An Open Letter to Midd Kids about J Term & StartupGrid

Hi guys. I know that no one from Middlebury is going to be reading my blog unless you’re interested in the J-term project, so first, thanks for your interest. This is the course that I wish I could have had when I went to school. (Although I did have two very good independent studies which allowed me to do my work in the evening after skiing was over.) Folks who otherwise are reading my blog, this concerns my initial thoughts on a January term course being done at Middlebury—if you feel you have something that you can add to the effort, contact me, I’m open for all assistance.

Starting up our own little startup

I hope that at the end of the course, we will not only have built the start of a little company, but we will have started making a dent in the world. How? If you 1) believe that progress is made by the crazy ones who disrupt the old ways of doing things by building a company to do something new, and 2) believe that building an online, opensource, free education site that better organizes startup theory and practice can help improve the odds of success for some of those startups, then you’re going to love this course. And this ain’t just reading articles—you’re going to be learning by doing.

I’ve worked as an employee for 1 successful startup, then started another very successful startup, and then started and buried a very unsuccessful startup. And in this course we are going to go through the same processes that all three of those times. But even if this never gets off the ground, you will learn a ton.

What’s Involved?

Well, in one month we’re not going to be going into legal and finance—there’s no actual entity funded or incorporated—but we are going to be doing almost everything else. The larger and more diverse the talents we attract, the greater the odds we are going to be able to actually show off something to be proud of, and we can definitely build the foundation for something ongoing of value. So let’s consider ourselves all spiritual cofounders. (But you’re better off than most co-founders, since you aren’t subsisting on ramen noodles.)

If Google uses machine learning to catalog all of the world’s knowledge, we’re using human knowledge (and a bunch of head starts and pointers) to begin to catalogue past knowledge (going backward through the calendar, year by year, author by author) to do the same, but better because some things are still better handled by humans.

The task of organizing and sorting knowledge is a little bit like curating phone apps. You start by not knowing any apps, and just seeing a few on an acquaintance’s phone. But going through the appstore is a terrible experience that only shows the most popular apps, not necessarily the best ones. What we’re talking about is a hard problem—just as hard as making an efficient, smart, quality appstore. (And you know how much that sucks, and Apple has plenty of smart people on it.)

Your preliminary homework assignment before January is to think about “how can I get smarter about startups in the most efficient way?” Read some Paul Graham, the founder of Y-Combinator, especially his “How to Start a Startup”. Do some web searches. I am in the midst of watching the Y-Combinator led “How to Start a Startup” lecture series now taking place at Stanford Business School. These are lectures by some of the greatest names in Silicon Valley. You might dive into one or two of the great venture capitalist bloggers (Fred Wilson, Brad Feld, Mark Suster) or you may try to go broad, and search on some of the current curated content, maybe from StartUpManagement, or the First Round Review. Subscribe to the Mattermark Daily.

Want to see and read the same curriculum as Startups 101 at Harvard Business School? Here’s the curriculum. Much more importantly, check out the index of topics on the right hand side, along with Professor Tom Eisenmann’s favorite blog citations. Except we are going WAY more granular. And notice the blog roll further down the side of the page? All of those authors we are going to cover, and more. So I hope you all like to read. And recruit more students, and more can share in the cataloguing and editing process.

What are some of the tasks we’ll need to do? Same ones as at any startup.

Initial market research:  Problem definition, talking to potential users, assessing the current state of the art (“competitive analysis”, so to speak) and the alternatives. The more you dig, the more you’ll realize that the knowledge is all around you, but Google is only a starting point. We’ll be providing the curation.   For initial homework, over the next few weeks, talk to anyone who is interested in startups. Where do they go for knowledge? How much do they know? What kind of questions and frustrations do they have? If you are already a student of startups, what frustrations do YOU have?

Content Research and Organizing: This in a way is the heart of the course, and much of the value we are creating. And it’s not just blogs, it’s videos, podcasts, slideshares, whatever.

Content Creation: When we find some controversial areas—say, in the topic such as “non-compete agreements”, we may ask some of the market thought leaders their opinions. This may come out in the form of articles, but I’d like to do it via film. For NEVCA, we want to interview lots of the local VCs, lawyers, bankers, angels, and entrepreneurs. (Here was my first attempt, but we can do better. Feel free to scroll through what I’m creating and make comments or suggestions.) What we create depends on our talents. Know someone in the theater department who wants to be the reader for audiobooks? Sign them up to be the voice creating podcasts, reading our “top 10% blogs”. Editing is never just objective, it’s subjectives. And since this is about an educational site, there is no better judge than you all if an article makes you smarter. So perhaps we’ll give out awards based on your votes. (I retain the right to veto popularist dreck. Especially if the blog mentions the author’s Tesla.)

