Uncharted Paths

Barry Adams grew up in Canada, studied philosophy, and found himself editing magazines in Taiwan before the internet changed everything. What followed was two decades of leaning into what was coming next, across startups and public companies, from Shanghai to Hong Kong to London, always moving closer to where decisions get made. It's a conversation about the cockroach theory of career survival...

Andrew Wong grew up in Silicon Valley expecting to be just another tech professional driving up and down Silicon Valley’s Highway 101. Instead, his career has taken him across continents, through the rise of advertising technology, into the frontier of financial technology and cryptocurrency. Now based in Tokyo, he serves as Group COO of SoraMitsu, a blockchain technology company building financia...

Rebecca Rosenberg spent nearly 15 years working in education tech, leading content strategy and digital teams before making a pivot nobody saw coming: trading the corporate ladder for a classroom. Now a licensed English Language teacher, she's found her purpose working with the students who need it most. It's a conversation about perfectionism, patience, and why the right move isn't al...

Lindsay Hoffman began her career with an accounting internship that opened the door to the fast-growing world of online marketing. From there, she built her career by saying yes to new opportunities, from startup roles to more than a decade at Yahoo across partner management, program management, and business development. Now VP of Corporate Development at BC Ventures, the company behind Brian Chri...

Dave DiAngelo moved to New York to pursue a life in the arts, but an accident forced an unexpected pivot into digital media just as ad tech was taking off. From the grind of Yahoo’s HotJobs to the startup energy of Rubicon Project, he learned resilience, momentum, and how to translate storytelling into business growth. Now founder of Playmaker Sports Media, Dave blends sports, advertising, and phi...

Change comes in two ways: the kind that happens to us, and the kind we choose. And both can shape extraordinary careers. Uncharted Paths is a new podcast hosted by ⁠⁠Greg MacDonald⁠⁠ exploring the pivots, choices, and surprising opportunities that shape our careers. From unexpected changes to bold leaps, each story celebrates how disruption can open doors we never imagined. Follow now to get the f...