“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. 

This notion of being penalized for success was perplexing for Ryan. Out of all the downsides of his job—the after-hours calls from his boss that he was expected to answer, dealing with poor management, and working up to 80 hours a week—this pay cut was the last straw. 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 that I’m about to share 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

It was the end of 2019. Ryan and Megan were in a period that should have been filled with anticipation and joy for their family as they awaited the arrival of their third child. 

Instead, uncertainty loomed. Despite the lucrative nature of his job in the budding field of fiber optics, the instability and lack of appreciation left Ryan yearning for change. He was caught in a dilemma: a high-paying position that offered little in terms of job satisfaction and stability. And to make matters worse, the company he worked for just decided to cut a large chunk of his pay because he was making too many sales.

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 but had been paying them very little attention. Ryan wasn’t initially interested in the idea of wholesaling, and the idea of a “30-day challenge on social media” seemed a bit like a gimmick at the moment, so he declined.

But after some thought and some persistence from Megan, he decided to give it a go. As it turns out, this challenge not only introduced him to the fundamentals of wholesaling but also ignited a passion for real estate that was previously untapped.

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.

Contrary to his later experiences, Ryan’s first deal came from word of mouth (in this case, that meant telling people around him at dinner what he was doing) and did not involve intricate negotiations directly with a seller. Instead, it was the process of learning on the fly—figuring out how to assess the value of properties and the cost of needed repairs with limited prior knowledge in this area. 

Despite these initial uncertainties and the steep learning curve, Ryan’s persistence paid off when he secured his first real estate deal. This pivotal moment was not only a testament to the validity of his new career focus; it also resulted in a significant payoff, earning him an $8,500 finder’s fee. 

Like many investors who came before him say, this deal was massively important. And not just because of the $8,500 check—that was just the icing on the cake. This deal was a proof of concept that wholesaling as a strategy works. In other words, the business model was proven right in front of his eyes.

Ryan admits he was still “terrified” of wholesaling at this point since he still had very little knowledge and understanding of the industry. Nevertheless, with the check in hand, he knew that this was the path forward for him and his family.

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, as it turns out, would never set foot in his old office again.

Scaling Up and Embracing Technology

Ryan and Megan’s focus at that point then became getting more deals and repeating the process. From the very beginning, they knew that they wanted it to be a family venture, even packing up the kids and bringing them on business trips to ensure that everyone was benefiting from experiencing the lifestyle that was bringing them so much success.

They needed reliable, efficient tech to manage processes and allow them to actually find success while traveling to new markets and cities to explore investment opportunities. Thanks to DealMachine, the tech platform at the center of the 30-day challenge, they were able to travel while still building and working on their business.

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 years of their business:

  • First full year (2020): Achieved 73 wholesale transactions with no standard operating procedures (SOPs) or employees—just Ryan and Megan working together.
  • Following year (2021): Completed 113 wholesale transactions, indicating significant growth. This year also saw the introduction of a transaction coordinator (TC) and a salesperson, though they quickly quit. A new TC was hired, who eventually took on sales as well due to competence in this area.
  • Year after (2022): Conducted 45 wholesale transactions, which might seem like a decrease but was part of a strategic shift to focus on quality and integrate construction into their business model. The team grew to eight people, and the average assignment fee increased to $10,500.
  • Portfolio growth: From seven rentals in 2020 to 12 by the end of 2021, and then expanding their portfolio to 30 properties.
  • Financial highlights: In 2021, they grossed $575,000, and in 2022 broke over the million-dollar mark in revenue.
  • Operational shift: Started their own construction crew in 2022 to better control the renovation quality and timeline of their investment properties.

Networking and Community Building

In their pursuit of growing their business, Ryan and Megan Haywood not only built relationships with city officials but also mended fences with local real estate agents who were initially wary of wholesalers. Their efforts in renovating distressed properties across St. Joseph, Missouri, garnered Ryan the nickname “golden child” from the mayor, underscoring the impact of their work on the community’s fabric. 

This special recognition from city leadership demonstrated the benefits of their strategic relationships, highlighting how working closely with city officials was instrumental in smoothing the path for their projects and fostering an environment of mutual benefit.

These partnerships proved to be highly important in navigating the complexities of real estate development, from regulatory compliance to accessing new opportunities that aligned with their mission to uplift the community. Because the city officials (people who are often the gateway to successfully securing permits and zoning for building projects around a city) could physically see that Ryan was creating positive change, they were happy to help him. 

Some of these officials, with deep knowledge of the city’s housing, even became a source of leads for their business and guided them to properties and areas around St. Joseph that needed change. Alongside this, their engagement with agents eventually shifted from skepticism to collaboration as they demonstrated the value and professionalism they brought to the table with these relationships as well.

For Ryan and Megan, the lesson was clear: Building a network that includes both city officials and real estate professionals can significantly amplify an investor’s ability to effect positive change while scaling their business effectively.

Lessons Learned

Looking at Ryan Haywood’s journey through the real estate landscape, there are several lessons we can learn from them. 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:

Embrace community engagement

Ryan’s success was significantly bolstered by building strong ties with community leaders and real estate professionals. This highlights the value of networking, not just for deal flow but for fostering a supportive ecosystem that can propel your business forward.

Leverage technology for efficiency

Utilizing a real estate tech platform allowed Ryan to scale his operations by streamlining the process of identifying and managing potential deals. For investors, embracing such technologies can enhance productivity, allowing more time to focus on strategic decision-making.

Adopt a mission-driven approach

Having a clear mission, such as improving the community, can differentiate you in a crowded market. Ryan’s focus on revitalization projects earned him the “golden child” nickname, underscoring the impact of aligning business goals with community values.

Final Thoughts

Ryan Haywood’s path in real estate is a compelling story of strategic growth, innovation, and impactful community engagement. His progression from executing individual deals to achieving over 400 transactions is not merely a story of personal success but a blueprint for investors aiming to elevate their business practices. 

Haywood’s story highlights the critical role of embracing technology to streamline business operations, the power of networking in your local community and beyond to unlock new opportunities, and the impact that can come from fostering both business growth and community development.

For investors looking to replicate Ryan’s success, the key takeaway is the value of strategic adaptability—integrating new tools/methods and pushing forward while also remaining rooted in the community’s welfare and having a bigger “why.” This story shows that achievements in real estate require not just good financial judgment but a vision that extends beyond personal gain.

This article is presented by DealMachine


DealMachine empowers real estate professionals to discover and invest in off-market properties with ease, offering a comprehensive app that guides you every step of the way. From identifying potential investments to instantly accessing high-quality homeowner data for informed decision-making, we make investing simple and effective. Click to start expanding your portfolio today!

Note By BiggerPockets: These are opinions written by the author and do not necessarily represent the opinions of BiggerPockets.

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