In this episode of The Wisconsin Investor Podcast, Reese Brown and Connor Derenne tackle the real conversations they have every single week with Wisconsin investors. Not theory. Not guru advice. The objections and roadblocks that actually stop people from doing deals.
The episode focuses on why so many investors feel stuck, what “analysis paralysis” really looks like in practice, and how clarity around goals, buy boxes, and networking is what actually moves deals forward.
Rather than talking about market timing or perfect deals, Reese and Connor break down:
🔍 Why most investors don’t know what they’re actually looking for
⏳ How waiting for the “perfect” deal often costs more than a bad first deal
🎓 Why your first deal can be tuition, not failure
🤝 How networking quietly solves confidence, funding, and execution issues
🏦 Why Wisconsin’s local lending and investor ecosystem is a massive advantage
The core theme is simple. Progress comes from clarity and action, not more consumption.
