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What We’ll Cover

Josh Kwan is the CEO of The Gathering and co-founder of Praxis, but his path into generosity began long before those titles. Raised by immigrant parents and formed by a faithful local church, Josh carried a deep love for Jesus into a career in journalism. God later redirected him through an unexpected opportunity to help lead philanthropy for entrepreneur David Weekley, where he learned firsthand how wise stewardship, rigorous thinking, and humble dependence on God can work together. That season shaped his conviction that generosity is not a side activity for Christians, but a calling that requires formation in community.

Through Praxis, Josh helped cultivate entrepreneurs whose ventures serve as vehicles for Kingdom impact, grounding ambition in a rule of life that guards the heart from money and power. At The Gathering, he now walks alongside families stewarding significant wealth, helping them embrace risk, think with an eternal horizon, and pursue collaboration over control. This conversation offers a thoughtful vision for generosity shaped by humility, surrender, and deep relationships, and invites you to consider how community might transform your own stewardship journey.

Major Topics Include:

• Formation through intentional community
• Integrating faith and vocation
• Investing in leaders, not just ideas
• Shaping entrepreneurs with a rule of life
• Risk and eternity in Christian philanthropy
• Humility in partnership with practitioners
• Money as amplifier of identity
• Generosity as shared, relational practice
• Balancing strategy with Spirit-led obedience

Quotes to Remember

• “I never thought I’d become a ‘professional Christian.’”
• “If you believe in the leader, you can fund that leader because they are going to do some good things in part because that leader has a pursuit of the Kingdom.”
• “We were able to talk about and put into place the spiritual formation and practices and rhythms at the beginning, so that you’re not thinking about it by the time you’re exiting and you have a lot more zeros behind your name.”
• “The rule of life is meant to be done together in relationship, with transparency and accountability and vulnerability.”
• “I think God’s bigger than the way that He’s made me and put me in this vessel, and I can appreciate someone else’s way of thinking.”
• “One of the remarkable things about Christian generosity is that we have this eternal time horizon.”
• “Effectiveness can itself become an idol.”
• “We sin just like you sin. We put on our pants just like you put on your pants. We need Jesus just like you need Jesus.”
• “How do we take this responsibility, maybe even a burden, and find incredible joy and meaning in joining God’s work in the world?”

Links from the Show

• The Gathering
• Praxis
• David Weekly Foundation (aka Dovetail Impact Foundation)
• When Helping Hurts (see our interview with coauthor Brian Fikkert)
• Gospel Patrons (see our interview with founder John Rinehart)

Bible References from the Show

Matthew 28:19–20 | The Great Commission

“Go therefore and make disciples of all nations, baptizing them in the name of the Father and of the Son and of the Holy Spirit, teaching them to observe all that I have commanded you. And behold, I am with you always, to the end of the age.”

1 Corinthians 12:12–27 | One Body, Many Members

Romans 12:4–5 | Members of One Another

“For as in one body we have many members, and the members do not all have the same function, so we, though many, are one body in Christ, and individually members one of another.”

Take A Step Deeper

On the Finish Line podcast, we are all about stories, seeing how God draws us into generosity over a lifetime. 

But sometimes these stories can leave us thinking, “What’s that next step look like for me?”

That’s exactly why we’ve launched a whole new podcast called Applied Generosity which explores the full landscape of the generous life across 7 different dimensions of generosity. 

Applied Generosity helps make sense of the hundreds of stories we’ve shared on the Finish Line Podcast to help you find that best next step.

If you’ve been inspired by these stories and want to take things to the next level, check out Applied Generosity anywhere you listen to podcasts or at appliedgenerosity.com.