Category: Technology

Getting to the bottom of the funnel

I have been interviewing a number of candidates for different roles within Foursquare which have resulted in some very interesting conversations.  One of the things I do at the end of every interview is leave time for folks to ask questions.  One of the most common questions I get is “why did you join foursquare?” (or some variation).  I have gotten into some great conversations around my answer and I thought it was worth writing about here.Funnel

To answer the question properly I walk folks through my previous roles and what motivated me to change jobs in the first place.

When I graduated from college I thought I wanted to work in advertising.  I got a job at Mediacom as a Media Planner, which means planning advertising for clients in areas such as TV, out of home, radio, print, and other mediums.  It was during this time that I actually started this blog (when it was all about Marketing).  I soon realized that this type of advertising was not really accountable for clients.  It was (and is?) thought to be effective by very hand wavy metrics such as “visibility” and “brand awareness” but it was impossible to really track.

I realized that interactive advertising and banner ads provided great accountability and metrics you could really dig into.  Around this time I made the switch to focus on a role that allowed me to work on many more clients instead of just one (those at Mediacom and Beyond Interactive) looking for interactive ads that they could track and learn from.  I saw this as a great answer to the great unknown of traditional ad effectiveness and much more reasonable to spend budgets against.

It was around this time that I became obsessed with ad stats, ROI, and metrics that could measure success for advertisers.

Some of the campaigns I worked on were traditional banners campaigns while others were more sophisticated sponsorships of the apps and programs of the day such as instant messaging clients, rollovers, and takeovers on sites.

In early 2006 I heard from an in house recruiter at a company called Reprise Media that worked specifically in Search Engine Marketing (SEM) which was a nascent advertising space dedicated to delivering targeted advertising solely based on someones intent.  Ding!

Once I groked what they actually did I jumped at the chance to meet with them.  It was amazing to see under the hood at a startup, and begin to understand the world of search advertising.

I saw SEM as being the so-called “holy grail” of advertising, only showing ads to those people that were actually looking for something similar!  If someone typed “running shoes” into a search engine, chances are they are looking for “running shoes”.  Therefore ads targeted around running, shoes, and combinations therein made for a great experience, perhaps even helped by the ads.  By virtue of an auction based system, quality scores, and actual click data search marketing seemed like the best way to reach someone who had real intent.  The marketers that got it early benefited from great results, an uncrowded space, and real metrics they could sink their teeth into and bring back to their CFO’s and claim success.  It was the first advertising medium I found that if effective, would result in unlimited budget from clients.  In a few cases we could beat the margins for products and arbitrage ads/traffic making clients a ton of revenue and profit in the process.

Fast forward 2+ years, after the company was sold to IPG, I was looking for what was next.  I soon found Union Square Ventures as a place to learn even more about startups, but from an entirely different viewpoint. (I will leave that experience to other posts)

When I met the founders from foursquare, and I heard what they were doing, I immediately became fixated on real world analytics.  A Foursquare merchant could actually see results in the form of real live foot traffic walking into their stores.  This time around there was a company that actually knew when you were in a “Running Shoe” store by the act of visiting that store.

It seemed I had actually found something that was further down the funnel than any other type of advertising I had ever seen.  People were checking in to places by the hundreds (at that time) and merchants were getting their first look at bridging the digital and physical world together.

I knew right away that what foursquare was working on was fascinating to me, appealing to my analytics side as well as my curiosity in figuring out how brick and mortar locations could innovate.

Over the past two years I have helped build up a massive group of interested merchants from around the world (over a million now!) that all use this dashboard information to speak to customers.

Its been an exciting journey and I hope to go into further detail about many of these experiences – but this is how I look at a decade of job progress since I graduated.




Nestio – Solving Renting

As anyone who has spent time living in New York will tell you, renting an apartment can be one of the most complicated, confusing, and mentally painful processes you can go through.  Thats why two years ago when I started working with the NY Tech Stars program as a mentor, I immediately connected with the Nestio team.  Led by their CEO, Caren Maio, they are building a better way to get correct data from landlords and owners to brokers and renters.  Today, they launched a new service to better help brokers and owners manage listings.  The graphic below describes their offering best; solving the problem of incorrect information that exists between landlords and brokers and the renters.

