one question

One Question for Maira Kalman by Anne Kreamer

Maira Kalman has worked as a designer, author, illustrator and artist for more than thirty years without formal training. Her work is a narrative journal of her life and all its absurdities. She has written and illustrated thirteen children's books, is a frequent contributor to The New Yorker Magazine and the creator of an illustrated column for The New Yorker that morphed out of her travels to museums and libraries.

Q: What’s the most significant risk you’ve taken professionally?

Maira: i never think of any project as being risky. i have an idea and then decide to go ahead. later on i realize that i am incredibly anxious that it be something wonderful. knowing that it could be a mess, or a bore. collaborating is also risky i suppose. it is very very hard to be completely honest. brutally honest with another person. of course there has to be love and mutual admiration, (though they are not always apparent), otherwise it won't work so well. if you find a smart person that you can be absolutely honest with and who is absolutely honest with you, hold on to him or her for dear life.

Maira and Max

Maira and Max

Trust Your Gut When Founding A Company by Anne Kreamer

This piece first appeared on Quartz. In 1996, Carley Roney and her husband David Liu, launched a wedding site called The Knot. Creating a wedding information business was not an obvious next step for the couple, who met while attending New York University film school.

Today, it is the premiere wedding site. The metrics are frankly astonishing. Each year, roughly two million marriage licenses are issued in the US—and each year about 1.8 million “wedding events” are registered on The Knot’s database. According to ComScore, The Knot receives five million unique visits a month, more than the next four wedding sites combined. That means 80% of American couples (predominantly brides) planning a wedding visit the site.

But serving this kind of massive female audience wasn’t an obvious internet play at the time Roney and Liu conceived of the business. “The internet was brand new,” says Roney, “and it was all men in those days—sports stats, computer message boards, etc.—so launching anything women-oriented was a stretch.”

Roney and Liu told Quartz about the biggest professional risks they’ve taken. For Roney, it was committing to The Knot as a brand, for Liu, an acquisition the company made shortly after its IPO.

The following has been edited for clarity:

Roney: In hindsight, it seems like a brilliant brand decision, but in 1996, naming our “new way to plan a wedding,” The Knot, was just a risky move made by an amateur. I literally pulled this idea out of thin air. Cool name for the service that will solve all your wedding problems and be different, modern, and fun? The Knot, like “tying the knot.” Simple. It became the first of hundreds on a whiteboard. I had absolutely no experience in branding, but it was the only name I believed in. Not everyone agreed. I had no budget for a focus group, but the informal research I did attempt garnered mixed responses, at best.

“The what? Not? Not what? Oh, with a K. Knot. Oh, OK. Yeah.” Not exactly a homerun. The silent k. The awkward idiomatic reference. Our founding investors at AOL were so against the choice that they held our wire transfer hostage in the hopes we’d change our mind. (They preferred the more literal “Weddings Online”—better for search, they begged.) But I held my breath, dug in my heels, and promised my partners it was perfect. We were headed beyond the internet, and it was the only name that would both differentiate us from all the tired bridal clutter and work when we wanted to brand books, magazines, TV, etc.

This quirky name, with all its faults, could have been the death of us in a search and data-driven world, but it is considered by many to be one of the secrets to our success. It worked. Once people heard it (plus the explanation of course, “…As in Tying the Knot…”) they didn’t forget it, and wanted to tell someone else about it. Eight of 10 couples in America now use our service, and this marketshare was won almost exclusively by word of mouth.

Liu: One of the biggest risks I’ve taken was an acquisition we made right after our IPO. We went public in December 1999 and we were one of the last consumer internet businesses to get out. It was the first internet bubble so we were not profitable with very little revenue, but we managed to get a $150 million valuation and raised $35 million. Most dotcoms back then used their IPO proceeds to feed the beast by either buying traffic or spending breathtaking amounts on advertising. Super Bowl ads were very much in vogue with the newly IPOed dotcom set.

Instead, we used a big chunk of our cash to buy a 12-year-old, money-losing, local magazine business [Weddingpages] in Omaha, Nebraska. I think what made it so risky was that it was universally frowned upon. The equity analysts who covered our stock could not believe we would jeopardize our pure-play digital media multiple by introducing into the mix, a low-margin traditional publishing business—that was losing money to boot.

