"Our architecture is also based on a reliable template - lightweight caching reverse proxys in front, proxying to the heavier app servers, which in turn are driven by the databases. We will aim for a shared-nothing architecture - decouple everything, push the state out to the client, compress, minify, and cache the static content, eventually pushing it out to a CDN."

I'm sitting in the MIT VC Conference right now, listening to Diane Greene of VMWare, thinking about the conference, presenting last night, and the Boston scene.

First off, the showcase was really great.  I should have blogged it here, but if you were following my Twitter messages, you heard that I livecasted the booth using UStream.tv.   I have to say, I was really amazed at UStream.  I plugged my camera in (first without drivers, which was my bad) and then the Flash linked up with my camera.   One click and I was broadcasting live to the web.  The coolest part was that I could embed the video player and the chat box anywhere I wanted. 

I'd never really checked out any of the Justin.tv stuff or Chris Pirillo's chats, but I got excited about this.  We may employ some of this at Path 101 to further open up our anti-stealth. 

Anyway... getting back to the conference itself.  People had told me that there really aren't that many "community" events in Boston, and that, which Boston has the VC money, the big institutions like MIT, that the community stuff is a bit lacking.  While I met a lot of great people here last night, I was really surprised there wasn't even more people.  I think of it as the equivalent to the ITP show and that gets packed every year.  In fact, there seems to be more people at the actual conference today, which you had to pay to get in.  How come?  Certainly it wasn't the fault of the organizers.  They picked a great spot and people knew about the conference.  Why weren't more entrepreneurs and VCs at the Showcase?  Students?  Or just people from the community?  I feel like it's the kind of thing more people should have been at...  like some swarm from a usergroup or something.  There were a lot of great companies there.  If anyone is involved with any great Boston-area tech community groups, let me know!  I'll repost them!

When I first got there, I have to admit, I was a bit intimidated.  I'm afraid my arts and crafts skills aren't what they used to be when I was in kindergarten, and I miscaculated the size of the boards compared to the size of my printouts.  I printed out twice as many slides about what we did and who we were and they didn't make the board.

Plus, other people had much more impressive displays.... clearly, they spent a lot more money at Kinko's than I did.  I was sort of afraid that I wasn't quite ready for primetime, but once things got going, it was really great.  People were really excited about what we were doing, and I got to meet some people in person that I'd only known virtually, like Alexa DuPont and Hilary Mason.

There were some visitors from companies in the employment space who we might be able to work with in the future, too. 

Most importantly, though...  were the conversations with students.  I had some great conversations with MBA students from interesting backgrounds trying to figure out what they wanted to do who really took the concept.

So what did we show anyway?  Well, we're in development right now and right in the middle of working on design.  I didn't really want to have our contract UX person spend resources on demoware that wouldn't move us forward, so I spent some late nights recently pushing my poor graphic design skills to the limit to come up with screenshots.  So, if you promise not to poke too much fun, and pay more attention to what's going on in these pages than the fonts, colors, placement, clutter, you can see the screenshots here on the Path 101 blog here.

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I've been trying to come up with an over presentation that I could just leave on the Path 101 site and forget about--so people who randomly stumbled in could get a better sense of what we were up to.   I tried Google Docs, but I really wasn't happy that I couldn't do some kind of animation and walkthrough.  Then again, I really don't like adding my voice to these things, even though people seem to like it.  So I created an animated presentation on Powerpoint, and used Jing (along with its 5 min limit), to capture it.  It exports a Flash SWF, which is now sitting on screencast. I have a few issues with the result, but I don't think it's that bad.

1. It might be a little too fast.  I'm not sure, because I've seen the presentation a million times.  I prob should have combined the team slides into one and I'm sure there's one other slide I can can.
2. I really, really wanted to embed it smaller somewhere on the site.  I can't for the life of me figure out how to make the Flash smaller.  I can make the embed smaller, that's easy, but to squeeze the actual Flash into a smaller embed... no idea.  Here's what I wound up with... any suggestions?  Converting to video would have solved that, but I couldn't find a good conversion tool that converted at a good resolution.   UPDATE:  I used Slideshare at the suggestion of others and it came out MUCH BETTER!!  
3. If I convert it to video, perhaps I'll give in and add a voice track... but it takes a long time to speak through..  and I want to keep it at 5. 

