Our next shot is a product called OpportunityInbox and it’s essentially twitter for opportunities.
We invite about 20 people to try it, but most just don’t have anything to post. One of the funded TechStars teams posts a developer job listing. He has just two followers on the service.
I saw politely “Ummm, Eli, you realize that two people will see this posting, right?  It’s not craigslist. We haven’t build the audience for you…you have to go and do that”  ”Oh, hmm” and then tweeted it.

It’s quickly becoming clear that a ‘twitter for opportunities’ is not compelling. Are we really going to build a whole other service and ask users to port their entire social graphs to it JUST for the once-a-year when they need to ask for an apartment/roommate/job/employee?  People already have hundreds of followers on twitter. It just doesn’t seem like they’d rebuild their followers on yet another service.


But if people aren’t going to do that (bring their friends onto our network), how would the service grow?

Finally it’s back to our original model: the craigs and janelles will add all their friends and they’ll define the audience for everyone that’s part of the group. We’ll call it friendslist, a build your own Craigslist.

Ok, well if people have their own craigslist, who can post to it? The idea that your “list” is a place where other people can post and write seemed crazy to some people: “it should be like my tumblr where only I can curate it.  And I should be able to make it private.” Somehow this leads to week long discussions of different read/write settings a la -rwxr-xr-x

One mentor says “but if you rebuild 1000 Janelle’s lists, you’ve just rebuild Craigslist”  –  ”YES” I say!  – “But that sucks because everything has equal weight/attention. Isn’t that the problem with Craigslist? The good gets lost among the bad?” Hmm, he’s got a point.

Suddenly the conversations all become about the ‘public’ versus ‘private’ nature of opportunities. If I know of an available position at a startup, is that public or private? How about if I know my friend bob is looking for a roommate? What % of opportunities are private and could never be shared publicly, but instead must only be seen by a select group of people. Most resumes that arrive in the inboxes of these “middlemen” are private opportunities. Similarly a lot of startup positions get filled before any kind of public job post is written. Even the opportunity to take over a great lease on an apartment should be private, because otherwise you’re telling the world how much you paid.

The problem with Wegslist therefore, is if I’m running the group then I’ve defined the audience FOR you. Rather than letting you define the audience for the opportunities. Which means I’m only going to share bottom of the barrel opportunities that are fit for consumption by all.

If this sounds like a mess, that’s because it was.


Time has flown by. Demo day is coming up rapidly and we’ve over-thought and over-discussed the heck out of the problem yet built very little. I’m pretty sure we re-invented email, meetup, tinyletter, yahoo groups, and about a hundred other communication platforms — all in our heads…all in the course of a few weeks.

In preparation for demo day we throw together a quick landing page. I get on stage and pitch the original product vision: “we give well-connected people the tools to help them be more helpful. It’s just like Craigslist itself — the guy Craig tried to help his friends. That product worked once…why wouldn’t it work again?  And we do it all on a unified platform which lets us get to a massive scale.  We empower an army of users and when it gets to scale, we’ve build a Craigslist killer.”

We mock up the product:

step 1: “name your list”.

step 2:  ”invite your 942 friends.”

[continued from chapter 6]

My phone rings and before I even answer, I know. It’s my roommate letting me know that he’s moving in with his girlfriend and i’ll need to find a new roommate. Great, just the distraction I need as we go through Techstars.

I really don’t want to interview a bunch of creeps off Craigslist to be my new roommate. A Techstars mentor asks how we’d solve this problem if craigslist didn’t exist. ”I’d post it somewhere and tweet it and ask people to please retweet it.”  ”Ok guys, stop overthinking this stuff and just build that. Get it done as fast as possible

So we build http://plzrt.it/ (ie PlZ RT it= Please Retweet It. Yes, that’s an italian domain name)

As we present PLZRT.IT to the Techstars teams, Jason Baptiste shouts “Pleasure tit!” We still joke about that name years later.

The basic idea of Pleasure Tit, err PlzRT, was to separate Craigslist into its two halves, the CMS and the distribution network. We created our own simple CMS to host your description and photos. And you would use your twitter network as the distribution.  Later we planned to overlay a separate follower model on top of the site.

I post my roommate search on plzrt.it and it gets a few retweets, but no real leads.  A mentor posts an old TV and a Drobo and has even less success. Nobody is impressed. There’s no spark and no magic.

