Your First Startup Job


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 Language and Literature) who secured her first job out of college at a large investment bank before returning to school for her MBA. Capable, smart and personable, she was also the type of candidate that most startups shy away from — no technical background, zero startup experience, and a young woman of color trying to break into an industry dominated by white men.

A few months later, Julisa emailed me with great news: she had landed a job at one of the hottest startups in the country, a fast-growing restaurant technology platform called Toast that had just raised $30 million in financing and would later go on to raise another

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The Summer of Initial Coin Offerings

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 Offerings (ICOs) this summer — more than the total amount of venture capital raised during the same period.

At Flybridge, we are wading into this uncharted territory as a result of one of our portfolio companies, Enigma, staging an ICO in the coming weeks.

Many investors in the ecosystem that we respect have shared their thoughts on the power of the blockchain and cryptocurrencies to disrupt many industries (and we share those views) but few have discussed the downstream ramifications to our business. Hence, the purpose of this post.

I won’t attempt to provide all the contextual background regarding the blockchain, cryptocurrencies and why they represent such Continue reading "The Summer of Initial Coin Offerings"


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 companies attacking a complex problem deep in the bowels of IT infrastructure. The company has developed a way to vastly simplify data infrastructure and database schema development through automated intelligent systems that use behavioral and historical data streams to help companies make better decisions. Their solution allows companies to save valuable time and resources by outsourcing some of the "muck work" of data engineering and eliminating the need to develop a full stack data management infrastructure.
You always hear venture capitalists talk about the two things that compel them to make these crazy seed investments in de novo companies: (1) The Team, and (2) The Market. Not surprisingly, both of these Continue reading "Sentenai"

New Year, New Fund

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 ago, we developed a firm mission statement that we would treat early stage founders as our valued customers and have lived by this mission throughout our history. With our fourth fund, launched last year, we are thrilled to continue pursuing our mission of serving brilliant founders during the critical, formative stages of creating their world-changing startups. As part of our work leading into the new fund, we went on a listening tour - talking to founders about what they want and need from their venture capital partners.  We heard a consistent set of themes:  treat them with respect, bring real expertise to the table, and have an investment approach that Continue reading "New Year, New Fund"

Analyzing Boston’s Reindeer (Not Unicorns)

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 been no multi-billion dollar valued tech companies founded in Boston in the last 13 years." With the news that Hubspot has hit $2 billion in market capitalization, I figured it was time to update the analysis. Happily, I found a more encouraging picture, both in terms of the performance of some of the Boston-based public companies and the pipeline of candidates that might elevate into this level of extraordinary value creation. I felt compelled to move away from the oft-used unicorn label and I really just wanted to focus on multi-billion dollar companies because these represent the future anchor companies that Boston so desperately needs, as identified by this recent MIT study on Growing
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The Secret Weapon to Scaling: Sales Operations

AA-sales-potential 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, growth company. I asked her what role she was currently playing and my eyes widened when she replied, "sales operations". "Holy crap!" I exclaimed, "You'll be the most valuable hire a growth stage company could ever make." When the people around us looked puzzled, I realized that not everyone appreciates that sales operations is the secret weapon to scaling start ups. One of the largest friction points to rapid scaling is the sales force. Very few companies have a business model that enables frictionless revenue growth because of their successful implementation of a freemium model - e.g., Bettercloud, Cloudflare, Dropbox, MongoDB - and even those that do Continue reading "The Secret Weapon to Scaling: Sales Operations"

Humility in Entrepreneurs

Jim-Collins-leadership 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 powerful sermon that took a page from David Brooks' "The Road to Character", emphasizing the importance of "eulogy virtues" (e.g., character) as compared to "resume virtues" (e.g., competence). Rabbis have the opportunity to go to a lot of funerals where they deliver - and listen to - many, many eulogies and so his message was particularly poignant. One of those eulogy virtues that he emphasized was that of humility, defined by as:  "having a modest opinion of one's own importance or rank". There is great power in humility, something I have observed in many entrepreneurial leaders. In fact, I find that the entrepreneurs I Continue reading "Humility in Entrepreneurs"

What Makes The Boston Startup Scene Special?

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 their fingertips in the Boston community. Here is this year's version (which I'm delivering this afternoon), complete with a lot of updated content and data on our local tech hub: