Mark Rothschild Interview: Entrepreneur, Rabbi and Now Writer of “Accidental Wisdom”

Carl does a deep dive with lifelong enthusiast Mark Rothschild. Mark is always looking for new challenges, which explains his careers as a executive consultant, CEO, founder, entrepreneur, rabbi, writer, speaker and so much more. He’s been featured in AARP, the Today Show, The Moth, National Radio and more.

Mark grew up in a middle-class family in Chicago, his grandparents were German immigrants. Even as a child, Mark was always designing his own path. In high school, he became a talent agent for his friends’ rock n’ roll band. He was successful at getting them bookings. “I started making really good money,” he tells us.

Mark continued to use his entrepreneurial skills through college and beyond. “I started thinking that life wasn’t necessarily linear…at the time ‘patchwork economics’ was popular where you could build a career doing lots of different things, not just as a junior VP hoping to be VP one day, and also to find new passions wherever you went. And that just suited me.” After college, Mark embarked on a career as a McKinsey executive consultant, helping a wide variety of organizations with their communication strategies.

When Mark was working for a research firm, he became intrigued by the advent of the internet and knew he wanted to dive into that. He says he had a good career at FastWeb but it wasn’t inspiring or purpose-driven. Then his wife jokingly challenged him to become a rabbi. Mark again was curious and attended rabbinical school, working in hospitals and JCC’s. “I was never a full-fledged congregational rabbi but I’m glad I did it. While working at the community centers, he says he could see how desperately programs needed good after-school care. Mark founded a national model, “Right at School” that’s now in 1,200 schools nationwide serving 70,000 students. He stepped back from the organization in 2011. He had built the company from scratch to a $100 Million a year thriving company.

Mark currently spends his days between Chicago and San Diego and writes his Accident Wisdom essays on Substack which reaches 30,000 subscribers with humorous, deeply personal essays about family, work, faith and reinvention. Plus he’s just released his new book, “Come, Sit, Stay: Stories and Advice for Humans.” Mark says, “Life is comforting when it’s on repeat. But I find inspiration in the new.”

More about Mark

Here are just a few (of many!) of Mark’s wisdoms on (un)retirement:

• • “Transitioning from executive life to retirement—you just lose that authority, that title, but you have to be okay with that.”

• •  “When we’re in business, the idea is about ‘mastery.’ In the first 50 years of life, that’s the goal. What I find now is that yes, mastery is important but what I also find important is giving myself room not just to fail, but to really suck—it’s so much fun because who cares! It doesn’t matter.”

• •  “This time is a huge opportunity to give of our time and resources. I helped form the Chicago Giving Circle to pool our money to fund worthy organizations. Our children and grandchildren can participate in this in the future too.”

• •  “Don’t get hung up on being who you were…it’s so much more impressive to be who you are. Let it all go, try new things, fail and try again. Just have fun!”