Istanbul, Los Angeles and Monetization = Purveyors of IronGiving

Over the past couple of months, I’ve had the privilege of participating along side some fine purveyors of IronGiving.  As you can read on my About page, IronGiving is the act of sharing wisdom, insight or tips to help others fortify their startups and, hopefully, their lives more broadly.  I thought I’d recognize three of these purveyors and note the good work they are doing for the start up community locally as well as globally (in no particular order):

  • Istanbul:  Endeavor is a relatively new organization to me but one that has been around for several years.  I was introduced to it by Sheila Marcelo, the CEO of Care.com, who, knowing my Polish heritage and immigrant parent background, thought I would gravitate toward it and she was right.  I became a “mentor capitalist” volunteer to Alemsah Ozturk, a 32 year old Turkish entrepreneur based out of Turkey who started a very succesful digital marketing agency.  Basically, I provide a few hours of advice to Alemsah as he thinks about growing his business and possibly raising some money from local angels and VCs.  I’m not sure if my advice will ultimately help or hinder Alemsah, but I found the Endeavor platform and organization to be well run and keenly focused on helping Alemsah and his company.  I’d encourage others to check out Endeavor and get involved.
  • Los Angeles:  Jason Nazar is an IronGiving machine (not to mention CEO and cofounder of DocStoc).  His regular event in Los Angeles, Startups Uncensored, typically packs a room with 300+ local entrepreneurs to focus on an important startup topic kicked off by a panel discussion.   Back in late May, I participated in one of those panels which focused on “How to Raise Venture Capital?”  It was a fun event and Jason does a great job as emcee who pulls no punches with his facilitating questions.  If you are an entrepreneur in the LA area, check out Jason’s next event and follow him here.
  • Monetization:  Anamitra Banerji from Twitter pinged me back recently about co-hosting a meet up around the broader topic of monetization on the web.  Given he focuses on sponsored tweets among other money making areas for Twitter, I thought, “what better leader for a healthy discussion?”.  After he and I sequestered a dozen or so entrepreneur friends, we co-hosted the event in the SF Mission where Lukas, the founder and CEO of Crowdflower, graciously allowed us to use some of his office space.  Not only did all the attendees benefit from sharing insights on topics ranging from crowdsourcing to virtual goods to collaborative filtering, my Trinity colleague, Dan Scholnick, came through with a more tangible act of IronGiving by bringing pizza from nearby Delfina Pizzeria.  It was a productive (and tasty) meet up where IronGiving tidbits flowed freely and I’m excited to participate in the next meet up on this topic.  If you’d like to participate, feel free to ping me.

Overall, kudos to Endeavor, Jason Nazar and Anamitra for living the spirit of IronGiving in Q2.  I’ll aim to highlight more examples and leaders in future blog posts.

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Happy 100th Release to CubeTree!

When I first met Carlin Wiegner and Ross Fubini, the cofounders of CubeTree, it was late 2007. My good friend and former Trinity EIR, Nick Mehta, introduced Carlin and Ross to me as fellow Symantec executives who were starting to brainstorm about a new company.  Over the past two and a half years since that first meeting, I have watched these two exceptional leaders build a world class team of ~20 outstanding individuals and evolve CubeTree into the leading SaaS startup in the burgeoning social software for business category.  Before I jump to the Happy 100th Release aspect of this post, some CubeTree history may be helpful, so here goes:

To begin with, while “Facebook for Business” is considered more commonplace today as a trend within the enterprise thanks in part to visionaries like Marc Benioff talking about the Facebook Imperative, it was quite a nascent customer market back in late 2007.  This was true despite the prescient category call by my former professor and now Enterprise 2.0 super star, Andrew McAfee, who highlighted the underlying trends in March 2006.   Carlin and Ross’ conviction in late 2007 stemmed from their disenchantment with the collaboration products they used within their former employer, Symantec.  They realized that there was a growing gap of unmet user needs in the market of intranet portals and knowledge management solutions.  My own market diligence led me to also have strong conviction that there was going to be significant customer demand for a solution like CubeTree.  One tell tale sign I kept hearing about was the repeated yet unsuccessful attempt by IT departments to control and lock down internal employee usage of Facebook.  Finally, my Trinity partner, Gus Tai, brought his uncanny insight into consumer web trends and end user behaviors (hone via investments like PhotoBucket) to the conversation. 