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Tags: path101, presentations, flash, ppt

Perhaps I'm being too defensive here, but I can't help but feel the need to respond to a recent post I sawon InsideChatter.   I first came upon InsideChatter when Donna ripped on Nick O'Neill's post on LinkedIn vs. Facebook.

Aren't most blogs indistinguishable and unreliable?  I mean, I guess mine's pretty special because I like kayaking (j/k) but other than that, it's no better or worse than anything else out there.   There aren't very many great blogs out there, except maybe danah, Scott Adams, or Marc Andreessen.  Eric's and Fred's blogs are pretty good, too...  but I'd be careful saying that other people's blogs are indistinguishable.  I think we're all lucky to have any readers at all, but I digress.

What she failed to see was that amid all the Facebook ra-ra! from Nick, which I actually disagreed with, because I do think there's a point to a network for each of my different selves, was a really good point...   If Facebook can present several faces of you to different people, then it's a real challenge to any social network out there, not just LinkedIn.  Dismissing that point out of hand may prove to be the death knell for many networks. 

Today, she wrote about Path 101, which is to be expected of course.  I mean, come on, did we honestly expect we wouldn't get negative feedback to putting ourselves out there so early?  I would have written a response in the comments to her post about us, but she doesn't allow comments.

First, Donna did a nice job of catching my slip up in saying that it was "top 10" within the post.  Nice job.. I started out with ten, but didn't really feel like all ten were strong, so I shed a few, and forgot to re-edit.  I fixed that.  Thanks!

I think if you check the overview, you'll see that there isn't much of our business that has anything to do with LinkedIn.  All we were trying to do is not add in features that already exist elsewhere and cause users to sign up for yet another social network.    Connecting professionals isn't our business.  That's theirs.  We just figured it makes sense to be discovering careers and connecting to professionals in an integrated way, that's all...a nice feature.  If we just have to create links to say, "Go here and create a LinkedIn account while you're discovering careers on our site, you'll thank us for it", we'll do that, but it seems silly. 

Path 101 on its “status,” as of October 11: “NO assets, NO revenues, a two day old empty checking account…and now, back to actually building this service.”"

Just to update, we'll have money in our checking account by the end of the week, from Fred Wilson (who leaked his own involvement before we were even ready!) and others.  As for what else we can do today, that's not what this post was about, mostly because the LinkedIn API isn't ready today either.  If we're building the service TODAY, does it make sense to speak up when we're done, or when we actually have time to integrate with their proposed API based on our proposed vision?  This is something that happens in the startup world all the time.  Someone plans on building something and they talk to others in the same space to get a sense of how they could work together in the future.  It's pretty commonplace.

This post also seems to imply that if you're friends or family with someone, they don't belong in your LinkedIn network.

Yo, did you say my family is not professional??  Oh, snap!  :)   Actually, I got my first job in the Waterhouse Securities mailroom through my older (by 17 years) brother, who was their Regional Vice President of the whole 30+ office Midwest branch at the time... and his network would probably be highly accretive to LinkedIn.  Perhaps if there was an easier way for his techie little brother to show him the ropes on it, they'd benefit. 

But you're the expert on LinkedIn, right?  You and your.. um...wait... 14 connections???   Are you serious?  I was assuming I'd get ripped apart by someone who is even a more passionate user of the service than I am.  (See my "Getting Started with LinkedIn" post.)  Don't get me wrong, I love a good back and forth about what that service needs or doesn't need, but I was assuming it would come from someone who uses it a little more.

Ok, so maybe it was better off that there are no comments on InsideChatter, because I had more to say and it wouldn't have fit. 

We did get some good positive comments, too.  Its nice to know that others seem to be behind what we're doing:

Comments from Fred's post

Comments on our post

Thanks to all who've been really supportive and even those who haven't!  I'll definitely be adding Donna's blog to my blogroll to get her feedback in the future...  because just listening to praise is never a good idea.

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Tags: linkedinpath101

More uber anti-stealth...

....by myself.  Check out our fun legal signing pics on the Path 101 Blog.

Two bits of anti-stealth today... now that we're out of our apartments for the first full week and living within the friendly confines of Return Path, we're feeling pretty psyched about our ideas.  We'd love to share them with you, and so we're holding an open product feedback and brainstorming session this Thursday night at CRESA's offices in midtown.   It will take place at 6:30 and probably run until 8:30.  Details and link to RSVP here.

