One Question for Maira Kalman

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?

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

Trust Your Gut When Founding A Company

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.

Celebrating Success.

Celebrating Success.

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

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

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 Life is her newest book.


Jane Pauley

Jane Pauley

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

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.

ToryBurchPRHeadshotQ: 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

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

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 Life was 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

Collaborators, Po Bronson & Ashley Merryman

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 [Read more…]

One Question for Anna Quindlen

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

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:

One Question for Sheryl Sandberg

In the 90s, as an executive at Nickelodeon, Gerry Laybourne, my boss, and I began a trial flex-time program.  I’d already made the commitment to leave  the office at 5:30 two days a week to squeeze in an essential work-out before going home to my family.   Sheryl Sandberg, the Chief Operating Officer at Facebook, agrees that leaving work at a reasonable time still remains provocative.  In her new book, Lean In:  Women, Work, And The Will To Leadshe examines the progress, or not, women have made in securing leadership positions during these past two decades.   As a former Google executive and Chief of Staff at the United States Treasury Department, she has been at the table (one of her commandments for women to be successful) watching what separates the career trajectories of women from men.  Taking risks is a big piece of her manifesto to “lean in.”

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

Sheryl: This felt extremely risky.  After I had my first child, I began to leave work at 5:30 so I could get home in time to nurse.  Once my son was asleep, I would jump back online and continue my workday.  Still, I went to great lengths to hide my schedule and worried that if anyone knew I was leaving the office at that time, they might assume I wasn’t completely dedicated to my job.

Sandberg-photo-credit-Matt-Albiani500Once I became COO, I wanted co-workers to know that Facebook cared more about results than face-time so I opened up at a company-wide meeting and stated that I left at 5:30.  Later, this “news” became public and spread throughout the internet.  Journalist Ken Auletta joked that I could not have gotten more headlines if I “had murdered someone with an ax.”

While I was glad to jump-start the discussion, all the attention gave me this weird feeling that someone was going to object and fire me. I had to reassure myself that this was absurd. Still, the clamor made me realize how hard it would be for someone in a less-senior position to ask for or admit to this schedule. We have a long way to go before flextime is accepted in most workplaces. And it will only happen if we keep raising the issue.


One Question for Jamaica Kincaid

Jamaica Kincaid was born in St. John’s, Antigua. Her books include At the Bottom of the RiverAnnie JohnLucyThe Autobiography of My Mother, and My Brother.  In See Now Then, her first novel in ten years—a marriage is revealed in all its joys and agonies. This piercing examination of the manifold ways in which the passing of time operates on the human consciousness unfolds gracefully, and Kincaid inhabits each of her characters—a mother, a father, and their two children, living in a small village in New England—as they move, in their own minds, between the present, the past, and the future: for, as she writes, “the present will be now then and the past is now then and the future will be a now then.” Her characters, constrained by the world, despair in their domestic situations. But their minds wander, trying to make linear sense of what is, in fact, nonlinear. See Now Then is Kincaid’s attempt to make clear what is unclear, and to make unclear what we assumed was clear: that is, the beginning, the middle, and the end.

Since the publication of her first short-story collection, At the Bottom of the River, which was nominated for a PEN/Faulkner Award for Fiction, Kincaid has demonstrated a unique talent for seeing beyond and through the surface of things. In See Now Then, she envelops the reader in a world that is both familiar and startling—creating her most emotionally and thematically daring work yet.

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

Jamaica:  You mean apart from being born? Of course, this means that I have to admit to having a profession and what would that be? Well, I am a writer. I never learned how to type properly. I failed that course. I also failed my shorthand courses. If I had known how to do those things, I would have most likely gotten jobs as somebody’s secretary and when I was young that was a proper job for a young woman. Since I couldn’t find anybody who would employ me to answer their correspondence efficiently, I continued in my attempt to be a writer. See how that worked out.

One Question for Jim Cramer

Jim Cramer is host of CNBC’s “Mad Money,” featuring lively guest interviews, viewer calls and, most importantly, the unmatched, fiery opinions of Cramer himself. He serves as the viewer’s personal guide through the confusing jungle of Wall Street investing, navigating through both opportunities and pitfalls with one goal in mind — to help them make money. He’s also co-anchor of the 9 a.m. ET hour of CNBC’s “Squawk on the Street” (M-F: 9 a.m.-12 p.m. ET).

