Entrepreneurship

After all these years, I’m still a heavy RSS user. Every morning I click on my Daily folder in Chrome, open it up, and spend whatever time I feel like on it. The vast majority of what I read is in Feedly and includes my VC Collection as well as a bunch of other stuff. It’s almost entirely tech related, as I stay away from mainstream media during the week (e.g. no CNN, no CNBC, no NYT, no WSJ, no USA Today, no … well – you get the idea) since I view all this stuff as an intellectual distraction (and much of it is just entertainment anyway, and I’d rather read a book.) ...

I’ve talked openly about my struggles with depression over the years and have engaged deeply in an explorations of entrepreneurship and mental health through several different organizations I’m involved in. On February 16th, from 3pm to 5pm , I’m doing a free public event with the Carson J Spencer Foundation about entrepreneurship and mental health. For some quick context, they did a short intro video with me on the topic. ...

I was at a fascinating dinner with a bunch of founders and investors last night. Until I was 35, I was often the youngest guy in the room. While this was a seasoned crowd, much of the experience – both around creating companies and funding companies – started around the mid-2000s. As someone who has been doing this since the late 1980s (I started my first company in 1987) I definitely felt like one of the old guys in the room. ...

I was in a conversation last week with a friend who asked “do you think this is the beginning of the end?” We were discussing something totally wacky that had just happened that clearly could be viewed as an indicator that we have crested the peak of this economic cycle. Then, earlier today, I was on the phone with one of my favorite lawyers and he made a joke about a deal I’m doing as harkening back to the late 1990s. He asked if I thought it was an indication of the top of the cycle. We had a good chuckle (probably PTSD gallows humor from 15 years ago) and I suggested that they slow down the hiring of the associates at their law firm so they wouldn’t have to lay off so many in the inevitable downtown. ...

Has the word entrepreneur become too trendy as to have lost its meaning? I’m hearing it and the word entrepreneurship being used in so many conversations incorrectly. Here’s a simple example. On a daily basis, I have an email exchange with someone who says they are an entrepreneur. I respond “What company did you start?” They respond, “Oh, I didn’t start a company, I was the fifth employee of Company X.” ...

I’m feeling fine today. But I know many entrepreneurs who aren’t. They are under intense pressure, worrying about an endless stream of things coming at them, suffering under the weight of imposter syndrome and other sources of anxiety. And, in some cases they are depressed, but trapped by our own culture which stigmatizes depression. Earlier this week Biz Carson wrote an excellent article titled There’s a dark side to startups, and it haunts 30% of the world’s most brilliant people . It started with Austen Heinz’s suicide (Austen was the founder of Cambrian Genomics) and then built into a wide ranging discussion about depression among entrepreneurs. ...

This is the best quote I’ve seen all week. It’s from Greg Sands post on TechCrunch titled The Real Silicon Valley . Greg is a long time friend and co-investor. I’m on the board with him at Return Path and he’s on the board with my partner Ryan at VictorOps . Along with my partners, we are all LPs in Greg’s fund Costanoa Ventures . Greg’s post is great. Here’s the windup: ...

This is one of my favorite lines to use to explain the business life I live. When asked what it’s like to be a partner in a VC firm, be on a bunch of boards, and have a continuous stream of random interaction come my way, I like to level set my reality. It’s simple. Something new is fucked up in my world every day. Now, just because something new is fucked up, doesn’t mean I’m unhappy. Quite the opposite – I’m usually happy, although when the pile of fuckedupness gets high enough I get tired. And day after day after day of 12+ hour days also make me tired. I used to be able to work through the weekends – now at 49 years old I need them to recover, get patched up by Amy , and get ready to go back out there. ...

Amy and I are spending the week in Dubai on the annual Wellesley Art Trip. I’ve been doing some of the art stuff, visited one of our LPs, and have been getting together with local entrepreneurs and investors. Yesterday, I had a magnificent two and a half hour lunch with three guys from BECO Capital – Dany Farha, Amir Farha, and Sorusch Amiri. It started ten days ago with an email from Sorusch in response to a tweet I wrote asking for a recommendation of a book on the history of Dubai. ...

There are lots of blogs and anecdotes on (a) how to build a successful SaaS company and (b) what a successful SaaS company looks like. Yesterday’s post by Neeraj Agrawal from Battery Ventures titled The SaaS Adventure is another great one as he describes his (and presumably Battery’s) T2D3 approach. If you want to follow these posts more closely on a daily basis, I encourage you to subscribe to the Mattermark Daily newsletter . Or take a look at the VCs I follow in my Feedly VC channel . ...