Also, we diced to open up our Monday morning meeting notes to the public, so you can further track our profess.    You can see how we're diving up the work, our progress, etc.

A lot of people think starting your own company is a risky proposition.  Sounds like it, right?  Oooh...  could "blow up".  Sounds dangerous.  Images of shrapnel.

Maybe I'm naive and oblivious... but I'm really not that worried, like, at all.

I'm working on Path 101 fulltime and the only income I get now is from my adjunct teaching at Fordham, which is sort of like my checking account's equivalent of flapping its arms as it falls off a cliff.  Yet, somehow, I know it's all going to work out.  I'm confident we'll get our angel round raised... people are lining up now...  but on the chance we don't get all of it, we'll make do with what we have.  We'll take on some consulting if we have to.  It's not ideal, but there's a fallback plan, and frankly, the fallback plans aren't so bad.

Maybe I'll need to start liquidating to fund this.  I already know...  first it's the 401k, than the apartment, and then the car.  Yes, the car is the last to go.  Not ideal, but at least I've faced the reality of the situation.  I can deal with it.

And if this whole thing doesn't work out... if we can't get something compelling built or can't grow the user base or can't monetize, and we have to close up shop.  Then what?  I'll be upset, no doubt, and disappointed, but...   I'll survive to die another day.  I'll just get a job somewhere.  I believe I'm employable and have no fear that I'll wind up homeless on the street.

So what's really the big risk?  I mean, even in the worst case scenario, I'll learn something...  I'll learn a lot, actually.  It will build character and I'll meet a lot of great people along the way...  and build a great relationship with Alex, too (or kill each other... either way). 

Frankly, if you think about what I could gain or lose by taking this on vs. not taking it on, I think I've got a hell of a lot more to lose by not doing it.

I got two comments on my previous post about some creative ways to get some elements of my startup done (some quick and dirty ways to get a logo) that I'd like to address.

First, Nate's comments...

"Don't settle on a logo early and don't let someone outside the company do it. Yes, you need a better one -- and fairly soon ;-) but don't lock yourself in and don't lock your eventual full-time designer out of the process."

I like this angle.  It makes sense to me that a designer, especially one that we'd like to hire full time, might not want to get handed a logo that may or may not square with their vision for the look and feel.  That's an excellent point.

Now, Rachel's comments.  I don't know who Rachel is, but she seems to be (or believe herself to be, given her tone) an expert in something...

"Corporate identity (logo design/graphic look and feel) is brand expression, which is the derivative of brand essence, which you haven't done any strategic work on..."

Personally, I don't believe that seed stage startups should do "strategic work" on corporate identity.  They should build a useful product, period.  So many times, web services do fancy redesigns to make things look good when they flat out fail on improving the usability of the product.  "Brand essence" = good product.  You think people use Apple because they like the logo?  No, it's because their products are functional and easy to use.  All the brand positioning in the world won't save a product if it doesn't just flat out provide utility.  Do you think Craigslist does strategic work on its brand essence?  Having met Craig, I'd say I highly doubt it.  I mean, hell, they don't even have a logo.

Actually, they do.  Here it is:

Craigslist

Snarky?  Yeah, because I'm just snarking back to her comment about my presentation:

"It's a mess from a sheer presentation standpoint. Clean it up, format it, get those headlines right, just get some look of discipline in there and the VCs might overlook your age and inexperience"

It may be a graphical mess... I don't pertain to be any kind of expert, but it is also on Google Docs, so things got bumped around a little.  In fact, that's the very "essence" of the company... open, out there, direct...   but figuring as we're having little trouble attracting interested folks, perhaps other VC/angel pitches aren't messy enough.

But the real kicker is this:  "get some look of discipline in there and the VCs might overlook your age and inexperience".   

Rachel, how old do you think the average internet entrepreneur is that gets funded by VCs these days?  Certainly not a lot older than 28. 

And my inexperience?

So tell me, how many people are out there who have been a product manager during the launch of a new product, evaluated early stage startups for a top tier VC firm, taught both undergraduates and graduates in classes that they developed from scratch, ran a mentoring program for both a professional society and a school's alumni organization and also created a professional organization that currently has over 1,000 members?

