Diane Hessan, Start-up Institute, Woman Entrepreneur

imgresLately I have been talking to some amazing women who are on their third career maybe even their fifth.  They have navigated the world of entrepreneurship while raising a family and everything else that life sends our way.  These women have broken the glass ceiling. They aren’t household names but they are so inspiring.  Their stories are helpful roadmaps for the next generation of women.  I know when I am inspired by someone because I continue to think about them for weeks after our conversation.  Diane Hessan who now is the CEO of Start-up Institute, an organization that teaches an immersive education program targeting the jobs that are needed in the companies we are building today is one of those women.

Diane grew up outside of Philly on the wrong side of the tracks.  Her father had a small sewing machine repair shop called Hessans.  Her Mom was a secretary in the local school system.  She grew up watching her father who was amazing at repairing everything but barely charged anyone a dime.  Growing up they really did not have the cash to do anything but she knew nothing else.  Summer camp was the backyard.

She had heard that Boston is where people went to school so Diane decided to go to Tufts.  She was one of the only people who left Pennsylvania to go school and only 10% of her graduating class went on to college.  She fell in love with Boston when she got there.  A city teeming with students.   She was able to go through a full financial aid package.  She used the money wisely.  Diane decided that she really wanted to go to graduate school and was concerned that financial aid would dry up.  It was 1975 and the economy was not exactly booming.  She pushed herself to graduate Tufts in 3 years and then took the rest of the aid and applied it to graduate school at Harvard Business School.  The second year she took out a loan to pay for it.  She also worked doing secretarial work such as typing, short hand and calligraphy.  Anything that could put cash in her pocket.

After graduating from HBS Diane landed a job at General Mills.  She worked in the Maxwell House division doing brand management for a year and a half.  The company was located in White Plains and then it was time to get back to Boston and get married.  In Boston she landed a job at Gillette.  Two weeks before she began the job the guy who headed up the personal care category wanted to meet her.  At the end of the conversation he asked her if he she had any trepidation about working at Gillette.  Her answer was it isn’t exactly the Peace Corps.  The next day Gillette withdrew their offer.

Diane realized that she really did want to wake up in the morning and care about what she was doing.  Although disappointing certainly an eye opener.  Instead she went to work in consulting.  She knew she loved working with super bright people.  She spent three years doing this.  A few things came out of this.  It was her first experience managing people.  She was good at giving advice but really wanted to get her hands dirty.  She wanted to do the work.  One night she was the office around 8pm.  She was walking down the hall getting coffee and the CEO passes her in the hallway.  She says hi to him.  He hesitates and then says hi and she realizes that he has no idea who she is.  It was that moment where she thought if I ever start my own company I will remember everyone who works for me and create a completely different environment.

Diane left to go to work at the Forum Corporation where she did sales training.  There were only 40 people when she started there.  The company was crushing it and being involved in a training organization was empowering.  Your learn how to manage people, how to speak in front of audiences and how to create transformable experiences.  Every year she had a different job.  She did turn-arounds, created alliances, opened International offices.  As Diane said, she learned how to sell which is the most important skill set in life.  She stayed 18 years until they sold the company to Pearson.  She helped them through the transition and told the CEO it was time for her to move on.

It was the late 90’s.  The internet was taking off.  Diane realized that there are two kinds of entrepreneurs.  There are the ones that love to build and create something of value and sell it.  They are serial entrepreneurs.  Then there are the entrepreneurs who want to build a company that they want to work at.  They are life style entrepreneurs.  She considers herself the latter.  She would lie in her bed at night thinking about building an enterprise business that could make a dent in the universe.

It was the beginning of 2000 and Diane started Communispace.  A typical start-up story. She had an idea around building collaborative software.  She hired developers and raised $12m.  Hired the team with the money.  Listened to her clients to do things differently. Then the internet businesses burst.  The company had issues as they all do and it was time to rethink everything quickly.  Their software evolved into being a disruptive product for focus groups.  They began to build online communities that were proprietary for each of their clients.   It was an asset the companies used daily.  They sold to OmniComm in 2011.  At this point the company was huge and she was thrilled.  They had over 250 clients in twelve countries.  Nobody even left after they sold because she had built a strong culture.

