Pondering Mortality

I celebrated my 43rd birthday this week, but this one was distinctly different – it was my first birthday as a Dad, and it really had me reflecting on the past year and particularly on the future in a very different way than past years.  My typical birthday routine is to enjoy a phenomenal cigar and an even more phenomenal glass of scotch while thinking about the past year and what I hope to achieve in the next year.  While the cigar, scotch and prior year reflections followed a similar routine, my thoughts, objectives and priorities for the future could not be more changed.  There were two key differences this year:

First, its not just about me and what I want to accomplish or what I want to do.  This is probably obvious to you who are parents, the birth of your child and the immediate and complete priority shift and sense of responsibility for their happiness and well-being become the leading priority in life.  But what really struck me and had me reeling (read: panic) a bit was the second stream of contemplation – the realization of my own age and it’s conflict with the longing I have to know my child into his old age.  To experience his adolescence, help him through heartbreak, watch him become the man he chooses to become, rejoice in his marriage and see his world change, just as mine did, when his first child is born and I become a Grandpa.  But wait!  I’m 43.  That means 60 at high school graduation.  What if he marries or decides to have children “late” in life like me.  That’s 86 at first child.  Ugh, you can see how this began to quickly spiral out of control as I began to hyperventilate with the cigar and gulp 19 year old scotch.

Then it hit me.  Quit being an engineer, trying to plan and predict your life and every outcome for those around you.  While we like to avoid thinking about it, let’s face it, there are dozens of causes, accidental or otherwise, for us to “go” at any moment.  Accidental death took my own father when he was just 36 years old (I was 9).  There is no better defense of “live in the moment” than when talking about loving and nurturing your children and breathing in all of the experiences, every day, that they bless us with.  The energy it takes us to worry, plan and predict is energy that can be channeled into our spouses, children, parents, friends and most important, our own happiness.  This is definitely a work in process for me, I’m not so good at it personally or professionally.

So my personal objective for this coming year is to be present for Jack, Renee and the rest of my family while also satisfying my own professional and personal needs.  And when I start stressing about my own mortality, I’ll just hammer out some miles on my bike, which I love, and visualize (but not stress!) being the healthiest Dad at high school graduation, even if 60 years old.

So What’s Next? Part 1: My Search Criteria

Now that the cat is out of the bag on my departure from TrueCar, lot’s of folks have been asking what’s next for me professionally.  So I thought I would share my process and how I’m thinking about what I want to do next in a series of posts.  I actually began this process several months ago, it’s been a challenging journey with emotional highs and lows but has also been rewarding having met some incredible people and re-connected with others.

Bottom line, there are a number of potential paths to take and criteria to examine – company size, role, geography, my risk appetite, work/life balance – and there are pros and cons to each of the many combinations.  The good news for me?  I’m not ready to make a decision and I’m in no hurry.  And I’ve been blessed with a unique opportunity to have a professional transition at the exact time that my child is born and I plan on taking advantage of simply being a dad and staring at my son for a few months.  I’m extremely thankful for that opportunity.

So how am I going about my search for the next big thing?  There are really two high-level components to the process.  First, being clear about my search criteria and second, executing a process for uncovering opportunities and ultimately choosing one.  I’ll talk about the first component in this post – my ideal search criteria.  Important to note that “ideal” implies a willingness to compromise and evaluate tradeoffs, which in turn requires that criteria are ranked in priority importance.  Here are mine, in order:

  1. I’m not going to start my own company from scratch.  So, I’m looking to partner with a Founder or Founding team.
  2. Chemistry with and complementary skills to the Founder(s) is an A-1 priority.  Alignment on strategy, roles, values, culture, team building among others is important.
  3. I have a strict “No Asshole” rule.  Meaning I won’t work for one, I won’t be one and I won’t participate in a culture that rewards being one.  It’s toxic and threatens both morale and productivity.
  4. I’m looking for an early stage, venture-backed business post Series A.  As opposed to a pure garage startup with limited traction and no funding.
  5. I want to build a company with balance – work / life / pursuits.  I have enough experience to know that working 80-hour weeks just because your “supposed to” in a startup is bunk.  A culture of work hard, smart and leaving some juice for personal pursuits is far more productive.  I’m also not suggesting that clocking a 40-hour week is the right answer either.  You work harder in a startup, period.  But balance is possible.
  6. I’m considering four geographies.  Boulder, Austin, Bay Area and Los Angeles.
  7. I don’t care about industry vertical, but…
  8. I want to focus on a huge industry with a large addressable market.  Even better if the industry is fragmented with limited established brands.  But it needs to be a big idea.
  9. I’m targeting CEO roles, but will consider COO roles.  This is really a function of the experience/strengths of the Founder, back to chemistry.
  10. I want to build a company that solves a real problem and helps people in some meaningful way.
So, have I narrowed myself out of sufficient considerable opportunities?  Maybe, but that’s why its important to create and priority rank a list of criteria, so I fully understand the tradeoffs to be made and which of them can be compromised to create a broader set and volume of opportunities.
These are, at a minimum, guideposts for targeting companies, roles and geographies.  In Part 2, I’ll talk about the process of uncovering, narrowing and choosing which roles to pursue.

