NFL Player to Real Estate Wholesaler: Winston Went from $0 to $300K in His First Year

NFL Player to Real Estate Wholesaler: Winston Went from $0 to $300K in His First Year

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Winston Wright went from playing in the NFL and working as a youth pastor to making over $300,000 in his first year wholesaling real estate. In this post, we'll explore Winston's journey and his tips for getting started in wholesaling.

Winston's Background: Football, Marriage, and Finding a New Path

Winston played college football at South Dakota State before having a stint in the NFL with the Tennessee Titans and playing in the CFL. After returning home, he got married and had kids, which prompted him to transition into youth ministry as a source of steady income.

However, as Winston shared:

"As much as I loved being a youth pastor, my wife was a stay at home mom. I had to figure something out as far as additional income, we just wasn't making the ends meet right. And it was right after the pandemic, and I had a buddy in town who was doing wholesaling and fix and flips. I went and got lunch with him, and all you had to do is show me what I needed to do, and that was off to me."

Like many young married couples, Winston realized he needed to supplement his income to provide for his growing family. A chance meeting with a friend doing wholesaling opened his eyes to a new opportunity.

Getting Started in Wholesaling with Just One Deal

Winston's friend showed him how he found wholesale deals on Craigslist, which sent Winston down the rabbit hole of YouTube videos and online courses about wholesaling.

Driving for dollars - essentially driving around looking for vacant or dilapidated properties - stood out as one of the best ways to find deals. Winston discovered Zack Booth and Wholesaling Inc, invested in their training program, and hit the streets looking for wholesale opportunities.

It didn't take long for Winston's first deal to materialize:

"That very first deal was actually a duplex and a triplex, and I made 10K. I made 5K on each."


With $10,000 in profits from his first two wholesale deals, Winston was able to provide for his family in a meaningful way:

"We went to the grocery store and I told my wife, we filling it up. And so it was a good feeling, man, to be able to stock the fridge, stock the cabinets, man, with some meals. Paid off all the credit cards to get started in the business as well."


Scaling Up: $300K in Year One through Driving for Dollars

Winston was off to the races after his first ten grand. In his first full year wholesaling real estate, he brought in $300,000 in revenue.

His go-to strategy was driving for dollars. Winston hired a driver for $1500 every two weeks plus a percentage of each closed deal. The driver went out finding distressed properties five days a week and would pin over 2000 properties in a week. Winston then had a system for marketing to those leads via text, phone calls, and mailers.

Between driving for dollars and Winston's acquisition skills on the phone, he closed deal after deal, exceeding all his initial financial goals.

Lessons Learned: Patience, Vision, and Balance

When reflecting on key lessons he applied from his football and ministry backgrounds, Winston emphasized patience, vision, and work-life balance:

"Patience, man. The youth are amazing. They keep you young...Me and my wife, we sit down, we have goals that we want for our family, and when things get hard, man, that's what you lean on, the vision and the goal set."

He also realized after almost hitting $1 million revenue in year two that he needed to pull back and focus more on quality of life:

"I realized, like, man, my life was good at 300K. What do I need a million for? I would rather have exactly what I need and a little bit in time with my family than a vanity number of a million bucks."

Winston's Advice for New Wholesalers

For those just getting started in wholesaling, Winston suggests:

  • Watch wholesaling content from DealMachine and other successful investors
  • Don't get stuck in information overload - take action!
  • Drive for dollars if you can. It's proven and gets real, live data.
  • Have a sincere "why" that motivates you through long days on the road
  • Be willing to put in the work driving and pinning hundreds of properties
  • Trust the process and adopt the identity of a successful wholesaler

Winston's story proves that with hustle, perseverance, and the right mindset, you can build a highly lucrative wholesaling business. If he can go from $0 to over $300k in a year, you can absolutely find success in this business too!

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.