Real Estate Rookie Podcast Episode Summary

Podcast: Real Estate Rookie
Hosts: Ashley Kehr & Tony J. Robinson (BiggerPockets)
Episode: "6 Rentals in 5 Years and Fast-Tracking Financial Freedom"
Guest: Dean Pinhas
Date: August 18, 2025

Episode Overview

This episode offers a candid conversation with Dean Pinhas, who built a six-property rental portfolio in just five years, starting by forgoing a traditional wedding to buy his first property. Dean shares his unconventional approach to building wealth through real estate—focusing on fast-tracking financial freedom through long-term strategies, intentional sacrifices, and managing rentals from a distance. The hosts encourage listeners to embrace unique paths, discussing the real emotions, risks, and rewards along the way, making this episode especially relatable for aspiring or early-stage investors.

Key Discussion Points and Insights

1. Trading Wedding Bells for Wealth (00:36–02:21)

• Dean began his journey by using his and his wife’s wedding budget as a down payment on their first house.
• Dean's perspective: Neither he nor his wife craved a big wedding and prioritized setting themselves up for financial success instead.
• Family and friend reactions were mostly positive and even admiring once they explained their choice.
• Memorable Quote:

  "Everyone's reaction is pretty much universally like, wow, that's so smart. Like, I should have done that."
  — Dean (01:40)

2. Going Against the Grain—Making Unconventional Choices (02:21–06:11)

• The discussion extends to how building wealth through real estate is often perceived as “unusual.”
• The hosts encourage listeners to block out advice from people whose values don’t align with their own financial goals.
• Storytime includes examples of others making extreme but strategic sacrifices (house hacking, living out of a car, driving a clunker) to get ahead.
• Ashley’s advice:

  "You really have to think about why you're going to do something or why you're still doing something. Is it because of what other people will think, or is it because it's truly what you want to do?"
  — Ashley (04:24)

3. From Federal Reserve to Full-Time Real Estate (06:11–09:22)

• Dean describes feeling stuck in his government job, yearning for a career that matched his confidence and ambition.
• He credits hard work, luck, and supportive family connections as keys to making the leap.
• Dean obtained his real estate license before switching careers and ultimately moved to Los Angeles for better earning potential.
• Initially, Dean's real estate journey began after this career leap; the decision was more about creating future opportunity than side-hustling.

4. Family Influence—And Caution (09:00–10:58)

• Dean’s family background included owning and renting multiple properties, which showed him real estate’s potential.
• Ironically, his father became increasingly risk-averse after the 2008 crisis and now warns Dean to diversify instead of doubling down on real estate.
• Memorable Quote:

  "My dad was very much against me pursuing real estate investment...he cautioned me against it...so actually I had a lot of pushback from my family from pursuing that as well."
  — Dean (09:22)

5. The Move to Los Angeles—Following Opportunity (15:00–19:59)

• A chance family visit and a glimpse of his uncle's financial success in LA inspired Dean to relocate for higher income.
• Dean took a leap of faith, quitting his stable Federal Reserve job without a long-term safety net.
• The move coincided with the start of the COVID-19 pandemic, increasing the stakes.
• Dean describes himself as “naturally risk-averse,” but motivated by a sense of “desperation to get ahead.”
• Dean's reflection:

  "In hindsight, it’s actually not my personality at all. I’m a very conservative, not a risk taker person...but it gave me the courage to do it again."
  — Dean (18:35)

6. Long-Distance Landlording & Scaling Up (21:18–24:04)

• Rented out their Kansas City property after moving to LA—faster and more smoothly than Dean expected.
• His wife plays a key role in identifying and approving investment properties.
• Strategy shifted toward buying multiple rentals with the profits and increased income from LA.

