71. How Private Lending, AI, & Midterm Rentals Create Freedom With Jennie Berger and Tristan Lora

Send us Fan MailIn this captivating episode of Real Life Investing, Jason and Rachel Wagner sit down with powerhouse duo Jennie Berger and Tristan Lora for a conversation that blends real estate savvy, entrepreneurial resilience, lifestyle design, and some truly unforgettable stories.Jennie shares her inspiring journey from high-stakes condo development and house flipping to building a thriving private lending business. She opens up about lessons learned from challenging projects, the art of calculated risk-taking, and how she structures deals to protect her capital—plus the surprising role her self-directed Roth IRA plays in her lending portfolio. Tristan jumps in with insights from his high-energy career in live events and race car street production, showing how creativity, adaptability, and AI tools fuel his work.Beyond business, the episode explores their shared commitment to health, plant-based living, and intentional lifestyle choices. The conversation flows into midterm rental strategies, navigating tenant relationships, and the balance between financial returns and personal freedom. Along the way, listeners are treated to hilarious and heartfelt anecdotes—ghost stories, “slow-play” romance, and even the science of hugs—that reveal the warmth and authenticity behind their success.Whether you’re a real estate investor, entrepreneur, or someone seeking inspiration to design a healthier, more intentional life, this episode delivers a rare mix of actionable advice, personal wisdom, and pure entertainment.IG: @Propertypeoplellc