This joint market and product conviction among the four of us led Gus and me to fund Carlin and Ross in Spring 2008 to go forth and disrupt.  It also helped 18 months later to attract the highly connected Bruce Cleveland at InterWest Partners to lead the Series B.  And it certainly resonated with collaboration luminary and founder of Lotus, Mitch Kapor, such that he got involved as an angel investor and advisor.

Fast forward, two years and 100 product releases later, CubeTree is executing on their social software vision extremely well.  Today, it is a world class, multi tenant SaaS collaboration suite that incorporates an activity feed, employee profiles, wikis and third party integrations. 

But, hold on a minute…  “100 releases”?  Over just two years?  Consumer web startups are notorious for fast iteration, especially when following the intersection of product development philosophies of agile software development with customer development as summarized nicely here.  But a multi tenant, enterprise grade SaaS app? 

Here is a perfect example of the axiom “startups are 99% perspiration, 1% inspiration”.  Carlin, Ross and the entire CubeTree team have executed admirably well and have literally shipped a new release of their product once a week for the past two years straight.  I thought this milestone is worth highlighting and Carlin and the CubeTree head of engineering, Justin Rowe, talk in depth in a recent CubeTree blog post found here about the opportunities that this nimble, high speed development cycle has created for the company to partner with, and ultimately delight, customers.  To me, this underscores the power of the business fundamental of active listening to customers coupled with a lean, nimble and high performing software engineering team and process.  It also underscores the early stage venture capital fundamental of investing in great entrepreneurs who know how to execute like surgeons against a compelling and exciting market vision. 

Carlin and Justin’s interview on their lessons learned is well worth a read and I congratulate them and the entire CubeTree team on shipping their 100th product release last week.  Well done!

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Foursquare meets Right Media (or, Local meets Online Display Ad Exchanges)

I’ve spent the last few years looking closely at various segments of the online advertising space broadly defined and of the 10 new investments Trinity made in the past 12 months, 4 fall into this category.  Those four include TubeMogul (online video analytics and ad targeting), RedAril (announced but stealth), gWallet (online virtual goods and social gaming) and one soon to be announced (will blog about it when public).  While 2009 was a rough year for the economy overall and the online advertising space in particular, things are looking up in 2010 as TechCrunch and JPMorgan note in a recent post.  Hopefully the “invest aggressively during the downturn” strategy that my colleagues and I at Trinity decided to execute on a year ago will ultimately bear fruit and this expected online ad rebound may be a helpful step toward that. 

As for 2010 and beyond, clearly we’ll see growth of the online ad exchange for non premium display inventory, but I’d take this one step further and posit that 2010 will see the advent of ”Local” meets the “Online Display Ad Exchange”. 

Let’s look at Local first.  As this theDeal.com article mentions, companies like Yelp, Foursquare and others have captured mind share quite nicely as leading local consumer web services which are attracting the attention of potential acquirers and venture investors alike.  What do these startups have that is so attractive?  Is their user base?  Revenues?  Technology?  I’d argue that it is none of those, rather, it is the data they have accrued or will continue to accrue via highly scalable and viral social gaming (in the case of FourSquare) or seo/ugc (in the case of Yelp) methods.  While geo targeting has been around for a while via products like Digital Element which provide data streams that enable somewhat crude IP address-based geo targeting, these new entrants have or will have two highly sought after data attributes when it comes to local: purchase intent and freshness.  This is why Google, a cash machine which thrives on purchase intent and freshness in its core search business, is interested in acquiring startups that bring viral, scalable and low-cost generators of such data so that it can further expand its targeting efforts into the lucrative local ad market.

Now what about online ad exchanges like Yahoo’s Right Media or Google’s DoubleClick?   As many of the recent interviews and posts on AdExchanger note, there is an increasing trend around the use of data to augment the identification and prioritization of which exchange based impression to buy and how much to bid to win it.   Demand Side Platforms (DSPs) like Turn, Invite Media, DataXu, Triggit and others are providing agencies and brands the tools and mechanisms to leverage data to make smarter and more granular ad buys. 

So how does Foursquare meet Right Media?  It happens via innovative startups, ad agencies and advertisers who look to innovate the ~$60b direct marketing category by taking advantage of this tsunami of local data coming from either consumer web services like the ones mentioned above, mashed up forms of more traditional sources of offline data and/or the plethora of gps/location data streaming from services like Twitter, Facebook or smartphones.   I believe 2010 will see some exciting new developments at this intersection and I’m happy to compare notes with others, just drop in a comment below to start the conversation.

