From Burnout to Financial Freedom

From Burnout to Financial Freedom

In this episode of Paging Financial Freedom, Dr. Daniel Shin, surgeon and real estate investor, and Lila Kaplan, former Wall Street professional and certified financial planner, sit down with Dr. Olga Deengar, board-certified internal medicine physician, certified life coach, and host of the Coffee Playdate Podcast, to discuss physician burnout, identity shifts, entrepreneurship and what financial freedom truly means beyond medicine. Dr. Deengar shares her journey from growing up across three countries to becoming a physician, navigating residency and motherhood during the COVID-19 pandemic, and ultimately transitioning from full-time hospitalist work to life coaching and entrepreneurship. She opens up about the challenges of balancing medicine, family and personal fulfillment, including the difficult decision to send her first child to live with grandparents during residency because of the demands of medical training. The conversation explores physician burnout, career transitions, mindset coaching, financial freedom versus financial independence and how doctors can intentionally design a life aligned with their values. Daniel, Lila, and Olga also discuss entrepreneurship, family goal-setting, multiple streams of income and why many physicians struggle with identity outside of medicine. Key Takeaways: 03:34 – Olga shares her international upbringing and journey from Russia to Israel, Canada, and eventually the United States. 09:33 – Why success in medicine didn’t fully satisfy her and the realization that something was missing. 13:26 – The DAMA Method and her framework for helping physicians achieve meaningful goals. 22:17 – Treating your family like a business and creating a shared vision with your spouse. 24:05 – Burnout versus fulfillment and the importance of intentional self-care. 27:25 – Building multiple streams of income and creating greater financial flexibility. 29:18 – The difference between financial freedom and financial independence. 37:22 – Olga’s advice for physicians feeling stuck and unsure about their next chapter. Daniel, Lila, and Olga emphasize that financial freedom is about more than money—it’s about creating options, aligning your work with your values, and designing a life that supports both professional success and personal fulfillment. They highlight the importance of mindset, entrepreneurship, intentional planning, and building income streams that provide flexibility and control over your future. Links Mentioned in the Episode: * Paging Financial Freedom Podcast on Spotify [https://open.spotify.com/episode/2LJu4g3dtrNuHiOE4dPAG1] * Paging Financial Freedom Podcast on Apple Podcasts [https://podcasts.apple.com/us/podcast/paging-financial-freedom/id1834486356] * Learn more about Dr. Daniel Shin’s Real Estate Fund: CereusRealEstate.com [https://cereusrealestate.com/] * Learn more about Lila Kaplan’s Real Estate Investment Management Company [https://silverbackequitypartners.com/] * Dr. Olga Deengar’s Podcast: Coffee Playdate Podcast [https://register.cpso.on.ca/physician-info/?cpsonum=149651]

How Multifamily Deals Actually Work

In this episode of Paging Financial Freedom, Dr. Daniel Shin, a surgeon and real estate investor, and Lila Kaplan, a former Wall Street professional and certified financial planner, sit down with Javi Beza, co-founder of Higher Ground Investment Group, to break down the full life cycle of a multifamily real estate deal—from sourcing and underwriting properties to asset management and eventual exit strategies. Javi shares his journey from running his family’s construction equipment business into multifamily investing, how he partnered with his longtime friend Teddy Moulman to launch Higher Ground Investment Group, and why operations, systems and accountability are critical to scaling successful apartment investments.  The conversation dives into how operators find deals in competitive markets, why underwriting discipline matters more than ever and how building strong broker relationships helped Higher Ground enter markets like Des Moines, Iowa. Daniel, Lila and Javi also discuss the realities of closing large apartment deals, including due diligence, financing, capital raising and coordinating contractors and property management teams after acquisition. Additionally, they explore common operational mistakes that hurt profitability, why property managers must think like business operators and how successful multifamily investing requires constant oversight and adaptability. Key Takeaways: 04:10 – Javi explains why residential real estate wasn’t the right fit for him and how he transitioned into multifamily investing. 07:27 – The importance of accurate reporting, analytics, and keeping property managers accountable in asset management. 09:24 – How Higher Ground approaches acquisitions in today’s multifamily market and why underwriting discipline is critical. 15:07 – How new operators can build broker relationships and establish credibility when entering a market. 17:04 – A breakdown of the 90-day closing process, including due diligence, financing, and raising investor capital. 20:28 – What happens after closing a deal and how operators execute value-add renovation plans. 29:25 – How operators decide when to sell a property and why flexibility is important throughout a deal’s life cycle. 30:24 – Javi explains LIHTC (Low-Income Housing Tax Credit) properties and how affordable housing investments work. Daniel, Lila, and Javi emphasize that multifamily investing is far more than simply buying apartment buildings; it also requires strong operational systems, disciplined underwriting and active asset management to execute successfully. They highlight that successful syndication operators must remain deeply involved in every stage of the process, from acquisitions to renovations to property oversight, while continuously adapting to changing market conditions. For passive investors, partnering with experienced operators who prioritize transparency, accountability and execution can create long-term opportunities for cash flow, appreciation and financial freedom. Links Mentioned in the Episode: * Paging Financial Freedom Podcast on Spotify [https://open.spotify.com/episode/2LJu4g3dtrNuHiOE4dPAG1] * Paging Financial Freedom Podcast on Apple Podcasts [https://podcasts.apple.com/us/podcast/paging-financial-freedom/id1834486356] * Learn more about Dr. Daniel Shin’s Real Estate Fund: CereusRealEstate.com [https://cereusrealestate.com/] * Learn more about Lila Kaplan’s Real Estate Investment Management Company [https://silverbackequitypartners.com/]

