The Making of You with Deante Young S2 E2 (Help, Advance, and Advocate)
In this episode of The Making of You with Deante Young, Deante sits down with entrepreneur, investor, and longtime economic-development leader Ray Leach to uncover the relationships, losses, and experiences that shaped how he came to see business, community, and his responsibility to other people.
Long before Ray became the founding CEO of JumpStart or co-founder and president of The O.H.I.O Fund, he grew up in a family shaped by business, faith, optimism, and strong relationships.
Then Ray lost his father at seven years old.
His mother returned to work, his older brother took on greater responsibility, and Ray grew up with a gap he says never completely disappears after losing a parent that young. Around the same time, he was already showing entrepreneurial instincts—including selling popcorn at school at about eight years old.
Ray also began doing something revealing: looking for men.
He sought relationships with friends’ fathers and other older men who could provide some of what he had lost. One of the most important was Denny Whalen, who became a father figure during Ray’s teenage years and later gave him one of his earliest professional experiences.
Ray also carried an unusual level of confidence that he still can't completely explain. Looking back at himself at 12, 14, and 16, he remains surprised by his willingness to try things despite the absence he carried. When other kids came at him negatively, his instinct was often to understand rather than retaliate:
“Never assume anything. You don’t know what somebody is carrying.”
But some of Ray’s formation happened much later.
He speaks candidly about growing up largely inside a white world and realizing there were experiences in America he did not understand. His work at JumpStart brought him into deeper relationships across Cleveland, and criticism pushed him to listen, study, and become more intentional about race, inequality, and the communities he was trying to serve.
Ray says he learned to embrace some of that criticism because “I didn’t know what I didn’t know.” His work with community leaders and President Barack Obama’s National Advisory Council for Innovation and Entrepreneurship expanded his understanding of what helping a community could require.
His business journey was equally unpredictable.
After beginning his career at IBM, Ray left at 22 to start a company with longtime friend Keith Stewart. Years later, he attended MIT, hoping to move into venture capital—only to encounter the dot-com collapse, Enron, and the aftermath of September 11.
That disruption brought him back to Northeast Ohio.
Ray thought he might spend a year or two helping build JumpStart.
He stayed for 20 years.
Over time, the work became what Ray describes as a ministry—using knowledge, capital, relationships and resources to help entrepreneurs pursue what they were trying to build.
Behind much of that work was his wife, Jennifer, whom Ray calls his confidant. He says she understands him better than he understands himself and gave him the confidence and mental stamina to lead JumpStart.
Ray also identifies relationships that changed his direction—including Denny Whalen, Keith Stewart, Dorothy Baunach, David Morgenthaler and Mark Kvamme.
Today, through The O.H.I.O Fund, Ray is pursuing what he calls “the most ambitious thing I’ve ever been part of”—another chapter built around relationships, entrepreneurship, and Ohio’s economic potential.
But this conversation is about more than entrepreneurship, investing or economic development.
It is about what happens when loss creates a gap, other people step into it, confidence arrives before evidence, and experience forces you to reconsider what you thought you understood about others.
Because Ray’s story keeps returning to one idea:
Everything is about people and relationships.
🎙️ Watch more episodes of The Making of You with Deante Young:
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