How to start Wholesaling in Real Estate: Advice from a 20-Year Veteran

After wholesaling for over 20 years, managing 50 investor agents, owning multiple rental properties, and being deeply entrenched in the world of real estate investing, I can confidently say that wholesaling is both an art and a science. I’ve seen it all—every high and low, every success and misstep. I’ve worked with small-scale investors, global clients, and even Fortune 500 companies. But one thing remains constant: wholesaling is one of the best ways to get started in real estate with minimal capital, and it’s an invaluable foundation for any investor’s journey.

I understand the excitement and nervousness of wanting to dive into wholesaling, and I know how challenging it can be to navigate when you’re starting out. You have to juggle understanding market trends, learning negotiation techniques, and developing a network that can help you move deals fast. It’s a lot to take in, but if you’re willing to put in the work and adopt the right strategies, wholesaling can open doors you never thought possible.

In this comprehensive guide, I’m sharing everything I know about wholesaling—from the nuts and bolts of what it takes to succeed to the common pitfalls you must avoid. By the end, you’ll have a roadmap that can guide you whether you’re a newcomer or a seasoned investor looking to refine your strategies.

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Why Wholesaling is the Perfect Gateway to Real Estate Investing

Wholesaling offers a unique advantage: you can get started with little to no capital. Unlike traditional real estate investing, where you need cash or financing to buy properties, a wholesaler’s role is to secure contracts and then sell those contracts to other investors. You’re acting as the middleman, connecting sellers who want to get rid of their properties quickly with buyers looking for good deals.

For those reasons, wholesaling is a great way to learn the basics of the real estate market. You’ll develop an eye for spotting good deals, hone your negotiation skills, and build a network of buyers and sellers. It’s fast-paced and often challenging, but it also offers invaluable experience that sets the stage for future ventures like fix-and-flip, buy-and-hold, or even more advanced strategies like “Subject To” and BRRRR.

How I Started in Wholesaling and What I’ve Learned

I got into real estate after working as a licensed financial advisor, and even though I had a solid grasp of finance, real estate was a whole new ballgame. I quickly realized that having a theoretical understanding of markets wasn’t enough; I needed to be in the field, talking to sellers, buyers, and other investors daily.

One of the first lessons I learned was the value of speed and flexibility. Wholesaling is a people business, and deals can be made or lost in an instant. I remember missing out on some great opportunities early on because I couldn’t act fast enough or didn’t have the right buyer lined up. Those experiences taught me to always stay ready and build a reliable list of investors so I could move on deals as quickly as possible.

Building a Network of Investors: The Key to Success

In wholesaling, you’re only as good as your network. That means you need to prioritize building a list of serious, cash-ready buyers. There are a few ways to do this:

1. Buy a List of Investors: Yes, you can purchase a list of cash buyers from various platforms. This gives you an initial group to work with, but be prepared to vet each one to ensure they’re reliable.

2. Create Your Own List: A more organic approach is to generate leads through a website or social media. Offer value, whether through educational content, case studies, or free resources like eBooks. Over time, you’ll attract investors who are interested in what you have to say and will be more willing to work with you.

3. Leverage Networking Events and Social Media Groups: Attend local REI (Real Estate Investment) meetings, join Facebook groups, and engage with other investors on platforms like LinkedIn or BiggerPockets. Building relationships takes time, but the payoff is worth it.

A strong investor list allows you to close deals faster and gives you leverage when negotiating with sellers. And don’t forget to keep expanding your list—real estate is cyclical, and having a diverse pool of buyers ensures you’ll always have someone interested, no matter the market conditions.

Finding Properties: Proven Strategies that Work

Finding the right properties is crucial, and there are three main strategies to get you started:

1. Driving for Dollars: This is one of the most effective methods, especially when you’re new. It involves driving around neighborhoods looking for distressed properties—houses with overgrown lawns, peeling paint, or boarded-up windows. These are signs of motivated sellers who might be willing to let go of their property for a discount.

2. Direct Mail Campaigns: Send postcards or letters to property owners who might be interested in selling. This is more of a numbers game, so be prepared to send a lot of mail before you get a response. When you do, though, it’s often from sellers who are genuinely interested in selling.

3. Working for Another Wholesaler: If you’re just getting started, consider working for a more established wholesaler. This will give you hands-on experience and allow you to learn from someone already successful. Plus, you’ll build connections that can be invaluable when you branch out on your own.

