Ep 26 - Asking the Tough Questions

In this episode, we’re joined by Ryan Ponsford, co-founder of Gateway for Good and founder of Main Street Philanthropy. Ryan shares his journey from board member to philanthropy advocate, discussing the importance of asking tough questions and bringing various skills to the table as a board member. He dives into the origins of Main Street Philanthropy, which aims to prevent family disputes over wealth by teaching the next generation the value of giving. Through compelling stories, including his work with competing gang members and wealthy families, Ryan highlights the transformative power of philanthropy to foster vision, trust, and communication. He believes in the profound impact of giving and urges us all to start small, as kindness and empathy will follow.

 

IN THIS EPISODE:

• [1:38] Ryan shares how he became a board member and why he began asking unpopular questions

• [6:11] Discussion of the role of a board member and how different boards want a variety of skills brought to the table

• [10:58] Ryan describes the genesis of Main Street Philanthropy to keep families together and not fighting each other when wealth was passed from generation to generation and his friend who was working with troubled teens

• [14:47] How an unexpected conversation can change everything, and Ryan describes his “oh crap” moment and how putting together competing gang members could work together for the good of others

• [17:42 Ryan talks about the incredible power of giving and breaks down the word philanthropy and how it spread around the country

• [25:14] Ryan’s day job is owning a wealth management firm to help families, and he gives an example of working with a wealthy family 

• [31:23] Discussion around the critical question of what matters to you and how we can connect on that goes beyond money and how feelings follow actions

 

KEY TAKEAWAYS: 

• Board members should be engaged and ask questions. If something doesn’t feel right or sound right, it should be challenged. 

• Main Street Philanthropy’s goal is to keep kids from fighting when wealth is transferred from one generation to the next. Main Street teaches giving and investing in something bigger than yourself.

• The philanthropic process can teach vision, financial literacy, trust and communication, and the world would be better. 

 

RESOURCES:

For Profit Law Group - Website

Nonprofit Counsel - Website

Nonprofit Counsel - Instagram

Nonprofit Counsel - Linkedin

https://www.ryanponsford.com/

https://www.gatewayforgood.com/

https://www.linkedin.com/in/ryanponsford

 

BIOGRAPHIES:

May Harris has been a pioneer of nonprofit law practice for over a decade, having founded For Purpose Law Group in April 2012. She serves the nation's nonprofit sector with unparalleled expertise, prioritizing her clients' missions, visions, and values. She specializes in nonprofit and tax-exempt organizations, social enterprise and business law, estate planning and charitable giving.

 

GUEST BIOGRAPHY: Ryan Ponsford

My experience and credentials come from 20 years in the financial industry, both at an institutional and private level.  Individuals, advisors, and families bring me into their lives to bring clarity and simplicity to complex challenges, often involving their businesses, wealth transition, giving greater impact, or providing a unique perspective on reducing risk.  I've worked with families worth several hundred million dollars and those just starting their earning years.  I engage business leaders to create giving programs for their companies and employees to experience the joys of giving purposefully.  

 

I've designed and launched multiple companies, some that have worked, many that have failed miserably.  In each endeavor, I learn, grow, and better understand the power of giving and service.  And what have I learned?  We're all just people trying to do the right things for the right reasons.  We all wake up with fears and insecurities, opportunities and challenges.  We're all trying to find a tribe to connect with to enjoy this experience called life more fully.