I seem to be getting this question quite frequently, why would I, Jill Kaplan, being of sound mind and body want to do a startup at this point in my career? As I thought more about this question than I probably did when I first ventured down this road, it made me realize it was the obvious next step in my career and I could argue what took me so long to figure it out. I knew the day would come when my corporate career would be complete for all the usual reasons but until the actual event and a long overdue vacation, I didn’t seriously consider a plan. I would suggest I never put a plan in place, instead I ruled out the obvious options.

First, I was asked to interview for two CMO positions at startups as I was leaving Cisco. Please forgive me for the non-statistically significant sample size, but in both cases I had concerns with the leadership and culture not being conducive to my success. In meetings with other members of the executive team, it became clear, there was not a clear scope of responsibilities and metrics for accountability. I had gone far in the process and had even been interviewed by members of the board. I was challenged by both CEO’s if I had what it took to survive in a startup, given I had lived in the cushy world of corporate American. I also found, to no surprise, if you are a demand centric person, they think they want a brand person and vice a versa. But most telling, as I look back nine months later, neither company has filled the position I was interviewing for. This left me wondering if there was ever a true commitment by the CEO or was he just going through the motions to humor the board after a recent funding round.

Next I considered the path of consulting or growth advisor – as many of my peers have been pursuing this field since leaving corporate life. I went to a few networking events and saw many consultants in action and the first thing I was asking myself, “how would I differentiate and establish myself?” “And would I find this rewarding if I went down this path?” I had a few friends who were already years into this path and what I heard it is a very bumpy and potentially lonely path. I kept thinking how difficult it would be to to build something sustainable – if you are truly successful, you should constantly be working yourself way out of a job. Lastly, knowing how much I enjoyed working with other smart people, I know it would be very different in a consultative engagement than that which I was used to.

Another important variable in this process was my continued engagement with John Toebes. As I was interviewing for the CMO positions, I would ask John to look through their web site and give me an assessment of their technology. I would come to refer to him as my personal CTO. I didn’t want to throw myself into the all-consuming world of a startup unless I had confidence in the technology. During this process, John would mention we should really go and do our own thing and I kept it in the back of my mind. The spark that bought everything together came when I was asked by a VC to work with one of his portfolio firms in building demand. I went to John first and we started to discuss what we would need to help a small firm. After getting data from these startups, it became obvious, they needed to figure out who were their customers, how to best align sales and marketing and ideally; enrich what little information they have with ongoing firmographics to give them the foundation of a true strategic customer database.

During the process, I realized there were three things I truly loved, and launching a startup was the only way I could combine them all together.

1. Work with smart people and nurture young talent.
2. Offer my brand of strong female leadership in an environment where many would suggest there is a major lack of such.
3. I love data, it is my geeky side and helping clients to unlock more value from what information they have, is very exciting to me.

I now find myself nurturing the early stages of Escape Velocity Inc with a presence in my hometown, Burlington, VT and Research Triangle Park, NC. To answer another question, the reason we registered in Vermont was the domain name we had acquired was available and Vermont has a great track record in supporting and launching major companies, Burton, Green Mountain Coffee, Dealer.com; very impressive for a state of just over 600K people! I quickly found the best legal resources within blocks of each other. John has setup a base for our engineering talent in the Triangle where he has great contacts and acknowledge in finding emerging as well as highly experienced programming skill.

Lastly, I am asked what would I like to see for myself and our little startup in the future? It would be to continue to do the things I love. I have a great example in my dad who at the wonderful age of [xx] is doing what he loves. I see it keeps him sharp, active, engaged.

What I wish and work for at Escape Velocity Inc are:
· To continue to develop technologies which makes small data more valuable, impactful for clients.
· I would like to be able to hire more and better compensate our employees. Our young people are already doing some amazing things and I have seen tremendous growth. The irony is, some of our employees are the children of people who use to work with and for me. I can’t offer my former employees the stability and financial rewards to jump ship but I look forward to the day I can. In the meantime, I thank them regularly for sending me their kids, I love them.
· And lastly, I hope I can encourage and mentor more women to pursue leadership positions, we need you!

To answer the question of why I am doing a startup and why you might consider the same? Answer why not, and then go for it!