Alan MacKenzIE
Co-Founder - Street Smart Ventures
“It’s all about how you wrap the baby.”
“How do we stack the deck?”
Alan MacKenzie built his life and work on those two guiding ideas, that success depends not only on what you create, but how you shape it, present it, and position it for impact. He believed that every meaningful venture could succeed if you wrapped it with care and stacked the deck with purpose, people, and persistence.
A Visionary Who Blended Business with Heart
Alan MacKenzie, MBA and MIT Sloan Fellow, was the visionary founder and driving force behind Street Smart Ventures. His extraordinary career, spanning more than five decades, bridged the corporate, entrepreneurial, and nonprofit worlds. With both head and heart, Alan transformed every space he entered, from boardrooms to community centers, leaving behind a trail of innovation and possibility.
A graduate of Stanford University’s MBA program and a proud MIT Sloan Fellow, Alan combined world-class business insight with deeply human leadership. His early career included executive roles at Fortune 500 companies such as United Technologies, General Foods, and Chevron, as well as a celebrated turnaround as President and CEO of the Hitchcock Chair Company.
But it was his transition into social enterprise that revealed his truest calling, helping people build better lives through opportunity, creativity, and entrepreneurship.
A Lasting Legacy
Alan MacKenzie’s legacy lives on through the people, programs, and partnerships he inspired. His life’s work reflected his belief that everyone deserves the chance to learn, create, and contribute meaningfully.
Street Smart Ventures continues to carry forward that vision, not just as an organization he built, but as a testament to his enduring philosophy: that smart ideas, when fueled by heart, can change the world.
Creating Opportunity: Our Piece of the Pie
Before founding Street Smart Ventures, Alan founded Our Piece of the Pie (OPP), a pioneering youth business incubator based in Hartford, Connecticut. OPP became a national model for youth empowerment, blending business training with real-world experience. Under his leadership, the program helped young people launch 18 youth-led enterprises and served hundreds of youth annually, earning recognition from the U.S. Department of Labor and CT Voices for Children.
Alan’s vision was simple but powerful: when you trust young people with responsibility and creative freedom, they rise to the occasion. OPP embodied that belief, changing countless lives and shaping a generation of youth leaders.
Co-Founding Street Smart Ventures
In 2003, Alan co-founded Street Smart Ventures (SSV), his boldest vision yet. He helped built SSV as a living, breathing movement rooted in empowerment, entrepreneurship, and meaningful opportunity. He saw it as a bridge between traditional workforce programs and the real-world creativity people need to thrive.
Street Smart Ventures became a hub for purpose-driven work, designing and delivering programs that helped individuals discover their talents, gain hands-on experience, and grow into confident, capable entrepreneurs. Alan’s fingerprints remain on every workshop, every framework, and every partnership the organization touches today.
Wisdom and Words That Endure
Alan’s phrases became part of the culture he built:
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“It’s all about how you wrap the baby.”
A reminder that the presentation, care, and strategy behind an idea are as important as the idea itself.
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“How do we stack the deck?”
A challenge to think ahead, to align people, plans, and possibilities so success becomes inevitable.
These sayings carried through his teams, shaping how people at every level approached challenges. They captured Alan’s spirit — part strategist, part mentor, part relentless optimist.
Honoring Alan
We honor Alan not only for what he founded, but for how he lived, with purpose, humor, and a boundless belief in human potential.
His words echo in every idea we nurture, every young person we empower, and every venture that dares to begin.
“It’s all about how you wrap the baby.”
“How do we stack the deck?”
Thank you, Alan, for showing us how.