08/09/2013 11:53 am ET Updated Jan 25, 2014

Empress of an Empire

I first heard of Katharine Weymouth while writing about her grandmother, Katharine Graham, for my thesis in college. Katharine Weymouth is the Chief Executive Officer of Washington Post Media and Publisher of The Washington Post, a newspaper that has won 47 Pulitzer Prizes. Her grandmother, Katharine Graham was an American Media Powerhouse, who notably led The Post through the Pentagon Papers and Watergate scandals. Katharine Graham was a leading figure in international politics, business and social circles. She wrote one of my favorite memoirs, Personal History that captures an incredible woman and time in American history.

I felt incredibly honored to speak with Katharine Weymouth on Monday, as it was a historic day for her and her family who have owned The Post for over 80 years. I had selected the title of this article before I knew that the Graham family had sold The Washington Post to the billionaire founder and chief executive of, Jeff Bezos for $250 million. I believe the cream of the crop always rises to the top and that Katharine Weymouth will always be on the top. She'll remain as the CEO and Publisher and lead The Post into a new era. I thought Sally Quinn, a longtime journalist, made a great observation when she said, "Katharine is one of the most authentic people I've ever met." She has historic roots, but there is so much more to her than that. She's poised, a class act and a woman who is going to continue to shape history and politics, but she does it with her own signature style. Trust me when I say she's a woman you'll want to keep an eye on. Because even as a busy mother she seems to always be "on."

Growing up, I used to travel to Washington, D.C. and I would visit family friends, including one of my grandfather's lifelong friends in McLean, VA. My love of politics began there and my grandfather's friend always had amazing stories from serving as a Lieutenant in the United States Navy and later as a Foreign Service Officer who was one of the Americans tasked with writing a new Constitution for Japan after World War II. As I grew older I was offered the chance to study in Japan on a language scholarship and I jumped at the opportunity as well as later studying American politics in Washington, D.C. My grandfather came from an old fashioned background with formal dinners, dressed up cocktail parties, and stayed very close with his friends from Phillips Academy Andover and his brother's circles at Yale University. I loved thinking that there was a woman in that era running the boardrooms as CEO. As the only woman on the board of the Associated Press, Katharine Graham was one of the first women to break through the glass ceiling and integrate an old boys' club. There is a very striking image in her book, where she is literally the only woman in the room of over 50 men. While I valued learning from my grandfather and his peers regarding politics, it was also important for me to learn from women leaders. As her grandmother, Katharine Graham served as an inspiring role model for Katharine Weymouth, who grew up meeting prominent individuals at an early age, such as Vogue's iconic editor Diana Vreeland, Princess Diana, JFK Jr., Carolyn Bessette Kennedy and famous world leaders. As a down-to-earth and genuine person, Katharine Weymouth is someone you could talk to for hours about books, courageous men and women in history as well as some personal stories e.g., her night out on the town where she met Yankee baseball star, Alex Rodriguez, as described in Saturday's New York Times article. Katharine Weymouth, the Harvard-and Stanford-educated lawyer is a combination of beauty and brains, who embodies an old world elegance you rarely come across anymore. Here are excerpts from what I hope is first of our many conversations.

What is your favorite restaurant? "Buck's Fishing & Camping. Small but great."

What was your last meal? "Steak at my best friend Molly's house. I was over there last night for dinner and her husband cooked us steaks."

Favorite wine? "Cakebread chardonnay. "

Designer? "I love Theory and Elie Tahari. They're practical clothes for me around here."

Favorite pair of shoes? "No, I have a lot of shoes though."

Vacation spot? "No, we go to a lot of different spots. But I do love Montana."

Magazine? "Two. The New Yorker. And, it's embarrassing -- People. " One is intellectual and the other is a guilty pleasure.

Guilty pleasure? "Ice cream."

Who is your favorite writer? "I wrote my thesis on Mark Twain. I have to say Mark Twain is my favorite writer of all time."