Perhaps I haven't run an enterprise software product and taken revenues from zero to fifty million, or led three startups in completely unrelated spaces, but I dunno, from my vantage point, I couldn't imagine being any more fortunate that I have been to get the exact kind of insight and experience  needed to make Path 101 a success--plus not to mention the absolutely fantastic network of people I've built up to help me.

So, instead of trying to "grab the conversation by the emotional cojones" which is, trust me, what a lot of entrepreneurs try to do ("We're going to change the world, you'll see!") I'm more interested in solving a real problem with a useful product.  A lot of marketing "experts" think that it's all about "sexing up" the pitch.  I've been on the other side of the table (have you?) and trust me... sex doesn't sell in a good VC firm, nor does it sell a sophisticated angel investor.  A good idea backed by the appropriate passionate entrepreneur in a market ripe for disruption is what we're selling here and I'm quite confident we'll do just fine.

Alex and I threw an idea out there that might be ridiculous, or it might be pretty good.

As we're starting up this business, we'll be accumulating all sorts of little expenses here and there out of our own pockets until we raise this angel round.

For example, we need a logo.  I'm sure it will cost us a few hundred bucks at the end of the day.  I also want to make a trip up to Toronto because I have a connection to a big group of schools up there.  Same with Providence, RI.  Trips, obviously, cost money, but they're really valuable to drum up school support, get feedback, and get market knowledge about who else is out there.

Well, what if we could get someone to sponsor these expenses?  Would it be worth a law firm, professional services firm, IT consultant, or some collaborative software's money to slap their logo on some aspect of our process?  Maybe we'll decorate our company blogs with logos of other companies and say "Logo provided by generous sponsorship by Scion"  or something like that?

Is that ridiculous, or just a smart way to monetize the high profile we're fortunate enough to have with this startup?

Anyone want to sponsor our logo design, or contribute a logo design?

I think if someone wanted to do a logo for us, I'd do a video interview with them to put on our blog about the process of doing a logo for us and link to their portfolio.

Maybe we can get a lawyer cheap that way, too.  Interview all these professional services folks about how they want to work with us and advertise their services for payment in kind.  Hmm...

Path 101 is looking for a designer...  Alex and I need someone to help with evil laughs and cackles as we take our ideas and create mockups, clickware, and eventually, the site itself, as we yell, "It's alive!"

Alex and I are looking to grab some empty desks in NYC... got any?  Details here.

Alex and I have been doing a lot of meetings for Path 101 and one of the most difficult things has been adjusting the flow and content of the meeting for the audience.

So, for example, we took a meeting with a VC that we knew well and whose demeanor is usually pretty fun and casual (not Fred, just fyi).  So, we decided not to run through our slide deck and instead stayed at a high level, conceptual, throw some ideas about the space around, kind of thing...  conversation was kind of all over the place, admittedly, and today we got the "sorry, not for us" e-mail.  I'm not sure I would have invested in us either, because we probably seemed a lot more all over the place on product than we really are at this point.  It's unfortunate, b/c we really didn't feel like we put our best foot forward.... basically got fooled on a pitch and looked bad for it. 

Conversely, we tried to walk through the slide deck with another VC and it was 45 minutes before we got past slide two and that conversation was excellent...  and it was our attempts at herding the cats back into the slide deck that actually made the conversation less interesting.   

Predicting what someone needs to see is incredibly difficult.  If you've ever pitched at USV, you know that you should just walk in and show them the product, throw some ideas around, etc...  It will become more like a hack-a-thon than a pitch meeting... and you need to be able to roll with that flow... b/c that's how they like to get to know businesses.  They want to poke and be imaginative about what you could become, who you run into... what is the scope of possibilities for this business and how flexible are you and your model.  Not all VCs are like this...and if you bet wrong, you might not get another meeting.  I like to think that we never held slide deck dependency against any entrepreneurs at USV, but it sure does make it difficult to get in an engaging conversation with someone.

What we've found incredibly useful has been meetings with other entrepreneurs... not for funding or biz dev, but just to see what others think, and also learn a lot about how partnerships and teams function.  We met with Paul and Rony from Indeed the other day.  They have an incredibly focused strategy and clear vision on what they want to be.  We're quite a bit wider and perhaps a little amorphous at this point and so it was an incredibly valuable conversation to have... not just to help us think about focus, but to help marketing our focus.  We know we'll be building something comprehensive, but we don't need to overwhelm the audience with the comprehensive vision before establishing the viability of the first thing we want to build. 

