DiscussionInsightful

How Great Closers Build Trust Fast w/ Katie Desmarais

The REtipster Podcast | Land Investing & Real Estate StrategiesJuly 21, 20261h 5m

Katie Desmarais discusses how she scaled her land investing business by removing herself from daily operations through team development, delegation, and an EOS-based pod structure. She emphasizes that effective sales coaching centers on trust and authority rather than likability, and shares her philosophy on building coachable teams that embrace mistakes as learning opportunities.

Summary

Katie Desmarais returns to the REtipster podcast to dive deeper into sales, leadership, and coaching—areas she has become known for in the land investing community. Since her previous appearance over a year ago, Katie has made significant progress toward her goal of becoming irrelevant in her own business while maintaining profitability. Rather than installing a single leader beneath her, she implemented an EOS-based model with pod calls organized by business area (marketing, sales, etc.), where each team member becomes a leader and expert in their own role. This approach requires extensive training, coaching, and development hours but has allowed her to step back from daily sales calls and damage control.

Katie addresses how she leads her team through mistakes and growth. She acknowledges that employees often fear making mistakes when given more responsibility, so her first step is to make clear that failure is acceptable during the learning process. She provides an example of hiring someone strong at cold calling and recognizing her potential to grow into a lead manager role. Rather than just promoting her, Katie presented it as an opportunity with clear expectations: mistakes are acceptable, but she shouldn't see patterns of repeated errors. Katie notes she has achieved a 0% employee-chosen exit rate on her team in nearly three years, which she credits to flexibility, support, and clear communication during onboarding.

Regarding her current time allocation, Katie spends approximately 50-50 between her land business and external coaching work. However, there is significant overlap since the topics she coaches externally often mirror what she's optimizing internally. Her primary focus remains on people, processes, systems, and sales. When working with individual operators, Katie has found that most identify themselves as the bottleneck in their business due to time constraints and oscillating focus between marketing, sales, and disposition. She believes the solution lies in running all three channels simultaneously at full capacity while scaling people and systems appropriately.

On the topic of sales coaching, Katie explains that "saying the right words in the right order enough times" doesn't mean following rigid scripts. Instead, it involves tweaking individual words or phrases, using precise questioning to identify objections, and anchoring sellers to their bottom-line prices. She works with clients through various methods including biweekly team role-play calls where people practice scenarios live with group feedback, and individual call reviews where she listens to recorded calls with the operator present. Katie notes that people often default to what's comfortable rather than what's effective, and coaching involves helping them recognize these patterns.

On building rapport, Katie clarifies that she doesn't believe you need sellers to like you—instead, they need to trust you and feel confident you'll get the deal across the finish line. This sometimes means delivering hard truths. Ajay adds that modern rapport-building in 2026 is different from the sleazy sales tactics of decades past; it now centers on trust and authority. He explains that authority comes from asking educated questions that demonstrate property knowledge and experience, which automatically builds trust. Examples include asking about specific road surface materials you've already researched rather than basic questions like "does it have road access?"

Katie discusses property improvements her team typically makes, including PERC tests, surveys, wetland delineations, driveway permits, clearings, and subdivisions—all done with the goal of creating a clear vision for the next buyer and ensuring the invested capital is recouped financially or through time savings. She notes they disposition through agents 99% of the time.

Katie explains her philosophy on list filtering: while she appreciates modern tools for targeting, over-filtering has created a false sense of complexity in sellers' minds. She prefers working with less-filtered lists because it provides opportunities to solution problems and use property defects as negotiating factors. However, she's realistic that you can't force unmotivated sellers to sell on a first call—instead, you build motivation over time through follow-up, questioning, and painting a picture of reality.

Ajay discusses what made Katie coachable, explaining that he prefers working with people he knows will succeed regardless of his input, which accelerates their trajectory. He also notes an observation that women tend to have higher natural empathy and emotional intelligence, making them strong listeners, while men sometimes focus more on outcomes or saying the right thing. However, he emphasizes this is a trend, not a rule. Katie's greatest strength was her lack of ego and willingness to take feedback on recorded calls without defensiveness, implementing changes and improving rapidly.

Katie shares that she and Brian have intentionally worked with five different coaches over their first three years, each targeting specific business evolution phases. They budget for continuous development because the business iterates quickly, and stagnation equals decline. She credits her confidence and teachability to prior experience making her comfortable with transferability—if she made her corporate team members make 100 dials in their first hour, she could certainly learn land investing.

