Paging Financial Freedom

Daniel Shin, MD and Lila Kaplan, CFP

5.0 (4)
Investing

This podcast is about empowering doctors and their spouses to break free from the golden handcuffs of medicine by building wealth through real estate and smart financial strategies. Through our personal journeys and hard-won lessons, we share practical tools to help you create more freedom, flexibility, and control over your time and future.

2d ago

20. Real Estate Investing in the Age of AI with Tim Fergestad

In this episode of Paging Financial Freedom, Dr. Daniel Shin sits down with Tim Fergestad, Ph.D., neuroscientist, real estate investor and founder of Oak Street Assets, to discuss the importance of asset ownership, building wealth beyond a high-income career and finding opportunities in today's real estate market. Tim shares how he transitioned from scientific research to full-time real estate investing, what he learned while managing his family's finances alongside his anesthesiologist wife, and why traditional financial education often falls short for highly trained professionals. He also explains how his investing journey evolved into partnerships involving more than $500 million in real estate. The conversation explores the difference between earning income and owning assets, the potential impact of artificial intelligence on financial independence, real estate tax advantages and the opportunities emerging in the multifamily market. Tim and Daniel also discuss how investors can approach market cycles without trying to predict the exact bottom. Key Takeaways 00:48 – Meet Tim Fergestad and Oak Street Assets 02:10 – From neuroscience to real estate investing 04:25 – Leaving scientific research behind 06:15 – Learning about investments and hidden fees 08:53 – Why Tim chose alternative investments 09:22 – The income economy vs. the asset economy 11:10 – The benefits of owning income-producing assets 12:14 – Real Estate Professional Status and tax advantages 14:05 – Why ownership matters in the age of AI 16:46 – AI, employment and financial independence 19:46 – Where we are in the real estate market cycle 22:01 – Preferred equity opportunities in multifamily 23:42 – Finding opportunities during market downturns 24:48 – Why timing the market is so difficult 25:37 – The Phoenix Prosperity Podcast and what's next 26:03 – Where to connect with Tim About Tim Tim Fergestad, Ph.D., is a scientist, real estate investor and founder and principal of Oak Street Assets. After earning his Ph.D. in neuroscience and conducting research at the University of Wisconsin–Madison, Tim transitioned into real estate investing. Today, he works with investors across multifamily real estate and private real estate credit opportunities. He is also the host of the Phoenix Prosperity Podcast. ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Connect with Tim Fergestad: Connect with him on Tim Fergestad on LinkedIn Check his personal website: TimFergestad.com Explore Oak Street Assets Listen to the Phoenix Prosperity Podcast Tim's email: tim@timfergestad.com ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Links from the Episode: 🔗 Apple Podcast 🔗 Spotify 🔗 Dr. Daniel Shin’s Real Estate Platform: Cereus Real Estate 🔗 Lila Kaplan’s Real Estate Investment Firm: Silverback Equity Partners ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Stay Connected with Us: 👉 LinkedIn 👉 Instagram: Daniel Shin and Lila Kaplan 👉 YouTube: The Paging Financial Freedom Podcast
Oct 7

