Reinforcing the guardrails of your online marketplace

I’m a big believer in online marketplaces.  I think it’s one of the collaboration functions the internet is most naturally designed to facilitate.  In recent weeks, I’ve met with several founders of marketplace businesses and the notion of protecting the connections you make has repeatedly come up in conversation.  I think the notion is particularly relevant for marketplaces promising an exchange of services that are likely to recur more than once per year.  In these cases, there’s often a strong temptation for the purchaser and/or service provider to go “offline” and establish a 1to1 connection where future transactions happen outside of the marketplace.  This is the worst type of churn for a business because the match was successful and the two parties will continue to transact, albeit without the business seeing any benefit.  While I’m typically supportive of open, user-friendly UX,  I believe a business needs to take steps to protect itself from this type of transaction churn.   (more…)

Who is New York’s best venture capital fund?

CB Insights published their Fall 2013 edition of The New York Venture Capital Almanac last week in partnership with our friends at Orrick, Herrington and SVB. There’s an enormous amount of data presented in this 112-page report, all centered around figuring out who are the most active and the most successful venture investors supporting New York-based startup businesses. A few observations and takeaways:

New York venture investing is hot. During the 4.5 years ending June 2013, over $8 billion was invested in 1,205 New York-based investment rounds. Based on current run rates, 2013 will set a five year record in venture capital deals and funding activity.


Have startup accelerators become the modern day placement agent?

Fresh out of college in 1998, as most of my friends moved to New York City to begin careers in finance or consulting, I took a road less traveled, moving to San Francisco to take a job with Robertson Stephens & Co, then a leading boutique investment bank specializing in technology.  After a few months working on IPOs and secondaries, I gravitated towards a lesser known group hidden away on a separate floor who were helping private companies position and market themselves for venture capital investment.  As the first analyst-level employee to join the Private Capital Group, I learned about this cottage industry called venture capital and enjoyed unfettered access to startup management teams.  It was my first exposure to early stage technology investing and it fascinated me.

At the time, in the late 1990s, there were almost no personal blogs and Twitter was still eight years away from conception. Email was still a relatively new communication medium. Angel List and the concept of “crowd funding” were nowhere to be found. As a result, connecting with the right venture investors was far more difficult than it is today. This created an opportunity for investment banks and advisory firms to serve as a conduit between promising startups and venture capital funds. There were also twice as many investment banks in those days so this was an opportunity for Robbie Stephens to engage early with companies who they might want to work with later on an IPO, and this happened a few times with our clients between 1998 and 2001.   (more…)

Joining SoftBank Capital to focus on New York investments

I’m excited to announce that I’ve joined SoftBank Capital as a Partner on their latest fund to focus on early-stage investments in New York.  You can read more about it here and here.

Over the past six years, I’ve been fortunate to have had the opportunity to help shape the success of a few early-stage businesses.  That journey began at Sphere, where I joined Tony Conrad, Martin Remy and Steve Nieker as employee #7 in 2007 as a business development professional who came to eventually wear multiple hats.  After Sphere was acquired by Aol in 2008, I stepped up to take the reigns from Tony, leading the team as CEO, and eventually rebranding the business  as Surphace.  As the business continued to grow and Aol shifted its strategy, we saw an opportunity to break away from the mothership and, in 2011, divested the business and merged with Outbrain, our closest competitor at the time.  The next 30 months were some of the most exhilarating and fun of my career, as the combination created a clear winner in the space and sent us off to the races.  Having a front row seat to watch a business grow from 50 to 250 employees while taking a commanding lead in a market is an awesome experience and something every startup junkie should experience at least once in their lives.  Outbrain, for me, was a lesson in execution, and working with Yaron, Ori, David and the rest of the team was a true privilege.  While not the most well known or hyped (intentionally so), I’m convinced there’s not a more talented team assembled in the country.  Though through it all, my heart always felt most at home in the early days – when the team fits around a conference room table and every decision seems as if the world depends on it.

Since the earliest days of my career, when I pitched startup businesses to investors as a young investment banker in San Francisco (in the pre AngelList era), the world of venture capital (more…)

The Natives are Getting Restless

This article originally appeared on AllThingsD on April 19, 2013.

If you ask 10 marketers for a definition of “native advertising,” you are likely to get 10 different answers. While the concept is as old as advertising itself, what’s old is new again online and it seems everyone is rushing to redefine what it means to be native. As the river of venture capital dollars increasingly flows toward this buzzy new category, marketing platforms of all shapes and sizes are reaching out hoping to claim their seat on the raft. In many ways, the weeding-out process has already begun, and we’re seeing the offerings that facilitate real reader engagement rise to the top. Still, it’s worth looking at what makes them successful, and, ultimately, what it really takes to be native.

Our friends at Solve Media wrote a thoughtful white paper on this topic, and I’ve combined some of their thinking with my own ideas in order to come up with a holistic definition of native advertising. Here are the five criteria any true native ad should meet:

  • Non interruptive — Doesn’t interrupt the user flow and fits seamlessly into the experience (more…)


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