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.

06/25/2026

Would you invest in a vehicle you could trust, registered in the US under its securities laws? Investors want the security of being able to sue in an efficient US court system and deposit funds in major banks like JPMorgan Chase or Bank of America. This desire for legal recourse and stability shapes investment preferences, even for ventures intended for regions like the Caribbean.

06/23/2026

Bridging US legal frameworks with Caribbean investment needs. After a major financial crisis and unregulated schemes led to generational trauma, people are hesitant to invest. It's time to rebuild trust and create pathways for wealth creation back home.

06/19/2026

What if Berkshire Hathaway owned Blackstone? We're building an investment holding company, not a traditional fund. We raise capital onto our balance sheet to invest across public and private companies, private credit, and real estate. Unlike Cornerstone, which focuses on asset management and financial services, we aim for the breadth of Berkshire, investing in diverse assets like Apple and Clayton Homes.

06/17/2026

In a world constantly buzzing with noise, finding moments of true silence can feel like a superpower. It's in these quiet spaces that clarity emerges, creativity sparks, and our inner voice can finally be heard.

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.

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