Yesterday, we met with Pete and Josh from Reprise Media (and got to meet the infamous Kate from Searchviews).   As we did with Paul and Rony, we tried to gain a little insight into their working style, which would be hard to match since they were childhood friends.  Still, hearing about the process of hiring, collaborating, product management from people who've done it successfully is invaluable.   Josh finished up our long diatribe on what we were doing with, "You need an elevator pitch", and Pete responded, "So do we."  That's our next step, in addition to all the product strategy work/research we're doing now...  culling the message down to its basic points and tailoring that to investors, schools, the public, etc.

Alex and I were talking about opening this whole company creation process up...  like doing some kind of a regular open meeting where people can just show up and essentially give feedback and here about our progress so far.  I don't know what the right venue for that would be... we'd certainly like to make it as casual as possible, but also somewhat functional.   Perhaps once we wrap up this funding, we can do it in our own tiny little cramped office.  In addition, we'll be adding a wiki to our site and a blog of course to further expose ourselves in public.  :)

Alex and I are heading up to Boston on Friday to meet up with some angel/VC types and want to spend the morning meeting with some college career planning offices.  If anyone has good contacts, particularly with schools like Boston College and Boston University, I'd greatly appreciate it if you could drop me a line--especially if you know them well because you've worked directly with them, spoke at one of their events, etc.

I was excited to see that Yahoo! thinks there's an opportunity in the college career space.  They're supposedly creating a new social network called Kickstart.  From the Path 101 perspective, I say, "Bring it."

Man, I can't wait to see this. 

So, when's the last time a big media giant created a really successful social platform from scratch?

[crickets]

It seems like we're not even sure if this is just vaporware, but even if it isn't, I'd say there are at least five things that Yahoo! is inevitably going to trip up on.

1. Hell hath no fury like a media company scorned by a social network.   They couldn't buy Facebook, so they decided to make their own.  But, they needed an angle.  What do college students what?  A social network about beer?  Nope... they're underage.  Sex?  No, can't do that, not that it wouldn't be successful.  Ah!  Jobs!  Yes, jobs!  It seems like Yahoo! is starting out with the idea that what they're building must be a social network, without really considering whether or not the social network approach makes the most sense.  This is just bad product development.  You don't walk into a problem and say, "Whatever the opportunity is in this space, we're going to solve it with a social network... and a hammer."  I actually tend to think that social connecting/friending isn't what students really need... it's content, direction, guidance, tools...  Just connecting is like handing students a business card.  They don't have any clue what to do with that connection and how to get the most of it, let alone even know who to connect with in the first place.
2. Play well with others?  Ha!  Let's see...  34 million Facebook users.  14 million LinkedIn users.  Let's build our own thing and not plug in to the vast networks of existing students and professionals already out there and start completely from scratch because we want to own this category.  If you can't bridge the gap to your customers by meeting them in the places they already are, then don't expect them to come to you.
3. It's going to be all about jobs and companies.  Yahoo! knows how to sell stuff, like jobs and ads.  So, they're going to build something that is going to be immediately monetizable, meaning its going to be all about companies, jobs, etc.  There are two problems with that.  What about companies that aren't on there?  What if I don't want to work for some big corporation that can afford to pay Yahoo! to have a presence on Kickstart?  Is this going to be a place where art students are going to find jobs?  What about drama majors and people looking to work in the non-profit fields?  Doctors?  What about grad school?  Or, most importantly, what if I don't have a clue what I want to be?  What then?  Am I likely to join a social network based around job recruiting if I'm "undecided"?  I highly doubt you'll see any freshmen or sophomores on this site because they haven't chosen a field of interest yet and probably aren't sure where to go.  That's the real problem that needs solving... helping them figure out where they want to direct themselves, not connecting kids who already know what company they want to work for (which is how many of them anyway?)  Here's the other thing.  Because of their HotJobs affiliation, is Yahoo! ever going to tell a student that the best way to get a job is through networking?  What they're doing isn't real networking.  It's putting a social network around a job posting.  There's no way Yahoo! will eat its own lunch and totally disrupt the jobs space.  They'll find a way to perpetuate the old business model of charging for posted jobs at a few hundred bucks a pop.  In a pure socially networked world, there wouldn't be that kind of opportunity to extract so much value, because the right opportunities would fall into the right laps all the time in a seemless, barrierless way.
4. Professionals: Sign up and get spammed by students desperate for jobs. If I'm a professional working at a company, exactly what is my motivation to sign up for a social network based around getting college kids jobs?  If I put a profile up and people can contact me, aren't I opening myself up to just getting spammed with resumes?  The service has to work for everyone involved and if all these college kids can only find their way to a company by connecting to someone who works there, the last thing I'd want to be is the first Google employee who puts a profile up--especially since the atmosphere here is all about jobs.  Professionals love giving advice and helping students away from the recruiting process and such relationships are best built over time.  If the whole thing is just focused on jobs, its going to have the feel of one of those really bad "networking mixers".
5. Their customer is the company.  One of the advantage that startups have over bigger companies is that they can spend a little time purely focused on value to the end user first before figuring out who their customers are.  Take Indeed.  Indeed could never have gone to job boards day one and said, "We'll crawl all of you, and then you pay us to sponsor your listings and get them to appear in the sidebar results."  However, after they proved to be a very compelling consumer service with growing traction, job boards realized the value, especially the smaller ones, and got on board with what they were doing.  When you are a big media company, you don't exactly take risks with your clients, but where that leaves you is lacking in the end user value.  I mean, would YouTube have become so big if they didn't start out with all sorts of illegal clips?  Students want real insider content...  and real discussion.  Do you think any of these students are going to get into a discussion on the Nike page of whether or not they'd actually like to work for Nike given their history of human rights violations?  Have they cleaned up their act?  Is this a place I want to work?  I wouldn't ask with the recruiter sitting right there in my network, that's for sure.

