Common Sales Misconceptions & Objection Handling (Podcast Ep#140)

What if the best sales training didn’t come from a textbook — but from a Miami bar?In this episode, Jessey chats with Jen Way, a real estate investor turned sales coach, who’s helped countless land investors close more deals by simply learning how to talk again. From her days behind the bar to flipping houses and buying land, Jen shares how conversation — not persuasion — is the foundation of great sales.You’ll hear Jen’s journey from marine science grad to multi-faceted investor, and why she believes anyone can become good at sales with the right mindset and structure. No gimmicks. No pressure tactics. Just real rapport, real listening, and a whole lot of curiosity.In this episode:How Jen went from wholesaling houses to coaching investors on salesWhy “likability” isn’t about personality — and what to lean on insteadJen’s repeat-relate-resume method to unlock better conversationsHow to front-load objections before they kill your deal

Some investors go big to win big — but Hunter built a thriving land business by doing the opposite.In this episode, Jessey sits down with Hunter to break down how he flips smaller, rural parcels at scale for outsized returns. You’ll hear how a college side hustle turned into a full-time business, why he avoids blind offers, and how he’s built passive income by offering seller financing to buyers who weren’t even looking.With just two VAs and a tight system, Hunter is moving 100+ deals a year — using creative direct mail, a smooth checkout experience, and 27 marketing channels to keep his pipeline full.In this episode:How flipping low-cost rural parcels led to 100+ deals a yearCreative seller financing that converts casual browsers into buyersDirect mail strategies that stand out — without using blind offers

What if your land offers weren’t just educated guesses—but backed by data, strategy, and AI?In this episode, Chris and Aaron share the pricing method behind their $500K+ land business. From using county-assessed values to anchor offers, to building consistency through neutral letter campaigns, their approach blends personal touch with data-driven systems.They also reveal how they use AI-powered tools to compare comps, assess markets, and avoid the spray-and-pray mailing method—resulting in smarter offers and higher ROI.In this episode:- Combine AI with comps for better offer accuracy- Target the right markets without guessing- Structure mail and follow-up for consistent deals- Build a lean land business without cold callingShownotes:[www.ailanddealz.com](https://www.google.com/url?q=http://www.ailanddealz.com&sa=D&source=calendar&ust=1745090899026499&usg=AOvVaw1KWDrpy-g-KQeCkjllPOFN)[[email protected]](mailto:[email protected])

Kay Walker didn’t scale with a massive team or high-volume cold calling. Instead, she built a lean, local operation that closes high-value land deals using direct mail, in-house systems, and trusted people she already knows.In this episode, Kay shares how she keeps her operations tight but effective, relying on local relationships across NC, SC, and GA, and a close-knit team that understands her process.From managing mail campaigns in-house to coordinating with realtors, soil testers, and contractors she’s worked with for years, Kay shows that smaller teams can move fast, stay personal, and win big.IN THIS EPISODE:Why local relationships make the differenceHow a smaller team keeps things efficient and profitableRunning direct mail campaigns in-houseLessons from scaling a busy short-term rental businessWhat developers really want when buying landHow to build a high-trust, low-chaos team

Ann and Mary Danielson run a land business from two sides of the world one in Denver, the other in the Philippines.No team. No VAs. No mailing in nearly a year.Yet their business hasn’t slowed down—it’s gotten more focused, more profitable, and more intentional.In this episode, they share how clearly defined roles, trusted local partners, and a well-timed seasonal rhythm have helped them scale from simple flips to complex subdivides—without burning out or chasing every deal.IN THIS EPISODE:How to stay consistent without hiring or outsourcingWhat async operations look like in a real land businessWhy focusing on fewer counties led to more deal flowHow they prepped and bought $1M in land in just 3 weeks

Daniel Seavers was brought on to handle cold calls. But very quickly, it became clear he could do more. A lot more.In this episode, Daniel shares how his role evolved into managing the full acquisitions process within a land investing business. From generating leads to making offers, following up, and closing deals, Daniel breaks down the systems and mindset that help him consistently land one deal a week.He also talks about the advantages of keeping this work in-house, how his sales background shaped his approach, and what to look for when bringing someone into this kind of role.IN THIS EPISODE:How a cold calling role became full-cycle acquisitionsWhat the day-to-day looks like when one person owns the seller pipelineThe tools and workflows that support consistent deal flowWhy follow-up and live contract signing matterWhat to consider when hiring for this role internally

From burning out in finance to crushing it in land, Ryan Becker learned something surprising—putting service before sales actually makes you more successful.After climbing the ranks as a top 2% Zillow agent, Ryan brought his “service-to-sales” mindset into the land world, using transparency and honesty as his secret weapons.In this episode, Ryan shares how leading with the bad news, focusing on what customers actually need, and documenting everything can help you build a thriving business (and sleep better at night). His approach to team management and operations is inspired by Richard Branson’s business philosophy—but packed with practical takeaways for land investors.IN THIS EPISODE:How the “service-to-sales” approach makes land deals easier to closeWhy transparency builds trust (and helps you win 99% of the time)How documenting processes makes scaling smootherThe surprising upside of putting bad news first in your marketing

How many cold calls does it take to get a lead? What about texts?Nicholas Nick, founder of Lead Mining Pros, does the heavy lifting for investors, handling the entire lead generation process from list pulling to skip tracing to handing off leads that are primed to closed.After 8 years in business, he’s turned the art of cold outreach into a science and walks us through the process step-by-step.He’s even put together a library of 7 free courses, including “Hour a Day Investor” which includes the exact scripts you need to turn leads into closed deals.His white-glove lead gen service specializes in cold calling and texting, ensuring you get high-quality leads without spending hours on the phone.Learn how many cold calls or texts it takes to generate lead with Lead Mining ProsThe difference in lead quality and quantity when it comes to cold calling vs textingThe importance of American vs foreign callers depending on the market you’re working inUnderstand the new one-to-one consent rule

Land investing has changed – deals take longer, competition is fiercer and the investors who thrive are the ones who adapt.Our guest, Logan Swanson, has spent years building a land business that stands the test of time and his biggest lesson?Focus.Not that he was!Logan dabbled in countless areas in land (and outside of land, he’s opening a coffee shop in Dallas!) but after 7+ years, his advice for new investors is to be hyper-focused.In this episode, he explains why a strong brand and niche expertise are essential for long-term success in land.We dive into how to create a business that compounds value, attracts the right deals and builds an audience that sustains growth.IN THIS EPISODE: Why branding builds authority and attracts deals How to transition from generalist to expert in land investing Why being hyper-focused is the key to long-term land investing success

Is land investing still a great opportunity in 2025? Absolutely – but the game has changed.Deals are taking longer, competition is fiercer and investors face a choice: get out or get better.In this episode, we sit down with Clay Hepler, a top-tier land investor who’s doubling down on the latter, building a high-quality, scalable business.Instead of chasing volume, he’s focusing on fewer, larger deals while structuring his team and capital for long-term growth.Clay breaks down the process of transitioning from a high-volume model to a quality-focused operation – fewer deals, bigger profits and the team required to support it. He walks us through the decision-making process, the marketing shifts required and the capital strategies that make it all possible.If you're looking to grow past the 7-figure mark, this episode is packed with insights on mindset, systematizing acquisitions, understanding key metrics and leveraging capital partnerships to scale smartly.IN THIS EPISODE:Understand the critical decision at $1M: are you going to be a high volume or high-quality shop?Find out the key numbers every land investormust track to scaleGet tips on how to sustainably transition your business and the mindset to adopt