Tag: life

Sep 2 2015

Why This Labor Day Weekend Is So Important

I like Memorial Day weekend and Labor Day weekend a lot. They are my bookends for summer and kick off the official “back to school” fall cycle. I realize that kids are back at school already, but even when I was in school I viewed Labor Day weekend as the official market.

I’m noticing an enormous amount of anxiety in the air. When I reflect on what’s causing it, I suspect some of it is the public market gyrations along with the endless discussion around it. Some of it is the Republican Primary circus and the crazy and apparently unwanted popularity (at least by the Republican establishment) of Donald Trump. Some of it might be that it’s just been really hot outside for a while and it’s time for the cooler, softer tones of fall. And some of it might be all of the construction everywhere, which is at a fevered pitch right now.

I’m in a consistent conversation with a lot of entrepreneurs. “Is my burn rate too high?” “Will I be able to raise the next round?” “Are valuations going to go down?” “What should I do about the coming _fill_in_the_blank?”

Fall is coming. I don’t know what the public markets will do, nor do I know what the private markets will do. But the weather, at least in much of the United States, will cool off and the leaves will turn different colors. And, if 49 years of life on this planet is any guide, there will be an emotional shift from summer to fall.

Let your body, soul, and mind reset this weekend. Turn off the electronics. Don’t try to “catch up” before things get crazy. Watch a movie with your sweetie. Eat some ice cream. Sleep late. Go for a long walk in the mountains somewhere. Read a book. Take another nap. Have a long, slow dinner. Play with your dogs. Or do whatever you like to do to relax.

The fall is always intensely busy. Charge up your batteries and get ready for it.

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May 19 2015

Recalibrating For The Summer

Even though I haven’t been in school for a long time, I still have some tenuous link to the idea of summer vacation. Well, not some much vacation, but a mode shift from going to class every day to doing other stuff, such as playing tennis at least eight hours a day (age 10 – 14) or writing software products (age 17 – 21).

A few summers ago I did a hard shift to maker mode. I did some of my most creative work in a while that summer, including writing Startup Communities and getting started with Amy on the book Startup Life. It was also a powerful summer for some of the companies in my portfolio and I was able to spend deep time with several of them on their product rather than just reacting to all the inbound stuff that was flying at me. I also got in the best physical shape of my life. I worked out – mostly running and biking – almost every day. I slept plenty. I ate well. I spend a lot of time reading and hanging out with my beloved.

At the end of the summer, I blew it as I shifted out of this mode. The fall started with a bike accident in Slovenia and ended with surgery to remove an 8mm kidney stone. But that was only the beginning of a slide into a very deep, six month depression which finally ended in the summer. I didn’t plan for an annual cycle, but that’s what happened on that one.

While I feel mentally healthy right now, I realize that I’m extremely tired. Amy and I slept an enormous amount of the time we were in Paris. While we usually have an epic Parisian meal two or three times during the week, we only had one at the beginning of the week and then cancelled the others because we just didn’t feel like it. We had an amazing visit to the Picasso Museum, but then spent a lot of time laying in bed reading or just wandering around aimlessly, and then heading back to the hotel to take a nap. The heavy fog of fatigue, which settled in on the trip, hasn’t lifted. I’m sure the endless rain in Boulder isn’t helping, but I’m aware that it’s time to shift gears again.

On top of that, I’m pretty tired by the noise in the system. I was tired of it all spring and wrote a few things about it, but the gap between real signal in the entrepreneurial world and the endless noise is at a volume that is very high. I filter much of it out so when it eventually breaks through I know I need to add a new filter, or recalibrate my filter.

At the same time, I’m extremely interested in many of the companies we are investors in. So, I know I’m not reacting to the work, or the types of companies I get to work with, but the systemic noise that isn’t about creating, doing, building, and thinking.

I’m using Memorial Day to Labor Day as my marker for recalibrating for this summer. I’m not going to use the 2012 Maker Mode summer approach but I’m going to design something else. I’m going to let this week roll over me without fighting it as I think about what the recalibration for the summer is, but the new mode will start in a week.

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May 17 2015

Build Your Life Where You Want To Live

Amy and I just got back from a great week off the grid in Paris. We were both exhausted and badly needed a break. When we want to get away from humans, we go to our place in Homer. When we want to lose ourselves in a big city, we go to Paris. We both are incredibly refreshed feeling and happy to be home with the rapidly growing puppy Super Cooper and his friend Brooks the Wonder Dog.

