EPISODE · Jul 9, 2026 · 37 MIN
Flipping vs Rentals, Seller Psychology, and Six Figure Deals: Two Wisconsin Investors on Getting It Right
from The Wisconsin Investor · host Corey Reyment
Send us Fan MailMost new investors try to do everything at once. Flips, rentals, networking, analysis, all while keeping a W2. Colin and Jenny both learned the hard way that focus is what separates the investors who close deals from the ones who stay busy without getting anywhere.Colin grew up managing flips with his dad in Milwaukee since he was six years old, spent three years in UW Madison's number one ranked real estate program in the country, and has been working acquisitions and asset management on flips since high school. Jenny Buell accidentally became a landlord in 2012 when she couldn't sell an underwater condo in Madison, moved to northeast Wisconsin, chickened out for a few years, and came back in 2018 to build a portfolio that includes a single flip that netted her over six figures.What's covered:How Colin learned to evaluate rehab costs just by spending time at Home Depot, and why that knowledge protects you from contractors who take advantage of investors who don't know their numbersWhy flipping and holding rentals are two completely different businesses and why trying to run both at the same time while keeping a W2 almost guarantees you get average results in bothHow Jenny went from a Craigslist rental and a downloaded lease to pulling six figures on a single flip in Green Bay's Indian Trails neighborhoodThe seller psychology lesson Corey uses on every appointment: price is never actually the most important thing, and the flip phone analogy that makes it clickWhy Jenny set up her HELOC before she had a single property under contract and how that preparation let her move fast when the right deal showed upHow Jenny raises private money through relationships built over years of showing up to the same rooms and doing what she said she was going to doColin's zero deal summer: what happened when he tried to do acquisitions, networking, and analysis all at once and why he would do it completely differently nowHow Jenny structured a rent-back arrangement with a 70-year-old seller who was still living in the property, and what that deal taught her about solving problems for sellers instead of just throwing a number at themGet off-market deals every Monday at 6am: WisconsinDiscountProperties.com
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Send us Fan Mail Most new investors try to do everything at once. Flips, rentals, networking, analysis, all while keeping a W2. Colin and Jenny both learned the hard way that focus is what separates the investors who close deals from the ones who stay busy without getting anywhere. Colin grew up managing flips with his dad in Milwaukee since he was six years old, spent three years in UW Madison's number one ranked real estate program in the country, and has been working acquisitions and asset...
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Flipping vs Rentals, Seller Psychology, and Six Figure Deals: Two Wisconsin Investors on Getting It Right
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