Look, Alex and I haven't built anything yet and the proof is in the pudding, but seeing these kinds of attempts just gives me that much more confidence that we have the right approach with Path 101 and will succeed.  I've been in the classroom with students talking with them not as a corporate focus group, but as a teacher, mentor, recruiter, etc...   not asking them, "Hey, if we built this, would you sign up for it" but discussing their real struggles.  They don't know where to start and this isn't it.  Not only do they not have a network, but they don't know what to do with a network once they have it.  They don't know how to e-mail a professional.  The services that are out there don't attempt to tackle the hardest but most compelling problem in the career development space...  how to get students figuring out for themselves where they belong and pursuing those paths.  Just throwing a bunch of jobs and companies at them is window dressing and not going to really help them figure much out.  If anything, it just perpetuates the problem that most students think their only options are to become bankers and lawyers or work for big companies, because that's who they see recruiting.  Path 101 will get them talking, exploring, using tools, very much the same way TheKnot.com not only helps you find flowers for your wedding, but helps you actually think about what kind of a wedding it is you want to have in the first place.  After that, flowers are the easy part.

Looking for a partner is different than looking for just a developer, and it's a difference that was particularly important to me.  To build Path 101, I could have just scraped some angel money together, done some consulting, and pulled a spec out of my own personal echo chamber and put something out there.  But, that wouldn't have been as good as something that was vetted by someone who had a stake in the outcome--whose interest and ownership in the project inspired a true sounding board, real feedback, and new ideas.

But where to find someone in this market?  On one hand, it felt like everyone who had the technical capability to be out there building something was doing just that--and working on really interesting things.  On the other hand, this new wave of innovation had been going on long enough that there were probably a few early projects that were impressive but just didn't seem to make it to the next level.  I figured there had to be a few talented folks who may be ready for their second Web 2.0 tour of duty.

When I was at Union Square Ventures, we looked at ATTAP, the builders of Riffs, PersonalDNA and Life I/O.  I used to joke and call it the "techie commune".  It was a bunch of really impressive, cutting edge tech folks working on some very ambitious personal information management and recommendation products--all located in half of WebCal founder Bruce Spector's apartment.  The first time I met Alex Lines, he was a lead developer there and he showed us how he had hacked together a mobile geolocation system based on cellphone tower data.  It enabled a cellphone to know where it was in the city long before phones had GPS built into them.  He had hacked an exposed mobile API and did some tower wardriving throughout the city. 

ATTAP alumni was one of the first groups I went looking for to find potential partners.  Even though the company might not have reached the success they were looking for, I was always impressed by the people they had and their ability to flat out build really elegant stuff.   

