Podcast Summary: Real Estate Without Borders

Episode: How a 20-year old scaled a million-dollar Airbnb Portfolio
Date: September 9, 2025
Host: Real Estate Without Borders (Dave)
Guest: Robin (Royal Oak Retreat co-founder)

Overview

This episode features Robin, a 20-something entrepreneur who, along with his business partner Renzo, is building a luxury cabin micro-resort called Royal Oak Retreat in Virginia. Robin shares how he transitioned from sneaker-flipping in high school to real estate development, the inspiration behind their high-end Airbnb concept, navigating unexpected challenges, and leveraging social media to drive both branding and direct bookings. The conversation is packed with actionable insights for young, ambitious investors—especially those interested in the intersection of real estate, wellness, and content creation.

Key Discussion Points & Insights

1. Robin’s Story & Real Estate Origins

• From Sneaker Flipping to Real Estate:
  • Started entrepreneurial journey reselling shoes in high school, inspired by Gary Vee (03:48).
  • Sold shoes during COVID, transitioned to finance studies at UVA, and interned with J.P. Morgan (04:53-05:05).
  • Bought first investment property at age 21, thanks to guidance from a UVA alum agent (06:13-06:42).
• The Renzo Connection:
  • Reconnected with Renzo, an old tennis friend, who had real estate development experience (05:14-06:13).
  • Renzo pitched the idea of developing a high-end Airbnb; Robin invested $40K after due diligence (06:44-07:27).

2. Building the Vision: Royal Oak Retreat

• Project Background:
  • Luxury cabin “micro-resort” in Front Royal, VA (00:28-00:39).
  • Aims to create a health and wellness retreat, aspiring to franchise the concept across the East Coast.
• Social Media Impact:
  • Grown to 450,000 followers by documenting the build process (00:39-01:35).
  • Robin: “We gotta get some new blood in here... start yelling in the camera. We gotta start doing this cool stuff, man, for sure.” (01:44)
• Roles & Team:
  • Robin leads marketing/social presence; Renzo commands construction/vision (02:33-03:15).
• Design Inspiration:
  • Modeled after Isaac French’s Live Oak Lake project in Waco, TX (09:30-09:56).
  • Purchased architectural plans directly, customizing for their own site and aesthetic (09:42-10:42).
  • Key insight: Direct booking funnel via social media added $2M of value to Live Oak Lake’s $7M exit (10:42).

3. Location, Market Analysis & Niche Targeting

• Why Front Royal, VA?
  • Both founders are native Virginians; wanted to be present for their first build (11:52-11:56).
  • Proximity to Shenandoah National Park—a recognized regional vacation/rental destination (11:56-13:14).
  • “Washington D.C. is the number one remote… workers in America. We could not only dominate the weekends, we could do the weekdays too.” (13:15)
• Clientele & Wellness Focus:
  • Pivoted to cater to the booming health and wellness economy, after a viral Twitter-inspired post (13:41-14:04).
  • Interaction with major wellness brands and influencers—including FIT Insider and Kyrie Irving (14:04).
  • “Why can’t we make this a thing?… This is like where Gen Z is going.” (14:04-15:02)

4. Development Process, Challenges & Learnings

• Due Diligence & Permitting:
  • 60-day land contingency: studied buildability, septics, soils, setbacks (07:27-08:56).
  • Navigating local regulations and ongoing short term rental permit hearings (16:36-17:10).
  • Social media both helped and brought unwanted attention to permitting (16:48-17:00).
• Unit Details:
  • Four subdivided lots; first cabin is 2 bedrooms/1,000 sq ft (17:19-17:27).
  • Each unit planned as a unique “experience” on half an acre, primarily couples/friends’ retreats (17:38).
• Biggest Surprise:
  • Unexpected global tariffs nearly derailed completion; imported windows from Poland caught in international trade issues, causing months of delays (19:29-21:07).
  • “I have never, ever studied politics ever until the tariffs thing… economic policy, how much it can affect a small cabin that you’re building. I was like, bro, what?” (20:54)