Favorite book or books? "Reading is my escape. I love Erik Larson's The Devil in the White City. You have to read it." (I told her I'm not really much of a fiction reader and she said that's why you'll love it.) "I have to think I'm actually learning something when I'm reading." (Of course, Personal History is her favorite, as the candid memoir her grandmother wrote will always have sentimental value.) "I also love David McCullough's John Adams."

Favorite party? "No. Well my girlfriend and I throw a Summer White party." A take on the "Black and White Ball" that has been described as "The Party of the Century." Truman Capote hosted the party in 1966 and he selected Katharine Graham as the guest of honor.

Dream guest living or dead? "Abraham Lincoln."

Best fashion moment? "I actually have an anti-fashion moment. I was getting ready with the kids and I was dressing in the dark and I walked out of the house in two dark boots. Later realizing one was black and one was brown." (As) I laughed, thinking this is the renown self-deprecating humor and candor her grandmother was known for, then she said she did have an amazing fashion moment. Oscar de la Renta, a close family friend, took her under his wing for her wedding dress. He brought her into the studio and drew her gown on a piece of paper. She said, "it was silk and incredibly simple, but it was absolutely beautiful."

What were you like as a kid? "I was very different than how I am now. I was shy and terrified of public speaking. I'm now much more extroverted. I was very nerdy growing up, and I wanted to be a serious ballet dancer. I was always wearing my hair in a bun and going to school."

Favorite childhood memory? "The beach. In the summer we would go to my grandmother's house on Martha's Vineyard for two months. The time there was relatively unstructured."

What were you like in your 20s? "I was evolving. I was in college and I was going through a rebellious stage. When I went to law school, I would wear black eyeliner and people would ask, "Is that a biker chick?" I was figuring out who I was, and I wanted to be a prosecutor at the time."

If you could go back and give yourself advice in your 20s what would it be? "Life is not linear. Life is not like that. Make sure you're keeping doors open. Also reach out because people never mind giving advice."

What was it like growing up with your grandmother? "We grew up in New York, and we would mainly see her on holidays. As a teenager we would go see her at her place on the Vineyard. I knew she was not your average grandmother baking cookies. She was very warm to me though. I got to know her again more as an adult in D.C. when I was 25 or 26. She was at the pinnacle of her career. She and my mother were riveted by politics."

Did you have a favorite of her friends? "There were so many, but those who were nice to me. Vernon Jordan was great to me. He's larger than life." He was an attorney and longtime civil rights leader.

What did you think of Diana Vreeland? "I was much younger then, but she was very close with my mother. I just remember thinking she was a cool older woman."

Do you have any great memories from your grandmother's friendship with Jackie Kennedy Onassis and JFK? "St. Martin. Jackie invited us to come out sailing and she was without the kids. I also got to meet JFK Jr. and Carolyn Bessette Kennedy. They were just so glamorous."

She entertained important figures of the 20th century; from Princess Diana, Queen Elizabeth, Truman Capote, Indira Gandhi and many Presidents -- do you have any favorite stories?

"Princess Diana was very shy and just what you thought she would be. She was very genuine. She and my grandmother just hit it off and were great friends."

"Also when my grandmother was going on Oprah she was so nervous. She had just published her memoir, Personal History and Oprah sent her five dozen white roses."

"She would also always play bridge in the summer with Bill Gates and Warren Buffett. She would take bridge lessons during the year to keep up."

What do you consider your greatest achievement? "My kids. They are three people I want to see give back and lead."

Who are your heroes? "My grandmother and Abraham Lincoln. Also people who are courageous and people who stand up when it's not popular to do so. People such as Rosa Parks and Martin Luther King, Jr."

What is the quality you most admire in a woman? "I really admire an ability to be real and to really connect with other people."

What is you favorite character trait? "Two. Integrity and a sense of humor."

What is the quality you most admire in friends? "The same. Integrity and a sense of humor and to not judge each other."

Do you have a mantra or motto? I have two on my door..

"What would you attempt to do if you knew that you could not fail?"
"Done is better than perfect."