Randi Zuckerberg’s Journey to Main Character Energy

From Silicon Valley to Start Lines

For years, Randi Zuckerberg built her reputation as an investor, entrepreneur, and advisor. But running gave her something new: the chance to step into her own main character moment.

“I’ve always been the advisor or the investor to entrepreneurs. I worked alongside my brother. I’ve always been the person next to the person doing great things… I remember that first 10K race that I entered with the run club, I was like, I feel like I am having a main character moment right now, not a sidekick moment”.

That moment marked the beginning of a radical new chapter. In just two and a half years, she’s run 16 marathons and 13 ultramarathons, including a 250-mile finish at Cocodona.

Rediscovering Running

Randi first dabbled in running in high school cross country and then ran the Chicago Marathon in 2003. “I crossed that finish line and I was like, never again. Cool. Check that off the bucket list”.

Twenty years later, the pandemic shifted her perspective. Lonely in New York City, she noticed a running group that met at a coffee shop. She joined for the post-run brunch but stayed for the community.

“Fast forward about two and a half years from that moment, I’ve now done something like 16 marathons and 13 ultramarathons in this new chapter of my life. So it’s been kind of a wild plot twist that I did not see coming”.

Breaking Stereotypes

Reentering the sport in her forties, Randi encountered skepticism.

“So many people in my life were like, it’s not healthy for a woman in her forties to be running these kind of distances. People are like, you’re going to get injured. Your body isn’t going to hold up”.

Instead of backing down, she used the doubt as fuel: “You’re not limited by your age. You’re not limited by being a mom. You’re allowed to go for big dreams and hard things even if you have children”.

Her message resonates: there are no arbitrary limits based on age or gender.

Training Grit in the City

New York isn’t the most obvious place to prepare for races like Cocodona 250, but Randi embraced creative methods.

“I had to do a lot of crazy stuff. I didn’t have access to trails—going on a treadmill in the dark for hours with no music or no stimulus, or running back and forth over the 59th Street bridge with a full weighted vest for six hours”.

These sessions built the mental toughness she calls her “superpower.”

The Cocodona Experience

When Randi toed the line at Cocodona 250, she committed with full belief:

“If you have even one ounce of doubt in yourself that you’re going to do this, you cannot get on that start line. You have to believe with 400% certainty in yourself that you’re going to finish that race”.

The race was transformative.

“This might actually be the first thing in my entire life after 40 years that is truly all mine”.

Her finish not only reshaped her self-image, but also inspired her family—her teenage son signed up for the Honolulu Marathon after watching her cross the Cocodona finish line.

Main Character Energy

Running gave Randi ownership over her story. “I felt like for the first time in my life I had something that was all mine”.

This shift from sidekick to main character reframed her approach to challenges in business and life. “When you know you have that in yourself, you just kind of carry yourself through the world a little differently”.

What You’ll Learn in This Episode

• How Randi reentered running after 20 years away

• The role of community in reigniting her love of the sport

• Why she views Cocodona 250 as life-changing

• How to reframe limitations around age and gender

• Why fun and joy are as important as grit in endurance sports

• Endurance, Authenticity, and Community

Randi shares her journey with authenticity and stoke, it will be exactly what you need to get through your weekend runs 👇

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About Jon Levitt and For The Long Run

Jon is a runner, cyclist, and podcast host from Boston, MA, who now lives in Boulder, CO. For The Long Run is aimed at exploring the why behind what keeps runners running long, strong, and motivated.

Follow Jon on Instagram, LinkedIn, and Twitter.