Product Management:   This is a big topic, but some of you will act as product managers, be that coordinating between disciplines (say, keeping design and programming on target), determining what features must be in the “minimum viable product” we can ship by the end of January, making sure that “QA”—quality assurance is maintained, etc. Included, however, should be a design that we can grow on and update for years.

General Company Management   Who is going to do what? By when? We will do a stripped down, weekly edition of “Objectives and Key Results”. While fortunately almost everyone is in one location, I will probably only be available in person Fri-Sun. So, we’ll need to figure out a communication method (Skype, GoToMeeting, Google Hangout), etc. How about Yammer, or Slack, or Campfire for getting organized. I’m used to Google Docs, we’ll need some type of general management and communication approach. If you have something that works well, we’ll use it.

Web App Design: User Experience and Interaction. This is where we really need to do some tests, try stuff out, and in quick order. I doubt that we are going to have an actual grid, but who knows? We probably will try to break into groups, with one group running a four day design sprint, a la Google Ventures. That makes it tight for having the coders getting something out. Which is why startups never sleep. BTW, the GV Design blog is a terrific resource. Gorgeous design is what made Apple Apple, and why Google had to buy Nest. Design matters.

Database Design: There’s lots of free stuff, but we want this to be able to scale with minimum technical debt. If you don’t understand that last phrase, you will by the end of the course. Hopefully via reading, but probably via practice… Both Web App design elements will be working with Adam Bouchard of Agilion Apps, and I hope to get some of the various Burlington design pros (for example, JDK) to donate a day or two at the start to take us through the process.

The Reward: Well, it’s intrinsic, but we will certainly do a few field trips, one to Burlington, home of various hot startups, like IrisVR (run by Shane Scranton and Nate Beatty, both recent alums) and Ello, as well as Boston (perhaps we’ll see companies like Bridj, run by Midd alum Matt George) or Midd VCs like Alex Finkelstein of Spark and Dustin Dolginow of Atlas Venture. And the stars of the class can definitely get intros to a lot of the cool people and places, and have something they can be a lot prouder of on their resumes than my “just make time for skiing” J terms.

You get the idea. I’m posting this now as it’s late, but hopefully this gets your juices flowing and will persuade you to apply for the StartupGrid class. I just added a tab (look up to top of the website) for StartupGrid. And I’ll start transferring info over to there. As of now, I’m planning on being in Middlebury on Thursday, 10/30, and hope to catch some of you at dinner. My phone is 802 922 2916, Skype is tdanco (although I’m not often on there), I like to Google Hangout, address, and email is the same. Feel free to contact me (or on campus Jake Vacovec) with questions.

Go recruit some coders!

Head of TechStars Boston, Semyon Dukach

You can’t not love (or if you’re a New England investor) not co-invest with Semyon Dukach. I once wrote a blog called “And this year’s word is Co”; the only person I know of, who was my CO-investor in all 4 of those companies (CoachUp, coUrbanize, CoEverywhere, CommandIQ), was Semyon. Here’s a semi-complete list of what Semyon’s invested in.

Besides our taste in startups, we have some other things in common. We both did bizarre things out of school that people thought were wild and risky–he headed one of the infamous MIT blackjack teams. Back then, we both learned a lot about going for gold and suffering the occasional crash. Which of course prepares you for life as angel investors. And we both started a few companies–with one of his successes being SMTP.

Unlike me, Semyon, however, is no ordinary angel, however. (Not the least of which he doesn’t have grey hair and glasses. I’m talking about both of us, Joe Caruso.) Because he now leverages an entire ecosystem to churn out companies, making him possibly one of the most important startup people not just in Boston, but the whole East Coast.

He’s smart. He’s savvy.  He works his butt off. But as is evident in the video, the secret sauce of his success as a mentor and investor: he really, really cares. Once TechStars class graduates in a month, we’ll sit him down for a really good interview.

