So You Want a Job in Startups?

Dear X: We met for breakfast last week, when you told me you feel unfulfilled with your job. You want to work in the startup arena, either for a promising young company or for a VC, but at anything that will get you a foot in the door. I promised that I would write a blogpost for you with my thoughts, and here they are: 1)Get Educated on Startups; 2) Network; 3) Publish; 4)Dive Deep; and 5) #GiveFirst

Get Read More

How 19 Year Old Harry Stebbings Became a Venture Capital Star

This past week, Brad Feld, Fred Wilson, Roelof Botha and Marc Andreessen all separately praised the journalism of Harry Stebbings. Who is this guy?

While every Harvard MBA is trying to find a way into venture capital, how did an unknown Brit cut ahead in line and become a go-to-source and door-opener? To paraphrase the cartoonist Peter Steiner, it helps that on the internet, nobody knows you’re a 19 year old.

I was introduced to Harry Stebbings’ work Read More

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: David Beisel, Partner/Co-Founder of Nextview Ventures

Dedicated readers (Hi Mom!) know we’ve already gotten a look into Nextview Ventures via our interview with Lee Hower, but the interview above with David Beisel is a longer, deeper dive into some of NextView’s investments, including Code Climate, Bridj (which originated in Vermont,) GrabCad (Estonia!) and others. David also talks about starting up WebInno, which has grown into a huge quarterly event, and how it wasn’t so cool to be associated with internet startups in 2003-4, and … 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

Office Hours with SuperAngel Joe Caruso

Joe Caruso’s investment philosophy and track record is open for all to see on his BantamGroup website–and when you study it, it’s quickly apparent that he’s had over 40 good exits and 6 “golazos”.  We squeezed into a slot on Joe’s schedule while he was seeing entrepreneurs during his regular open office hours at the Cambridge Innovation Center…before he was off to do the same later in the week at MassChallenge, TechStars, and several of the university-sponsored incubators … Read More

Angel Heaven: Building the Ultimate Syndicate Vehicle

Continuing my recent onslaught on articles about angel syndicates. (Last one before I go back to hibernation.) Here is my dream wish list for the ultimate angel investing vehicle.

The Killer Angel Vehicle combines the best of institutional asset management with ease of shopping on Amazon. Let’s have an instrument that delivers filtering, scale, governance, diversification, benchmarking, standard documentation, access, and actionable low cost passive indices. Oh yeah, and make it easy. And easily transferable in a secondary market.

I … 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

New Angel Blogger: Yosko!

Ben Yoskovitz has cranked up his Instigator Blog, and you can tell it’s a hit by the people reading and commenting, like early stage investors Dharmesh Shah, Fred Destin of Atlas, Mark MacLeod of Real Ventures, and Helge Seetzen of Tandem Launch. This week Ben wrote a retrospective on his first 9 months as an angel investor, listing 14 observations. (Only 81 short of Martin Luther’s 95 Theses–perhaps Ben launches the Angel Reformation … Read More