Congrats to the team @ PillPack

I’m thrilled for my friends TJ and Elliot at PillPack on their announcement today with Amazon.

From the moment I met TJ and Elliot back in 2013 – I believed that if anyone was going to reinvent pharmacy it was going to be these two amazing entrepreneurs.  As one of the very first PillPack customers – I’ve believed from day one that PillPack is the future of pharmacy.

It was an honor to have the opportunity to spend time with TJ, Elliot and the PillPack team over the past five+ years.  Their entrepreneurial journey is a case study in how to build successful, mission-driven company from the ground up and I’m thankful to them for including me.

The future of our heathcare system in the US is a bit brighter today as the world recognizes the benefits of PillPack’s innovative approach to improving the lives of patients.

I look forward to seeing many more great companies from the Boston startup ecosystem that will have a dramatic impact on our US healthcare system – some of my favorite people/companies include :


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Maxwell Health acquired by Sun Life Financial

Congrats to Veer, Vinay and the entire team at Maxwell Health on their acquisition by Sun Life.

Posted in Health Care, Information Technology, Innovation, Start-Ups, Uncategorized | Leave a comment

Bowstreet…More stuff from the archive

More stuff from the spring cleaning…great memories from early days of XML and RESTful services.

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from the files : Trilogy/pcOder

Going through my old files/spring cleaning and turned up a bunch of old Trilogy/ stuff.  Thought that Trilogy/pcOrder alums would get a kick out of these.

Posted in Enterprise Software, Entrepreneurship, Founders, Information Technology, Innovation, Start-Ups, Uncategorized, Venture Funding | Tagged , , , , , | 1 Comment

Great post on Software IPOs

Fantastic post here from Alex Oppenheimer on software IPO’s over the past decade.  Amazing how quickly our industry changes and how companies that looked dominant 10 years ago have had to change dramatically or risk being left in the dust.

View story at

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Updated List of Institutional Seed Funds in Boston/Cambridge

It’s been almost 3 years since my last post on Seed Funds – figured it was time for a refresh.

As I talk to entrepreneurs, I am often asked about the best sources of seed funding.

In Boston over the past 15 years (in addition to a great core group of individual super-angels) there are now at least 8+ great institutional seed funds in Cambridge/Boston.  I’ve worked directly with many of them and highly recommend these excellent active funds and partners:

One of the many benefits of working with institutional seed funds is that you avoid the negative signaling effect of taking seed funding from a venture firm.  When most Series A/B venture firms invest in seed rounds – it’s usually either driven by a trusted relationship (entrepreneur who has made them money before) or they are essentially taking an option on the Series A.

Depending on the situation it can make sense to work with venture firms on a seed round.  However, increasingly, my default advice to entrepreneurs with a new project (especially first timers) is to start with the institutional firms that specialize in seed funding (like those above) who generally invest < $1-2M in Seed and then take their pro-rata or step back a bit as you do Series A+.  IMHO – ideal combo is often 1-2 super angels + 1 institutional seed.  With all the usual caveats that each startup is unique and that bootstrapping/capital efficiency should ALWAYS be the desired path.

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Firecracker acquired by Wolters Kluwer

Congrats to the team at Firecracker on the announcement of their acquisition by Wolters Kluwer.  The Firecracker team has worked incredibly hard over the past 5+ years to bring a modern learning experience to medical school students.  Special congrats to Co-Founder Frank Lau, MD who built the first version of Firecracker while @ Med School, Ben Williams who has been heads down cranking on Firecracker for the past 8+ years and Mark Watkins who joined the BOD four years ago and has been a thoughtful and supportive partner for the team.

It’s been a privilege to be part of the journey at Firecracker.

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