Amy has a birthday coming up. We spent some time this morning talking about her next year. Since the two of us are together all day every day, we also discussed how I’m spending my time over the upcoming year that begins at her birthday.

A few hours later, I stumbled upon Your Life in Weeks on Wait But Why, one of my favorite blogs. The following are the number of weeks (measured in boxes) that a typical 90-year-old human has on this planet.

Think you have all 90 years worth of boxes? Here’s some perspective.

Don’t want to think in weeks? Ok, let’s scope it down to months.

When you look at it this way, there aren’t that many. Go back to the weeks. When you look at the upcoming week, are you happy about how you are spending your time? How about this month (yeah, we are almost halfway through September already.)

Fortunately, Tim (who writes Wait But Why) sells a handy-dandy Life Calendar (by weeks), so you can sit down and sketch your own out thoughts. I just bought several and expect I know what Amy and I will be doing together for some of next Saturday.

Jerry Colonna has written a “must read for everyone on planet earth book” titled Reboot: Leadership and the Art of Growing Up.

Seriously, go buy it right now. I’ll be here when you return.

Regular readers of this blog know that Jerry and I are extremely close friends and have been for 23 years. I first met Jerry when he was beginning his partnership with Fred Wilson at Flatiron Partners. But, I didn’t meet him through Fred. I met him through NetGenesis, a company I was chairman of at the time that had been started by Rajat Bhargava (who we still work with as CEO of JumpCloud), Matt Cutler (who we still work with as CEO of Blocknative). I won’t repeat the story of Brad, Jerry, eShare, and NetGenesis, but it makes me incredibly happy to reflect on 23 years of friendship, which nicely lines up with my 23 official years of marriage to Amy.

If you want to get a feel for Jerry, listen to one of my favorite Reboot podcasts, where we flip the script and I interview Jerry.

Jerry has been on the road promoting the book the past few weeks. Dip into a few of the podcasts and interviews or get a taste on the CNN interview that he did.

Reboot: Leadership and the Art of Growing Up is extraordinary. It’s 100% Jerry, on every page, and is the book he was put on this planet to write.

If you are an entrepreneur, investor, leader, or human being, do yourself a favor and read Reboot: Leadership and the Art of Growing Up. I’m serious – it will change how you think about yourself, leadership, and life.

I was at dinner several weeks ago with Amy and two close friends who are 20 years younger than us. We were talking about what they were currently doing and they categorized their activities as “adding to” or “not adding to” the legend of mike and mary. I’ve anonymized them, but you get the idea.

The legend they were referring to was their internal legend as a couple. Neither of them could give a shit about the external legend, or what the world thought of them. This wasn’t about fame, ego, recognition, or acknowledgment. Fame and fortune didn’t play into the construct.

Instead, it was about their life together. Their journey. What they did together. It was the label for their narrative as a couple against the backdrop of a finite amount of time on this planet. Many of the activities in their legend where individual ones, but supported by the partner. And many others were ones they did together.

It was a beautiful approach. During the conversation, we went deep on the work one of them was doing, which they concluded was not adding to the legend of mike and mary. I got a note the next day that, as a result of the conversation, mike was going to leave his job and pursue something else that was much more important to him and that they thought could add to the legend of mike and mary.

I loved this construct. Since that dinner, Amy and I have used it a few times when talking about something we were considering doing. The question “Does this add to the legend of Amy and Brad?” provokes a different type of conversation about a specific activity or decision, especially when the activity or decision is significant, requires a long time commitment, or takes a lot of energy.

Remember – it’s internal, not external. Assume you write the legend at the end the end of your life but no one else ever reads it. It can be for you as an individual, or as a couple.

The next time you are pondering something, ask yourself the equivalent of “Does this add to the legend of mike and mary?”

I’m a fan of spring break. I’m a believer in regular vacations. I love it when people I work with get away and disconnect. And, I do it at least four times a year.

Spring break feels like it has gotten out of control. Rethinking it could be interesting. This year, at least 50% of the people I work with regularly are on spring break this week. I think the other 50% go on spring break next week. Easter seems to be the pivot point for this.

Unlike the week before Christmas, which moves around every year, if Easter is the pivot point for spring break, life would be better if everyone in the US decided the week before (or after – I don’t care) Easter was spring break. Then, the rhythm of work in the US would slow (or at least change) for that week, just like it does for the week between Christmas and New Years.

And, everyone who goes on spring break with their family and kids could actually disconnect, rather than what I’m observing, where some people disengage, but others keep one foot in, probably ruining the real value of a week-long disconnect from work for them

I’m not at all cranky about this. I’m at work this week – and next week. Amy, on the other hand, is on spring break with a girlfriend who is five years recovered from a serious illness. While I miss her, I’m using the time as an excuse to stay up late watching silly television shows.

While I know a blog post from me isn’t going to affect anything, imagine a world where we had a real, synchronized, completely off spring break in the US. It would be a better world for everyone.