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“Social Leverage” as a Business Model

This video is great isn’t it?  Certainly pumps one up that social media is here to stay and continue to thrive.  But putting aside hype, there is real business value to be captured with social leverage.

I mention this because I’m speaking today at Defrag, a conference out in Denver that delves into a wide variety of social media aspects ranging from consumer to business issues.  The topic of the panel I am on is titled, “Is ‘Social Leverage’ the next big thing for VCs?”  Fred Wilson, Brad Feld, Roger Ehrenberg  and Howard Lindzon are on the panel as well, all great investors and innovators in the social category. 

As I thought about the panel topic, the basic conclusion I came to after mapping out Trinity Ventures’ portfolio as it relates to social leverage (see below), is that social leverage is powerful as a business model.   It struck me how universal this model can be as it can apply to both business oriented services as well as the more obvious applications we see clearly on the consumer side.  It can create broad mass market businesses as well as thriving vertical, more private and focused communities (as Roger also pointed in the latter half of his blog post about today’s panel here). 

The business model of Social Leverage enables lower cost of customer acquisition (viral in consumer ala PhotoBucket for photo sharing and botttoms up trial and adoption in enterprise ala CubeTree for a next gen intranet) as well as lower cost of content acquisition and content management (users contribute content, rate content, moderate content ala Care.com in consumer to help find a babysitter and LoopNet in enterprise for commercial real estate listings). 

I’ll have more to say on this during the panel and I look forward to hearing how Fred, Roger, Brad and Howard define Social Leverage and to get your input.

social leverage

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“Real Time”: Overhyped or Problem Solver?

rose colored glasses

There has been a lot of talk (hype? buzz?) in the investment and entrepreneur community around the concept of Real Time on the web this year. Twitter’s fast growth and its real time message stream certainly brought a spot light to this concept and fueled the excitement. Facebook is more and more focused on real time as well via their FriendFeed acquisition and even open sourced FF’s core Real Time web server technology.  There certainly seem to be more people with rose colored glasses than naysayers at this point based on my non scientific surveying (see links below).

As I meet startups and entrepreneurs in this space, I’m still trying to distinguish the signal from the noise around Real Time by defaulting to the fundamental question of “what specific customer problem are you solving with Real Time?”  This is usually quickly followed by, “how do you generate a lot of revenue by solving that problem?”  It feels like there are money making opportunities for investors and entrepreneurs alike around this trend but I’d like find a better answer to the first of these two basic questions.  I’m optimistic that there are pain points to be addressed (see below) and I’m less focused on the second question as historical business models can be brought to bear (e.g. targeted and contextual ads, data subscription services, freemium upsells) once traction (e.g. sustained usage and adoption) is achieved.  I do believe the customer problem statement around Real Time has yet to be clearly articulated.

For those interested in some background on the theories, theses and thoughts on what “Real Time” means, check out this sample of blog posts which I found useful (in no particular order)

  1. ReadWriteWeb (higher level overview)
  2. Anil Dash: (more technical description of underlying enabling technologies and where they are going)
  3. John Borthwick at BetaWorks:  (positive summary and opinion on trends)
  4. Nova Spivak - (positive summary and opinion on trends)
  5. @vanelsas -  (negative opinion on trends)

From these links, these tidbits jumped out at me:  Dash warns, “And whenever we see something shiny and new, we have the temptation to use technology for technology’s sake, whether or not we’re solving a real problem or providing a real value.”  Borthwick predicts, “Over time tools will emerge to provide real context to these pile up’s.”  Spivak argues, “One of the most difficult challenges will be how to know what to pay attention to in the Stream.”

Crossing out problems and writing solutions on a blackboard.