Multifamily Syndications Explained for Beginners

In this episode of Paging Financial Freedom, Dr. Daniel Shin, a surgeon and real estate investor, and Lila Kaplan, a former Wall Street professional and certified financial planner, sit down with Jeremy Dyer, VP of Capital Formation at Rise48 Equity [https://rise48equity.com?utm_source=chatgpt.com], to discuss real estate syndications, passive investing, and how busy physicians can build financial freedom through multifamily real estate.  Jeremy shares his journey from tech sales into real estate investing, how passive syndications helped him reclaim time with his family, and why long-term investing, not chasing quick wins is the key to sustainable wealth creation. The conversation explores how syndications allow high-income professionals to invest passively in large apartment complexes without handling day-to-day operations. Daniel, Lila, and Jeremy also discuss real estate professional status (REPS), how passive losses can offset taxes, and why vetting the operator is far more important than flashy projected returns. Additionally, they break down current multifamily market conditions, the impact of rising interest rates and new supply, and why markets like Dallas and Phoenix may present strong opportunities in the coming years. Key Takeaways: *  02:09 – Jeremy shares his transition from tech sales into active real estate investing during the financial crisis.  *  10:11 – Discussion on real estate professional status (REPS) and how it can dramatically reduce tax exposure for high-income earners.  *  13:28 – Why real estate acts as a hedge against inflation and creates long-term wealth through appreciation and cash flow.  *  18:14 – Jeremy breaks down the role of a sponsor and what operators actually do behind the scenes.  *  24:19 – Insights into the current multifamily market cycle, interest rates, supply trends, and future opportunities.  *  31:33 – Jeremy’s advice on evaluating operators and why investors should focus on people before deals.  Daniel, Lila, and Jeremy emphasize that building financial freedom through real estate requires patience, disciplined investing, and partnering with trustworthy operators who have strong systems and proven experience. They highlight that for busy physicians and professionals, passive syndications can create a path toward greater time freedom, tax efficiency, and long-term wealth without sacrificing family life or career priorities. Links Mentioned in the Episode: * Paging Financial Freedom Podcast on Spotify [https://open.spotify.com/episode/2LJu4g3dtrNuHiOE4dPAG1] * Paging Financial Freedom Podcast on Apple Podcasts [https://podcasts.apple.com/us/podcast/paging-financial-freedom/id1834486356] * Learn more about Dr. Daniel Shin’s Real Estate Fund: CereusRealEstate.com [https://cereusrealestate.com/] * Learn more about Lila Kaplan’s Real Estate Investment Management Company [https://silverbackequitypartners.com/] Subscribe to the show and don’t miss future episodes!

