Reader,

Katie and I are writing to you from Tempe, Arizona, sitting halfway through a trip with our respective parents, Olavo, Teresa, Lesley, and Randy.

The purpose of this trip is twofold. On a personal level, we absolutely love this part of the world and can see ourselves spending more and more time here creating memories as our child grows. But just as importantly, we wanted to share this experience with our parents. Please note, no golf has been played on this trip, although we are planning on going to TopGolf tomorrow night. They sacrificed a lot to provide for us growing up, and being in a position to bring them along to share new experiences is a massive "why" behind the wealth-building journey. When you stop trading 100% of your time for clinical dollars, you finally get to buy back your time for moments exactly like this.

On a professional level, this trip is also a scouting mission. As a real estate investor, my entire portfolio has been strictly confined to the Greater Toronto Area (GTA). However, owning a vacation rental in a warm climate with access to year-round golf has been sitting on my vision board for years. There are three things yet to accomplish before Apri 23, 2027. For those who don't know, I created this board after much hesitation on Jan 1 2024. The goal was to achieve these milestones and steps before my 40th birthday.

Between family dinners and desert sunsets, we have been touring homes and driving through neighbourhoods to finally get the lay of the land.

The Cross Border ROI Checklist

I don't just want to tell you about my vision board; I want to show you exactly how I analyze these properties. When evaluating a US-based short-term rental (STR) from across the border, you have to remove the emotion and look strictly at the math.

Here are the exact three metrics I am actively evaluating on this trip:

1. Target Cash-on-Cash (CoC) Return: I am looking for a minimum CoC return of 8% to 12%. This metric tells me exactly how much cash flow my initial down payment and closing costs are yielding in year one. If it doesn't beat what I can make passively in a broad-market ETF, it's not worth the operational headache.

2. HOA Short-Term Rental Restrictions: You can find a beautiful property with great numbers, but if the Homeowners Association (HOA) prohibits rentals under 30 days, your Airbnb strategy is instantly dead. Verifying the specific HOA bylaws and local municipal zoning laws is step one before making any offer.

3. Local Property Management Fees: Because I live in Canada, self-managing an Arizona property isn't realistic. I am strictly budgeting 20% to 25% of gross revenue for a premium, full-service local property management team. If the property doesn't cash flow after paying a manager, it is a job, not an investment.

Buying the Dip at 30,000 Feet

While I was looking for real estate deals on the ground, the stock market was offering its own discounts. If you have been watching the news, you know it has been a wild week. Between recent elections and shifting economic data, uncertainty is running hot.

I had several of you message me asking if the Nasdaq really dropped 5% in one day. You were spot on: the Nasdaq Composite plunged 5.52% in a massive single-day decline, while the VIX (the market's official "fear index") surged nearly 70%.

When the fear index spikes, the average investor panics. But for long-term, focused investors, these moments of extreme fear provide incredible opportunities to gain exposure to great assets at a discount. In fact, while we were flying down to Arizona, I was on the airplane Wi-Fi placing limit orders for my portfolio. I keep things incredibly simple, holding only two assets in my TFSA: one broad ETF and one individual stock. If you want to see exactly what I am buying during these market dips, you can check out my portfolio using my Blossom link here.

The "Buy the Dip" Safety Net Rule: When the market drops, it is tempting to throw every dollar you have into investments. But as a clinician, you cannot afford to jeopardize your foundation. If you are going to buy the dip, you must follow this simple rule: Only deploy excess capital sitting outside your 3-6 month clinical buffer. Never gamble your emergency reserves just because stocks are on sale.

Shoutout: Cumberland Wellness is investing in its team 🌿

Later this month, I’m running a private session for the team at Cumberland Wellness called Money Matters for Massage Therapists.

We’ll cover:

• Taxes and types of income: how taxes work if you’re an employee, a sole proprietor or a professional corporation, what to do about a bigger tax bill than you expected, and a simple way to set money aside so tax season doesn’t sneak up on you.
• Debts, assets and financial freedom: what to pay off first when you’re juggling a mortgage, a tax bill and a line of credit, and whether to build savings while you still carry debt.
• Budgeting for busy practitioners: a simple system for irregular income, plus a quick net worth statement so you know exactly where you stand.

We’ll finish with open Q&A, including how to find and work with a financial advisor.

What I love about this: most clinics invest in their team’s clinical skills through courses, certifications and in-services. Very few invest in their team’s financial confidence, even though that affects stress, retention and how present practitioners can be with their patients. Cumberland Village chose to make it part of how they support their people, and I think that’s what great clinic culture looks like.

If you own or manage a clinic and want something similar for your team, just reply to this email. I’d love to put together a session for your group.

Have a lovely rest of your Sunday,

​@financiallyfulfilledpro and Certified Financial Counsellor CFC™

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