travel
(8)
Josh Weinstein and the arithmetic of a good holiday
Josh Weinstein joined Carnival as a lawyer who had never taken a cruise. Two decades later, he became CEO, bringing a treasurer’s eye to the business of a good holiday.
Brian Kidwell and the value of a well-timed email
A backpacker wrote to the author of a cheap-flight ebook. A decade later, Brian Kidwell had helped build Going - and was ready to give someone else the CEO seat.
Marshall Doney
Marshall L. Doney is the President and CEO of AAA Mountain West Group, the federation arm serving more than 6.8 million members across Northern California, Nevada and Utah. A 40-year AAA lifer who started in 1984 as an assistant manager at AAA Wisconsin, he climbed through strategy, marketing and automotive services before running the national office for nine years. He took the Mountain West top job permanently on July 2, 2024.
Caroline Shin
Caroline Shin is the CEO and co-founder of Vacatia, a San Francisco-based marketplace reinventing the $35 billion timeshare industry. A MIT nuclear engineering graduate who cut her teeth building Hotwire from the ground up and running global CRM at Starwood Hotels, she launched Vacatia in 2013 to apply technology-first thinking to an industry that had barely touched the internet. Under her leadership, Vacatia has raised $46.8M across multiple rounds, acquired several resort management companies, grown to 750+ industry partners, and expanded to manage 4,750 resort units across eight states.
Tasneem Amina
Tasneem Amina is the Co-Founder and President of Kindred, a members-only home-swapping platform that lets people exchange homes without exchanging money. Born in South India and immigrated to the US at 14, she studied Biology at the University of Chicago before pivoting into finance and tech. After stints at Goldman Sachs, Yik Yak, and Stitch Fix, she became a product leader at Opendoor - where she grew a business line from $0 to ~$300M in annual volume. She co-founded Kindred in 2021 with fellow Opendoor alum Justine Palefsky after a week locked in a cabin whiteboarding ideas. Kindred has since grown to 300,000+ members and 300,000+ homes across 150+ cities, raising $148M total with a $125M round in February 2026 led by Index Ventures.
Nathaniel Drew
Nathaniel Drew is an American content creator, polyglot, and filmmaker based in Paris, France, with over 1.79 million YouTube subscribers. Born in Los Angeles to Argentine-immigrant parents and raised in Portland, Oregon, he skipped college to teach himself filmmaking and launched his YouTube channel in 2015. Known for his cinematic vlogs exploring travel, language learning, identity, and existential questions, he speaks five or more languages and went viral with 'Speaking 5+ Languages with my Polyglot Grandma.' He also hosts the 'No Backup Plan' podcast, runs a Substack newsletter, creates music, and teaches filmmaking through his 'Frame by Frame' masterclass course.
Brian Chesky
Brian Chesky is the co-founder and CEO of Airbnb, the global home-sharing and travel marketplace operating in 220+ countries. A Rhode Island School of Design-trained industrial designer, Chesky built Airbnb from a $80/night air mattress rental in his San Francisco apartment into a company that went public in December 2020 at an ~$86.5 billion market cap — just nine months after losing 80% of its business to COVID-19. In 2024, his hands-on leadership philosophy sparked a viral debate in Silicon Valley under the term 'founder mode,' coined by Y Combinator's Paul Graham after a Chesky talk. As of 2025, he is steering Airbnb's boldest pivot yet: from a home-rental platform to a full-service travel ecosystem.
Jack Raines
Jack Raines is a writer, investor, and author who turned a $150,000 trading loss into a media career and a Penguin Random House book deal. He writes Young Money, a newsletter with 61,000+ subscribers covering behavioral finance, career philosophy, and what your twenties are actually for. He's now an investment associate at Slow Ventures, where he works on their $63M Creator Fund. Known for viral LinkedIn satire that got him reported to Columbia Business School as the 'Bacon Bandit of Hell's Kitchen,' he combines intellectual rigor with a refusal to take himself too seriously.