Bizotomy: Jon Gaskell, Smartypig.com. A look into an Internet start-up and managing Gen Y

Couple weeks ago I struck up an email conversation with one of the creators of a new banking website. Jon Gaskell saw a need for a financial site that would help people create a goal and save to reach that goal.

With his co-founder, Michael Ferrari, Jon and Mike ventured to fill this void and together they created smartypig.com. Smartypig is unique in that it allows the user to make their goal public. This lets family and friends see your aspirations and goals and even contribute to them!

Even though Jon isn’t Newlycorporate or Gen Y, I have never passed up the opportunity to pick someone’s business brain. Below Jon provides us with some insight into his career, new business, and generation Y.

1) How old were you when you started smartypig?

Mike Ferrari, who is a co-founder with me, and I were both 34 when we first began discussing the idea behind SmartyPig. We developed it for two years and launched it three month ago.

2) What was the biggest challenge you experienced while creating SmartyPig?

Trying to keep a tight hold on our creative license while working with financial institutions and regulatory bodies that made us jump through any number of hoops in order to get to where we are today. The cost of entering the space should be noted, as should the barrier to entry which is nearly impossible.

3) What was the easiest thing about creating a start-up?

Spit-balling and white-boarding. The “What If We Did This” jawboning sessions led to much of what you see today. Truly letting the imagination run wild is easy. It was also easy, at least with this start-up, to attract terrific partners and investors - all of whom have always had our collective back and helped us through some of the more interesting challenges.

4) What would you do differently?

Watch our pennies better. First rule: stay in business. Start-ups fail because they forget the first rule. Like the old saying goes, “It is easier to save a buck than make a buck.” In this world, truer words have never been spoken. Mind you, this is extremely tough to do with a wild imagination.

5) Did you reach your first goal you created on smartypig?

I have reached two goals, and currently have five, including one for holiday gifts next year so my wife won’t have to send our credit cards into overtime (while we struggle to pay bills for months after), as well as a for a family vacation we are planning next winter with my brother and his family. And my wife also wants silverware - not a very exciting goal, but oh well.

6) What is your favorite feature or part about smartypig?

We truly created SmartyPig with the idea of young adults and kids in mind. The idea of teaching the next generation of banking customers that saving can be social and fun is a story I never get tired of telling. With all the bad news out there on the financial services front, we feel like we offer an opportunity for individuals and families to not only get on the right track, but a fun and optimistic way to jump in with both feet first.

7) Where is smartypig going next?

SmartyPig will unveil a new build in he next 30 days that will knock your socks off. We are committed to not only being the only true banking application that is social but being the leader in the space that we call “Bank 2.0″ by talking to the generation that is already online and connecting.

8 ) Do you have an Gen Y employees at smartypig? What is your feeling on the generation in the workplace?

Absolutely. We are for Gen Y, so we would be shortsighted not to have it well-represented in our workplace, as they think like our primary customer base thinks. Also, they can stay up really late and get after it. But they are a little groggy in the morning - unlike those of us (Mike and myself) who have kids under the age of three.

9) What advice do you have for a young Newlycorporate person?

Be a sponge. Listen to everything everyone else is saying, take notes when others are talking, and then really pick your spot when you decide to speak up. Everyone else at the table will take you very seriously when you finally do.

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