Ajay highlights a success story with another operator who went from zero experience to quitting his W-2 and building a team in nine months by actively listening, building confidence, developing empathy, and putting in consistent time. He also praises Shelby Wendgreen, who despite limited hours and no sales background, improved dramatically in six months through Land Closers Academy, eventually handling nine transactions in one month while working only 3-4 hours daily.

The conversation emphasizes that success in land investing depends heavily on sales skills, team leadership, and coachability rather than just marketing and pricing. Katie and Ajay stress that gold lies in existing pipelines—every lead represents potential profit that isn't being captured due to poor sales conversations or leadership gaps.

About this episode

277: Most land investors think success comes from pricing, data, and marketing<a href="https://retipster.com/277-katie-desmarais/?utm_source=shownotes&utm_medium=buzzsprout&utm_campaign=podcast&utm_content=277" rel="noopener noreferrer" target="_blank">(Show Notes: REtipster.com/277)</a>But after talking with Katie Desmarais, it’s clear that sales conversations, leadership, and team development are what separate struggling operators from scalable land investing businesses.In this episode, Katie breaks down how she transitioned out of the day-to-day grind, trained her team to operate independently, and improved land deal conversions through better communication and sales systems.We also talk about:<ul><li>Why most land investors become the bottleneck</li><li>How to build trust with sellers</li><li>The right words that move deals forward</li><li>Coaching, accountability, and leadership</li><li>Why overfiltering leads can hurt your business</li><li>How to create a land business that supports your lifestyle</li></ul>If you’re building a land investing business and want better systems, stronger sales skills, and more consistent deal flow, this episode is packed with practical insights.<a href="https://cPGY504.na1.hs-sales-engage.com/Ctc/2L+23284/cPGY504/JkM2-6qcW6N1vHY6lZ3mvW7wFR8r4QgzSXV5LTpf1wwRJnVXXr-K4W-brPW3hjcRT75xc_NW1tXcGT8h8qTXW7d_HRy8t8SkWW2J0Nk22Rkl5xW2G4d_12DFvRbW3SN5tH4Mk10rW3wF1M027vY3lW6ZSxtm3ZVrb6W1g_XxS4nSbp2W6dZSVC4hKpwtW5Zfyt_3tJRqPW1wBbgq2_Dn10W1M7Dc61Yzfv1W2-xBGf3GlTqPVj9GcM4KVwWrW72PD_S74FM_NW7WWc1Z9kFs8TW1vTb_y3H9kyXW5D2nsD5_pzQtf9b6lXl04" target="_blank">📊 Manage Land Deals Like a Pro with Stride CRM</a> Built for Land Investors! Organize leads, track deals, and close faster<a href="https://cPGY504.na1.hs-sales-engage.com/Ctc/2L+23284/cPGY504/JkM2-6qcW6N1vHY6lZ3kLW80mfqq6VyDR1W5zVbmd93yP65W2DV4SX6WcB-3W15Jkkz8zbNm4N9dgl0Wcyd38W48klqV1CB8k4W5xTpyY4lP1qZW2q8ps16z4ms2W2S11nP8D0gMLW3MpJ2q9jRrmSW2XJysB6XJlDnW5C236w3hcWTHW5SpnmP69NJrvW8j7T0t51qms-N8LbVbvrhb7ZN1q0kxWfC9VSW1CqQgV4yKnjgW81QzWq73G65NW1HSfn12qBWVZW5DCDMN6FDWkSW5j-pmq6rVjdDW4sMynm82b1XKf6_xczW04" target="_blank">🔎 Land Portal: The Data Edge Every Land Investor Needs</a> Get the Data You Need to Find Deals & Make Smarter Land Buys<a href="https://cPGY504.na1.hs-sales-engage.com/Ctc/2L+23284/cPGY504/Jll3gNv7W7Y8-PT6lZ3myW6kgGQ283T99dW9f15kp4X_dwgW3333g714N0bhW39B7p65kCvrRW2Y_tG682HM7-W8Gvr_y6Yv22rW52LqfQ8w7TJKW5Q6Ky_4t9ThNW4QGCVs8gLpfzW3yq3gt50BNbfW2WHhbx71f7r2W7X_2zK6G3XgDN7vH_PRzB24LW1JNKp713pDmsN1xpdm7TtqHrW5Hd9JK3xNzXXW6_dqpm7cST45W6X6_4V6fm012W1TzVhJ3tXRH6W589p801pLLdjW3KJWr168FBjpW9lKngx6gMRfgW8pzm3Z4s-2T0W4_grbk8xhsHwV7cWv_7GPpXLN8MR8jHnhDsFf4fQ9-R04" target="_blank">🙋🏻‍♂️ Get the REtipster Newsletter (It's FREE)!