I remember shareholders would post on the Yahoo Finance message-boards under our stock quote and accuse me of smoking crack. Internally, the difficulty in integrating the business was absurd. I remember the first big meeting post-closing was assembling the 60 local sales people and giving them laptops and our co-founder walking everyone through the steps on how to turn the machines on. Later, when I gave my speech to the group about my belief that one day, the internet advertising they would sell would exceed the print sales, I remember you could hear a pin drop in the room. Most of the salespeople thought I’d lost my mind because back then they gave the internet away for free as value add to sell the print. It was a hard three years, but we were able to generate enough cashflow in three years to pay back the purchase price. Today, our local business accounts for over 70% of the total revenue of our company.

One Question For David Carr by Anne Kreamer

In memoriam for my friend, David Carr, who died yesterday. We talked about work and risk in 2012. David was a media and culture columnist for The New York Times. In his 2008 memoir, The Night of the Gun, he detailed his past experiences with addiction and includes interviews with people from his past, tackling his memoir as if he were reporting on himself.


Q: What’s the most significant risk you’ve taken professionally?

David:  Back when my twins were getting ready for college, it was clear that we had not done the financial footwork to help them with the terrifying costs. I decided it might help  to do a memoir based on a personal history of addiction that involved some remarkably unsavory behavior. The book, The Night of the Gun, attempted to advance the genre of junkie memoir by reporting out my memories by doing video-taped interviews and digging into medical and legal records. It was, in retrospect, a very satisfying journalistic and literary endeavor, something that I felt good about. But given that I work at the New York Times, it's portrait of a narcissistic and occasionally brutal man who eventually sobered up and gained custody of his children presented some, um, optical issues. Specifically, what would my bosses think of not only the book I had done, but the things that I had done? I can remember when a draft was finished, I went to my boss at the time, Sam Sifton, and he said he would walk it down to the editors, but gently suggested it might be better if I was the one who delivered the manuscript. He was right, but I felt like putting on oven mitts or grabbing a pair of tongs to hand it off. As it turned out, Bill Keller, the editor of the Times, thought the book was just fine. Probably not exactly his cup, but as he said at the time -- and I am paraphrasing -- "We don't hire nuns. The work you did is carefully reported and reflects the standards that we have here at the paper." I was and am proud of the book and if it means that every once in a while someone who doesn't like me or my work dismisses me as a crackhead, I'm OK with that. As Whitman suggested, we all contain multitudes, and that history is part of who I am. But I am also a respected person in my business, a decent father and husband, and someone who works on my own recovery and tries to help others when I can. I proceed through life with my worst secrets already manifest, and there is something to be said for that.

One Question for Jane Pauley by Anne Kreamer

Jane Pauley was the co-host, with Tom Brokaw and later Bryant Gumbal, of NBC's The Today Show from 1976 to 1989. She went on to host Real Life with Jane Pauley and to serve as the deputy anchor for NBC Nightly News.   In 2004,  the year she hosted her syndicated talk show, The Jane Pauley  Show, that she went public with her struggles with bipolar disorder. Your Life Calling: Reimagining The Rest Of Your Lifeis her newest book.  

Q: What’s the most significant risk you’ve taken professionally?

Jane:  Put professional risk-taking in context.  I never expected to have the career I had.  Today Show at 25?  There's a story there. Also when I left 13 years later.   And 13 years after that - when I left DATELINE.   That event was more unambiguously voluntary so TV Guide called me "the poster child for Second Acts"  and Barbara Walters called to ask (as many did) 'why walk away from a prime time show?"

My answer was that I simply felt there was more for me, but I wouldn't know what it was until the TV camera got out of the way and  I said I understood that 'more' would likely mean 'less'. The irony was that all the attention I got about leaving made me more valuable to NBC - so I was quietly offered a daytime show.  This was definitely more not less.  And there was the TV camera again!

But it was a different kind of TV than I'd ever done.  A live audience. Women (mostly).  A conversation. I was intrigued. But scared, too. I'd always worked with a partner if not an ensemble.  This would be just me.

I was dithering over this decision even while DATELINE was preparing a special  'Jane Pauley Signs Off.'   Michael J Fox was my final DATELINE interview.   I asked him a long question about how even with Parkinson's he still did so much- a new book, a TV pilot, a 4th child and raised $17 Million for Parkinson's research - in just the last year!

