Real Estate Rookie Podcast: "He 'Stacked' 5 Properties in 6 Years: Now He Lives and Travels for Free!"

Date: December 8, 2025
Hosts: Ashley Kehr & Tony J Robinson
Guest: Ross Elkhorn

Episode Overview

This episode features Ross Elkhorn, who transformed a high-earning, high-tax W2 income into financial freedom through savvy real estate investing and travel hacking with credit card points. Ross shares his journey from the pain of a $33,000 tax bill to building a five-property portfolio—including creative house hacks and land deals—and reveals how he uses credit strategies to travel first class for free. The discussion is packed with actionable advice for new investors, emphasizing taking action over analysis paralysis, learning from mentors, and strategic partnership building.

Key Discussion Points & Insights

1. Ross’s "Tax Wake-Up Call" and Wealth Shift

• Turning point: In 2018, Ross faced a $33K tax bill despite solid income and index fund investments. This became the catalyst for seeking wealth-building alternatives.

  "I was like, okay, what's going on here? ...real estate was a great way to shelter that." (Ross, 01:08)

• Lesson: Real estate isn’t just about cash flow—long-term tax advantages and equity matter, especially for high earners.
• Key advice:

  “One of the real unlocks in real estate investing … is the ability to reduce your taxable income by half or even more.” (Tony, 03:53)

2. Mindset Evolution and Real Estate Education

• Shifting beliefs: Ross credits a business partner from a real estate family for steering him to real estate books like Flip Your Future and The ABCs of Real Estate Investing.

  “It wasn't just saying, okay, I'm going all in. It was just diving deeper, doing the research...” (Ross, 08:02)

• Quote:

  “Well-intentioned advice can be bad advice.” (Tony, 09:12)

3. House Hacking: Action Over Analysis

• First deal: Ross bought his first house hack via FaceTime in Charlotte while living in Northern Virginia, leveraging market research and his network for confidence.

  “Not having analysis paralysis, right? Taking action, I think, is the biggest thing.” (Ross, 14:17)

• Strategy: Secured roommate to help with the mortgage, built trust with a lender, and prioritized flexibility for future rentals.

4. Scaling Up: Momentum, Partnerships, and Lakefront Land

• Second and third properties: Used profits and networking to expand. Ross and his partner bought a new construction property and a waterfront lot (negotiated down from $300K to $270K).
• Funding:
  • Invested 10% of every W2 paycheck in employer stock, which he doubled and used for down payments.
  • Utilized a HELOC on his first property.

  “It gave me the confidence of, okay, Charlotte's a good market. Having conversations with other people, starting to network with the right people...” (Ross, 18:01)

5. Partnerships: Building for Trust and Longevity

• Foundation: Four-year relationship with business partner before buying the first property.
• Best practices:

  “The first thing is…you always want to be aligned with your partner on trust. That's the number one thing.” (Ross, 25:50)

• Weekly communication: Tuesday 5pm calls to ensure alignment.
• Structure: Both contribute 50% down; both are on the deed, with options for transferring to an LLC.

6. Credit Card Points & Travel Hacking for Investors

• What is travel hacking? Using credit card welcome bonuses/points for travel or business expenses.

• Safe credit use:

  • Use 0% cards for large expenses (furnishings, rehabs, etc.).
  • Set up autopay for at least minimum payments.

  “My suggestion is…get the cards that have the right amount of points…if you want to have just an additional float, you know, a little bit of leverage.” (Ross, 32:57)

• Real-world example:

  • Used Chase Business Unlimited Ink for a 100k-point bonus.
  • Points funded $5,600 Qatar Airways business class flights for his honeymoon.

• For Partnerships:

  • Points split equally at year-end; Chase allows point transfers between business partners on the same card/deed.

• Tools for tracking:

  • AwardWallet and CardPointers recommended for managing cards, points, and offers.

  “If you want it simple, stay with one bank makes it easy…But I recommend Chase, Capital One, Amex…” (Ross, 37:33)

7. Paying Vendors When They Don’t Take Cards

• Third-party apps:
  • Melio for business transactions.
  • Plastiq for personal payments, both with a 2.9% fee.
• Tax write-off: The fee can often be business-expensed.
• Negotiation tip: Sometimes you can get vendors to cut ACH fees, then pay via card/Plastiq and come out even—plus points.

  "Everything's negotiable, as you guys know." (Ross, 42:01)

Memorable Quotes & Moments

• On Life Lessons:

  “I wish I worked less. I wish I invested earlier. I wish I traveled more.” (Ross recounting mentor advice, 11:29)

• On Taking the First Step:

  “So many people…like, oh, I wish I bought in 2020… and they wait and then they got a rate that's double what I got on two properties, because [I] took that leap…” (Ross, 14:17)

• On Partnership Dynamics:

  “Ideally, you want to date a little bit before you jump into something.” (Tony, 27:52)

• On Creative Funding:

  “If you’re already paying via ACH, you could say, hey, I’m going to pay it with a card. …and then go back and say…take that 3% fee off…” (Ross, 42:01)

• On Using Points to Build Memories:

  “It's not just like, oh, we're getting the best deal… It's like, no, they create actual cool memories...” (Ross, 46:40)

Timestamps for Key Segments

• Tax bill and wealth-building “aha”: 01:08–04:45
• Mindset, mentors, first books: 06:43–08:02
• First house hack (FaceTime buy, overcoming analysis paralysis): 10:33–14:57
• Scaling: Lakefront land, creative dealmaking: 18:01–23:42
• Partnership structures and advice: 25:34–28:42
• Credit card strategies for investors: 32:44–38:55
• Tools for tracking cards & points: 37:33–38:55
• Paying vendors who don’t take cards: 39:16–43:05
• Splitting points in partnerships: 44:18–46:40
• Points for memories (travel, celebrations, family): 46:40–47:05

Conclusion & Resources

Ross's story shows that you don’t have to start big to build wealth through real estate or live a more flexible, adventurous life. Key to his success: learning from real-life mentors, leveraging partnerships based on trust, and making every dollar—tax savings, partnerships, credit rewards—work as hard as possible.

Connect with Ross:

• ItineraryBoss.com – Free points and miles cheat sheet, transfer partner guide, and tools.
• Social: @ItineraryBoss

For aspiring investors:
Ross and the hosts urge rookies to focus on taking action, find mentors who’ve lived the path, and not overlook the “hidden” advantages that aren’t hyped on social media—especially tax strategies and relationships.

To be a guest on the Real Estate Rookie Podcast:
Apply at biggerpockets.com/guest