Deciding Your Role: Acquisitions vs. Dispositions

Wholesaling is divided into two main roles: Acquisition Wholesaler and Disposition Wholesaler. Each role has its own set of responsibilities:

• Acquisition Wholesaler: Your job is to find the deals. You’re reaching out to homeowners, negotiating contracts, and ensuring the deal makes sense financially. This role requires strong negotiation skills and an eye for identifying good opportunities.

• Disposition Wholesaler: Your job is to find buyers for those deals. You’re marketing properties, showcasing the value of the investment, and negotiating with other investors. This role is more about sales and building relationships with cash buyers.

Choose the role that fits your strengths. If you love talking to sellers and working out the numbers, focus on acquisitions. If you’re more of a people person and enjoy selling, focus on dispositions. Of course, you can do both, but starting with one will help you become a master in that area.

Avoiding Common Pitfalls in Wholesaling

In my 20 years of wholesaling, I’ve seen a lot of beginners make the same mistakes. Here are some of the most common pitfalls and how to avoid them:

1. Not Doing Enough Research: Don’t rush into deals without understanding the market. Make sure you know the property values, the costs of repairs, and the potential ARV (After Repair Value).

2. Overestimating ARV or Underestimating Costs: Many wholesalers get into trouble by overestimating what a property will sell for after repairs or underestimating the costs involved. Always be conservative with your numbers.

3. Lack of Consistency: Wholesaling is not a get-rich-quick scheme. It requires daily effort and consistency. Whether you’re sending out direct mail, cold calling, or networking, you need to show up every day.

4. Burning Bridges: Your reputation is everything. Be transparent, communicate openly, and always act with integrity. Real estate is a small world, and a bad reputation can close a lot of doors.

Leveraging Title Companies for Connections

Title companies are an often-overlooked resource for wholesalers. They handle real estate transactions every day and work with a variety of buyers and sellers. Get to know a few good title companies in your area. They can connect you to other investors, provide insights into the local market, and even help you navigate tricky deals. A strong relationship with a title company can make your life as a wholesaler significantly easier.

The Long Game: Scaling from Wholesaling to Owning

Wholesaling is a fantastic way to get started, but the goal is to eventually transition into owning properties yourself. Start building a portfolio by holding onto some of the properties you come across. Use the capital you generate from wholesaling to fund down payments, renovate properties, or even buy properties outright.

I personally transitioned from wholesaling to buy-and-hold investments and have built a portfolio of rental properties over the years. Owning properties gives you long-term passive income, tax benefits, and the potential for appreciation. Once you’ve mastered wholesaling, the transition to owning properties becomes much easier because you already know how to find deals, analyze markets, and negotiate.

Final Thoughts: Staying Consistent and Adapting

Real estate investing, and wholesaling in particular, is a journey filled with ups and downs. The key is to stay consistent, keep learning, and always be ready to pivot when market conditions change. I’ve seen the market go through booms and busts, and the wholesalers who thrive are those who adapt and innovate.

Remember, the goal isn’t just to wholesale properties forever—it’s to build a real estate portfolio that provides you with financial freedom and long-term wealth. Wholesaling is just the first step, but it’s an essential one that lays the groundwork for everything that comes next.

Mastering the Art of Wholesaling: It’s All About Being the Connector

When it comes to wholesaling, remember this—you’re not the buyer, the seller, or the one bringing the money. Your role is unique because you’re the connector that makes things happen. That’s why wholesaling requires a very specific skill set and mindset. You need to have a deep understanding of human psychology, the ability to build trust quickly, and the persistence to see deals through from start to finish. This is where many new wholesalers get overwhelmed because, quite frankly, it’s a lot more work than people think.

You’re dealing with sellers who are often in distress—maybe they’re facing foreclosure, going through a divorce, or dealing with a property that’s become a burden. Your job is to approach them with empathy, understanding their situation, and showing them that you can provide a quick solution. On the flip side, you’re also dealing with investors who expect you to bring them great deals. If you don’t have a strong deal lined up, they won’t look twice. So, you’re constantly balancing the needs and expectations of both parties while making sure the numbers work for everyone involved.

Psychology and Persistence: The Backbone of Wholesaling Success

Wholesaling requires a lot more psychology than people realize. You need to be able to read people, understand their motivations, and adjust your approach accordingly. Sometimes, a seller just wants to get out of a tough situation fast; other times, they want to squeeze every last dollar out of the deal. Being able to navigate these conversations is crucial. That’s where studying and experience come in—every interaction helps you become a better communicator and negotiator.

And then there’s the persistence aspect. You’re going to have to make hundreds, if not thousands, of phone calls. You’ll be driving all over the place, searching for properties and meeting with potential sellers and buyers. You’ll hear a lot of “no’s” before you get to a “yes.” That’s just the nature of the business. But the ones who succeed are those who don’t give up. Being persistent is the most important thing, right? It’s not just about closing one deal—it’s about doing this day in and day out, no matter how many setbacks you encounter.

