Suze Orman, Kathie Lee, Rebecca Minkoff and More of Our Favorite Ladies Share How They Got to the Top

We asked women at the top of their games what their biggest career risks and best career advice were. Here's what they had to say

Kathie Lee and Hoda, Today show hosts


Suze Orman, Financial advisor, author, TV host

Biggest career risk that’s paid off? “In 1980, after having been a waitress for seven years at the Buttercup Bakery in Berkeley, California making $400 a month at the age of 30, I worked up the courage to go into a Merrill Lynch office to apply for a job to be an account executive. I didn't have any money at the time obviously so I wore the best clothes I had: my red and white striped Sassoon pants tucked into my white cowboy boots with a blue silk shirt. The rest is history.”

Best career advice you’ve ever gotten? “It's better to have 50 percent of something than 100 percent of nothing.”

Rebecca Minkoff, Designer

Biggest career risk that’s paid off? The biggest risk I’ve ever taken is starting this business. I put every dollar I had into the company but I’m so glad I did it!

Best career advice you’ve ever gotten? “Never ever give up on what you want to do, no matter how hard it gets.”

Savannah Guthrie, Today co-anchor


Barbara Corcoran, Real estate mogul and Shark Tank star

Biggest career risk that’s paid off? “In the early '90s, I blew my very first profit on a newfangled promotional idea to put all of the apartments listed at my young real estate company on video tape. It was a disaster, and I lost the $71,000 within the month. Standing in the office basement surrounded by 5,000 unwanted tapes I [remembered] the war games my naval captain husband had just played in South Korea. "We bombed the North Koreans in real time on this new thing called the Internet!" he had gushed. I immediately went out and registered, along with every one of my competitor's urls, and threw all the video-taped apartments up online…Within one week, bang bang, we had two sales out of London from customers who found us online. It took one whole year before the first competitor called me to ask me for its URL back. The largest company called last. Needless to say, being a whole year ahead of the pack pushed my business way, way ahead.”

Best career advice you’ve ever gotten? “When I decided to end my first company, which I'd started with my business partner/boyfriend, he said to me on the way out the door, ‘You know, you'll never succeed without me!’” Insult can be much stronger than advice, and for me it was the best motivator. I knew right then and there I would rather die than let him see me not succeed! I sold my business 20 years later for $66 million."

Maria Bartiromo, CNBC anchor and 10 Laws of Enduring Success co-author


Kate White, I Shouldn’t Be Telling You This author

Biggest career risk that’s paid off? “It’s really hard to say because I learned early on that you get ahead by being a rule breaker so every day for me was about risk. You need to ask yourself each week: Did I try something bold? Did I make my boss say, “Wow?” Did figure out a problem that I could solve and set myself apart from the pack by doing so? The risk I’m most proud of is leaving at 5 every day. I ran five different magazines over the years, and, of course, they weren’t 9-to-5 jobs. I always worked for a couple of hours after everybody else was in bed but I wanted to be home for my kids. What you discover is that no one ever gives you permission to leave at a reasonable hour or go to the soccer games, etc. So you have to be gutsy to only work for good bosses who will be happy with your results, not the fact that you put your family first.”

Best career advice you’ve ever gotten? “‘Get all the information you can.’ This sounds so basic and simple but before you think, ‘I know that,’ hear me out. Often people refuse (intentionally or not) to gather the information they need. They believe what they’ve always been told, they don’t listen, or they don’t dare go below the surface. Information is power, absolutely. For instance, if your boss calls you in and criticizes something, don’t get defensive. Hear her out. Think about what you may be doing to justify her impression. When you are networking, listen more than you talk. Look for information that you can run with (legally, of course!)”

