entrepreneur ten years from now who tells me that they didn’t even know what entrepreneurship was until they logged on to Path101 and started exploring.  That’s what value is to me.  If I was just in this for as quick money, I would have spent the first two years of my career burning myself out as an investment banker. 
So, in a since, what I’m building… well…  This is going to be BIG.  At least I want it to be anyway…and perhaps one day we’ll capture the even larger opportunity of career changers, moms returning to work, people laid off at 50…  even goals that aren’t necessarily about career stuff. 
Whoever joins will be a signficant equity partner, be able to get his hands dirty in the build and also manage a tech team.  I’ll be honest—there’s been some strong angel/VC interest in this (over and above folks you might guess on your own) and so it seems likely the team will be able to be focused and fulltime for six to nine months. 
So that’s me and that’s a little bit about what Path101 is looking for.  Maybe you’re sitting in a big media company twiddling your thumbs itching to get back in the startup game.  Maybe you just had a successful exit or a big blowup and you’re looking for the next thing.  Maybe you’re at an early Web 2.0 startup and the writing’s on the wall that it isn’t going to wind up inside Google anytime soon.  Let’s talk.   

As a general rule, I never signed an NDA while I was at USV.

I was also recently talking to a startup about potential employment who wanted me to sign one, too.  I balked.

I've been banging the transparency drum for quite a while--the idea that you should tell as many people as possible about what you're up to and not worry about keeping your idea a secret.  The basis of that is as follows:

1. Chances are that if your idea is a good one, in a big enough space, someone's already had it, so you won't really be tipping anyone off.
2. It doesn't take long to build anything, so even if you kept it secret, at most you're going to have a three or four month headstart, which is pretty meaningless in the grand scheme of things.
3. The idea isn't nearly as valuable as the execution.  You could say you're going to build a LolCat maker, but if you can only use one kind of cat, its not going to get any traction whatsoever.  The devil is in the details.
4. Speaking of the details, you're likely to get them wrong the first time anyway...or learn more as you go along, so your first idea is never really a good one.   

But the question is, will I eat my own dogfood?  I had a conversation about this with an entrepreneur a little while ago and we both agreed that when its your own startup idea--the one you're really passionate about--there's a slight bit of hesitation.  I certainly understand the fear... that you tell someone you're working on something and the one competitor that could ever possibly do what you're doing turns around and releases your idea and puts all of its weight behind it--all before you could even hire your first developer.

But that's paranoia.  Reality tells us that startups, for the most part, move faster and can focus better on particular problems.  That's why big companies buy startups--they know they can't really build things internally and get it right, let alone on time and under budget. 

On top of that, by not being public about what you're up to, you lose the opportunity for feedback and collaboration.  Perhaps someone out there has already tried what you are thinking of and has some tips.  Or, they bring with them a completely complimentary skills set and could be a potential partner.  You never know until you start talking it up.

Plus, I'm convinced that, to be successful, you really need to immerse yourself in the community you're trying to serve.  If you want to do a healthcare services startup, you need to be in the healthcare community talking with doctors, patients, etc.  Tell then what your ideas are.  Get feedback.  Get new ideas.  Entrepreneurs who work in well protected  bubbles (echo chambers) do not succeed... do not generate momentum...  their ideas die on the vine.

Still, its scary just putting it out there.

With all that being said, I'm going to start a conversation here--a conversation about an area that I'm exploring.  Yes, to do a startup.  Its funny because I always said I'd never do one.  I also used to say I'd never work at a VC, too, and also had no interest in working for a portfolio company.  Thankfully, I've also said many times that I also have no interest in being really rich, too, so I should be set there. 

So what is it?  What's the space?  Partners?  Funding?  Etc.  Patience, grasshopper.  There's a lot to do and a lot to talk about and there will be no shortage of coverage on this blog.