19. How We Saved $1 million in Taxes Using Real Estate

In this episode of Paging Financial Freedom, Dr. Daniel Shin and Lila Kaplan break down some of the most important real estate tax strategies physicians and their spouses should understand. Drawing from their own investing experience, Daniel and Lila estimate that they have collectively saved more than $1 million in taxes over the past decade through real estate. They explain how depreciation works, what it takes to qualify for Real Estate Professional Status (REPS), and how certain short-term rental strategies can allow investors to use depreciation against active income. Daniel and Lila also share examples from their own portfolios, including tax refunds they received after putting these strategies to work. The conversation also covers depreciation recapture and 1031 exchanges, including how investors can defer capital gains when moving from one investment property to another. Throughout the episode, Daniel and Lila emphasize the importance of understanding the rules, tracking your activity and working with a CPA who specializes in real estate. Key Takeaways 00:45 – Why real estate and taxes go hand in hand 01:50 – How Daniel and Lila saved over $1 million in taxes 02:45 – Looking at the tax code as a playbook 04:02 – Four real estate tax strategies to understand 05:11 – How real estate depreciation works 07:31 – Real Estate Professional Status (REPS) explained 09:15 – How REPS can offset active income 11:44 – Lila’s experience using REPS 13:50 – How Daniel qualified for REPS as a physician 15:08 – The short-term rental tax strategy 17:27 – Reinvesting tax savings to compound wealth 18:16 – Depreciation recapture and 1031 exchanges 20:27 – The rules and deadlines behind a 1031 exchange 21:01 – Why working with a real estate CPA matters Disclaimer: Daniel and Lila share their personal experiences for educational purposes and are not providing individualized tax advice. Consult a qualified tax professional regarding your specific situation. ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Links from the Episode: 🔗 Apple Podcast 🔗 Spotify 🔗 Dr. Daniel Shin’s Real Estate Platform: Cereus Real Estate 🔗 Lila Kaplan’s Real Estate Investment Firm: Silverback Equity Partners ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Stay Connected with Us: 👉 LinkedIn 👉 Instagram: Daniel Shin and Lila Kaplan 👉 YouTube:The Paging Financial Freedom Podcast
Sep 23

18. How a Radiologist Reached Financial Freedom in 18 Months with Param Baladandapani

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. Param Baladandapani, radiologist and founder of Generational Wealth MD, to discuss how physicians can use real estate to build financial freedom in a way that fits their time, goals and risk tolerance. Param shares how her family’s experience with real estate influenced her early investing journey, why it took her three years to purchase her first property, and what eventually pushed her to accelerate her portfolio. After realizing the stock market could take her 17 years to reach financial freedom, she became more active with real estate strategies and reached her financial freedom goal in approximately 18 months. The conversation explores passive versus active investing, real estate tax strategies, managing risk, investing through different market cycles and how financial freedom can give physicians more options when life changes unexpectedly. Param also shares practical ways doctors can begin investing based on how much time and involvement they actually want. Key Takeaways 01:44 – Param’s path to medicine and radiology 03:28 – Why financial freedom became about more than money 04:25 – How Param first discovered real estate investing 06:21 – Why it took three years to buy her first property 07:11 – The career disruption that changed her financial plans 07:46 – From a 17-year timeline to financial freedom in 18 months 08:32 – Building an out-of-state rental portfolio 09:19 – Three different paths to financial freedom through real estate 13:06 – Why financial freedom doesn’t have to mean leaving medicine 15:55 – Investing when your spouse is more risk-averse 18:10 – Three ways to reduce risk in real estate 23:21 – Lessons from the recent real estate market cycle 25:47 – Where physicians can start with real estate 28:58 – What to do when fear of making a costly mistake holds you back 30:15 – Markets Param is watching today 32:03 – Cash-on-cash returns and what she looks for in a deal 32:41 – The investing advice that stuck with Param 33:25 – Generational Wealth MD, GW Capital and resources for investors About Param Dr. Param Baladandapani is a radiologist, real estate investor and founder of Generational Wealth MD, a community focused on helping physicians build wealth through real estate. After initially investing passively in long-term rentals, she accelerated her portfolio using more active strategies and reached financial freedom in approximately 18 months. Today, she educates physicians on active and passive real estate investing, tax strategies and building financial independence with an approach that fits their individual goals. Connect with Param: Follow her on Instagram Connect with her on LinkedIn Check her websites https://gwcapital.com/gwcapital-home and https://www.parambalamd.com/ ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Links from the Episode: 🔗 Apple Podcast 🔗 Spotify 🔗 Dr. Daniel Shin’s Real Estate Platform: Cereus Real Estate 🔗 Lila Kaplan’s Real Estate Investment Firm: Silverback Equity Partners ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Stay Connected with Us: 👉 LinkedIn 👉 Instagram: Daniel Shin and Lila Kaplan 👉 YouTube:The Paging Financial Freedom Podcast
Sep 9