About a year ago Diane was being interviewed for a panel in Boston.  The moderator asked her what was the biggest mistake she had made in her career.  She says the biggest mistake was staying at one company for 18 years because she loved the people and the company.  She could have had three different jobs in that time.  It was an aha moment.  She thought to herself I am doing this again.  I built Communispace and sold it yet I have been there now 13 years with no exit plan.  It was right then that she decided it was time to leave.

Diane had built an incredible team.  She realized by her moving on that they would also rise to another level.  It would be good for everyone.  She stepped aside and became Chairwoman.  She was going to spend the next year figuring out what would come next.  She wanted to take her time.  She did not want to start something again, she did not want to get involved in a non-profit and wasn’t sure about going into run a start-up that needed some adult supervision.  A friend told her that Start-up Institute was looking for someone to come in and run the organization.  She turned it down.

Two weeks later Diane is having a drink with a friend who just had an exit with a bio-tech company.  She tells her about the opportunity at Start-up Institute.  Her friend thinks it sounds amazing.  Diane gets in her car to go home and realizes she should not have turned them down.  She went back to Start-up Institute and tells them that she wants the job after telling her friend she changed her mind.

Diane is now running a next generation educational company.  It is a start-up.  She doubts that she will stay 18 years.  The company is an 8 week boot camp to help people restart their careers.  They can be 20 (chose the wrong career) or 50 years of age (time to shift).  The price is $5k for the program.  You have four options when you go.  You begin by picking a technical track.  Either web development, sales, marketing or web design.  90% of the people that graduate get jobs.  There is a lawyer who moved into green tech and an artist now running a media company.  They are in 5 cities:  Boston, Berlin, Chicago, NYC and London.  People love the experience of the program.  They are learning real life skills for the type of skills needed in companies today.  Why go get a MBA for $150K when this program can open your eyes to a whole different world.  Here you are going to learn about marketing and customer acquisition tools that is needed to go work in a start-up.  This program is based around the world changing.  Really smart.

Through out all of this Diane raised two daughters who are in their late 20s, has a great husband as her partner and an incredible executive assistant and she can’t forget the nannies that helped earlier on.  I love her story.  She has great energy which has been the key to each career step that she has made.  My bet is that the majority of people who worked for Diane adore her, learned from her and felt great about coming into work everyday.  Now if we could package Diane…

Comments (Archived):

  1. Jill

    Thanks for this post. I could use more of these stories about entrepreneurial women with families figuring it all out. Appreciate the inspiration and learning about Start-Up Institute.

    1. Gotham Gal

      I’m a bit obsessed with Startup Institute.

  2. LE

    Wow. This is a great story about Diane and the idea of Startup Institute is fantastic.

  3. LE

    Why go get a MBA for $150K when this program can open your eyes to a whole different world. Here you are going to learn about marketing and customer acquisition tools that is needed to go work in a start-up. This program is based around the world changing. Really smart.Agree. And I think it also shows a great deal about someone’s character when they actually takes the initiative to make a life change rather than just bemoaning how they are unhappy with where they are at.Diane is lucky in one sense. She grew around Lansdale (I’m guessing) and as a result of not having money and being in a boring place (I’ve been there … I had a college job near the borough) there was enough of a contrast between what she thought she deserved and could achieve and what she had in that small town to motivate her to leave. [1]Had she grown up somewhere else (and had been more “comfortable”) who knows whether her life would have turned out the same.[1] In a way, similar to how some people from the mid west travel to LA and NYC and some just stay there their entire lives.

  4. Amy Millman

    No longer a secret – Diane truly is a household name and has been in our home. Springboard Alumna

  5. Sebastien Latapie

    Another great read about an incredible individual – love these posts.

  6. karen_e

    Thank you, Joanne. I have met Diane twice here in Boston (once at the dearly departed Hammersley’s Bistro) and am so glad to learn more of her story.

    1. Gotham Gal

      She’s pretty amazing