As May arrives, a curious migration begins on Wall Street.
Traders and fund managers exchange their Bloomberg terminals for beach chairs, fleeing to summer havens in the Hamptons and Martha's Vineyard. This annual exodus is so predictable it has its own investing maxim: “Sell in May and go away.”
But what's often most fascinating isn't just that these professionals take extended vacations from managing other people's money – it's where they're going.
Many rent luxurious summer homes for tens of thousands of dollars, unwittingly becoming part of someone else's wealth-building machine that never takes a summer break.
While Wall Street's finest are “away,” the owners of those summer properties continue collecting substantial rental income, building equity, and enjoying appreciation – all without daily market monitoring or seasonal timing strategies.
This paradox perfectly illustrates the fundamental difference between trading and true wealth building.
The Seasonal Trading Trap
When Wall Street creates patterns like “sell in May,” it introduces unnecessary complexity into investing that primarily serves the financial industry, not individual investors.
And worse, when a large group of traders follow this same pattern, it creates a cascade of problems for average investors actively managing their portfolios:
Increased volatility during summer months
Complex tax implications from moving in and out of positions
Higher transaction costs from unnecessary buying and selling
The stress and cost of trying to time artificial market movements
Market distortions that are disconnected from business fundamentals
Even if you think you're avoiding this by investing “passively” through index funds, your portfolio value still fluctuates based on these artificial patterns. The underlying stocks in your funds are still subject to the volatility created by active traders following these calendar-based strategies.
Does this really sound like a solid foundation for your wealth-building strategy?
The Real Estate Advantage
Now contrast this with rental real estate, especially the kind of commercial real estate we focus on in our syndications.
While residential housing markets might have some seasonal patterns in buying activity, the income stream from rental real estate marches on with remarkable consistency for a very obvious reason: people need a place to live and work year-round.
That continuous cash flow doesn't take summer vacations. Tenants don't get to skip rent payments because it's beach season.
This creates a compounding effect that's nearly impossible to match when you’re trying to time the market. With each passing month (including those summer months) your wealth continues building:
Tenants pay rent
Loans get paid down
Tax advantages accumulate
Property values typically appreciate
The difference is stark: artificial, seasonal trading patterns on Wall Street introduce volatility and inefficiency, while real estate investing offers consistency and compounding growth regardless of the time of year.
The Alignment Advantage
There's another aspect here that doesn't get enough attention: alignment of interests.
Wall Street professionals collect substantial fees to manage money while effectively checking out for the summer. They're still collecting those management fees whether they're analyzing market trends or sipping cocktails on the beach.
This contrasts sharply with real estate operators who remain invested year-round. Property management doesn't pause for summer vacation. When you passively invest in well-structured real estate deals, the operators' success is directly tied to yours – they can't check out for months without consequences to their own returns.
Business Ownership vs. Market Timing
Remember this important distinction: when you invest in rental real estate, whether it's a single-family rental or a multi-million dollar syndication, you're investing in a business.
You're not trying to time markets or trade assets. You're acquiring an income-producing asset with intrinsic value that generates returns regardless of seasonal patterns.
This consistent wealth-building approach has significant advantages over market timing tactics that leave you vulnerable to the whims of Wall Street traders.
So as we head into another season of “sell in May and go away,” ask yourself: are you tired of the Wall Street shenanigans? Do you prefer a wealth-building approach that doesn't take summers off?
Rental real estate provides a wealth-building approach that works consistently throughout the year – regardless of whether Wall Street is paying attention or not.