At Project Literacy Lab, we had a chance to catch up with Jeff Mendelsohn. As a serial entrepreneur, investor, and founder and CEO of New Leaf Paper, Jeff also advises entrepreneurs who operate at the intersection of humanity and the environment. Here, he unpacks some major themes relevant to being an entrepreneur.


Can you tell me about a time in which you failed spectacularly? How do you think about failure?

My biggest failure was in the HR front. I always wanted to bring in someone to run New Leaf because I knew it wasn’t my only life work. There were no conscious barriers to bringing on that person, but I never got around to it. It was the hill I never climbed. Any other challenge in the business was really around not following through on getting the right people in leadership roles.

Your relationship with failure often depends on your relationship to yourself in any given moment. Tweet This Quote

Overall, my relationship with failure depends on my relationship to myself in that particular moment. There’s this parallel process of personal growth and business growth. In a less mature version of myself, there’s a lot of self-judgment and blame, which can result in more reactive behavior. Fortunately, although that might have characterized my initial responses to failure, over time I developed more personal awareness that translates into failures being opportunities for growth. Everyone says that, but when you actually feel it, it’s a whole different story.

Throughout your career, have you ever been tempted to give up? What keeps you moving forward?

I’ve never had any doubts about my deep desire to be of great service in this lifetime. I get great satisfaction and I’m very alive when I’m doing this work. I have had challenges around burnout and around having too many things happening at once. Burnout for me is usually not saying no to certain things and not being realistic about what I can do. Stuff can fall apart a bit, but it usually doesn’t last very long.

Martin Luther King, Jr. didn’t inspire the world by saying, ‘I had a nightmare.’ Tweet This Quote

Part of my personality is my ability to envision and see opportunity. It’s a very young part of my personality that sees everything as possible. It can sometimes lead to magical thinking about what I can actually accomplish.

When you encounter difficult decisions, how do you navigate through uncertainty?

The most important thing is to develop real self-awareness. When this happens to me, I’m doing my best to understand the reality of the decision, first and foremost. Really, I go back to my principles and make sure my frame of reference for the decision is my principles—what I hold dear. In this work, it’s all about principle-centered leadership.

Then, it’s about having really trusted sounding boards—people who know me well. I ask them to literally hold me accountable by asking me really good questions. I like to receive feedback in the form of good questions and personal experiences.

The path to real, lasting change is to have a positive vision. Tweet This Quote

How did you first get people to listen to you?

I had this insight early on that I wanted to be disruptive, that the best way to do it was to throw a positive vision out there. With New Leaf, we were a very early company in terms of putting out a positive vision for sustainability—how to be more good and not less bad. At the time, sustainability wasn’t that exciting, but paper itself was such a commodity. We told stories through our customers and people using the product.

There’s a quote I like: Martin Luther King Jr. didn’t inspire the world by saying, “I had a nightmare.” The path to real, lasting change is to have a positive vision.

Ask people you trust to hold you accountable by asking really good questions. Tweet This Quote

How do you measure success?

For me, success would mean delivering on my mission and living my life in a really fulfilling manner. That includes being in nature. I’m not just doing this work because environment is some abstract thing I care about; I care about it up close and personal, and I spend a lot of time in the woods. Success means delivering really well on my mission, having wonderful relationships at work and at home, and enjoying the world I’m trying to support.

If you could only pass along a few bits of information to fellow entrepreneurs, what would you want them to know?

The best thing I could possibly do is to ask really good questions and speak from personal experience. Entrepreneurs tend to be the last people to take advice at face value. I think entrepreneurship is an incredible gift. It’s as creative as any of the arts. We get to envision the world we want to manifest and put the pieces together. There’s no roadmap. Every company is unique and its own work of art.

Entrepreneurs get to envision the world they want to manifest and put the pieces together. Tweet This Quote

Be grateful for the opportunity to be an entrepreneur. It’s one of the most amazing experiences. Allow it to be a personal growth path and business growth path, and be aware of how your own way of being manifests in the culture of the company.

About the author

Brittany Lane

Brittany Lane

Brittany is the global editor of Unreasonable.is, which exists to drive resources and value to entrepreneurs around the world solving big f*$ckin' problems. She believes lasting change happens at the intersection of entrepreneurship and empathy and that good storytelling can move mountains.