Ted Rheingold just passed away. He was an amazing guy beloved by many. Endlessly joyful, inspiring, and loving.

His autoresponder (typos and all) is one for the books, and like great poetry, worth reading over and over.

My cancer (ccRCC, metastic) has gotten the upper hand and I’ll be
putting all my resources into managing it.

In my stread, please keep these very important messages in place:

* be good to each other

* enjoy evert day

* wanting is suffering

* The journey is still the destination, now more than every

* the trend of purpose is coming like a tidal wave, get out a heard of
it. enjoy the ride. die fulfilled.

* Reframe your thinking of “what your career can do for you,” into
“what can your career do for others,” and wonderful, meaningful work
awaits you.”

Jeff Clavier introduced me to Ted in 2006 and we both invested in Ted’s company Dogster. We crossed paths periodically, usually online.

My last email to Ted was a few months ago, where I wrote “Sending you some love this morning” followed by

He responded quickly with:

Thanks Brad.

Sincerely.

Every day is hard these days.

Nonetheless, I’m very happy to be alive and keep fighting through.

t-

At some level, it’s all pretty simple.

Enjoy Every Day.

Ted – thank you for the gift of you.

I’ve had an emotionally challenging morning so far. I woke up too early and was deeply agitated. I tried to get rolling, couldn’t, and went back to bed. But I wasn’t able to fall asleep and my brain kept cycling on all the political chaos and societal hatred that is going on. I’ve tried to compartmentalize it but it broke through again the last couple of days after Charlottesville.

I got up and realized the Internet was down. I decided to just go running. Two minutes in, Brooks came up lame and I walked him back home. I started again with Cooper but my left knee was a little twingey so I decided to bail and take a few rest days. The Internet was still down.

Amy and I then spent time at breakfast talking about how to reconcile the intolerable. I felt a little better and was helped by Fred Wilson’s post If You Lie Down With Dogs, You Come Up With Fleas and Mark Suster’s post Finding My Tribe — The Upside of the Downcast Year.

I’m off to grind through a massive backlog of email today. I leave you with a beautiful video of the eclipse from 2015.

In June, Amy and I had three friends die. One was a mentor of Amy’s from Wellesley, one was the father of a close friend, and one was the wife of a good friend of over 25 years.

Yesterday, while sitting at my desk between calls, I noticed an email from another friend titled Thank You For The Throne. The email said:

After spending many days visiting my mom in the hospital, I felt the need to thank you for your support of Boulder Community Hospital. I found it hilarious and appropriate that you were the sponsor of the bathroom. So, thanks for the throne and the humor during dark days. She is on the rebound after a brutal fight and back at home doing rehab. Hope you’re well.

I sat there trying to process that. I didn’t know the mom was in the hospital. The mom is a fixture in our community, a long-time friend, and an amazing woman. I responded with:

1. Thanks.

2. OH MY GOSH. WHAT HAPPENED TO XX? IS THERE ANYTHING WE CAN DO TO HELP?

I’m 51, and I have an extensive network. I know this is going to start happening more frequently. In The End, Entropy Always Wins was an effort last week for me to process this a little.

But the email yesterday was a shock. I’m still processing it. I’m thankful our friend is stable and out of the hospital. But it’s just another reminder that our experience on this planet is short and not under our control.

I woke up to an email from a close friend of 25 years that his wife had passed away unexpectedly last night. She’d been fighting cancer for several years, had made progress, then had setbacks, and then made progress again. While I knew them both, I’d spent many hours over the years with my friend, so I immediately felt his sense of loss because I know how central his wife was to his life. I just hugged Amy and sent her out into the world for her day with tears in my eyes the phrase “In the end, entropy always wins.”

Last week, when another close friend died of cancer, Amy said to me “We fight the good fight our whole lives, and then we lose.” It wasn’t meant in a negative way but was an acknowledgment that in the end, we die.

Two other lines that always come to my mind in moments like this are “Life is a process of continuous oxidation” and “Life is a fatal disease.” The second is lodged particularly deep in my brain, as a friend told it to me after his child died at age 21.

While this applies to humans, it applies to everything else. I’ve yet to meet an immortal animal or plant. Many of the Built to Last companies have struggled or failed since Jim Collins wrote his iconic book. Granted, while Rome, which wasn’t built in a day, is still around, the Roman Empire had a finite life.

Companies don’t last forever. Institutions don’t last forever. Physical objects don’t last forever. Our planet won’t last forever. Human civilization won’t last forever.

In the end, entropy always wins. Consider that when you make decisions trying to control the outcome of something.

I’m sitting up in Amy’s office on a beautiful Tuesday morning listening to the Liz Wright station Pandora. Amy is downstairs doing something with the dogs.

I just cried for a few minutes after reading Ted Rheingold’s post As I Lay Dying. When I got to the final section, which he calls “Now,” I read it three times.