</a> Stay updated with top real estate investing insights and strategies<a href="https://cPGY504.na1.hs-sales-engage.com/Ctc/2L+23284/cPGY504/JlF3gNv7W8wLKSR6lZ3k-W97xTvm3M8sD_W6hmVmc64CyFGW5Gn3yK5qlPbfW4SGtw349gZDsW2Gtjnx1wJWYzN2wwvXgb1cTNW23Z1Jg6CmG70W6cTLmp1d8qGcW6sdzpm7dxgjpW44Bpbb5V52QWW365Mdl6pymYGW3W7fwg5sV2HGV5vtqY3qmf2FW66yK-18sktsfW58K8196VvKwcW4rKqlQ7m1Fs3N79RTlDDbKZZN8z6NY0kTbfcW18xgBw50c0nzW8PfGh51J625MW4Jr4p_5t9zspW4QxFmR5Zw5VrW2c5qgC8sJJG5W5gvmRd4PN2snW3YvBQP5LhkfcW3JHcRc4Dmqw5W3dxCqM9dM1Z6W1XtQpV53fYpjf2Rmwyg04" target="_blank">🚀 Land Investor’s Action Plan (Free 5-Day Course!)</a> Solve the 5 mistakes that keep investors stuck<a href="https://cPGY504.na1.hs-sales-engage.com/Ctc/2L+23284/cPGY504/Jll3gNv7W7Y8-PT6lZ3p4W30wWZB51m00rW4VK_n729M37yW7g5GDq6GnqBxN7lg964lcz3SW5fK5Wb7jfdKvVCqYHx6kNS0-W1LQCMH8RknNdW304Pmm7xlFRdVMNfKJ4zK7K8Vnwrtf7bxZFxW2sSjGH6phg3SVwD9Bb5sz31QW3RFf2D1l5sbJW3_Lsfl8Qbg1kW1RC19h2x896nW4g_CKg98jgdtW5tpJ4M3rcW4QW21LXT13WPQ44N6h4SHFgc9kDW5ssLg88ZvRYbW7lhG7J6SJ76DW4LqK0q3mQxD3VXhg4d8gfvhtW2Dgc4D78ZYKzW328syP7t-wDnW344CVw3FDNhKf4V0S9q04" target="_blank">⚠️ Land Buyer’s Survival Guide (Free 5-Day Course!)</a> Avoid the 21 most deadly land-buying blunders<a href="https://cPGY504.na1.hs-sales-engage.com/Ctc/2L+23284/cPGY504/Jll3gNv7W7Y8-PT6lZ3n0VXCDjl1bj778W3zGR0r3281zRVfHR-X22rkQhVpLtCy5ccDLKN1p4fs3tyVgVW2dmFX_7qM4pKW5Hd6zc77X_YSW6mrVTZ64G4_lW4PlWf-23_L3lW5CJ-Kc3SSrPVW7_kLrC3zNrRBW1lgZK72VNRmXN4Csd4RsKZwXW2QDTTz30Jdb2W4WZFh033g8fGN50T3qMHQVB-W1gDrJS7qywJ9W3YdMC634r6QXVYm0zF34pg7FN7pPSklcktkPN4QmDPK4MV1kW7SVkxF4-_P3tW3BJm9D5B1BDwN4vvYr9PcmpLW8pvtD78CrQjwW94ZqKw8b1Qxhf3nHcJK04" target="_blank">👉 10X Your Income from Land Investing</a> Learn how to start and supercharge your land investing business<a href="https://cPGY504.na1.hs-sales-engage.com/Ctc/2L+23284/cPGY504/Jl23gNv7W7lCdLW6lZ3nxW1pJrZT25DfcCN3ddkl7QBk9rW5bXJBk2HJk4pW20QgNw7QD6KgW3KZmm43mMd2CW7qFmdN2m-x0JW3Ftp_p7YQKC-W65Hmg23g2_8MW1cnWGG68-hwsW7n1BX-3hC5hnW4M8WdT6pk6YgW771s8Y156-yCW5lJ6mb7N95LSW4xlVcZ7kpZ_bW2-FKV93lLq3kW3qdcBB7jkjmNN1jTfdFWd58yN2d4jD6PWJ9pW8TD5L32DZHyLW4lgqrD25F_JWV-KSD07tHdgRW6HFpxY45Kk6-W5r1VXP6VFbbYW32LBlW1MNQDrf3Llgnj04" target="_blank">😀 Join the REtipster Forum!</a> Connect with experienced investors and get expert advice.<a href="https://cPGY504.na1.hs-sales-engage.com/Ctc/2L+23284/cPGY504/Jll3gNv7W7Y8-PT6lZ3mdW6jkVP68DgcgcW7wgdW191GLtDW6Fysmk3JzhsKW51mVl53NY94FW1TdfzB4tmX5dW5dlsqR8WnNRNW71Pcr-7XX0zNW4VTSV91pHdZPW82XPDP7qcyVfW1kfv-54zXhZjW24DLzj4Y7l5ZW1yZ8tv32470cW5WbKBq8GcB2jW46rbGX8TVHcJW1_tQYN3C1pfJW3J9L1T4Sd0dmW1gCvWM5bG44xW1gWfvw5ZrtjXN41Ch_pb3r0BW8dKcr66yZ1xqW1yyqqH5-6mDLW7500557S_rsGW7MXFYL2bHGmMW8FRDp21KRHP1W7ZQq9Z8f5MP3W7pTLlG6M9BdHf8vFPwq04" target="_blank">🛠️ All My Favorite Tools and Resources 🛠️</a> The best software, services, and gear I use dailySee Privacy Policy at <a href="https://art19.com/privacy" rel="noopener noreferrer" target="_blank">https://art19.com/privacy</a> and California Privacy Notice at <a href="https://art19.com/privacy#do-not-sell-my-info" rel="noopener noreferrer" target="_blank">https://art19.com/privacy#do-not-sell-my-info</a>.

Key Insights

Katie made herself less relevant in her business by up-leveling her entire team to be leaders in their own roles rather than substituting herself with a single successor, using an EOS-based pod structure where each person leads their functional area.
Katie achieved a 0% employee-chosen exit rate in nearly three years by explicitly telling employees that mistakes are acceptable during the learning phase, but she expects not to see patterns of repeated errors.
Katie spends approximately 50-50 of her time split between her land business operations and external coaching work, with significant overlap because the topics she coaches externally mirror her internal optimization efforts.
Katie identified that most struggling operators believe they are the bottleneck in their business because they oscillate focus between marketing, sales, and disposition rather than running all three channels simultaneously at full capacity.
'Saying the right words in the right order' does not mean rigid scripting but rather precise tweaking of individual words, asking educated questions, and anchoring sellers to their bottom-line prices through specific negotiation techniques.
Katie does not prioritize sellers liking her; instead, she focuses on building trust and confidence so sellers believe she will get deals across the finish line, even when delivering difficult truths.
Ajay argues that modern rapport-building relies on demonstrating trust and authority through educated questions that show property knowledge, such as asking about specific road materials rather than generic access questions.
Katie deliberately avoids over-filtering lists because filtered lists create false complexity in sellers' minds, whereas working with more leads provides opportunities to solution problems and use property defects as negotiating leverage.
Katie explained that she cannot force unmotivated sellers to sell in a first call, but rather builds their motivation over time through follow-up cadence, questioning patterns, and helping them see a realistic picture of their situation.
Ajay observed that female operators he coaches tend to demonstrate higher natural empathy and emotional intelligence for reading rooms and people, while male operators he trains sometimes focus more heavily on outcomes or saying precisely correct things.
Katie credits her rapid improvement in sales (moving from 2-3 deals monthly to six-figure months) to her lack of ego when receiving feedback on recorded calls, allowing her to implement changes and iterate quickly without defensiveness.
Katie and Brian deliberately engaged five different coaches over their first three years, each addressing specific business evolution phases, and they maintain an ongoing budget for continuous development based on the belief that iterating business practices prevents stagnation.

Topics

Building a scalable business through team delegationEOS model and pod-based organizational structureSales coaching and call reviewsBuilding trust and authority in sales conversationsLeadership philosophy and handling employee mistakesRapport building in modern sales contextProperty improvements and value-add strategiesCoaching different operator profiles based on experience levelList filtering and lead quality versus quantityCoachability and personal development as success factors

Transcript

Hey everybody, how's it going? This is Seth Williams and Ajay Sharma. You're listening to the REtipster podcast. That's right, Ajay is back in the co-host chair today because we're talking with Katie Damaris. So Katie has actually been on the show before with her husband, Brian. That was back in episode 241, where we talked about how they built and scaled their land business, how they structured their team, how they made the transition into full-time land investing surprisingly fast. Today, we're going deeper into something Katie has become especially known for in the land investing world. That is sales, leadership, and coaching. And a lot of investors think their business is mostly about pricing and data and mail…

Full transcript available for MurmurCast members

View original source →

More from The REtipster Podcast | Land Investing & Real Estate Strategies

Get AI summaries like this delivered to your inbox daily