5. Scaling, Exit Strategy & The Power of Social Attention

• Evolving Endgame:
  • Original plan: build, operate for five years, then potentially sell (21:26-22:36).
  • Now open to shorter horizons if the right offer comes:
    • “If someone offered 2 million and it’s before it's even built, I’d be an idiot not to take it.” (23:55)
  • Inbound interest from high-net-worth buyers, investors, larger project invitations (23:07-24:18).
• Social Leverage:
  • “With social media, like… all these new things are coming in my way… short term goals only now.” (23:07)
• Consistency in Content:
  • Posting daily for 30 days—“probably the hardest thing I’ve ever done” (25:34-26:20).
  • Robin is a “one man show” running all social accounts (26:24).

6. Advice For Aspiring Young Investors

• Lessons from Robin’s Experience:
  • “I had a 2.9 GPA… Are you willing to put your balls on the line is like the question…” (27:23)
  • Learning from failures in entrepreneurship is as valuable as success; risk is necessary (28:52).
  • On support and risk:
    • “[My dad said] you gotta go all in on one… You’re gonna be bad at your banking job or you’re gonna be bad at this. You gotta choose one so you can be good at the one thing that you do.” (28:28)

Notable Quotes & Memorable Moments

• On blending story and brand:
  • “We gotta start doing this cool stuff, man, for sure. I think the real estate game could really get some juice.” (01:44, Robin)
• On replicable models:
  • “Isaac French built seven cabins for 2.1 million. Eighteen months after he launched, he sold it for $7 million.” (10:07, Robin)
  • “A huge part of Isaac French’s sale was that he… had this huge social media following… They valued the funnel at 2 million.” (10:42, Robin)
• On the health/wellness pivot:
  • “Wellness real estate is like a billion dollar industry… This is like where Gen Z is going. This is the shift.” (14:04-15:02, Robin)
• On unpredictable learnings:
  • “I have never, ever studied politics ever until the tariffs thing… We couldn’t even track our windows for two months.” (19:29-20:54, Robin)
• On opportunity & flexibility:
  • “It’s hard for me to have a five year vision when all these new things are coming in my way… short term goals only now.” (23:08, Robin)
• On entrepreneurial mindset:
  • “Are you willing to put your balls on the line is like the question… If you fail, you know how much you learn.” (27:23, Robin)

Important Timestamps

| Timestamp | Topic | |---|---| | 00:28 | Robin introduces Royal Oak Retreat; crowd-sourced luxury, documenting journey | | 03:48 | Robin’s entrepreneurship origins; shoe reselling during COVID | | 06:13 | First real estate purchase at 21, then transition to development | | 09:30 | Inspiration from Live Oak Lake & buying architecture plans | | 11:52 | Why Virginia? Market research and personal connection | | 13:41 | Pivot to health/wellness branding following viral social post | | 16:36 | Local permitting challenges—short-term rental hearings | | 17:19 | Details of property size & experiential design philosophy | | 19:29 | Biggest learning: International tariffs & unexpected development delays | | 21:26 | Endgame: operate or sell? How social media brings new opportunities | | 25:34 | Social media grind: 30-day posting challenge, solo content creation | | 27:23 | Advice for young entrepreneurs: risk, failure, family influence |

Social & Project Links

• Robin’s Instagram: @chida.rajan
• Royal Oak Retreat: @royaloakretreat
• Partner: @sanyo_renzo

Tone & Takeaways

Robin is candid, energetic, humble, and filled with hustle—his experience is a testament to Gen Z’s creative, risk-tolerant approach to both real estate and business. The episode offers an inspiring blueprint for young people to get into property investing, especially those interested in new asset classes (like wellness retreats), social media-based growth, and leveraging global models to local markets.

End of Summary