Truly Passive Income

Ready to stop managing headaches and keep more of your gains? In this episode, Michael O’Shea breaks down how seasoned investors pair 1031 exchanges with Delaware Statutory Trusts and then use a 721 roll-up to diversify, generate income, and add optional liquidity. He also exposes where DST fees hide and how data tools helped time the multifamily cycle. Press play to learn the smarter path from hands-on landlord to truly passive investor.

Key takeaways to listen for

• [05:05] The two tax-code words that can change everything: “permanent exclusion”
• [10:14] The simple move that lets you “exchange out” of management but keep the income
• [14:56] How a 721 roll-up turns an illiquid asset into one with quarterly liquidity
• [16:17] The hidden DST fees most investors overlook and how Origin stripped them out
• [19:04] How machine learning helps predict rent growth with 95% accuracy

Resources mentioned in this episode

• [36:02] Traction by Gino Wickman | Kindle, Paperback, and Hardcover
• [37:00] The AI Edge by Jeb Blount and Anthony Iannarino | Kindle and Hardcover 

About Michael O’Shea, CFA

Michael is the Director and Head of Private Wealth Solutions at Origin Investments, where he leads capital-raising initiatives, oversees sales strategy, and builds partnerships with Registered Investment Advisors to expand Origin’s investment platform. With more than 18 years of experience in real estate and capital markets, he has helped syndicate over $10 billion in commercial real estate investments, including $500 million in 1031 exchanges. Michael holds an MBA in Finance and Real Estate Investment from DePaul University, graduating summa cum laude, and is a CFA® charterholder. He lives in Elmhurst, Illinois, with his wife Lauren and their three children.

Connect with Michael

• Website: Origin Investments 
• Email: [email protected] 
• LinkedIn: Michael O'Shea, CFA 

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

RV parks are turning into one of the smartest plays in real estate. In this episode, attorney-turned-operator John Cascarano shares how this niche delivers consistent cash flow, strong returns, and major tax advantages. He breaks down what really drives profit, from operations to depreciation. Listen now to see why investors are jumping into RV parks before the big players move in.

Key takeaways to listen for

• [03:09] How John Cascarano went from law to leading a nationwide RV park portfolio
• [06:02] Why RV parks attract retirees, workers, and full-time travelers alike
• [10:20] The two demand curves that keep revenue steady year-round
• [16:11] Why good WiFi and clean bathrooms can make or break profits
• [22:21] The hidden risks that make building new RV parks so tough
• [34:08] How investors get paid through refis and long-term equity growth

Resources mentioned in this episode

• The Road Less Stupid by Keith J. Cunningham | Kindle and Hardcover

About John Cascarano

John is an attorney, entrepreneur, and founder of Blue Metric Group, a firm that acquires and optimizes RV parks across the United States. Before entering real estate, John practiced commercial real estate law at an AmLaw 100 firm and later founded and led several successful companies as both CEO and counsel. A graduate of Duke University with a JD from the University of Michigan Law School, he brings a sharp legal and business perspective to every deal. John is a member of the State Bars of Tennessee and Georgia and is passionate about building scalable, community-driven investments in the outdoor hospitality space.

Connect with John

• Website: Blue Metric Group 
• LinkedIn: John Cascarano
• Email: [email protected] | [email protected]

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

What if the secret to building wealth was hidden in the tax code? In this episode, we’ll reveal how the “Big, Beautiful Bill” unlocks powerful new incentives for investors. From home upgrades to commercial energy credits and bonus depreciation, these updates could change how you grow your wealth. Listen now to learn how to turn tax rules into real returns.

Key takeaways to listen for

• [01:16] What the “Big, Beautiful Bill” really means for investors 
• [06:19] Why energy-efficient home upgrades are a hidden opportunity 
• [10:55] How to capture massive commercial property deductions 
• [16:01] Why bonus depreciation changes deal math overnight 
• [20:15] What every investor should do next 

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

What if your next tax bill could become your next investment? In this episode, Attorney and OZ expert Ashley Tison explains how Qualified Opportunity Zones turn capital gains into long-term, tax-free wealth. Learn the key deadlines and strategies that set smart investors apart. Tune in to see how this little-known tax tool could reshape your wealth strategy.

Key takeaways to listen for

• [05:31]What a Qualified Opportunity Zone really is and why Congress created it 
• [05:31]The three major OZ benefits every investor should know
• [08:16]How Qualified Opportunity Zones solve failed 1031 exchanges 
• [24:42]The critical 180-day rule and how to avoid costly mistakes
• [28:25]Why the smartest investors are ditching IRR for long-term plays

Resources mentioned in this episode

• [37:00] Novogradac 2025 Opportunity Zones Summit 

[37:00] Join Ashley Tison at the Novogradac Opportunity Zones Conference on December 4 in Las Vegas, where he’ll speak on audit strategies and the OZ 1.0 to 2.0 transition. Listeners of Truly Passive Income can get 10% off with code OZPROS10% at checkout. Visit ozpros.com/podcast to learn more and claim your free month in the OZ Pros Mastermind.

