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Dina Kaplan’s Journey From Stressed Founder to Mindful Entrepreneur Through Meditation

An Interview With Brooke Bohinc

Dina Kaplan's headshot

Meet Dina Kaplan, the Founder and CEO behind The Path, a vibrant meditation start-up and community that caters to tech founders, investors, and finance and entertainment executives, which was born from her own life-altering experiences. 

After co-founding and leading operations for a web video company, Dina began having panic attacks. She excelled at her job but in her own words “failed at the job of being herself in this role”—a prominent woman in tech at a male-dominated company in a male-dominated industry. In one moment, at a New York City intersection, Dina made a huge decision to leave the company she had founded and take a journey around the world to focus on getting healthy and, ultimately, finding the confidence to be herself. During the trip, a serendipitous moment led her to joining a 12-day silent Vipassana meditation retreat that completely reshaped her path and, in turn, the lives of thousands of others. With inspiration from her father’s entrepreneurial teachings, Dina now leads her new company in a very different way, teaching executives and people with impact to live and lead with mindfulness, authenticity, and a dose of humor.

We asked Dina about the biggest impact The Path has had so far, what she would tell her younger self if she were to start her entrepreneurial journey over again, and what’s next for her and her company.

Tell us the story behind your company’s founding. How and why did you start working on The Path?

I was a really stressed-out tech founder. I thought I needed to suppress my natural personality to fit in—even at my own company. Sometimes if a deal didn’t close with the timing I had wanted, I would want to cry. My co-founders didn’t know how to respond to that, so I started mimicking their behavior, basically trying to act as they would and causing my body to revolt. As the company scaled over, that really didn’t work. That’s when I started having panic attacks daily.

One day when I didn’t think I could cross the street to make it to my office, a voice came to me that said, “You’ve got to get out of here.” It was then that I made the nonobvious decision for a company founder who looked, from the outside, like everything was going so well. I left the company and all of the accolades behind. 

I ended up taking a trip around the world, hoping to get healthy again. During that time, I met a guy walking off a plane in India, and he invited me to join a 12-day silent Vipassana meditation retreat. It was my first real experience with meditation, and that was quite a way to begin! It was hard and so hot I thought I was going to die, but that retreat changed my life. I had huge insights! Eight days in, I knew I was going to come out of the retreat a better person. I was determined to be part of the movement that brings meditation to the mainstream through a new company I’d start, The Path.

I knew at that moment that my mission would be to help people like my former self to live and work with less stress, which is what we do at The Path. We welcome everyone, but our specialty is people with a huge impact. We work with founders of public companies, entertainment executives, non-profit leaders, authors, and many others who want to continue to work and have impact but with less stress, more awareness, and with the confidence to really be themselves. I lead a company again but in a very different way—authentically, expressing my emotions, and asking for help.

By working with CEOs and chairmen of public companies, I'm spreading mindfulness through them, which impacts their companies, customers, boards, and shareholders.

What problem does The Path solve? 

We bring people onto retreats who might never otherwise join a retreat—people who founded companies or invest in them, people who run companies or who have been successful in film, music, television, or other creative fields. We make retreats fun and accessible while still teaching deeply shifting, impactful Buddhist wisdom about how to move away from suffering and towards joy and freedom. We also have a beautiful Meditation Teacher Training program that has small classes, great teachers, and really meaningful learnings and weekly challenges to help everyone who joins become more mindful in their daily lives, even starting the day the class begins!

The superpower of The Path is two things. First, we bring people into a meditation community. The Path fosters a warm, friendly, very open community of people. It makes everything we do and teach much more fun. It’s far better than trying to always meditate on your own and staying motivated to do so! 

Our other specialty is making Buddhist wisdom relatable and accessible so you can apply it to your life right now and share it with others. 

Dina Kaplan leads a group meditation in an elegant room.

What are some of the most meaningful impacts The Path has had so far? 

We have this beautiful, robust meditation teacher training program, and we have trained peacekeepers working with warring warlords in Sudan. We trained the first Buddhist meditation teacher that we know of in the modern world to teach in the Philippines. Each day, we teach entrepreneurs who can then lead their teams in meditation, therapists in hospitals, teachers in inner-city middle schools, and more. I also work personally with CEOs and chairmen of public companies in the entertainment space. I know that spreading mindfulness through them impacts the entire company and, in turn, their customers, board, and shareholders.

We also have a curated Mela meditation retreat that caters to leaders in tech, business, finance, nonprofit, and entertainment. It’s exciting to see so many global leaders join us for their first-ever meditation retreat and love it.

What makes The Path different from other similar organizations?

We give people the tools and techniques to meditate on their own for the rest of their lives. We don’t want to hook someone on an app. We want to teach them to guide themselves so they don’t need to turn on their phone and select an app, a teacher, a time, and a technique each morning when they want to meditate. They can just meditate and enjoy a beautiful, peaceful beginning to the day. We have a great new course called 30 Days to Meditator that I poured my heart into. The idea is that after one month of taking this course, you’ll never need a meditation app or anyone else to guide you again.

In what ways has your upbringing or past experiences contributed to how you operate as an entrepreneur?

My father, Robert S. Kaplan, is a professor at Harvard Business School. When I was growing up, he used to say that there is no greater calling in the world than becoming an entrepreneur, hiring people, giving them good jobs, and contributing to the American economy. So I am proud to be an entrepreneur. But, unlike at my past job, I am fiercely authentic now. I’ll cry at work if I’m sad, I’ll share when I’m having a bad day, and I continually try to be funny, with about a 50% success rate. I also take time off and breaks when I need to, so I am not as burned out as I was in my former tech role.

What would you tell your younger self if you were to start your entrepreneurial journey all over again?

Enjoy the process of the journey. When I started my first tech company, I was completely focused on serving our clients and making enough money to never need to work again. I also worked nonstop. I paused my entire life, including dating, spending time with my best friend, and focusing as much on family as I had in the past and do now. I see now that each day is a day of our lives. We need to live our lives as we want to each moment. I should have taken more personal time and I should have focused more on love, because that is important, too! 

How would you describe the journey you’ve had in a few sentences? Would you do it all over again?

The journey I've had has been wild, intense, fun, and overwhelming—the full entrepreneurial experience. I have learned kindness, patience, and humility after not having those qualities when I started my first startup. Would I do it all over again? No; I think I'd go back to being a TV reporter. I thought that was difficult, but it's definitely easier than running a company!

What’s next for you and The Path?

Writing more. I have found some of the secrets to living with kindness, ease, and joy, and I want to share them with an even wider audience. I want our curated Mela retreat to continue to reach even more people with a huge impact so we can help spread mindfulness and kindness to the film and music worlds, as well as to finance, business, and tech. Let's make it cool to be kind—this is my mission! 

Group meditation guided by Dina Kaplan.

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