To me, these comments suggest that there is opportunity around Real Time but that the customer problem statement is still amorphous.   For sure, this is often the case with nascent markets and it is exciting to see potential solutions.  Here is my quick attempt to use examples to boil down the basic problem(s) that can be solved with Real Time today:

  1. Help me make a decision:  Stock trading and defense intelligence are two obvious industries where Real Time decision making is critical. Professional hedge fund algorithms use real time data feeds from Bloomberg terminals and Thompson Reuters Estimates to successfully execute automated trades. Perhaps companies like StockTwits may become the next Bloomberg where they provide real time data and chatter to day traders or stock enthusiasts like me.  (Disclosure, StockTwits cofounder Howard Lindzon is an investor and board member with Trinity Ventures at TubeMogul where I am a board observer).
  2. Help me stay in the know:  Breaking political news, sport scores, celebrity trends, disasters, the latest viral video/joke and next gen tech gadget rumors are all content types that are food to those who lust after being on the bleeding edge of “in the know”. I’m personally not in this camp but recognize that sizeable web publishing businesses and audiences have been built on tracking and reporting on these topics. I could see how each of these sites could benefit from the addition of a stream of Real Time content. For these sites though, Real Time becomes yet another feature as opposed to a core piece of functionality. Perhaps one of the dozen or so real time search engine startups will break through to own this feature and be the ubiquitous Real Time arms dealer to publishers.
  3. Help me save money: This is something I haven’t seen enough of yet. As someone always on the hunt for a bargain and value, I’d love to see a Real Time stream that analyzes deals and offers related to products I’m shopping for at a given point in time.  I’d like to see real time alerts that ping me proactively when a Woot or Swoopo auction is about to expire so I can jump in if necessary.  Or ping me when the same item just gets listed on eBay or Craigslist.  I don’t want to sign up to each merchant’s alert mechanisms, rather, I’d prefer to have a centralized proactive feed that combs the thousands of merchant and listing sites out there for me in order to find the best deal at that point in time.  The closest thing I’ve seen to this in concept is ShopItToMe but albeit as a periodic email newsletter rather than a Real Time steam.

How about you?  What do you think is the sweet spot customer problem to be solved with Real Time?

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What is the Difference Between Leadership and Management?

trinity venture ceo and founder dinner pic 2trinity venture ceo and founder dinner pic 1  

What is the difference between “leadership” and “management”? 

This past Wednesday night, over 50 CEOs and Founders from across the Trinity Ventures portfolio gathered together for our annual CEO and Founder dinner to debate this question.  Imbued by energized networking and copious cocktails, we explored and debated the fundamentals of leadership and management in difficult times, since, especially in this economic environment, world class leadership and management skills are crucial to the success and growth of a business.  While our portfolio company leaders represent an extremely seasoned and high caliber group of executives, all enjoyed revisiting and reflecting on these fundamental values.   I thought it worth summarizing the key examples and takeaways as I found it a good fit with the spirit of IronGiving.

The discussion topic, Leadership in Difficult Times, was facilitated and led by our guest speaker, Professor Charles O’Reilly from the Stanford Business School.  Professor O’Reilly’s discussion included aggressive Socratic style cold calling of the audience (after all, he is a business school professor) and spirited debate.  We examined three real world scenarios brought to life via video clip interviews with three high tech CEOs: Bill Campbell, former CEO of Intuit, current Chairman who covered a situation where his authority as a CEO was openly challenged, Kent Thiry, CEO of DaVita who covered an instance where a high performer on his team clashed with the existing company culture  (be sure to click on his name to watch the YouTube video and get a flavor for his colorful leadership style) and Brian NeSmith, CEO of Blue Coat Systems who covered a scenario where an engineering rock star was disrupting productivity.

Crew team

The most succinct answer to the above question came from Brett Wilson, CEO and cofounder of TubeMogul, an online video analytics and advertising startup Trinity invested in earlier this year.  Brett stated emphatically, “Leadership is about inspiring the team to win the game, and management is about the x’s and o’s of how to win”.  I couldn’t agree more and as a former crew team guy, I thought the image above captured this mixture well - inspired team members can pull hard on the oar but they also need to do so in unison and with rhythm. 

I won’t go into the details of each scenario but the high level takeaways include:

-          CEOs need to embody BOTH leadership and management to be effective.  This was the simplest yet biggest lesson.  The best CEOs do both.  It isn’t easy, but the rewards and returns are even greater for those who can. 

-          CEOs are signal generators.  What they do and say ripples across an organization in unspoken and obvious ways faster than you think.  Be aware and cognizant of your actions at all times.

 -         Firing someone is hard, but not acting quickly and decisively to address performance and/or culture fit problems is usually even more damaging to the company and other people involved.