Screen Shot 2013-06-19 at 10.39.58 AM

Instead of relying on poor source data for listings, such as email blasts, faxes, outdated spreadsheets and the like – Nestio provides a way for owners to enter their information directly into the Nestio platform.  This in turn gets the right information into the hands of brokers, which can then rent to consumers faster.  The ecosystem improvements that Nestio are bringing to market are exactly what the Manhattan rental market needs.  Today, trying to find an apartment can lead you down many paths where is difficult to find out if a place is even available. is becoming the central database for all listing information, directly from the sources (owners!).

The best part about working with this team has been watching them execute.  Its one thing to say you are going to solve the NYC real estate markets problems, and quite another to deliver.  Over the past year I have watched Caren and co. systematically build up a huge database of owners, brokers, and renters creating the right ecosystem to thrive.  Now, owners are spreading the word about the time savings and headache avoidance Nestio is bringing them daily.

New York City represents the wild wild west of real estate and it has been a pleasure to watch Nestio tame it.


Wither the desktop client (Mozilla Thunderbird put on autopilot)

Mozilla announced that their messaging software Thunderbird will essentially be put on autopilot, shifting resources to other projects. Lots of sites weighing in (and people too) with commentary and even internal memos about the news.

This is bittersweet news for me as a user of Thunderbird for years when I was a Windows user.  It was far better than any other software at handling multiple pop3 email addresses at the same time.  I can remember a time when I setup my websites and going through the process of configuring email addresses online in a hosting control panel, followed by authenticating each email in Thunderbird.  For me, this was an important learning step in understanding POP3 and IMAP and the implications of each.  I thought I had it made when IMAP became supported and I was able to truly see messages across multiple Windows boxes all updates together in real time.

The writing was on the wall of course, as managing multiple email addresses across multiple computers could be made exponentially easier by having them all controlled via browser.  It was around this time that I discovered Google Apps For Your Domain (that was the orignal name!) and switched everything over.  Painful, but very worth it.

Now of course web based email is the norm (sorry Exchange users its true!) and everyone expects services to be available via browser.  Thus, the withering of desktop clients continue.  This is a bit unfair as there are a bunch of applications I still use on my desktop – but for the most part I look for a web solution first.

The biggest shift is that when looking for a solution, I am inclined to pick a web based product simply because the switching costs are lower and it makes hardware obsolete.  As with many things its not obvious at first, but over the past few years I have switched many of my primary use cases to browser based solutions.


hello Homeland and the #screwcable problem

I have been thinking about cable tv and the future of video for what seems like forever. Much has been written here about tv in general, boxee, and the future of television (remember Joost?).

Tonight I finished watching Homeland from Showtime – and tweeted about it (really great show by the way!)

To my surprise it set off a flurry of responses from friends and colleagues who were at various stages of being either interested in starting to watch it, in the middle of it, or interested in more.  This presents a “hello Homeland” situation for many of my friends who want to see the show from this tweet, heard about it elsewhere, or maybe just have an interest and want to sample it.  But right now they can’t do that.


Some friends even started watching it right away based on or tipped into watching it from my recommendation.

This is the part I find extremely fascinating (and no, I am not looking for a pat on the back).  Everyone is looking to cut their cable, and stop paying large cable co’s for service, or switch to an a la carte model.  The problem is that this does not mesh well with the behavior that we currently follow.  Its extremely hard to change peoples behavior, and although the complaints are real, the bills are high – the benefit of cable to solve this need/desire to consume things as they are broadcast is a real benefit.

This all got me thinking about Fred Wilson‘s #screwcable post in which he says:

I’ve long believed that piracy is largely a business model problem not a human behavior problem. If you give people a legal way to consume the content they want, they will pay for it.

So what business model supports the current behavior? Affiliate links and capturing attention.

Currently there are different models that could support this type of behavior.  The simplest is affiliate links.  More difficult is capturing attention.  If I could have linked out to two (or one if they were smart) types of content, I bet I could have generated direct sales, or possibly even subscription sales for Showtime via Homeland.  Afterwards, there is interest and intent around the show – just waiting to happen online.

Affiliate links

The first, and simplest method would be to allow someone to deeplink to content that only subscribers have access to.  Meaning a Showtime subscriber could link to an extended viewing of Homeland to their social network, attributing the longer viewing and following episode sale or subscription sale to their account.

