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Escape Your 9 to 5 and Start Your Journey Towards Financial Freedom

Escape Your 9 to 5 and Start Your Journey Towards Financial Freedom

6 min max read

We recently had Jonathan Swanson on an episode of the DealMachine Real Estate Investing Podcast. In that episode, Jonathan shared what his journey has been like for the 20 years he has spent in the real estate game. Learn how he made $25,000 on his first deal and his strategies for successful marketing and finding profitable real estate deals. In this blog, we will break down some of the key takeaways from his journey to financial freedom.

Who is Jonathan Swanson?

Jonathan Swanson is an experienced real estate investor from Wilmington, North Carolina. He first entered the real estate industry in 2004 as both a licensed real estate agent and a house flipper. Over the years, he has built a successful portfolio of long-term rentals and has recently expanded into short-term rentals. Jonathan has a wealth of knowledge and experience in the real estate market, making him the perfect guest to share his insights and strategies for finding profitable deals.

The Journey into Real Estate

Jonathan's journey into real estate began in 2004 when he purchased his first house with a partner. They initially planned to flip the house and make a substantial profit, but instead, they sold it to another investor and made a $25,000 profit. This unexpected success fueled Jonathan's passion for real estate and led him to pursue a career as an agent and investor simultaneously.

He joined Coldwell Banker and later moved to Remax, where he has been actively involved in flipping houses, managing long-term rentals, and exploring new investment opportunities such as short-term rentals.

The Motivation to Get a Real Estate License

While most real estate wholesaling does not require a real estate license, Jonathan was motivated to get his license for two key reasons. Firstly, he saw it as an opportunity to have a consistent source of income in a thriving market. He felt confident that he could leverage his network and connections to secure listings and attract buyers.

Secondly, Jonathan desired the freedom, flexibility, and independence that came with being an independent contractor rather than working a typical nine-to-five job. He wanted to have control over his schedule, make decent money, and pursue his passion for house flipping.

From a Rigorous Job to an Independent Real Estate Career

Before diving into the world of real estate, Jonathan worked a rigorous job at Maximum Healthcare, recruiting nurses and nursing assistants for home health and nursing facilities. The job demanded long hours and constant availability, including being on call from 6:00 PM to 7:00 AM. This experience cultivated Jonathan's work ethic and determination to get things done.

However, he desired a more fulfilling and flexible career that would allow him to spend quality time with his family and pursue his personal interests. Real estate provided the perfect opportunity for Jonathan to achieve these goals. His transition into real estate gave him more freedom, flexibility, and financial stability, allowing him to be present for his wife and three children. He now has the ability to attend his children's baseball games, coach their teams, and achieve a healthier work-life balance.

The First Profitable Deal

Jonathan's first profitable deal was an important milestone in his real estate journey. He received a tip from a fellow agent about a bank-owned property listed at $50,000. Recognizing its potential, Jonathan bought the property with a partner. Instead of flipping it themselves, they decided to sell it to another investor for a total profit of $25,000.

Surprisingly, all they did was install a temporary power pole to facilitate the necessary renovations. This deal showcased the profitability of real estate investing and solidified Jonathan's belief in the industry's potential for financial success.

Marketing Strategies for Finding Off-Market Deals

Jonathan emphasizes the importance of effective marketing strategies for finding off-market deals. While he's often approached by friends and other investors with potential deals, he relies on a variety of marketing techniques to ensure a consistent pipeline of opportunities. One effective method is driving for dollars, which involves physically driving around neighborhoods and identifying properties that appear distressed or vacant. By building his own targeted list of motivated sellers, Jonathan can reach out directly and offer his services.

Additionally, he leverages traditional marketing techniques such as direct mail campaigns, using customized postcards designed to grab the recipient's attention. He has also found success by attending real estate investor association (RIA) meetings and building a network of wholesalers who may have exclusive deals or compelling opportunities. These different marketing strategies have contributed to Jonathan's ability to find profitable off-market deals consistently.

"There's a lot of ways to do it, and... driving for dollars is a great way to build a list yourself that nobody else has... It's a lot more targeted..."


Wholesaling and Building Relationships

Jonathan highlights the importance of building relationships within the real estate community. He encourages attending RIA meetings and actively participating in networking events. By fostering connections, real estate professionals can find potential buyers, sellers, partners, and private lenders.

Jonathan advises making an effort to meet different types of individuals, such as wholesalers, realtors, landlords, and money lenders. Additionally, he emphasizes the value of building relationships with private lenders as they can provide the necessary financial support for real estate deals. By actively engaging with the real estate community, individuals can expand their network, learn from others' experiences, and increase their chances of finding profitable deals.

"Pretend like the RIA meeting is a party in your honor and you better be there every time... Figure out if you're compatible to do business together... Make friends with them... Everybody that needs money, get this person's contact information..."


The Best and Worst Real Estate Deals

His most profitable deal involved a pre-foreclosure property. The homeowner, who learned about Jonathan through a DealMachine postcard and his professional website, reached out for assistance. Jonathan negotiated a fair deal, which resulted in a substantial profit of approximately $140,000 after the property was fully renovated and sold. Despite some challenges along the way, this deal showcased the power of effective marketing and the potential for significant returns in real estate investing.

On the other hand, Jonathan recalls a difficult deal in which he lost approximately $10,000. This deal involved purchasing two similar properties in the same neighborhood. While one property sold successfully, the other proved challenging due to its location in a flood zone.

The additional expenses related to flood insurance deterred potential buyers and reduced the profitability of the investment. Jonathan learned valuable lessons from this experience, such as the need for thorough research and accurate assessment of market conditions and associated costs.

Achieving Work-Life Balance and Pursuing Hobbies

One of the primary motivators for Jonathan in pursuing a real estate career was achieving a better work-life balance. He wanted the freedom to spend quality time with his wife and three children. As an active father, Jonathan coaches baseball teams and attends his kids' sports events.

He also pursues his passion for car racing by participating in track days at the Virginia International Raceway. These hobbies and family activities are a testament to Jonathan's ability to achieve a fulfilling and well-rounded lifestyle while successfully managing his real estate investments.

Advice for Aspiring Real Estate Investors

Jonathan has a piece of valuable advice for those just starting their real estate investing journey. Be sure to take action and avoid falling into the trap of overanalyzing every decision. While research and analysis are essential, aspiring investors must ultimately take the leap and start investing.

Jonathan advises individuals to identify a strategy that suits their goals and interests and begin working towards it. He emphasizes the need to gain practical experience and adjust accordingly based on personal preferences and market conditions. Ultimately, success in real estate comes from actively engaging in the industry and taking calculated risks.

"You're not going to be successful at anything if you just analyze it to death all the time... Figure out something you want to do and just go do it... If you don't like it when you do it, don't do it again... If you love it and it made you a bunch of money, go do it again."



We hope that Jonathan Swanson's journey in the real estate industry serves as an inspiration for aspiring investors. Through his determination, marketing strategies, and willingness to take calculated risks, he has built a successful and fulfilling career in real estate. His story showcases the potential for financial success, work-life balance, and personal growth within the industry.

By following Jonathan's advice and leveraging effective marketing techniques, aspiring investors can find profitable off-market deals and achieve their own goals in real estate investing. Remember, success comes from taking action and embracing the opportunities that real estate offers. So go out there, build your network, market wisely, and take those important first steps towards your own real estate success story.

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.