"If it was me"  I said, "I'd be relaxing, conserving my energy."

His response:  "And what would you be conserving your energy for?" It resonated so powerfully.  And I think that was the precise moment I decided to say "yes."

Going up against Oprah, I warned my kids that this was a long-shot, but that I defined 'success' as having the courage to try

Remember the year Oprah gave everyone in her studio audience a new car?   That was the week my show debuted.  Within weeks it was obvious it was not going to be a success under any but the above-stated terms.

The show was canceled after one season.  It was the hardest year of my professional life.  And the best. I'm proud of the shows we did (one critique:  it was too much like NPR). But we had fun, too.

I have a poster from The Jane Pauley Show prominently displayed in my home office.  My psyche seems not to know it was a failure.  That younger woman in the picture inspires me, because she had the courage to say 'yes'.

One Question For Tory Burch by Anne Kreamer

Tory Burch began her business in 2004 with a small boutique in Manhattan’s Nolita neighborhood, and since then the brand has grown into a global business with more than 100 freestanding stores, and a presence in more than 1,000 department and specialty stores. She's been recognized with numerous awards, including the CFDA for Accessory Designer of the Year, Glamour’s Women of the Year, Forbes’s Most Powerful Women in the World and Vanity Fair’s International Best-Dressed List. A dedicated philanthropist, Tory launched the Tory Burch Foundation in 2009 to support the economic empowerment of women entrepreneurs and their families in the U.S. Through loans, mentorship and entrepreneurial education, the foundation invests in the success and sustainability of women-owned small businesses.

Q: What’s the most significant risk you’ve taken professionally?

The biggest professional risk I’ve ever taken was starting a business. The concept was for beautifully designed, well-made pieces that didn’t cost a fortune. I had worked in the fashion industry for many years in marketing and PR, but I had never been a designer or a CEO. I had to learn on the job.

I was 36 years old and was taking some time off to be with my three young boys. I began putting together image books—sketches and photographs of my parents whose effortless elegance embodied the concept. I started working out of my apartment with a small team and traveled often to Hong Kong, where we set up a sourcing and production office.

When we needed to raise capital to get the company off the ground, I approached family and friends. It was exciting and stressful at the same time. I told people I only wanted them to invest if they were prepared to lose their money. I was willing to bet on myself but bringing in other people raised the stakes and I didn’t want anyone to be disappointed.

With the capital we raised and a personal investment, we were able to open a retail store and launch our ecommerce site. There were many naysayers, and I didn’t take what they said to heart. It was a challenge but I didn’t second-guess myself. The experience made me realize I was an ambitious person and with that was a willingness to take risks.

One Question For Seth Godin by Anne Kreamer

SETH GODIN has written fourteen books that have been translated into more than thirty languages. Every one has been a bestseller. He writes about the post-industrial revolution, the way ideas spread, marketing, quitting, leadership and most of all, changing everything. American Way Magazine calls him, "America's Greatest Marketer," and his blog is perhaps the most popular in the world written by a single individual. His latest book, We Are All Weird, calls for end of mass and for the beginning of offering people more choices, more interests and giving them more authority to operate in ways that reflect their own unique values, and Seth once again breaks the traditional publishing model by releasing it through The Domino Project. His recent Kickstarter for his newest book (The Icarus Deception out in January 2013) broke records for its size and the speed that it reached its goal.

As an entrepreneur, he has founded dozens of companies, most of which failed. Yoyodyne, his first internet company, was funded by Flatiron and Softbank and acquired by Yahoo! in 1998. It pioneered the use of ethical direct mail online, something Seth calls Permission Marketing. He was VP of Direct Marketing at Yahoo! for a year.

His latest company,, is ranked among the top 125 sites in the US (by traffic) by Quantcast. It allows anyone (even you) to build a page about any topic you're passionate about. The site raises money for charity and pays royalties to its million plus members.


Q: What’s the most significant risk you’ve taken professionally?

It's easy for this to become a semantic exercise (what means significant, what means risk) but for me, it was choosing to fire my company's biggest client.

