-- When Ken Steeves Jr. talks about his mother, he doesn’t begin with tragedy; he begins with joy. He remembers Randi May Steeves’s laughter, her belief in possibility, and the way she turned even a Sunday Powerball ticket into a family ritual of hope. Every week after church, she’d buy one ticket and ask, “What would we do if we won?”
“I’d tell her it was silly — that we’d never win,” Steeves Jr. recalls. “And she’d just smile and say, ‘We might not, but it’s free to dream.’”
A decade after her death by suicide, that phrase has become both the name and the mission of his new foundation, “It’s Free To Dream.”
The Weight of Two Worlds
Steeves Jr. grew up in Connecticut, surrounded by wealth but raised in a working-class home. “I went to school with kids whose parents gave them money for the movies,” he recalled. “My parents couldn’t. I always felt like an outsider.”
Today, Steeves Jr. is a Partner and Managing Director at Creative Planning. He was listed among the top financial advisors in the state of Connecticut on Barron’s list of ‘Top Advisor Rankings by State’ (2019-2025), one of the ‘Top 100 Independent Financial Advisors in America’ (2022-2025), was a Five Star Wealth Manager award recipient (2016-2023), and has also been named in Forbes as a ‘Best-In-State Wealth Advisor’ (2025). From the outside, his success looks complete. But for years, Steeves Jr. shared, “I was ignoring my own mental health. It wasn’t until I started therapy that I realized how many people were struggling silently. If I could move that needle even a little, I had to try.”
This foundation, he said, is his mother’s voice echoing forward.
Few people knew Randi like her best friend of 40 years, Jeanette Patton. She remembers the day they met. “I was standing in tears because my sister had disappeared,” Patton recalled. “A woman I didn’t know walked over, opened her arms, and gave me the biggest hug. That was Randi.” That gesture defined a friendship and a legacy. “She was the only one who saw my pain and stepped toward it, and now Ken is doing the same thing for others,” Patton said.
Few realize how widespread mental health struggles and suicide truly are. In 2023 alone, more than 49,000 Americans lost their lives to suicide, the highest number ever recorded, according to the Centers for Disease Control and Prevention. It remains one of the leading causes of death among youth ages 10 to 24.
“Death by suicide doesn’t just take one life- it ripples through generations,” said Sarah Taft, Ken’s sister. “On one side of our family alone, three generations have been devastated by it. What Ken is doing takes immense courage. Talking about mental health after loss isn’t easy, but he’s showing others that even in pain, there can be purpose, and that it’s always free to dream.”
Turning Pain Into Purpose
The It’s Free To Dream Foundation, now a registered 501(c)(3), aims to fund awareness campaigns, youth access programs, and partnerships that make mental health care both available and acceptable. Ken’s brother-in-law, Chris Taft, the foundation’s Vice President and a finance executive with experience at Fanatics and GE, shared, “We have close family members and friends who have struggled with their mental health, and we want to help support programs that encourage people to seek help without shame.”
This year’s gala proceeds will benefit three Connecticut organizations already doing the work on the ground: Bridges Healthcare, Boys & Girls Village, and Navi. Navi Co-Founder, Margaret Hines, shares that “through the contributions and donations at the gala, Navi will be able to give every youth ages 13 to 18 in Connecticut access to digital wellness support.” She continued that “Ken’s leadership and generosity mean thousands of kids will have access to care that could literally save their lives.”
Kevin Hines, one of the world’s leading suicide prevention advocates and among the few survivors of a Golden Gate Bridge jump, will serve as the keynote speaker at the It’s Free To Dream Gala. He said Steeves Jr.’s vision struck him immediately: “The It’s Free To Dream Foundation is truly an extraordinary movement… lives are being changed forever thanks to its bold, compassionate mission.”
(From left to right) John Draper, Chris Taft, Rachel Ochinegro, Margaret Hines, Kevin Hines, Kenneth Steeves Jr., Jeff DelGuidice
A Community of Believers
The foundation’s momentum has drawn support from leaders across industries. Peter Mallouk, President and CEO of Creative Planning, where Steeves Jr. has worked for years, said that “Through his dedication to mental health and suicide prevention, Ken Steeves Jr. is helping build a world where every life is valued and every voice is heard,” Mallouk said. “His compassion is turning awareness into action.”
Mickey Brennan, Partner and Co-head of IWG, GWMS at Apollo Global Management, said Steeves Jr.’s drive comes from something larger than philanthropy. “The It’s Free To Dream Foundation is a powerful tribute to Randi May Steeves and her enduring light,” Brennan said. “Ken isn’t just honoring her memory, he’s building a movement that could redefine how communities talk about mental health.”
The Price of Hope
The It’s Free To Dream Gala will bring together over two hundred guests, including business leaders, philanthropists, advocates, and families that are united by a shared cause. The goal is to raise funds for mental health programs across Connecticut. But Steeves Jr. insists the real metric of success isn’t financial.
“If people leave that room feeling more hopeful than when they walked in, that’s what matters,” he said. “Hope doesn’t cost a thing, and sometimes, it’s the only thing that saves us.”
Ten years after Randi May Steeves’s passing, her son is still buying into her favorite idea… that even in darkness, it’s free to dream.
Tickets and sponsorship information for the December 14 gala and organization are available at itsfreetodream.org.
Contact Info:
Name: Maggie Rose Macar
Email: Send Email
Organization: It's Free To Dream Foundation
Website: https://itsfreetodream.org/
Release ID: 89175956
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