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From Grief to Belonging to the World with Barry Hoffner

What can a life spanning international investment banking, award-winning farming, humanitarian work and travel to almost every country on Earth teach us about success, loss, purpose and belonging?

In this episode of the Business Elevation Show, Chris was joined by entrepreneur, humanitarian, world traveller and author Barry Hoffner.

After a fifteen-year career in international investment banking that took him around the world, Barry chose a very different path, becoming a successful farmer of grapes and olives in California. His Silverwood Ranch olive oil went on to win multiple gold medals, while his grapes have been bottled as part of Francis Ford Coppola’s Archimedes wine.

Barry’s life changed profoundly in 2017 when his wife Jackie tragically died in Africa. Faced with devastating grief and a sense that perhaps the best part of his life was behind him, Barry began a remarkable journey that has now taken him to 192 countries and inspired his book, Belonging to the World. Through travel, curiosity and encounters with people from vastly different cultures, he began to discover a renewed sense of connection, meaning and belonging. 

Together, Chris and Barry explored the lessons from his very different chapters in business and life, what investment banking and farming taught him about success and reinvention, and what travelling through some of the world’s most misunderstood places has revealed about risk, humanity and the stories we are told about one another.

They also discussed how Barry has channelled Jackie’s legacy into Caravan to Class and the Bourse Jackie programme, creating opportunities for young women across West Africa through education, leadership and public speaking. 

Here are some top takeaways from the interview you won’t want to miss:

1. Turning Tragedy Into Purpose

Barry experienced a life-changing loss with the death of his wife in 2017, which he describes as his “year zero”. Rather than being defeated by grief, he eventually chose to seek meaning and reconnection by traveling, ultimately visiting 192 countries.

2. The Transformative Power of Travel

Travel served as both an escape and a journey towards healing for Barry. Initially, his global journeys were about occupying himself, but they evolved into intentional quests for connection with people and cultures around the world.

Firsthand experiences abroad gave him a more nuanced, personal view of different countries, often contrasting with the negative narratives seen in mainstream media.

3. The Value of Human Connection

Barry discovered that one can find common ground with people nearly everywhere, regardless of differences in background or culture. He highlighted the openness and kindness he received, such as being welcomed in Iraq despite anxieties about his Jewish heritage.

Even in countries considered dangerous or challenging, he found that fear often wasn’t realised; direct interactions with local people were overwhelmingly positive.

4. Building Community and Giving Back

After building a successful career in international finance and later as a farmer, Barry now channels his efforts into humanitarian work, specifically focusing on female education and empowerment in West Africa through Caravan to Class and the Bourse Jackie program.

These initiatives have built schools, provided scholarships, and developed leadership and public speaking skills among hundreds of young women.

5. Challenging Perceptions

Personal experiences in places like Afghanistan, Iran, and Syria showed Barry.that the reality of these societies can be radically different from the way media portrays them. He encouraged judgment based on firsthand experience rather than generalised fear or hostility.

6. Lessons for Business and Life

Openness to chance and being receptive to unexpected opportunities shaped much of Barry Hoffner’s journey and successes.

He learned the importance of community support, adaptability, and personal reinvention—whether managing a vineyard or navigating profound personal loss.

7. The Meaning of ‘Belonging to the World’

For Barry, true belonging means seeing the world not in terms of borders but in terms of people, impressions, and meaningful connections. He strives for next-level connection everywhere, whether abroad or at home.

He views himself as a globalist who believes in the wisdom and the transformative potential of engaging with the wider world.

You’re just one good question away from a real connection with somebody.
– Barry Hoffner

Listen for a fascinating, moving and ultimately hopeful conversation about business, reinvention, resilience, grief and purpose—and what an extraordinary journey through life and around the world can teach us about connecting more deeply, finding meaning after loss and truly belonging to the world.

You can listen to this Business Elevation Show interview with Barry Hoffner & Chris Cooper here. Alternatively on Apple Podcasts, Spotify, Tunein, Amazon Music, iHeart Radio (latter US only).

More about Barry Hoffner:

After a fifteen-year career in investment banking that took him around the world, Barry transitioned into a second career farming grapes and olives. His Silverwood Ranch olive oil has earned multiple gold medals, and his wine grapes have been bottled into Francis Ford Coppola’s Archimedes wine.

Today, Barry is the founder of Caravan to Class, a nonprofit he launched in 2010 to advance girls’ education in West Africa through the Bourse Jackie program, named in honor of his late wife. His book, Belonging to the World (Girl Friday Books), chronicles his journey to every country in the world following Jackie’s tragic passing in Africa in late 2017.