Express Your Whole Self
Lauren Hefferon, Ciclismo Classico
Lauren Hefferon is someone I’ve basically worshipped from afar for 20 years.
Lauren is the founder and CEB (Chief Executive Biker) of Ciclismo Classico, a boutique bicycle adventure tour operator based in Arlington, Massachusetts. While Lauren was navigating her new company through its hockey stick growth phase in the early 90s, I was misbehaving away my early adulthood in nearby Cambridge, on Ciclismo’s newsletter list, dreaming of the day I could scrape together enough savings to head to Tuscany on one of her tours.
Lauren’s insatiable curiosity and need for activity in her youth got her into bicycling early, to the point that she’d often spend entire days on solo rides, criss-crossing the towns around her southern NH home.
By the early 80s, when other college-grad women were trying out their first Jazzercise class, Lauren’s wanderlust had taken her to Italy, where she was rolling up on all-male bicycling clubs in Florence looking for riding partners.
After proving herself in the peloton, and cutting her guide teeth wrangling a few high school bikepacking groups across Europe, she pulled together, as she says, “a crappy van and some crappy bikes” and sold out her first two bicycle trips in Tuscany.
Ciclismo Classico ran their first officially branded trip in 1989, and quickly became known not only for their breathtaking scenic routes and top-notch rider support, but also for the unique experiential aspects built into all of their trips.
Even as Ciclismo has expanded and she’s spent less time guiding and had to focus more on back-office grunt work, Lauren has maintained her passion for a business that allows her to express all the different parts of her personality and create exceptional experiences for others.
And the same intuition that kept her safe cycling alone through Europe in the 80s came in handy at the start of the pandemic, when she quickly sensed that a ‘Plan B’ was going to be required if her 30 year old business was going to survive 2020.
This episode is like three podcasts rolled into one - the origin story of an adventure bicycling pioneer, an inspiring tale about making your passion your profession, and a master class in business resilience and pivoting on the fly.
You can connect with Lauren and Ciclismo Classico via their website, as well as on Instagram and Facebook. She’s also got a Facebook group, Club Ciclismo Classico, that’s open to anyone who loves bicycle travel.
Some useful links from the episode:
NOLS - Wind River (Wyoming)
Interlocken (now Windsor Mountain Summer Camp)
The E-Myth by Michael E. Gerber
Good to Great by Jim Collins
What is a gravel bike? (Just don’t forget your bike gloves and handlebar mirror!)