The Upwind Podcast

The Upwind Podcast The Upwind Podcast is a founder-focused show powered by ACTAI Advisors and hosted by Lily Dash, lawyer, entrepreneur, and investor from Barbados.

Born from a shared love of sailing and kiting, Upwind explores the mindset required to make progress.

05/30/2026

Many kids in Barbados know their passions early but lack specialized schools. We need to move beyond a standard curriculum to nurture unique talents and prevent boredom in schools.

05/29/2026

Achieving recognition for genres like Soca requires collective action. It's not just about individual careers, but about artists, government, and the private sector collaborating to create enough submissions to make categories viable. Technology can help reduce costs, but the core solution lies in community effort and sustained commitment.

05/28/2026

Growing up, technology was rapidly evolving. My dad and uncle, both tech enthusiasts, fueled my early curiosity. I went from typing DOS commands to dismantling VCRs, always wanting to know how things worked. It's no surprise I stayed on this tech path.

05/24/2026

Caribbean music dominates global airwaves, yet its genres are excluded from major awards. Artists are questioning why their music is everywhere, making global companies rich, but not recognized by institutions like the Recording Academy. The key may lie in unity and collective action.

05/23/2026

Great ideas often spark from small islands because necessity is the mother of invention. Lacking resources forces us to innovate. The internet lets us see what others have, fueling that desire for more and driving us to create solutions.

05/21/2026

The pandemic could have crushed us, or it could force us out of our comfort zones. For one artist, it meant learning something new. As life shifted online, virtual everything emerged. This isn't just a temporary change; it's a whole new economy being born, with new ways to monetize skills and products.

05/06/2026

A call for greater unity across the Caribbean nations. Imagine a self-sustained food belt, relying less on external resources. It's time to foster more collaboration for collective survival and prosperity.

05/04/2026

05/04/2026

From writing Man Down and the Caribbean anthem Roll It Gal to Impossible and T-Shirt, and pioneering music NFTs ahead of the curve, Shontelle Layne represents Caribbean creativity at its highest level. Loved this conversation. Thank you . Watch the full episode 🎧 on YouTube.

04/14/2026

Imagine a world where your mom can pay with her phone and instantly get rewards, without even knowing it's blockchain. BookIt on the Spree network makes this possible, offering instant payments and rewards for both Web3 and Web2 brands. It's efficient, automated, and self-sovereign, removing the delays and complexities of traditional systems.

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