The second, would be driving views to content (read: ratings) via my recommendation.  This attention could be monetized by ads, and because it comes from a trusted source (me) my friends and colleagues may sit through advertising supported video for their first viewing of the show.  Subsequent purchases and subscriptions would also be attributed to the original seeder (again me).

Capturing attention

This method has been tried for years by many startups.  I have personally seen many companies that have promised solutions, but never delivered.  A real time chat room or re-played chatroom next to video content isn’t what anyone is really looking for.  They want to share their thoughts about something when its over with their friends in real time.  This is today solved by Twitter and Facebook – usually in a hard to follow thread of comments.

The real time (somewhat solved by Twitter today) and post watch need for a watercooler is very prevalent.  Some friends even wanted to chat about it as soon as they were done watching.  Why can’t Showtime (or someone else for that matter) give us a place to have this conversation.  I am much less excited about this opportunity, but if it offsets the cost of all-you-can-eat cable and gets us to the a-la-carte model faster than so be it.

The problem with an immediate consumption based behavior means that only true a-la-carte cable pricing would suffice.  This would mean an ever growing firehose of video on demand, available at a clicks notice.  Since this is not going to happen anytime soon, this affiliate model would work quite well.

Based on the reactions of some of my various friends, its clear this would have resulted in views of Homeland from a single tweet, which in an affiliate model would have ultimately been good for the show, good for me, and great for Showtime.


A Common Metric of Success

Getting everyone on the same page is important for any company.

It becomes especially important in the beginning of a startup when you have small teams working on small projects in different departments.  This helps everyone know exactly what metric of success you are going after.  It also helps align groups to determine whether or not the work that they are doing aligns with the quantified goals of the company.

These metrics could be anything such as; pageviews, sign ups, paying customers, shipments made, monthly accounts activated, downloads, etc… The common number helps people in any team from business development to engineering know and understand that what they are doing has an impact on the business.

This type of clarity also helps people decide whether the next task they are going to work on aligns with the vision.

Here is an example of what Panic did

You certainly don’t need a flat panel display pulling in APIs to get the job done (although this is a beautiful way to do it).  A shared Google Spreadsheet does the trick just as well, and you can jump in to see the data behind a graph.

When you question what you are working on, or what the CEO finds most important, you should be able to consult this document, graph, or screen and know the answer.  Its great to help multiple departments start to understand how each team works together towards a common metric of success.


Always Be Helping the @NYTM

Please vote for me at

I have been a member  and participant of the New York Tech Meetup for many years, and it was one of the ways in which I got exposed to great startups in NYC.

I have met some great people, seen some incredible demos, and made some good friends over the years.  When I saw the opportunity to participate further, I jumped at the chance and wanted to pitch how I can continue to be helpful, only this time as a member of the board.

I am running to Always Be Helping the NY Tech Meetup, or simply #abh.  

If I continue to help people get introduce to tech companies, help startups hire more engineers, or simply bring exposure to the meetup, I have accomplished my goal.

For many, the NYTM is a large gathering of tech minded folks around the idea that anyone with a great idea can present to their peers to get feedback, users, pitch practice, networking help, and various other benefits.  What it has evolved into is a great organization for New York, capturing the mindshare of both those new to the tech sector, and bringing back those who have worked in the area for decades.

I have participated since the organization matured from a warehouse meeting led by Scott Heiferman, to a ful fledged non profit transitioned to Nate Westheimer and a full board.  Its been a great ride and the core principles have remained the same which is why it is a thriving group with thousands of members.

I have enjoyed and benefited from getting to know folks involved in many startups and want to continue in the following ways;

1. Always be helping to hire bring great talent to startups

2. Always be helping guide people to the technology sector

3. Always be helping people network with relevance

Hire great talent

Referrals are the best way to get great talent.  By identifying great candidates, understanding company culture, and knowing about openings and needs I hope to be a resources to startups large and small, looking for great people.

Guide and mentor

Having worked on both sides of the table in this arena over the past 8 years I can bring some perspective, answer questions, and know when to get out of the way.  Sometimes people need a sounding board for their next move, sometimes they need more direction and I provide both.


I would like to think I have the unique ability to connect folks together when there is a need.  Identifying the right people and opportunities is helpful to startups that have just started, and those that have been around for years.  I have done both over the years.

If you agree that the NYTM needs this kind of help you can nominate me here and vote for me in December – more info here.

If you agree with helping the New York Tech Community I hope  you can share this mantra and use the #ABH hashtag!

