Building Better Intergenerational Relationships at Work
Bridging Generational Gaps to Fuel Growth and Redefine Success — in Business and Beyond
Introduction: The B Side of Success
What drives the people you see thriving in business today? On Episode 4 of the B Student Podcast, host Betsy Gardner, CEO and President of the Winter Park Chamber, sits down with 25-year-old entrepreneur Nasser Weaver, founder of Homespun Digital, to explore our intergenerational relationships can support your career.
Betsy and Nasser shine a light on intergenerational mentorship, the value of sponsorship, and the unmatched power of saying “yes” to opportunity. This episode is packed with wisdom for emerging and established leaders alike.
The Value of Intergenerational Relationships
At first glance, a 55-year-old CEO and a 25-year-old tech entrepreneur might not seem to have much in common. But as Betsy and Nasser reveal, meaningful professional relationships don’t have to be defined by age alone, they’re built on curiosity, connection and shared purpose.
Their story began when Nasser, a graduate of the Leadership Winter Park program, took Betsy up on an open offer to connect. This spark led to a book club, a flow of innovative ideas, and a reciprocal mentorship — with Betsy providing strategic guidance and sponsorship, and Nasser advising her on all things digital, including how to adapt to Google’s ever-changing algorithms.
Both agree: A successful career isn’t built in isolation. Mentors offer tactical and skills-based support, while sponsors sign their name to your credibility, opening doors that may otherwise stay closed. For Nasser, Betsy wasn’t just a mentor, she became a true sponsor, offering public endorsements and professional introductions that helped Homespun Digital take off.
The Power of Seizing Opportunity with Urgency
Nasser’s superpower? A relentless sense of urgency. “I’m never sleeping on an opportunity,” he says, words backed by action since ninth grade. He got his start at a technology magnet school, building websites for family and friends, landing his first paid “gig” long before most peers considered entrepreneurship.
This attitude is what Betsy calls “converting on third downs”— recognizing and acting on opportunity when it presents itself, no matter how small. Whether accepting coffee meetings, volunteering his tech skills for local nonprofits, or meticulously preparing for public speaking engagements, Nasser demonstrates that even micro-opportunities can be stacked and transformed into major wins.
For young professionals, this proactive approach is essential, especially in a world where economic and social landscapes feel uncertain. As Betsy notes, “Sense of urgency when it’s lacking in the workplace creates anxiety ... Sense of urgency in a sales process means you’re not getting the business if you don’t have that.”
Leading with Service and Building Capital
One of the strongest threads in this conversation is the idea of leading with service — “network starts with free work.” By offering his web expertise to organizations like the Welborne Nursery and Preschool, Nasser not only solved meaningful problems but also expanded his network and reputation.
Betsy draws on insights from Dr. Meg J’s book The Defining Decade, noting how the 20s are a critical time for building social and work capital — two assets Nasser exemplifies through every new project and relationship. Weak ties, those acquaintances rather than close friends, often become the source of new business.
Bridging the Generational Workplace Divide
How do we foster more productive, intergenerational teams? For Betsy, it’s about staying open: “Don’t miss out on the treasure trove of ideas and information that young people have.” For Nasser, older leaders can make younger talent feel comfortable sharing new ideas by simply having an “open spirit.” From tackling technical challenges to adapting to digital transformation and artificial intelligence, true collaboration leverages everyone’s unique lived experience.
Practical advice for both sides? Nasser recommends that older professionals remain receptive, while Betsy urges young people to pick up the phone when a problem arises and always be mindful of professional codes, even in a casual post-pandemic world.
Conclusion: Stay Open, Stay Urgent
Beneath every business success is a B-side —passion, courage, and the drive to seize opportunity. As Nasser and Betsy show, when generations share wisdom and champion each other, everyone rises. Whether you’re forging your network, learning a new tech tool, or simply taking a chance on a young entrepreneur, staying open and moving quickly just might be the winning formula — for business and for life.
Watch the full episode here and subscribe to the Winter Park Chamber of Commerce YouTube channel.