A Week of Firsts

At 42 years old, I didn’t think so many “first” new experiences could possibly be packed into a single week.  That was before the remarkable experience of childbirth.  Renee and I welcomed our son Jack Robert Taylor into the world last Saturday, July 16.

Look at that hair!

Now that we are a week post-delivery, I thought I would share a few firsts in my life as experienced during the week.  I’m sure there are many more to come!

  • First time experiencing the miracle of childbirth.  And it is a miracle.  I was doing great helping Renee through the birthing process, really holding it together until I saw Jack’s head, then the rest of his body enter our world.  Then I lost it.  Remarkably emotional and never to be forgotten experience.  And made even more special by having my Mom and Aunt join us for the birth.
  • First time driving 20mph in a 30mph zone.  Seriously, I’ve got a bit of a lead foot and can’t remember the last time I drove the speed limit.  The drive from the hospital to our house was terrifying.  It was old lady driving at its best.
  • First time experiencing true sleep deprivation.  Now I’m a guy that needs his beauty sleep and while I’m losing some sleep, I’m actually sleeping like a King compared to Renee who is up constantly feeding.  We’ve worked out a system that in short has made our days highly efficient.  The next step?  Finding some time for each other.
  • First time there’s someone utterly dependent on me for survival.  I’ve become instantly unselfish.  There is no other way now.  It’s cool.
  • First time I felt relieved to the point of giddy by someone else taking a poop.  To be clear, the first few days are tense when the baby is losing weight and is not pooping and so when it finally came it was the best laugh Renee and I had since the birth.  Now we just laugh every time he poops because it sounds like a volcanic eruption and it scares him.  I’m laughing right now thinking about it.
  • First time I put my wife’s appointments on MY calendar.  Everything must be planned and synched between us.  If she can’t take our ESP machine (Eating, Sleeping, Pooping), then I need to care for him.
And finally,
  • First time I realized my life is really different now.  Friday night our neighbors were having a huge, blowout bash and there was a moment when Renee and I were on the couch, she was holding Jack and I was trying to figure out if the explosion I heard was Jack soiling his diaper.  Sticking my nose in his leg opening didn’t do it, so I stuck my finger in his diaper and got a creamy chocolate surprise.  So there I am, baby poo on my finger, looking at Renee and listening to the trance music and revelling next door.  I said, “Well, our lives sure changed overnight, heh?”.  It was good for another gut-busting laugh.
All you parents, what other “firsts” did I miss?

The Need for Rest

Renee and I just finished a weeklong vacation (honeymoon) in Cancun.  It was much needed for both of us and incredibly relaxing and just great for us to have time to connect given our hectic lives.  There was a time when I was terrible about taking time for myself and my family – going multiple years in between any real time off – and I’ll never do it again.

I know there will be those entrepreneurs and early stage veterans who will say that doing early stage work is all consuming and you have to do “whatever it takes” and there simply isn’t the ability to take time off from a startup.

I disagree.  I’ve lived on both sides of this fence and there’s one fundamental truth – there will always be more to do than you can get done.  And I’ve never taken a vacation when the timing was right, it never is.  And I’ve also never taken a vacation where my absence resulted in a catastrophic event for the business.  To the contrary, time off rejuvenates, enhances focus and most important, it’s an explicit pronouncement of your priorities, not just to yourself, but to your family.  I learned my lesson the hard way as a result of all those years without taking time to remind my family of my priorities.

And I’m not suggesting that in a startup you can disappear into the ether for 2 weeks at a time.  When I take vacation, I still check email once per day and respond to any urgent issues.  This frequency still allows me to relax and focus on vacation, not work, for the bulk of my day.  That is simply my personal balance and one that works just fine for Renee too.

I do realize there are exceptions and I also realize that startups require obsessive, compulsive, even paranoid behavior, but not enough of any of these to avoid putting vacation plans on the calendar in advance and not enough to repeatedly cancel vacation time.

So take some time off.  Disconnect if even just a little.  Connect with your family.  It will all be there when you get back.

There’s a great article detailing a well respected VC’s struggle with the same issue “Do More Faster”.

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