A: During my senior year of College at Middlebury, I was eager to find a job, but I was torn between the business and creative worlds. I chose advertising because I believed it would be a balance between the two. But I soon realized that I had not asked essential questions about the organization or the industry that would have helped me find a better match. The problem was most clearly demonstrated when, about 11 months into the position, I was offered a promotion. Over a celebratory lunch with my two senior executives, I asked them if they loved their jobs. They answered in a roundabout fashion that they basically didn’t know if that was necessary. I knew then that I had to find something else. After all, these people were supposed to be my role models. They were on top of the corporate ladder I was just beginning to climb. And, if they were not passionate about their work, how could I be?

It was at that moment that I received a fantastic piece of advice from a mentor: go try things you have never done before. And so I did. I became a volunteer at a nonprofit theater company. In a “hole in the wall” room, I stuffed envelopes for direct mail efforts with the director and producer, the founders of the company. They were working several jobs just to be able to do what they loved. It was inspiring – so inspiring that I wanted to support their growth and success. The question was how. I began reaching out to Broadway producers and business managers and asking a ton of questions. As I learned, I realized that a tremendous amount of inventory goes unsold and that the industry needed to “put butts in seats.” So I called the HR Director at my advertising agency and asked if the company would be willing to send a company-wide email offering employees discount tickets on behalf of the nonprofit for which I was volunteering. Remember, this was 1997. The Internet and email were relatively new. But they agreed, and the results of that email gave me the confidence to start my company.

Today Plum Benefits has established relationships with 20,000 companies offering their employees discounts and access to entertainment, including Broadway, family events and attractions, sporting events and more. To our entertainment partners, we provide a private environment to move distressed tickets while protecting their premium brands. I recently sold Plum Benefits to the parent company of Telecharge, as the deal space has never been hotter with the rise of the Groupons and Gilt Groupes of the world. I am excited about this next stage of my life and career and indebted to everyone – including those bosses at my first job – for contributing to my growth.

A: Define what will best help you reach your top goal; for instance what will drive revenue or be the most profitable? Be sure that aligns with your core competencies. And then choose based on what will take the least resources, time and money. Finally, go with your gut!

A: After founding my company thirteen years ago, I sold Plum Benefits earlier this year. A confluence of factors led to that decision. Personally, I was ready for a new chapter in my life. I believe in change and pushing oneself to experience the new. From a business perspective, the market decline had led to the perfect storm of increased distressed inventory and more buyers looking for discounts, not to mention HR departments who needed to boost employee morale with cost effective benefits. No surprise, the rise of the flash sale and daily deal models was impressive and those of us with years of history in the space had an opportunity as strategic partners wanted in.

The actual decision to sell was very hard because Plum Benefits was my baby. I had to struggle through some very deep self- reflection, but once that decision was made, I was full steam ahead in execution. Still, every phase of completing the deal – from hiring the bankers and developing marketing materials, to negotiation, and close – brought a new emotional experience. I had been warned that it would be difficult and, yes, the amount of work was tremendous, but it kept me focused. I had also been warned that many people experience depression once the company is no longer theirs. But I have been very lucky and the 6 months since the deal was announced have been fantastic. First, the parent company, has allowed us to maintain much of our independence. Second, I set up specific goals I wanted to accomplish with the transition and am proud of the strategic opportunities that have already come to fruition. Finally, as I emotionally separate, I am networking, being influenced by new trends and people, and developing new ideas. That creativity is pure happiness! And this experience has made me so much more self- aware…something I will carry with me from now on.

A: My father is a great influence. He was born in Russia during World War II and his parents were killed shortly thereafter. He was raised by his grandparents in a displaced persons camp after the war in Munich. He came to the United States through Ellis Island, landing in Brooklyn at the age of eleven. From there he made it to NYU Stern, developed a career on Wall Street and, most importantly in his mind, built a family. My dad dreamed big and he led by example. He visualized a life where he was not struggling and could support those he loved. He imagined what it would have been to have a father and actually behaved like that idealized version. He never let his circumstances limit him. He always knew he could influence his outcome through learning, hard work and developing relationships. Beyond being a great role model, he was an enormous support no matter what I was interested in. When I started my company, he was a sounding board for everything from finance to marketing. He would walk into my office and say, “what a country!” Meaning, though I am a woman and a Jew, I have the freedom to live the dream if I am willing to put in the effort and enjoy the process. When he was diagnosed with cancer, he said he was living with cancer and his positive attitude remained. He continued to learn and strive in those final years, and he continued to teach. He was a role model even in death, and despite the fact that he is not literally with me everyday, his influence always is.

A: People have so many goals and so much to do, and there is never enough time to accomplish it all. We can easily get overwhelmed. Although challenging and often “poo-pooed,” I have found that developing a prioritized plan of personal/professional goals and tactics very helpful. The tool I use to ensure those priorities are executed is my online calendar. My schedule blocks time for everything: business meetings, workouts, dinner parties, networking events, and time with my nephew. It also notes work deadlines, birthdays, ideas, grocery lists and more. It is backed by my database of contacts because everything is driven by my relationships. Here I categorize individuals by profession, invite lists, and organizations, for example, and I log all communication so that I can refer back to what was said or experienced together. I also find having a support team to keep you on track is essential. This can include your friends, family, colleagues, mentors, personal trainers, and others. It was a great relief for me as I got older and realized, we don’t have to do it all and we definitely don’t have to do it all alone!

A: I am on the board of The New Group, artist-driven company with a commitment to developing and producing powerful, contemporary theater. It is led by the same artistic director who inspired me to quit my job fifteen years ago. The company has grown tremendously over the years, winning numerous awards, and today we are headed into an exciting planning period for our next five years. Supporting these artists in their effort to present thought provoking work to ever wider audiences is extremely satisfying. I am a big believer in the importance of the arts – I am not the only one who has been inspired to change my life because of something I saw on stage!

A: Life is short. Make the most of it. Strive to learn, love, give back and be healthy. Develop deeply connected relationships wherever you relate to people, be it in the personal realm or the professional. Curiosity will keep you engaged and creative; so always challenge yourself with new experiences.  Be generous with your time and energy because being responsible to others – whether to your children, your employees or your charitable causes – contributes to your personal fulfillment more than anything. Always treat your body well so that you have the strength to take advantage of everyday and the perspective not to get caught up in it.