Today we’d like to introduce you to Jennifer Colestock.
Hi Jennifer, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
My love affair with Spanish started in college, leading to years of traveling, living across the Spanish-speaking world, and spending over two decades in public education. While I loved teaching middle school, high school, and university students, I found myself increasingly drawn to adult learners—people who show up with a crystal-clear “why”. Whether someone is learning for an upcoming trip, volunteer work, career advancement, or just to keep their brain sharp, there is magic in working with people who are genuinely inspired.
I wanted to build an environment where adults could take learning Spanish seriously without taking themselves too seriously. Let’s be honest: grown-up egos are where language learning goes to die! That’s where the name Gringo Language Academy comes from. It’s playful, but it also carries a real mission. We want to dismantle the old stereotype of what it means to be a gringo. We owe it to the world to step out of our bubble, connect authentically, and actively participate in the cultures around us—and language is the ultimate bridge.
What started as a vision has grown into a vibrant, thriving community. Today, Gringo Language Academy offers live online classes six days a week across all levels, paired with our local “Gringo Gatherings” right here in Central Oregon—from Café y conversación at neighborhood coffee shops and Miércoles de Malbec at local wineries, to underground Cave Tours en español and immersive trips to Mexico for Día de los Muertos. The goal has always been for students to live the language, not just learn it.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Like any small business, simply getting our name out there and raising awareness has been a mountain to climb. But the bigger challenge has been helping adult learners overcome their own mental hurdles. So many adults walk through our doors convinced they are “too old” to learn a new language. Nothing could be further from the truth!
Adults actually learn remarkably well when given the right balance. We bring back the natural immersion and practical application that helped us learn our first language as kids, but we complement it with a practical adult approach. Sometimes, as grown-ups, we just need to “pop the hood” and look at the nitty-gritty grammar logic to make things click.
Overcoming those fears takes structure and support. Beyond our interactive small group classes and tech tools, we partner directly with native-speaking conversation partners to give our students regular, real-world practice every single week. Once students realize they can actually hold a conversation, that old self-doubt (almost) completely evaporates.
Thanks – so what else should our readers know about Gringo Language Academy?
Gringo Language Academy was built on a simple promise: help adults habla más and struggle menos. We want folks to stop “streaking” on apps and actually start speaking Spanish!
We completely threw out the traditional language school playbook. Instead of signing up for an eight-week class at 11:30 AM every Tuesday, Gringo Language Academy is an ongoing, flexible experience. Our monthly membership gives learners unlimited access to live classes, personalized coaching, weekly practice with native speakers, and a 24/7 online Community Hub to keep the momentum going.
We meet people right where they are. We offer the Gringo Glow-Up—a complimentary, 30-minute assessment that gives learners an honest snapshot of their skills and a roadmap for what to tackle next, zero pressure attached. And for our broader community, we publish La Chispa (“The Spark”), our weekly newsletter packed with bite-sized culture, practical phrases, and fun trivia perfect for dropping into your next boring Teams meeting.
What am I most proud of? Hands down, it’s the community. I love hearing students brag about stepping up at the local food bank, comforting a Spanish-speaking patient before an interpreter arrived, or navigating a trip abroad with newfound confidence. But even sweeter is the actual community we are growing: students checking in on each other’s families, sharing travel updates, and giving real, heartfelt hugs when they finally meet in person at a Gringo Gathering. That human connection is the real heartbeat of Gringo Language Academy.
Do you have recommendations for books, apps, blogs, etc?
Transitioning from 25 years in public education to running an online business has been a wild, steep learning curve. In education, necessary changes can take years to happen (if they ever do!); in small business, everything shifts in real-time. It’s been an incredible challenge, but also a healthy dose of my own medicine—a vivid reminder that learning something brand new is hard work, whether it’s the subjunctive or digital marketing strategy!
What keeps me sane? Community, without a doubt. Connecting with fellow small business owners in Bend and across the country has been invaluable. Having incredible mentors in other industries has saved my sanity more times than I can count. Plus, having my technical and business advisor right under the same roof is a massive blessing (even if we occasionally have to remind ourselves to stop talking shop and just be a family!).
At the end of the day, my fuel is simple: good coffee, our dogs, getting outside to soak in the stunning beauty of Central Oregon. And, of course, figuring out where our next Gringo adventure might take us.
Contact Info:
- Website: https://www.gogringolingo.com
- Instagram: https://www.instagram.com/gogringolingo/
- Facebook: https://www.facebook.com/gogringolingo
- LinkedIn: https://www.linkedin.com/company/gogringolingo
- Youtube: https://www.youtube.com/@gogringolingo