The Speed Game: Moving Fast and Underwriting Deals in Minutes

Speed is one of the most critical aspects of wholesaling. The moment a good property hits your radar, you need to act fast. You have to underwrite the deal quickly—assessing its potential, estimating repair costs, and figuring out if the numbers make sense for your buyers. This is where having a reliable team behind you can be a game-changer. Whether it’s an inspector who can run out to the property on a moment’s notice or a contractor who can provide a quick estimate on repair costs, having these resources in place can mean the difference between closing a deal and losing it to a faster competitor.

Having a team isn’t just a convenience; it’s a necessity. When you’re wholesaling, you need to move with the efficiency of a well-oiled machine. The minute a property becomes available, you should have someone ready to inspect it, another person ready to assess its market value, and a buyer lined up who’s already interested in that type of deal. This level of preparation and coordination is what allows you to move fast, close deals quickly, and keep everyone happy.

Being the Ultimate Problem Solver

The reality of wholesaling is that you’re constantly solving problems. Sellers might have unrealistic expectations, buyers might back out at the last minute, or unforeseen repair costs might throw your numbers off. It’s your job to keep things moving, find solutions, and ensure the deal goes through. This is why I often say that wholesaling requires the most skills compared to other forms of real estate investing. You need to be resourceful, knowledgeable, and resilient.

But it’s also a great way to build up cash reserves, especially if you don’t have much capital to start with. By connecting sellers and buyers and making deals happen, you’re building up your experience and your bank account at the same time. That’s what makes wholesaling such an attractive option for new investors or those who want to increase their capital quickly.

Establishing Trust and Credibility

When you’re just starting out, one of the biggest challenges is establishing trust and credibility. You need to show sellers that you’re serious and can get the deal done. At the same time, you need to prove to buyers that the deals you bring are worth their time and money. This takes a combination of good communication, professionalism, and transparency.

I always recommend being upfront and honest about your role in the transaction. Let the seller know you’re a wholesaler and that your goal is to get the property under contract and find an investor to purchase it. Likewise, let buyers know you’re the one finding and securing these deals for them. People appreciate honesty, and being transparent about your intentions will set you apart from others who might try to hide their role.

The Role of Marketing and Building a Strong Online Presence

Marketing plays a huge role in wholesaling. You need to get the word out there, not just about the properties you have under contract but also about yourself. Build a personal brand that showcases your expertise, reliability, and commitment to helping both sellers and buyers. Create a website, run social media ads, or start a YouTube channel to educate others about wholesaling. By providing value and educating your audience, you position yourself as an authority in the field.

You can also use your online presence to attract motivated sellers. Run ads targeting homeowners in specific zip codes, or create content that speaks to their pain points and offers solutions. This way, you’re not just waiting for deals to come to you—you’re actively generating leads and opportunities.

Final Thoughts: Embracing the Wholesaling Lifestyle

Wholesaling is not just a job; it’s a lifestyle. It’s about being out there, driving around neighborhoods, making calls, meeting people, and constantly pushing yourself to find the next deal. It requires thick skin, quick thinking, and a lot of determination. But the rewards are worth it. Not only can you build a strong financial foundation, but you also gain skills and experience that will serve you throughout your entire real estate career.

At the end of the day, remember that wholesaling is a great way to start, but it doesn’t have to be where you stop. Use it as a stepping stone to bigger opportunities, like owning rental properties, doing fix-and-flips, or becoming a private lender. Keep learning, keep growing, and never settle for just one strategy. Real estate is vast, and there’s always another level to reach.

So, stay flexible, build genuine relationships, and always be ready to act fast when opportunities arise. That’s the wholesaling game, and with the right mindset and approach, you can win big!

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Vanessa has over 23 years of business management experience and has been in the real estate industry since 2018. She and her team prioritize serving clients and finding the right financing options. Schedule a meeting with Vanessa: https://graystoneig.com/vanessa

 

 

My team and I have over 20 years of experience in real estate. We have strong relationships with wholesalers, probate lawyers, sellers, and others in Florida. I aim to align your investments with your vision and deliver exceptional results. Contact Vanessa to schedule a meeting: https://graystoneig.com/cody

 

 

Hello, I’m Marylyn Patankar, the Field Manager and New Client Ambassador at Graystone Property Management. I educate investors about our perks, onboard new landlord investors, and manage on-site operations. Schedule a meeting with me here: https://graystoneig.com/marylyn