Life

When I was in Rio a few months ago for the Global Entrepreneurial Congress, I did a talk called “Day1 ” that Endeavor puts on. It’s a 20 minute presentation about “your day 1” – a profound moment that impacted your entrepreneurial journey. I decided to talk about a number of Day 1’s that I’ve had. I’ve always felt that with the dawn of each day is a new chance to “try again to be the best that I can be.” So my Day 1’s vary a lot – some good, some bad, but all full of lessons for me. They include: ...

It’s such an immense relief when the oppressive weight of depression begins to lift. While I’ve had a big struggle the past six months, the last few weeks have been better and recently I’ve felt a broad positive shift in how I’m feeling. My metaphor for my depressive episodes has always been that “dark clouds build on the horizon” as depression approaches. I no longer am afraid of the dark clouds, nor do I go through crazy rituals like I did in my 20s to try to keep them away. I don’t embrace or encourage them – I just accept that they are there. Often they disappear after a few days. Sometimes, like this time, then move on in and block out the sun. And then – like a long Pacific Northwest rainy season, they just hang there. Every now and then the sun peeks through and things feel a little better, but then the dark clouds swallow up the light again. ...

I had Digital Sabbath #3 yesterday. I turned off my phone and computer Friday at sundown and didn’t turn them back on until Sunday morning. I’m starting to enjoy the pattern and had a lot of relief yesterday from the complete disconnect. We had dinner at our house with friends Friday night, Amy and I did some stuff in the morning together, I went for a 9 mile run, took a nap in the afternoon, and we had dinner last night with friends and then watched some comedy on tv afterwards. My brain was less chaotic yesterday and I was able to settle into a calmer state over the course of the day than I had been the previous two weekends. ...

Amy and I are going to be hanging out at the Boulder Book Store on the Pearl Street Mall on Friday from 4:15pm to 6:00pm . We’ll be signing copies of Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur and talking with anyone who shows up about the challenges and joys of a startup life. ...

I’m not religious but I’ve always liked the idea of the Sabbath. One day a week of rest and reflection. I spent the weekend with Amy in San Diego and in addition to a Digital Sabbath (no electronic devices from Friday sundown to Saturday sundown) I took off all day Sunday off from electronic devices, only opening up my laptop on Sunday night to start editing the latest draft of Matt Blumberg’s book Startup CEO. ...

I woke up to an email today from Aaron Schwartz , founder of Modify . I don’t know Aaron other than our email exchanges but he thanked me for Venture Deals which he said has been very helpful to him. His note went on to say: *A close friend of mine, and one of my best friend’s co-founders just passed away after a 15-month battle with non-smoker’s lung cancer. I thought the below article was incredibly revealing about how meaningful a partner and leader can be for a start-up. If you think it would be useful to other entrepreneurs, I hope you’ll take a moment and share it. * ...

If you’ve never been really depressed, it’s hard to understand what depression feels like. This is especially true if the person who is struggling with depression is someone who looks like they are on top of the world, that everything is going well, and that nothing could possibly be wrong. Many people who go through depressive periods are highly functional – I’m a good example of this. If you didn’t know me well, you wouldn’t notice. And, if you know me well, you probably think of me as tired, lower energy than normal, or that something seems slightly off. Finally, if you know me really well, you know I’m struggling to get through each day when I’m depressed. ...

My dad is one of my best friends. I’ve known him for 47 years and other than a few relatively brief moments where we have struggled with classical father / son stuff as I was growing up and separating my identity, he’s always been a buddy, mentor, friend, cheerleader, and confidant. I’ve learned an enormous amount from him, and continue to treasure every moment I have with him. ...

I’m spending the day working at Yesware . I’ve been an investor from inception and love what this company is doing. I also love the culture – I wrote about it in my post The Monastic Startup . If you use Gmail and Salesforce and are not also using Yesware, take a look at email for salespeople right now. It’s an atypical day for me. I was supposed to be in DC all day today and tomorrow. I had full days of meetings, including two Startup Communities related events – one with the World Bank and one with a Congressional Caucus on Innovation. I had a few company meetings along with some stuff I was exploring. And I was going to drop in on 1776 and check it out. ...

I asked Amy to send me a picture of my inner animal spirit. She won’t let me share hers, but that’s me on the left. I’ve always felt like a bear. A big, cuddly, nice, soft bear. Mellow. I like to sleep. I like to eat. I wander around, a little curiously larger than comfortable in my slightly oversized body. I’m really fucking ferocious when I’m mad. Which doesn’t happen very often (maybe once a year). Don’t poke the bear. ...