17. How a Doctor Reached Financial Freedom in 3 Years with Larry Daugherty

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. Larry Daugherty, board-certified radiation oncologist, real estate investor and founder of The Freedom Physician, to discuss how he built financial independence through real estate while creating a life centered around autonomy, family and adventure. Larry shares how growing up with financial scarcity shaped his relationship with money, why he moved from Florida to Alaska, and how an unexpected crisis in his medical practice transformed real estate from a side investment into a path toward financial freedom. After buying his first fourplex in 2020, he rapidly grew his portfolio and reached the point where his real estate cash flow exceeded his physician income within three years. The conversation also explores Larry’s experiences completing the Iditarod and summiting Mount Everest, the role his wife played in building their portfolio, the realities of active real estate investing and why financial independence ultimately allowed him to rediscover his love for medicine on his own terms. Key Takeaways ~00:00 – Larry’s background and the Freedom Physician ~02:20 – Building Radiating Hope ~04:00 – Growing up with financial scarcity ~07:30 – How debate led Larry toward medicine ~11:30 – Discovering his passion for adventure ~14:00 – Losing autonomy in academic medicine ~17:00 – Moving to Alaska and pursuing the Iditarod ~21:00 – Reaching a positive net worth at 40 ~23:00 – Discovering real estate at PIMDCon ~25:00 – His first fourplex and real estate cash flow ~28:00 – How COVID changed his financial priorities ~30:00 – Reaching financial freedom in three years ~34:30 – Practicing medicine on his own terms ~36:00 – Prairie’s role in their real estate journey ~39:00 – The reality of active real estate investing ~42:00 – Investing in today’s real estate market About the Larry: Dr. Larry Daugherty is a board-certified radiation oncologist, real estate investor and founder of The Freedom Physician. Based in Alaska, he has built a real estate portfolio of approximately $40 million and more than 200 multifamily units while mentoring physicians on financial independence and intentional living. He is also an accomplished adventurer who has completed the Iditarod four times, summited Mount Everest and co-founded Radiating Hope, a nonprofit expanding access to cancer treatment in underserved countries. ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Connect with Larry! Follow him on Instagram Check his website: The Freedom Physician Larry’s email: larry@thefreedomphysician.com Some websites Larry would like for you to check it out: Radiating Hope and Basecamp Mastermind ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Links from the Episode: 🔗 Apple Podcast 🔗 Spotify 🔗 Dr. Daniel Shin’s Real Estate Platform: Cereus Real Estate 🔗 Lila Kaplan’s Real Estate Investment Firm: Silverback Equity Partners ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Stay Connected with Us: 👉 LinkedIn 👉 Instagram: Daniel Shin and Lila Kaplan 👉 YouTube:The Paging Financial Freedom Podcast
Aug 26

