The Roofing Pro's Guide to Investment Diversification: Protect Your Commission Checks and Build Wealth
Oct 20, 2025
Did you know that a majority of Americans who suffer major investment losses have most of their money in just one or two types of assets?
As someone who works with roofing sales reps and business owners, I see this pattern all the time—especially among high earners who've put everything into their business or a single hot stock tip from a supplier.
I've spent years helping roofing professionals avoid this common pitfall, and there's one strategy that stands above the rest: diversification.
Seriously, I'm always shocked to see how much money some roofing pros have riding on one single investment. Maybe it's all tied up in their roofing company, or they dumped a huge commission check into cryptocurrency, or they're banking everything on rental properties because "real estate always goes up."
To me, it's like working on a steep pitch without fall protection—one bad quarter, news article, or market swing can cause the value of your investment to plummet.
Think of it as not putting all your eggs in one basket, but there's so much more to it than that!
Whether you're a roofing sales rep banking big commission checks or a roofing business owner reinvesting profits, understanding diversification could be the difference between reaching your financial goals and watching your savings disappear overnight.
Understanding Portfolio Diversification Basics for Roofing Professionals
Diversification in its most basic sense is about spreading your risk across a variety of investments to get the most efficient return on your money.
There's a relationship between risk and return when it comes to investing, but it's not always an even relationship across all asset classes.
For instance, some roofing pros might flock to bonds because they've heard they're the safer asset, until rising interest rates cause their value to decline. Other folks are terrified of stocks because of the potential to lose their entire value if a company goes under, yet stocks have the highest long-term growth rate of all asset classes.
That's why it's so important to learn the fundamental principles of asset allocation. Asset allocation, which is one form of diversification, is about finding the right mix of different asset classes that will give you the most efficient return for your financial goals.
An asset class is a grouping of investments that share similar characteristics. Most people are familiar with the major ones like stocks, bonds, real estate, commodities, currencies, and cash.
Each asset class shares common traits such as risk profile, return characteristics, and how they're valued.
Why Diversification Matters More for Commission-Based Earners
If you're earning commission in roofing sales, your income already fluctuates with the seasons, weather patterns, and economic conditions. Storm season might bring a windfall, while slow months can be lean.
The last thing you need is your investment portfolio riding the same rollercoaster. When roofing work slows down AND your investments tank at the same time, you're in serious trouble.
That's why roofing professionals need diversification even more than traditional W-2 employees with steady paychecks.
Types of Investment Diversification for Roofing Business Owners
Now that we have a high-level understanding of asset allocation, let's break it down one step further with asset class diversification.
For instance, stocks can be further broken down into several asset classes like large-cap value, large-cap growth, small-cap value, small-cap growth, foreign markets, and emerging markets, to name a few.
You can break down any of the major broad asset classes into their subgroups. This is important to know because if your portfolio is 100% stock, it can still look completely different from someone else's portfolio who is also 100% stock, depending on the asset classes being invested in.
Is it all U.S. stock, or are there foreign markets? Is it all large blue-chip companies, or is it more up-and-coming growth-oriented companies?
You can even explore geographical diversification opportunities like stocks in European, Asian, or South American markets to get more broad exposure.
Sector and industry diversification can also be used as a means to round out your portfolio. For example, in addition to my major broad index funds, I also include some exposure to a real estate fund to get added diversification.
You can explore funds or stocks that are within other major industries like energy, healthcare, information technology, or communications, to name a few. See how these can complement the other traditional holdings in your investment lineup.
Special Considerations for Roofing Company Owners
If you own a roofing business, you likely already have significant wealth tied up in your company, equipment, trucks, and inventory. That's not liquid, and it's 100% dependent on one industry.
This makes outside investment diversification absolutely critical. You need investments that aren't tied to the construction industry's boom-and-bust cycles.
Building a Diversified Portfolio from Scratch: A Strategy for Roofing Sales Reps
Start with core investment holdings like an S&P 500 index fund or a total stock market fund. This will get you exposure to hundreds or even thousands of companies right off the jump.
If you're just getting started, you can stay right here as you build up the habit of contributing on a regular basis and watching it grow. No need to rush the process.
For roofing sales reps: Set up automatic transfers from your checking account to your investment account on the 1st and 15th of each month. This ensures you're investing consistently, not just when you land a big job.
Add complementary assets strategically, such as large-cap value, large-cap growth, international stock, and short/mid-term bonds. As mentioned earlier, you can even add specific industries or sector funds like biotech, healthcare, or real estate.
