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  • Chris & John

Ep 79: Embracing Good Luck and Healthy Risk with AJ Ramler

You can have good luck to enter the market at the perfect time but luck is nothing without the grit to take action and embrace risk. Today we talk with investor AJ Rambler who has made the most of his good timing to make sound investments. We open the conversation by chatting with AJ about how he began house-hacking in 2012 before the strategy became popular. AJ’s story reflects a lot of ours, and we discuss the slow grind that it takes to land your first deals on a minimal income. On the topic of first deals, AJ shares the key mistakes that he often sees beginners make when they get caught up in the excitement of investing. He emphasizes the importance of underwriting correctly and why you need to be extremely picky with your deals — especially as there are many ways to kill your cash flow. After AJ talks about what he looks for in a deal, he opens up about his experiences incurring a huge expense on his first property. He reveals his takeaway that with a cool head and the right insurance, any catastrophe can be managed. We ask AJ about how he began exploring other real estate niches when presented with good deals, a strategy that he wouldn't normally recommend to other investors. Near the end of the episode, we chat about affordable housing, office spaces, and how the pandemic has affected his business. Tune in to hear more about AJ’s investments and how he capitalized on his good timing.

Key Points From This Episode:

  • From house flipping to multifamily syndication, hear about AJ’s journey into real estate.

  • How AJ got into house hacking in 2012 — before it became well-known.

  • The slow grind from your first deal to your second and reaching a point of compound success.

  • Challenges using the BRRRR and refinancing strategy to build more deals.

  • The key mistake that beginners make; not underwriting deals correctly.

  • AJ’s rule; his mortgage should be 30% to 35% of the rental income.

  • Why your deal should be extraordinary to make any money off of it.

  • AJ’s experience encountering a huge expense with his first property.

  • Why you need to “hammer” insurance companies in negotiations.

  • Using an adjuster to push up claims and get more money out of insurance claims.

  • When AJ began expanding into multifamily and commercial properties.

  • Why managing affordable housing is challenging and that it can pay well.

  • What led AJ to explore other real estate niches.

  • How AJ fell into office space and why he isn’t a fan of the model.

  • Hear how the pandemic has affected AJ’s business.

  • Why good luck is useless without the ability to take action and embrace risks.


“The huge mistake that I see people make in the beginning is not underwriting deals correctly, not accounting for expenses that are gonna be there.” — AJ Ramler [0:12:19]

“I wish that it was pushed more — your deal has to look smoking hot for it to make money at the end of the day.” — AJ Ramler [0:14:18]

“All the stuff that people say about affordable housing is true. It’s a ton of work. You’re dealing with random maintenance and evictions all the time.” — AJ Ramler [0:31:45]

“You have to like risk, to a certain degree, to be in the real estate business. Even if it isn’t risky, it always feels risky.” — AJ Ramler [0:47:15]

Links Mentioned in Today’s Episode:

AJ Ramler

AJ Ramler Instagram

Proxy Properties




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