16. From Medicine to a $500M Real Estate Portfolio with Dr. Elaine Stageberg

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. Elaine Stagerberg, psychiatrist, mother of six and co-founder of Black Swan Real Estate, to discuss her journey from medicine and single-family rentals to building a vertically integrated real estate company with more than 2,300 units and approximately $500 million in assets under management. Elaine shares how financial insecurity early in life shaped her relationship with money, why she and her husband began investing before she even started medical school, and how her training in psychiatry became an unexpected advantage in working with investors. She also explains how the pandemic changed the trajectory of her career and ultimately led her away from clinical medicine and into Black Swan Real Estate full-time. The conversation explores financial security versus financial freedom, building wealth as a couple, overcoming limiting beliefs around investing, and the importance of creating clear roles when spouses build a business together. Elaine also shares how she and Nick approach legacy and what they hope to teach their six children about money, values and creating their own lives. Key Takeaways 02:45 – Elaine shares how her childhood, medical training, marriage and early real estate investments eventually came together to shape the life she has today. 05:41 – How training in psychiatry and therapy became an unexpected advantage in investor relations and understanding how people think about money. 08:42 – Elaine reflects on growing up with financial insecurity and how scarcity initially made her more risk-averse as an investor. 10:29 – Why she came to see financial security and financial freedom as two sides of the same coin. 12:18 – How Elaine and her husband Nick built Black Swan Real Estate together and eventually divided responsibilities across acquisitions, operations and investor relations. 15:37 – Elaine explains her practice of “visioning” and the future she originally imagined while she was still in medical school. 17:20 – How the pandemic led Elaine to step away from clinical medicine and created an unexpected opportunity to grow their real estate portfolio. 20:08 – The difficult identity shift from physician to entrepreneur and why Elaine approached leaving medicine one day at a time. 24:51 – Why Elaine eventually created a coaching program combining psychiatry, entrepreneurship, leadership, investing and human development. 26:22 – The simple monthly balance sheet practice Elaine and Nick have maintained since 2011 and how it helped them learn to communicate about money. 32:49 – Why limiting beliefs like being “too young,” “too old” or not earning enough often prevent people from taking their first step toward investing. 36:29 – What Elaine believes has been the hardest part of building a $500 million business and why leadership growth begins with mindset. 39:46 – The mistake Elaine and Nick made by both trying to lead the same areas of their company and how defining clear “zones of genius” changed their business and marriage. 45:48 – How couples with different risk tolerances can approach real estate investing and why Elaine evaluates investments based on the specific dollar, goal and moment. 48:42 – How Elaine and Nick think about inheritance, trusts and teaching their children values before transferring wealth. 51:43 – Rapid-fire lessons on financial advice, spending, taxes and the book Elaine returns to again and again. About the Elaine: Dr. Elaine Stagerberg is a psychiatrist, real estate investor and co-founder of Black Swan Real Estate, a vertically integrated real estate company with more than 2,300 units and approximately $500 million in assets under management. She leads investor relations and capital raising while working alongside her husband, Nick, who co-founded the company with her. ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Connect with Dr. Elaine Stagerberg Follow her on Instagram and Black Swan Real Estate's profile Connect with her on LinkedIn Subscribe to Black Swan Real Estate's channel on YouTube Check her websites: https://blackswanteam.com/ and https://allset.mykajabi.com/coaching Newsletter & Investor Calls: Available through her website ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Links from the Episode: 🔗 Apple Podcast 🔗 Spotify 🔗 Dr. Daniel Shin’s Real Estate Platform: Cereus Real Estate 🔗 Lila Kaplan’s Real Estate Investment Firm: Silverback Equity Partners ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Stay Connected with Us: 👉 LinkedIn 👉 Instagram: Daniel Shin and Lila Kaplan 👉 YouTube:The Paging Financial Freedom Podcast
Aug 12

15. Why Doctors Don’t Get Rich with Dr. Tom Burns

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 Dr. Tom Burns, orthopedic surgeon, real estate investor and author of Why Doctors Don’t Get Rich, to discuss how physicians can build wealth and create greater freedom beyond their medical careers. Tom shares how he began investing in real estate during orthopedic residency and gradually built passive income alongside his career in medicine. He also shares the unexpected story behind his friendship with Rich Dad Poor Dad author Robert Kiyosaki and how that relationship eventually inspired him to write his own book. The conversation explores why a high physician income does not necessarily lead to financial independence, how passive income can help doctors regain control over their time and what Tom has learned from investing through multiple real estate cycles. Daniel, Lila and Tom also discuss evaluating passive investments, choosing experienced operators, involving your spouse in financial decisions and redefining what it actually means to be “rich.” Key Takeaways: 02:27 – Tom shares the remarkable story of discovering an early self-published copy of Rich Dad Poor Dad and how it led to his friendship with Robert Kiyosaki. 06:29 – How Tom’s upbringing and early relationship with money shaped his approach to earning, saving, and investing. 07:39 – Why Tom chose orthopedic surgery and how he eventually became a physician for the U.S. Ski Team. 10:57 – What it means to be a “rich doctor” and why Tom believes true wealth is ultimately about having choices. 12:41 – How the business of medicine has changed and why physicians today have less control over their careers. 15:21 – Why Tom began looking beyond medicine during orthopedic residency and ultimately chose real estate. 19:15 – The decision to prioritize building his real estate portfolio rather than simply becoming a busier physician. 21:36 – How Tom’s investments evolved from small properties into larger projects, partnerships, and multiple forms of passive and active income. 24:17 – The evolution of R&B Capital and Presario Ventures, including developing a 240-unit apartment project during the Global Financial Crisis. 26:33 – Lessons from investing through multiple financial crises and why Tom believes compelling multifamily opportunities are emerging again. 30:16 – Tom’s advice for physicians returning to real estate investing and why thoroughly vetting operators matters. 31:45 – The role Tom’s wife played in their financial life and how their approach to investing evolved into a true partnership. 34:31 – Why financial freedom is about much more than reaching a number and how smaller financial milestones can create meaningful changes in your life. 38:19 – How passive income allowed Tom to gradually buy back his time, beginning with taking Friday afternoons away from the office. 40:19 – How Robert Kiyosaki encouraged Tom to write Why Doctors Don’t Get Rich and what Tom hopes readers take away from the book. 43:40 – Rapid-fire lessons on investing, financial advice, books, daily routines, and Tom’s personal definition of being rich. About Tom: Dr. Tom Burns is an orthopedic surgeon, real estate investor and author of Why Doctors Don’t Get Rich. He began investing during residency and has since built a diversified real estate portfolio while continuing his career in medicine. Through Rich Doctor, Tom now shares what he has learned about passive income, financial independence and creating more freedom outside of a traditional medical career. ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Connect with Tom Burns: Follow him on Instagram Connect with him on LinkedIn Check his website https://richdoctor.com/ Buy his book Why Doctors Don’t Get Rich Dr. Tom’s email: hello@richdoctor.com ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Links from the Episode: 🔗 Apple Podcast 🔗 Spotify 🔗 Dr. Daniel Shin’s Real Estate Platform: Cereus Real Estate 🔗 Lila Kaplan’s Real Estate Investment Firm: Silverback Equity Partners ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Stay Connected with Us: 👉 LinkedIn 👉 Instagram: Daniel Shin and Lila Kaplan 👉 YouTube:The Paging Financial Freedom Podcast
Jul 29