Cramer is the founder of TheStreet, a multimedia provider of financial commentary.

He graduated from Harvard College where he was President and Editor-in-Chief of the prestigious daily, The Harvard Crimson. After graduation he became a reporter for the Tallahassee Democrat and later for the Los Angeles Herald Examiner where he covered stories ranging from homicides to sporting events.

Cramer is a former hedge fund manager and founder/owner and Senior Partner of Cramer Berkowitz. His compounded rate of return was 24 percent after all fees for 15 years at Cramer Berkowitz. He retired from his hedge fund in 2001, where he finished with one of the best records in the business, including having a plus 36 percent year in 2000.

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


You want risk? Walk away from a job that you worked years to get, walk away from a job that paid you more your first month than you had made your whole life. Walk away from Goldman Sachs.

Yet, that’s what I did in February of 1987 because I always wanted

Jim Cramer of Mad Money

Jim Cramer of Mad Money

to work for myself and even though I loved the place, I knew that if I didn’t make a move I might never do so.

I first tried to get a job at Goldman in 1981, the year I enrolled in Harvard Law School. I loved the stock market and while I wanted to be a prosecutor, I knew that the summer between your first and your second year at law school tended not to impact where you ultimately worked.

I figured if you want to go to work in stocks, you might as well go for Goldman Sachs, the best there was and the best there still is.

There was a huge problem, though. They didn’t want law school kids. They wanted business school students. So began what amounted to a two year odyssey to prove that I deserved a slot, one of the coveted 25 or so positions that they granted to those who graduated business school every year.

In the next two years I interviewed with Goldman Sachs ten times, got turned down three times and simply didn’t take no for an answer.

And when I got hired for Securities Sales, advising high net worth individuals and smaller institutions on what to do with their money, I couldn’t believe my good fortune.

The payoff was immediate; the commissions bountiful, the people terrific, the excitement non-stop.

Yet, somehow, it wasn’t enough. Somehow I wanted to work for myself. So I made the most stupid and the most brilliant move of my life, I quit. Four years into it I walked away to start my own hedge fund.

Stupid? Yes, because two months after I started I was already down ten percent for the year. I had lost almost everything I had made in the time I worked at Goldman. Then, after clawing back to plus 3%, I ran smack into the 1987 crash. Fortunately, I had been able to cash out ahead of it, one of those moves that in hindsight looks like genius but at the time was just total self-preservation because the market before the crash had been horrendous.

And that’s where the brilliant came in. Because I had cashed out ahead of the crash, I managed to have a positive return, something that almost no hedge fund manager was able to claim.

In fact, almost everyone else I knew who struck out on his own to run a hedge fund during that period ended up blown to bits.

That meant tens of millions of dollars came my way to manage. Fortunately, I got back in close to the bottom, and the rest was pretty much history as I managed to rack up a return of 24% after all fees over a 14 year period and then retired to move on to full time writing and television.

When I look back at what I did, I still can’t believe that I took that risk. I would have been happy if I stayed at Goldman Sachs, I know that for certain. By my goal had always been to work for myself and when I had enough capital to make a go for it, I jumped at the chance. Even as it was catastrophic at first, I would do it over again in a heartbeat.

But, and this is the big but, I was single at the time, I had no kids, I wasn’t fearful. I didn’t have responsibilities beyond my own rental apartment and share in a place in the Hamptons. So while it was the riskiest move I ever made in my professional life, I knew I did have the rest of life to make it back if I failed.

Looking back 25 years later, that’s certainly not the case anymore.


One Question for Rosanne Cash

Rosanne Cash has recorded eleven No. 1 singles, blurring the genres of country, rock, roots, and pop. She has received one grammy and twelve grammy nominations, among other awards and accolades, including an honorary doctorate from Memphis College of Art. A prolific writer, Cash has written Bodies of Water (Hyperion, 1996),Penelope Jane: A Fairy’s Tale (Harper-Collins, 2006), edited the book Songs Without Rhyme (Hyperion, 2001), and recently penned her memoir Composed (Viking, 2010). Rosanne’s prose and essays have appeared in the New York Times, The Oxford-American, New York Magazine, Newsweek, Rolling Stone, Martha Stewart Living and various other publications. Her last record album, The List, won the Americana Music award for Best Album of the year and was a critical and commercial success.

