Cold Calling Tips for Landing Your First Real Estate Deal

Cold Calling Tips for Landing Your First Real Estate Deal

3 min max read

Getting your first real estate wholesaling deal can be a major milestone on your journey to replacing your W-2 income. Our guest Dillano Medina has done just that, replacing his full-time job income wholesaling real estate for several years now.

In this post, we'll share the key tips Dillano learned about effective cold calling to land his first (and many subsequent) deals. Whether you're just starting out or looking to ramp up your business, this post has gold for you!

Dillano's First Deal By the Numbers

Let's start by hearing some key stats on Dillano's journey:

  • It took him 11 months from starting to learn wholesaling to land his first deal
  • He made $5,319 on his first deal - not bad!
  • Since then (starting in 2019), he's done over 60 deals

So while it took some persistence starting out, he built momentum and has wholesaled consistently at an impressive clip since that first one.

Why Cold Calling Worked Where Other Strategies Didn't

Dillano actually started out trying a bunch of different real estate marketing strategies he learned, including:

  • Pulling lists and cold calling
  • Using a CRM and sending targeted postcards

He struggled at first and wasn't gaining traction.

Then around months 7-8 of his journey, he discovered DealMachine. This changed everything in terms of having an effective system to find and organize leads while driving for dollars.

"I wasn't able to track my routes. I wasn't able to have a CRM full of leads that I could go back home and automatically start targeting."

With DealMachine, the leads and organization system clicked for Dillano. He was able to efficiently:

  • Drive routes and visually map properties in the app
  • Export lead lists automatically
  • Have the data centralized instead of scattered across notes/spreadsheets

This was the game changer to ramp up his marketing and get his first deal! An automated lead capturing and management system can be invaluable for efficient and scalable cold calling.

Why Hand Dialing Worked Better Than Robocalls

Once Dillano had his DealMachine lead pipeline established, he employed a couple of cold calling approaches:

  • Using a robocall service
  • Personally hand dialing leads

He found that hand dialing the driving-for-dollar leads from DealMachine converted at a much higher rate.

There were two key reasons for this:

  1. Calls from his personal number didn’t show up as spam
  2. He was able to call leads back more persistently when they didn’t initially answer

Robocall services often can’t double dial numbers or be as targeted when reaching back out. The personal touch won the day!

Dillano was able to take one DealMachine lead from his first call of the day straight through to getting a property under contract. This ended up being his first wholesale deal that kicked off his side hustle business.

Also, now with unlimited contact information in DealMachine it has never been easier or simpler to find information on the owner. All you have to do is open up the lead and contact card, copy the phone number, enter it into your dial pad, and call.

Key Takeaway: While automation has its place, combining it with personal outreach can dramatically boost conversions.

One Added Tactic to Find Motivated Sellers from Driving

Driving for dollars is Dillano’s #1 source of quality off-market leads. He shared one additional tactic he’s using when driving that’s uncovered great deals:

When he sees a rundown/vacant property, he will literally stop and leave a sticky note with his phone number. He emphasizes not to sleep on this tactic!

Some investors even will order door hangers and run up and put door hangers on properties while they are out driving for dollars.

Even when no owner info is available, people will call him back about properties:

  • Neighbors with info
  • Relatives of deceased owners
  • Other parties with interest

In fact, he closed a recent $15,000 deal from someone calling him back about a property with limited owner information. Don’t underestimate old-school marketing! Simple sticky notes can uncover deals that may otherwise be buried.

So there you have it - Dillano's top tips for cold calling your way to real estate gold:

  • Have an automated lead capturing system - DealMachine
  • Hand dial your hottest leads
  • Leave sticky note call back numbers while driving for dollars

If you implement even one of these strategies consistently, you’ll be that much closer to landing your first deal!

Samantha Ankney

About Samantha Ankney

Samantha has been a media specialist for DealMachine for 2.5 years. She produces, edits, writes, and publishes all media that is distributed to the DealMachine and Real Estate Investing community.