I’ll try and get the full set of slides that Professor O’Reilly went through and post them here as I think they are useful for any reader to take a quick look at, stay tuned for those.  In the meantime, I welcome any comments or examples of great leaders who balance both leadership and management.

Update – here are the slides from Professor O’Reilly. They don’t contain the embedded video interviews we went through during the dinner but it should give you a good sense of the material covered and ideas discussed, enjoy —

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Enterprise 2.0 in 2010: Twitter / SharePoint / Google Wave / Facebook Tailwinds Fuel Growth

ep2023 Thx to Geek and Poke for the image above.

The term “Enterprise 2.0” was coined back in April 2006 when Andrew MacAfee wrote this Sloan Management Review Article.  Since, then MacAfee has become almost synonymous with the term Enterprise 2.0 and is even coming out with a new book on the topic to be published in late November 2009.  His blog is one of the most respected on the topic of Enterprise 2.0 and he tweets regularly.  I took Andrew’s very first graduate school class he taught in a class called Technology, Operations and Research back at HBS Spring of 2000 and I always thought he had a knack for sensing early technology trends.

One of my favorite posts of his includes his response to a ZDNet post that states  Enterprise 2.0 is a crock.   I like it as it paints six specific use cases around real world examples of well known companies using various facets of enterprise 2.0 to solve customer pain points.

Another favorite of mine is this post where he describes ten criteria for a successful enterprise 2.0 initiative.  This strikes me as a practical and useful framework for how and why some companies are succeeding with enterprise 2.0 solutions. 

I mention all of this as I intend to cover some trends on this category in my blog here because I’m a real believer in the disruptive potential enterprise 2.0 has.  It really can change the way each of us communicates and works every day, much like how email, broadband internet and IM did.  The above set of links provides a starting point on what enterprise 2.0 is all about and you can check out many other links on MacAfee’s blog for other resources.   For a more hands on interaction, you may want to also check out one of the innovators in the enterprise 2.0 cateogory, CubeTree.  My colleague, Gus Tai, and I led a Series A investment in CubeTree on the behalf of Trinity Ventures back in March of 2008.  CubeTree is focused on disrupting the static (and typically useless) corporate intranet with a next generation social business software suite that is people centric (vs. document centric like SharePoint) and is comprised of an activity feed (similar to what you’d see on your Facebook activity feed), wikis, profiles and other features.   You can get a sample of what real enterprise 2.0 innovation looks like by signing up for a free CubeTree account here.  You can also hear more about it via SAP, one of CubeTree’s reference customers.

 crystal ball

I’m interested to hear what readers think 2010 will hold for enterprise 2.0.  I personally think we will see some interesting events occur that help the enterprise 2.0 category accelerate faster than what Gartner may believe in their July 2009 hype cycle report.  This is based not only on what I’m seeing at CubeTree from a board member vantage point, but also extrapolating from the following macro tailwind trends to peer into my crystal ball for some Enterprise 2.0 in 2010 predictions:

  1. Twitter continues to grow like a weed.  This perpetuates the value of microblogging, status updating and real time ambient awareness.  Their recent $100m financing at a valuation of a billion dollars should help a bit.   My 2010 prediction is that Twitter figures out their revenue model which further perpetuates their success and, as a derivative effect, enterprise 2.0 adoption.
  2. Tens of millions of marketing dollars (if not more) will be spent around promotion of SharePoint 2010  and Google Wave.  Both of these products talk a lot about the various value proposition tenants of enterprise 2.0 including aspects of collaboration and real time.   These marketing dollars will continue to imprint broader enterprise 2.0 awareness upon customers.  My 2010 prediction is that these products will be substantive and innovative but yet still fall short as they remain either too professional services intensive (SharePoint) or too techno centric (Wave) for companies looking for practical, scaleable collaboration solutions delivered in a flexible and cost effective manner.
  3. Facebook continues to skyrocket and perpetuate the value of social networking.   My 2010 prediction is that we see Facebook file their S1 and get public.  I also predict we’ll soon see this social networking giant reach half a billion users globally next year after hitting a quarter billion this summer (note, there were one billion web users in the world as of Dec 2008).   Nothing like a hot Facebook IPO and ~40% global penetration (assuming continued growth of the overall global web user base to 1.25 billion in 2010) to continue real gale force like tailwinds for enterprise 2.0.

What do you think?  Other predictions for enterprise 2.0 in 2010?

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