I support the @NYTM and want to help Hire great talent #ABH

I support the @NYTM and want to help guide and mentor #ABH

I support the @NYTM and want to help network #ABH

Getting more members, being active, and supporting great organizations like this make the ecosystem better as a whole, and I hope to continue doing that for years to come.










Buy a machine or buy the parts (creating vs. acquiring)

Last week I read a great post by Bryce Roberts of OATV called A Perfect Storm for Acqihires.

In it, he details the current state of the union for big companies and small ones looking to build out portions of their expertise through acquiring entire companies, and adding/folding them into the larger entity and  concludes:

It’s not necessarily a new frontier we’re entering. The current environment is simply turning up the volume on what has been happening for some time. And it’s only going to get louder. So BigCos and scaling startups, with increasingly valuable equity, are enjoying a perfect storm for acqhires.

I commented on the post, and as Bryce invited me to write up my thoughts, I figured I would do so here.  This is paraphrased from that comment and explored further below.

I can buy the parts to build a car, or I can pay more and buy one that I know will perform.  This is a no brainer decision because of time, quality, safety, and ongoing maintenance.

In the world of web startups,  you can hire individuals and try to make the team hum, or you can buy an agile group that you know can perform.  The issue is the premium you will pay for a fully functioning web startup team, but it may be worth acquiring a fully operational team that you know is going to produce what you want.

I am sure someone could do a better calculation but this is just back of the napkin stuff;

Acquhire option

what are 8 people worth all at once  who can produce? lets call it $10MM

2 engineers
2 mobile client developers
2 designers
2 front end developers
2 BD folks (hey im biased and can’t leave us out :))

Assuming $100K each thats $1MM in headcount instantly.

Cost? $10MM upfront to buy the startup and product.  Great small exit for the team.

Time ~ instant (or 90 days)
Hope they work at your co. for 5 years
You are paying $200K per person for an instahire situation.  (more if you count options, raises, more payments and “other” but trying to simplify)

Hiring Option

Hire 2 people per month ~ $100K/month/per person across 12 months is 24 people at a $2.4MM burn rate.  This obviously does not include ANYTHING else you need to be spending money on like office, computers, insurance, food, other so lets double it and call it $5MM

You get a stellar group that takes approx. 1 month per person to get up to speed (I think this is generous) so you are not running at full speed for 1.5-2 months per person.

Time ~ 10 months (but really longer in my opinion)
Have equal to or less than team in 5 months – hope they all can work well together – and get them up to speed on your product.

Time is now an important ingredient to a startup trying to crank something and suddenly $200K per head for an “insta-team” situation makes a lot of sense.

I believe that you can buy a fully functioning machine, and pay a premium – or you can buy all the parts and assemble a machine yourself.  In the example of buying a car, buying the parts is most certainly not an option, and you are better off buying the finished product from a safe and stable Company.

A million things could go wrong with each scenario above – and I am sure I am leaving parts out, but I wanted to get my thoughts down after the request.


12 years of ebay

I was recently thinking about the sheer number of services I have signed up for, certainly increasing in the past 5 years, and thinking back on some of the old services I don’t use anymore.  I would ventures to say that my time on the VC side of things yielded probably 10 signups a week on the low side and 100 per week on the high side.

What prompted this post however was this congratulatory email from eBay celebrating 12 YEARS using the service.  This is certainly a milestone for me because I am not sure if there is another example of a service that I use anymore.  I still have an account, but never use it.  I still have a domain from 1998 that I bought ( but thats not the same.

eBay is a service (As well as paypal) that I use at least yearly, if not quarterly.  Its certainly had its share of startups that have tried to disrupt its throne – but the sheer volume and breadth have kept it the market leader.  Its a rare site that stays in the top spot so long, and I wonder how much longer the reign can continue.  I don’t doubt the power and utility of the service (I just used it last month) but I wonder if they can sustain it forever.
I always wondered why companies didn’t take the opportunity to give something amazing to their old customers, but I guess it will always be about getting new customers to signup.

Here is to another 12 years eBay!


Foursquare Global Hackathon September 2011

Foursquare held a global hackathon this weekend that spanned the world with events happening in Tokyo, Paris, NY, SF and many other cities.  With a combination of technologies and resources, people came together and built some amazing tools, utilities, and interesting hacks – it was quite an event.

