My Ginger Rogers Story: How I’ve Danced Backwards and in Heels to Incubate and Accelerate

Written by  //  October 12, 2011  //  Featured Writings  //  No comments

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Re-posted from Forbes.

As an entrepreneur, you spend a lot of your time looking forward and asking: Where are we headed? Do we have enough cash flow and resources to keep moving? What’s the next big thing? Where do we want to be in 18 months?

Every so often, you also get to look back and ask: where have we been? what mistakes have we made and how do we learn and get better from them? what brought about key shifts for us and how can we summon the strength to make even more change happen?

Preparing for Silicon Valley Bank’s Accelerator CEO Summit last week provided me with the opportunity to indulge in this very kind of reflective pause. Along with an Olympian (Linda Jackson), a sommelier (Raymond Nasr), the Deputy CTO of the U.S. (Chris Vein) and dozens of entrepreneurs and industry leaders, I shared a handful of defining moments that have changed the course of our company — and in the process, changed me.

While I normally focus on talking to other women about their experiences, today I wanted to share a few of my own, in hopes of continuing to shape and evolve the discourse around women getting more seats.

Five Defining Moments in JESS3 History

(Please click to view Slideshare presentation)

Defining Moment #1: Dedicating to Excellence and Labs.

From the moment of JESS3’s inception, we made an unrelenting dedication to excellence. This has meant we never ship at 80% and would rather lose money on a project than have it fall short of the highest possible expectations. Our process and precision are as important to our output of excellence as the input from our incredibly talented team members.

Coupled with our dedication to excellence is our commitment to continuous experimentation. The labs mentality permeates our company; coming up with new approaches and collaborating without budget / time / client pressures are what have brought about some of our most monumental outputs: The State of the Internet, The Conversation Prism, The State of Wikipedia, The Geosocial Universe, the Ex-Blocker Plugin, and I Voted. It has also provided us with a platform to do pro bono work and support causes we believe in: Amnesty International, Cause Shift, the BP Oil Plugin, Changing the Ratio on Wikipedia and getting women More Seats. We fund these projects on our own and strongly encourage making this a priority — whether you are an established company, or just starting out.

Defining Moment #2: Narrowing Focus to Data Visualization.

There are hundreds, if not thousands, of creative agencies in the world. Producing excellent work and having a penchant for labs certainly helps break through the clutter, but even then, you are still up against shops that are bigger, more established and better resourced than you are.

Enter: our choice to focus on data visualization.

Inspired by a combination of (a) Edward Tufte seminars, (b) Jesse’s proven track record as a UX and social designer, (c) getting a read on the market through wins with Brian Solis (Conversation Prism v1), APTA (Go Green, Go Public) and C-SPAN (Convention and Debate Hubs), (d) more data being more accessible thanks to social and open APIs and (e) the exponential growth of data online and in our lives… it all came together… and we chose to focus our efforts on information design, visual storytelling and the craft of data visualization.

The landscape for data visualization firms is WAY less crowded and we’ve found it to be more collegial, supportive and collaborative than it is competitive. Outcome: amazing deal flow, recognition and opportunity. Recommendation / learning: focus, focus, focus and specialize, specialize, specialize.

Defining Moment #3: Leaving My Day Job (or Facing Down the “Ginger Rogers Conundrum”).

Since graduating college in 2004, I’ve been a legal assistant’s assistant at two firms (Gleaves Swearingen and Arent Fox), a consultant at Dezenhall Resources, a senior producer and director of new media at The McLaughlin Group and a project manager, communications manager and director of engagement at New Media Strategies. Starting at Dezenhall and while at TMG and NMS, I was also helping JESS3 grow.

So while I was doing excellent work from 9 to 5, advancing rapidly in responsibility, role and salary, I was coming home every night (and working through the weekends) and rallying to then run JESS3’s payroll, communications, proposal writing, finances, account and project management, HR and legal. I did this by myself — with off and on help from a small handful of people, chief among them our now VP of Production and Operations, Becca Colbaugh — from October 2006 to January 2010.

Enter: exhaustion, burn out, conflicts, stress, 100+ hour work weeks, learning and living more in a single day than most experience in a month… for almost four years. I affectionately call this the “Ginger Rogers Conundrum” — that is, having to do all the things others were doing only while trying to do many other things (i.e., backwards and in heels to Fred Astaire’s moves).

In the fall of 2009, I made some important decisions, tested them and went with with my heart by New Year’s day 2010. I doubled down on my longtime relationship with Jesse and JESS3 and have never been more challenged or happier in my life as a result. I can say that with 100% metaphysical certitude, to borrow a phrase from my old boss Dr. John McLaughlin. Recommendation / learning: try to leave your day job sooner if you can to pursue your passion, but also realize that working at other places in a variety of roles will also fill out your skill set to make a real go at doing it on your own.

Defining Moment #4: Hiring a Seasoned Team and More Women.

Part of starting out is being scrappy in every possible way: you charge less, you are understaffed, you hire less experienced team members, you yourself are less experienced and you make up for it with heart, hustle and fortitude.

The main things we truly had an advantage in were (a) the level of excellence in our design and (b) our social + data-driven creativity. We also charged waaaaaay less than anyone else in the market. The rest we failed at… miserably.

We didn’t have enough bodies to do work; we also didn’t have the right bodies. Part of the issue was that because we charged less, we had less to spend on talent that wasn’t critical to design (the inverse issue of most companies, might I add). Which naturally begets the issue of when you hire “A players” in the design space, you leave little to spend on positions that were seen as overhead: project and account management. We also faced the same challenge that every company in our space is challenged by: the talent war for engineers.

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