Implement dollar-cost averaging so you're buying on a consistent schedule. This will allow you to stop focusing on what the market is doing day to day. Sometimes prices will be lower when you buy, sometimes higher, and it will average out over the long run.
Balance your risk tolerance with growth potential. If 80% of your capital is riding on cryptocurrency, then brace for turbulence in your account. It's about finding a mix of assets that will provide a solid trend in growth and how much you're comfortable seeing your account fluctuate on the downside while still staying on the plan.
Managing Irregular Income: Investment Tips for Commission-Based Roofing Sales
When you close a $50,000 job and pocket a $5,000 commission, it's tempting to celebrate or immediately invest it all in one place. Here's a better approach:
- Pay yourself first: Set aside your emergency fund contribution (3-6 months of expenses)
- Invest systematically: Put 20-30% into your diversified portfolio using dollar-cost averaging
- Reinvest in business: Allocate funds for tools, training, or marketing
- Save for taxes: Remember, commission income means quarterly estimated taxes
This approach ensures you're building wealth across multiple areas without overexposing yourself to any single risk.
Common Diversification Mistakes Roofing Professionals Make
Believe it or not, you can actually overdo it when it comes to diversification. Identify false diversification traps like holding too many funds.
If you've got 50 funds in your portfolio, then that's not the best use of your money. One, you're going to have to be buying shares in each of those funds. Two, there's going to be overlap of the same companies held in each of those funds.
Avoid timing market mistakes. Too often, people try to capitalize on market downturns. Guess what—it can always go lower. That's what you call "trying to catch a falling knife."
Following idioms blindly like "buy low and sell high" isn't always the rule. Be mindful of the market as it affects your portfolio and be responsive rather than reactive in your decision-making.
The "All-In on Real Estate" Trap
I see this constantly with roofing business owners. You made money in roofing, so you buy rental properties—makes sense, right? You understand property and construction.
But now you've got your business income AND your investment income both tied to real estate markets. If the housing market crashes, both your roofing business and rental income suffer simultaneously.
True diversification means investing outside your area of expertise sometimes.
Maintaining Your Diversified Portfolio While Running a Roofing Business
There's a phrase I picked up a long time ago: "Investments work, investors don't."
Finance is 80% behavior management, in my opinion. Managing the human element of the investment portfolio is going to make or break your overall success.
Set regular review schedules to check on performance and make adjustments as necessary. I keep my reviews at a monthly cadence, typically falling on the last day of the month. You can stretch it out longer if you want, although I wouldn't take it further than three months.
For busy roofing professionals: Schedule your portfolio review on the same day you review your business financials. Many roofing company owners do this on the last Sunday of each month.
On the flip side, you can check it more frequently, like once a week if you wish. In the beginning of your money management and investing journey, this can be especially helpful.
Be careful, though, because this can lead to anxiousness and hyperfocus on those little market changes that happen from daily or week-to-week fluctuations.
Implement rebalancing strategies to keep your portfolio in the original proportions you set when you first developed your plan. Just like a roof system, some components will perform differently than others as time goes on.
By selling the higher-performing investments, you can then use those proceeds to buy more of the other investments and keep a good mix.
Adjust for life changes and goals. You're not the same person physically, mentally, or emotionally as you were 15 years ago. Same goes for your portfolio.
As you progress in life, you're going to need to make shifts from more growth-oriented investments to more conservative options to preserve what you've built. It's like you've been building a strong roof system, and now you're going to be maintaining it for the long haul.
Monitor market conditions and trends so you can learn what factors impact them.
Diversification Strategies for Different Career Stages in Roofing
Let's walk through an example of how to adjust diversification strategies throughout different career stages in the roofing industry.
Early Career: The New Roofing Sales Rep (Ages 25-35)
Meet Marcus, a roofing sales rep in his early 30s who just finished his first successful storm season, making great commissions and wanting to make the most out of what he earns to prepare for the future.
Since he's got a pretty good amount of time before retirement, he's going to invest 100% of his money in stocks. He knows that sometimes the market will go up and sometimes it will go down, and overall, he's looking for long-term growth.
He doesn't know much at first, so he begins with just an S&P 500 index fund. Over the years, he starts adding different funds. Most follow major asset classes like large-cap value and large-cap growth that make up 75% of his holdings, and he also has some funds that cater to foreign markets and real estate.
Marcus sets up automatic investments of $500 per month during slow season and increases it to $1,500 per month during storm season when commissions are rolling in.
Mid-Career: The Established Roofing Professional (Ages 35-50)
Fast forward about 15 years, and our friend Marcus is crushing it in his roofing career. He's either running his own crew or has moved into roofing business ownership, calling shots and living a great life while still staying dedicated to his investment strategy—although now it looks a bit different.