Even if it had succeeded, there was one big problem we saw. PlzRT doesn’t solve an actual search problem, it just rebroadcasts everything to everyone which doesn’t scale very well. “If this product becomes widely used, you’ll very quickly have noise decay” points out Brad Feld.

A few days later Gary Vaynerchuk (another techstars mentor) uses PlzRT to distribute a poll or something. We’re not really sure why. But because of his following it gets 50 retweets. And then Twitter emails us to let us know we’ve been banned for an API violation (i believe related to the “RT request” inherent in the service name). It’s the final nail in the coffin for PlzRT and we pull the plug on the experiment.

[continued from chapter 5]

She nailed it. Our product offering was vague and had been massively diluted by our attempt to satisfy everyone.

“Let’s start here,” Nicole suggested, “what do you and Benny like to do on the weekends?”  ”We bike a lot”  ”Ok, so start by building a bike-parts marketplace.”

It was a perfectly reasonable suggestion. Yet it felt incredibly unambitious and uninteresting. “How is that supposed to conquer the world?” we were both asking ourselves.

We desperately needed a break and to get out of our own heads. That weekend was Foursquare’s first ever hackathon (hint: foreshadowing). We took our first day off from working on Friendslist in over two months.

The night before, at Lolita in the Lower East Side, Benny and I had settled on building a foursquare app that replays your checkins from a year prior.  It would be a “mario-kart ghost for the real world” — you’d become friends with a second foursquare account (aka “Jonathan’s Ghost”) and you’d watch as your ghost checked in across the city. At lunchtime you’d see your ghost checking in for lunch a year ago that same time. At dinnertime, you’d see dinnertime checkins. And perhaps once in a while your ghost would be where you were!

“What’s that saying ‘Four score and something something ago?’” I asked Benny. “Four Score and Seven Years Ago — it’s from Abe Lincoln’s Gettysburg address.”  ”Oh right! So let’s call it Four SQUARE and Seven Years.”
Benny and I had a blast the next day. With some remote help from Designer Matt Raoul (too hungover to make it to the hackathon in person) we quickly pulled together a first version in under 8 hours work. We even dreamt up an Abe Lincoln themed foursquare mascot.
“Well that was fun!” we said walking home that night…what an awesome little product we had just invented — wouldn’t it be great if we could just work on that? Ah, but 4SquareAnd7YearsAgo is just…a hill. Not a mountain. It was merely a fun little project but hardly ambitious enough. Or so we thought at the time.
“We need to climb a mountain” we both agreed. And the mountain we had firmly set our sights on was Friendslist.

I’ve got exciting news to share. We’ve closed a seed round of investment to build Timehop into the ultimate digital history experience. 

You may already know (and love) timehop, a simple but deeply powerful daily email answering the question “what did you do this day last year?”

In a world focused on real time, we believe there’s an untapped opportunity in the past. We’re building timehop into the best way of recording, remembering, and reconnecting around our digital histories. The data exhaust of today’s services can tell your life story, but so far this data remains disaggregated and silo’d across devices and services. Timehop is a powerful product that brings together all your content into a single re-experience moment.

Timehop started as 4SquareAnd7YearsAgo, a fun hack that Benny and I built at foursquare’s first ever hackathon back in February. For several months, the product was on autopilot as Benny and I went through Techstars focused on our core product, Friendslist. But each morning I’d wake up and check the tweets and emails about 4SquareAnd7YearsAgo and curse myself at the money we were paying to send all the emails with no end in sight. Eventually, we started to realize there was something “big” in this “small” product.  Long before the internet existed, people have kept diaries and taken photographs. They do this to document their lives and acknowledge the passing of time. Timehop taps into that same powerful deeply human desire for self-documentation and the resulting nostalgia.

I’ll give more of the backstory of how this all came together at a later time, but for now let me just say how happy I am to be working with two of the best tech startup investors: Bryce Roberts from OATV and Andrew Parker from Spark Capital.

These two firms complement each other perefectly. OATV’s focus on data and self tracking is exemplified by its investments in Foursquare, RunKeeper, bitly and chartbeat. And Spark’s focus on content is exemplified by its investments in Twitter, Tumblr, and Foursquare.  Timehop is about both: content and data.

Bryce and Andrew are each amazing in their own ways. Bryce is super smart (and all that other good stuff) but what I truly love about Bryce is this: he’s a person first and an investor second. That’s a rarity and I sleep well knowing he’ll be by our side through thick and thin. Last but not least, Andrew is a razor sharp product thinker with a rare mix of academic intelligence and human intelligence. He’s truly a pleasure to work with.

