Entrepreneur In Tech Though Not By Choice

It’s taken a lot of time to write this story. Partly because I don’t know what I am doing, but mostly because I want to write something that gives others a sense of “what to do next.”  I am in year four.

My journey began in 2012 as a white paper for the American Planning Association (APA), the biggest organization covering how cities and towns are planned in the United States. The white paper began in a journey where a 50 year old woman had trouble finding a job once relocating to Washington D.C.

Luckily I have a good reputation for innovation and good urban planning at the national level. So I completely changed course from mainly public sector servant to private entrepreneur. Here is a short summary of how this unfolded:

1. Can’t find job.
2. Digging into Passion + what I know, write a white paper on planning and building solutions where new density meets the old neighborhood.
3. Realizing this is about urban+architectural innovation
4. Realizing any print resource would be out of date upon publishing
5. Bootstrapping website that got a good amount of recognition and encouragement
6. Launching wildly popular, humorous Kickstarter card game (when the website was not getting traction)
7. Engaging with Kickstarter community to go from fun game to serious city/town building tool
8. Launching wildly unpopular Kickstarter card product + mobile app (and lots of insight from community)
9. Going back to customers to see where we asked the wrong questions.
10. Developing new products on the horizon base on what our community said: we need engagement + print + digital + consulting tools
11. Partnering with transportation firms to test products in real world.

That is what four years look like for a now-54 year old woman hitting the reset button (on everything – but that’s another story). The story-at-hand is one of changing course mid-life and mid-career. Everyone’s story is different, but here is what I have learned from being a startup that might help:

1. It is really hard (and well established) for women to switch gears in one’s 50’s, in particular for older women who stayed at home to raise kids. One former boss noted, off the record, he mainly hires Millennials and marquee names to bring in donor dollars.
2. It is also really hard to switch gears from a career in public service to one in private enterprise. In government jobs, we are taught to make everything widely available for free since taxpayers paid for it. The private sector is the other way around: find value people will pay for and don’t back down.
3. There is no better time to enter the world of entrepreneurship: new models like the Lean Startup, Blue Ocean Strategy, and the new business canvas help re-frame new business ventures. The startup world really helps.
4. That said, starting a business is always hard.  When someone says expect to hear “No” a thousand times, it is real.
5. There is NO substitute for talking to clients, customers and end users.  But it is easy to mis-hear and interpret their comments as what you want to hear, not what your audience really wants.

But if you can crack that – you will both make money and fulfill a need. That’s the story.