Aching for Something New

I had dinner last night with Chris Baggott, one of ExactTarget’s co-founders, and the founder of Compendium, and Bill McClosky, founder of eDataSource and Only Influencers.  The war stories of these two entrepreneurs from the digital marketing space as they took risks, built companies, and followed their passions was inspiring and humbling.

Chris told a story about his son, who commented on Chris’ constant search for creation and disruption of the status quo by saying “Dad, you always ache for something new.”

It hit me like a ton of bricks.  It’s exactly the way I’ve felt my entire life…  this (good) ache internally for newness, for creation, for problem solving.  This longing.  This muse.  It’s certainly what drove me start BuzzBox (an idea which failed miserably!) and then Windsor Circle (which is celebrating several milestones right now!).

My wife would tell you that the list is extensive, and ever growing (and thanks to Laurie for enduring all of the endless exploration of  ideas that will certainly change the world!).  Most of the ideas will never see the light of day.  But some will.  And maybe, just maybe, they will make something new and interesting in the world.

So, when the scotch arrived after a nice dinner last night, the toast went up among this table of entrepreneurs (which I felt a little humbled to be among): “Here’s to Aching for Something New.”

Yes.  “To aching for something new.”  Cheers.

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Conceptualizing the Tunnel and Pushing Through

Laurie (super star wife) and I were reading a little book called “Good Busy” this weekend.  The author, Julia O’Grady, introduced a concept that fit well into the experience of starting a company.  She shared that when people find themselves in unusually tough circumstances (death of a family member, struggling with an illness, etc.) that it is helpful to conceptualize driving through a tunnel.

Normally, you’re zooming along the highway, blue sky and wind, and freedom to go where you want.  Speed up, slow down, change lanes, pull over…  do whatever feels good.

But when you enter a tunnel, things change.  Your options are severely limited.  You have to do what others are doing.  It’s dark and claustrophobic.  Thoughts of being stuck and perishing in the tunnel pop into your mind and cause anxiety.  There is very rarely any ability to turn around and go back…  once you’re in, you’re in.

That said, if you’re reading this post, you’ve probably made it through all of the tunnels you’ve entered.  That familiar “light at the end of the tunnel” shows up at some point, and you breathe your first sigh of relief.  You make it out and you’re renewed…  blue skies again.  The lesson is that tunnels feel constraining, risky, and uncomfortable when you are in them, but that they almost always pass.  By recognizing that the constraints are temporary, you can set your mind at ease, do what it takes to get through the tunnel and pop through on the other side.

The startup life is very much about going into a tunnel.  You’re committed in ways that don’t occur in other career choices.  You’re constrained financially.  There’s a lot of obscurity… who knows when or how this will end.  Your family is along for the ride. Things like college savings and home renovations all go on hold. Vacations are more basic, eating out is coupon-driven, and gifts shift to that which you can find on sale.

Recognizing the experience for what it is… temporary…  is comforting.  The tunnel won’t last forever.  The familiar light will appear again.  The blue skies are ahead.

And… just maybe…  there are rewards on the other end of the tunnel that add a little something extra for those with the courage to persevere!

Extraverts: Talk Think Talk, Introverts: Think Talk Think

One of our investors and mentors, John Fahlberg, is a retired executive who’s built and managed several companies, and has held executive posts with Target.  Net: this guy’s got some time in the saddle.

He does executive coaching these days to keep active, and we’ve been fortunate to have him run several sessions with our team.

We did a standard Myers Briggs personality inventory early in our development, and he coached us through thinking about how to use the results to build a really strong team.

Extraverts: Talk – Think – Talk

One of the core concepts that he coaches us on was that extraverts (yours truly) often process ideas out loud and watch for cues from their colleagues that the ideas have or lack merit, and iterate accordingly.  In other words, extraverts talk about a concept, watch for reactions, think about what they saw, and then talk more to iterate.  It’s a very social process.

Introverts: Think – Talk – Think

Introverts, on the other hand, do that same processing internally.  They think long and hard, using their intellect and their research to derive a conclusion.  They think, then they share what they’ve thought about, and then they think some more based on the results.

Marrying the Two Styles for Strong Outcomes

Cue the obvious observation….  Most technical types are introverts.  Many sales and business types are extraverts.  There’s huge potential for miscommunication and stress.

When I (an extreme extravert), am working through a problem, I start brainstorming out loud to socially engage my team and find an answer.  Chris, my CTO (an extreme introvert) is used to putting a lot of deep thought into something before communicating, so when he hears me list out several ideas, he assumes that I’ve already done a ton of diligence and am proposing a concrete list that we need to act on.

Clearly, this can cause friction.  The extravert can’t believe that someone could work on an important concept without engaging deeply with the group to find an answer together.  The introvert can’t believe that someone could put ideas on a board that haven’t been vetted deeply before being communicated.

What John taught us was for me to literally invoke the phrase “Talk Think Talk” to signal the beginning of a socialized thought process, and to give Chris room to breathe so that he doesn’t interpret the long and rapidly changing list of ideas as items that must be wedged into the development calendar.

This has unlocked a ton of power because it marries the strengths of the socialized creative process with the power of the rigorous scientific development process.  While Chris and I are about as opposite as you can be on the introvert – extravert scale,  this mechanism has allowed our proclivities to complement one another and build on each others’ strengths.  It helps that we have a lot of common ground in our personal values and perspectives on building Windsor Circle, but we’re thankful for a technique that has unlocked a lot of great collaboration.

Thanks John!