Welcome to Risky Routes, a short interview series telling the stories of moments when travel forces you to grow up and adapt fast. Because risk creates perspective. And perspective creates success. We talk about the chaotic, uncomfortable, borderline-bad-idea journeys that pushed people to level up, trust themselves, and take control of their lives.
Why a Struggling Actor Became a Serial Founder with Michel Bayan, Serial Entrepreneur & Advisor at GeoSgip
Michel Bayan (https://www.linkedin.com/in/michelbayan/) 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. He discovered venture capital by accident and closed his first round with $400 in his bank account. He went on to sell a company to eBay and build an AI business that drove $250M in new revenue before a double exit.
In this episode of Risky Routes, Michel opens up about:
Going from failed actor to tech founder
What selling a company is really like (and why most exits aren’t home runs)
The Silicon Valley founder myth that burns people out
Why your job as a founder isn’t to prove you were right
Life after the exit: becoming a “catalyst for impact” with GeoShip and healthier, $165K homes
What 37 countries taught him about happiness, and why he’s spending his 50th birthday on top of a giant rock in Colombia
Risky Routes is a short interview series with executives and leaders about the chaotic, uncomfortable, borderline-bad-idea journeys that push people to level up, trust themselves, and take control of their lives. Hosted by Olivia Goldstein.
Chapters:
0:00 Intro
0:14 Welcome to Risky Routes
1:30 Meet Michel Bayan
3:14 Yoga teacher to the stars & life as an actor
5:00 “Venture capital? What’s that?”
7:34 Selling Clutch to eBay
9:28 Predicting churn with AI before it was cool
12:00 $250M in new revenue & a double exit
14:03 What founders should know before selling
15:24 The Silicon Valley founder myth
17:13 What comes after the exit
18:42 GeoShip & the toxic truth about houses
21:30 A breast cancer blood test from Brazil
22:16 Rethinking capitalism & company governance
25:25 Should founders raise VC money?
26:37 Your job is to give the market what it wants
28:18 37 countries & no objective reality
31:00 Guatapé & a 50th birthday on a giant rock
32:30 Outro
🎥 Watch on YouTube: youtube.com/@NotPC_VC
📝 Read the story on Substack: oliviagoldstein.substack.com
📲 Follow @notpc_vc
13 Oct 2026
Quitting the C-Suite to Start Her Next Chapter with Tonia O’Connor, Co-Founder of The Kite and former CEO of Chopra Global
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?
Tonia O’Connor (https://www.linkedin.com/in/toniaoconnor/) spent more than 25 years in media and entertainment, helping transform major brands like TV Guide and Univision before making the leap into health and wellness, where she served as CEO of Chopra Global and Tone It Up. But along the way, she discovered something unexpected: she loved building people more than building businesses.
We sat down in Saratoga Springs to talk about the decisions that shaped her career, starting with a family adventure through Colombia that took her far beyond the typical tourist destinations. Her curiosity for the unfamiliar has been a constant throughout her life, including her willingness to walk away from the security of established companies to bet on herself.
Today, as co-founder of The Kite (https://www.kite-labs.com/), Tonia works with CEOs, founders, and leadership teams to help them think bigger and reach their next level.
We explore why the very things that made you successful can eventually hold you back, why imagination is a muscle we need to keep exercising, and how self-awareness, shared values, and accountability can transform teams.
It’s a conversation about reinvention, finding purpose beyond a job title, and having the courage to start a new chapter, even when you’ve already built a successful one.
25 Aug 2026
From Designing Destinations to Developing Leaders with Kimberly Trueba, CEO, Girl Scouts of Southern Nevada & former Disney Imagineer
Kimberly Trueba (https://www.linkedin.com/in/kimberly-trueba-8a0bb78/) has built a career around one core idea: the environments we create shape how people think, feel, and lead.
Today, she is the CEO of Girl Scouts of Southern Nevada (https://www.girlscoutsnv.org/). Before that, she spent more than a decade at Walt Disney Imagineering, then went on to build a design firm working on hospitality and lifestyle projects around the world.
In this episode of Risky Routes, Kimberly shares how those experiences shaped her approach to leadership, decision-making, creativity, and risk.
We talk about the question that helped open the door to Disney, what she learned from working alongside world-class architects and designers, and why some of her most valuable leadership lessons came from simply observing people and understanding how they experience a space.
Kimberly also shares how working across different countries and cultures expanded the way she thinks about experience design, why curiosity remains one of the most important qualities for any leader, and how she carried those lessons into her work with Girl Scouts of Southern Nevada.
We also get into confidence, taking calculated risks, building a personal board of directors, creating opportunities for the next generation, and why exposure to new people, places, and experiences can fundamentally expand what someone believes is possible.
It’s a conversation about leadership, creativity, and the experiences that shape the way we see the world.
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