Zen and the Art of Real Estate Investing with Jonathan Greene

Creating a Deal Machine by Driving for Dollars with David Lecko


“Driving for dollars” has taken on a whole new meaning in the age of technology, thanks to David Lecko, the CEO of DealMachine. In this episode of Zen and the Art of Real Estate Investing, Jonathan explores how DealMachine revolutionizes property scouting for investors. Gone are the days of pen and paper; now, investors can easily locate and gather property data and owner contacts. David’s inspiration for DealMachine came from a missed investment opportunity, revealing the need for tech innovation in real estate.

In a thought-provoking chat, Jonathan and David explore the core of the “driving-for-dollars” strategy and some secrets to DealMachine’s success. They cover why meetup groups matter in real estate investing and explain that you don’t necessarily need a script when approaching property owners. Even in today’s market, when interest rates are soaring, and property prices are rising, they share why you can still create a thriving career in real estate investing. David’s thoughts on breaking free from analysis paralysis and creating your own opportunities provide a valuable perspective for both newcomers and seasoned real estate investors alike.


Some main takeaways from Jonathan and David’s conversation include:

  • There are still opportunities in real estate despite higher interest rates and prices. Many of David’s DealMachine customers are just getting started. The trick is to find like-minded individuals to be unaffected by negative thoughts from others. Investors provide solutions during moments of change, and altering your strategy can allow people who are already successful to do even more deals than ever.

  • DealMachine didn’t set out to change anyone’s behavior. Instead, it was a simple personal solution for David–until he discovered a market for this type of tech for real estate investors. Driving for dollars with an app eliminated the need for pen and paper.

  • It’s okay to respond to a property owner with, “I don’t know.” Scripts can be helpful, but you’ll often receive calls back from property owners at inconvenient places where you won’t have a script available. You can focus on a few key points during conversations with them and pay attention to what the property owner says. Be willing to meet them either in person or virtually.


David Lecko’s experience with driving for dollars offers lessons every investor can learn from that you won’t want to miss.

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