Gen Y Entrepreneurs Transform Work, Life, and Business–Interview with Upstarts! Author, Donna Fenn

Striking out on your own, either voluntarily or involuntarily, is becoming a more common experience along an increasingly flexible career path.  And, it turns out entrepreneurship is especially appealing for members of Generation Y.   In her terrific new book, Upstarts – How Gen Y Entrepreneurs Are Rocking the World of Business and 8 Ways You Can Profit from Their Success (McGraw/Hill), Donna Fenn says we all need to pay attention




They were born between 1977 and 1997, and you can call them what you like; I call them entrepreneur generation.  There are approximately 77 million of them, and their sheer numbers, combined with the rate at which they’re starting businesses, will make them a force to be reckoned with…these “Upstarts” are destined to have a profound effect on the economy and specifically on the small-business landscape.”

In a recent interview, I asked Fenn to talk about some of the ways Gen Y entrepreneurs were transforming the future of work, life and career… for all of us:





DF:  This generation is going to have enormous impact on the future of work for all of us, as employers of their own business but also as employees.  They are hardwired for this more flexible and innovative way of operating we know is very important.

Gen Y entrepreneurs are creating the places they want to work. I don’t think they are sitting down and thinking about it.  They are doing it completely intuitively.  It gives you a huge advantage when an approach that is so strategic, important and gives you a competitive advantage in the workplace is something you don’t even have to think twice about.  It’s like the air you breathe.

The things that are important to Gen Y entrepreneurs—again, you have to be so careful when characterizing a whole group, because there are people to whom obviously this doesn’t apply—but by and large they crave flexibility.  For them, work+life is a 24/7 mash up.  There is no clear dividing line. They are the first generation that expects work to be fun and meaningful.  When you say that to a member of Gen Y, their response is, “Duh!”  But to anyone else and the response is “What a concept that I should actually want to go to my job in the morning.”


They want to work with their friends. They want to have relationships at work, and they want to play and have fun.  People might shake their heads, “What a spoiled bunch of kids,” but think about it.  What’s it like when you play games in the middle of the day?  You find out a whole lot about people that you otherwise might not know.  Like who’s trustworthy, or super competitive.   There is value to game playing and it’s a stress reliever at a time when we are working really hard.  To the older generations, there is still this dividing line, “When I am working I’m working.  When I’m playing, I’m playing.”  This generation doesn’t see it that way.

CY:  From the book, it is clear that Gen Y entrepreneurs aren’t rigid about where they work.

DF: They are used to communicating virtually.  If you have teenage kids, then you know that they are constantly connected and communicating all day long without being face to face.  And, for some miraculous reason, it doesn’t seem to impact the intimacy or productiveness of their relationships.   It’s not that they don’t want to be in the same room or that they don’t crave that interaction, but they don’t need to be in the same room.  They are very comfortable operating virtually.


Many companies in the book have virtual offices, including Mental Floss.  One person is in New York, another is in Atlanta and another in Cleveland.  While this situation has its challenges, there are ways to stay connected such as Facebook Chat, iChat, AIM, and Skype.  You can feel like you are present, and you don’t have all of the distractions of the office.

Gen Y entrepreneurs are also very good if they want to take a day off and go to the beach. They will come in on Saturday to finish the project that needs to be done on Monday.

CY: Why don’t Gen Y entrepreneurs have the same fears about flexibility that seem to paralyze others such as, “Someone will abuse it,” and, “The work won’t get done”?


DF:  There is trust involved here.  From an employer perspective, we have to get over the notion that if I can’t see you then you must be goofing off.   Everybody knows if you don’t get results then your job is in jeopardy.  The key here is a clear set of expectations.  What are your goals for this quarter?  What happens if you meet them?  What happens if you don’t?

