{"podcast":{"title":"The Julian Castle Show","slug":"the-julian-castle-show-6594550","podcast_index_feed_id":6594550,"rss_url":"https://anchor.fm/s/e6c34a38/podcast/rss","website_url":"https://podcasters.spotify.com/pod/show/julian-castle","image_url":"https://d3t3ozftmdmh3i.cloudfront.net/staging/podcast_uploaded_nologo/38615582/38615582-1772031949694-0648a9894a951.jpg","author":"Julian Castle","episode_count":132,"summary":"You’re not here for motivation. You’re here to see how real operators build companies over time. I build in public, breaking down the reality of distressed real estate using The Whole Deal Method: solving the entire situation, not just chasing a fee. You’ll hear real numbers and the decisions I make when things get ugly. I also interview 120+ proven entrepreneurs to unpack how they manage downside and compound over years. To understand deals, risk, and execution so you can build your machine, this is your training ground. Practical breakdowns and zero fluff.","last_synced_at":"2026-06-26T08:20:57.053490+00:00","page_url":"https://stenobird.com/podcast/the-julian-castle-show-6594550"},"episode":{"title":"Midwest Multifamily, Real Risk & Real AI: How Carter Olles Underwrites Deals in 30 Minutes","slug":"midwest-multifamily-real-risk-real-ai-how-carter-olles-underwrites-deals-in-30-minutes","published_at":"2026-06-16T16:10:06+00:00","page_url":"https://stenobird.com/podcast/the-julian-castle-show-6594550/midwest-multifamily-real-risk-real-ai-how-carter-olles-underwrites-deals-in-30-minutes","show_page_url":"https://stenobird.com/podcast/the-julian-castle-show-6594550","url":"https://podcasters.spotify.com/pod/show/julian-castle/episodes/Midwest-Multifamily--Real-Risk--Real-AI-How-Carter-Olles-Underwrites-Deals-in-30-Minutes-e3kscce","audio_url":"https://anchor.fm/s/e6c34a38/podcast/play/121565006/https%3A%2F%2Fd3ctxlq1ktw2nl.cloudfront.net%2Fstaging%2F2026-5-16%2F426256572-44100-2-0244b149ed897.m4a","summary":"Here's a summary of the conversation between Julian Castle and Carter Olles: Introduction and Background: Julian introduces Carter Olles, co-founder of Nautilus, a Midwest-focused multifamily investment firm. Carter has a background in Midwest acquisitions and emphasizes conservative underwriting and operational excellence. Investment Strategy: Nautilus focuses on acquiring quality multifamily properties in the Midwest. Carter highlights the Midwest's steady performance, disciplined supply, and strong rent growth. The firm targets light value-add to core-plus properties with conservative leverage. Entrepreneurial Journey: Carter co-founded Bright Young Dyslexics to support dyslexic students, which taught him operational discipline. His career path included significant roles at MLG, where he learned the importance of seizing opportunities and building relationships. Market Insights: Carter discusses the impact of interest rates and rent growth on acquisitions. He emphasizes the importance of thorough due diligence, especially regarding CapEx and physical assets. Operational Excellence: Nautilus prioritizes speed and data-informed decisions in asset management. The firm uses AI cautiously for underwriting and content, focusing on security and efficiency. Future Outlook: Carter is optimistic about the Midwest's potential and the role of AI in enhancing operations. He stresses the importance of relationships and continuous learning in real estate. Key Takeaways: Disciplined investing and leveraging knowledge are crucial. The Midwest offers unique opportunities with its stable market dynamics. This summary captures the essence of the conversation, highlighting Carter's strategic approach and insights into the real estate market.Carter Olles’s Social Media: https://www.insta…","meta_description":"Here's a summary of the conversation between Julian Castle and Carter Olles: Introduction and Background: Julian introduces Carter Olles, co-founder of Na…","key_points":[],"chapters":[],"topics":[],"duration_seconds":4637,"processing_state":"not_requested","actions":[{"name":"request_transcript","method":"POST","url":"https://stenobird.com/v1/public/podcasts/the-julian-castle-show-6594550/episodes/midwest-multifamily-real-risk-real-ai-how-carter-olles-underwrites-deals-in-30-minutes/transcription-requests","description":"Idempotently request low-priority transcript generation for this episode."},{"name":"read_markdown","method":"GET","url":"https://stenobird.com/podcast/the-julian-castle-show-6594550/midwest-multifamily-real-risk-real-ai-how-carter-olles-underwrites-deals-in-30-minutes.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}