Risky Routes
Founders, executives and investors on the decisions that actually shaped them — the psychology of leadership, risk, and building things that last.
Oct 27, 2026
Michel Bayan — Serial Entrepreneur & Advisor at Geoship
Filmed in New York, NY
Michel Bayan started out as an actor and a yoga teacher to the stars in Hollywood. Then the business “sucked,” so he tried hacking it, first as a producer, then running a digital agency, then building his own startup.
Aug 25, 2026
Kimberly Trueba — Chief Executive Officer, Girl Scouts of Southern Nevada
Filmed in Las Vegas, NV
Kimberly Trueba has built a career around one core idea: the environments we create shape how people think, feel, and lead.
Aug 18, 2026
Seth Schorr — Chief Executive Officer, Fifth Street Gaming
Filmed in Las Vegas, NV
Long before Seth Schorr became a casino owner and entrepreneur, Steve Wynn sent him to Macau with a pretty unusual assignment: figure out how the market worked.
Aug 11, 2026
Joe O’Connor — Co-Founder, Global Family Home Rentals
Filmed in Buffalo, NY
What if having kids didn’t mean traveling less?
Aug 4, 2026
Amit Brandon Kadosh — Head of Growth, Rex
Filmed in Miami / Fort Lauderdale, FL
When Amit Brandon Kadosh started his company, he wasn’t trying to become a founder. He saw a problem (millions of dollars of food going to waste) & decided to solve it.
Aug 3, 2026
Germán Efromovich — Owner / Principal, Synergy Group
Filmed in Miami / Fort Lauderdale, FL
When you meet someone who has built companies across aviation, oil and gas, shipbuilding, and hospitality, you expect them to have one defining story - the moment that changed everything.
Jul 21, 2026
Zara Ali — Founder, Clover Street Partners
Filmed in New York, NY
The future of work isn’t just changing…it’s becoming increasingly uncomfortable.
Jul 14, 2026
Elena Levine — Founder & Managing Partner, Forcoda Ventures
Filmed in Miami / Fort Lauderdale, FL
Elena Levine has spent the last 12 years building technology companies, helping founders bring products to market, and now raising a venture fund focused on AI and fintech.
Jul 7, 2026
Lauren Molenda — Co-Owner, Riveter Design
Filmed in Buffalo, NY
Lauren Molenda, co-owner of Riveter Design, has trekked to Everest Base Camp, summited Kilimanjaro, run a marathon through the Alps, and spent years intentionally putting herself in uncomfortable situations.
Jun 29, 2026
Harry Leider — Physician executive & healthcare advisor; CMO, Nsight Health
Filmed in Miami / Fort Lauderdale, FL
What do you do when something feels wrong but everyone else seems convinced it’s right?
Jun 23, 2026
Christian Caryl — Journalist, author & former International Op-Ed Editor, The Washington Post
Filmed in Washington, DC
Most people experience history through headlines. Christian Caryl experienced it firsthand.
Jun 16, 2026
Tatiana Fofonova — Co-Founder & Chief Executive Officer, Koda Health
Filmed in Nashville, TN
The most dangerous part of Tatiana Fofonova's trek through Nepal wasn't the mountain.
Jun 9, 2026
Craig Weatherup — Former Chairman & CEO, Pepsi Bottling Group (retired executive)
Filmed in Syracuse, NY
Craig Weatherup spent nearly 30 years at Pepsi, rising to become CEO of Pepsi-Cola North America and later Chairman and CEO of the Pepsi Bottling Group.
May 25, 2026
Keyonna Taylor — Founder & CEO, Key Focus Group
Filmed in Orlando, FL
On this episode of Risky Routes, Olivia sits down with Keyonna Taylor to discuss the parallels between travel, entrepreneurship, and adaptability.
May 18, 2026
Dorte Krogh — Independent leadership advisor, culture strategist & board member
Filmed in Copenhagen, Denmark
On this episode of Risky Routes, Olivia sits down with Dorte Krogh for a conversation about fear, reinvention, nature, and the power of stepping into discomfort.
