On Thursday, I was fortunate enough to interview Ann Handley, Chief Content Officer of MarketingProfs and co-author of Content Rules. In this interview, I speak to Ann about her experience and challenges in starting multiple businesses, when to know the right time to sell a business and her reason for writing a book.
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Ann has been cited as the most influential woman in social media and recognized by ForbesWoman as one of the top 20 women bloggers.
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Below is a record of my conversation with Ann:
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How did you get your start and at what age did you realize that writing was your calling?
When I was 7, I scrawled in my diary that I wanted to be a “writter.” The fact that I was 7 and kept a daily diary is telling, as is the notion that I wanted to be a writer before I could even spell the word.
I wrote constantly – to a slew of pen pals, in my diary, to classmates. As a teenager, I entered every writing contest I could – once, I won a camera from a local newspaper for an essay on world peace. In a way, I was an original blogger (if only the technology existed!).
Writing was the only thing I was ever really good at. Eventually, all that led to a career as a journalist and freelance writer and editor. And then the Internet came along…
How did your work at the Boston Globe and other print publications benefit you as you transitioned from print to online writing and blogging?
Print is simply a way of delivering content. Essentially, the experience of working in print is the same as working online – in the sense that both are driven by deadlines, schedules and (of course) good content. The principles of good reporting and writing transcend format, in other words.
At what point in your road through entrepreneurship did you ask yourself, “Uh oh, I think I’m stuck and I’m not quite sure how to navigate this problem” and how did you work through these feelings of self-doubt and uncertainty?
I have those feelings every day – I’m not sure “uncertainty” is ever a feeling any entrepreneur ever shakes. If the outcome is certain… what’s the fun in that? To quote Homer Simpson here: “Trying is the first step toward failure.”
You founded ClickZ, is this correct? I think one of the toughest challenges entrepreneurs face is to know when the right time to sell is for his/her startup. How did you know that early 2000 was the right time to sell ClickZ?
Yes – I co-founded ClickZ in 1997, when the notion of using the Internet for marketing was nascent. At the time, we were only a handful of sources for navigating this new tool for marketing and business…. It was an era of brochure websites and banner ads.
We sold in 2000 to what was then Internet.com. I’d like to say the move was prescient – that it was sheer brilliance on our part.
But in fact it was more providence mixed with dumb luck. We always intended to sell ClickZ, and the company had evolved to that awkward stage that any business owner recognizes as a maturing organization with lots of necessary processes and oversight. For us at the time, that was the point where it was less fun to run. The luck part was in recognizing that point before the bubble burst.
Let’s talk about your book, Content Rules. What served as the impetus for publishing this book in 
late 2010?
As a journalist and editor, I’ve been creating content as a way to build audiences for a long time. I’ve been championing the cause of web content for longer than most – before “Content Marketing” became the sharpest tool in the marketer’s toolkit. In 2000, I was writing about how website publishers need to pay attention to the quality of their content. And that was when blogs were just coming on the scene, and before social media, and well before most businesses were truly embracing the mantra that All Businesses Are Publishers Now.
I consider Content Rules pretty much the only pure marketing book I’m really qualified to write. And its message is one I feel particularly passionate about sharing, because writing a book is a lot of work. So you have to really, really, really care about the subject to take that on!
How have you used this book as a platform to educate individuals and businesses about the power of content in cultivating a following, garnering new customers and ultimately, driving revenue?
What I really love about the book is that it follows a piece of advice David Meerman Scott gave C.C. Chapman and me when we first started writing: Don’t write for the marketers who know you; write for the businesses that don’t. That helped us create a book that resonates in a lot of unexpected places: with church ministers, and rock bands, and political organizers, and PTOs, and pretty much anyone looking to build an audience and ignite a business. So that’s been particularly gratifying. Of course, my marketing community has been incredibly supportive, but it’s been awesome to see so many (unlikely) others embrace it, too.
What’s your top piece of advice for those looking to start a blog or go as far as launching their own online business?
With so many social tools and platforms, it can feel overwhelming to someone just starting out. (A new social tool probably launched since the time you started reading this paragraph!) So just start somewhere – even someplace very narrowly defined.
And realize that creating content is only part of the effort you have to make: You have to be prepared to also do the work of engaging with your audience and amplifying your efforts on social channels. In other words, that marketing thing…
On the flip side, what’s the biggest problem or issues that you see business blogs are running into today?
Too many business blogs aren’t creating content that really engages an audience. In a study that MarketingProfs did last year with the business-to-business marketers in our audience, we found that 90 percent of companies are creating content as part of their marketing. (You can download the report here: http://bit.ly/contentresearch.) But 41 percent told us that their biggest pain – by far – was creating engaging content. Why is that? It’s because too many companies aren’t creating content that has the needs of their prospects and customers in mind. It’s marketing 101, in a way: Businesses want to talk about products, but your prospects want to hear about what the products WILL DO FOR THEM. That sounds simple, I know. But it’s really hard for a lot of companies to do.
What’s next for Ann Handley?
I’m excited about the increasing alignment of art and marketing. I know that sounds high-minded, but it’s really not. I love how incorporating storytelling and visual content (photographs, cartoons, doodles, and so on) into content are upping the game, and how the tools are available to help us connect with customers at a truly emotional level. Which is, after all, a lot like art.
More about Ann:
Cited in Forbes as the most influential woman in Social Media and recognized by ForbesWoman as one of the top 20 women bloggers, Ann Handley is the Chief Content Officer of MarketingProfs, which provides business marketing know-how for more than 420,000 subscribers. She is the co-author of the bestselling book on content marketing Content Rules: How to Create Killer Blogs, Podcasts, Videos, Ebooks, Webinars (and More) That Engage Customers and Ignite Your Business (Wiley, 2011) as well as a monthly columnist for Entrepreneur magazine. Content Rules was just released in paperback in May 2012.
Based in the Boston, Massachusetts, she has been quoted on content and marketing in the Wall Street Journal, Huffington Post, American Express OPEN Forum, Mashable.com and the Boston Globe, among others. She has more than 120,000 followers on Twitter, and is passionate about using social tools to build relationships for organizations and individuals.
Prior to MarketingProfs, Ann was the co-founder of ClickZ, one of the first sources of interactive marketing news and commentary. Prior to that, she spent 12 years as a business editor and writer for both local and national trade and consumer publications.
For more, please visit MarketingProfs.com or her rarely updated but highly entertaining personal site, AnnHandley.com. Follow her on Twitter at http://twitter.com/MarketingProfs.