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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 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
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