Legendary Lemonade, Mini Entrepreneurs, & Big Ideas: Lifelong Skills with Westin, Kennedy, and Jason Hill

Amber Stitt
Aug 19
3 min read

Mini-Entrepreneurs and Big Lessons: Pathways with Amber Stitt

On a special edition of "Pathways with Amber Stitt," host Amber takes us into the world of young entrepreneurship, featuring Jason Hill, his entrepreneurial kids Westin and Kennedy, and a behind-the-scenes look at the family business hustle. This vibrant episode, recorded live at Owwll Studio in Boca Raton during the Unleash Your Superpower conference, offers more than just cute anecdotes—it’s packed with real-world wisdom for entrepreneurs of all ages.

From Playground to Profits: The Lemonade Stand Legacy

Amber opens the episode with a question that resonates with every entrepreneur: “Do you have any advice for entrepreneurs? Because it doesn’t matter what age you are.” This sets the stage for Kennedy and Westin, Jason’s children, to share their journey. Their story is classic kid-preneur: spotting opportunities to sell what they have—snacks like chips, ring pops, and lollipops, and even unused toys. Their most popular venture? The "W & K Legendary Lemonade Stand.”

Their business isn’t just a one-off summer project. Jason describes how Westin and Kennedy orchestrate the whole operation: setting up the stand, managing the crowd, and even amping up their marketing with wireless microphones and speakers. The kids have not only created a buzz in their neighborhood but have learned vital roles—Westin as the energetic salesman and Kennedy as the steady hand managing operations.

Entrepreneurial DNA: Nature or Nurture?

Amber playfully wonders, “Is this naturally happening? Is it in the DNA?” Jason certainly thinks so, pointing out how his kids’ entrepreneurial spirits seem innate, though supported by parental encouragement and resources (including plenty of Costco runs for supplies!). It’s a true family affair—mom offers boundaries (not too many lemonade stands, please), while dad supports scaling up.

The family dynamic highlights a significant point: entrepreneurship thrives with encouragement but also with healthy limits. As Jason shares, “My wife gets concerned that it’s out in our neighborhood a little too much," reminding listeners that entrepreneurial drive should be balanced with respect for community rhythms and family time.

Showmanship and Social Skills

One of the episode’s most insightful moments comes as Amber asks about public speaking and confidence. Kennedy and Westin reveal they’re “pretty used to it now,” with Amber highlighting the advantage of getting comfortable with networking and connecting from an early age—the “currency of life.” Jason adds, “Most people who have success, it’s done through relationships,” illustrating that entrepreneurship isn’t just about sales—it’s about people skills and building lasting connections.

Expanding Their Reach: Real World Sales Experience

The kids’ sales acumen shines outside their neighborhood, too. At a convention, they creatively leveraged their skills, offering on-the-spot deals: “If you download Owwll, we get $10, you get $10.” The result? Lots of app downloads and new fans for the product—a perfect case study in incentive-based marketing that many adult entrepreneurs could learn from!

Shaping the Next Generation—And Being Inspired By Them

One of the most touching moments comes when Jason shares that his kids are featured in his book as a source of inspiration. Amber reflects on how leading by example and inclusion in entrepreneurial life can have a lasting impact, shaping children’s confidence and work ethic.

Final Hoots and Takeaways

The episode wraps with playful “Hoot Hoot” shoutouts and encouragement from Westin and Kennedy. Amber reminds listeners that the real win isn’t just about making money—it’s building freedom, learning responsibility, and developing the courage to bring ideas to life.

Key Takeaways for Listeners:

Entrepreneurship has no age limit: Start small, use what you have, and learn as you go.
Family support matters: Encourage, but set reasonable boundaries to nurture sustainable ambition.
Relationships are currency: Confidence and people skills matter just as much as the product you’re selling.
Let kids lead: Giving children ownership over their projects builds real-world skills for life.