Before I left I did 15 minute interview on WGBH’s Innovation Hub program. I’m happy to do an interview with WGBH anytime they call given the number of hours of my life I spent listening to them during my twelve years living in Boston.

I listened to it on the ride home from the airport yesterday and thought it was one of the better short interviews I’ve done in a while. Enjoy!

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Feb 9 2015

What You Are Instead of What You Are Going To Be

I spent the weekend in Las Vegas with my dad. He’s almost 77 and I’m 49. We had an awesome weekend which I expect he’ll write about in detail on his blog Repairing the Healthcare System in the next few days since he generally does a really nice retrospective of our annual trip together.

As I was reflecting on our weekend during my flight home yesterday, I remembered a discussion I had with Todd Vernon, the CEO of VictorOps, and a long time friend (we’ve been investors in the last three company’s of Todd’s – Raindance, Lijit, and now VictorOps – going back almost 20 years.)

I was at dinner with Todd, his wife Lura the rocket scientist, Amy, and Krista Marks / Brent Milne a few weeks ago. It was just after we’d closed an investment in Krista and Brent’s company WootMath and the six of us were enjoying a meal at the awesome but very loud Blackbelly. Todd and I were at one end of the table and couldn’t really hear the conversation very well without leaning over so we ended up just talking to each other for a little while. That little while turned into a really intense conversation.

Todd made the assertion that something happens to guys between the age of 47 and 50. We started talking about all of our male friends who had gone through various things between 47 and 50, including all the classic mid-life crisis stuff. We reflected back on what each of us had been through in the past few years and where we had ended up. Some was gossipy, some was introspective, and some was piecing together a puzzle to support the assertion.

After a few examples, it came into clear focus for each of us. Todd said a line that has really stuck with me.

“The age of 47 to 50 is optimizing for what you are. Up to that point, we are optimizing for what you are going to be.”

We both acknowledged that we don’t really know much about the psychology of women (well – generally – but especially in this age range), so I’m focused on what happens to men. When I reflect on my own experience over the past few years, I’ve struggled with depression, had a few health scares and had to come to terms with my older body, practiced the concept of detachment, deepened my relationship with each of my parents, built a sustainable relationship rhythm with my brother Daniel, and developed a new level of deepness in my relationship with Amy.

As we went back and forth, we realized that our time in this age bracket is a confluence of a bunch of decisions we’ve made about life. There’s a classical notion of a midlife crisis, but that cheapens the dynamic. A few of our friends have had relationships, especially with their spouse or significant other, blow up while many others have their relationships deepen. We all bought sports cars in our 30s so that cliche doesn’t really hold, and a group of us were divorced in our early 20s. Bizarrely, many of the guys in the gang of divorcees I’m part of all had their first wife cheat on them in their early to mid 20s, so none of us would ever consider cheating on our current wife as the emotional devastation of a busted marriage from your wife’s affair at that stage in life seems to never go away, at least for us. So, as we rolled it around, it wasn’t really a midlife crisis.

But there is acceptance that we are more than halfway through our lives. Our parents are getting older. Some have passed away, others like my dad acknowledge they are likely in the last decade of their life. If you are courageous like my dad is, you can openly talk about mortality and the implications of it. And, as a son, his mortality immediately reminds me of my mortality.

In Bora Bora when Amy and I were together for a month, we discussed mortality a lot. We talked about having “30 good years left in our normative case.” It could be longer, it could be shorter, and it can’t really be planned for.

As Todd and I cycled on this, we came to the notion of “what you are.” In this 47 to 50 segment, we each have spent a lot of time figuring out what we are and optimizing our lives for it. This notion of what we are isn’t static – we’ll keep learning and evolving – but we are no longer striving for “what we are going to be.” Instead of spending time and emotional energy on this, we are spending our time and emotional energy on what matters to us now. What we care about. Who we care about.

My weekend with my dad was profoundly wonderful. He knows what he is, what he likes, and what he cares about. He’s still learning all the time, but he’s not trying to be something he isn’t. He isn’t striving to be something new. He’s just being him.

