What We Ask Every Investor Before They Deploy: “What Do You Actually Want Your Money to Do?”
What Do You Actually Want Your Money to Do?
Before you invest a dollar, ask yourself a simple question: What do I actually want this money to do? This may sound obvious, but many investors never truly consider it. They chase hot stock tips, jump into trendy deals, or follow what worked for someone else, without ever defining what success looks like for them. But if you don’t define success on your terms, even a “good” investment can feel like a letdown.
At Ocean Ridge, we’ve seen it firsthand. Investors come to us with portfolios that look great on paper, but don’t align with what they actually want their money to produce: freedom, tax relief, control, or long-term peace of mind. The truth is, returns only matter in the context of your life.
So let’s reverse engineer the question: If your money could work exactly the way you want it to, what would that look like?
Why Starting with the End Goal Changes Everything
You’re a strategic operator in your business. You wouldn’t launch a product without defining what success looks like - so why invest your personal wealth that way?
Most investors assume “more money” is the goal. But what if the real goal is less stress? Or income that pays for your lifestyle? Or knowing your kids are set for life, no matter what happens in the markets?
Without clarity, even the best asset class can feel off. Take the old-school 60/40 portfolio - once the darling of “balanced” investors. In 2022, both stocks and bonds dropped in tandem. Suddenly “diversified” portfolios weren’t so diversified.
You don’t need just a portfolio. You need a plan. And it has to start with your version of the finish line.
The Three Profiles We See Most Often
After working with hundreds of high-net-worth entrepreneurs, we’ve found most investors fall into one of three profiles:
The Cash Flow Seeker: You want passive income now, not ten years from now. You’ve built a business, earned your stripes, and now you want your money to work for you. Maybe that means funding your lifestyle, freeing up time, or stepping back from the day-to-day. The key here isn’t just growth, it’s predictability. You want capital that reliably deposits income into your account every month or quarter, with minimal stress.
The Tax Strategist: You’re laser-focused on what you keep. You’ve likely had a high-income year, a business exit, or a major liquidity event. Now your priority is minimizing what goes to Uncle Sam. For you, tax strategy isn’t a side note - it’s the return driver. You’re hunting for depreciation, deferrals, write-offs, and ways to optimize every dollar you’ve already earned. The game isn’t just ROI. It’s ROT (Return on Taxes Saved).
The Legacy Builder: You’re playing the long game. You’re thinking in decades, not quarters. You want your wealth to endure, compound, and outlast you - not just fund lifestyle now, but secure your family’s future. You’re okay with lower short-term income if it means massive long-term payoff. You think in terms of equity multiples, compounding, and generational resilience.
Why Multifamily Hits All Three
You might be thinking, this sounds great in theory, but what kind of investment can actually deliver on these goals? For many of the ultra-wealthy (and our own investors), the answer has been private real estate, especially multifamily apartment communities. In fact, many family offices and savvy investors treat private real estate as a core holding in their portfolios, not a sideline, because it can produce benefits you simply don’t get from stocks or bonds. Let’s look at how multifamily checks the boxes for each profile:
Cash Flow Seekers: You’ll want stabilized multifamily assets in high-demand markets. These properties produce income immediately, often in the first quarter. Think of them like profitable, boring businesses - they don’t need to hit a home run; they just need to deliver consistent checks.
Tax Strategists: You’ll lean into value-add deals with cost segregation, bonus depreciation, and smart structuring. A well-positioned $100K investment can create $70K+ in first-year paper losses, shielding your income while your equity grows behind the scenes.
Legacy Builders: You’ll prioritize long-term growth over short-term yield. That means assets in emerging markets, development plays, or repositions with 3-10 year equity upside.
It’s no wonder, then, that multifamily real estate has earned a reputation as a “Goldilocks” asset class for building wealth. It produces income and growth, with built-in stability and tax perks. In fact, Ocean Ridge’s entire approach is built around these very benefits – we acquire and operate institutional-quality multifamily assets engineered for cash flow, tax efficiency, and long-term wealth. It’s about getting all the major advantages in one package.
Build Your Wealth Your Way (Conclusion & Next Steps)
The bottom line is this: Investing is personal. The right investment plan for you is the one aligned with what you actually want your money to do. It’s time to break away from one-size-fits-all portfolios and outdated strategies that may have worked in a different era (or for someone with different goals). Instead, start with your why. There’s no wrong answer, except not knowing your answer.
By asking this question up front, you’ll make smarter decisions and feel more in control. You’ll invest with purpose and confidence, rather than accumulating a hodgepodge of assets that keep you up at night. At Ocean Ridge Capital, we’ve seen firsthand how transformative this clarity can be.
Interested in learning more? We love helping fellow entrepreneurs and professionals design investment plans around their unique goals. If you want to see how multifamily investments could be a fit for your objectives, you can download our Passive Wealth Playbook or book a call with me here (via Calendly) and tell us what you actually want your money to do. We’ll share how we can help make it happen. You’ve done the hard part by earning and saving your capital; now it’s time to put that money to work on your terms. Your future self will thank you for it.
