Nathan Payne is the co-founder of Offer on Homes and Investor Drive, a wholesaling investment firm and real estate coaching platform helping investors scale their portfolios the "Painless" way. With a background in door-to-door sales and a passion for autonomy, Nathan has built a thriving real estate business while living his dream lifestyle in rural Ontario. He specializes in wholesaling, flipping, and coaching clients through real-world deals using a hands-on apprenticeship model.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

Key Takeaways

• Nathan transitioned from door-to-door sales to real estate after seeking a lifestyle with more autonomy and time freedom.

• He emphasizes real-world coaching through deal partnerships, not just video courses or information dumps.

• Wholesaling success comes from embracing rejection, refining your sales process, and staying persistent through messy deals.

• Building savings and having a support system are critical when transitioning into entrepreneurship.

• Real estate investing should align with your lifestyle goals—not just financial benchmarks.

Topics

From Sales Hustler to Rural Investor

• Started in door-to-door sales before quitting to launch a real estate business with his roommate.

• Lacked marketing and deal flow at first, but invested heavily in coaching and mentorship to improve.

• After seven years in the business, he moved with his family to a farm in Ontario, living a slower, intentional life.

Lessons from the Early Grind

• Faced rejections, lost contracts, and failed deals when first starting.

• Learned that sales tactics differ between products—urgency pressure may work for cable, not for homes.

• Paid for mentorship after realizing trial-and-error was too costly and time-consuming.

Painless Flipping and Coaching Philosophy

• Teaches students by reviewing live deals, helping them qualify leads, and even partnering on closings.

• Emulates an apprenticeship model: direct feedback, ongoing support, and real deal experience.

• Rejects the passive "info-only" coaching model in favor of outcome-driven partnerships.

Living With Purpose, Not Pressure

• No longer driven by money—prioritizes time with family and coaching a handful of serious clients.

• Believes success is defined by clarity and self-awareness, not vanity metrics or hustle culture.

• Coaches students to align investing strategy with lifestyle goals from day one.

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Nathan up for success: Early in marriage, he focused too much on money and not enough on being present—this taught him to reprioritize family above all.

Digital or mobile resource: ChatGPT — a must-use tool for business efficiency and content creation.

Book recommendation: 10x Is Easier Than 2x by Dan Sullivan — a mindset-shifting read on thinking bigger while simplifying your focus.

Daily habit: Reviews OKRs (Objectives & Key Results) and life vision daily to ensure each task aligns with long-term goals.

#1 insight for wholesaling properties: Don't do it unless you're ready for an emotional roller coaster—real estate deals rarely go perfectly.

Favorite restaurant in Ontario: Gusto Grande.

Next Steps

• Explore Nathan's hands-on coaching at PaynelessFlipping.com

• Evaluate your current investing strategy: is it aligned with the lifestyle you actually want?

• Don't just seek information—find a mentor who will walk with you through your next deal.

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