From Toxic Workplace to Real Estate Success How One Family Transformed Their Future

“You’re making too much money.”

That’s what echoed in Missouri native Ryan Haywood’s ears after his boss decided to slash his commissions—a “sales haircut,” as it’s bitterly known in the industry.

He didn’t realize it at the time, but this setback was about to unveil a path that would lead his family toward the future that Ryan and his wife Megan had dreamt about.

Ryan’s story is not just a testament to his determination to build his wealth on his own terms. This story is about his strategic, practical approach to building a truly successful real estate company in the face of uncertainty, full of solid insights that every investor should hear.

Ryan’s Journey From Sales to Real Estate

Ryan knew something had to change; he just hadn’t yet realized what that change would be. Shortly after receiving this news, Megan and Ryan had their third child. This meant Ryan was on paternity leave and suddenly had extra time on his hands. He wasn’t sure what his next steps would be—all he knew was that he couldn’t go back to the toxic workplace at his current 9 to 5 job.

It was during this time that Ryan’s wife Megan stumbled across a 30-day wholesaling challenge on Instagram and brought it up to Ryan. They had dabbled in real estate investing years prior with a couple of rentals. 

Initial Steps and Challenges

After pushing past his initial reluctance, Ryan went full steam ahead on trying to win the challenge—this meant landing your first wholesale deal within 30 days. This entailed driving for dollars to find distressed properties, reaching out to the homeowners (in Ryan’s case, via direct mail), and securing a purchase contract from the seller that Ryan would then assign to an end buyer.

When the challenge was all said and done, Ryan ended up landing two deals in 30 days, totaling $28,500. This number was the base salary at his last job. He had successfully escaped the rat race and would never set foot in his old office again.

Scaling Up and Embracing Technology

Because of their adoption of technology, scaling came naturally for them. Wholesaling is a numbers game—to grow your business; you need more leads, more marketing, and people in key positions to help ensure a smooth pipeline. DealMachine helped them with all of this and then some, allowing the leads to keep flowing and marketing to continue on autopilot while Ryan and Megan focused on the most important parts of the business and spending time together as a family.

To get a deeper insight into how they scaled from getting their first few deals, here’s a breakdown of the numbers in the first couple of years of their business. 

In 2020, Ryan and Megan completed 73 wholesale transactions without employees or SOPs, growing to 113 transactions in 2021 with the addition of a transaction coordinator and a salesperson, although both soon quit. By 2022, they shifted focus to quality over quantity with 45 transactions, grew their team to eight, increased their portfolio to 30 properties, started a construction crew, and surpassed $1 million in revenue, up from $575,000 in 2021.

Final Thoughts

By achieving over 400 deals so far, Ryan has not only showcased what’s possible with dedication and strategic planning but also exemplified the significance of adopting certain practices for long-term success.

Here are some key takeaways from his experience, each providing a blueprint for how to navigate the complexities of real estate investing effectively:

1. Embrace community engagement
2. Leverage technology for efficiency
3. Adopt a mission-driven approach

For investors looking to replicate Ryan’s success, the key takeaway is the value of strategic adaptability—integrating new tools/methods to push forward while also remaining rooted in the community’s welfare and having a bigger “why.”

If you’re inspired by Ryan’s journey and looking for tools to help guide your own path to success in real estate investing, consider exploring platforms like DealMachine. While a tool alone cannot guarantee success, having the right technology can significantly streamline your processes and help you focus on what truly matters.