From Online Poker to 250 Real Estate Deals ft Chip Ferguson EP 33 episode artwork

EPISODE · Aug 18, 2026 · 1H 4M

From Online Poker to 250 Real Estate Deals ft Chip Ferguson EP 33

from Real Talk with REsimpli Podcast · host Sharad Mehta

In this episode of Real Talk with REsimpli, Chenay Jordan and Don Carlson sit down with Chip Ferguson, owner of Smooth Closing, to unpack how nearly a decade as a high-volume online poker player shaped the way he thinks about probability, emotional control, risk, data, and decision-making in real estate. Chip shares how he went from doing virtually everything himself to building an 11-person operation that has closed around 250 deals since the beginning of 2023. In this episode, we get into: - How poker taught Chip to stay calm when outcomes don’t go his way - The mistakes he made on his first real estate investment - Why he waited nine years before making his first hire - How hitting the same 36-deal ceiling two years in a row forced him to change - Why your first hire should depend on what you’re actually bad at - Building trust and negotiating with motivated sellers - When Chip chooses to wholesale vs. wholetail a property - How his team tackles complicated title and ownership problems other investors may walk away from - Why he relies heavily on data instead of trying to predict the housing market - The new-build deal that taught him a painful lesson about market predictions - Why doing what you’re best at can be a bigger advantage than chasing every real estate strategy - The mindset behind Chip’s 8+ year streak of working out every single day REsimpli is an intuitive, all-in-one real estate software built for real estate investors that require little to no customization, so you can have your CRM up and running in minutes. REsimpli empowers your business with real-time data, allowing you to close on more deals while worrying less. Benefit from Calling, Texting, List Stacking, Driving 4 Dollars, and more all built within REsimpli. Get 50% off your first month. Sign up here - https://bit.ly/4ef8ddJ Join our free Mastermind for Real Estate Wholesalers: https://www.facebook.com/groups/wholesalersmastermind/ Try out REsimpli free for the first 14 days and see if you like it!  https://resimpli.com/action-yt/ Connect with like-minded investors and wholesalers across the US through our Facebook group and weekly calls for FREE: https://resimpli.com/join-mastermind/ Connect with REsimpli- fb- https://www.facebook.com/REsimpli/ ig- https://www.instagram.com/resimpli in- https://www.linkedin.com/company/resimpli tt- https://www.tiktok.com/@resimpli_official yt- https://www.youtube.com/@REsimpli Connect with Chip: Instagram: https://www.instagram.com/thechipferguson/ Facebook: https://www.facebook.com/TheChipFerguson

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From Online Poker to 250 Real Estate Deals ft Chip Ferguson EP 33

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This episode was published on August 18, 2026.

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