In this episode of the Generations of Wealth Podcast, Derek sits down with real estate investor and tech entrepreneur Jason Macht to break down how AI, data, and automation are transforming the way investors find and close deals.
Jason shares his journey from engineering and fintech into real estate, where he now helps investors leverage direct mail, segmentation, and AI tools to improve marketing performance and scale their businesses.
This episode blends real estate fundamentals with cutting-edge technology, showing how even non-tech investors can start using AI to create efficiency and increase deal flow.
Watch the episode here
Listen to the podcast here
Overview
Jason Macht began his career in engineering and product management, helping build large-scale financial systems — including direct mail campaigns sending millions of pieces per month.
After transitioning into real estate, he applied that same data-driven mindset to investing, focusing on scaling through multifamily properties and eventually building systems to support other investors.
The conversation dives into:
- Why scaling in multifamily units made more sense than single-family investing
- How Jason built and managed a portfolio across states using systems and virtual support
- The fundamentals of direct mail marketing and realistic response rates
- Why most investors struggle with marketing due to poor targeting
A major focus of the episode is AI and automation, including:
- Using AI to improve marketing content and targeting
- Automating lead intake, follow-up, and qualification
- Leveraging AI for call analysis, CRM updates, and sales insights
- Reducing missed opportunities by capturing leads 24/7
Jason emphasizes that AI is not a magic solution — but a tool that enhances execution and efficiency when used correctly.
The episode closes with a powerful reminder:
👉 You don’t need to be technical — you just need to be curious and willing to experiment.
Key Takeaways
- Data-driven marketing outperforms “shotgun” approaches
- Direct mail still works — but targeting is everything
- AI is a tool, not a replacement for strategy
- Automation reduces missed leads and increases conversions
- Most businesses lose deals due to slow response time
- You don’t need to be technical to use AI
- Curiosity and experimentation are key to learning AI
- Scaling requires systems, not just effort
- Multifamily investing allows for more efficient growth
- The future of real estate is increasingly tech-driven
Relevant Topics Discussed
- AI in real estate investing
- Direct mail marketing strategies
- Data segmentation and targeting
- Multifamily vs single-family investing
- CRM automation and lead management
- Virtual assistants and remote management
- Call tracking and sales insights
- Marketing ROI and response rates
- Tech integration in real estate businesses
- Future trends in AI and investing
Why Should You Listen?
Listen to this episode if you:
- Want to improve your marketing results and deal flow
- Are curious how AI applies to real estate
- Feel overwhelmed by technology but want to learn
- Want to automate parts of your business
- Are looking to scale more efficiently
This episode shows you how to bridge the gap between real estate and technology — without needing to be an expert.
Important Links:
About Jason Macht
Jason Macht is the founder of White Space Solutions and REmail Direct, two companies at the intersection of real estate, data, and applied AI. White Space Solutions (whitespacesolutions.ai) is an AI automation consultancy serving real estate investors and business owners. The firm builds growth infrastructure — from CRM integrations and workflow automation to AI-powered call scoring and lead attribution systems — that turns operational complexity into competitive advantage. REmail (remaildirect.com) is a direct mail automation platform purpose-built for real estate investors.
Backed by 20M+ mailers sent, the platform delivers done-with-you campaigns with full transparency, data-driven list selection, and automated fulfillment. Clients consistently see 5x+ ROAS, with top performers reaching 10x returns. Jason’s career spans 15 years across engineering, product management, and fintech before pivoting into real estate and technology. With an engineering background, he brings a systems-first mindset to everything — building infrastructure that compounds rather than tactics that expire. His real estate portfolio includes 21 units across multiple markets, giving him firsthand operator experience that informs the tools and services he builds for clients.