Talented Investors That Share

How This 23-Year-Old Went From Painting Apartments to Managing 11 House Flips

Episode Summary

In this episode of The Talented Investors That Share Podcast, we sit down with Connor—our team’s go-to project manager who started as a 23-year-old painting apartments while listening to Rich Dad, Poor Dad. Now? He’s managed as many as 11 house flips at once. We talk about what it’s really like to scale a real estate investing business, how to go from answering phones to managing teams and systems, what to look for when hiring (and what not to do when outsourcing), and the behind-the-scenes chaos HGTV never shows you—like squatters, geothermal units, and dogs who don’t belong to you. Whether you’re thinking about your first hire, looking to get into the business, or wondering how to scale up without losing your mind, this episode is packed with actionable insights (and some hilarious stories). 🔑 Topics covered: • Taking action vs. just learning • Managing 11 rehabs at once • Hiring lessons (what we learned from a failed VA) • Why project management IS a sales job • Building SOPs and removing yourself from the chaos • Dealing with unexpected issues: squatting, snowstorms, and strange HVACs 👉 Join our community: 📘 Talented Investors That Share — Facebook Group

Episode Notes

In this episode of The Talented Investors That Share Podcast, we sit down with Connor—our team’s go-to project manager who started as a 23-year-old painting apartments while listening to Rich Dad, Poor Dad. Now? He’s managed as many as 11 house flips at once.

We talk about what it’s really like to scale a real estate investing business, how to go from answering phones to managing teams and systems, what to look for when hiring (and what not to do when outsourcing), and the behind-the-scenes chaos HGTV never shows you—like squatters, geothermal units, and dogs who don’t belong to you. 

Whether you’re thinking about your first hire, looking to get into the business, or wondering how to scale up without losing your mind, this episode is packed with actionable insights (and some hilarious stories).

🔑 Topics covered: 

• Taking action vs. just learning 

• Managing 11 rehabs at once 

• Hiring lessons (what we learned from a failed VA) 

• Why project management IS a sales job 

• Building SOPs and removing yourself from the chaos 

• Dealing with unexpected issues: squatting, snowstorms, and strange HVACs 

👉 Join our community: 📘 Talented Investors That Share — Facebook Group