You can find a full list of all the amazing hacks that were created at  You can also get a local look at what got built in NYC at that link.  All said, folks did an amazing job in such a short amount of time – really incredible projects.

One of the best parts of participating in the hackathon was talking to folks making cool things on top of our API.  They also used a ton of other APIs from folks like Twitter, Twilio, US Census data, MTA, venmo,  and many more.

Below is a shot of the final demos that happened in the afternoon


Some of the cooler hacks I saw up that you may want to try out was  - compares your data against the US census data and tells you how “_____” you are where “blank” is something interesting. - Setup a special profile photo for each time to check in to a specific category - certainly one of the most polished using the Venmo API, Spotify, and of course Foursquare was this app that lets you choose and bid on the song coming next at a bar or club influencing what the DJ plays - a quick way to see “whats hoppin’” nearby!  Great way to visually see what is trending


There was no shortage of creative talent, and innovative ideas.  It was inspiring (and intimidating because I don’t code) to be surrounded by so many talented people focussed on the Foursquare API.  We are extremely lucky and thankful to have such a great community of folks interested in building things off of the API. Its also great to have a product focussed company that prides itself on putting out full fledged APIs. This is an important fact, because each part (or all) of the foursquare functionality is available in the API. This means that if you wanted to use parts of the Explore functionality, Foursquare Connect, Foursquare Lists, or even the points system – you could do so in combination with each other or independently.  It is a very exciting way to deploy features which results in really created use cases for the core foursquare foundational elements.

Again, for a full list of foursquare hackathon apps checkout and vote!

There were a ton of places participating around the world, all organized through Meetup Anywhere

Looking forward to many more of these in the future! (I could never forget the first hackathon where we came up with


Continued Disruption: Amazon’s Kindle Tablet

Ever since I ready Bill Gurley’s post Google Redefines Disruption: The “Less Than Free” Business Model I have been thinking about the power Google wields as it relates to Android and its features.  His point is that by providing and owning their own data they can give turn by turn directions in a free app, and share in ad revenue with partners.  Essentially they would be paying these partners to use their software in devices, thus title of the post having the offering be “less than free”.

This is a powerful and very disruptive approach, that has proven both lucrative for Google and a winning choice for the partners.

Fast forward to September 2011 and enter Amazon with a rumored Kindle Tablet that has been used and played with by MG Siegler of Techcrunch.

Aside from a slick sounding device that would be priced well below the Apple iPad, the Kindle Tablet will be playing its own “less than free” card by integrating their own “flavor” of android with the following features worth calling out from the post

But the key for Amazon is just how deeply integrated all of their services are. Amazon’s content store is always just one click away. The book reader is a Kindle app (which looks similar to how it does on Android and iOS now). The music player is Amazon’s Cloud Player. The movie player is Amazon’s Instant Video player. The app store is Amazon’s Android Appstore.

In case this isn’t clear, Amazon is putting 4 “stores” within reach of each consumer.  This is a possible up-sell opportunity for publishers in the book store and music store, studios in the movie store (as well as instant video), and of course developers in the app store.

But wait theres more!

Here is really where the “less than free” model kicks in.  If the rumors are true, you will also get access to Amazon Prime FREE ($79.99 value) as well as access to all the streaming content that Amazon Prime members get.

Doing the math, a $250.00 device (that most likely requires an Amazon account) has an immediate $79.99 discount (now its $170.01) with a single click away buying opportunity for apps, movies, shows, games, books, and more.

Put another way, I wonder what the lifetime value is of a Kindle Table owner?  Getting them to connect the device online seems almost a requirement, and the ability to load it up with “necessary” items and apps seems inevitable.

Many folks cite the finesse and polish of the iPad as a differentiating factor, but as Bill Gurley says in his post above, the difference here is made up of the lower cost.  A cheaper device, that has a arguable larger library, with real world benefits is a great way to tear into the market that seems dominated by the iPad 2 right now.  I don’t presume sales of the iPad will disappear, on the contrary I think they will continue to increase.  However I see the Kindle Tablet (if it has what I described) be the new underdog against the current eReaders, mobile notebooks, and certainly all the other non-apple tablets out there.

The less than free model worked well for Google in just one vertical, and I think will work very well for Amazon across so many.  I see this head fake that Amazon is doing as a way to leverage themselves into the media consumption, purchasing, and home viewing dynamic – with the real world distribution system as an added bonus!