Journey with Jake

#158 - What if your moments of greatest confusion were actually doorways to your most authentic self? Giovanna Silvestre's remarkable journey proves exactly that. From the high-pressure halls of Hollywood to the difficult decision of walking away from her family's beloved Italian restaurant, Giovanna's path shows how embracing uncertainty becomes your greatest strength.

With refreshing candor, Giovanna shares her descent into depression after attaching her self-worth to external validation—her Hollywood career, the family business, romantic relationships. The turning point? A disciplined approach to rebuilding herself from within through yoga, meditation, and gratitude practices that culminated in a pr...

When David Schafran felt his life spiraling into depression and emptiness, he discovered an unexpected lifeline – salsa dancing. That first night on the dance floor sparked something profound: "It makes me feel so happy because it's so joyous and flavorful and juicy." This moment of clarity eventually led David from his high-stress tech startup in Boston to the vibrant streets of Medellín, Colombia, where he immersed himself in dance for five transformative months.

David's story challenges conventional thinking about wellness and healing. Despite practicing meditation and yoga, these solitary pursuits weren't enough to lift him from his...

Bonus 8 - Dr. Douglas Brouwer's journey from Western Michigan to the world and back again offers profound insights into how travel shapes our spiritual lives and understanding of home.

After spending 40 years serving as a Presbyterian pastor around the globe, Doug's adventures took him from maximum security prisons in Philadelphia to a church in Zurich, Switzerland, where he learned German at age 60. His travels weren't merely about seeing new places but about finding deeper meaning and connection with humanity.

The conversation explores Doug's most profound travel experiences, including walking 500 miles along the Camino de Santiago...

#156 - Chris Nance's life reads like an adventure novel where dropping out of school at 13 somehow leads to piloting massive ships down the Mississippi River and co-founding a successful coffee company. Growing up just south of New Orleans in a family of riverboat pilots and commercial fishermen, Chris's education took an unexpected turn after Hurricane Katrina when his mother discontinued homeschooling. Shortly after, his father was imprisoned for tax evasion, pushing Chris into the challenging world of commercial fishing before he could even drive.

The heart of Chris's early journey involves "koonin oysters" – a grueling harvesting method wh...

Most of us dream of adventures in far-off places, but between demanding jobs, packed schedules, and the sheer overwhelm of planning, those dreams often remain just that—dreams. Enter Ross Alcorn, the mastermind behind Itinerary Boss, who's made it his mission to turn travel aspirations into reality for busy professionals.

Ross's journey didn't begin with a goal to start a travel company. It started with a simple need—someone had to plan the group ski trips. As the designated planner among his friends, Ross developed frameworks for orchestrating everything from snowboarding weekends in Colorado to 17-day European adve...

#154 - Imagine plunging down a 35-foot waterfall strapped inside a kayak, or trying to compose a stunning piano piece that captures the serenity of nature. These are just fragments of Jon Cheney's extraordinary journey as a creator, adventurer, entrepreneur, and man of faith.

From his early years in a musical household where his parents prioritized owning a grand piano before even having proper furniture, to his teenage years in Paraguay learning Spanish, Jon's life has been defined by embracing new challenges. His remarkable ability to master languages – including Mandarin Chinese during his church mission – parallels his approach to m...

#153 - Meet Ryan Mellon, a man who completely transformed his life by breaking free from the grind of 80-hour workweeks to embrace a life of global adventure. For over a decade, Ryan worked grueling 14-hour days, splitting time between fixing deep fryers and sorting packages at UPS, until a transformative two-week trip to Costa Rica ignited a vision for something different.

This captivating conversation tracks Ryan's methodical journey from overworked employee to successful digital nomad coach. After convincing his friends to join a year-long RV adventure across America, Ryan discovered he could leverage his real estate license...

The untold story of how a young Peruvian boy's fascination with National Geographic magazines transformed into a life dedicated to global exploration unfolds in my conversation with Jorge Salas Guevara. As founder of New Paths Expeditions, Jorge has crafted extraordinary journeys to 58 destinations across our planet's most remote corners while personally visiting over 102 unique locations.

Jorge's adventure began in the Peruvian Andes, traveling treacherous mountain roads with his family to connect with their ancestral culture. His grandfather's worldwide travels and gift of National Geographic magazines sparked a passion that later flourished when Jorge discovered rock climbing while...

Bonus 7 - Unlock your motivation in our latest episode featuring Devan Gonzalez, a dynamic entrepreneur and fitness enthusiast whose journey inspires countless individuals. From a young age, Devan was pushed to explore different sports, leading him to become a martial arts instructor at just 13. This early exposure laid the groundwork for his lifelong passion for fitness and entrepreneurship.

In this engaging conversation, Devan reveals how he transitioned from personal training into founding Strive 11 Fitness—a unique gym model that mixes the energy of boot camps with the personal touch of individualized training. Through a flexible schedule and pa...

#151 - What could inspire someone to leave a stable engineering career and venture into the unknown on a bicycle? Meet Jacob Lemanski, whose incredible journey of 999 days biking across the globe defies expectations and challenges societal norms. In this episode, Jacob shares his odyssey from rural Pennsylvania to the world stage, driven by a passion ignited during a cross-country bike tour at the tender age of 20. His story is not just about the miles traveled but the transformation of his life's path, as he finds fulfillment and a new identity through this daring adventure.

Jacob's journey wasn't...