At the time, I had about six employees, we were a book packager creating and selling and building book ideas, and our biggest client accounted for more than half our revenue. It was early days, the first year that I felt we might not fold at any moment.

The problem was that they ceased acting like our partner the day I ended up selling a multi-title book project for them. They thought that the project had gotten too big to share, so they became difficult. It was an organization that was already good at being difficult, one that brought a sharp pencil and little humanity to every interaction. After many months, it was clear that if we kept working with them, we would become an organization that was good at dealing with difficult clients. If we could survive this, the thinking went, then we could survive anyone.

The thing is, I didn't want to become an organization good at dealing with difficult clients.

So we gave them the project, here, take it, and we walked away, taking a huge financial loss. It was crazy.

The good news is that we were energized by our freedom and the lack of finger pointing and nastiness, and made back the lost business in less than two months.


One Question for Gretchen Rubin by Anne Kreamer

Gretchen Rubin is the author of the #1 New York Times and international bestseller The Happiness Project—an account of the year she spent test-driving the wisdom of the ages, the current scientific studies, and the lessons from popular culture about how to be happier. On her popular blog, The Happiness Project, she reports on her daily adventures in the pursuit of happiness.  Happier at Home:  Kiss More, Jump More, Abandon a Project, Read Samuel Johnson, and My Other Experiments in the Practice of Everyday Lifewas published in September, 2012.


Q: What’s the most significant risk you’ve taken professionally?

Gretchen:   My most significant risk professionally was to switch from law to writing. I was clerking for Justice Sandra Day O’Connor when I finally acknowledged to myself that I really wanted to be a writer. I decided to start all over from zero. It was difficult, but I realized that I would rather fail as a writer than succeed as a lawyer. At the time, I was working on a big research project about power, money, fame, and sex, in my free time, so I decided that it was time to treat that project as my job, not my hobby, and see if I could get an agent and sell the proposal for a book. I did—and that project became my first book, POWER MONEY FAME SEX: A USER’S GUIDE. And I’ve been a full-time writer ever since.

One Question For Po Bronson and Ashley Merryman by Anne Kreamer

Collaborators, Po Bronson & Ashley Merryman

Po Bronson and Ashley Merryman are the authors of the new book, Top Dog: The Science of Winning and Losing (Twelve/Hachette). Their previous book, NurtureShock: New Thinking About Children (also published by Twelve) was on the New York Times bestseller list for more than six months and an Amazon Top Nonfiction 100 book for over a year. NurtureShock was on over 35 "Year's Best" lists and is currently being translated in 16 languages. They have written cover stories for Newsweek and New York, as well as features for the New York Times Magazine, the Guardian, the Daily Beast, and others.

Reporting on the science of human development, Bronson and Merryman have won nine national awards for their writing including: the PEN Center USA Literary Award for Journalism; the American Association for the Advancement of Science (AAAS) Award for Science Journalism; an “Audie” from the Audio Publishers Association; and two Clarion Awards.

Prior to their collaboration, Bronson authored five books, including What Should I Do with My Life?, a #1 New York Times bestseller with more than ten months on the list. Merryman's journalism has also appeared in TimeThe Washington Post, and many other venues.

Q: What’s the most significant risk you’ve taken professionally?

Po:  By the summer of 1999, I had been covering Silicon Valley for four years and had reached a certain prominence. My second book about it was on the bestseller lists, my face was front and center on the cover of Wired magazine, I had a big feature in the Times magazine, and I was getting weekly paid speaking gigs. Despite all that, I had a nagging fear that if I wrote anything more about Silicon Valley, I’d become permanently attached to it. Joan Didion didn’t keep writing about hippies after

she’d penned Slouching Towards Bethlehem for the Saturday Evening Post in 1967. I didn’t see the bubble coming, but I persuaded myself that the cultural impact of the dot com boom had peaked, and Silicon Valley would no longer be a cultural story, it was becoming only a business story. So, despite 101 offers of assignment, I turned them all down, and decided to do .... nothing.

That was the hardest part of it. I didn’t have my next idea yet. I didn’t have another life raft to jump into. I did not harbor some other dream. I honestly had no hunch what was next. And it wasn’t like I could afford to sit around; my wife and I had just tapped our entire savings to buy a house. But I had to create room for the next idea to germinate. For about a year, I wondered what to do with my life before I recognized everyone was wondering what to do with their life, and that was my next idea – I would do a book about that question.