Todd and I realized at dinner that we are having a lot of fun and getting a lot of satisfaction out of just being ourselves at this stage of life. We’ve each had lots of ups and downs, but we are each married to amazing women, living in a place that we love, surrounded by people who we love, working on things that give us each meaning, and having time to ourselves and with friends that are satisfying. Sure, we each have crappy moments and lousy days, and we each know that at some point the lights will go out, but for now we are focused on being what we are.

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Dec 11 2014

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.”

I just turned seven squared. I’ve now been on this planet for 50 years. In my “normative case”, I’ve got 30 good years left. I’m hopeful I live longer but I’ve also accepted that the lights could go out unexpectedly anytime.

Amy and I used the “30 more good years” as the frame of reference for a lot of our talks over the past month while we were on sabbatical off the grid. We’ve been fortunate to have amazing lives, but we’ve each had our share of really difficult things to deal with, separately and together. And we know we’ll have plenty of challenges and messy stuff to deal with for the rest of our lives.

I read several biographies on our trip. My two favorites were one on Einstein and one on Ada Lovelace. Amazing people, but messy lives with lots of challenges. As I read these biographies, I kept thinking about the timing they lived, the stuff they struggled with, and how the cycle of challenges for humanity continues on endlessly.

It’s easy to get lost in the morass of misery. You can also end up in the “things are good for the other person, but fucked up for me” cycle.

It’s all messy. And we eventually die and it’s over.

Nick’s remember that it’s “worth cultivat[ing] some empathy when dealing with people — in general and in particular in difficult situations” just nails it.

Go read Nick’s post everyone is broken and life is hard. And take a deep breath and remember Everything is Amazing and Nobody’s Happy.

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Aug 21 2014

Is The US A No Vacation Nation?

Amy and I take a week off the grid every quarter. It is one of the things that has kept me sane and us together over the past 14 years.

This morning I saw a great short clip from the Today Show that got forwarded around on the US becoming a no vacation nation. They include an interview with Bart Lorang discussing FullContact’s Paid PAID vacation policy. It also shows an iconic picture of what stimulated this, which was Bart checking his email on his iPhone while riding on a camel with his then girlfriend / now wife in front of some pyramids.

Visit NBCNews.com for breaking news, world news, and news about the economy

Everyone in my universe works incredibly hard. But the really great ones know the value of disconnecting for periods of time to recharge their batteries and refresh their brains. If you want more on this, grab a copy of the book Amy and wrote called Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur.

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Aug 19 2014

Who Would You Miss The Most If You Weren’t Here

This morning’s question during my Headspace meditation session was “Who or what would you miss the most if you weren’t here.”

Over the last few months, my meditation practice has been spotty. Something indeterminate happened and I just fell out of the routine. I’ve been told by my meditating friends that this happens often and not to worry about it, but rather just to start practicing again when you feel like it.

I’m feeling very maxed out right now. I know there’s some cliche about VCs taking it easy in August but that never seems to be my reality. For the past 45 days I’ve pretty much been saying “no” or “I don’t have any time” to anything new that has come up. I don’t really see that changing – I feel full – so this morning I sat down to meditate for 20 minutes.

As I sat down and got comfortable, I realized how incredibly tense I was. Not just physically tense, but mentally and emotionally tense. I carry a lot of tension in my shoulders and when there was a big pop, it was more than physical. I settled into the meditation session and a few minutes in was confronted with the question “Who or what would you miss the most if you weren’t here.”

Amy and Brooks immediately came to my mind. Bing bing bing – I got the right answer. But I know it’s not about that so I just let the thought float away.

Robin Williams came into my mind. I was sad that he was in such distress that he took his own life.

A friend who is going through a divorce surfaced. The pain from my first marriage and divorce jolted through me.

Amy and Brooks came to my mind. I held them there for a few moments.

A work issue that is front of mind intruded. I observed that I was having the thought and let it float away.

Amy and Brooks again.

I felt the tension leaving my shoulders. I sat a little deeper. I listened to what Andy from Headspace was saying, but I didn’t really hear it.

I tried on the feeling of what it would be like to not be here. I wasn’t hear, but was somewhere else, observing here. That became really uncomfortable, so I let it go.

Amy and Brooks.

As I finished the session and stretched, I felt everything soften. My shoulders are less tight. My gaze is softer. I’m clear about who I would miss the most and am going to go spend a little time with them before the day starts in earnest.

Who would you miss the most if you weren’t here?

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Jul 12 2014

Dear VCs: What Happens When Your Words And Your Actions Don’t Match

Almost exactly a year ago I wrote a post Your Words Should Match Your Actions. It was a generic rant that resulted from me watching a couple of VCs blow up their reputations with entrepreneurs I know because of how they treated them.

This morning I ended up on an email thread about this. I’m going to anonymize it, but you’ll get the point. The two people (who I’ll call “Entrepreneur” and “VC”) are both very successful, extremely smart, and very visible.

Entrepreneur: Thread below is 2+ years old, but resulted from VC asking me similar questions. Interestingly, when I (a year later) pinged VC about my new company, not even the courtesy of reply from him. Bad mojo. 🙂

Me: Welcome to the “assholeness-VC-factor.” Hey – I’m important – give me info. Oh – you are now raising money – fuck off.

Entrepreneur: I’m amazingly appreciative to short, polite “no thank you’s”. I don’t know whether VCs think that’s too much work, or whether they want to leave open the possibility of the “must have been caught in my spam filter” excuse when the startup becomes a rocket in 2 years?

I then went on a more serious rant explaining what I think is going on.

It’s worse that that.

In my book Startup Life (that I wrote with my wife Amy) I said that one of the key things that has made our relationship work is that I realized “my words had to match my actions.” After about decade of telling her she was the most important person in my life, and then being late to dinner, canceling things at the last minute because something else came up, or taking a phone call without even looking at who was calling when we were in the middle of a conversation, she’d had enough and our relationship almost ended.

My biggest behavior change 14 years ago was to focus hard on having my words match my actions, and my actions match my words. Simple to say, really hard to do.

Of course, it also works in a business context. I’ve learned, and deeply believe, that it’s the essence of being authentic. You can have any style you want – these two things just have to match up.

Sadly, many very successful people simply don’t understand or appreciate this. They put huge amounts of energy into developing a public persona. It could be PR, it could be speeches, or writing, or systematic campaigns over a period of time about themselves and their businesses.

But then their words and their actions don’t match up. Over and over again. It can be subtle or overt. It can be mild or jarring. It doesn’t matter – if they haven’t internalized the idea of their words and actions matching up, there is a long negative reputational effect.

And, as our email exchange demonstrates, it lingers. I have heard the same thing about that VC and I’ve experienced it personally. Yet his public persona is “entrepreneur friendly”, “very accessible”, “incredibly smart”, and “highly capable.” Yet, he completely blew you off, after asking you for something when you were a powerful and well-connected executive at a large company. Stupid behavior on his part.

Oh, and in addition, this VC missed a chance to invest in what is now a rocket ship. And the entrepreneur didn’t go back to him for the Series B because he got blown off the first time, so the VC missed two chances to invest.

Do your words match your actions? If you don’t know, ask yourself at the end of each day “did my words today match my actions.”

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Jul 11 2014

Digital Paralysis

I heard a great phrase from Jenna Walker at Artifact Uprising yesterday. We had a Blackstone Entrepreneurs Network Colorado meeting with her and her partner and in the middle of the discussion about their business Jenna used the phrase “digital paralysis” to describe one of the things she thinks is driving the incredible engagement of their customers.

Her example was photography. Artifact Uprising came out of her original experience with photography, the dramatic shift to digital photography on iPhones and picture storage on Dropbox and Instagram, and the massive overwhelming feeling of having zillions of digital photos. In Jenna’s case, it’s caused a slow down of her photo taking (digital paralysis) because she’s overwhelmed with the massive numbers of photos she now has, doesn’t really have the energy to deal with them, and resists taking more because they’ll just end up along with the other zillions in Dropbox.

I totally identified with this. Amy and I have a huge number of digital artifacts at this point – with our enormous photo library being just one of them. The feeling of paralysis in dealing with them is substantial. After a brief tussle the other day over “hey – just share the photo stream with me of the stuff you are going to take today” followed by a struggle to figure out how to do it the way we wanted to do it and still have the photos end up in the same place, tension ensued and digital paralysis once again set it. I sent myself an email task to “spend an hour with the fucking photos on Dropbox” this weekend which I’ll probably end up avoiding dealing with due to digital paralysis.

Yesterday, my friend Dov Seidman wrote a great article in Fast Company titled Why There’s More To Taking A Break Than Just Sitting There. It’s worth a long, slow read in the context of reacting to being overwhelmed digitally as well as in the general intense pace of life today.

