Backstory:

T

o explain why I’m spearheading this new column, let’s back up 15 years: I’m in yeshivah, on a high from learning. Looking ahead, I envision myself harmoniously balancing Torah and business, growing continuously in both. I’m not sure in which industry I’ll find my niche, but I’m hoping I’ll have a successful career. When it comes to Torah, though, I have pretty clear picture of what I want to accomplish: teach a daf yomi shiur, inspire unaffiliated Jews, host guests for Shabbos, attend minyanim regularly, and have a big, happy family.

Sounds simple enough, right?

After yeshivah, I worked for several kiruv organizations all over the world, including the Ronald Lauder Foundation in Europe, Counterpoint in Australia, and NCSY in Canada. Those were exhilarating, fun, and meaningful; and while I was busy, I was still able to juggle my various responsibilities.

I was blessed to meet Melanie, my wife, eight years ago. She shares my vision and passion, and in 2012, we moved to Eretz Yisrael, where we began teaching at a kiruv program at Bar-Ilan University. I also enrolled in Tel Aviv University’s MBA program. While there, I interned as a management consultant at Deloitte, a professional-services firm, before pivoting into business-development roles for Israeli startups. I also started teaching a daf yomi shiur for young professionals in a suburb of Tel Aviv. Melanie and I were living our dream, but it was becoming increasingly difficult to balance it all.

We moved to Ramat Beit Shemesh to join a vibrant community with schools for our three children, and I started to teach my new shul’s daf yomi shiur (that shiur is still active). I published my first book, The Gift of Stuttering. Since then, I’ve spoken for numerous shuls and organizations around the world about my story, focusing on embracing life’s challenges and leading a meaningful life as a result of adversity. I also started producing short videos for Aish.com.

Professionally, I’ve been running business development for Hometalk, an online platform for home-improvement DIYers. My primary responsibilities include developing relationships with partners like Home Depot, Facebook, and Pinterest, launching new revenue-generating initiatives, and preparing materials for investors. Hometalk has an expansive, beautiful office in Yerushalayim, where I’ve also hosted tours and lectures for various kiruv organizations.

Fifteen years ago, I set the vision for my future. Today, I’m both humbled and proud to say I’m living that reality. But even though my vision, passion, and constant prayer have given me the resources to achieve my goals, it’s still challenging to balance all of my responsibilities! Between my growing family, demanding job, and rigorous learning and teaching schedule, I often feel overwhelmed by the pressure. Although it’s everything I wished for and everything I love to do, it sometimes feels like too much to handle — like I’m in over my head.

I began speaking to various entrepreneurs who successfully balance their personal and professional lives, people with high-profile roles in the business world who lead dynamic, Torah-centered lives. I had been taught that I don’t have to choose between the business and Torah worlds, that it’s not one or the other; rather, I can live and thrive in both. These mentors personify that.

I sat down and prepared a list of nine questions, asking each mentor to answer at least five. I have been humbled by their enthusiasm for my project; their responses are authentic, eye-opening, and valuable.

These question-and-answer conversations are the basis for this column. While I’m writing for somewhat selfish reasons — because I’m seeking the mentorship and advice — I look forward to sharing the wealth with you. Together, we can peek into the minds of Torah-true business leaders, incorporate their lessons into our lives, and be blessed with success in both Torah and business endeavors.

1. What opportunities or personalities played a key role in your career path?
2. Which three character traits have played a key role in your success?
3. What do you do to relax, recharge, or simply have fun? How do you make time for that, and how often?
4. What would you say was your most resounding failure? What did you take away from that experience?
5. If you were granted an extra three hours per day, or a spare million dollars, what would you do with them?
6. What is the most inspiring feedback you’ve ever received? Did that impact what you did next?
7. If you were asked to deliver a TED Talk watched by 50 million people, what topic would you choose to speak about? Why?
8. How do you navigate the tension between your deepest values and the business world?
9. What dos and don’ts would you share with someone hoping to launch a career as an entrepreneur?