Habits and Routines of Entrepreneur Dror Liebenthal

Meet Dror Liebenthal, a visionary entrepreneur reimagining philanthropy and fighting student debt.
Habits and Routines of Entrepreneur Dror Liebenthal

Calvin Rosser connected me with Dror Liebenthal and without thinking much I set up my first scholarship via his platform. Here’s my interview with Dror sharing his work habits, routines, and inspiring business mission.

Who's Dror Liebenthal?

Dror Liebenthal is the co-founder and CEO of Bold.org, a high-growth platform that works with students and donors to make it easy for any person and any company to create and manage scholarships, fellowships, and grants. Bold.org’s mission is to fight student debt, a $1.8T problem that's preventing countless people today from realizing their full potential.

Dror was born in Israel and, after immigrating to the US, was the first in his family to navigate the US education system, with scholarships opening critical educational doors along the way. Dror has a BSE in Chemical and Biological Engineering from Princeton University.

What Are the Most Influential Habits in Your Life?

Reading and Exercising. I try to read one book a week and exercise 4+ times a week. I usually fall short of both of those goals, but the routine is critical for me.

My mental health, creativity, and overall ability to be at the top of my game are all very strongly based on whether I’m learning something new and staying physically active.

To keep the routine, I try to mix it up in both areas. I love hiking and skiing, and I’ve more recently gotten into cycling and yoga. I also read across genres as much as possible – being able to pull in ideas from a variety of fields is so beneficial to creativity and empathy.

How Do You Manage Time?

I generally work from 8 AM–6 PM Monday–Friday, and a few hours on Sunday. We treat building Bold.org as a marathon, not a sprint. There are critical times for sure, but we’re building for the long haul and care more about sustainable progress than work binges followed by burnout.

We also are informal about working hours and don’t have a “required” 9–5. We care way more about getting great work done than which hours someone is working. I try to align what I’m doing to my level of energy and don’t feel guilty about taking off for an afternoon to go ski or hike.

What's Your Work Process and Thinking Behind It?

One of my favorite quotes is from my father, via an Israeli cult classic movie:

“The best way to win a marathon is to start running as fast as you can, and then slowly increase your speed.”

The tremendous impact can start small. Don’t worry about where you’re at today. Worry about being better tomorrow.

I also focus on work processes that drive speed without sacrificing quality. I think it’s incorrect to consider the two as tradeoffs.

When you hire great people, get them the right tools and context to get things done themselves, and get out of the way, speed and quality both increase.

How Do You Meet and Connect with People?

I usually just reach out to people who I’d like to meet.

Sending hundreds of cold messages is a great way to figure out what works and what doesn’t. I keep messages short/sweet/specific.

A great way to very quickly learn about a new topic/industry/problem is to read a few articles or books on it, and then reach out to a bunch of people who are experts.

I don’t spend very much time at all in conferences/events (online or in-person), or online communities. I haven’t found them to be particularly helpful, though I’m sure some are great.

What Are Your Sleeping Rituals?

I’m usually in bed by 10:30 PM and sleep 8 hours a night. I’ve never been a night owl. Sleep is important!

What Are Your Investing Habits?

It can take a lot of time and energy to become a good investor, so I focus pretty much all of my effort on areas where I think I have a competitive advantage.

I don’t have a meaningful advantage in investing fields like the public markets, real estate, so I mostly just invest in index funds there. Very boring.

Where I do think I have an advantage is in building companies, so I spend all of my effort there while minimizing distraction elsewhere. I weigh distraction-risk pretty heavily when considering where I want to invest.

I think more people would be happier and do better if they focused on competing in areas where they have an advantage and ignored everything else.

What's One Question That Helped You Understand the World Better?

“What is considered ‘common knowledge’ about this field but isn’t actually true?”

Many amazing companies and social movements are built around a shared secret that some “common knowledge” constraint isn’t actually true.

For example, 15 years ago, it was common knowledge that you don’t just trust strangers or let them into your home. Airbnb showed that this wasn’t actually true, and the result is an incredible global revolution in how we can travel.

If you see a phenomenon that you don’t intuitively understand, revisiting your “common knowledge” assumptions about it can be a great way to learn about it with an open mind.

At Bold.org, we operate in the philanthropy world, where it’s common knowledge that philanthropies are donation-dependent, cash-constrained, and risk-averse. Our shared secret is that this doesn’t actually have to be true.

What Books, People, Experiences Shaped Your Thinking?

I read from a lot of different genres – most frequently behavioral psychology, startup stories, fantasy fiction, and niche books that I feel help me understand the world better.

Some favorites that influence the way I think are:

Think Again and Give and Take, both by Adam Grant. Influences how I approach communication and collaboration.

The New Jim Crow by Michelle Alexander. Influences how I think about the unequal distribution of opportunity and systemic racism.

Economics in One Lesson by Henry Hazlitt. A strong framework for seeing the big picture and evaluating the second and third-order effects of an idea.

Powerful by Patty McCord. Strongly influences how I think about leadership, hiring, and company culture.

The Diabetes Code by Jason Fung. There’s a massive diabetes epidemic in the US right now. This book is an extremely clear analysis of what’s going on and influences how I think about public and personal health.

Ender’s Game by Orson Scott Card. One of the best sci-fi books of all time. I read this as a kid and have re-read it a half dozen times since. It has such powerful lessons on leadership, problem-solving, and creativity.

I’m a curious designer, marketer, and writer from Lithuania. Co-founder of Best Writing and Port Surfer, marketing advisor at App Idea and growth manager at saas.group. Love reading great books, building stuff online, designing systems, optimizing lifestyle, learning new skills, playing basketball, lifting weights, and traveling. If you like my writing, check out my newsletter.

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