He's made strides in building his account and is adapting his strategies for mid-career growth. Since he's got the majority of his money in core index funds, he's now gotten into individual stocks and sectors to round things out based on his interests.
He does a good job of not overdoing it, though, by keeping individual stocks to no more than 5% of his overall portfolio and making sure that the total amount of individual stocks do not exceed 20% of his account balance.
Pre-Retirement: The Veteran Roofing Business Owner (Ages 50-65)
In his mid-fifties, Marcus is starting to make plans for pre-retirement adjustments and shift from a growth-oriented approach to one that focuses on preservation. He's adding short and mid-term bond funds.
There are still a few stocks in there that he wants to keep, but he's scaling back his overall mix to make room for the bonds. He wants to preserve as much of his account value as possible because now he's getting excited about what his lifestyle will look like during retirement.
Many roofing business owners at this stage are also planning their exit strategy—will they sell the business, pass it to family, or hire a manager? This business transition planning should align with your investment diversification strategy.
Retirement: The Retired Roofing Professional (Ages 65+)
Now, after 30 years of a wonderful career in the roofing industry, the time has finally come to get his gold watch and say goodbye to the daily grind for good.
Marcus recognizes that he still needs to maintain diversity during retirement now more than ever. He's got a core portion of his portfolio in conservative holdings like U.S. treasuries and short-term bonds to keep up with inflation.
He still keeps some stock, but it's primarily stable, dividend-producing, blue-chip companies. There's a good portion that sits in cash that is readily available for him to draw on a regular schedule, live off of, and live the good life for the remainder of his years.
Tax Implications of Diversification for Roofing Professionals
Understand tax-efficient investing like taking advantage of retirement accounts to boost your growth potential. These accounts allow your earnings to grow tax-deferred and can be taken out tax-free when you hit retirement age.
For self-employed roofing contractors: Look into SEP IRAs or Solo 401(k)s, which allow you to contribute significantly more than traditional IRAs—up to $69,000 in 2024. This is a game-changer for high-earning roofing professionals.
If you're invested in a non-tax-advantaged account, like a brokerage account, then plan for capital gains implications when making decisions to sell. Long-term capital gains rates can save you a ton of money depending on how long you held the investment for.
Explore other tax-advantaged accounts such as health savings accounts and 529s. They offer similar benefits to retirement accounts when used for their specified purpose.
Roofing business owner tip: If you have employees, offering a SIMPLE IRA or 401(k) plan can help attract and retain quality workers while providing tax benefits for your business.
Measuring Diversification Success in Your Roofing Business Wealth Strategy
Track portfolio performance to gauge whether you're on track or not. Compare your portfolio's performance against relevant benchmarks to see how you stack up to the rest of the market.
Investors often use the S&P 500 index as a performance benchmark because it contains 500 of the largest U.S. publicly traded companies. The Dow Jones Industrial Average and Russell 2000 are also common benchmarks that are widely referenced.
Monitor diversification effectiveness. If you're not seeing returns based on your expectations, then adjust little by little. Make sure to give it time—like half a year—before making any major changes.
Key metrics for roofing professionals to track:
- Total portfolio value growth year-over-year
- Portfolio performance vs. S&P 500 benchmark
- Income stability (investment income + business income)
- Risk exposure to construction/real estate sector
- Emergency fund adequacy (especially important for seasonal income)
Take Action: Start Diversifying Your Roofing Income Today
Remember, diversification isn't just a one-time decision—it's an ongoing strategy that evolves with your financial journey.
I've tried many different approaches, including holding individual stocks, and I can say with confidence that asset allocation is a much more efficient use of my time and money.
By implementing the principles we've discussed, you're taking a crucial step toward building a more resilient investment portfolio that can weather both market downturns and slow seasons in the roofing industry.
Start small, stay consistent, and regularly review your diversification strategy. Ready to take action?
Your Next Steps:
- Calculate your current net worth (including business value, if applicable)
- Assess how much of your wealth is tied to the roofing/construction industry
- Open a retirement account if you haven't already (SEP IRA, Solo 401(k), or traditional IRA)
- Start with a simple S&P 500 index fund and automate monthly contributions
- Schedule quarterly portfolio reviews on your calendar
- Gradually add complementary asset classes as your account grows
Begin by assessing your current investments and identifying areas where you can introduce more diversity. Your future self will thank you for making this smart investment choice today.
After years of climbing ladders and closing deals in the roofing industry, you deserve a retirement where you're not worried about money. Proper diversification is how you get there.