7. Financing Strategy—Paying to Lose (On Purpose) (22:51–29:38)

• Dean and his wife buy every rental with 25% down and 15-year mortgages, intentionally accepting negative cash flow.
• They view the monthly losses (from $200 up to $900/property) as fast-tracking financial freedom and wealth via forced savings, equity, and appreciation.
• Dean’s reasoning:

  "I want to lose the money now, I want to invest the money now so that I can enjoy it more quickly later on."
  — Dean (24:24)

• Tony’s summary:

  "Everyone has a different motivation for investing in real estate, and you’ve got to understand what yours is in order for you to make the best move for you and for your future."
  — Tony (25:53)

8. Equity, Appreciation, and the Real Wealth-Builders (26:46–29:41)

• Dean tracks the total mortgage outlay, current portfolio value (~$2.5 million), and projects when properties will be fully owned and lucrative.
• The panel underscores how the real wealth in real estate comes from equity and appreciation over time more than immediate cash flow alone.
• Ashley’s insight:

  "It’s the equity and the appreciation in the property, that’s the real wealth builder...all of that equity, that’s what is building wealth for me."
  — Ashley (28:16)

9. Treating Rentals Like a True Business (29:12–30:11)

• Dean frames his real estate acquisition and loss model as akin to operating a business, noting that most startups operate at a loss before becoming profitable.
• He highlights the time and work required to self-manage six rentals, even with a “passive” investment.

10. Portfolio Breakdown & Property Types (30:33–32:47)

• All six rentals are in Kansas City suburbs (Overland Park, Fairway, Prairie Village), each a single-family home but with varying sizes/configurations.
• Lessons learned: One-bathroom homes limit prospective tenants; larger homes are easier to rent and turnover.

11. Rehab Lessons & Turnkey Temptations (36:58–41:04)

• Despite his construction expertise, Dean regrets over-renovating lower-end rentals, with expensive upgrades not producing commensurate rent bumps.
• There are pitfalls in underestimating contractor headaches—cost overruns, shoddy work, and wasted effort.
• Current preference: Buy more turnkey properties, minimizing renovation risks and maximizing ease.
• Dean’s learning:

  "I think there was more emotion that went into it than logic...you quickly find yourself spending thousands of dollars on a project and you look at it and you go, wow, it’s beautiful. But then in hindsight, how much more rent did that get you?"
  — Dean (37:09)

12. Defining Success (42:52–43:28)

• For Dean, success in real estate is about financial freedom and providing a comfortable, flexible life for his family—not portfolio size.
• Dean’s definition:

  "I just want to be able to do whatever I want, whenever I want to do it...Success for me is just giving my family a comfortable life that we all want to enjoy."
  — Dean (42:52)

Notable Quotes & Timestamps

• “Everyone’s reaction is pretty much universally like, wow, that’s so smart. Like, I should have done that.”
  — Dean (01:40)

• “You really have to think about why you're going to do something...is it because of what other people will think, or is it because it's truly what you want to do?”
  — Ashley (04:24)

• “My dad was very much against me pursuing real estate investment...he cautioned me against it.”
  — Dean (09:22)

• “In hindsight, it’s actually not my personality at all. I’m a very conservative, not a risk taker person.”
  — Dean (18:35)

• “I want to lose the money now, I want to invest the money now so that I can enjoy it more quickly later on.”
  — Dean (24:24)

• “It’s the equity and the appreciation in the property, that’s the real wealth builder…all of that equity, that’s what is building wealth for me.”
  — Ashley (28:16)

• "I just want to be able to do whatever I want, whenever I want to do it…Success for me is just giving my family a comfortable life that we all want to enjoy."
  — Dean (42:52)

Timestamps for Key Segments

• 00:36–02:21: Wedding-for-rental swap story, family reactions
• 06:11–09:22: Quitting the Fed, leap into real estate
• 15:00–19:59: LA move, motivation, early struggles
• 22:51–29:41: 15-year notes, intentional negative cash flow, wealth building
• 36:58–41:04: Rehab lessons, finding the balance between upgrades and ROI
• 42:52–43:28: Defining real estate success

Takeaways for Listeners

• There is no single “right” path in real estate—success looks different for everyone.
• Be honest about why you want to invest, what you’re willing to sacrifice, and how you define “enough.”
• Don’t let societal norms dictate your progress; unconventional choices can accelerate your timeline.
• Know your exit strategy and keep long-term wealth and freedom front and center, even if it means short-term losses.
• Experience, not just logic or emotion, shapes the best investing decisions.

To connect with Dean:
Website: homebuilding.com
Instagram: @homebuildDean