My Year As An Angel

I’ve been supporting startups for a long time, but was very much heads-down on my own -Going- for several years. Too much so, I think. I’ve also helped a number of VCs on due diligence, deal sourcing, etc. but had not done my own angel investments. Since the acquisition by AOL and initial integration, I’ve had a chance to come out of “blinders on” mode and get involved in several ways.

In addition to my job at AOL/Going, I’m currently a startup mentor for MassChallenge, for the Founder Institute, and for ASTIA (a great nonprofit for women-led startups in NYC with past successes like Mobissimo and Scout Labs) and happy to be a Hacker Angel finally putting some money where my mouth is ) I have to say, it’s been absolutely awesome to be involved with so many great entrepreneurs and try to help where I can. I’m going to leave my views on the current hot topics -superangels, VCs, converts, etc.- for another day. Today I’m very excited to finally be able to talk about my first angel investments, a couple of which have recently opened up more publically!

Locately - An awesome Boston company and MassChallenge finalist, Locately (formerly Cadio Mobile) just announced their $300k angel round. Locately is a location analytics company, focused squarely on businesses. For example, they help retailers figure out where to open their next store, whether their customers are also visiting competitors’ branches, and what other locations around town are good cross-promotion channels. The great thing about their model is it’s phone-agnostic and platform-agnostic, not reliant on downloading apps and sporadic check-ins, and has already won them an SBIR grant from the National Science Foundation. Founders Thaddeus, Eric and Drew are smart but pragmatic, coming from places like MIT and Endeca and have revenue in the door and deals with Nielsen, Havas and Harris. I participated in the round with my fellow Hacker Angels Gabe Weinberg, Jeff Miller and Joshua Schachter, along with David Cancel, Mike Volpe, Reed Sturtevant and Katie Rae‘s Project 11 and others. I’m proud to say HackerAngels led the round- great work, Gabe.

SpeakerText - Pretty much anyone who’s been on the internet in 2010 has heard of these guys. SpeakerText came out of a journalist’s experiences (with a slight detour fighting massive forest fires) and helps video publishers make their videos more usable. With ST 2.0, unveiled on TechCrunch last week by Erick Schonfeld, it’s easy to navigate videos by an accurate text transcript, jump to key points out of an hourlong video, and share clips with friends. Their transcription technology combines ASR with smart crowdsourcing, so it’s robust to a lot of the funny errors that automated transcripts have.  This round is not announced yet but I’m very excited to be backing a guy who knows how to shake the world up, Matt Mireles, with rockstars in the making Matt Swanson and Tyler Kieft. I led the round, which was the first outside money in, with fellow HackerAngel Jeff Miller and some other greats to be announced.

Rapportive - Founders, if you’re looking to raise money, there’s no better example this year than Rahul Vohra, founder/ceo of Rapportive. Whether winning top pitch awards at The Next Web, raves at Open Angel Forum, or getting the best headline of 2010 from ReadWriteWeb editor Marshall Kirkpatrick -“Stop what you are doing and install this plugin”-, Rahul and co-founders Martin and Sam did it all. Seriously, if you’re not using Rapportive, do stop what you’re doing and install it. It shows you a picture of who you’re emailing with, their latest tweets, one-click connect on LinkedIn, and even more goodness for SMBs’ service and sales groups. The $1M round was announced recently by Jason Kinkaid at TC, and I’m thrilled to have co-invested with Dharmesh Shah, Shervin Pishevar, Paul Buchheit, Jason Calacanis, David Cancel, Gary Vaynerchuck, Dave McClure’s 500 Startups, Venture Hacks, and the wily Chris Keller. Oh yeah, YCombinator too

xPeerient - You never forget your first, right? I learned about xPeerient through innocent eavesdropping on another couple’s conversation while dancing tango- true story! Why the ‘x’? Why the “Peer”? Boston-based xPeerient is a community for CIOs/CxOs to learn from each other as peers, exchange best practices, and specifically to help each other with purchasing and sourcing. If you’re about to place an order for 200 phone lines, or buy 10 licenses to Oracle 802.11g, you want to know who else has recently made a similar purchase… how’s it working out for them… what negotiation tactics got them a good price… xPeerient supports all this in a safe, private community, and then lets vendors make special offers to targeted, qualified purchasers. Mark Hall, the founder/CEO, was head of global IT at IDC as well as CIO of CIO Magazine (how meta ) so he knows the space cold and is working with a great founding team. I participated in the second angel round, with co-investors including David Chang of Where and others to be announced along with the funding.

Unnamed YCombinator Stealth Startup – My hands are tied, I can’t talk about this one just yet, but it’s delicious, touchy-feely, always at your service, and kicking serious bicoastal bootay. Stay tooned

My first year as an angel is still going, and I hope to have more to announce soon. If you’re an entrepreneur looking for advice, feedback, or funding, don’t hesitate to hit us up at HackerAngels.