By Joanne Wilson (Blogger & Angel Investor, Gotham Gal)
Sometimes you wonder why someone didn’t turn the idea of UrbanSitter into a business a long time ago. Technology has given entrepreneurs a platform to take ideas that might have been around for a while the ability to actually build them. So what is the idea? Creating an army of babysitters for parents through direct connections, references and friends. If you have kids and need to find a babysitter for Saturday night, sign up now.

Lynn grew up in San Diego with two parents that were entrepreneurs. Her father is a real estate developer and her mom is a child psychologist who build a line of stress management tools for adults. Lynn moved north to go to Stanford for college. She majored in urban studies.

After graduating, Lynn moved to Chicago to work for LaSalle Partners, a small private real estate development company where she worked in the analyst department. It was 1996. On the side, Lynn found herself spending a fair amount of time doing research helping friends who were graduating to find the right job for them. This was before Hot Jobs and Monster came on to the scene.

Her roommate in Chicago told her about two people in San Francisco who had just launched a company called Bridgepath that was focused on finding jobs for recent graduates. Maybe she should go work with them? She left Chicago and moved to San Francisco and began to work at Bridgepath. It was a great experience working in a true startup out of the back of a computer store. She stayed a few years before starting her own company.

Lynn started a company around commerce. She wanted to launch something give emerging designers a presence. It was a great idea way before its time. It was too expensive to launch those brands. The company was called She had raised money to grow the business but after two years she walked away.

She went to work for the Gap thinking that it might make sense to go into something a bit more stable. At the Gap, Lynn worked in the real estate acquision division. Things were really changing at the Gap then and not only did they open stores, they closed some too. They were looking at the placement of stores like Old Navy being down the street from the Gap. In the end, although an interesting job, working in a large company environment was not a long term career move.

Her next stop was working for a hotel hospitality group. She was randomly reading an article in the San Francisco Chronicle about this company and went on line to read about the CEO. She saw that they were looking for someone who knew real estate and was entrepreneurial. Perfect.

She built 20 hotels while she was there and what was fun is that every hotel was completely different based on where it was based. I Vence they brought in graffiti artists to create something interesting on the walls. Each project had a different twist. She was able to work with the creative, construction and finance people all at the same time. Then the chain sold out and became a national brand so it was time to move on.

Lynn took a step back as she had two twin boys at home. One day, a friend asked her if she could ask her nanny to help her get a babysitter quickly. She trusted Lynns nanny so she trusted that who ever she got to come would be good. Of course trust is the key word here when you are leaving your child with someone. That tiny transaction created the idea for UrbanSitter.

She built a site bringing in a tech partner, a media person and an operator. The site started with 40 parents and 40 sitters in the San Francisco area this past August. They are now up to 1,300 parents and 1,200 sitters.

Think of UrbanSitter as an OpenTable for sitters. Most of the sitters are college age or just recently graduated and this is a great way for them to make money. The sitters are tech saavy so they get the information through texts. They put on the site the times that they are available. Then they tell their friends to sign up to be sitters too.

Parents can see how the babysitters are connected to each other using affiliation programs and star ratings. For instance, parents can see a babysitter that is being used by other parents at their kids school which provides a trust and comfort level. They also have a third party that does background checks but in essence it is the trust that other people have knowing that they have used a sitter and if they liked them then they would be willing to book their friends too.

They are now focusing on Brooklyn and other areas already growing to 100 sitters after one week of launching. They are changing how the transactions are taking place. Many of these sitters use that money for rent and other things. They would prefer if the money back to them through an online transaction so cash isn’t sitting in their pocket when they leave the job. It also gets rid of the weird factor of being paid. So many times parents end up coming home and looking at each other asking who has cash.

The credit card piece helps verify the parents for the sitters too. Not surprising that 95% of their sitters have some type of online payment account they use. People can get promoted within the site too for instance a sitter can say I am available every single Friday night. Parents will eventually pay a transaction fee depending on if they booked the sitter weeks in advance or just the day before.

Brilliant idea. Makes absolute sense. A win win for both the parents and the sitters. Look to San Diego, Seattle, Denver, St. Louis and vacation spots for UrbanSitter soon. Perfect for an urban saavy tech population. I wish this was around when my kids were little.

This post was originally posted at Gotham Gal.

About the guest blogger: Joanne Wilson is an advisor and investor in startups, including Curbed (Eater/Racked), Food52, Red Stamp, Catchafire, DailyWorth, Editd, Ricks Picks, Cacao Pietro, Editions 01, Hot Bread Kitchen,, Gotham Gym, The Moon Group and MOUSE. Her most successful venture is being married to her best friend Fred and raising her three kids, Jessica, Emily and Josh. Joanne blogs under the name Gotham Gal. Follow her on Twitter at @thegothamgal.