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

As always, Steve Blank and Friends Nail It

Readers know I’m not posting much nor doing a lot of (non-syndicated) angel investing now, but I read a great post on Steve Blank‘s blog yesterday inspired by John Selep. The post shows one investor’s framework for tieing in Steve’s management teachings to improve not only his odds of making successful investments, but those of every startup looking to raise money.

In one way it’s a great filter–is the entrepreneur sufficiently sophisticated? coachable? flexible? pragmatic?  But equally important … 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

My reactions to Google #Glass…and a new investment

Yes, @objlphil, I’ve got mine and you don’t.

With that out of the way, our startup has been playing with @googleglass, and we wrote up a blogpost that was featured on TabbForum.  If you can’t get through the registration process at Tabb Forum, you can also see a version here via our new BuysideFX website.

And let me know what you think of the website. I’m doing my writing for the day job, and not for angel investing, … Read More

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

Entrepreneurs: What to Do if You Don’t Have an Idea

This post was originally published in OnStartups. I hope to be doing further guest posting on that site, which is one of my favorites. Thanks to Dharmesh Shah for his edits.

Don’t have an idea yet for a startup?

Then get off your butt and go work for someone else’s cool startup!  And the first place I would want to work would be a company that has momentum, powerful friends, and has been thoroughly vetted by pros.

How can … 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

Why Every Angel Should Beg to Mentor at an Accelerator

The Original Mentor

Most angels who volunteer as mentors cite noble reasons to do so: “paying it forward”, “giving back”, educating the next generation of entrepreneurs, and so on.  I love people who help others purely for altruistic reasons, and I hope such motives stay foremost in mentors’ minds.  The more favors you do, the more come back your way. At AngelBootCamp on 6/14 in Boston, there’s a great session with Katie Rae (TechStars, Project 11) , David Skok (Matrix), … 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

Why I Passed on Investing in (a real but unnamed) Hot Startup

Yesterday I video-skyped with the CEO of an intriguing Startup.  They were recommended to me by one of their investors on AngelList.  They had going for them a) a big addressable market; b) an area which clearly will break out, but with no clear leader; c) two vocal and well-known angel backers, both of who screen more potential deals than anyone else I know, but both only investing in maybe 10 a year; d) other influential investors; e) an … Read More