Trading Secrets – Ep. 270

Olivia Ferney (Travel with Livii): The Secrets of Luxury Travel, Outrageous Requests, NDAs, Shock-Value $$$, and the Business Behind It All

Podcast: Trading Secrets (Audioboom Studios)
Host: Jason Tartick
Date: December 22, 2025

Episode Overview

In this electrifying episode, Jason Tartick sits down with Olivia Ferney, best known as “Travel with Livii,” a viral travel creator who has blown up for her unprecedented transparency about the luxury travel industry. Olivia discusses the business mechanics and client psychology behind luxury travel, shares jaw-dropping stories about outrageous requests, explains how networking and NDAs play a role in her day-to-day, and unveils the shocking financial realities behind the world’s wealthiest travelers’ experiences. This episode dives into a rarely-seen universe, giving listeners an “inside the vault” exposé on the costs, demands, and secrets behind top-tier travel.

Main Themes & Structure

• A rare look into the exclusive world of luxury travel—business, psychology, and costs
• How social media (and viral storytelling) have changed the game in high-end hospitality
• Unfiltered discussion about client expectations, dealing with the ultra-wealthy, and career lessons
• Financial, business, and life takeaways for listeners at any income level

Key Discussion Points & Insights

1. The Path to Viral Fame: From Internal Calls to Internet Stardom

• Origin Story: Olivia describes stumbling into virality when she reenacted a wild client call about lime allergies (“the limes story”), not expecting the public’s fascination ([07:07],[07:53]).
  • Quote: "We got off the call one day with a client...and we're laughing a little bit and decided...let's do a reenactment of this call. And we posted it, and it went, yeah, like, mega, mega viral" — Olivia ([07:53])
• Surprising Engagement: She notes an overwhelming public appetite for transparent, humorous, jaw-dropping tales from a world typically sealed off by NDAs and discretion.

2. Understanding Top Tier Travel: What Makes a Luxury Client?

• Business Model:
  • Two parts:
    1. Standard luxury accommodation booking (villas, hotels, etc.)
    2. “Concierge Plus” - an annual retainer model ($60–100K+) for high-touch, full-spectrum planning ([09:33])
• Who Qualifies?:
  • Not based solely on celebrity or wealth
  • Consideration for spending threshold, but primarily looks for respectful, reliable clients ([10:57])
  • Problems with Fame: Many celebrities/“influencers” appear wealthy but often lack actual funds or can be difficult, unreliable clients ([11:22])
    • Quote: “A lot of celebrities look like they have a lot of money and don't have a lot of money... I'm not necessarily going to hire you because of your fame level.” – Olivia ([11:22])
• Fraud Prevention:
  • Strict proof of funds before significant bookings, especially for Concierge Plus ([18:12])
  • Olivia recounts an elaborate wire fraud attempt ([13:57])
    • Quote: "He sent me a fake wire...Altered wire confirmation, which is wire fraud documentation." – Olivia ([14:05])
  • Importance of strong client relationships; many clients become like family

3. The Outrageous Realities: Hospitality at the Highest Level

• Stories from the Front:
  • Requests ranging from “overnighted Birkin bags to Capri” to ordering “a different lobster from a different ocean” ([21:41],[32:55])
    • Quote: “Some clients are just particular about food...if somebody feels like a lobster that they're being served on their private island is not...just not a quality lobster...we'll send a fishing boat out to go get another lobster.” – Olivia ([33:06])
  • Costs for private chef-arranged meals, flying food in, etc.—can be $10,000+ for a single meal.
• NDAs & Secrecy:
  • Must execute high-level discretion, typically signing NDAs before interacting with even an assistant ([21:12])
    • Quote: "I have to sign NDAs before I even talk to, like, the third assistant most times." – Olivia ([21:14])
  • Creative adjustments (“change names, change stories”) to share experiences without violating contracts
• Strains & Humor:
  • Blurred roles between travel planner, therapist, and fixer in client relationships ([22:32],[47:56])
  • Some clients (or their children) receive monthly budgets of $5K–$100K+, sometimes with supplemental “unlimited” black card access ([54:28])

4. How the Money Flows: Pricing and Commission Transparency

• Revenue Streams:
  • Access/Aggregator Model: Leverage global supplier relationships to get bulk (or last-minute) rates, passing on a portion of savings to clients and charging fees ([23:52])
  • Events & Experiences: High-volume, high-touch arrangements (e.g., St. Barts New Year’s accommodations, performances by global stars)
• Eye-Popping Markups:
  • Examples: St. Barts NYE villa—$1,200 off-peak, $50,000+ during New Year’s ([26:09])
    • Art Basel Miami rooms: $400–$500 typically, $6,000–$7,000+ peak period ([26:37])
  • The value for many clients is in access and seamless execution, not penny-pinching

