The Difference Between Empathy and Sympathy

I’ve had a powerful exchange via email with Mario Cantin over the past few days. He pointed me to a post he recently wrote titled Empathy is feeling *with* others and an amazing three minute RSA Short video on The Power of Empathy by Dr Brené Brown. It’s stunning crisp and enlightening. Amy and I are huge believers in empathy. In our book Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur we come back to this idea over and over again as one of the biggest challenges in communication between people.

December 14, 2014 · 1 min

An Example of Life Being Messy – My ER Visit Last Night

Yesterday I wrote a post titled Life Is Messy For Everyone building off of Nick Grossman’s great post Everyone is broken and life is hard. I was in a nice rhythm after being back four days from my month long sabbatical. I felt completely relaxed, I had an awesome day long offsite with my partners, I was generally caught up with things and was loving being home. I’d scheduled a Monday trip to San Francisco to do something important with one of our portfolio companies and overall felt like I was ready to roll through the rest of the year, including committing to ramping up my running with a goal of doing another marathon in Q115.

December 12, 2014 · 2 min

Life Is Messy For Everyone

I love today’s post from Nick Grossman at USV. It’s titled Everyone is broken and life is hard and he starts out with a clarifying statement. “That’s a pretty depressing and fatalistic post title, but I actually mean it in a positive and encouraging way. Let me explain. It’s easy to go about your life, every day, feeling like everyone else has their shit together and that the things you struggle with are unique to you. But then, when you get down to it, it turns out that everyone — every single person I know — is dealing with profoundly difficult and stressful things. Sometimes that’s money, sometimes it’s health, sometimes it’s work or family or relationships. It’s worth remembering this so that we cultivate some empathy when dealing with people — in general and in particular in difficult situations.”

December 11, 2014 · 2 min

MergeLane – An Accelerator for Women-led Startups

I have been talking, writing, and helping advocate for women in technology for a long time. While my most visible role is as chair of National Center for Women & Information Technology (NCWIT) since its inception in 2006, I’ve tried to be actively involved and supportive of as many initiatives as I can. My partners and I are focused on promoting diversity in our fund (here’s a run-down of our stats) and have recently back several female CEOs, with a few more about to happen. At Techstars, we’ve put a huge amount of energy into building a pipeline of female founders and getting women involved in Techstars in many roles, especially at the leadership level in companies and the program.

December 10, 2014 · 2 min

Get Ready For Q115 Fundraising Insanity

One of the dynamics of going away for a month off the grid is that you come back to a wall of data. I’ve been absorbing it the past two days and it’s fascinating to ponder how my brain is processing it versus the normal continuous flow of information on a real-time basis. I’m not a predictor. As we enter the time of year where every media-related thingy publishes it’s “best of 2014” and “predictions for 2015” lists, I simply pass on participating in all of them and read none of them. So – I’ll start with that – this is not a prediction, rather it’s a hypothesis, which is as long as there isn’t a cataclysmic macro event, Q115 financing activity is going to be insane.

December 10, 2014 · 3 min

The One Month Sabbatical

I’m back after a one month sabbatical with Amy. We spent the month in Bora Bora, completely disconnected from everything. It is one of the best things I’ve ever done for myself. At the beginning of 2014, my partners and I had a discussion about ways to sustain the pace of how we’ve been working. We were all tired and were searching for something to try. We decided to each take a one month sabbatical, completely off the grid, during the year. While one person was gone, the other three would cover for him on anything that needed to be taken care of or decided.

December 8, 2014 · 4 min

The Future Will Look Different From The Present

I’ve been thinking about the future a lot lately. While I’ve always read a lot of science fiction, The Hyperion Cantos shook some stuff free in my brain. I’ve finished the first two books – Hyperion and The Fall of Hyperion – and expect I’ll finish the last two in the next month while I’m on sabbatical. If you have read The Fall of Hyperion, you’ll recognize some of my thoughts at being informed by Ummon, who is one of my favorite characters. If you don’t know Hyperion, according to Wikipedia Ummon “is a leading figure in the TechnoCore’s Stable faction, which opposes the eradication of humanity. He was responsible for the creation of the Keats cybrids, and is mentioned as a major philosopher in the TechnoCore.” Basically, he’s one of the older, most powerful AIs who believes AIs and humans can co-exist.

November 3, 2014 · 4 min

Eating Dinner Alone

I arrived home from Boston last night at 5:30pm and realized I had no plans for dinner. Amy was still in Boston since her Wellesley board meeting doesn’t end until mid-day today so I voxed Seth, Ryan, and Jason to see if any of them were around for dinner. Seth was just landing from Vermont where he had been at Ello for the past few days, Jason was in NY at dinner, and Ryan was already at home having dinner with his family.

October 31, 2014 · 3 min

The Trap of Relative Value

Yesterday, at The Calloway Way event at MIT, I ran into Joe Caruso. I’ve known Joe for a while – we met through Techstars Boston, where he’s been a great mentor and very active angel investor. He had just read my post on being uncomfortable with the phase of the current cycle and told me an anecdote from the great Internet bubble of 2001 that I hadn’t heard. A guy came up to me and said “I just sold my dog for $12 million.” I responded, “WTF – who would ever buy a dog for $12 million? That dog must have gold plated teeth!” The guy responded, “Nope – but it’s a normal dog. But I was able to get two $6 million cats for it.”

October 30, 2014 · 5 min