The Win, The Why, and The Where of Wholesaling Real Estate.

Written by David Dodge  

Happy Monday, real estate hustlers! If you're diving into the world of real estate investing, wholesaling is one of the smartest, lowest-risk entry points. Today, we're breaking down Chapter 3 from The Ultimate Guide to Wholesaling Real Estate by Mike and Dave—a book we penned back in 2018-2019 (copyright 2020). Even after 5-6 years, the core principles hold strong. Markets change, but the fundamentals? Timeless.

In a recent live podcast episode with my client, we unpacked the Win, Why, and Where of wholesaling. It's all about timing, motivation, and location (or lack thereof). Let's dive in—no book-reading here, just actionable insights to get you started.

The Win: Now Is the Time to Start Wholesaling

The win? It's happening right now. There's no perfect moment to jump into real estate. Booms, busts, ups, downs—remember the classic advice: "Don't wait to buy real estate, buy real estate and wait."

As a wholesaler, you're not even buying properties outright. You're controlling them with contracts, then flipping the paperwork (or the deal) to an end buyer. Market direction? It barely matters. Buy at a discount, and you can wholesale in any condition—up markets, down markets, sideways markets. We've weathered full market cycles (1.5 to 2 in our 9+ years), including COVID, and wholesaling thrives.

Our internal motto: Keep the best, wholesale the rest. If you're new, wholesaling is nearly risk-free. No massive capital tie-up—you market, contract, and sell before closing. Time and marketing are your main risks, but the payoff? Huge chunks of cash with minimal skin in the game.

Wholesaling is primarily a marketing business. Skip the heavy startup costs of other ventures. It's the ultimate low-barrier hustle.

Listen to the Full Podcast Episode for a Deeper Dive

Want the unfiltered, live-stream energy? Listen to my full episode podcast with my client for more in-depth explanations, real-talk market stories, and insider tips straight from the trenches. 

The Why: Financial Freedom and Big Paychecks

Why wholesale? Simple: Make big checks, fast. Achieve financial freedom without tying up your own cash.

It's the "sexy" side of real estate—controlling premium properties with just contracts and flipping them for profit. No renovations, no landlording headaches (unless you choose that later).

Our "why" has evolved. We started as pure wholesalers 9 years ago, pivoted to buy-and-hold BRRRR (Buy, Rehab, Rent, Refinance, Repeat) investors 4-6 years back, but we never quit wholesaling. Why? It's our deal-finding machine. Off-market gems flow in via marketing. Wholesale the quick flips for cash, keep the portfolio builders.

Wholesaling tees you up for everything else: rentals, fix-and-flips, BRRRRs. It's low-risk entry to spot killer deals and scale.

The Where: Start in Your Backyard (But Anywhere Works)

Where to wholesale? Anywhere—but your backyard is best to begin.

Live or work in a metro area of 100-200k+ people? That's your playground. Drive to properties, meet sellers face-to-face, build rapport, and negotiate killer deals "belly-to-belly." Relationships close deals.

We love the Midwest—linear markets, fewer wild swings than coastal hotspots. Lower risk, steady wins.

But don't overthink: Virtual wholesaling is booming. Do it nationwide or globally. Folks crush deals from Israel    in St. Louis! Online tools make it possible.

Recap: Start Wholesaling Today

• The Win: Now. Skills you build last forever.
• The Why: Big paydays, deal flow, financial freedom.
• The Where: Backyard first, world second.

Ready to launch? Join the action at reiskool.com—our affordable community packed with courses (wholesaling, flipping, private money, BRRRR, landlording), live coaching calls, partnerships, and like-minded investors crushing it.