14. How Real Estate Helped This Physician Reclaim Her Time and Family Life with Dr. Marissa Caudill

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. Marissa Caudill, a psychiatrist, entrepreneur and real estate investor, to discuss her journey beyond traditional medicine and how physicians can build greater freedom through entrepreneurship, investing and emerging technologies like artificial intelligence. Dr. Caudill shares how her career evolved from practicing psychiatry within a large healthcare system to building multiple income streams through real estate investing, business ownership and AI consulting. She reflects on the challenges of physician burnout, the importance of financial independence and why many doctors are beginning to rethink what a successful medical career can look like. Throughout the conversation, Daniel, Lila and Marissa explore the mindset shifts required to move beyond a traditional W-2 career, how physicians can leverage technology to improve efficiency, and why creating multiple sources of income can provide greater flexibility for both personal and professional life. They also discuss balancing entrepreneurship with family, overcoming fear when making career transitions and the role AI is likely to play in the future of healthcare. Key Takeaways: 00:00 – Introduction to Dr. Marissa Caudill and her work in psychiatry, parenting, and entrepreneurship. 04:00 – Growing up in a working-class family and the financial lessons that shaped her future. 08:30 – How scholarships, an MD-PhD program, and research funding allowed her to complete medical training with minimal debt. 12:00 – Why she unexpectedly chose psychiatry and never looked back. 17:00 – Motherhood, shifting priorities, and the move away from academia. 22:00 – The realities of practicing psychiatry at Kaiser during the COVID-19 pandemic. 28:00 – Burnout, identity shifts, and the decision to leave a full-time employed physician role. 31:30 – How a New Hampshire real estate investment became the catalyst for greater lifestyle freedom. 36:00 – Balancing marriage, real estate investing, and entrepreneurial risk-taking. 41:00 – The vision behind Super Doc Tech and how AI can help physicians build scalable businesses. 47:00 – Why doctors should think beyond one-to-one clinical work and embrace technology to expand their impact. Dr. Caudill's journey serves as a powerful reminder that physicians can leverage their expertise in ways that extend far beyond the exam room, creating both greater impact and greater freedom. ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Connect with Dr. Marissa! Follow Marissa on Instagram. Connect with her on LinkedIn. Learn more about Super Do Tech and The Parent Doctor Links from the Episode: 🔗 Apple Podcast 🔗 Spotify 🔗 Dr. Daniel Shin’s Real Estate Platform: Cereus Real Estate 🔗 Lila Kaplan’s Real Estate Investment Firm: Silverback Equity Partners ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Stay Connected with Us: 👉 LinkedIn 👉 Instagram: Daniel Shin and Lila Kaplan 👉 YouTube:The Paging Financial Freedom Podcast
Jul 15

