Curbed.com & the Road Trip that Started it All

My fellow EarlyStagers asked me to write about the early days at Curbed.com.   I struggled with this suggestion since the story of Curbed is not mine alone to tell, and it’s far from complete.  In the end, it all comes back to real estate, used to be our tagline, and the story of the company's founding is no different. 

My first conversation with Lockhart about what-would-become-Curbed took place in his then-beatup SUV on a drive out to the hamptons to look at summer rentals.  Lock had been writing about his neighborhood for years on his eponymous blog and was considering expanding the scope; I was in the midst of buying my first apartment and painfully aware of the lack of hyper-local real estate-y neighborhood news online to help me in my decision-making process.

Someday LTS will tell the tale in full with me, Eliot, Josh, Joey, Amanda and the rest of the team chiming in.  And when we do, I hope this photo makes the playbook. 

In the meantime over a series of posts, I'm calling The Curbed Chronicles, I’ll share a handful of observations from the catbird seat sidecar in the event they may be useful, or at least mildly interesting, to other teams mired in the company creation process.

The first observation is painfully obvious but critical to set the stage:  

1. Start a Company with People You Trust & Admire.  Easy to say.  Harder to do.

The bulk of my professional career, ex-Curbed, involved conducting due diligence on investment funds for endowed institutions and family office-type investors.  While a litany of criteria exists for evaluating an investment; for me, quality, stability and integrity of the management team always tops the list. 

The number one reason why firms blow up is organizational strife.  Unlike ST's first post, I have made no attempt to back this up with statistical evidence but based on my own anecdotal observations through the years I’m comfortable making the claim in this forum. Even if it appears an exogenous event was to blame – such as the collapse of the debt markets – you can usually trace the failure back to an organizational decision made – such as a desire to chase returns – that put the company or fund in the wrong place at the wrong time.

LP fund investments typically have a 10+ year fund life, so you want to be as sure as you can be that you’re getting into bed with the right people because regardless of what the LPA says it’s how the individuals involved act that matters most.    

Today, Curbed's management team consists of four individuals: Lock Steele, Josh Albertson, Eliot Shepard and me.  The composition of this team, along with the caliber of our employees and respect I have for members of our Board drove my decision to join Curbed full-time this year.  But back in the spring of 2004, Curbed for me, meant a chance to work with Lock on a revolutionary idea.

Lock and I met in high school and have been friends for 20 years.  We remain in awe of each other’s talents and brutally aware of each other’s shortcomings.  Much has been written about The Optimist’s Blogger, and rightly so.  He’s one of a kind.

Through the years, we haven't always seen eye to eye. The ability to disagree but remain committed to to a friendship or a goal, through good times and bad is key.  Our disagreements result from the different lenses through which we view the world and having those complementary perspectives is invaluable in building a company whether we're discussing the importance of comments, whom to hire, or which sites to launch next.

Trust plays into every decision we make, big or small.  It is the basis for delegation and is essential (along with a healthy dose of capital) for scaling.  Trust allowed our equity ownership conversation to take about 3 minutes several months after product launch and for both sides to feel good about the outcome.  At various tech meetups these days I hear people struggling to figure out an equitable split with potential co-founders they just met and I cringe at the potential for disaster down the road.  

In the spring of 2004, I wrote an email to Lock telling him I was in as his business partner-in-crime / summer intern, if he'd have me.  Given our shared history, I had no qualms about offering to take on a significant side project in addition to my day job without obvious financial incentive. I didn't know then that Curbed would become a network of 14 sites, and never envisioned it would be my main source of income, but I knew without a shadow of a doubt that Lock and I would still be taking crazy road trips, like our epic no air-conditioning drive through midtown yesterday afternoon in his current-beatup SUV for a last minute business meeting.  Good times.  

Next installment of The Curbed Chronicles: Taking the plunge, or something related with a catchier title...stay tuned.