Discover how Nathan Payne went from door-to-door salesman to pioneering a new model of ethical wholesaling. Learn why his “fail forward” approach and relentless action set him apart in a crowded market
Go inside the world of wholesaling to understand the difference between traditional, reverse, and Nathan’s “pre-flipping” strategy. See how he leverages data, buyer psychology, and transparent sales processes to turn leads into profitable deals
Get the unfiltered truth about real estate investing — from why most new wholesalers fail, to the biggest myths about “no-money-down” deals. Nathan shares what it really takes to build a sustainable business, find hidden opportunities in secondary markets, and avoid falling for industry “dream sellers”
Host: Daniel Shaked (Home365)
Guest: Nathan Payne, Real Estate Wholesaler & Coach, Founder of the “Painless Wholesaling” Method
Duration: 52 minutes
Topic: Real estate wholesaling, reverse wholesaling vs. pre-flipping, ethical deal-making, and building a sustainable investing business
Daniel Shaked: Welcome to Real Estate Investing Open Kimono by Home365. We’re discussing real estate’s biggest traps with brutal honesty. Today we’re going to supercharge your wholesaling strategy with Nathan Payne. Nathan, great to have you here.
Nathan Payne: I’m excited to chat. Glad I can be your first wholesaler on the show.
Daniel Shaked: Tell us who you are—what motivates you?
Nathan Payne: I’m 34, now in the Toronto area. My priorities are God, family, and serving others. After high school I did a two-year church mission—no TV, strict schedule, talking to people all day. That led to years of door-to-door sales in college (alarms, satellite TV, phones, pest control). I did well, but I didn’t want that forever.
Nathan Payne: After college I explored insurance and medical sales interviews but hated the process. I’d been self-directed for years and wanted to work for myself. A college roommate had done real estate, so we quit our jobs and jumped in—even though I didn’t yet know what wholesaling was.
Nathan Payne: Fun door-to-door story: knocking in rural Texas at 9 PM, a man answered with a gun. I still tried to sell him satellite TV. In hindsight… yeah, timing matters.
Nathan Payne: At first we just knocked doors and called For-Sale-By-Owners. Real traction came after networking—an agent broker gave us dialers and space: “Wholesale what you can; send me listings.” We learned fast by taking massive action.
Daniel Shaked: People avoid direct communication. Taking action is rare—and valuable.
Nathan Payne: Exactly. You have to be willing to fail forward. Many people know what to do but won’t do what’s required.
Daniel Shaked: Explain wholesaling for newcomers.
Nathan Payne: You contract to buy a property at a discount (say $100k on a home worth $250k after rehab) due to condition, tenants, timeline, etc. You then assign your contract to an investor buyer for a fee (e.g., $120k). You never need to own the asset; you can also double close when needed.
Daniel Shaked: Our clients are often remote, international, and cash buyers looking for deals. What do you offer them?
Nathan Payne: Great deals—solving problems without owning the asset. We monetize by finding and assigning opportunities.
Daniel Shaked: What’s harder—inventory or buyers?
Nathan Payne: Used to be buyers; today tech and relationships make “who’s buying” easier. The real challenge is engagement—getting decision-makers to act within 7–14 days while we control the contract.
Nathan Payne: Lead gen is easier than conversion. Every seller is different—it’s a sales process. Many think wholesalers take advantage. I do the opposite: I push sellers to their best option—list it, flip it, keep it—then only proceed with cash if that’s truly their best path.
Daniel Shaked: What’s reverse wholesaling?
Nathan Payne: Traditional = lock up deals hoping a buyer exists. That’s why many fail—locking bad deals and wasting everyone’s time. Reverse = start with a buyer’s criteria, then hunt. Better, but buyers can be picky and you may still waste leads.
Nathan Payne: My approach is pre-flipping: when a seller isn’t at my number yet, I quickly call nearby proven buyers (data: who flipped on that block), validate where they’d be, then go back to the seller with confidence. I don’t promise what I can’t deliver, and I save more leads.
Nathan Payne: Deals can close in 2 days—or 6 months—depending on the situation (probate, family approvals, urgency). Sellers rarely grant long inspections; 7–14 days max, often much shorter. So buyers have to act fast, which is why pre-flipping works: I’ve already validated demand.
Daniel Shaked: Do you have a live inventory platform?
Nathan Payne: I run a lean operation—fewer deals by design—plus I teach. There are platforms in the space, but my focus is high-quality deals and coaching.
Nathan Payne: I struggled early following the “low-ball and follow-up forever” model. Now I teach an ethical, transparent process. Ideal students have at least ~$1k/month for lead gen and are willing to learn step-by-step. We run a true apprenticeship: qualify leads first, then gradually take on closing and dispo (or partner on deals while they learn).
Nathan Payne: Misconception: you can build a sustainable business with no money. You can do a deal or two that way, but long-term you need budget, tools, and consistency. I don’t sell the “Ferrari on the beach” dream—this is hard work, like any business.
Daniel Shaked: Real estate is full of rosy spreadsheets that ignore maintenance, capex, vacancies, and delinquency.
Nathan Payne: Exactly. One bad six-month stretch—or a single AC replacement—can wipe out years of “cash flow.” You need reserves and realistic expectations.
Nathan Payne: We start with a one-on-one “life plan” (purpose and goals), choose a viable market, set up lead gen, then master qualification. From there, we add closing and dispo skills. With us, it’s not overwhelming; without support, it can be.
Nathan Payne: We can operate anywhere in the U.S. if data shows buyers exist. I’ve done deals nationwide; secondary markets often offer better returns than tier-one cities.
Nathan Payne: Real estate is hyper-local. Some markets are cautious; others are steady. As long as we find good deals, business continues—buyers adjust pricing but keep buying.
Daniel Shaked: Many investors only know “brand name” cities. How do we educate them on better-yield secondary markets?
Nathan Payne: Show the data—cap rates, growth, stability. Places like the Midwest can outperform coastal markets. When investors see the numbers, they’re open.
Daniel Shaked: Final question: what keeps you up at night?
Nathan Payne: With AI, people will struggle to distinguish truth from convincing fakes. That can mislead newcomers and waste time. Still, change is constant—every industry will be disrupted. Real estate agents may be impacted first; processes will automate, but housing will remain a core need.
Daniel Shaked: Pleasure having you, Nathan. Our investors will love this.
Nathan Payne: If you liked this, join my free Facebook group: Real Estate Wholesaling — The Painless Way. I share free courses and we help people do this business ethically. For deeper help, reach out about the apprenticeship.
Nathan Payne is a real estate wholesaler and coach who teaches an ethical, data-driven method for validating and assigning deals. His “pre-flipping” approach aligns seller expectations with real buyer demand while reducing wasted leads.
Wholesaling, reverse wholesaling, pre-flipping, real estate investing, seller conversion, ethical sales, secondary markets, data-driven underwriting, apprenticeship, AI disruption, Nathan Payne
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