In This Article
Let’s get one thing straight: You don’t need a full “investing dream team” before you make your first investment. But you do need the right people at the right time if you want to protect your investments, build long-term wealth, and avoid the kinds of mistakes that cost you thousands.
However, most investors get this wrong. They either:
Skip building a team, preferring the DIY approach in order to “save” money, or
Wait until they’re knee-deep in a deal before scrambling for help.
That’s when things go sideways.
Like the time I hired a local tax pro who “knew real estate.” They took depreciation not just on my rentals, but on my primary residence too. That error, caught years later, cost me thousands and forced me to amend several tax returns—all because I didn’t have the right expert on my side from the start.
Bottom line? Your team isn’t a luxury. It’s leverage.
Done right, your investing dream team protects you, unlocks new opportunities, and accelerates wealth-building with way less stress. And you don’t need to spend big bucks upfront.
I’ll walk you through who should be on your team, when to bring them in (no, you don’t need everyone now), and how to find the right fit—without wasting time or money.
The Cost of Going Solo Is Higher Than You Think
Here’s what happens when you try to DIY your investing strategy for too long:
Investor A: Knows they want to invest passively, but keeps pushing off “building a team.” They ask friends for tips, Google (or nowadays, ask AI) investment terms, and copy what others are doing. Eventually, they invest—but miss key tax advantages, skip legal reviews, and second-guess everything because they’re flying blind.
Investor B: Starts small but smart. Sets clear financial goals—on their own or with a fee-fiduciary advisor. Loops in a real-estate-focused CPA at the beginning of the tax year to strategize the next 12 to 24 months. Uses vetted referrals to hire a legal expert who flags hidden capital call clauses in a deal. Everything is intentional, not reactive.
The difference?
Investor A is overwhelmed and exposed.
Investor B is confident and compounding.
And here’s the truth: Building your team is an investment strategy in itself. The key is to start lean, scale smartly, and level up team members as you grow.
How to Build Your Investing Team the Smart Way
Step 1: Know your core four
These are the four foundational roles every serious investor needs as they grow.
1. Financial expert:
Helps define your goals, timeline, and risk tolerance
Keeps your investment strategy aligned, so you’re not constantly chasing the next shiny deal
Red flag: If your financial advisor doesn’t understand real estate or private placements, they’re not the right fit.
2. Tax strategist:
Minimizes tax liability, sets up smart structures, and correctly files all tax forms (I’m looking at you, Schedule E and Schedule C) and K-1s if you are a passive investor.
Understands depreciation, cost segregation, and 1031 exchanges, and isn’t afraid to leverage them
Red flag: If your tax strategist doesn’t know how passive losses work, tell you it’s risky to take depreciation, or don’t suggest a cost segregation study, it’s time to upgrade.
3. Legal expert:
Reviews deal documents and structuring, protects your assets, and guides titling decisions.
Make sure what you think you own is legally protected from predators and creditors.
Red flag: If they avoid reviewing your transaction documents (including your PPM) or avoid securities law, they may lack experience with real estate and/or syndications.
4. Retirement account specialist:
Keeps your SDIRA or solo 401(k) compliant and tax-efficient
Handles necessary filings and helps you avoid UDFI/UBIT pitfalls
Red flag: If they can’t clearly explain prohibited transactions, move on.
Step 2: Build as you scale (not all at once)
Here’s what smart, staged growth actually looks like:
Planning phase: Set the foundation: Even if you haven’t made your first investment yet, this is where to begin.
Become your own financial expert or hire a coach, mentor, or fee-only fiduciary who understands the type of real estate you want to invest in.
Hire a tax pro early to avoid rookie mistakes and uncover hidden opportunities.
Define your goals, identify available capital, and create your investing game plan.
Revisit your financial plan and tax strategy at least annually.
Deal funnel phase: Evaluate opportunities: You’re actively exploring operators, markets, and deals.
Keep working with your financial and tax experts to stay aligned.
Start researching legal counsel and retirement account custodians now—don’t wait until wire instructions hit your inbox.
Begin assembling the next layer of your team before you’re under pressure.
Investing phase: Deploy capital with confidence: Now it really matters. Mistakes at this stage get expensive.
Hire a legal expert to review deal documents and ensure your investment is properly titled and protected, as well as help you avoid legal traps and capital call clauses that can erode your equity or surprise you later.
Hire a retirement account custodian if using SDIRA or solo 401(k) funds, to ensure proper account setup, tax compliance, and avoid disqualified transactions that could trigger IRS penalties.
Scaling phase: Optimize and streamline: Your portfolio is growing, and complexity starts to increase.
Add a whole life insurance specialist to create velocity and optimize capital deployment.
Bring in a bookkeeper and admin support to streamline operations, manage cash flow, and free up your time.
Protect your wealth, automate day-to-day duties, and build systems that scale with you.
Step 3: Watch for these common mistakes
Even experienced investors fall into these traps:
Waiting too long: Don’t try to hire a tax strategist in March or a lawyer the night before signing.
Using the operator’s referrals blindly: Ask if they’re being compensated. Always vet independently.
Sticking with the wrong person too long: You’ll outgrow some team members. That’s normal.
Trying to build the perfect team upfront: Prioritize what you need now. Progress beats perfection.
Step 4: Vet like a pro
When you are vetting a potential investing dream team member, don’t overthink it—just be intentional. Here’s your checklist:
Ask for real estate-specific experience.
Confirm credentials (especially for legal/tax pros).
Interview at least two providers per role.
Get referrals from trusted investors.
Gut check it: Do they communicate clearly? Listen well? Respect your vision?
Pro tip 1: Ask the same questions in the same order, and take notes so you can compare the conversations after the call.
Pro tip 2: Keep in mind that you’ll likely evolve your team over time as you grow and things get more complex. So build for your next stage of investing, not forever.
You might also like
Wrapping Up: Don’t Build Wealth Alone
You’ve worked hard to earn your capital. Don’t let guesswork or a weak support system stall your momentum.
Whether you’re prepping for your first deal or managing a growing portfolio, here’s the truth: Your investment success is only as strong as the team behind you.
Start lean. Stay strategic. Upgrade as you grow. And whatever you do, don’t wait until you’re under contract—or racing toward a tax deadline—to bring in help. That’s when mistakes get expensive.
Let’s make sure your next move is supported by the right people. DM me here on BiggerPockets if you want to talk about what that could look like for you.
Protect your wealth legacy with an ironclad generational wealth plan
Taxes, insurance, interest, fees, bills…how can you acquire wealth, let alone pass it down, when there are major pitfalls at every turn? In Money for Tomorrow, Whitney will help you build an ironclad wealth plan so you can safeguard your hard-earned wealth and pass it on for generations to come.
