061: generosity compounds | Jay Stark


In this episode, Deb Knupp welcomes back Jay Stark, partner and wealth advisor at Sutton Wealth Planning of CI Assante Wealth Management, for a second conversation.

“I call it affluenza, like I want more, I want more. And the serum to help fight that is generosity.”

The first introduced the HX Collective community to Jay as a father of two daughters, and he shares that it gave his family a chance to reminisce and deepened those relationships. This time the subject is generosity, and specifically what it means to be a philanthropist of the heart rather than a name on a building. Jay's starting point is an admission: he did not believe the old line that it is better to give than to receive. He believes it now, and the conversation is largely the story of how he got there.

Underlying it all is a claim that lands harder than it first sounds. Abundance is not a number, it is a mindset, and everything compounds, in both directions. A good decision today and an all right decision tomorrow compound toward something. So do the shortcuts. Which means the question is never whether you have enough yet. For most people on a good path, enough is already coming. The question is what you do now, on the path, with what you have already been entrusted.

Key Highlights

  • The kindness documentary. Asked to perform random acts of kindness on camera during Canada's Random Act of Kindness Week, Jay was uncomfortable with being filmed doing good, and did it anyway on a frigid day.

  • What happened outside the grocery store. He quietly covered the bill for someone short on essentials, and a woman he had never met came up to him in tears afterward to tell him what watching it had done to her. His takeaway: get over yourself, because you have no idea who is witnessing the ripple.

  • The batched giving that backfired beautifully. A family faced a large tax bill, so Jay suggested consolidating five or six years of planned giving into one year. Eight or nine months later they called to say they had given it all away. They had seen the impact and wanted more. "It felt like a transaction, but it was actually transformative."

  • Affluenza, and why generosity is the serum. Living in a comparison world where everyone else's life looks like perfection makes "enough" almost impossible to feel. Generosity is the antidote, because giving is proof you already have enough.

  • Why wait? Jay and his wife planned a family foundation for after their deaths, then asked why they shouldn’t start it now. Today the whole family decides together what to support.

  • The best time to plant a tree. Jay’s message to anyone delaying: the best time was 25 years ago, and the second best time is today.

Resources Mentioned

“Give and Take” by Adam Grant

About Our Guest

Jay Stark is a partner and wealth advisor at Sutton Wealth Planning of CI Assante Wealth Management, where his work rests on the belief that wealth is multidimensional, made up of a client's finances, their values and family, and the community they are part of, and that none of it means much if the person holding it is not well. A returning guest on The HX Collective, he first joined Deb to talk about fatherhood and human flourishing through the lens of raising two daughters, both now in their twenties. His practice concentrates less on the number and more on what the number is for, helping families align their resources with what actually brings them meaning, and helping people, including widows who have never been handed the tools, make the impact they already wanted to make. He is an active volunteer and philanthropic leader in his community, a committed advocate for starting small and starting early, and living proof of his own argument that generosity is a habit built rather than a milestone reached.

Connect with Jay Stark

Jay Stark on LinkedIn

Learn more at Sutton Wealth Planning

Watch the kindness documentary on YouTube

About the HX Collective

The HX Collective explores the human experience through three lenses: work, relationships and self, through raw, authentic conversations rooted in human-centered design. Each episode offers gripping stories, thought-provoking discussion, and concrete tools that help you rethink your relationship with distress and strengthen your whole human experience.



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062: hospitality isn’t a gift - it’s a posture | Heather Heaton

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060: showing up in technicolor – be seen, see others | Roy Sexton