1:03:38

In this episode of the You Winning Life podcast, host Jason Wasser, LMFT, interviews Dr. Elaine Stageberg, a psychiatrist turned real‑estate investor and private‑equity fund founder. Dr. Stageberg recounts her unconventional career path—from an undergraduate biology major, through a Master’s in Health Administration, medical school, and psychiatry—to discovering real‑estate investing as a vehicle for financial freedom. She explains how she and her husband, Nick, began investing during medical school, using modest salaries to buy distressed properties, refinance, and recycle capital. Their business evolved from solo rentals to a property‑management company, joint ventures, and ultimately a private‑equity fund managing roughly a third of a billion dollars in assets. Dr. Stageberg introduces a developmental‑stage framework for businesses, likening a startup to a baby, toddler, teenager, and adult, each with distinct needs and challenges. She discusses the importance of storytelling, mindset, and resilience, especially when facing personal hardships such as loss and pregnancy complications. The conversation also covers the role of mentorship, building trusted teams, navigating compliance, and the value of interdisciplinary learning. Practical resources are shared, including their website (meetblackswan.com), free educational content, a real‑estate dictionary, and recommended reading (e.g., Rich Dad Poor Dad, Think and Grow Rich, The Road Less Stupid, The Surrender Experiment). The episode concludes with actionable advice for clinicians and other professionals seeking to diversify income, embrace entrepreneurship, and create financial freedom while maintaining their primary vocation.

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