Barry Adams - A Global Career Built One Leap at a Time
Barry Adams (https://www.linkedin.com/in/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, why sponsors matter more than mentors, and how jumping from lily pad to lily pad might be the smartest way to build a career no one could have planned.
14 Apr 2026
Andrew Wong - From Silicon Valley to Tokyo
Andrew Wong (https://www.linkedin.com/in/andrew-o-%E5%AE%89%E8%B1%AA-w-2ab209/) 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 financial infrastructure for governments, enterprises, and universities worldwide.
It's a conversation about behavioral credibility, calculated risk, and why the road less traveled isn't just more interesting but might be the only one worth taking.
5 Apr 2026
Rebecca Rosenberg - Trading a Tech Career for Teaching
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 always up.
Mentioned in this episode:
Rebecca's classroom wishlist (https://www.amazon.com/hz/wishlist/ls/3DMOD9C61HIET?ref_=wl_share)
Recommended reads:
Alice in Wonderland by Lewis Carroll
Haroun and the Sea of Stories by Salman Rushdie
NK Jemisin, science fiction and fantasy writer (author recommendation)
4 Mar 2026
Lindsay Hoffman - Pivoting Into the Creator Economy
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 Christopher Slots (https://www.bcslots.com/), Lindsay is helping scale a creator-led business at the intersection of content, community, sponsorships, live experiences, and gaming compliance. It’s a conversation about calculated risk, building confidence in high-stakes environments, and why reinvention can look less like starting over and more like assembling everything you’ve learned into a role that really fits.
17 Feb 2026
Dave DiAngelo - When the Script Changes Mid-Scene
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 philanthropy, curating sports audiences while directing a portion of media spend to vetted sports charities. It’s a conversation about reinvention, risk, and turning setbacks into purpose-driven momentum.
11 Sept 2025
Trailer: Introducing Uncharted Paths
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 (https://www.linkedin.com/in/getitdoneguy/) 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 full episodes as they drop.
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