From Reflection to Action: Deborah Bennett’s Next Chapter Bloomed in the Leadership and Society Initiative
Combining community, care, and conservation through repurposed flowers
When small businesses thrive, whole communities flourish. That belief guided Tim Lanai as he presented his capstone project in the University of Chicago Leadership & Society Initiative (LSI). His vision is clear: provide underserved entrepreneurs in Chicago with the tools to grow businesses that last — and in turn, create more resilient neighborhoods.
LSI Fellows chart their next chapter of purpose and impact through a yearlong capstone project that evolves into their personal purpose plan, guided by Next Chapter Advisors and enriched through peer-to-peer reflection. In his capstone, Social Change Happening One Small Business at a Time, Tim outlined how he plans to turn decades of entrepreneurial know-how into impact by mentoring small business owners in Chicago’s most challenged neighborhoods.
“I’m doing my part to help all the organizations and thousands of people who are trying to transform our city into a place where it is safe for everyone, and where everyone has equal opportunities,” Tim shared. “Small business is where that change starts.”
From Entrepreneur to Mentor: A Playbook for Profitability and Purpose
Tim’s journey began in high-tech sales, helping printing and publishing companies adopt new technologies. After nearly two decades of working closely with business leaders, he made the leap to entrepreneurship, launching two franchise businesses.
In 2006, he founded an executive search firm focused on placing engineers and scientists in the pharmaceutical industry. Then in 2015, he purchased and built a home services franchise in Nashville, Tennessee. Under Tim’s leadership, that business grew to serve over 4,000 clients, earning multiple awards including Most Philanthropic Franchisee and Franchisee of the Year.
Along the way, Tim developed a series of financial tools and systems that helped his own business grow and now he’s sharing those tools with small businesses across Chicago. Some of the results are striking: one small business he mentored grew nearly eightfold, a transformation that rippled outward to support employee retention, family stability, and broader neighborhood vitality.
Tapping into Chicago’s Ecosystem of Change
Through LSI, Tim has become an active partner to local organizations working to strengthen Chicago’s economic and civic infrastructure. His mentorship is rooted in hands-on advising, financial modeling, and goal-setting to help small business owners move from struggle to sustainability. Working in partnership with several nonprofit organizations, Tim is helping business owners strengthen operations, improve margins, and reimagine what success looks like, not just for themselves, but for their employees, families, and communities.
Whether guiding a start-up bakery on how to manage costs or helping a construction contractor scale up hiring while maintaining margins, Tim’s approach combines hard-won business knowledge with deep empathy. He understands both the challenges of running a small business and the larger stakes: in neighborhoods where jobs are scarce and economic security can feel out of reach, a thriving business can be a lifeline.
Bringing It All Together Through LSI
Tim credits the Leadership & Society Initiative for helping him sharpen and articulate this next chapter. Through LSI’s curriculum, cohort discussions, and purpose planning framework, he was able to reflect on his entrepreneurial journey and clarify how to best deploy his skills in service of others.
“LSI helped me take what I’ve learned in business and think about it not just in terms of success, but in terms of impact,” he said. “It gave me the space to connect what I do best with what could truly benefit our city’s neighborhoods, and see an unmet need where I could contribute right in my own backyard.”
Tim’s project embodies LSI’s core mission: empowering leaders to shift from success to significance by addressing urgent societal issues with courage, humility, and clarity. His work is a powerful reminder that meaningful change doesn’t always start with grand gestures—it can start with one conversation, one spreadsheet, one business that begins to believe it can grow.
As Tim steps into this next chapter, he’s not just helping small businesses become more profitable—he’s helping neighborhoods and communities to thrive.
View his full presentation here.
The University of Chicago Leadership and Society Initiative
The University of Chicago Leadership and Society Initiative (LSI) supports accomplished leaders in successfully transitioning from their longstanding careers toward purposeful next chapters. LSI Fellows immerse themselves in UChicago’s unparalleled environment of big ideas and multigenerational dialogue, gaining frameworks for learning from their past and planning for their futures.
Through LSI’s rigorous and customizable curriculum, Fellows engage with eminent faculty and expert practitioners to explore how their next chapter can be meaningful for them and for society. This Fellowship is a commitment to personal growth, enduring wellness, and dynamic engagement with pressing societal issues.
Contact us to learn more about LSI.
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