Conversation with Donna Fenn on Upstarts

Donna_Fenn It's a small and connected world.

I was researching Gen Y attitudes for a work-related project and came across the book Upstarts!: How GenY Entrepreneurs are Rocking the World of Business and 8 Ways You Can Profit from Their Success (Amazon affiliate link) by Donna Fenn, which looked really interesting.

A couple of weeks later, I had the opportunity to meet Donna face to face at the Digitini party at SxSW.

For those who don't know her, Donna Fenn is an internationally recognized author and journalist who has been writing about entrepreneurship and small business trends for more than 20 years.

In 2005, she wrote Alpha Dogs: How Your Small Business Can Become a Leader of the Pack, which was translated into several languages. She is a contributing editor at Inc. magazine.

Here's a conversation I had recently with Donna about the topic of her new book.


I love the fact that you turn a myth on its head with your book Upstarts: that Generation Y, which has been described by the media as spoiled, entitled, even narcissistic, is proving these notions false.

Instead, you describe how they are starting companies at an unprecedented rate, and their approach to business is unlike anything you’ve seen. What inspired you to write about young entrepreneurs?

Donna: I’ve been writing about entrepreneurship and small business for more than 25 years and a few years ago, I began noticing more people in their 20s starting companies than I had ever seen in my career.

I wanted to know why they were starting businesses, what kinds of companies they were starting, if they were really so different from the companies I had covered in the past. I interviewed over 150 young entrepreneurs and my research confirmed my hunch that this is one of the most entrepreneurial generations in history.

In fact, I’d go so far as to say that in U.S., we are smack in the middle of a youth entrepreneurship revolution.

But just for the record, I think there are plenty of spoiled, entitled, narcissistic people in every generation, including GenY. I’m often amused that these complaints often come from the very people who raised them: Baby Boomers!

What was your process to find these entrepreneurs? Was your discovery research-based, was there a word of mouth component, did they find you as well?

Donna: All of the above. The great thing about being a journalist my age (imagine me mumbling under my breath here) is that I have TONS of sources.

I put the word out that I was looking for entrepreneurs in their twenties and early thirties and my network came through. I also drew on Inc. Magazine’s 30 Coolest Entrepreneurs Under 30 list, and on the Inc. 500/5000 list to find young CEOs.

My wonderful colleagues at the magazine, where I’m a contributing editor, helped enormously. I also started a blog on, a Facebook page, and a Twitter page, and I beefed up my LinkedIn account, so I put the word out via social networking as well.

In that respect, this book was researched entirely differently from my first book, Alpha Dogs: How Your Small Business Can Become a Leader of the Pack. I felt like I was very isolated –- in a book bubble when I was writing Alpha Dogs and in some respects, that was very comforting.

But with Upstarts, I felt that I was constantly interacting with my subjects and allowing them to drive the content. It was a messier process, no doubt, but incredibly satisfying.

One of the eight critical lessons you share in the book is building collaborative tribes. Do you think this is a trait common to all entrepreneurs, or did you find it more pronounced in GenY upstarts?

Donna: I always say that collaboration is the most important theme in the book and yes, I do find it more pronounced among GenY entrepreneurs.

This is a very team-driven generation. They grew up with pee wee soccer, group projects at school, group activities after school, and then they spearheaded the social networking phenomenon so that even when they were alone, they weren’t alone!

So I think that while they are very driven, they are also extraordinarily comfortable in cooperative environments. They aren’t afraid to ask for help they all seem to have mentors and they tend to seek out groups of other young entrepreneurs for networking.

They share their ideas fearlessly; they’ll run the risk of being copied because they feel that if they don’t tell people what they’re doing, they won’t get the advice and counsel they need to be successful.

And, by the way, if an idea is that easily copied, maybe it wasn’t such a great idea after all! It’s a pretty mature attitude, I think.

When I was in high school, I worked in a pizzeria to buy books for school. Although that experience directly with people made me a better marketer and business person, I'm a bit jealous that with technology a young student could develop something like Facebook and make a ton of money by his late teens.

