Today we’d like to introduce you to Richard Westcott.
Hi Richard, we’d love for you to start by introducing yourself.
In 2006 we relocated from NYC to LA and we started visiting wineries in Paso Robles based on having tried a few bottles of Justin’s Cabernet for $18 a bottle. We fell in love with SLO and North County and the Paso Robles Wine region. The people really make it special, the great stories from winemakers, chefs and artisans are so special. We all are stronger as a family together than divided. In 2018 I retired and we moved to Atascadero where we owned a food truck for 3 years. Than focused solely on Paso Sherpa.
However, while we were still in LA we started Paso Sherpa with the sole purpose of showing people how much this region has to offer. We help set up itineraries as well as guidance and advice for newcomers and old. With 20 years of experience in Paso Wine Country we live showing it off!
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
We arrived in the area in early 2020 in the middle of Covid so we canceled most of our food truck appointments for the first season. Simultaneously in the background, Paso Sherpa was starting to get some traction. I visit wineries shoot some video maybe put a clip up on the Instagram and then some restaurants and hotels and then we started looking at doing custom itineraries and creating fun itineraries that people could understand the region better.
Trying to figure out why a client came here in the first place?well in most cases it was probably a wine for me. It was Justin cab 20 years ago and that Wine tells me a lot about what the guest might be looking at so we try to match them up with similar wineries that might grow their experience in their education.
It’s very difficult building an online business because there are so many options if you typed in “visit Paso Robles” you’d see 20 national travel accounts come up and then a couple of the big ones like pasowine.com which is The wine line and Slo and you know travel Paso and visit Atascadero, so we had to be more specific and more unique and we’re slowly evolving to representing a small family, Wine, producers, multigenerational, wine, producers, restaurant, owners, chefs, artisans from cheese and charcuterie and catering, and all the things that make this such a beautiful place to be.
Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
PasoSherpa is closest to a local wine-country concierge and curator than most of your tourism and wine sites.
PasoSherpa is opinionated. It says, “Start here. Skip that. If you love Rhône wines, look here. If you love big Cabs, go there.” That’s valuable because visitors are overwhelmed by hundreds of wineries. With over 300 wineries, we help visitors navigate Paso Robles Wine Country without wasting time.
Most travel sites recycle the same lists:
* Best wineries
* Top restaurants
* Things to do
Our “First Impressions” content is personal discovery. We’re actually visiting places and sharing reactions. That’s difficult to duplicate and gives readers a reason to come back.
PasoSherpa is the local friend who helps visitors discover the best of Paso Robles Wine Country through firsthand experience, curated recommendations, and insider knowledge—not paid promotions or generic tourism lists. We love having this unique niche.
Sip like a local!
What were you like growing up?
Growing up, I was the youngest of four and was constantly out on my own curious about the world around me, riding my bike everywhere I could explore. I got into music and had several bands through school in college and soon started a career in broadcast technology building television stations, and production facilities all over the country. After almost 40 years and the broadcast industry I retired to pass Robles Wine country and live in Atascadero, which we like to say is 20 minutes from everything.
My traveling for business allowed me to visit different places, cultures restaurants, and eventually got me interested in Wine.
Pricing:
- Custom itineraries range from $125-300 for a weekend,
- Itineraries do not include transportation or tasting fees.
- Educational itineraries, can be created with one on one time with winemakers etc. are extra.
- Visiting the site is rich with free itineraries, information and ideas
Contact Info:
- Website: https://PasoSherpa.com
- Instagram: https://www.instagram.com/pasosherpa?igsh=NTc4MTIwNjQ2YQ%3D%3D&utm_source=qr
- Facebook: https://www.facebook.com/pasosherpa?mibextid=wwXIfr&mibextid=wwXIfr
- Youtube: https://youtube.com/@pasosherpavideo?si=Iixrnj8Zjpp77GNa