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


There are series of small risks in my work every day– going for a different note, improvising, trying out a new song in concert for the first time or working with a new musician. Just walking on stage sometimes feels like a risk. I performed at the Rolling Stones tribute earlier this year at Carnegie Hall and when they asked what song I wanted to do, I immediately said

Singer, songwriter, author Rosanne Cash

Singer, songwriter, author Rosanne Cash

‘Gimme Shelter’, because I’ve always thought it was one of the top five greatest rock and roll songs of all time. There couldn’t have been a riskier choice for me. It was thrilling.

Those are the fun risks.

I’ve taken two really big career risks. In 1989, I had a hugely successful album that had four number one singles on it, and I had some leverage with my label, Sony, so I asked if I could produce a record myself. I made a small, dark, acoustic record called “Interiors”. It was something of a mission statement for me. It was authentic and personal and kind of rough around the edges. I thought I had done the best work of my life. My record label heard it and said ‘We can’t do anything with this.’ They put out a single, but didn’t do any promotion for it, and clearly wanted to let the record disappear. I was devastated. About three months after the release I was on a plane, staring out the window, and it came to me that I had to ask to be released from the label or at least transferred to the New York division from Nashville.  I called my dad and asked his advice (something I rarely did). He said ‘screw ’em. You belong in New York.’ I called a meeting with the head of the label and went in alone– no manager or lawyer. I asked them to let me go. I had been there 12 years. Basically, they said ‘we’ll miss you’, and the meeting was over in 20 minutes. I walked out and had to lean against the wall, I was so dizzy. I was scared I had made the biggest mistake of my life.

It was the best thing I’ve ever done for myself. I moved to New York in 1991, I got divorced, I met the love of my life, and that dark little record was nominated for a Grammy in the Contemporary Folk category. It gave me a new set of bona fides in the industry. Things didn’t go easier after that– in fact, they became much more difficult for quite some time. The divorce was excruciating, I was broke, I was the subject of a lot of vicious rumors, and I had no more chart hits after that. But my life opened up and I started relying more on my own instincts. Four years later, I took another risk when I asked to be released from the label entirely, even though my contract wasn’t up, because it just wasn’t working. Again, I went in alone, even though my manager thought it was a bad idea. They let me go, and I started from scratch again. Those career risks are like chess, in a way. There is an element of instinct, but it’s mostly logic and planning and creating a new vision for the future. The other risks– the artistic risks– are the ones that infuse my soul with inspiration and propel me forward and refine my skills and intuition. Those are the risks that connect me with my own authenticity. The career risks are a First World Problem, and anecdotal in retrospect. The artistic risks make me who I am.

One Question for Lawrence O’Donnell

Lawrence O’Donnell, Jr. is a political analyst, journalist, actor, producer, writer and host of The Last Word with Lawrence O’Donnell, a weeknight MSNBC opinion and news program.  He was an Emmy Award-winning producer and writer for the NBC series The West Wing and creator and executive producer of the NBC series, Mister Sterling.  He’s also an occasional actor, appearing as a recurring supporting character of the HBO series Big Love, portraying a lawyer.  He began his career as an aide to U.S. Senator Daniel Patrick Moynihan and was Staff Director for the Senate Finance Committee.

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

Lawrence:  Not going
to law school.

One Question for Sarah Jones

Sarah Jones is a Tony Award winning playwright and performer. Her multi-character solo show Bridge & Tunnel was originally produced Off-Broadway by Oscar-winner Meryl Streep, and went on to become a critically acclaimed, long running hit on Broadway.

Educated at Bryn Mawr College and the United Nations International School, Sarah recently returned to her UN School roots by becoming a UNICEF Goodwill Ambassador, traveling as a spokesperson on violence against children, and performing for audiences from Indonesia to Ethiopia, the Middle East and Japan. Winner of the 2007 Brendan Gill Prize, Sarah has also received grants and commissions from The Ford Foundation, NYSCA, the W. K. Kellogg Foundation, and others, and theater honors including an Obie Award, a Helen Hayes Award, two Drama Desk nominations, and HBO’s US Comedy Arts Festival’s Best One Person Show Award, as well as an NYCLU Calloway Award in recognition of Sarah as the first artist in history to sue the Federal Communications Commission for censorship. The lawsuit resulted in reversal of the censorship ruling, which had targeted her hip-hop poem recording, “Your Revolution.”

