Blog - DealMachine for Real Estate Investing

Beginner’s Luck? Or a Smart Wholesaling Strategy?

Written by Maria Tresvalles | Aug 19, 2025 11:30:00 AM

Getting started in real estate wholesaling can feel overwhelming. There’s a lot to learn: how to find leads, what marketing works, and how to close deals fast.

But what if you could learn from someone who’s already done it?

In this blog, we break down the journey of Chad Young, a successful wholesale real estate investor, who started from scratch. He shares the lessons he learned the hard way. From wasting money on bad data to landing his first deal with a simple text.

Whether you're just starting or want to grow faster, his story is full of real, practical advice you can use right away.

Starting in Real Estate Wholesaling: Lessons from the First Deal

Getting into real estate wholesaling is a high-reward opportunity but it's also filled with learning curves. Chad shared how he moved from early struggles to closing consistent deals by making smart shifts in strategy.

Why Data Quality Matters in Wholesaling

Like many new wholesalers, he started with energy and ambition. But his marketing efforts were built on poor-quality data.

He mailed out thousands of handwritten letters, hoping to reach motivated sellers. Unfortunately, many of the homeowners had already sold years ago.

That mistake cost time and money and left him frustrated. His key takeaway? High-quality lead lists are essential.

Without reliable data, even the best marketing won’t work.

How One Bulk Text Unlocked His First Deal

Everything changed when he partnered with another wholesaler named Jentz. They began experimenting with bulk texting for real estate leads. A tactic that was still highly effective in 2020.

One message landed with a seller who needed to move quickly due to personal reasons. That led to his first successful deal, proving that targeting the right people with the right message makes all the difference.

Want to hear the story straight from the investor himself? Watch this quick video to see how one simple text led to his first successful wholesale deal.

 

Scaling a Real Estate Wholesaling Business with Smarter Marketing

After closing his first deal, he quickly realized that scaling meant staying adaptable. He transitioned from physical mail to digital tools like:

  • Bulk texting platforms
  • Radio ads targeting local homeowners
  • Lead generation CRMs

Each marketing channel had its moment. Radio ads, for example, brought in consistent leads until rising costs and market saturation reduced their effectiveness.

The key was always knowing when to pivot.

Leadership and Team Development for Long-Term Growth

As his wholesaling business grew, so did the need for strong leadership. He invested in leadership coaching for both himself and his team to build systems and communication that supported growth.

That investment paid off. It created a healthy work environment, better deal flow, and a team that was aligned and motivated.

A Winning Philosophy: Certainty, Speed, and Convenience

In a competitive market, this investor stood out by offering what sellers want:

  • Certainty that the deal will close
  • Speed from contract to payment
  • Convenience with fewer steps and less hassle

He emphasized that while he may not always offer the highest price, sellers value reliability and a smooth transaction.

This approach has helped him build trust and grow his referral network.

Why Ethics and Reputation Matter in Wholesaling

Too many wholesalers focus only on quick profits. But this investor believes in playing the long game. By operating ethically, being honest, transparent, and consistent, he’s built a reputation that keeps bringing in deals.

He’s proof that ethical real estate wholesaling doesn’t just feel good, it also drives sustainable success.

FAQ: Real Estate Wholesaling Basics

What is real estate wholesaling, and how does it work?

Real estate wholesaling is when you put a property under contract at a low price and then assign that contract to a buyer—usually for a fee.

You don’t need to buy or fix the property yourself.

How do wholesalers find motivated sellers?

Common lead generation methods include:

Is real estate wholesaling legal and ethical?

Yes—when done properly. Always disclose your intent, use proper contracts, and be transparent with sellers. Ethical wholesalers build trust and long-term credibility.

What are the best marketing strategies for real estate wholesalers?

The most effective strategies include:

  • Bulk SMS messaging
  • Targeted radio ads
  • Facebook and Google Ads
  • Cold calling
  • Building a referral network

How much money do you need to start wholesaling?

You can start with a small budget, anywhere from $500 to $2,000. Focus your spending on good data, basic marketing tools, and learning how to close your first deal.

Conclusion

Real estate wholesaling isn’t about getting rich overnight. It’s about learning what works, building good habits, and treating people right. Chad Young didn’t find success by luck; he stayed flexible, stayed honest, and stayed focused.

If you want to succeed in wholesaling, start with solid data, use smart marketing, and always lead with trust. Follow these steps, and like Chad, you’ll be well on your way to building a real business that lasts.