PS: Michael de la Maza pointed out in the comments that if you want to join Semyon’s AngelList Syndicate, you can do so here. Brad Feld of Foundry Group is, and that is smart company!

For now, enjoy this blast from the past:

semyon blackjack




The cofounders of indico–unplugged, unedited and unprepped

Probably the hottest company coming out of TechStars Boston in the past few years is indico. In keeping with our recent videos of Boston tech companies and investors, today with no warning we torpedoed indico’s  two co-founders, Slater Victoroff and Alec Radford, with quiz show style questions that let’s them show their true selves in topics that are:

1) Biblical; 2) Photographic; 3) Fictional/Engineering; 4) Historic/Poetic; 5) Mathematic/Cinematic; 6) about Source and Sorcery; and 7) Psychological. After question 1, you’ll know why I’m thrilled to be an investor.

And to show you exactly how geeky and proud these guys are, here is an example of Alec’s cat as described in question #2. Check out the source code on

Are you interested in machine learning and want some cool developer tools? Download some of their machine learning APIs here.

Want to join the team? Check out their job board here.


And even though as a Catholic I regret the loss of Alec as a future priest, as an art lover I am happy to post pictures of his cat Iggy in 50 shades of grey (see question 2). And by participating in this film, I now have a Bacon number of 7 (courtesy of Slater, a 6.) My Erdosz Bacon number, alas, is infiniteindico2

iggy clean

Iggy intact

iggy fractured

Iggy indicoed (see question 2)

PS: want to see the Spidey-math referenced in the interview? Spiderman_Final_Report

Lee Hower, Partner/CoFounder of NextView Ventures

Lee speaks so well, it’s almost pointless for me to comment. Watch it and you’ll understand how NextView has been able to raise a fund and rack in 3 exits in the past 6 months. Just a class outfit.

Here are some shownotes related to the video.

0:30 Being a double unicorn–getting in early at Paypal and LinkedIn

3:00 Moving back to New England from Silicon Valley

4:45 Where NextView fits in in the VC ecosystem

6:30 Sourcing early stage deals

9:15 The investment decision process

His company website:  NextView Ventures

Lee’s blog: AgileVC

David Beisel’s blog and a link to WebInno, Boston’s tech demo destination

Rob Go’s blog and a link to the new and improved Hitchhiker’s Guide to Boston Tech (MUST READ)

Jay Acunzo’s blog, SorryforMarketing

Talking with coUrbanize CEO/CoFounder Karin Brandt

I was delighted to catch up with Karin Brandt. I was even more delighted to learn that coUrbanize‘s product is taking off. And I was really really happy to learn that coUrbanize is cash-flow positive just a year and a half out of her TechStars Boston 2013 class. (Her fellow classmates Codeship were featured a few days earlier here.)

coUrbanize’s value proposition is easy to understand: it helps communities and urban developers build better cities, together. With its interactive platform, coUrbanize helps developers to distribute project information and gather online feedback so everybody has the facts and can easily participate. This minimizes misunderstandings that can cause confusion, objections, or unnecessary delays. And that saves their real estate developer clients and municipal clients big bucks and big headaches.

Karin talks about her current challenge, which is to take her proven business model and making it scale. First steps–building up a sales force, which I have always found the toughest task. But when your product is an order of magnitude easier and better than the traditional way, sales gets a lot easier.

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 in and around Boston.


JoeCaruso office hours

Joe talks about why he prefers conversations to “getting pitched”, some of the most common mistakes entrepreneurs make while telling their stories, the need listen to what the market is telling you, advice for new angels, and other nuggets that anyone involved in the venture game will enjoy.

Catching up with Codeship

In the past month I’ve started on a 5 Step Program to Regain My Investing Chops, and part of that is to revisit with my existing portfolio companies. I’m going to be the local ones and posting the videos I’m making while I’m at it.

Some of the Codeship team (Navy? Flotilla? Mannschaft?) were back at TechStars to share with the current class some of their learnings, and I caught up with them just after. (And got one of those SWEET sweatshirts like Flo is wearing. Who says mentors don’t learn from their mentees? I’m getting my next swag via Bratislava.)

Anyway, enjoy. And if you’re creating software with Ruby, Java, Python, PHP, etc., there is NO reason not to use Codeship to test and efficiently and continuously deploy your code. Check out their Youtube Channel for lots of demos and tutorials of the features they’ve built. And spoiler alert–they’re hiring!

codeship logo


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