Real Estate Market Bottom in 2026

In this episode of Paging Financial Freedom, Daniel Shin, a surgeon and real estate investor, and Lila Kaplan, a former Wall Street professional and certified financial planner, discuss the current state of the real estate market in 2026 and what investors can expect in the months ahead. They explore emerging trends, lending shifts, and where the biggest opportunities may lie for those pursuing financial freedom through real estate. The conversation dives into the concept of a “credit thaw,” where lending activity is expected to increase significantly, potentially unlocking more deals across the market. They analyze why multifamily real estate may be approaching a market bottom, supported by declining property prices, reduced new construction, and stabilizing rents in key cities like Dallas and Phoenix. Daniel and Lila also share insights from their own deals, including discounted acquisitions driven by distressed sellers and expiring bridge loans. Additionally, they discuss the challenges of competing with large institutional investors such as BlackRock and Morgan Stanley, as well as their cautious outlook on the struggling office sector and growing interest in medical office investments. Key Takeaways:  02:02 – Market dynamics: distressed properties, falling interest rates, and increased competition from institutional buyers. 07:15 – Insights from the Dallas market: rent stabilization, reduced construction, and improving absorption rates. 08:12 – Differentiating between pricing bottom and rental/occupancy bottom. 10:30 – Outlook for 2027 and expectations of market stabilization and recovery. 11:58 – The impact of AI on jobs and future demand for office space.  14:18 – Final thoughts on avoiding speculation and making data-driven investment decisions. Daniel and Lila emphasize the importance of staying analytical rather than speculative, recognizing opportunities during market downturns, and positioning strategically for long-term gains. They highlight that while uncertainty remains, disciplined investors who understand market cycles and act on data—not emotion—are best positioned to achieve financial freedom.

2025 in Review: Wins and Lessons

In this episode of Paging Financial Freedom, Dr. Daniel Shin, a surgeon and real estate investor, and Lila Kaplan, a former Wall Street professional and certified financial planner, reflect on their journey through 2025 and share their goals for 2026. They discuss their real estate achievements, the challenges they’ve faced, and the lessons they've learned along the way. The conversation delves into their personal and professional milestones, including Lila's success with an 82-unit apartment deal in Richardson, Texas, and the expansion of their portfolios. They highlight the opportunities they’ve seized by taking advantage of discounted properties and their efforts to overcome challenges like evictions and property stabilization. Dr. Shin and Lila also talk about their evolving real estate strategies, their goals for the coming year, and the importance of building relationships in competitive markets like Dallas. Key Takeaways: 00:00 – Introduction to the episode and the hosts’ reflections on 2025.  01:14 – Lila’s journey through the year and her successful 82-unit apartment investment in Dallas.  03:32 – The process of finding hidden potential in real estate and uncovering opportunities. 06:24 – The challenges and successes of stabilizing properties and managing delinquencies.  08:11 – Dr. Shin’s experience with capital raising and deals in Dallas and Tallahassee.  10:48 – How current economic trends and interest rates are affecting real estate opportunities. 12:30 – The importance of market research and understanding local demographics when investing. 15:09 – Lila’s strategy for continuing to expand in Dallas while exploring new markets like Kentucky. 17:45 – The benefits of having strong relationships with local investors, brokers, and lenders. 20:12 – Personal reflections on goals for 2026, including expanding portfolios and professionalizing businesses. 22:35 – The balance between business growth and personal goals, including Lila’s pickleball tournament aspiration. 24:55 – Closing thoughts on the lessons learned in 2025 and the exciting potential for the year ahead. Dr. Shin and Lila emphasize the significance of setting clear, achievable goals, building meaningful relationships, and making intentional decisions about real estate investments. They share how they plan to scale their businesses, diversify their portfolios, and continue learning and growing in 2026. Links Mentioned in the Episode: * Paging Financial Freedom Podcast on Spotify [https://open.spotify.com/show/2zZ232cBI9zRI7bTwzGlC5?_reload_cause=banner-auto-reload] & Apple Podcasts [https://podcasts.apple.com/us/podcast/paging-financial-freedom/id1834486356] * Learn more about Dr. Daniel Shin’s Real Estate Fund: CereusRealEstate.com [https://cereusrealestate.com/home] * Learn more about Lila Kaplan’s Real Estate Investment Management Company: SilverbackEquityPartners.com [https://silverbackequitypartners.com/] Subscribe to the show and don’t miss future episodes!