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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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From college dropout to running 50 flips a year—Carter Crowley’s real estate journey proves what’s possible when you master your numbers, build strong relationships, and take consistent action.
In this episode of The Wisconsin Investor Podcast, Carter reveals how he went from traditional agent to full-time investor and the exact strategies that fueled his rapid growth.
What you’ll learn in this episode:
- How Carter funded his first flip in 2018 using a $65,000 family loan and $32,000 personal funds
- Why he evaluates deals on profit-per-month instead of total profit
- His simple deal formula: ARV × 90% – 10% (holding + commissions) – rehab – profit = max purchase price
- The crucial lesson: build banking relationships before you need them
- How mentorship programs like Fortune Builders & CCF accelerated his success
- Why focusing on consistent, smaller wins beats chasing $50k profits every time
Carter’s story shows that flipping isn’t about luck—it’s about systems, speed, and strong connections.
Chapters
1. Welcome to Wisconsin Investor Podcast (00:00:00)
2. Carter's Journey into Real Estate (00:03:05)
3. Financing Your First Flip (00:11:20)
4. Learning from Mistakes in Real Estate (00:19:32)
5. Evaluating Deals and Cash Flow (00:28:02)
6. Profit Per Month Strategy (00:36:12)
7. Mentorship and Wisconsin Favorites (00:48:20)
63 episodes
