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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Real estate success often appears chaotic, involving flipping houses, managing contractors, and juggling staff. What if there was a smarter way to scale without burning out? Rich did it with innovative systems, a remote team, and relentless problem-solving. Could his approach change how you build wealth?
In this episode, the hosts talk with Rich about his path from nuclear engineering to real estate investing. He shares his early ventures, building a rental portfolio, flipping homes, and managing a team of virtual assistants from the Philippines. Rich explains how he scaled his business through direct mail marketing, targeting niche markets, and creative strategies. The conversation offers practical advice, real examples, and lessons for aspiring real estate investors.
You’ll Learn How To:
- Build a real estate business from rentals and flips
- Scale operations using virtual assistants and efficient systems
- Generate consistent deal flow through direct mail marketing
- Structure teams and processes for high-volume property management
- Navigate cash-flow markets outside your local area
Who This Episode Is For:
- Aspiring real estate investors looking for practical scaling tips
- Entrepreneurs interested in leveraging remote teams effectively
- Investors exploring rentals, flips, or hybrid strategies
- Anyone curious about managing multiple properties without burnout
Why You Should Listen:
This episode shows how to grow a real estate business smartly and sustainably. Rich shares his journey from engineering to real estate, reveals how he built high-performing teams in the Philippines, and breaks down his approach to deal flow, direct mail marketing, and scaling a portfolio while keeping stress low.
What You’ll Learn in This Episode:
00:00 How Rich enters the episode and early banter about bourbon
03:00 What shaped Rich’s background from engineering to entrepreneurship
07:00 Why nuclear engineering pushed Rich to rethink his career path
10:00 How bartending and online traffic businesses shaped his mindset
13:00 What pushed Rich to explore real estate during the 2008 crash
16:00 How buying one rental a year grew into major deal volume
20:00 Why Rich stopped flipping during the pandemic and changed direction
23:00 How scaling to 14 employees affected operations and stress
26:00 What inspired Rich to stay private and avoid public visibility
31:00 Effective Niches for Mailing Campaigns
37:00 Marketing Channels and Personal Preferences
Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/
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