As I sat and thumbed through some of the beautiful photo books that Artifact Uprising creates, I could feel my brain slowing down and being less jangly as I settled into observing and interacting with something not-digital. Try it this weekend, and ponder it while you are taking a break. Pause, and explore why you are pausing, how it feels, and what you are doing about it. And see if it impacts your digital paralysis when you end the pause and go back to the computer.

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Jun 6 2014

After Your First Big Success, What’s Next?

As exits have been flowing nicely again the past few years, many of the entrepreneurs I work with have experienced their first big exit. I refer to this moment as when you find that you have life changing money in your bank account, which I like to call “fuck you money.” You now can do whatever you want with the rest of your life.

I was on a walk with an entrepreneur recently who was wrestling with this when we ran into another entrepreneur I had backed who had an exit a while ago and had wrestled with the question of “what’s next.” We chatted briefly and then he hopped on his bike and continued his ride.

Later in the day, I got the following magnificent note in my inbox from my bike-riding successful friend.

I was thinking about the ‘what’s next’ conversation. I’m sure you’ve seen everything and are all over it, but in my more limited experience, for some people it’s harder than the what’s first conversation (i.e. should I start a company or not?).

I find, unfortunately, that a reasonable percentage of people chase their tail endlessly looking for the next big win, but they can never catch it because they have no idea what they are chasing. Their life spirals inward as they get more unsure of themselves, more frustrated, more unhappy.

I think this state of uncertainty and self doubt causes more depression, divorce and addiction for some people than starting and running a company. Especially if they’ve never felt failure before. Now they fail all the time and they can’t figure it out.

I think it’s mostly because they never find passion again, or they look for it in the wrong places. There are a million things they can do in the world, but the spend most of their time looking for the next great technology company that sells a better widget, but doesn’t necessarily change their life in any meaningful way.

They have grand opportunity because they are unbound to do something they truly love. If you love mentoring, mentor, if you love the environment, help it. If you love children, teach them. If you love your family, share with them. Give back to everyone who gave to you on the path to success, and then give more broadly to everyone who seems deserving.

To me, that’s the real grand victory.

Totally brilliant. And so simple.

I had my first exit when I sold my first company (Feld Technologies) at age 28. After the dust settled and I had sold all the stock I’d received, I’d made somewhere between $1m and $2m after tax. When Amy and I talked about “what’s next” when I was 29.5 (about the time I finished working for the company that bought mine) one of the options for consideration was to retire and move to Homer, Alaska. I was making plenty of money consulting and, while I was investing much of the money I made from the sale into new companies as an angel investor, the idea of living in Homer was attractive. We figured we could easily live for the rest of our life on consulting income and what we’d managed to save, even if none of the angel investments I was making turned into anything. When one of them was acquired a few months later and we had another $1m after tax, we realized that we could easily live on $40k / year of cash in Homer, which would last us about 25 years if we made no other income.

We were deeply in the “should we just call it quits and go live a different life conversation.” But at almost 30, I just didn’t feel done, and in many ways I felt that I was just at the beginning of a new journey (which turned out to be true.) So we packed up, moved from Boston to Boulder, and decided to build a life in Colorado, while I continued to invest. This was 1995 and the path from there has been powerful and dramatic. By 1999 I had to ponder “what’s next” again after a number of my angel investments returned more money to me than I ever thought I’d have, and then again in 2002 after getting massively crushed by the collapse of the Internet bubble and losing even more money on paper than I expected I’d make cumulatively in my lifetime.

I’ve been through the “what’s next” discussion with Amy several times, including in 2004 when I doubled down on Mobius Venture Capital (instead of packing it up and calling it quits), in 2006 when we decided to start Techstars and Foundry Group, and again in 2013 after spending six months being extremely depressed.

Each time, I’m adjusted how I spend my life in the way my friend talks about in his final paragraph:

They have grand opportunity because they are unbound to do something they truly love. If you love mentoring, mentor, if you love the environment, help it. If you love children, teach them. If you love your family, share with them. Give back to everyone who gave to you on the path to success, and then give more broadly to everyone who seems deserving.

If you’ve recently had some success, as you go into the weekend, take some time out to ponder how you are you thinking about this. And share if you have any insights!

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