Executive Presence · Leadership Communication
Executive Presence · Leadership Communication
What founders actually carry between the wins, and how they keep showing up.
Rawle Annandsingh · Innovation Ecosystem Builder · Founder Institute Caribbean
I brought Rawle on because if you spend any time around founders who are actually building, not pitching, you notice the quiet things. The bank account refresh at midnight. The pressure of being the person everyone expects to be steady. Rawle has lived all of it across three industries on two continents, and he speaks about it plainly. This is the side of entrepreneurship the highlight reel never shows.
"The first thirty seconds in any room decide what the next thirty minutes are allowed to be."
Episode Cold Open · Samantha J. Best
Innovation Ecosystem Builder · Founder Institute Caribbean
Rawle Annandsingh is an innovation ecosystem builder, founder, and venture capitalist working across Latin America and the Caribbean. He is Director of Founder Institute Caribbean, Founder and CEO of XBorder, and a Venture Capital Fellow at VC Lab. His career started in his father's automotive business in Trinidad and ran through a year in Venezuela, seven years in Florida hospitality, and a decade of serial entrepreneurship across advertising, events, and tech.
In 2022 his event startup was accepted into Techstars with a 120,000 USD investment. He returned to the Caribbean intentionally, choosing to build the kind of ecosystem he had seen abroad rather than leave the region. His first Founder Institute Caribbean cohort took 93 applications and produced 17 graduates. His current work spans cross-border stablecoin payments for tourism through XBorder, and ecosystem development across more than a dozen markets.
The Techstars offer that asked Rawle to leave Trinidad behind in 2022, and what he chose to do instead.
Why a brilliant child in a bad environment will struggle to fulfill their brilliance, and what that explains about founders trying to build here.
The stablecoin angle behind XBorder that makes cross-border tourism payments settle in seconds instead of days.
The Founder Institute Caribbean numbers that quietly tell you exactly how hard this work is.
The boundary every early-stage founder needs to protect their closest relationships before the work breaks them.
Why your family is not the right circle for the founder conversation, and who is.
"To truly support founders, you need people who understand what it is to be in their shoes."
Rawle Annandsingh · Vol. 005
The conversation continues in the room. Next gathering: June 13 at Cascadia Hotel.
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