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A Venture Capitalist in Vacationland
Interests: family, wine, travel, investing, English manor house mysteries
Recent Activity
Dan, my partner, and Dave often see startups struggling to manage an assortment of advisers, mentors, and directors, even for a very small company. Some founders want to load up the bus with a bunch of luminaries for their pitch... Continue reading
Posted Jan 24, 2019 at A VC in Vacationland
I've seen a number of articles lately predicting an end to free product shipping, perhaps as early as this year for some retailers. The general argument is that rapidly rising freight labor costs, especially among the parcel carriers (UPS, USPS,... Continue reading
Posted Jan 6, 2019 at A VC in Vacationland
'A Goal is a Dream with a Deadline' Chinese Fortune (Cookie, thanks to my fav Chinese restaurant) Every founder has a dream. If not, no one would pay much attention to them. And often, the dreams are big dreams--conquer the... Continue reading
Posted Nov 27, 2018 at A VC in Vacationland
There is no one way to manage portfolio companies. In some, we are on the BOD and in almost daily contact with the founders; in others, we are a passive investor getting quarterly updates, and in others somewhere in between.... Continue reading
Posted Apr 30, 2018 at A VC in Vacationland
Like a lot of due diligence questions, it depends. There are different approaches depending on the level of advancement of the startup. I’ll focus here on what I call ‘Day One’ startups. This is when someone approaches you with an... Continue reading
Posted Mar 5, 2017 at A VC in Vacationland
I heard an interview this morning with Imogene Anne Opton, a 1952 Olympic skier whose Jewish family barely escaped from Nazi Germany in 1938. She and her family were lucky enough to gain asylum in the US. Imogene took up... Continue reading
Posted Jan 21, 2017 at A VC in Vacationland
Amazon is frequently cited as one of the most successful companies able to innovate at scale. And rightly so, having shipped over a billion packages this holiday season, introduced the Echo, created the super profitable Amazon Web Services and now... Continue reading
Posted Dec 28, 2016 at A VC in Vacationland
When I mention this to most founders, they groan and tell me how difficult this can be. It is really frustrating for passive investors to get no updates, in spite of having invested thousands of dollars in your start-up. Give... Continue reading
Posted Dec 11, 2016 at A VC in Vacationland
Maybe it's the tight job market, the cycles of the moon, or perhaps founder inexperience, but my portfolio companies have had multiple cases of bad hires in the last six months. The reasons varied but the results were the same--having... Continue reading
Posted Oct 21, 2016 at A VC in Vacationland
The phrase has its origins from boxing, referring to a fighter who is punching above his weight, fighting an opponent who is heavier and more dominant. Isn't that what startups do everyday, especially those who are disrupting their industry? Being... Continue reading
Posted Oct 11, 2016 at A VC in Vacationland
I often get asked 'what makes a good founder and can they really be the CEO longer term?' Here are a few thoughts on what I look for in the stages of founder development: Operations Chops--for real early stage founders,... Continue reading
Posted Jun 18, 2016 at A VC in Vacationland
This is a question I answered today, probably for the 4th time. The anonymous person asking said: "They asked for your deck, never read or open it, tells you off or too early." Sigh…aside from not commenting on the lack... Continue reading
Posted May 21, 2016 at A VC in Vacationland
The amount of Due Diligence (or DD, in VC parlance) done on founders and entrepreneurs varies widely among investment firms. Some do deep Kroll background searches, others a quick Google name check or use a cheapo service like Been Verified,... Continue reading
Posted Apr 4, 2016 at A VC in Vacationland
I get asked this question a lot. Here's a short list They keep their promises--like taking their prorata and/or leading subsequent rounds They provide strategic value--introductions to other investors, potential clients and channel partners They keep their nose out of... Continue reading
Posted Feb 27, 2016 at A VC in Vacationland
Want to set up a startup board? Want to serve on a start-up board? Make sure that the company does not have any of these skeletons in their start up closet. I am no lawyer, but have paid lawyers plenty... Continue reading
Posted Nov 21, 2015 at A VC in Vacationland
We often get asked the question: What do you look for in an investment? Although I’m sure every VC can have a different take on the subject, here are our key factors: Idea— we rarely see a bad idea, but... Continue reading
Posted Oct 24, 2015 at A VC in Vacationland
RightHand Is Latest Robotics Startup to Grab Venture Capital According to Xconomy, another Boston-area robotics company has raised venture capital. But this one isn’t saying much about what it’s building yet. RightHand Robotics, a Harvard University spin-out based at the... Continue reading
Posted Oct 17, 2015 at A VC in Vacationland
According to the Boston Business Journal, The Massachusetts Institute of Technology, in an extraordinary upending of the traditional model for graduate education, is expanding its prestigious program in supply chain management to include students admitted in large part based on... Continue reading
Posted Oct 7, 2015 at A VC in Vacationland
cbinsights had an interesting article on startups investing in startups recently. What caught my eye was the investment by Flipkart and Accel Partners in Zinka Logistics. What's this all about? Poor logistics operations by FlipKart, it seems... According to,... Continue reading
Posted Sep 5, 2015 at A VC in Vacationland
'There's nothing more dangerous than an idea if it's the only one you have' fortune cookie .. I was eating out the other night--the same night I got food poisoning before my flight to SF--and unlocked the above fortune in... Continue reading
Posted Aug 29, 2015 at A VC in Vacationland
There is an interesting argument going on in the venture world about whether algorithms are better investors than people. The issues are well summarized in a recent Fortune article. The basic premise is whether it makes more financial sense (measured... Continue reading
Posted Aug 22, 2015 at A VC in Vacationland
That was fast! I mean life! Ron Padgett poem This interesting poem (that's it--six words total) got me thinking about the 'life' of startups and how to understand the various stages of birth, growth, maturity and (gulp) death. Well managed... Continue reading
Posted Aug 15, 2015 at A VC in Vacationland
I was driving home through a pretty fancy suburb of Boston today when a beggar approached me at a traffic light holding a sign saying "Fallen on Hard Times". I gave her some money...I'm a sucker for beggars, especially grandmothers.... Continue reading
Posted Aug 8, 2015 at A VC in Vacationland
There are many similar quotes, such as 'we made the road as we walked', or the Australian Aborigines "singing the earth alive' as they walked their roads. The phrase is very appropriate for the startup world, as I was reminded... Continue reading
Posted Aug 1, 2015 at A VC in Vacationland
According to VentureBeat, Quirky has pissed away its $185M in venture funding. I liked the concept when it was announced a few years ago, sort of a VC firm for product inventors. But either these inventors never went online (I... Continue reading
Posted Jul 25, 2015 at A VC in Vacationland