For Gen Y employees who are working flexibly and virtually, the bias is that they are independent, self-starters.   Just let them go.  Well no.  You can’t expect anyone to thrive in chaos.  They need clear deadlines.  Short term rewards. They need to check in frequently.  They do need feedback.   This is a generation that was over-supervised and that is a valid observation about Gen Y.   And they are social.  They want to work in teams and groups.

Find a way to accommodate these factors.  If you do, you will have a very productive group of employees.  If you don’t, then you will grumble about how spoiled, entitled and lazy they are.  I have heard comments like, “Why should we accommodate this generation?”  Here’s why:  the way Gen Y entrepreneurs and employees seem to thrive in work—the circumstance and environment that seems to make them most productive—are what we all need to be thinking about in this brave new world.


Rethinking the way you treat employees, the flexibility you give them and the “fit” between their work and life is really strategic, not a benefit.   There are 70 to 80 million people in Generation Y.  They are a huge part of the workforce—huge!   They can’t be ignored. 

CY: In my work with companies, I do find a pervasive frustration with Gen Y as being a group that “Doesn’t want to work hard, and requires a lot of hand-holding.”  There are always going to be unmotivated, lazy people in every group; however, when I meet with Gen Y employees in these same companies my sense is that it’s not that they don’t want to work hard.  It’s that they don’t understand why people are working the way they are and they have ideas about how it could be done differently.  What do you see after writing this book?

DF: When something doesn’t make sense to them, they will speak up and question it.  And when you are a supervisor trying to meet a deadline or service a client, that can be a real pain in the neck.   As Bruce Tuglan says, companies must do a better job of “onboarding” this generation.  Sit Gen Y employees down and give them a good orientation about your company.  Tell them why things are done at your company a certain way.  What can be changed, and what can’t because you’ve tried to change it in the past and it just didn’t work.   Let them know that you’ve been at this for awhile and have some important insights into how things need to work.  As long as they know, you won’t be up against as much of the “why are things done this way?”


Give Gen Y the information and they get it.  They are information consumers and gatherers.    They are the need-to-know generation.  Address that up front you are setting everyone up for success.

CY:  Often when the generations are discussed it’s from an adversarial perspective.  What I liked about your book were the examples of how the generations worked together and leveraged each others’ strengths.   Do you think this is a trend and what does it require to succeed?

DF: This is so common.  My feeling is what we are going to see more and more of this inter-generational collaboration as Boomers leave more traditional employment and don’t retire fully.   The Boomers have the experience, especially management experience.  The young people have ideas and the pulse on the market.  Many generations can work together.


The neat thing about Gen Y is that they are not a, “Don’t trust anyone over 30” generation.  The reason for that, I think, is that Gen Y and Boomers are much closer than Boomers were to their parents. Boomers differed drastically from their parents in so many areas—their clothes, their music, their politics, civil rights, sexual revolution, and Vietnam.  There was so much more to argue about.  Today, parents and kids are more on the same wave length.  As a result, there’s openness on the part of Gen Y entrepreneurs to seek people out for advice.  An example is Aaron Patzer, the founder of  Everyone on his management team is older.  He gets that he needs people with more experience around him.  I think it’s going to be interesting to see how these kids manage employees older than they are, and how (or if) older employees let themselves be led by those who are younger.

CY: What are the three things you would like people to take away from reading Upstarts?


  1. Change your preconceptions about Generation Y.  I am a huge fan of Gen Y and I am an even bigger fan after writing this book.
  2. Entrepreneurs of all ages see and learn from the creative, innovative things these young business owners are doing and begin adopt some of their strategies and approaches.  Do business with this generation because there is such huge potential for inter-generational partnerships.
  3. Be inspired by what Gen Y entrepreneurs are doing with social capitalism, and realize how important it is to have the “giving back” mentality from the very start of your business.   It’s good for your employees.  It’s good for your brand. I think it drives revenue, but ultimately it’s about changing the world through business.

CF:  Thank you, Donna!  And thanks to all of your Upstarts!  They’ve inspired me.