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Jeffrey Stern is all in for running

Jeffrey Stern is a talented trail, ultra and road runner.

(Dipsea Race photo by Peter Makismow. Photo below of Jeffrey Stern running with dogs by Les Morales.)

By Henry Howard

Jeffrey Stern is a lifelong runner who has thrust himself into the sport 100%. Living just north of San Francisco in Mill Valley, Calif., he became enamored with trail and ultra running once he found the Dipsea, essentially in his back yard.

Just after this interview, the 112th annual Dipsea was held. Stern finished 11th overall in an adjusted time of 50:35 in the unique, 7.4-mile Dipsea race. What makes it an unusual race is the age-adjusted finishing times.

Take, for example, Diana Fitzpatrick. She finished 349th with an actual finishing time of just over 1:13. However, her clock time was 49:08, placing her fourth overall, which is what counts.

Dipsea is a handicapped race, which levels the playing field, Stern says.

“The first year I did the race, a 7-year-old girl outsprinted a 64-year-old woman for the outright win in the race, which is pretty cool and special,” he explains. “Basically, there's 25 or 26 different starting groups that are all separated by a minute. Over the course of the history of the race, the last century plus, they've refined the handicaps. Somewhere they've published that they are hoping for five men and five women of all ages in the top 10. They pretty much accomplish that every year. The winner tends to rotate between a man and a woman. Sometimes really young, sometimes really old.”

Jeffrey Stern has finished the unique Dipsea race 15 times.

This year the top 10 was evenly split between males and females and included runners in their teens, 20s, 30s, 50s and 60s.

“If you're world-class in your age group and gender, then you got a chance to win the race outright, and I don't think there are many races out there that are like that,” says Stern, who has completed the race 15 times. “Another element that is really cool about it is, because of the handicapping system, everyone is shooting to get in not just the top 10 or on the podium, but the top 35. They give each of those top 35 finishers a black-colored shirt with your finishing place on it, and it's really prestigious to win one of those. An odd thing to shoot for in most races, it's a little bit different, but that's kind of a neat element, as well.”

The race itself is also different than most as it is an open course.

“There's multiple ways you can go,” he says. “There's no predetermined flag route, although with land issues going through Muir Woods and various private properties, pulled back a little bit on that in recent years. It still has some options at various points on the course. So that makes it pretty unique.”

Starting out

Known as the “fast kid” growing up, Stern focused his attention on sports like soccer and baseball. After college, he became enchanted by the Dipsea race. And he was, well, off and running.

“When I found out about the Dipsea race, I was starting to miss that element that I had in high school,” he says, referring to athletics. “So it was a nice three-, four-year break. I'd always known I'd been kind of a runner and kind of fast, so it made sense and reinvigorated me.”

From there, he has transitioned to the point where running is not only his passion, it’s his profession.

Stern works for Ultrarunning Magazine, directs a race and coaches athletes.

“It's been a very skewed path,” he says, noting his first job was in finance after graduating with a degree in it. “I just really found that it wasn't for me, it wasn't what I wanted to do the rest of my life.”

Stern moved from San Francisco to Santa Barbara, where he added road cycling and mountain biking to his running. Wanting to fulfill his passion for being outside, he started working events in the cycling and outdoor industry for various brands. Then came freelance writing for Road Cycling Magazine and a couple other publications.

Then came another change.

“I had a pretty bad bike crash that spooked me,” he recalls. “It was around that time that I had made some friends in the ultra running community, and decided to go all in and get a black shirt at the Dipsea. I wanted to try my hand at running and not just be a cyclist who dabbles in running, but be a full-on runner.”

Jeffrey Stern is all in for running, race directing, coaching runners and working for Ultrarunning Magazine.

Dipping his toes into a special race

In August 2017, Stern signed up for the race that he is now the race director for, the Tamalpa Headlands 50K.

“I fell in love with it and have run a bunch of ultras since,” he says. “I don't remember how exactly I was connected with Ultrarunning Magazine, but I think I pitched the editor on an article, and then the relationship just kind of grew from there. It's been really special. Excited to keep it rolling, especially with the new race director role. It feels cool to be giving back. Having it come full circle and be the race director at the race that got me into ultra running is just a whole other layer of really cool excitement.”

For motivation, Stern of course looks to the ultra running community. But his true inspiration is Peggy Jett, who is not a runner.

“I don't know anyone tougher than my mom,” he says. “She's drawn a little bit of bad luck in terms of her heart and her aortic valve calcifying. It's had to be replaced three times, and it's a pretty invasive surgery. But she's come back stronger than ever and always has a positive attitude and is pretty fearless. If my mom can have open heart surgery three times and survive and be thriving, then I can figure out how to make a living in the running industry doing what I love. That’s why she's such an inspiration for me.”

Bringing the energy

That inspiration serves Stern well, whether he is deep in the weeds as a race director or deep in the pain cave as a runner. After knocking off the Boston Marathon in April and his 15th Dipsea last month, he is looking ahead to the Javelina Jundred, his first 100-miler, in October.

Jeffrey Stern heads to the finish at the Boston Marathon.

“I've heard the event is just spectacular,” he says. “It's super fun, kind of Halloween celebration, so that's definitely a goal toward the end of the year. I did run Boston earlier in the year and ran a personal best (2:36) which was super fun. I definitely want to go back there again, too, because that's a super special and historic race. I seem to have an affinity for things that have a lot of history. You can always feel it when you're out on the course. Other racers, people that are putting it on, volunteers, fans — they all have a similar type of feel, and that energy is just a little bit different than some other races, as well.”

As an accomplished athlete, race director, running coach and writer, Stern is all in when it comes to the sport. At some point, he’ll have to set aside each of those hats. When that time comes, what would success look like to him?

“If I've inspired people to jump in and pursue their passion, whether that's running or something more stable, that would be really awesome,” he says. “But then also, to inspire people to run these races, and push their limits, and get a black shirt at the Dipsea, or go run Boston or trying to qualify for Boston. Anything like that. I’ve felt it be very life-changing for me, and sharing that and inspiring other people to have those same experiences would be the ultimate goal.”

Speed drill

Name: Jeffrey Stern

Hometown: Mill Valley, Calif.

Number of years running: 15

How many miles a week do you typically run: 50 to 60

Point of pride: My 15-year Dipsea Race streak

Favorite race distance: 20K

Favorite pre-race or training food/drink: “Peanut butter, jelly and banana sando.”

Favorite piece of gear: Hats

Who inspires you: “My mom - she's had open heart surgery three times in the last 15 years and now more recently, both hips replaced in the last few months.”

Favorite or inspirational song to run to: Tom Rosenthal, “Going To Be Wonderful.”

Favorite or inspirational mantra/phrase: “When joy is a habit, love is a reflex.” - Bob Goff

Where can other runners connect or follow you:

• Website:

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