Video: Phil Beauregard on the Boston Startup Ecosystem

When I back an entrepreneur, I especially like to find that rare combination of brawler and softie. Brawler = pugnacious, persistant, driven, opinionated. But so many people with attitude are just jackasses. (That doesn’t mean you can’t like their products, Uber…)

@objlphil is always ready for a tumble, defending underdogs everywhere. In this interview, he talks about the entrepreneurs and VCs he admires, how @scottkirsner gave him a big break, and his role in starting both the Unpitch luncheon for … Read More

VIDEO: Robin–Connecting Identity, Location, and IoT for the Office

Sam (on the left) and Zach Dunn undoubtedly have been hard to tell apart since birth, but I for one am most impressed by the shared drive, thought, and perceptivity of the vision they share for Robin, their new startup. (Yes, I’m a fortunate investor, thanks to ace bird dog and startup connoisseur Phil Beauregard of Objective Logistics, another data-driven company a few blocks away.)

In the interview, they touch on the possibilities if the presence of a mobile … Read More

VIDEO: Bettina Hein, CEO/Founder of Pixability

Continuing our series of “getting reacquainted with portfolio companies”, I met up with Bettina Hein of Pixability. And the quality of this investment is probably correlated to the quality of this video. With its usual high standards, Pixability–which knows a thing or two about video–volunteered to upgrade the quality of these interviews and film and edit it for us. Don’t get used to it–this blog is, after all, called Insufficiently Edited.

Everything about Pixability, down to the smallest coasters, is … Read More

It’s Wayne’s World! Party On, Excellent Syndicate!

Wayne is IN! And I’m thrilled to be along for the ride. Details below.

Let’s start with some non-controversial startup investment logic:

1)   Critical elements to successful startup investing are staying on top of technology trends and having access to good deals

2)   Smart entrepreneurs seek out as advisors/investors those successful role models who they can relate to (i.e., are the same age, travel same circles, have friends in common, etc.)

3)   I have a limited amount of connections and … Read More

Why I’m Switching Over to @AngelList Syndicates

As hinted in the previous post, I’m changing tactics, even though I haven’t changed startup investing philosophy.  I’m cutting down the pace of individual company investments at least by half and probably more, even though I’m increasing the overall total of the investments (courtesy of @Crashlytics and Twitter). The difference: I’m farming out the work.

Time Frame           Angel Companies/% Money        Commingled Funds/% Money

Last 4 years                      55 deals/85%                         3 funds (80 positions)/15%

Next few years                  5 a year/ 25%                         9-10 … Read More

Everything You Wanted to Know About Boards:Touring the Blogoverse

I’m taking part in a StartupVT conference and will be on a panel speaking about Boards. Here are some of my favorite knowledge bombs dropped by an all-star cast of entrepreneurs and investors. Just last week came this explanation of Advisory Boards vs. Fiduciary Boards from Christopher Mirabile. With that in mind, let’s take a tour of VentureHacks and AskTheVC. ADVISORS From VentureHacks:

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Back Unto the Breach

I haven’t posted, tweeted, commented, attended angel meetings, or otherwise engaged in weeks. And most likely I won’t be for several more weeks, as… I’m starting a new company!  It’s called FX Aligned, and it will introduce 3rd party trading desk services for institutional investors in the world’s biggest market, the $4-5 trillion DAILY foreign exchange market. And just like Jake and Elwood, the Blues Brothers, I’m “on a mission from God, and I’m getting the band back together again.”… Read More

Angel Rewards–It’s the Little Things

Just got back from 2 days in Boston talking to MassChallenge companies and 1 day in NYC with TechStars. (Go Ordr.In! Go SideTour!)While I had a lot of meetings and was overscheduled, it was massively fun. But the highlight to me was when Cynthia Smith of Lynx Sportswear came up to me and started profusely thanking me. I recognized her, but didn’t know why she was signalling me out. I remember hearing her pitch, but sportswear–especially women’s … Read More

Do like Chris Sacca: “Create Value Before Asking for Value Back”

I’m a full-time angel, plus I’m a procrastinator and an information consumer. So, I spend a LOT of time on the cruising the net, and find a lot of great content.  But a video from Foundation, Kevin Rose‘s new venture, was so insightful and full of entertaining stories that I had to stop in my tracks and immediately zip off this post saying just how great it is.  “Create Value Before Asking for Value Back” is a theme … Read More

How First-Time Entrepreneurs Can Establish Credibility: 3 Case Studies

Last week I had a conversation with an eager young first time entrepreneur (let’s call him Joey) just out of school who was looking for funding. If desire equaled fundability, this guy would have raised $50mm already. I try to make it a point to always respond, even though the bulk of those responses will be a “I’m not interested, here’s why, and here’s a thought for what might be good to do.” In his case, I had to roll … Read More