Unpopular Opinion: Most Real Estate Investors Aren't Actually Good at Investing.

Austin Shaner · 2026-10-14T15:10:12-07:00

I work with real estate investors in the Philadelphia market every day, and one thing I've noticed is how many people call themselves investors but don't seem to know what actually makes a deal worth buying.Some people won't touch a property unless it's practically being given away. Others will spend $200K renovating a house without understanding what the neighborhood can realistically support.Meanwhile, some of the most successful investors I've encountered aren't chasing home runs. They're buying properties with reasonable margins, managing their renovations, and putting their money back to work.It's made me wonder:Is finding a great deal actually the most important skill in real estate investing? Or is being able to execute on an average deal what separates successful investors from everyone else?I'm curious what experienced investors think. What's the biggest mistake you see other investors making?

Jay HinrichsBusiness Member

Real Estate Consultant · Summerlin, NV · Member since 2014 · 45k+ posts · 66k+ votes

13h

I will be the first to admit I am very poor at landlording. I fall for every sob story etc.. Its not in DNA to be tough as nail landlord ( which you need to be if your going to work in a City like Philly.

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Joseph ScoreseBusiness Member

Banker · Philadelphia · Member since 2009 · 2k+ posts · 634 votes

10h

Austin, great perspective, and I agree with much of what you're saying.

Having worked with real estate investors throughout Philadelphia and the surrounding markets, I've learned that finding a good deal and knowing how to execute are two very different skill sets.

As a nationwide direct private lender, I see investors focus heavily on acquisition price and potential ARV while overlooking financing costs, holding expenses, renovation timelines, cash flow, and their overall exit strategy.

In my opinion, the biggest mistake investors make is confusing a profitable projection with a profitable investment.

A property purchased at a deep discount can still become a financial disaster through poor execution. Conversely, an average deal with realistic numbers, disciplined renovations, appropriate financing, and a clearly defined exit strategy can generate consistent returns.

The most successful investors I've worked with understand that real estate investing isn't about hitting a home run on every transaction. It's about protecting capital, managing risk, maintaining liquidity, and consistently putting money back to work.

Acquisition creates the opportunity. Execution determines the outcome. Capital management builds long-term wealth.

Great discussion, Austin. These are exactly the conversations more investors need to be having.

Joseph V. Scorese
Senior Vice President of Business Development | Built Lending
Nationwide Direct Private Lender

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Divin KanyamaBusiness Member

Accountant · Seattle, WA · Member since 2025 · 421 posts · 167 votes

7h

@Austin Shaner A great deal certainly helps, but execution is usually what determines whether the projected return becomes real. An average deal with a realistic scope, disciplined budget, reliable contractors, appropriate financing, and a clear exit can outperform a deeper discount that is poorly managed. The strongest investors are often not waiting for a perfect opportunity; they are buying with enough margin for error and consistently completing the plan.

The biggest mistake is probably confusing activity with investing—overpaying to win a deal, renovating beyond what the neighborhood supports, underestimating time and carrying costs, or relying on appreciation to rescue weak numbers. On the other side, analysis paralysis can be just as costly when someone rejects every reasonable deal because it is not a home run. Good underwriting gets an investor into the right range, but execution, risk management, and repeatability are what build a durable portfolio. Finding a deal and operating it well are both important; the real advantage is knowing what can be controlled and leaving enough cushion for what cannot.

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Ashish AcharyaBusiness Member

CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes

4h

Austin, I think finding a good deal is important, but being able to underwrite it honestly and execute on it is probably what separates the investors who consistently do well. I’d add one more piece to the equation: the after-tax return.

A property can look great based on the purchase price and projected resale or rental income, but once you factor in financing, holding costs, repairs, CapEx, depreciation, and the eventual tax consequences, the picture can change pretty quickly. I also think one of the biggest mistakes is trying to make a deal work because you really want to buy something. If the numbers only work with the highest ARV, lowest rehab estimate, and perfect timeline, it probably isn't a great deal.

For me, the skill is being able to say “no” to a deal that looks exciting but doesn't make sense on conservative numbers, and then being ready to move quickly when one actually does. Feel free to DM me, I’d be happy to send over a few resources that might be helpful.

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Unpopular Opinion: Most Real Estate Investors Aren't Actually Good at Investing.

Unpopular Opinion: Most Real Estate Investors Aren't Actually Good at Investing.

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