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He Bet Everything on Real Estate — And It Worked

Real Estate Excellence

Release Date: 11/24/2025

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More Episodes

Would you be willing to remove an organ just to escape your 9-to-5 and chase your dream?

In this episode of the Real Estate Excellence Podcast, Tracy Hayes sits down with Drew Kazemba. Drew shares one of the most unconventional entries into real estate ever told—he voluntarily had his appendix removed to get time off work and take his real estate exam. Drew walks us through how he transitioned from a miserable medical sales job into building a thriving real estate career in Jacksonville, Florida. From cold-calling hedge funds and wholesaling to learning the ropes at DJ & Lindsey, Drew reveals the gritty hustle behind his rapid success.

He also dives into how technology like ChatGPT has supercharged his operations, the power of learning from top agents, and why real estate isn't just about selling homes but building wealth and strategic opportunities for clients. This episode is packed with golden insights for both new agents and seasoned pros looking to level up.

Are you stuck in a job you hate and dreaming of diving into real estate? Don’t wait for the perfect moment—take action now. Subscribe to the Real Estate Excellence Podcast for more inspiring stories and tactical advice. Follow and message Drew Kazemba to learn how you can build wealth through real estate—no appendix removal required.

 

Highlights:

00:00 - The Appendix Exit Plan & Real Estate Awakening

  • Drew's bold plan: appendix removal for PTO
  • Leaving medical sales for real estate
  • Self-teaching wholesaling after hours
  • Scoring a big deal that never paid, but lit the fire
  • The moment he knew real estate was it

11:59 - 22:59 Building Skills Through Volume

  • Interviewing brokerages and choosing DJ & Lindsey
  • Call time, leads, and sales floor discipline
  • Learning fast through repetition and structure
  • At-bats vs. years: why high-volume matters
  • Outgrowing a lead-based model

23:00 - 32:59 Time-Blocking, Tech, and ChatGPT Mastery

  • ChatGPT as virtual assistant and knowledge base
  • Automating follow-ups with Zapier
  • Using AI to build reports and analyze tax strategies
  • Structuring days with time blocks
  • Why tech-savvy agents have the edge

33:00 - 46:28 From Agent to Developer

  • Meeting Matt Roberts again and joining Someday
  • Learning construction, development, and investment modeling
  • Using project experience to serve investor clients
  • Helping buyers buy smart with long-term mindset
  • Real estate as a launchpad to bigger things

46:29 - 1:00:00 Equity, Cash Flow, and Pitfalls

  • The myth of guaranteed cash flow
  • Evaluating properties like a pro
  • Why break-even deals still build wealth
  • Common investor mistakes and bad flips
  • How Drew calculates cost of money, rehab, and ROI

1:00:01 - 1:16:11 Airbnb Realities & Final Real Estate Lessons

  • Is Airbnb still worth it in NE Florida?
  • Short-term rental logistics and costs
  • How Drew advises on STR vs long-term play
  • Risk management and truth-telling for investors
  • Empowering buyers with education and honesty

 

Quotes:

“I got my appendix removed just to take time off and chase real estate—I'm not kidding.”

“You win in real estate when you buy the house, not when you sell it.”

“You’re not going to cry about the deal you didn’t get; you’re going to cry about the one you lost money on.”

“ChatGPT is my best friend. I vent to it, I time-block with it, and I learn from it.” – Drew Kazemba

 

To contact Drew Kazemba, learn more about his business, and make him a part of your network, make sure to follow him on his Website, Instagram, Facebook, YouTube, and TikTok.

 

Connect with Drew Kazemba!

Website: https://www.somedayhomesteam.com/
Instagram:
https://www.instagram.com/drewkaz_jaxrealtor/

Facebook: https://www.facebook.com/drew.kazemba/

YouTube: https://www.youtube.com/@DrewKRealty

TikTok: https://www.tiktok.com/@dkazemba

 

Connect with me!
Website:
toprealtorjacksonville.com  

Website: toprealtorstaugustine.com 

 

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