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.

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
Jun 24

12. The Wealth-Building Strategy Most Doctors Miss with Teddy Mohlman

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 Teddy Mohlman, Founder and CEO of Higher Ground Investment Group, to discuss his journey from private chef to multifamily real estate entrepreneur, the transition from transactional income to long-term wealth creation, and what investors need to know about real estate syndications in today's market. Teddy shares his unconventional career path, from attending culinary school and serving high-net-worth clients in Miami to becoming a successful real estate agent and eventually building a multifamily portfolio of more than 700 units. He discusses how exposure to wealthy individuals sparked his interest in real estate, why he chose to step away from a lucrative commission-based business, and how he navigated the challenges of raising investor capital and scaling a real estate investment firm. The conversation explores the mindset required to leave the security of a steady paycheck, the importance of mentorship, the realities of multifamily investing in the current economic environment, and why physicians and other high-income professionals should consider real estate as part of a broader wealth-building strategy. Daniel, Lila, and Teddy also discuss market selection, due diligence, tax benefits, and how investors can evaluate syndication opportunities with greater confidence. Key Takeaways: 03:06 – Teddy shares his early career journey, from culinary school in Hawaii to running a private chef business in Miami. 07:10 – His transition into residential real estate, becoming Rookie of the Year, and investing commissions into income-producing assets. 14:29 – Why mentorship, education, and taking calculated risks were critical to scaling his business. 21:21 – An overview of Higher Ground Investment Group and how the firm grew to approximately 700 units. 25:27 – Practical due diligence strategies passive investors can use before investing in a syndication. 27:50 – The importance of market selection, landlord-friendly regulations, and understanding local economic conditions. 30:59 – Advice for physicians looking to transition from earning active income to building passive wealth through real estate. 34:35 – The role of tax strategy, cost segregation, and working with the right CPA to maximize real estate benefits. Daniel, Lila, and Teddy emphasize that building wealth requires more than simply earning a high income. They discuss the importance of putting capital to work, surrounding yourself with knowledgeable advisors, and investing with experienced operators who prioritize investor success. The episode highlights how real estate can serve as a powerful tool for generating passive income, reducing taxes, and creating financial freedom beyond a traditional career. ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Connect with Teddy Mohlman! • Connect with Teddy Mohlman on LinkedIn • Follow Teddy on Instagram • Teddy's email: teddymo@kw.com • Learn more about Higher Ground Investment Group Links from the Episode: 🔗 Paging Financial Freedom Podcast on Apple Podcast 🔗 Paging Financial Freedom Podcast on Spotify 🔗 Dr. Daniel Shin’s Real Estate Fund 🔗 Lila Kaplan’s Real Estate Investment Firm 🔗 Teddy Mohlman, Founder and CEO of Higher Ground Investment Group ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ 💬 Stay Connected with Us: 👉 LinkedIn 👉 YouTube
Jun 10

11. From Burnout to Financial Freedom with Dr. Olga Deengar

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. ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Connect with Olga Deengar! • Connect with Dr. Olga on LinkedIn • Follow Dr. Olga on Instagram • Olga's email: coacholgamd@gmail.com • Learn more about Dr. Olga • Listen to "Coffeee Playdate", Dr. Olga's podcast. Links Mentioned in the Episode: Paging Financial Freedom Podcast on SpotifyPaging Financial Freedom Podcast on Apple PodcastsLearn more about Dr. Daniel Shin’s Real Estate Fund: CereusRealEstate.comLearn more about Lila Kaplan’s Real Estate Investment Management CompanyDr. Olga Deengar’s Podcast: Coffee Playdate Podcastˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ 💬 Stay Connected with Us: 👉 LinkedIn: / paging-financial-freedom-7389683382651240448 👉 Instagram: @PagingFinancialFreedom 👉 YouTube: / @pagingfinancialfreedom
May 27

10. How Multifamily Deals Actually Work with Javi Beza

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. ˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ Connect with Javi Baeza! • Connect with Javi Baeza on LinkedIn • Follow Javi on Instagram • Javi's email: jbaeza18@gmail.com • Learn more about Higher Ground Investment Group Links Mentioned in the Episode: Paging Financial Freedom Podcast on SpotifyPaging Financial Freedom Podcast on Apple PodcastsLearn more about Dr. Daniel Shin’s Real Estate Fund: CereusRealEstate.comLearn more about Lila Kaplan’s Real Estate Investment Management Companyˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍˍ 💬 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

17
Rating

Clean
Copyright

© 2026 Paging Financial Freedom
Show Website

Paging Financial Freedom