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.
Memories and Wishes From colleagues
"I first meet Alan during my time working at United Services. Immediately it was apparent how much Al believed in people. Whether it was encouraging our clients that were really struggling to believe in themselves, or investing his time into coaching collogues to lift people up, it was evident he believed in the work and his kindness was true. I was lucky enough to continue my friendship with Al long after leaving USI. Al became a part of our "chosen family". From teaching me about hunting and firearms, taking us to game dinners, sharing in conversations about the way of the world, attending our wedding reception, meeting our children and always being generous with his invitations. He lovingly referred to himself as "Grandpa Al" in conversations about our kids. I'm a better person for having known him. His loving spirt and legacy will live on in all of us." - Rachel A.M.
"Alan has always been a beacon of light for young adults. He was always interested in their stories, their business ideas, and overall collaboration with the non profit agencies they were apart of. Alan always greeted everyone from Continuum of Care with a smile and we will never forget Alan. When you thought of YAS BIZ, you thought of Alan. A good soul and overall great person. We thank Alan for what he has done for YAS Biz, for the clients attending, and his support across the board. We will miss you Alan!" - Jerrel C.
"Your passion for Street Smart Ventures and the clients we serve has been an inspiration. I will remeber your gentle, kind, easy manner that was excited for each client's business idea. He had a way of meeting people in their interests and helping them to see their value and abilities. He is at the heart of so many success stories, providing clients these opportunities." - Michele S.
"He was always there with a huge smile on his face but when I would help with registrations, he knew I would be the one signing people up and he was the money guy. LOL" - Alan P.
"I will always remember his dedication and efforts to create positive work experiences for people with disabilities and those facing other employment barriers." - Carol J.
"Al I will miss our laughs and lunches together. I've always admired your passion and wittiness related to our young adults. I will forever remember your famous line "wrapping the baby!"" - Beatrice M.
"Alan, it has been such a pleasure working with you for over 10 years now. The compassion and the dedication that you have shown these young adults is absolutely beautiful. I love that you have offered them many opportunities to explore their own interests and have taught them that their interests can be a business. The dedication that you have to these young adults spills over to the staff that also work with them. Thank you again for all that you have done." - Carnetta P.
"Alan! Thank you so much for your support! Your enthusiasm for my young adults projects, talking with them about their dreams for business plans, and all of the time you spent working with them is so invaluable. You have an incredible spirit and you will be missed." - Jacqueline B.
"I've been so grateful to work alongside you and watch the young adults I support grow through YAS BIZ. Your passion and creativity have made a real difference-for them and for all of us who've had the privilege of working with you. You'll be greatly missed, but your influence will continue to guide and inspire our work every day." - Dawn S.
"Alan was one of the first people who gave me a chance to run events. To this day, both in my job and my side work, I still use so much of what I learned from him while working alongside SSV. Alan has always been someone I look up to, not only in business and entrepreneurship, but also as a person who genuinely cares for others. I still remember when Alan trusted me years ago to find a location for one of the first YAS Biz events. I thought, “Wow, he really believes in me.” Over the years, I’ve carried forward his “It’s how you wrap the baby” approach, applying it to everything I do. Alan hasn’t just encouraged me, he’s inspired countless young adults I work with to find their passions and create their own movement. Thank you, Alan, for the impact you’ve had on my life and so many others." - Shayne C.
"One of my favorite memories with Alan was sharing a lunch in Middletown . I was invited to a meeting at a restaurant, and Alan had ordered mussels . I never had mussels and my curiosity led me to ask if there was sand inside them . Alan let out a laugh and asked if I wanted to try . I did not dare refuse , I tried it. it was amazing and Alan almost ended up giving me his plate. That’s just the kind of sweet and generous, and amazing man he is." Jacqueline T.
"Alan, I’ll always remember when you used to come out to Bridges for meetings with your pups in tow. Whenever I saw that green Outback in the parking lot, I knew we were about to make some real progress toward something great. You had such a gift for bringing people together and bringing out the best in all of us, and of course, would help us wrap the baby in amazing ways. You helped me bring my passion for music into my work at Bridges by helping fund the recording studio, and that changed so much for me and for the people we served. Now, working for the company you started, I see every day how your heart and vision continue to guide so much of what we do. Thank you for your kindness, your belief in people, and the way you’ve always led with generosity and heart. You’ve made a lasting difference in my life, and I’m truly grateful." - John C.
"Alan was a wonderful advocate for our young adults, and he shared his passion to support young people with all of us, inspiring new ideas and possibilities beyond the constraints of disability." - Cindy M.
"Alan was my older brother. He always looked out for me. I miss him terribly!" - Gordon M.
"I first me Alan during my time working at United Services. Immediately it was apparent how much Al believed in people. Whether it was encouraging our clients that were really struggling to believe in themselves, or investing his time into coaching collogues to lift people up, it was evident he believed in the work and his kindness was true. I was lucky enough to continue my friendship with Al long after leaving USI. Al became a part of our "chosen family". From teaching me about hunting and firearms, taking us to game dinners, sharing in conversations about the way of the world, attending our wedding reception, meeting our children and always being generous with his invitations. He lovingly referred to himself as "Grandpa Al" in conversations about our kids. I'm a better person for having known him. His loving spirt and legacy will live on in all of us." - Arcand M.
"Where to begin? I don't have one favorite memory; all of the memories we shared are fantastic. I will say that it was always great to observe him during an event when one of those we served earned some money. He would light up!" - Paul S. Video submission:
