The Investor “Happy Hour” Most People Skip (But Shouldn’t)

The Investor “Happy Hour” Most People Skip (But Shouldn’t)

Member since 2026 · 7 posts · 3 votes

One thing I’ve noticed when people start exploring real estate investing is that many jump straight into looking at deals.

They start reviewing opportunities, comparing returns, and evaluating operators……but they haven’t taken the time to define their own investment criteria first.

Before seriously evaluating opportunities, I always recommend investors have a quick “Investment Happy Hour.” This can be with:

• Yourself

• Your spouse or business partner

• A trusted advisor

The goal is simple: get clarity on what you actually want out of investing. Because once opportunities start coming your way, it becomes much easier to evaluate them when you already know what you're looking for.

Think of it as creating your investment compass. Without it, every opportunity can start to look appealing. With it, you can quickly determine whether something truly fits your strategy.

Here are a few questions I encourage investors to talk through during that huddle:

Investor Happy Hour Checklist

• Why am I investing in real estate? (cash flow, long-term wealth, diversification, tax advantages, etc.)

• What is my minimum acceptable return for an investment?• What type of investments am I most comfortable with? (multifamily, development, value-add, stabilized assets, etc.)

• What level of risk am I comfortable taking?

• What timeline works best for my goals? (short-term vs long-term holds)

• What qualities do I want in an operator or investment sponsor?

• How important is communication and transparency from the investment team?

• How much capital am I comfortable allocating toward real estate investments each year?

• Do I prefer a smaller number of concentrated investments or spreading capital across multiple deals?

Getting clarity on these questions before reviewing opportunities makes the entire investment process much more intentional. It also helps investors avoid the common trap of chasing deals that look exciting but don’t actually align with their long-term goals.

If you’d like a simple one-page version of this Investor Happy Hour Checklist to walk through with your spouse or partner, feel free to send me a message. I'm also happy to a part of that Happy Hour virtually to walk you through it!

Happy to share it with anyone exploring real estate investing.

Let's Have A Day!!! #DANZA

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