13. The Godfather of Multifamily Lending Predicts What's Next with Paul Peebles

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, welcome Paul Peebles, nationally recognized multifamily lender and underwriter at Old Capital, for an in-depth discussion on commercial real estate cycles, lending, and today's multifamily investment landscape. Known throughout the industry as the "Godfather of Multifamily Lending," Paul has spent nearly four decades financing apartment communities across the United States, personally structuring more than $9 billion in transactions through Fannie Mae, Freddie Mac, HUD, CMBS, life insurance companies and private lenders. Drawing from his experience through multiple economic cycles, he explains how history continues to repeat itself and why understanding past market disruptions is essential for today's investors. The conversation explores the Savings & Loan Crisis, the 2008 Global Financial Crisis and the recent correction in multifamily real estate caused by aggressive bridge lending and rapidly rising interest rates. Paul explains why many syndications struggled after 2022, how financing decisions often determine investment outcomes, and why today's market may present one of the most compelling buying opportunities in years. Key Takeaways 02:30 – Paul explains how he became known as the "Godfather of Multifamily Lending." 04:00 – Lessons from the Savings & Loan Crisis and how deregulation reshaped commercial real estate. 09:10 – The 2008 financial crisis, subprime lending and the biggest mistakes investors made. 13:35 – Why today's apartment market mirrors previous market corrections. 16:45 – Why Paul believes today's pricing may create one of the best buying opportunities in years. 17:00 – How AI could impact different multifamily asset classes. 18:30 – Why apartments have historically remained more resilient than office, retail and other commercial sectors. 21:00 – Can investors recognize a real estate bubble before it bursts? 24:15 – Why fixed-rate debt often outperforms bridge loans across market cycles. 25:10 – Paul's advice for physicians considering passive multifamily investments. 29:20 – Warning signs investors should watch for before the next real estate bubble. 31:30 – Why projected IRRs can be misleading and how investors should evaluate syndications. 35:20 – What lenders actually look for before approving a multifamily loan. 39:30 – Why Texas continues attracting businesses, population growth and multifamily investment. 46:00 – Paul's advice for doctors investing their first $500,000. 48:20 – The legacy Paul hopes to leave through investor education. Daniel, Lila and Paul also discuss artificial intelligence's potential impact on housing demand, why multifamily continues to outperform many other commercial asset classes during downturns, how passive investors should evaluate syndicators and operators, and why discipline, liquidity and conservative underwriting remain the keys to long-term success. ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Connect with Paul Peebles! • Connect with Paul Peebles on LinkedIn: https://www.linkedin.com/in/paul-peebles-b09289b/ • Paul's email: ppeebles@oldcapitallending.com • Learn more about Old Capital: https://oldcapitallending.com/ • Attend the Old Capital Conference: https://oldcapitalconference.com/ Links from the Episode: 🔗 Apple Podcast: https://podcasts.apple.com/ 🔗 Spotify: https://open.spotify.com/ 🔗 Dr. Daniel Shin’s Real Estate Platform: Cereus Real Estate 🔗 Lila Kaplan’s Real Estate Investment Firm: Silverback Equity Partners ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Stay Connected with Us: 👉 LinkedIn: / paging-financial-freedom-7389683382651240448 👉 Instagram: @PagingFinancialFreedom 👉 YouTube: / @pagingfinancialfreedom

5

out of 5

4 Ratings

This podcast is about empowering doctors and their spouses to break free from the golden handcuffs of medicine by building wealth through real estate and smart financial strategies. Through our personal journeys and hard-won lessons, we share practical tools to help you create more freedom, flexibility, and control over your time and future.

Creator

Daniel Shin, MD and Lila Kaplan, CFP
Years Active

2025 - 2026
Episodes

20
Rating

Clean
Copyright

© 2026 Paging Financial Freedom
Show Website

Paging Financial Freedom

Medicine

Medicine

Updated Biweekly