Ashley:  On the day-to-day, I think I'm risk averse. I'm pretty much a boring homebody: on most days, if I'm not working, I'm home reading a book, watching a crime drama on TV, or trying to learn to crochet. But career-wise, I've done a bunch of incredibly risky things. (e.g., I've hung out with Belfast paramilitaries.) I guess the craziest risk was when I decided I was going to leave a budding Hollywood career, drive across country, and go work for the Clinton-Gore 1992 presidential campaign in Little Rock, Arkansas. And just 24 hours later, my car was packed, and I was driving East.

The thing is – at the time, other people thought it was a risk. For me, it just made sense. I didn't think of it as a risk or a potentially life-changing choice. Instead, it just seemed like an adventure, doing something that I'd believed in. And I think that's why I take those big risks. I'm not thinking of a long-term downside. I just think, "This makes sense. This is something I need to do for a while," and then I go for it. If I tried to think about risks and their long-term ramifications, then I, too, might have said, "This is crazy," and then I wouldn't have done it.

But it's always the biggest risks I've taken that end up being the most worthwhile.

One Question for Anna Quindlen by Anne Kreamer


Lots of Candles, Plenty of Cake is Anna Quindlen's most recent book.  She is the author of five previous bestselling novels (Rise and ShineBlessingsObject LessonsOne True ThingBlack and Blue), and seven nonfiction books (A Short Guide to a Happy LifeGood Dog. Stay.Being Perfect, Loud & Clear, Living Out Loud, Thinking Out Loud, and How Reading Changed My Life). Her New York Times column “Public and Private” won the Pulitzer Prize in 1992. From 2000-2009, She wrote the “Last Word” column for Newsweek.

Q: What’s the most significant risk you’ve taken professionally?

Anna:  Here's what I consider risky professionally: hanging on to a position because of fear or inertia and waking up one day and realizing you've missed forever the chance to try your change-up pitch.  What's risky is realizing you've never terrified yourself with a flying leap.  When you're feeling completely comfortable in a position, that's the time to move on.There are a hundred reasons not to do that, but they are all grounded in fear and convention.

I think taking a job that scares the hell out of you is the key to success.  It's how you grow.  We're all like sharks: keep moving or die.  Not a dead shark: that's my mantra.

Clive Davis on Risk by Anne Kreamer

In a new memoir, The Soundtrack of My Life, Clive Davis, the Chief Creative Officer for Sony Music Entertainment and the former head of Columbia, Arista and J Records, describes one of his biggest professional risks, signing Janis Joplin and Big Brother and The Holding Company. “But my most startling and decisive revelation occurred on the afternoon of Saturday, June 17, when the second band of the day, Big Brother and the Holding Company, took the stage [at the Monterey Pop Festival, 1967].  They were a San Francisco group and did not have a record out yet.  In the rigorously democratic spirit of that time and place, the band’s singer, the electrifying Janis Joplin, received no special introduction or billing.  But as everyone now realizes, she was unquestionably the star of the band, and her performance was incendiary…Janis’s performance somehow brought the entire meaning of the festival home to me.  The impact of seeing an artist that raw, earthy, and fiery just floored me.  This is a social and musical revolution, I thought, how could it be that none of us in the East knew that this was taking place?  It was literally spine-tingling, and along with the larger insights that came to me about what was going on in the culture, I experienced a personal epiphany as well.  This has got to be my moment, I thought.  I’ve got to sign this band. That was a defining realization.  Although I had begun to make some creative decisions at Columbia, I had no idea that I would really be in the business of signing artists.  I was still very conscious of my lack of a musical background.  But opportunity conspired with necessity for me at Monterey.  Yes, seeing Janis Joplin perform provided one of the greatest musical experiences of my life.  But that occurred within the context of my continual, unspoken awareness that I was running a company that was virtually on the brink.  Nothwithstanding the grandeur of its past, Columbia was barely breaking even.  I had to do something soon, or all my promotions and important titles would amount to nothing.  I’d been relatively cautious for more than a year, but now I had to take some risks and put myself on the line.  Time was of the essence.”

Here's a video from Janis's performance: