In this episode of Dealmaker Catalyst, host Jason Seward sits down with Wendy Coles — real estate investor, agent, private lender, and one of the most compelling voices in the Dealmaker community — for a deep dive into the strategies and mindset shifts that transformed her investing journey. Wendy's story is not a straight line. She entered real estate at 47 with no resume, no retirement, and no roadmap — just a closed gym business and a determination to build something lasting. For her first two years, she operated in isolation, figuring things out alone and leaving enormous opportunity on the table simply because she didn't know what she didn't know. It wasn't until she walked through the doors of her first Dealmaker event — nervous, hoping no one would notice her — that the trajectory began to shift. This episode focuses on the tactical and emotional progression that follows that first uncomfortable step: learning to network as an introvert, discovering creative financing and DSCRs, leaning into private lending, and finding a sense of purpose through humanitarian work with Share the Love. Wendy also opens up about the failure that knocked her off course — two emotionally driven property purchases that deviated from her system and set her back — and what it taught her about discipline and staying in your lane. Raw, relatable, and packed with practical takeaways, this is exactly the kind of episode that makes someone decide to finally walk through the door. What You'll Learn in This Episode Why operating in isolation costs investors years of progress — and what changes when you finally get in the right roomHow Wendy went from hiding in the back of a Dealmaker event in 2022 to speaking on the main stage just three years laterThe dangers of emotional investing and what happens when you deviate from a system that's workingWhy introverts are often the best networkers — and the one question that makes any room easier to enterHow involvement with Share the Love opened doors to mentorship, deals, and a clearer sense of purpose Timeline Highlights [0:00] – Introducing Wendy Coles and what makes her story so widely resonant [4:08] – Operating solo for two years and not knowing what she was missing [5:38] – Why Wendy entered real estate at 47 with no resume and no retirement plan [7:05] – Walking into her first Dealmaker event hoping nobody would notice her [8:13] – Imposter syndrome, negative self-talk, and feeling like she didn't belong [10:07] – The conversation with Jim Ingersoll that made her feel like she wasn't alone [13:28] – The icebreaker question that makes networking easier for introverts [15:09] – What the Dealmaker community revealed about creative financing and DSCRs [17:06] – Sitting next to Leon Johnson without knowing who he was — and what that taught her [19:00] – How Share the Love entered her life at a pivotal personal moment [20:38] – Nine humanitarian trips and the real estate education that came with them [23:28] – From back of the room in 2022 to front of the stage — the full circle moment [24:18] – What she's speaking on at the Dealmaker event: obstacles to opportunities [28:45] – Rapid fire questions begin [29:26] – Her favorite life quote: "You are the director of your life" [30:16] – The belief that kept her stuck: that success required a path she had already missed [32:22] – What she had to give up to start recognizing her own wins [34:27] – What she would not do again: intentionally going slow when the deals were there [36:21] – The failure that knocked her back: two emotional property purchases outside her system [39:23] – What the next five years look like: lending, creative finance, and buying outside the country Rapid Fire Highlights Favorite life quote: "You are the director of your life — don't play the scripts written by others."Dangerous early belief: That success required college, and since she dropped out and became a teen mom, she had already failed before she startedBiggest regret: Intentionally slowing herself down in 2019–2021 and missing deals she will never get backDefining failure: Buying a cabin and a lake house emotionally, outside her system, which overwhelmed her finances and pulled her back from investingKey mentor moments: Jim Ingersoll, Leon Johnson, Ray Ferguson, and a lending mentor who told her to borrow her belief Resources Mentioned Elite Dealmakers community discounts: https://elitedealmakers.com/discountThis episode is sponsored by 608B Capital: https://608bcapital.com/Share the Love — humanitarian organization connected to the Dealmaker communityBiggerPockets Podcast — where Wendy first learned the fundamentalsRay Ferguson — Colonial Heights real estate meetupLeon Johnson — featured in Episode 3 Connect and Subscribe If this episode sparked something for you, subscribe, leave a review, and share it with someone who's serious about building their real estate ...
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