Natalie Morales, Today show news anchor

Biggest career risk that’s paid off? “Launching my career in TV from a position in banking. I always wanted to be a reporter but had a hard time finding a job out of college so I took a job at Chemical Bank as a management trainee in a 2 year finance program… but my heart wasn't in it and I knew I would try and pursue a career as a journalist as soon as my training program was nearing an end. I was making a comfortable $36,000 at the time but knew I would probably face a pay cut in TV. I got lucky and got a job at Court TV for half of what I was making. It was a sacrifice worth making as I was able to gain great television experience, put a tape together, and ultimately from there I was able to get my first on air job at News 12 in the Bronx… then Hartford saw a "diamond in the rough" as the news director called me, and took a chance on me. I was hired as a reporter and weekend anchor... And quickly worked my way to weekday morning anchor. From there MSNBC ... And the rest is history.”

Best career advice you’ve ever gotten? “Do what you love and are most passionate about. The sacrifices will be more worth it and success will follow if you really believe in what you do.”

Mika Brzezinski, Morning Joe co-host 


Rosie Pope, Pregnant in Heels star and Rosie Pope Maternity founder

Biggest career risk that’s paid off?Starting my own business. I decided to start my own family and my own business at the same time, which put a lot of pressure on me because I wasn't just looking after myself anymore, I had a baby. Having said that, times are changing and the stable jobs that generations before us had are no longer as secure, so what may seem risky is actually adapting to the new economic climate. I think you have to be more innovative now when approaching your career.”

Best career advice you’ve ever gotten? “Do something that you love but know that even when you love it there are going to be days that you don't. It's always important to be passionate about what you do but there are two things you need to be real about: First, you are not going to love it every day (most jobs have elements that are not so glamorous) and, second, if you are not good at it, move on.”

S.E. Cupp, The Cycle co-host


Joy Bauer, Nutrition expert and Today show personality

Biggest career risk that’s paid off? “Leaving the security of working in a hospital -- and getting a salary with terrific health benefits -- to start up my own private practice. That decision fueled my confidence and enabled me to make other risky career decisions. Also, pushing myself to take advantage of uncomfortable opportunities, like television and speaking engagements -- that soon became second nature.”

Best career advice you’ve ever gotten? “’Only give advice to people who are interested in hearing it. Otherwise Joy, you're a nag.’ That’s from my smart dad, Artie Schloss.”

Dana Fiser, Jenny Craig C.E.O.

Biggest career risk that’s paid off? “I started with Jenny Craig as a consultant in Florida a little more than 20 years ago, in 1990. I moved up within the organization in various roles in operations, and worked closely with Jenny Craig, the person. (Yes, there is a real Jenny Craig!) In 2000, Jenny asked me to relocate to Australia to serve as the managing director of Australia and New Zealand... It was a huge risk to ask my family to make such a big move to a foreign country, with small children to boot; at the time, they were 3 and 5 years old. The payoff of making that move? …Becoming the C.E.O. in 2011.”

Best career advice you’ve ever gotten?Surround yourself with others who have more expertise in areas where you do not, as we can’t be all things. Talk less, listen more, and move out of their way when they have earned your trust and confidence.”

Carrie Keagan, VH1’s Big Morning Buzz Live with Carrie Keagan host

Biggest career risk that’s paid off? “Instead of starting my career working for someone else and moving my way up, I started my own Internet company and took a chance on myself. I co-founded No Good TV. We were different. We were edgy when edgy was dangerous. We were uncensored when uncensored was new. We pushed the envelope and had an amazing time doing it. It could have all backfired, but instead it took off and lead me to where I am now.

Best career advice you’ve ever gotten? “Imagine your life is a beach. When you see a wave, you don't run from it. Instead, you dive head first into it -- and then ride it all the way in!”

Rep. Cathy McMorris Rodgers


Betsy Beers, Scandal, Grey's Anatomy and Private Practice executive producer

Biggest career risk that’s paid off? “I switched career paths when I was 30. I had been acting and performing comedy for many years and then, unexpectedly, I was offered a full-time job reading scripts at a movie studio. I was terrified to give up my dream in exchange for what seemed to be an entry position behind the scenes. But it turned out that I was way better working with scripts and writers than I was at acting! It led to me producing and it was the best decision I ever made.”

