EPISODE · Jun 17, 2026 · 30 MIN
50 Flips a Year and a $30K Equity Deal Out of College: Two Wisconsin Investors on Getting Started Fast
from The Wisconsin Investor · host Corey Reyment
Send us Fan MailMost people wait too long. They wait for more money, more experience, more certainty. These two didn't.Carter Crowley dropped out of UW after one year, grinded as a buyer's agent for five years, and made the call during Covid to go all in on flipping. He now does around 50 flips a year in the Fox Valley, buying most of them with just closing costs out of pocket thanks to a community bank relationship he spent years building. Carter and his dad started with a $65,000 deal financed by family, a credit card, and a lot of sweat equity. Today they're financing at 85% of after repair value through a local lender who knows and trusts them.Connor DeRenne graduated college in Milwaukee, started at Wisconsin Discount Properties two weeks later, and closed on his first investment property less than a year out of school. He bought a duplex nobody else made an offer on for $245,000. It appraised at $290,000 on day one. Thirty thousand dollars in equity just from buying right.In this compilation episode you'll hear both of them break down exactly how they got started and what they'd tell anyone sitting on the fence right now.What's covered:How Carter went from $65,000 family loan and a credit card to financing flips with just closing costs out of pocketThe community bank relationship that changed everything for Carter's business and how long it took to buildHow Connor approached his dad as a private money partner, what he showed him to overcome the fear, and how they structured the dealWhy Connor's goal went from 50 doors in seven years to 100 doors in one conversation with his dadCarter's profit per month formula and why it determines whether he does a full rehab or just cleans and relistsCarter's exact offer formula: ARV times 90%, minus rehab, minus profit marginWhat Corey learned the hard way putting a manufactured home on a Jackson County property with surprise costs that blew the budgetWhy losing on a deal isn't the problem. Never doing another one isWhat Connor told himself in the two-hour window after his offer got accepted when he almost talked himself out of itGet off-market deals every Monday at 6am: WisconsinDiscountProperties.com
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Send us Fan Mail Most people wait too long. They wait for more money, more experience, more certainty. These two didn't. Carter Crowley dropped out of UW after one year, grinded as a buyer's agent for five years, and made the call during Covid to go all in on flipping. He now does around 50 flips a year in the Fox Valley, buying most of them with just closing costs out of pocket thanks to a community bank relationship he spent years building. Carter and his dad started with a $65,000 deal fin...
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50 Flips a Year and a $30K Equity Deal Out of College: Two Wisconsin Investors on Getting Started Fast
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