I know it's not just the technology. What drives more young people to become entrepreneurs today?

Donna: There are lots of factors. Remember, they are the first generation to grow up with entrepreneurial role models, like Bill Gates, Steve Jobs, Anita Roddick, Richard Branson. Then, later, people in their own generation, like Mark Zuckerberg, were sending the message that “I’ve got my own company” was the new “I’m in a band.”

Suddenly, being an entrepreneur was incredibly cool. Also, this generation witnessed the death of the lifetime employment contract they saw their parents laid off after years of loyal service. Plus corporate scandals like Enron and WorldCom and most recently the financial meltdown and the recession have made large corporations look less and less attractive.

Suddenly, starting your own company looks a lot less risky. Technology, which you mentioned, plays a huge role in their entrepreneurial aspirations it’s like the air they breathe and it’s cheaper, faster, and more accessible than it’s ever been.

Lastly, there are now vast numbers of entrepreneurship programs at colleges and universities programs that didn’t exist 10 years ago. We take for granted that you can now major in entrepreneurship, but that’s a relatively new development and it’s most certainly helping to plant entrepreneurial seeds in young minds.

Was there a favorite part in writing this book?

Donna: I’ve been enriched immeasurably by all the incredible young entrepreneurs I met on this journey people I know I’ll be in touch with for years to come. Their enthusiasm and their optimism are absolutely infectious.

I think I also understand, better than I ever have, how starting your own company is a truly transformative experience; I’d like to see every grade school child exposed to entrepreneurship education in some way.

From a rather selfish standpoint, I have to say that without the experience of writing Upstarts, my own social media presence would not be what it is I’m pretty proud of my digital footprint these days and I can’t imagine that would be the case if I hadn’t been talking to people in their 20s every day for the past three years.

But I try not to let it go to my head. Every time I start thinking of myself as one of the cool kids, all I have to do is look in the mirror!

If you were to share one word of advice, what would it be?

Donna: Sunscreen.


Thanks to Donna we know have a lot of information we can act upon:

  • there are tremendous advantages to collaboration  the reasons to cooperate outweigh those to openly compete
  • the stories confirm what we've been saying about the knowledge flows and risking being left behind by not participating
  • people buy the reason why you're different, in a way collaboration is leading up to more differentiated companies the human factor, who works there, is a real competitive advantage
  • “I’ve got my own company” is the new “I’m in a band” and it means all kinds of new opportunities for service/product companies
  • enthusiasm and optimism are infectious
  • bring your sunscreen

Catch up with Donna on her blog, on LinkedIn, Twitter, YouTube, and Facebook. Also, for an executive summary of Upstarts!, download the free ChangeThis manifesto.


0 responses to “Conversation with Donna Fenn on Upstarts”

  1. Wow, this is such a fabulously interesting article. I tend to speed read and skip parts of blogs, but not this one, I was totally captivated and inspired by your interesting comments, and I love the close – sunscreen!! As a Baby Boomer, I’ve tended to shy away from the new modern technology, but I’m starting to realise that I need to accept it and use it to move forward and to keep up. Thanks for your great research, I will now check out your book.

  2. Diane:
    Glad you enjoyed meeting Donna Fenn. She’s a very captivating writer and storyteller. I loved learning about these young entrepreneurs and how differently they’re viewing the world or work and its opportunities today.

  3. Great read. But I’m wondering when Donna says that GenY is the first generation to have entrepreneurial role models what she would call great entrepreneurs such as Levi Strauss, Andrew Carnegie, and Ray Croc? Technology certainly lets new entrepreneurs brand themselves faster and more effectively, but the history of capitalism is full of impressive role models. I’d be curious to see a comparison of the current breed of young entrepreneurs to those in the early stages of the Industrial Revolution. Hunger for riches is a strong motivator, especially during unstable economic times. What I’d be curious to know more about, and maybe Donna covers this, is what factors have motivated innovation, beyond money, given the fact our public educational system does not encourage it. I may need to get the book!

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