From Server to Real Estate Wholesaler: Jason's First Deal

From Server to Real Estate Wholesaler: Jason's First Deal

4 min max read

Do you ever feel like all the financially successful people you know made their money in real estate? Our guest today, Jason Marks, was driven into real estate investing by that same realization. He was originally planning to buy rental properties, but then discovered real estate wholesaling - and made $22,000 on his first deal without even having to put up the money to buy the property!

Jason has since gone on to do over $500k per year wholesaling real estate. So if you're looking for a way to replace your W-2 income, you'll want to keep reading to find out exactly how Jason got his start.

How Jason Made $22K Wholesaling 20 Acres

So, how did Jason make that first $22k check?

When I first found wholesaling, I had a real estate mentor. When I told him about wholesaling, he said his audio/video guy was doing some deals on the side. I met up with him for lunch and he happened to be working on a deal, so he invited me to help negotiate with the seller and get my feet wet.
I ended up getting a 20 acre property under contract for $100k. We wholesaled it to a trucking company looking for land to store their trailers. Made a $54k spread and split it 50/50, so $22k for me!


The total spread was $54,000 between the contracted purchase price and the amount the trucking company agreed to pay.

Since Jason's mentor was already doing some marketing, he simply leveraged that lead. When it came in, he sent Jason out to speak with the seller.

How did Jason's partner know $100k was the right price to offer?

Jason wasn't quite sure - that was the advantage of having an experienced mentor on his side! His mentor could see it was a good deal based on the size and despite the environmental issues we'd need to address before selling.

Jason was able to learn so much just by watching his mentor take action before having everything figured out. He got it under contract before lining up an exit strategy because he knew based on the numbers that it was a great buy.

The lesson: you don't need to overanalyze every detail upfront. If you know a deal is good based on your math, take action! The solutions will show themselves later.

Finding Motivated Sellers from Tax Delinquent Lists

How did Jason's mentor source this 20 acre discounted property?

Jason said it was simple actually. He was marketing to tax delinquent owners using direct mail. They used printed letters with handwritten envelopes so they stood out.

Every county publishes a list of property tax delinquencies that is available for free. They emailed the tax office and the tax office sent over a spreadsheet we could mail merge into personalized letters.

If you're not familiar, mail merging allows you to input custom fields like the owner's name and property address into letters so each one feels personalized. The data comes formatted in Excel, which you can connect to Word to auto-populate documents.

So you don't need any special software or AI! Just request the latest tax delinquent list from your county tax office and mail merge letters to motivated sellers.

Be sure to "scrub" the list first by removing commercial properties or vacant land that won't work for your needs. Focus on sending letters only to viable leads.

When motivated sellers respond to your letters looking for a way out, you may be able to negotiate huge discounts because of their past-due tax situation!

Overcoming Analysis Paralysis as a New Wholesaler

Even experienced investors struggle with "analysis paralysis" at times when evaluating deals. We want to run the numbers five different ways, triple-check comps, look at multiple exit strategies, and so on before feeling ready to pull the trigger.

Jason explained how working with a mentor on his first deal helped him overcome this:

He was able to watch his mentor take action before having everything lined up perfectly. He got it under contract before finalizing an exit plan because he knew it was a good buy based on the math.

Jason said:

"Great advice from Max Maxwell that helped me - "What you know should give you certainty." Like if you wear Nike sneakers and know exactly what they retail for...then you find a legit pair being sold for $50 somewhere, you don't hesitate - you know it's a crazy deal even if you already own multiple pairs."


The same logic applies to wholesaling deals - if you know your numbers work, just get it under contract. The solutions will show themselves later!

Growing a Side Hustle into a Full-Time Business

After that first taste of success, Jason and his wife knew wholesaling was legitimate. They decided to systematize the direct mail marketing process and keep wholesaling on the side while still working their full-time jobs.

They started sending out about 50 letters per week targeting tax-delinquent owners in their area. It was really fun for him and his wife to do together as a couple. They were making great money part-time just doing it on nights and weekends.

As he built relationships with more experienced investors, Jason had access to more resources like off-market deal pipelines to grow the business. However, he eventually learned an important lesson...

"What got you here, won't get you there."

At first, it's all about hustling and grinding to make as much as possible. But at a certain point, you have to think about simplifying and building the right team so that your business funds the lifestyle you actually want.

For Jason, it wasn't about having the biggest wholesale operation out there. It was about creating income streams that afford him more freedom to live life with his wife and family.

Now they've simplified to focus on wholesaling for recurring cash while acquiring rentals for long-term wealth. This balance made him much happier than constantly chasing the highest revenue possible.

Everyone is different, so build your team based on your personal lifestyle goals rather than what other people are doing!

Jason's story shows that you don't need any special background to have success wholesaling real estate. With the right systems, mindset, and support, you can replace your W-2 income faster than you might imagine possible.

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.