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

Sarah:   I always thought the most significant professional risk I’d ever taken was dropping out of Bryn Mawr College as an aspiring lawyer to instead place my destiny in the hands (and voices) of an unruly bunch of fictional characters who lived in
my head. But over the years my ‘people’  have had more of a steadying influence on my life, both on and off stage, than I’d ever expected–or have ever given them credit for.  So I thought I’d ask a few of them what they think my most significant professional risk has been so far.

Rashid, an African American (“Why can’t I just be black, son?”) hip-hop head, sometime rapper, and full time Brooklynite still recovering from the gentrification of Bed Stuy, had this to say: “Sarah Jones’ biggest risk? I’ma have to say turning down a couple of different TV shows cuz of her principles and whatnot. I’m like, yeah, you gotta have your morals and all that, but if them dudes in Hollywood ain’t worried about it, why you gotta be all Holy Dalai Lama and whatnot–just get that check, you feel me? If you still feel bad at the end, at least you got some loot, you could pay for a therapist!”

Lorraine Levine, an octogenarian Jewish bubbie with Eastern European roots who has been in nearly every performance I’ve given, shared the following: “You want risky? I always say Sarah is a very nice young Black performer, but I remember one time she was pale as a ghost–the poor thing, such agita she had–because she agreed to perform in Israel at an Arab theater as part of a multicultural event, trying to be all things to all people, and instead she ended up stuck in the middle. I had told her, with some situations, no matter how much your heart is in the right place, you can’t win.  But did she listen?”

Nereida, an ambitious young DominiRican (half Dominican, half Puerto Rican, all proud) who grew up in what she calls “the capitol of the Dominican Republic, otherwise known as Washington Heights” opined: “Sarah Jones’ riskiest decision has to be when she sued the FCC for censoring her feminist poem/song from radio airplay. I mean, I agree the FCC was clueless, but suing the US government? And on top of that, her lawyers eventually won the battle by forcing them to reverse their decision–I think she really got on their bad side. I mean, not that they would ever retaliate.  I’m sure the IRS audit a few years later was a total coincidencia!

Ms. Lady, an older black woman and self-described PhD (Poor, homeless, and disabled) wanted the last word: “I think the riskiest thing Sarah Jones ever did is what she doing right now–trying to write a commission for the Lincoln Center Theater, and they ain’t gave her no deadline, no subject she gotta stick to, no rules at all. Not like most recent things she been writing. So she got to go someplace she scared to be at–the place where she started from–total freedom, to try, to risk failing, to tell the whole truth like she see it, to let go of fancy expectations if she brave enough. Ain’t nothing and nobody in her way. So naturally, all this freedom got her acting more like she got a prison sentence than a commission. But I tell her everyday, keep on feeling that scared feeling, and when it gets to be too much, lean on into it a little bit more. Then wake up the next day and do it again. The risk gon’ be worth it.


One Question For Daniel Coyle

Daniel Coyle is the New York Times bestselling author of The Little Book of Talent, The Talent Code, Lance Armstrong’s War, and Hardball: A Season in Projects.  A contributing editor for Outside Magazine, he is a two-time National Magazine Award finalist.  Coyle lives in Cleveland, Ohio during the school year and in Homer, Alaska, during the summer with his wife Jen, and their four children.

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

Daniel: It was 1991. I was 26 and working as an associate editor at Outside Magazine, which, in the kind of juxtaposition that happens in Chicago, happened to be located less than a mile from Cabrini-Green, one of the city’s poorest, most notorious
housing projects. One day, one of my fellow editors told me about a youth baseball league that was starting in Cabrini. He and I started coaching with a few other guys our age, and quickly grew to love it — particularly the remarkable, resilient kids we met. At the end of the first year, I realized that there might be a book to be written about our team: one that would tell the story of their lives over the course of a single season.

