Jane Miller‘s first book Sleep Your Way to the TOP is out and available in digital and print. This is Jane’s first book and FG Press’s second one. Around the Foundry Group Offices we’ve been referring to Jane as “Sheryl Sandberg meets Chelsea Handler.” If you happened to catch my interview with Jane during Boulder Startup Week, you know exactly how smart, funny, and authentic Jane is. She’s a great CEO (who just sold Rudi’s Organic Bakery) with an incredible amount of experience on the front lines building and guiding businesses. Her writing style is funny while packing a serious punch.

I just read an amazing post from Nikki Durkin, the founder and CEO of 99dresses. It’s titled My startup failed, and this is what it feels like and it is one of the best posts I’ve ever read about startup failure. I almost titled this post “What Failure Tastes and Smells Like” because Nikki does such an awesome job of describing not just what happened, but what she felt throughout the process. The post is long and goes through multiple ups and downs, just like a startup. It covers four years, several near death experiences, recoveries, and then final failure.

MIT is a special place. I was a student there from 1983 – 1990, got two degrees, and was booted out of a Ph.D. program well before I finished. I lived in a fraternity (ADP) on the edge of Central Square (351 Mass Ave) for four years. My first office was that address – for several years I got more mail each day than almost everyone else I was living with combined. My next office was 875 Main Street, just behind the frat. And daily, between Monday and Friday, I walked down Main Street to Sloan or Mass Ave to the rest of campus.

Google dominates search. Sure, there’s a thing called Bing and a few other choices out there, but everything ends up being the blue and purple link thing curated mostly by machines. In an effort to experiment with a different approach, we recently led an AngelList syndicated investment in one potential search challenger, a Kansas City based startup called Leap.it who is taking a different approach based on the belief that machine-based algorithms can only get you so far. They hypothesize that by injecting social and real-time data, along with interactions with real people, your search results become much better.

Our portfolio company JumpCloud is running a survey to dig deeper into the professional lives of IT folks and their move to DevOps. If you are open to sharing your thoughts and experiences, please take their survey. It’s only about five minutes long and they are sharing all of the raw data (anonymized, of course). The survey ends at the end of June. The IT sector is undergoing some interesting transformations as a result of the cloud, DevOps, and mobile. I’m interested to see what the data tells us.

Google dominates search. Sure, there’s a thing called Bing and a few other choices out there, but everything ends up being the blue and purple link thing curated mostly by machines. In an effort to experiment with a different approach, we recently led an AngelList syndicated investment in one potential search challenger, a Kansas City based startup called Leap.it who is taking a different approach based on the belief that machine-based algorithms can only get you so far. They hypothesize that by injecting social and real-time data, along with interactions with real people, your search results become much better.

I’ve been stalled trying to get through two books: Startup Opportunities (with Sean Wise) and Startup Metrics (with Seth Levine). Dane McDonald (FG Press CEO) and my assistant Eugene Wan created a book cover recently to try to inspire me, as an homage to Do More Faster (with David Cohen). It worked. I’ve gotten a lot of writing on Startup Opportunities done in the last week and I expect this week to be a good one.

Lots of people get married on the summer solstice. To all of them – including those getting married today – congrats and welcome to the club! It’s a particularly sweet club on your 21st anniversary if you are a numerophile, which is a word that Amy and I just made up that describes people who love numbers. And blackjack. And Dragons. And Daenerys – what a serious badass she is. And Arya also. But I digress. Can you tell that we recently figured out how to watch the Game of Thrones season finale up in Homer?

With yesterday’s announcement that early-stage VC Greycroft has raised a $200 million growth fund, this type of fund has officially become a trend. But before we dig into the dynamics of it, let’s pay homage to the originator of this concept, Union Square Ventures. In January 2011, USV raised what I believe was the first “opportunity fund.” Prior to this, plenty of VC firms invested across the early stage to late stage spectrum from the same fund (e.g. Battery, General Catalyst, Sequoia, Greylock, Bessemer). Others had separate early stage funds and late stage funds, often with separate teams and economics (e.g. Redpoint, DFJ, North Bridge) typically aimed at different opportunities. But the USV Opportunity Fund was the first time, at least in the post 2001-Internet bubble cycle (or last decade, if you want to put it that way) where an early stage firm created a separate fund to invest in late stage rounds of their existing early-stage portfolio companies. In USV’s case, Fred Wilson explains the strategy extremely clearly in the post The Opportunity Fund.