We also have an incredible collection of angel investors: Dennis CrowleyNaveen SelvaduraiAlex RainertSteve MartocciJared HechtRick Webb and Kevin Slavin.

I could write a novel about each of these guys and why they’re awesome. But for now I’ll leave it at this:  I couldn’t be more psyched about the amazing group of people backing us and the exciting opportunity that lies ahead.

Right now we have a small team of hotshots: Benny Wong (our CTO) came from Gilt Groupe where he single-handedly build the entire Gilt City product and then built the engineering team around it too. He’s a true Ruby on Rails master. Rachel Nash (our lead designer) came from The Barbarian Group and before that Big Spaceship. And then there’s me (handling business/press/product/taking out the trash etc) who was formerly doing product management for a bunch of awesome startups and launching awesome subway apps. 

With this funding, we’re looking to add two or three engineers to our team. If you’ve ever wanted to join a small and passionate team building a product that people love, let’s talk. Digital history hasn’t been done right and we’re the team to do it. We’ve got a knack for making awesome products, backing from all the right investors, and a giant opportunity in front of us: a chance to define an entirely new product category.  Let’s blow this out of the water. Get in touch:  jwegener@gmail.com

[continued from chapter 4]

A recap: We came into Techstars convinced that our MVP (minimal viable product) was just a rebuild of Facebook Groups with the right messaging/landing page on top to fit the classifieds use case.

If Janelle’s List worked once, all we had to do was find a thousand “Janelles” to host lists on our platform and we’d quickly get to massive scale. The most beautiful part it that (in theory) it’d be viral! Connector-type people who want to play Craig would sign up and invite hundreds of friends into their list. “Why?!” people ask us. “Ego, pride, wanting to play God, wanting to help their friends, wanting to be a big deal”

It quickly became clear this wasn’t going to be easy. Nobody identifies themselves as a “connector” and few people want to do the heavy lifting of running their own marketplace. So, back to the drawing board…What are we building? And what are we trying to accomplish?

Several folks identify with the pain of playing middleman. We hear the same thing over and over “I get so many inbound opportunities and emails for people…i’m constantly playing middleman, I’d love a tool to help me with that”

Which brings us to chapter five.  We start sketching out that tool — a tool to help middleman better connect their friends and solve crowded inbox syndrome.

Maybe we build the “tripit for opportunities” — you forward things to an email address and they sit on your “shelf” where you can figure out what to do with them next. Of course this means we’re building a workflow enhancement tool, which isn’t really exciting. And it sounds clunky — is the medicine better than the disease?

One mentor wants a tool that lets him send opportunities to his portfolio companies. Right now, he’s created his own hack: he uses yahoo groups to send around resumes to groups of people.  Friendslist should be the “platform for sharing opportunities” => well that sounds compelling!  If foursquare is a vertical social network for location, and foodspotting is that for food photos, and plancast is that for plans, then our site is for opportunities!  ”I don’t know how it’s a business, but I’d use the product” the mentor says.

Another mentor wants us to automatically figure out who to forward inbound opportunities to (automatic friend groups). If he has to do any work or go to another place to manage these things in his inbox, that’s a deal breaker.

Yet another mentor wants to define his audiences carefully when sharing opportunities — essentially google circles. And another mentor wants to opt-in to hearing about certain people’s opportunities (a la twitter follow), not have information thrust at him like email today…how the heck could that work?  A double opt-in follow model?!

How were we going to build this ultimate product if we couldn’t satisfy everyone…

Somewhere along the way one of the investor mentors gets really excited too: “This is BIG guys..this is the opportunity graph.”  We spend hours discussing whether the headline for the site should be “We help you share great opportunities” or “We help you find great opportunities.”

The subtlety was completely absurd in retrospect. But we were way too far down the rabbit hole to see that.

Weeks flew by and we were no closer to releasing a product or having a solution we were confident in. Eventually we meet with Nicole Giaros, who runs the adminstrative side of Techstars out of Boulder. It’s one of our most important meetings because she’s a “normal” (ie not an early adopter tech type). So she’ll certainly have a good perspective on all this we thought.

Nicole listens intently as we explain everything. And then she says the smartest thing we had heard in weeks: ”It sounds to me like you’re making a something for somebody to do something.” 

[continue to chapter 6]