Your first deal is the hardest one you’ll ever do. Not because it’s complicated. Because you don’t believe it’s going to happen yet.
So you research. You watch one more video on BRRRR. You compare CRMs for a deal you don’t have. You tell yourself you’re getting ready.
Research feels like progress. It isn’t. The first deal comes from daily activity, not more information. Here’s a ninety-day plan built on that idea. Follow it week by week.
Before you start: the three decisions
Make these decisions on day one and don’t revisit them for ninety days.
- One market. Close to where you live. You’ll drive to properties, meet contractors and sit at closings. Distance makes everything harder.
- One or two lead sources. Driving for dollars, probate, direct mail, cold calls, referrals from people you know. Pick what you can afford in time and money and do it consistently. The off-market lead sources guide compares them.
- One primary exit. Flip, rental, or resell to an investor where your state’s law allows. You can change later. For now, one.
Write those three decisions down. Tape them where you’ll see them.
Week 1: Learn your market cold
Before you talk to a single seller, you need to know what houses in your area are actually worth.
- Pick a handful of neighborhoods in your market.
- Pull recent sold comps for each — sold, not listed. Same school zone, similar size, nearby.
- Drive those neighborhoods. Notice condition, upkeep, vacant houses, and where the clear boundaries are.
- Learn your formula. For flips: ARV × 0.70 − repairs. For rentals: start with the 1% rule as a screen, not a verdict.
- Set up a simple tracker: lead, date, source, conversation notes, next follow-up date.
By the end of week one, you should be able to look at a house in your target area and guess its after-repair value within a reasonable range. Not perfectly. Reasonably.
The comps guide has the rules I use when pulling comps.
Weeks 2–4: Start conversations every day
This is where most people quit before they start. Don’t.
Every working day, you’re generating leads and talking to owners. Not some days. Every day. Even if it’s only an hour.
What a good daily block looks like
- Lead generation. Drive a route, pull a list, send your mail, make your calls.
- Conversations. Call back every response the same day. Speed matters.
- Follow-up. Contact everyone whose follow-up date is today.
- Log it. Every conversation goes in your tracker with a next step.
What to say to sellers
You’re not pitching. You’re diagnosing. Ask about four things, in this order:
- Condition — what does the house need?
- Timeline — when do they need this solved?
- Motivation — why sell, and why now?
- Price — only after the first three.
Then listen. Let silence work. Most of what you need to know comes after the pause.
The motivated seller script guide walks through these conversations in depth.
Week 4 checkpoint: honest review
At the end of week four, sit down with your tracker and ask:
- Am I doing the activity every single working day?
- Am I getting conversations, or just contacts?
- Do I know what houses are worth in my area?
- Have I walked at least a few properties?
If the answer to the first question is no, that’s the whole problem. Fix it before you change anything else. Most people want to switch lead sources at this point. Don’t. A mediocre list worked for ninety days beats a perfect list worked for nine.
Weeks 5–8: Walk properties and analyze everything
Now the conversations should start turning into appointments.
When you walk a property, bring a repair sheet and go system by system: roof, foundation, HVAC, plumbing, electrical, water heater, windows, kitchen, baths, flooring, paint, exterior. Take photos of everything. If you can bring a contractor, do. Their eyes are worth more than your guesses.
Then analyze. Every single lead, even the ones that are obviously not deals. You’re building judgment.
- Estimate the ARV from sold comps.
- Estimate repairs, then add a contingency.
- Pick the exit.
- Run the maximum allowable offer formula for that exit.
Let the paper make the decision. The deal analysis guide lays out the full underwriting sequence.
Weeks 9–12: Make offers — lots of them
You’ve got conversations and you’ve got numbers. Now you make offers.
Most will be rejected. That’s normal. You’re not trying to win every offer. You’re trying to make honest offers based on real numbers, explain how you got there, and follow up.
How to make an offer without insulting anyone
- Walk them through your math in plain English: what it’s worth fixed up, what the repairs look like, what it costs you to buy, hold and sell.
- Explain that your number comes from that math, not from what you hope to pay.
- Tell them it’s okay to say no, and ask if you can check back in.
Then follow up. A seller who says no in week ten may call you in month five. The money is in the follow-up.
Before you sign anything
- Use a real estate attorney for your contract.
- Know your exit before you sign, not after.
- In South Carolina, closings are supervised by an attorney, and the 2024 law changed the rules on marketing property you don’t own. Read the plain-English SC summary first. Outside South Carolina, check your own state’s current rules and talk to a local attorney.
- Get someone experienced to look at your numbers.
Week 12: The first investment property — or the lessons that get you there
Some people have a contract by week twelve. Many don’t. Both are fine if you’ve done the activity.
If you don’t have a deal yet, look at your tracker and find the weakest stage. Not enough leads? Increase volume. Leads but no conversations? Faster callbacks. Conversations but no appointments? Work on asking about motivation. Appointments but no offers? Your analysis is too slow. Offers but no contracts? Follow up harder.
Then run the next ninety days. And read real estate investing mistakes — at least one of them will feel very familiar.
Your next step
Bring your first deal into REI Skool, my free community, and post the numbers before you sign. Experienced investors will poke holes in it, and that’s exactly what you want. Join from benlovro.com.
If you want to step back and see the whole sequence first, start at the beginner’s guide to investing in real estate.
Questions people ask
How many offers does it take to get a first real estate deal?
There’s no fixed number, and anyone who quotes one is guessing about your market. What’s consistent is that most offers get rejected, and most deals come from follow-up on earlier conversations. Make offers steadily and keep following up.
Should my first investment property be a rental or a flip?
Choose by your capital, time and temperament. Many people find a light-cosmetic property with a clear exit is the gentlest first deal. Compare options on real estate investing strategies.
What should I do if my first deal falls apart?
Figure out which stage failed — the lead, the conversation, the numbers or the exit — fix that one thing, and get back to daily activity. A dead deal that taught you something is tuition, not failure.