At that point, the longest piece of journalism I’d written was a one-page article on waterproof-breathable jackets. But naivete is a powerful fuel. I took an unpaid leave of absence from Outside and began spending my days at Cabrini. On the advice of a local social worker, I wore a worn-out sport jacket in order that local gang members would take me for a social worker instead of a police officer. I spent much of the summer in Cabrini-Green, rode with police, spent endless afternoons on the ballfield, and got to know that neighborhood better than I knew my own. Our team, which was average at best, somehow made it all the way to the league championship game. By summer’s end, I had the material for Hardball: A Season in the Projects.

One Question for Kare Anderson

Kare Anderson is an Emmy-winning former NBC and Wall Street Journal reporter who now writes the Connected and Quotable column at Forbes, and speaks on communicating-to-connect. She’s the author of Moving From Me to We and co-founder of the Say it Better Center.

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

Kare:   As a Wall Street Journal reporter, in my second week of work, based in London, and with no background in economics, I was told to interview one of the foremost economists in Europe.

He was so enraged by my “ineptitude” and “ignorance” that were “blindingly evident within minutes of my interview” that he stood up and started pointing and shouting at me in his office with the door open. Yes, I remember those exact words and phrases, and those are the ones that are “clean” enough for me to repeat here.

I kept asking for clarification of his terms and concepts and that irritated him more. A small crowd was forming
just outside his door. I could hear tittering. The economy was bumpy then and he felt strongly about what the government should do. I simply did not understand him at first and it took quite awhile for me to decipher a couple of his views so (barely) adequately write my story.  My boss, the bureau chief was not happy with me when I returned and told him what had happened, including how he finally kicked me out of his office. Walking through that parade of chuckling staffers was not my best moment especially as he had spilled coffee on my skirt during one of his outbursts… I mean clarifications. He wrote a letter to the editor, quite articulately and vividly citing my flaws as a reporter. There were 30.

Yet several people wrote letters say they finally understood the underlying economic theory. That’s what most mattered to me, yet I know the writing was not my strongest because of the pressures I felt, being new to a news bureau and a country.

The unexpected upside for me (and I DO mean unexpected) was that his letter apparently boosted readership of my story… and many people, especially women, expressed outrage at him for his personal attacks. Even more women and men wrote letters to the editor in the coming weeks in support of me because the economist made the mistake of responding to some of the attacks by counter-attacking people by name, thus escalating it. I found it mortifying.

My boss was thankful that the battled was made personal, rather than about my “thin coverage” (his polite phrase) in my original story – and that the back and forth story had legs, getting picked up by other media outlets. My nimble French interpreter (I was moved around Europe and she spoke seven languages) and I bonded over the incident. She was wonderfully protective and reached out to her well-placed friends and family members to fan the flames of the story, I learned months later.

Ironically the visibility made people curious about me so it was easier to secure interviews. Above all it cemented my habit of doing more advance research before an interview and to grow credibility in one, specialized beat so it was less likely I had to cover stories outside my area of expertise.

One Question for Jim Morin

Jim Morin, whose work is distributed by Morintoons Syndicate, won the Pulitzer Prize for editorial cartooning in 1996 and shared the Pulitzer with other members of the Miami Herald editorial board in 1983. He was a Pulitzer finalist in 1977 and 1990.

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

Jim: The most significant risk I’ve taken was dedicating myself to the profession I chose in the first place. Editorial cartooning is a specialized field in many respects. Your drawing involves caricature, usually one that is negative or highly critical of its subject – not the kind of depiction that would make you popular at parties or county fairs. Your drawings ideally communicate strong, often controversial opinions as opposed to the safe illustration desired by newspaper and magazine editors. What other profession requires such skills? 

Putting “political cartoonist” on a resume hardly seems relevant for any other employable position. Those that do pursue this path walk on a high wire above a very small safety net. With the precarious state
of the print journalism business I’ve worked to make that net a tad bigger by producing animated editorial cartoons for the Herald’s online pages as a sort of insurance in the event journalism shifts its platform from paper to computer screen. Regardless, the employment security risks of drawing cartoons for a living are not a laughing matter.

one question

I love hearing interesting people’s important stories.  So once a week or so I’m asking them a single key question about how they’ve navigated difficult moments in life and work.