May 11, 2026
Jennifer Sertl — Founder & President, Agility3R
Filmed in Rochester, NY
On this episode of Risky Routes, Olivia sits down with Jennifer Sertl for an honest conversation about ambition, identity, entrepreneurship, and family.
May 4, 2026
Brett Miller — Founder, CutPeak Energy; Director of Business Development, Renua Energy
Filmed in Albany, NY
A riot, a locked gate, and a split-second decision that could have meant life or death.
Apr 27, 2026
Adrian Erlinger — Director, Data Strategy Lab
Filmed in Washington, DC
A $2,500 honeymoon, a one-way leap into the unknown, and a front-row seat to political upheaval.
Apr 20, 2026
Leslie Woodward — Founder & CEO, Edenesque
Filmed in Hudson Valley, NY
She spent years dreaming about climbing Kilimanjaro through setbacks, surgery, and doubt until she finally stood above the clouds.
Apr 13, 2026
Otto Pohl — Founder, Core Communications; fractional communications leader
Filmed in Bozeman, MT
A 22-year-old with no plan moves to post-Soviet Moscow. What starts as a reckless, “nothing to lose” decision turns into a front-row seat to one of the most chaotic moments in modern history and nearly costs him his life.
Apr 6, 2026
Clark Dever — Co-Founder & Board Chair, BootSector; startup ecosystem builder
Filmed in Austin, TX
He quit his job, spent his savings, and flew to 30 cities in 30 days during a recession with no real plan beyond documenting the moment.
Mar 30, 2026
Tony Coretto — Managing Director, Strategic Ventures LLC
Filmed in Hudson Valley, NY
He didn’t know where he was going, what he was doing, or why he needed a medical clearance until he found himself snorkeling between tectonic plates in freezing water.
Mar 23, 2026
Daniel Strack — Chief Operating Officer, AMYNA Systems
Filmed in New York, NY
What happens when a Goldman Sachs managing director trades structure for uncertainty and realizes the most important lessons didn’t come from Wall Street, but from a jungle in Thailand?
Mar 16, 2026
Ellie Rusling — Co-Founder & CEO, MicroEra Power
Filmed in Rochester, NY
In this episode of Risky Routes, Olivia Goldstein sits down with Ellie Rusling, CEO and co-founder of MicroEra Power, to unpack the travel story that helped inspire the series itself.
Mar 9, 2026
Milbert Kiggundu-Bentham
Filmed in New York, NY
What starts as a peaceful family getaway to the Ssese Islands on Lake Victoria quickly spirals into one of those travel stories that feels almost too chaotic to be real.
Mar 2, 2026
Rafael Campiz — Vice President, Business Development, SeeMedX
Filmed in Albany, NY
What do you do when you step outside a factory in rural Mexico, lose cell service, and realize you’re stranded on a highway alone, in a suit, with no clear way back?
Feb 23, 2026
Sophia Marshall — Senior Program Manager, Startup Ventures, University at Buffalo
Filmed in Buffalo, NY
In this episode of Risky Routes, host Olivia Goldstein talks with her close friend Sophia Marshall about a moment that forever changed how she approaches risk, travel, and decision-making.
Feb 16, 2026
Ron Skylstad — Founder & Operator, Fieldhouse
Filmed in Cashmere, WA
What happens when burnout pushes you far beyond a reset and straight into the Amazon rainforest?
Tonia O’Connor — Co-Founder, The Kite
Filmed in Saratoga Springs, NY
What happens when you’ve spent decades building a successful career, reached the C-suite, and realize it’s time to do something entirely different?
Woah Vicky — Digital creator, internet personality & recording artist
Filmed in Miami / Fort Lauderdale, FL
Coming soon
Newsletter
Essays and interviews on the psychology of leadership, risk, and building things that last.