Trying to do it all yourself is common. We think we know what we’re doing until a lightbulb moment comes—usually after we’ve already messed up. That’s why building a team of financial experts matters. Having people who can steer you away from costly mistakes is key to protecting and growing your investments and assets.
Experts with focused knowledge are invaluable. Below I’ll describe what our ideal team looks like, and I’d love to hear who you rely on for your own dream team.
The idea for this came from Garrett Gunderson’s provocative book, Killing Sacred Cows: Overcoming the Financial Myths That Are Destroying Your Prosperity. I don’t agree with everything in it—he’s pretty anti-401(k), pushes real estate hard, favors whole life insurance over term, and even suggests keeping cash at home for emergencies—but the book did push us into real estate. I paused 401(k) contributions for two years to save for rental down payments. Those two years out of the market paid off: the housing market did just as well for us as the stock market might have.
Gunderson is clearly selling a coaching business, but his main point about building a strong team of experts stuck with me. That’s what I want to focus on.
A few roles you’ll want on your team:
– Accountant: The tax code is complicated. TurboTax is fine for basic returns, but it won’t spot many credits or help you plan complex tax strategies. For example, TurboTax missed a $1,000 ADA credit for my wife’s adjustable chiropractic table; our accountant caught it a year later and applied for the credit retroactively. Once we had rental properties, DIY tax software wasn’t going to help with decisions like choosing between standard or accelerated depreciation. A good accountant helps prepare returns and minimizes your tax bill. Meet with them at the start of the year to plan. We pay roughly $1,000 a year for accounting and consider it money well spent to avoid higher taxes. A solid accountant is the cornerstone of your team.
– Real estate agent: We found our accountant through our investment property agent—he uses the same accountant for his complex business taxes. Build your team through referrals: ask people “Who do you use?” A good agent for rentals should be a businessperson first. Ours never pressures us to buy; he’s often more skeptical than I am. If an agent starts pushing a property, walk away.
– Mortgage broker: For financing, work with someone reliable. I had success with a national bank loan officer—hardworking, reliable, and helpful in getting underwriters what they needed so closings went smoothly.
– Home inspector: Great inspectors are worth their weight in gold. They find the problems you don’t want to discover after closing—the foundation issues, dead critters in the furnace, and other deal-killers. You’ll be grateful they brought bad news.
– Insurance broker: Insurance for rentals and other businesses can get expensive. We carry homeowners insurance on six properties, umbrella coverage, and auto; we’ll eventually add life and disability. A good broker shops the market for better rates and can bundle policies for discounts. But do your homework: some brokers push extra coverage just to earn big commissions. Make sure you understand how much coverage you actually need.
– Estate planning attorney: No one likes thinking about death, but planning for your survivors is essential. Don’t leave things to chance or probate. A good estate lawyer will guide you through wills, living wills, durable powers of attorney, and trusts without making it scary. For us, two meetings were enough: one to explain our wishes and one to review the documents. We paid about $500 for our living will and powers of attorney—well worth it to avoid a probate mess later. You can add or update a revocable trust later if you want to control how inheritances are distributed over time.
Mentors and advisors
Mentors come in many forms—anyone you trust to give honest, experienced advice. If you’re paying someone, they’re an advisor; unpaid mentors are people you can lean on for real-world guidance. My colleague who got me into real estate is an excellent mentor: he knows investing and home construction, which is incredibly helpful.
Sometimes finding time for one-on-one mentoring is hard. I use a “ghost mentor” approach: I learn from the online personal finance community, books, and occasional questions to my team. Books like Tony Robbins’ Unshakeable can feel like a mentor in print. I also try to meet other bloggers and investors locally—those informal relationships are mentoring too.
You’re the quarterback
Even with a strong team, you’re still the one making the big decisions. You’re the CEO of your financial life. Keep your health and relationships in order—your family and close friends are the most important team members. My wife, Mrs. Cubert, has been the driving force behind much of what I’ve accomplished. Big goals mean nothing without family support.
Final thought
You’re only as good as the people around you. Build your team of experts, treat them with respect and loyalty, and don’t forget to care for your family team as well.