Lesson 08 · 11 min read
Your First Steps in Commercial Real Estate
A concrete 90-day action plan to go from zero to your first commercial real estate deal — what to learn, who to talk to, and what to do in what order.
You've now got the big-picture map of commercial real estate: what it is, what the asset classes are, how investors make money, how it compares to other investments, and whether it fits your life. The rest of this academy will take each of those topics much deeper.
But before you go further, it's worth pausing to answer the question every new CRE investor asks: where do I actually start?
Here's a realistic 90-day action plan you can start on the day you finish this course.
Days 1–30: Learn and observe
Finish the Foundations tier of this academy
Start with Course 2 (Terminology & Key Metrics) — it's the vocabulary you'll need to speak to any broker, lender, or investor without sounding like a beginner. Then move through Courses 3–5 to learn the financial analysis that underpins every deal.
You don't need to finish the entire 20-course curriculum before doing your first deal, but you should absolutely finish the first six courses. Most investors who skip the Foundations tier end up paying for the lesson a lot more expensively on their first deal.
Follow the market
Pick a specific submarket — the area where you live, or the area where you eventually want to invest — and start paying attention to it every day. The fastest way: set up Crexi, LoopNet, and CoStar alerts for your target asset class in your target submarket. Every new listing should land in your inbox.
Read each listing's OM (offering memorandum) as if you were going to buy it. What's the cap rate? Does it look right for the market? What's the lease term? Who's the tenant? Over 30 days you'll develop a sixth sense for what "cheap" and "expensive" look like in your chosen niche.
Read the trades
Subscribe (many are free):
- GlobeSt.com — national CRE news
- Commercial Observer — institutional focus
- Bisnow — regional events and news
- Crexi and LoopNet market reports — data
You're not trying to memorize anything. You're trying to make the industry feel familiar.
Drive your market
Literally get in the car and drive the submarket you're targeting. Look at every commercial property. Note which ones look well-kept, which ones look tired, which ones have tenant signage changes. You'll learn more in a weekend of driving than in a month of listings.
Days 31–60: Build your team
Find a buyer's broker
The single most important person in your first deal. Look for:
- 5+ years in your asset class and submarket
- A track record of closed buyer-side deals (not just listings)
- Willingness to educate, not just pitch
- Responsive (replies the same day)
Interview 3–5 brokers. Ask them what they're seeing in the market, what deals they'd buy with their own money, and what deals they'd avoid. The best broker for you is the one who educates rather than sells — and who has skin in the game (they invest in the asset class too).
Ryan Solberg at MaxLife Development is exactly this kind of broker in Central Florida. If you're outside that market, look for his equivalent.
Line up a lender (or a loan broker)
Talk to 2–3 commercial lenders before you need one. Ask what deals they're doing, what their minimum loan size is, what their current rates look like, and what DSCR they require. Building a relationship before you need the loan gets you much better terms when you do.
Also consider talking to a loan broker — especially on your first deal, their ability to shop multiple lenders saves you time and often gets better terms than you'd find yourself.
Hire a CPA who knows real estate
Not any CPA. A CPA who specializes in real estate. They should already know what cost segregation is, how 1031 exchanges work, and what real estate professional status means. Most generalist CPAs don't, and the mistakes compound.
Interview a real estate attorney
Same deal: find a CRE specialist. You don't need to retain them yet, but you want to know who you'll call when you sign an LOI. Ask about their experience in your asset class and their typical fees.
Open an LLC
Work with your attorney and CPA to set up a single-member LLC (or partnership LLC if you have partners) for your first deal. You can do this before you have a specific deal — the paperwork is simple and the LLC provides liability protection from day one.
Days 61–90: Underwrite, offer, execute
Start underwriting listings
Take 10 listings from your target market and run each through a full pro forma using the techniques from Courses 2, 4, and 5. Don't just eyeball the cap rate — actually model the 10-year cash flow, the debt service, and the returns.
Most listings will fail your underwriting. That's normal. Your job is to find the one in twenty that actually works.
Submit LOIs on deals that pencil
When a deal actually works after your underwriting, submit a letter of intent through your buyer's broker. Expect most LOIs to fail — sellers often have higher price expectations than the numbers support. Your first few LOIs are essentially free practice at negotiating, and you'll get better each time.
Rule of thumb: You'll usually submit 10–20 LOIs to get one accepted.
Run due diligence hard
When you get an accepted LOI, the due diligence period begins. Use the checklist from Course 10 and run every item to the ground. This is the single highest-leverage 60 days in your entire CRE career — do it right.
Most first deals either die in due diligence (good outcome — you avoided a bad deal) or close after renegotiation (good outcome — you used DD findings to lower the price). Either way, you win.
Close the deal
If due diligence passes, you close. Your attorney and title company handle most of the mechanics. You wire the down payment, sign a stack of documents, and walk out owning a commercial property.
Congratulations — you're now a commercial real estate investor.
What happens next
The first deal is the hardest. The second deal is dramatically easier because:
- Your broker relationships are established
- Your lender already underwrote you once
- Your CPA and attorney know your structure
- You have a deal you can leverage (literally) into the next one
- Your confidence is through the roof
Most serious CRE investors go from their first deal to their fifth deal within 3–5 years, then to their twentieth within a decade. The hardest part is getting to deal one.
What to take away
- Your first 30 days should be learning, observing, and building market fluency.
- Your next 30 days should be building your team: broker, lender, CPA, attorney.
- Your final 30 days should be actively underwriting and submitting LOIs.
- Expect to submit 10–20 LOIs for one accepted offer. This is normal.
- Your first deal is the hardest. Everything gets easier from there.
You've finished Course 1. In Course 2 you'll learn the exact metrics and formulas every broker and lender speaks — so when you pick up the phone, you'll sound like someone who knows what they're doing.
Ready? Continue to Course 2: CRE Terminology & Key Metrics →