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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
I just posted a new blog on Product Market fit and it reminded me to remind you that my blog moved a ways back to Seeing Both Sides so if you're still getting email notifications for Boston VC Blog you... Continue reading
Posted Jun 10, 2019 at Seeing Both Sides
New graduates should jump on board one of these high flying companies and go along for the ride Graduating students hungry to dive into the startup community around the world (aka StartUpLand) often struggle to select the right, specific opportunity... Continue reading
Posted May 19, 2019 at Seeing Both Sides
In my blockchain investment work (we have invested in six early-stage projects, including bloXroute, Enigma, FalconX, NEX and two stealth projects), I have been struck by the fact that decades of progress on applying the scientific method to entrepreneurship (e.g.,... Continue reading
Posted Nov 16, 2018 at Seeing Both Sides
I published a new version of my "Rocket Ship Startup List" for 2018, highlighting over 500 startups that are promising places to start (or build) your startup career. You can see it here. Enjoy! Continue reading
Posted Apr 26, 2018 at Seeing Both Sides
When Julisa Salas told me she wanted to join a startup, I was worried. Her background was not exactly typical for StartUpLand and I was concerned her search would end in disappointment. Julisa had been a liberal arts major (English... Continue reading
Posted Oct 24, 2017 at Seeing Both Sides
Note: my blog has moved to Also, check out to see my new book, Entering StartUpLand, which ships on October 10th. Goldman Sachs and CB Insights recently reported that startups have raised over $1 billion in Initial Coin... Continue reading
Posted Aug 28, 2017 at Seeing Both Sides
Flybridge is pleased to announce the creation of XFactor Ventures, a $3m women-focused micro-seed fund. You can read more about it here: My Medium post My partner, Chip's, Medium post TechCrunch If you are interested in submitting a business plan,... Continue reading
Posted Jul 12, 2017 at Seeing Both Sides
I am thrilled to welcome Jesse Middleton to the Flybridge family. Jesse is joining us as a General Partner to help lead our NYC office. This hire is a big deal for us. Jesse is the first General Partner we’ve... Continue reading
Posted Jun 20, 2016 at Seeing Both Sides
I have a new post on my newly designed blog: Growth vs. Profitability and Venture Returns. A reporter from BostInno tweeted that the blog post should have been titled: Profitability isn't cool. You know what's cool? Venture returns.… via... Continue reading
Posted May 17, 2016 at Seeing Both Sides
I've moved out of the dark ages and (finally) shifted from Typepad to WordPress. I will keep this blog site up, but all new posts can be found at Seeing Both Sides. Enjoy! Continue reading
Posted Apr 3, 2016 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 14, 2016 at Seeing Both Sides
(this post was originally published in Harvard Business Review and is co-authored with Nadav Benbarak of Okta.) Growing revenue and profits is a core objective of most companies, and it is the responsibility of every function to contribute to the... Continue reading
Posted Feb 25, 2016 at Seeing Both Sides
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