Best career advice you’ve ever gotten? “You will never look foolish asking for help. I often learn a different or better way to handle a situation because someone around me is willing to share their wisdom and experience. In turn, I think they appreciate that I am willing to admit I don’t have a clue what I am doing.”

Lela Davidson, iVoice and Blacklisted from the PTA author

Biggest career risk that’s paid off? “Contradicting a superior when I was a junior associate at an international consulting firm. When my boss and I disagreed about a work process he told me, "Your job is not to ask questions. Your job is to answer questions." We didn't speak for a week, until I confronted him. After that he was my strongest advocate at work. In reality, speaking up probably wasn't such a big risk, but it felt like one at the time. It felt like my job was in jeopardy, and standing up for myself that day set a precedent. It was a turning point.”

Best career advice you’ve ever gotten? “Someone who was recruiting me when I was still in college. He told me not to choose an employer based on the people who worked there, that people would always move on, and the best thing to do was choose based on my needs and ambitions.”

Joy Mangano, HSN personality and entrepreneur

Biggest career risk that’s paid off? “As a single mother of three, I sat back fearful of losing my life savings to make my dreams happen. I was working with QVC at the time and they were going to send my unsold Miracle Mops back to me, so it lead me to stepping on stage in front of all of America to demonstrate my product correctly. I always get nervous speaking in public so it was one of the scariest times in my life on top of the financial risk. Thankfully it was the defining moment that started my path to success as I sold out of thousands in minutes.”

Best career advice you’ve ever gotten? “I was told throughout my career that I must follow the philosophy of the 4 P’s: product, price, presentation equals profit.”

Krystal Ball, MSNBC co-host


Nancy O'Dell, Entertainment Tonight co-anchor

Biggest career risk that’s paid off? “I was offered a job as an investigative reporter and evening anchor in Miami, Florida. It was a huge jump in television market size and I was scared to death! I had never lived outside of my home state of South Carolina. …I remember thinking, "What if I go and fail? Could it ruin the career path I had chosen?" But I realized sometimes you just have to take a leap of faith and go with what feels right in your gut. That experience proved invaluable to me and it gave me the springboard for my career today.”

Best career advice you’ve ever gotten? “Someone once told me: Don't let anyone tell you that you can't do something, no matter what the odds are.” I actually started out in TV sales at a small television market in South Carolina… I got an offer to be a police beat reporter for a bigger market in South Carolina. I remember debating whether to stay in TV sales or take the correspondent job, which was where my heart was. I had a news director tell me, ‘You can't choose being a reporter as your career. The percentage of people who actually make it to the top is so small.’ So I listened to that good piece of advice my friend told me about not letting someone tell me you can't. And not long ago, it happened to me again. I was told not to produce shows because the percentage of shows that actually sell is so low. I quickly remembered the can't/can story…and now love producing as well as hosting, with a show on HGTV (Celebrities at Home), a children's educational app and three additional shows in the works!”

Lori Greiner, Inventor, entrepreneur, QVC personality, and Shark Tank star

Biggest career risk that’s paid off? “I took out a $300,000 loan to create my first product, and today I've created over 400 successful products and hold 115 patents.”

Best career advice you’ve ever gotten? “You can do anything you put your mind to.”

Rehema Ellis, NBC Nightly News 


Beth Engelman, iVoice and co-founder, Mommy On A Shoestring 

Biggest career risk that’s paid off? "I always dreamed of writing a children's book, but never had the courage to do it. Finally, right before my 35th birthday I figured 'it's now or never' so I put together a pitch, flew to LA / NY/ Boston to meet publishers and 16 months later, my first book , 'Finding Fairyland' was in Barnes and Noble. I got quite a few (ie: MANY) rejections, but I stuck with it until I found a publisher who said "yes."

Best career advice you’ve ever gotten? When it comes to pitching ideas --don't let rejection get your down. Instead think of it like dating, you have to "kiss a lot of frogs" (ie: pitch a lot of ideas) until you can find Mr Right (someone to buy your idea!) So pucker up and get out there!




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