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Betting on Wholesaling: One Couple’s Journey Into Joint Investing

Betting on Wholesaling: One Couple’s Journey Into Joint Investing

4 min read
Marcus Maloney

Marcus Maloney is a value investor and portfolio holder of residential and commercial units. Marcus has been named th...

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I want to invite you into a conversation my wife and I had, along with a bet and ultimately a successful real estate deal. Stay with me; I promise you’ll get a lot out of this.

The Backstory

I’ve documented my journey as a wholesaler for years on BiggerPockets. From my initial foray into real estate investing, where I focus on wholesaling, up to my many wholesaling articles, and even being interviewed by Brandon and David on the BiggerPockets Podcast episodes 386 and 386.5.

I’ve accomplished some goals and challenged myself with new milestones to hit, but there was one that was ever so elusive: I wanted to prove to my wife that she could do it, too, and we could work together.

I’ve always been the entrepreneur of the family and she was always the one that wanted surety and consistency. She believed this came in the form of a biweekly paycheck from an employer. However, the COVID-19 pandemic had other plans for her.

Due to the pandemic, that sense of security was disrupted. She found herself scrambling to find a way to offset some of the income she was losing due to “restructuring” on her job.

So what was she to do?

As her husband, I had her back, but I had to throw a bit of “I told you so” in there.  I wanted her to know that nothing is ever secure when you don’t have control.

So this brings us to an inflection point.


The Bet

After a rather lengthy discussion about how it wasn’t right, followed by creating a plan for us going forward and how she was going to pivot, I set the trap.

I always wanted her to work in the business with me, but she had reservations. Like most people, she was concerned about the following:

  • Dislike of sales
  • Inconsistencies with deal flow
  • Money for marketing
  • Medical and dental insurance
  • Tax payments
  • And too many other excuses to list

Although she was living with proof that wholesaling works, she still had reservations, even though every excuse she raised I had already overcome.

It is discouraging to see so many people betting on their employers to provide surety and security for them instead of betting on themselves. My wife is like tens of millions of people that know it’s possible to be an entrepreneur but can’t muster up the courage to take the leap.

Related: 8 Reasons You Shouldn’t Mix Family With Real Estate Investing

Steve Harvey says it like this in his book Jump: “You don’t have to know exactly what your journey will be or the steps that will bring you to your dream — just be open to the process, and be open to the path. Seize the opportunity.”

So I challenged my wife. I told her I work with many other aspiring investors. If I can work with them to take the leap, get out of their comfort zone, and become successful entrepreneurs, I can do the same for her.

All I needed her to do was believe just a little.

I had her. When she said, “Well, how is that going to happen?” My reply was, “We are going to get you to close one deal and then many more and you’ll see the power of real estate.

The bet was that if she closed her first deal within six months she wouldn’t return to work, but if she didn’t, she would go back to looking for work.

She agreed and we set out on this journey.

The Strategy

I needed to get her going right away.

I thought that with her ability to talk on the phone, cold calling would be a great way to get her started. However, I wanted her to ease into the conversation. She didn’t know all of the lingo, and I wanted her to be confident while speaking on the phone. Text messaging was the way to take the edge off and get her settled in.

The Steps

Step 1: We pulled a list from PropStream of absentee owners with 50% equity and above in certain zip codes in Chicago (we’re virtual wholesaling).

Step 2: Within PropStream, there is a skip tracing function to get telephone numbers, and that’s what we did.

Step 3: We sorted the Excel spreadsheet with the following:

  • Owner Names
  • Owner Mailing Address
  • Site Physical Address
  • Landline Phone Number
  • Mobile Phone Number
  • Equity Position

Step 4: We created an account with Twilio for text messages. You can use other services, such as Sendii, Text Magic, or Text-Em-All. There are tons of them; take your pick.

Step 5: We purchased a number from Twilio, and we created a simple message. “Hi, my name is Stephanie and I am curious to know if you’re looking to sell your property or know someone in the area looking to sell.”

Step 6: We created canned reply messages and hired a VA from Upwork to respond to sellers with canned messages through the Twilio app.

Step 7: Start campaign.

Step 8: The VA forwarded all communication of potential sellers to Stephanie via email, then Stephanie would call the sellers.


The Results

She spent a little over $1,000 setting up this campaign and closed her first deal in seven months. We would have closed this deal a lot sooner (around four months), but the seller had title issues that the attorney had to clear up.  Her $1,000 went towards pulling the list, skip tracing, setting up Twilio, and paying the VA.

As I said before, she is great at talking on the phone but did not know the lingo. The text messaging helped her ease her way into the conversation.

Related: The Ultimate Beginner’s Guide to Real Estate Wholesaling

Here are some numbers from the campaign results

  • Sent messages: 6,418
  • Message responses: 338
  • Message response rate: 5.2% (we could’ve done better)
  • Interested respondents: 5
  • Closed deals: 1 ($13,000)

I marketed the deal to my buyers list and had many interested buyers on the deal, with one even offering over ask. For those thinking she was only able to do this because of my buyers list, I do believe she would have moved this deal in Facebook investor groups as well.

Most people would consider this to be a successful campaign, but I believe we could have done better. She had three other sellers on the hook. Now she has them on a long-term follow-up so they may come back around.

Her and I both being from Chicago, we had boots on the ground to walk the property, take pictures, and meet the seller to let buyers in. For markets where you don’t know anyone, use BP as a resource to find someone on the ground.

With the assistance of her loving husband, she has a different perspective on real estate wholesaling and being an entrepreneur. I’m glad I was able to help her see the possibilities.

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What was the push that got you into real estate? How can you use that to inspire others?

Share your starting-out story in the comments.