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An entrepreneur turned VC.
Interests: Baseball (Red Sox diehard), politics (free-market Democrat, progressive policy wonk, The Alliance for Business Leadership), education reform (Facing History and Ourselves)
Recent Activity
I participated on a panel at the First Growth Venture Network yesterday on product-market fit and customer acquisition. Lowenstein's Ed Zimmerman, our host, asked me to cram a semester's worth of content (related to my HBS class) in 10 minutes... Continue reading
Posted 6 days ago at Seeing Both Sides
Around this time of year, many students are focused on finding a job in Startup Land and building their careers. If you have your own idea and no one can talk you out of it, that's awesome. But for most... Continue reading
Posted Mar 16, 2015 at Seeing Both Sides
There are a number of founder leadership models that can work well as a startup evolves. I have lived a few as an entrepreneur and worked with many as a board member. Getting the founder model right is critical because... Continue reading
Posted Mar 4, 2015 at Seeing Both Sides
Conventional wisdom suggests that the most important metrics for a startup - such as unit economics, cost of acquisition, lifetime value, churn rates - typically get better with time. I hear this asserted frequently by entrepreneurs who confidently project their... Continue reading
Posted Feb 9, 2015 at Seeing Both Sides
One of my favorite business books of all time is Crossing the Chasm by Geoffrey Moore. It is a classic. My boss and mentor from Open Market, Gary Eichhorn, made the entire management team read it in the 1990s to... Continue reading
Posted Jan 13, 2015 at Seeing Both Sides FlyBridge Infographic 2014 Continue reading
Posted Dec 30, 2014 at Seeing Both Sides
One of my favorite childhood books was SE Hinton's The Outsiders. For whatever reason, I always related to this tough group of teenagers who felt like societal outcasts just because they were born on the wrong side of town. I... Continue reading
Posted Dec 1, 2014 at Seeing Both Sides
Becoming an entrepreneur is illogical. If you were to calculate the expected value (i.e., the probability-weighted average of all possible outcomes) of being an entrepreneur as compared to living the safe life of a traditional executive, it wouldn't even be... Continue reading
Posted Nov 3, 2014 at Seeing Both Sides
Last week's successful IPO of e-commerce giant Wayfair (market cap $3B) and this week's impending IPO of Hubspot (if it prices in the range, market cap $600m) has many in the Boston tech community celebrating. They are not alone. 2013... Continue reading
Posted Oct 6, 2014 at Seeing Both Sides
Every September, I give a presentation at Harvard's i-Lab to provide a guide to the Boston start-up scene. Students from around the world descend on Boston every fall to attend the amazing universities, but often fail to venture outside the... Continue reading
Posted Sep 18, 2014 at Seeing Both Sides
According to Webster’s Dictionary, the word “programmatic” was first used in the late 19th century. Despite its long tenure in our lexicon, the word was an obscure one until recently. If you aren’t familiar with it yet, if it hasn’t... Continue reading
Posted Sep 2, 2014 at Seeing Both Sides
In 1998, Yom Kippur fell on September 30th. For most of the Jewish community, the date of the most important holiday of the year was no different than in other years. For me and my Jewish CEO boss, though, as... Continue reading
Posted Jul 21, 2014 at Seeing Both Sides
My friend, Ed Zimmerman, wrote a terrific post for his WSJ blog - "Help Me Help You" - on soliciting him (and others like him) for investor introductions. I wanted to add to Ed's post and observe that not all... Continue reading
Posted Jun 12, 2014 at Seeing Both Sides
It is graduation season at colleges and universities around the world. This time of year brings stirring commencement speeches from famous (and sometimes controversial) leaders and thoughtful reflections from students on the considerable time and money they spent in academia.... Continue reading
Posted May 20, 2014 at Seeing Both Sides
The trade association for the venture capital industry, the NVCA, gathered yesterday in San Francisco to talk about the state of the industry and some of the key policy issues we are facing. The short list is an obvious one... Continue reading
Posted May 14, 2014 at Seeing Both Sides
(today's blog post was co-authored with my partner, Matt Witheiler, with contributions from our colleague, Caitlin Strandberg). When we make an investment decision at Flybridge, it is typically because of the intersection of two forces: (1) a top-down thesis about... Continue reading
Posted May 8, 2014 at Seeing Both Sides
Apologies to readers of my blog who care only about my writings on technology and entrepreneurship, but I was compelled to write a more personal post in honor of the 50th anniversary of LBJ's signing of the historic Civil Rights... Continue reading
Posted Apr 26, 2014 at Seeing Both Sides
As a venture capitalist, I spend my time thinking about talent. Who are the best people in the world to invest in? How do I help them attract the best people in the world to team with them to build... Continue reading
Posted Apr 10, 2014 at Seeing Both Sides
For the last few years, many leaders in the Massachusetts innovation community have been arguing that non-compete agreements should be eliminated. Article after article has been written in support of putting this policy forward to increase the dynamism of our... Continue reading
Posted Apr 10, 2014 at Seeing Both Sides
When the Cold War ended, President Bush (senior) used to talk about the peace dividend, the downstream economic benefit of reductions in defense spending. Echoing these words, one of my CEOs declared to me the other day that last week's... Continue reading
Posted Mar 30, 2014 at Seeing Both Sides
When this 10s decade is over, we will look back and be amazed that a mere ten years prior, a few, absolutely massive financial institutions controlled the global banking industry. Software is eating the world, as Marc Andreessen famously observed,... Continue reading
Posted Mar 27, 2014 at Seeing Both Sides
Every year for the last four years, Fred Wilson has been kind enough to come up from NYC and join my Harvard Business School class. It is always entertaining, enlightening and fun. As always, I asked the 80 students in... Continue reading
Posted Mar 5, 2014 at Seeing Both Sides
"Opportunity is who we are. And the defining project of our generation is to restore that promise." - President Obama, 2014 State of the Union In a past blog post last summer, I fretted that the latest wave of innovation... Continue reading
Posted Feb 12, 2014 at Seeing Both Sides
I love dressing informally, maybe too much. My wife frequently reprimands me for dressing down. I recently met with a US Senator in slacks and a collar shirt (which I thought was being respectfully dressy!) and he wryly cracked that... Continue reading
Posted Feb 5, 2014 at Seeing Both Sides
I was excited to see's successful IPO yesterday for multiple reasons. First, it augurs well for 2014 as another strong IPO year in genearl and for technology companies in particular. A University of Florida professor has a nice analysis... Continue reading
Posted Jan 25, 2014 at Seeing Both Sides