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An entrepreneur turned VC, HBS professor, Dad.
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
Today, we are announcing co-leading a $1.8m seed investment in Sentenai, an exciting machine learning company based in Boston, alongside our friends at Founder Collective, Project11 as well as a new local seed fund, Hyperplane. Sentenai is one of those... Continue reading
Posted Jan 21, 2016 at Seeing Both Sides
As a former entrepreneur, I have always viewed venture capital as a service business. That’s a funny line for many because, historically, VCs are viewed (and at times reviled) as judges or overlords. When we started Flybridge over thirteen years... Continue reading
Posted Jan 12, 2016 at Seeing Both Sides
Paul Graham sparked a furious debate over the last few days about inequality with his blog post, Economic Inequality. He points out that the focus of the dialog should shift from inequality to combating poverty and providing more economic opportunity.... Continue reading
Posted Jan 6, 2016 at Seeing Both Sides
A few years ago, I did an analysis on the Boston-based companies that were worth more than $500 million in value, which I called Boston Unicorns. One of the (somewhat depressing) conclusions I made at the time was "there have... Continue reading
Posted Dec 17, 2015 at Seeing Both Sides
I was speaking at an event last night and met a young woman at a large public tech company that was thinking of moving into startup land. She wanted to know whether her skills would be valued in a smaller,... Continue reading
Posted Nov 18, 2015 at Seeing Both Sides
There has been a lot of good stuff written over the years on the topic of calculating customer lifetime value (LTV). Thus, it amazes me how many times I discover faulty thinking when I talk to entrepreneurs regarding their LTV... Continue reading
Posted Oct 26, 2015 at Seeing Both Sides
This past week was the Jewish holiday of Yom Kippur, also known as the Day of Atonement where you fast and pray in synagogue all day and atone for all your sins over the past year. Our rabbi delivered a... Continue reading
Posted Sep 28, 2015 at Seeing Both Sides
Every fall, I deliver a presentation at Harvard's iLab, open to the community, on what makes the Boston startup scene so special. It has become a nice opportunity to step back and appreciate all the rich resources entrepreneurs have at... Continue reading
Posted Sep 16, 2015 at Seeing Both Sides
This post was co-authored with Omri Stern and originally appeared in Harvard Business Review. Israel has been branded the “startup nation.” For good reason: A tiny country of only 8 million people — 0.1% of the world’s population — has... Continue reading
Posted Sep 15, 2015 at Seeing Both Sides
I have been wanting to read Give and Take since the New York Times article a few years ago described the author, Wharton Professor Adam Grant, and his research on "givers", "takers" and "matchers". I finally got a chance to... Continue reading
Posted Aug 11, 2015 at Seeing Both Sides
There was an overwhelming torrent of news last week. The two Supreme Court decisions and the response to the tragic church shooting in South Carolina are among the most indelible events of our time and all three will be memorialized... Continue reading
Posted Jun 29, 2015 at Seeing Both Sides
There is a bias against solo founders in Startup Land. The conventional wisdom is that being an entrepreneur is so difficult that you shouldn't embark on it alone. Many of the top accelerators, like Techstars and Y Combinator, won't accept... Continue reading
Posted Apr 30, 2015 at Seeing Both Sides
Our immigration reform system is broken. That isn't new news. There is now a fix for high-skilled, immigration entrepreneurs that can be implemented TODAY with no legislation required. That is new news. And it has the potential to break through... Continue reading
Posted Apr 16, 2015 at Seeing Both Sides
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 Mar 26, 2015 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