“I’ve gained some powerful emotional powers (super powers) in what I’ve been calling my second life. Most all my deep-set hangups died with my first life. A number (but not all) of my grudges, entitled expectations, self-assumed responsibilities, judgements are simply gone. I have no FOMO. There isn’t an event I’ve heard of since I’ve recovered that I wish I would have been at. I’m simply content to be alive and living my life. I have no bucket list. Life is the bucket.”

If you don’t know Ted, he now describes himself as “Beating stage 4 carcinoma thanks to amazing researchers oncologists and immunology. Passion for making the Internet do exciting and wonderful things.” I know him from an angel investment in Dogster, a company he founded and ran from 2003 to 2011 when he sold it to SAY Media. Jeff Clavier introduced us, and I think it was the first investment Jeff and I did together.

I haven’t kept up with Ted other than a periodic email. But whenever I see his name, I think of him fondly. While Dogster was an ok outcome (I think I got a modest return – maybe 2x), Ted worked his butt off, valued his early investors, and was a delight to engage with him. But that doesn’t matter, as it’s not what is important about this thing we call life.

Ted touched me profoundly today with this post. His clarity around his second life is intensely powerful. The statement, “I’m simply content to be alive and living my life.” is something that vibrates in my brain.

Ted is getting a phone call from me to say thank you for putting this out there. And to send him a hug over the phone lines. Ted – thank you for saying “Life IS the bucket …”

For your Sunday video watching, I encourage you to spend ten minutes of your life and watch Chris Moody‘s Commencement Address to the Auburn 2016 graduates.

His message is simple: Work Hard. Be Kind.

Having worked with Chris for many years, it’s a great summary of how he lives his life. And he ends with a magnificent Dalai Lama quote. “Be kind whenever possible. It is always possible.”

Tami Forman, the Executive Director of Path Forward (a new non-profit that I recently joined the board of) just did a powerful five minute presentation on making space for moms in the workforce. I knew that Tami was a great speaker because of my interactions with her at Return Path, but she just totally blew me away with this talk.

Making Space For Moms | Tami Forman | DisruptHR Talks from DisruptHR on Vimeo.

My favorite one liner in the talk is “In the S&P 1500, there are more CEO’s named John than women CEOs.” This is definitely worth five minutes of your life to watch right now.

Paul Kalanithi’s book When Breath Becomes Air is one of the best books I’ve ever read. I stayed up late the past two nights reading it while in bed. As I put my Kindle on the bedside table last night I had tears in my eyes.

Paul passed away on March 9, 2015 at age 37. He was a Stanford-trained neurosurgeon and writer. He was diagnosed with stage IV lung cancer in 2013, though he never smoked. He was married to Lucy (Goddard) Kalanithi who sounds like an amazing woman. When he died he had an infant daughter Cady. His family was extremely close to him.

I know Paul’s brother Jeevan Kalanithi. Jeevan co-founded Sifteo, which we invested in with True Ventures. Sifteo’s products were critically acclaimed but not commercially successful and was acquired by 3D Robotics, which we are also investors in with True Ventures. Jeevan is Chief Product Officer at 3D Robotics and has done an awesome job. And, more importantly, is an amazing person.

So, as I read Paul’s book, while I didn’t know him, I felt like I had a sense of him through knowing Jeevan. I read Paul’s New Yorker Essay My Last Day as a Surgeon which was published after he died. Read it if you want a taste of Paul’s writing, genius, empathy, beauty, and authenticity. Now, imagine an entire book like this. Read his essay Before I Go for another taste. Or try How Long Have I Got Left? which was published in the New York Times a year before he died.

If you haven’t yet bought When Breath Becomes Air, please go do it now. It’s #1 on the New York Times bestseller list for a reason. It might be the most powerful book about being human, being mortal, learning about, confronting, dealing with, and ultimately accepting one’s own mortality. It’s beautifully written – almost poetic in its rhythm – and aggressively real. There is no prognosticating, no rationalizing, no baloney – just real, raw feelings throughout the book.

And it ends suddenly. Paul dies. Unlike so many things that we hear about that are tied up nicely in a bow, life – and death – doesn’t really work this way. And Paul helps us understand this by taking us through his journey.

When I was in my mid 20s, struggling with depression and having paranoid fears about being deathly ill, my therapist recommended I read Norman Cousins book Anatomy of an Illness: As Perceived by the Patient. It changed me fundamentally and shifted my relationship with my own mortality. It didn’t eliminate my depression, but it helped me understand how my viewpoint impacted my physiology, and how important this was in healing.

Paul’s book takes this to a new level. Like Cousins, it’s deeply personal, but by being current, it’s more accessible. And for me, more powerful.

Thank you Paul for writing this book. And thank you to Paul’s family for bringing it into the world.

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.

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.

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!

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.

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.

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.

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?

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.”