Reheating Ben Yoskovitz: the Lost Post

As I dig through my Google Docs “electronic shoebox”, I’ve been amazed at the stuff in there. Old family pictures. Unfinished to-do lists. And an hour ago I saw a blog post I wrote on 9/13/13, just over 1 year ago, but never posted because I didn’t want to take the time to edit it and make it acceptable.  I am finally putting it up, and I will use red italics to signify my updated comments. Here goes.

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My Favorite Angel Investor I Don’t Know

Apologies for having fallen off the blogging wagon in the last year. I’ve also slowed down the angel investing pace–a little bit because of valuations, but mostly because I’m running another startup, BuysideFX which takes up all my attention. (I’ll tell the story about how I decided to fund that later when we have something big to announce early next year.) Blogging, mentoring, investing, adding value has all dropped off the cliff, but offset by hopefully getting on another rocket … Read More

How to Not Lose Your Shirt as an Angel Investor

I’ll be attending Angel Boot Camp II in Boston on June 14. It’s a terrific event run by Jon Pierce, with lots of opportunities for talking strategies, meeting lots of angels and VCs, and even seeing a few select companies. (Anyone interested, it’s free but you must register.) I’ll be at a breakout session with Sim Simeonov, former VC at Polaris, current angel and born-again entrepreneur with FastIgnite and Shopximity.  Last year Sim gave a great … Read More

My Next 8 Months of Angel Investing: One Fund and a Half Dozen Startups

OK, the title of this post has ensured that I’ve gone and blown any shreds of suspense. But I’m writing this to get feedback from all of you, so feel free to pick apart my logic.

Angel investing itself is 100% bottom-up, i.e., picking the right companies. However, in order to figure out how much I have to spend, I need to think top-down, or macro.  I start by figuring out how much is a proper amount to go into … Read More

Four Weddings and a Funeral for an Angel Investor

Well, March has come in like a lion. Not only did we get 26” of snow two weeks ago in Burlington, but also I’ve been experiencing a blizzard of activity with my angel investments—4 good events, and 1 bad. Which is a great ratio, but then again, these are only midterms, and most final grades aren’t in.

So, what’s to celebrate? The best news came first: an exit on one of my investments.  The good news was accompanied by the … Read More