I met him again earlier this summer at a nextNY event--after he had left ATTAP and I was anticipating leaving Oddcast.   I didn't know I would be working on Path 101, so our ships passed a second time in the night.  But, after scoping out some team pages, asking around, and cross referencing a nextNY softball RSVP by "a. lines", I zeroed on on Alex, who, as it turned out, had already read the original Path 101 post on my blog with some interest.

So we met up and realized that we saw eye to eye on the project from the start.  What was important to me was that we had the same approach to partnership--mutual respect for experience and each other's opinions, open communication, and a goal-oriented approach.  This was not a guy I was going to get bogged down in personal issues with, nor someone who thought he knew everything or thought I did either.  I also liked his approach to technology--focusing on  functionality and relevance to the user--above loyalty to "web 2.0 trends".  Alex met with a former colleague of mine and the feedback really summed it up nicely:

"...he is a technologist, and not predisposed to any programming language or framework. Find the best technology to solve the problem. Big plus. "

His technical capabilities extend to perl, ruby, php, c, c++, sql, korn, bourne, javascript, html, Oracle, Sybase, MySQL, FreeBSD, Solaris, Linux, OpenBSD, Mac OS X, and, as we learned last Friday, softball bats.

He's also a bit of a Renaissance Man.  At Vanderbilt, he was a Physics and English double major. 

Plus, he's also a Brooklynite (Park Slope), so how could I go wrong? 

I'm excited to be working with Alex and we're currently busy laying out our vision of Path 101, meeting with potential angels, and other stakeholders like career offices and professional societies.

We're also looking for a great front-end designer/developer to join our team, so if you know anyone, please do send them our way.  This train is leaving the station!

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.   

Thanks to all of the folks who have given early feedback on Path101.

Here's what people are saying so far:

First off, no one has bashed the name yet.  Personally, I don't like it at all, but I'll admit, it's not awful.  It seems like that's what a name has to be these days: not awful and at a dot com.  Then, you can focus on having the product create the brand image, not the nomenclature.

The response most often given was, "Why limit this to just college students?"  People pointed out the huge opportunity for career changers, moms reentering the workforce, and adults later in life.  I absolutely agree that such a platform has more legs than just in the college market.  I just think it's good to start somewhere and the college market certainly isn't a small one by far.  Plus, that's the market I know.  I don't know what it's like to get laid off at 50 or reenter the workforce after having kids, but certainly that's an opportunity for growth.

Others said that I was building something for students just like me, and that most students didnt know what they wanted to do even when they graduated.  Because I agree with the second point is exactly why the first isn't true at all.  Particularly because most students don't know where to start and haven't done much career prep is exactly why this platform is valuable.  Just because they're not doing the work now doesn't mean they don't want to get into an exciting career.  Most students don't realize that they can take their passions and make a greate career out of them.  Take my friend Christina.  She must send out a party evite every week and most of them aren't even for her-she's the consummate organizer and she's been stuck working with kids in a job she's not a big fan of for the past three years.  Finally, she came to me the other day and told me she was switching careers and becoming an event planner.  DUH!  In college, she probably never realized how huge the conference and event planning sector was.  That's the opportunity...to take her pre-existing interest in organizing people socially and give her an opportunity to connect with the people, content, groups and events necessarily to fuel and focus that interest.  If you do it socially, you don't even need to be particullarly introspective.  Your friends will tell you something on the order of, "You're so great at party planning...you should do THAT for a living."

The big knock on students in their first two years of college is that they're not thinking about this stuff.  That's not true at all--they're thinking about it all the time and scared stiff by it.  Their parents and families keep them thinking about it, and they definitely think about it when it comes down to deciding what you're going to do with your summer.  Most students would love to pursue interest over the summer, but they just don't know where to start.  It's not like there are a lot of job ads out there for "freshmen with no experience."

The other piece of feedback I got, before I added the biz model page to the deck, was on how college students won't pay for this, and that's right, they won't.  That's why we're going after the deepest pockets in the ecosphere on this one... the recruiters, companies, advertisers, etc.  We will not charge colleges or students to use the service, unless of course that a college wants to advertise themselves... like for grad or continuing education programs.

Keep it rolling it... I'm off to setup our (my) Basecamp account.