How hard is wholesaling real estate for someone starting with no experience, no deals, and a limited income? To answer that question, we reviewed Michael McDonald’s story from the DealMachine REI Podcast and broke down the decisions, systems, and financial milestones that helped him leave a low-paying W-2 job and build a real estate wholesaling business. We researched his journey carefully to understand what actually worked and why.
Michael’s story is motivating, but it is also instructional. He did not rely on luck, shortcuts, or perfect timing. He followed a repeatable process that many new wholesalers can model today. This article explains how he got started, how he closed his first $23,000 deal, and how he built a business capable of supporting his family. Along the way, it gives a clear and honest look at how hard wholesaling real estate really is.
Before real estate, Michael worked as a nutritionist, earning about $30,000 per year. As his family grew, he realized his income left little room for savings or flexibility. When he and his wife learned they were expecting a child, the pressure to change became real.
Michael decided to invest $20,000 into a three-day real estate training event. The program focused on wholesaling as a way to earn income without owning property or using large amounts of capital. His goal was simple. If he could close one solid deal, he could recover his investment and prove the business model worked.
At that point, he had no background in real estate. What he did have was urgency and a willingness to take action. When people ask how hard is wholesaling real estate, this is often the first challenge. Taking consistent action matters more than having experience.
Shortly after the training, Michael connected with an experienced wholesale real estate investor who became his mentor. This relationship gave him clarity and accountability. Instead of guessing what to do next, he followed a clear process.
One of the first strategies he implemented was driving for dollars. This method remains one of the most common entry points for new wholesalers because it requires more effort than money.
Driving for dollars involves driving through neighborhoods and identifying vacant or distressed properties. These properties often belong to owners who may be open to selling off-market.
Michael handled the process manually at first.
He repeated this process until he had mailed more than 2,000 postcards. It was time-consuming, but it worked. The key was consistency. This shows that wholesaling real estate is not complicated, but it does require follow-through.
Today, many investors use tools like DealMachine to automate these steps, track properties, and contact owners faster. Michael’s experience shows the system works whether it is done manually or with software.
One postcard eventually led to a callback from a motivated seller. Michael moved quickly, even though the deal became complicated.
Despite the challenges, he successfully closed the assignment and earned about $23,000 on his first wholesale deal. For someone earning $30,000 a year, this single deal changed his outlook.
The deal was far from perfect. Michael ran into problems that many first-time wholesalers experience.
The property went under contract for $180,000. The buyer’s lender required an appraisal of $211,000. That gap created roughly $30,000 in assignment fees, which Michael split with his mentor after costs.
More important than the money was the confidence it created. He proved he could find deals, negotiate contracts, and close transactions.
Michael did not quit his job based on motivation alone. He focused on replacing income responsibly.
To replace a $30,000 annual W-2 income, a wholesaler must account for:
Instead of thinking in terms of annual income, Michael focused on deal volume and average assignment fees. If a wholesaler averages $10,000 per deal, replacing $30,000 in income requires three deals per year. Most investors aim higher to create a buffer.
Michael reinvested early profits, built a cash reserve, and waited until his deal flow was consistent before relying on wholesaling as his primary income.
After his first deal, Michael focused on building consistency rather than chasing quick wins. He expanded beyond driving for dollars by adding multiple lead sources.
This shift reduced reliance on a single strategy and stabilized deal flow.
Michael’s growth followed a pattern seen in many successful wholesalers.
Stage One: Manual lead generation, like driving for dollars. This stage requires time but little money.
Stage Two: Scalable marketin,g such as direct mail and list pulling. Costs increase, but volume improves.
Stage Three: Virtual wholesaling, where deals are sourced and closed remotely using systems and scripts.
Each stage reduces time per deal while increasing reach. Tools like DealMachine support this evolution by centralizing property data, owner information, and follow-up as the business scales.
When Michael moved to Las Vegas, he worried about losing momentum. Instead, he discovered virtual wholesaling.
One early virtual deal came from a seller in Arkansas. After a short text exchange and one phone call, he put the property under contract without visiting it.
Virtual wholesaling allowed him to expand beyond local markets while maintaining deal flow.
Since getting started, Michael has completed more than 200 wholesale deals. Wholesaling allowed his wife to stay home with their children, helped his family travel, and gave him the ability to start buying rental properties.
Wholesaling created income first. Rental properties provided long-term stability.
Michael’s advice for new investors is simple.
His results came from steady execution.
So, how hard is wholesaling real estate today? It is not easy, but it is simple. The strategies Michael used still work, and the tools have improved.
With clear income targets, consistent lead generation, and patience, replacing a W-2 income through wholesaling is achievable for many investors. Michael’s story shows what is possible when inspiration is paired with structure.
Real estate wholesaling involves securing a property under contract and assigning that contract to another buyer for a fee.
It requires consistent effort, lead generation, and follow-up, but it does not require prior experience or large amounts of capital.
He used driving for dollars and mailed handwritten postcards to distressed property owners.
Yes. Many investors close deals virtually using photos, phone calls, and online data.