5. Business, Competition, and Social Media’s Impact

• Competition:
  • Olivia claims a unique, family-style approach not replicated by competitors ([43:01])
    • Quote: "I honestly don't think that anybody does what we do. At least not in North America." – Olivia ([43:01])
• Brand & Identity:
  • Not chasing an influencer image; focus is on business value, not just virality ([46:53])
  • Offers extended by hotels and luxury services to “host” her for mutual benefit, expanding her platform
  • Rapid business growth: Doubled revenue over six months; goal to become a millionaire in 2026 ([45:29])
    • Quote: "I'd like to become a millionaire this year. I think we're hopefully on track to do that." – Olivia ([45:29])
• Networking is Everything:
  • At the elite level, access is driven by referrals and relationships—“the rich get richer” ethos ([52:50])
    • Quote: “Network is everything. Everything you see...the rich just keep getting richer...when you're friendly and you're in those circles, people want you to be a part of their businesses.” – Olivia ([52:50])

6. Travel Hacks and Life Advice for All

• Best Value:
  • Book as far in advance as possible—last-minute flight “deals” are no longer common ([55:19])
  • Off-peak travel for luxury at a fraction of the price; e.g., $50K St. Barts villa for $1,200 in off-season ([26:13])
  • Whistler, Canada: Highly recommends for luxury ski experience and value (plus currency advantage) ([30:03])
• Best Brands:
  • Globally, W Hotels and One Hotel praised for consistency and service ([29:13])
  • Standouts: Boutique, independent luxury options like Satai and Faena in Miami Beach ([29:16])

Notable Quotes & Memorable Moments

• On the absurdity of requests:
  "We have people that spend 200 to $300,000 for like New Year's just weekend." — Olivia ([25:52])
• On the importance of discretion:
  “I have to sign NDAs before I even talk to, like, the third assistant most times.” — Olivia ([21:14])
• On her role as a therapist:
  “A lot of my job is family therapist...a lot of these people sometimes just need to chat and that's honestly everybody." — Olivia ([47:56])
• On luxury markups:
  “So you're talking about a potential 50x markup.” — Jason ([26:13])
• On best client relationships:
  "Two of our wealthiest clients are my favorite human beings on planet Earth. They are gracious, they are so thankful..." — Olivia ([49:33])
• On what brings happiness:
  "I think that money can bring you happiness. But people that take the time to pause and say, like, oh damn, I did that...those people are a lot happier." — Olivia ([51:45])
• On competition:
  “I don't think we have competition.” — Olivia ([43:01])

Quickfire (Rapid Fire) Segment Highlights ([56:01])

• Favorite US destination: New Orleans ([56:04])
• Best US restaurant: Cote (NYC & Vegas locations) ([56:33])
• Preferred airline: American Airlines (points) ([56:48])
• Best credit card for travelers: AMEX Platinum ([57:01])
• Favorite event booked: F1 Vegas, Super Bowl ([57:11])
• Her impossible luxury travel “grammy”: Be the “celebrity travel agent”—the go-to for the ultra-wealthy ([57:51])

Actionable Lessons & ‘Trading Secrets’

• For Listeners: Luxury Can Be Had...With Timing
  • Book off-peak, plan far ahead, and use rewards credit cards to access luxury experiences without the luxury price tag ([26:13],[55:19])
• For Entrepreneurs:
  • Relentless networking and relationships are the key to gaining access in elite markets
• For Women/Young Professionals:
  • “Just get your butt out there and you just keep trying.” Failure is part of the journey; belief in yourself and not giving up creates luck and opportunity ([59:35])

Timestamps for Key Segments

| Topic | Timestamp |
|---|---|
| Olivia’s viral journey, “the limes” story | 07:07–08:48
| Client selection and the realities of celebrities/influencers | 10:57–12:24
| Fraud attempts, proof of funds | 12:50–14:34; 17:03–18:46
| Concierge Plus & high-touch business model | 18:59–19:51
| Insanity of requests (Birkin bags, lobsters, etc.) | 21:41–34:08
| Room rate markups (St Barts, Art Basel, etc.) | 25:25–26:37
| Travel hacks for mere mortals | 26:37–27:30; 55:19
| NDAs & secrecy in luxury travel | 21:09–22:03
| Handling the world’s wealthiest children’s budgets | 54:23–55:01
| Social media, business growth, and future plans | 45:29–46:53
| Rapid fire (favorite city, event, perks, etc.) | 56:01–57:36
| Trading Secret (Olivia’s advice) | 59:35–60:03

Recap & Reflection (w/ Jason and David, “The Curious Canadian”)

Jason and David debrief on the realities and trade-offs of extreme wealth and luxury travel, sharing stories from David’s years working for a billionaire. Both are fascinated (and sometimes skeptical) about whether money brings more happiness or more problems—a theme debated throughout the episode.

Best Quote from the Recap:
"My job is not to judge, it’s to execute.” – Olivia (cited by David, [63:21])

Further Information

Find Olivia (“Travel with Livii”):

• IG: @travelwithlivii (LIVII)
• Company: Top Tier Travel

Conclusion

This episode unpacks the glamor, challenges, and absurdities behind ultra-luxury travel, giving both aspirational and practical lessons—whether you’re dreaming of New Year’s in St. Barts or just after a hotel upgrade. Olivia’s unfiltered insights and stories make this a can't-miss exploration into a world few will ever truly see.

Trading Secret Takeaway: Belief and perseverance push you into rarefied circles—the best access, the best clients, and the best opportunities all start with a willingness to “just show up and keep trying”…no matter how elite the world you want to break into might seem.