About Ashley Tison

Ashley Tison, Esq. is the founder of OZPros, the leading Opportunity Zone consultancy. A leading consultant and attorney on Opportunity Zones, tax advantaged structures and investing strategies, Ashley has advised over 500 commercial property investors, family offices, investment advisors and high net worth individuals on how to how to best maximize their tax savings in real estate investments, how to maximize the positive community impact of their projects, selecting an optimal investment strategy, and properly navigating the applicable regulations. Ashley is an engaging and enthusiastic speaker and / or guest covering topics such as opportunity zones, tax advantaged alternative investments, real estate, and tax planning for leading national conferences and educational seminars.

Connect with Ashley

• Website: OZPros
• Email: [email protected] 

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

What if one accident could erase everything you’ve worked for? In this episode, Dr. Jeff Anzalone reveals how a career-ending injury became the catalyst for lasting financial freedom. He shares the mindset shift that turned fear into opportunity and built true passive income. Listen now to discover how one life-changing moment can redefine your path to wealth and independence.

Key takeaways to listen for

• Why an injury can expose the risk of relying on a single active income stream
• The key mindset shift between being debt-free and being financially free
• How Dr. Jeff lost $50,000 on a crowdfunding deal and what he learned from it
• Why the operator matters more than the projected returns
• How setting clear goals helps you choose the right operator, asset class, and deal

Resources mentioned in this episode

• Who Not How by Dan Sullivan and Dr. Benjamin Hardy | Kindle, Hardcover, and Paperback
• Financial Peace by Dave Ramsey | Hardcover and Paperback
• Rich Dad's Cashflow Quadrant by Robert T. Kiyosaki | Kindle and Paperback
• The Hands-Off Investor by Brian Burke | Kindle and Paperback

About Dr Jeff Anzalone

Dr. Jeff is a Louisiana-based periodontist, real estate investor, and founder of DebtFreeDoctor.com, a financial education platform for doctors and high-income professionals. After a skiing accident nearly ended his clinical career, Jeff realized that being debt-free is not the same as being financially free. Determined to protect his family’s future, he began building multiple streams of passive income through real estate syndications and other cash-flowing assets. Today, he helps medical and dental professionals replace active income, reduce tax burdens, and achieve financial independence so they can stop trading time for money and start living life on their own terms.

Connect with Dr. Jeff

• Website: Debt-Free Doctor 
• YouTube: Debt Free Doctor

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

How does a neurosurgeon become a billion-dollar syndicator? In this episode, Dr. Buck Joffrey shares his journey from the operating room to building a multi-billion real estate portfolio. Tune in as he breaks down why he treats investments like a business, the power of cost segregation and bonus depreciation, infinite banking strategies, and his macro outlook on interest rates, inflation, and the dollar. 

Key takeaways to listen for

• A way to build medical practices like businesses
• How to evaluate value-add multifamily and create defensible NOI growth
• Why bonus depreciation often beats 1031 exchanges for tax savings
• Everything you need to know about infinite banking
• What is meant by macro outlook, and why now is the time to buy assets

Resources mentioned in this episode

• 7 Secrets of Eternal Wealth by Buck Joffrey MD | Kindle and Paperback
• Rich Dad's Cashflow Quadrant by Robert T. Kiyosaki | Hardcover and Paperback

Explore Wealth Formula Banking and learn infinite banking strategies to grow and protect your wealth. Check out the Wealth Formula Podcast and investor resources at https://www.wealthformula.com/.

About Dr. Buck Joffrey

Matthew D. Sanchez is the Broker/Owner of MarketPlace Realty, LLC in Denver, Colorado, with over 30 years of real estate experience. Since founding the firm in 1992, he has led it to become a trusted name in residential, commercial, and land transactions across the Denver metro area. Known for his market expertise and client-first approach, Sanchez has built a reputation for integrity and consistent results. Beyond real estate, he’s actively involved in community development, reflecting his commitment to both professional excellence and local impact.

Connect with Dr. Buck

• Website: Wealth Formula
• Podcast: Wealth Formula Podcast | Apple Podcasts and Spotify

  Longevity Roadmap Podcast | Apple Podcasts and Spotify

• Facebook: Wealth Formula 
• X: @BuckJoffrey 
• LinkedIn: Buck Joffrey, MD
• YouTube: Wealth Formula  

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

Internal medicine physician and negotiation coach Dr. Gloria Esoimeme shares how she bought her first home, slashed her taxes, and, after relocating, built a new playbook focused on U.S. long-term rentals and active investments in Dubai. You’ll hear how she evaluates worst-case scenarios, what most doctors miss about physician mortgages, and the on-the-ground realities of buying “off-plan” in the UAE, so better tune in!

Key takeaways to listen for

• [10:32] The best window to use a physician mortgage
• [15:32] Short-term rentals for depreciation, not cash flow
• [23:04] Why STR hours differ from 750-hour REPS
• [26:04] U.S. long-term rentals + active deals in Dubai without a W-2
• [29:42] Dubai basics that investors should know and remember

Resources mentioned in this episode

• [41:13] How to Win Friends and Influence People by Dale Carnegie | Paperback, Hardcover, and Kindle
• [41:13] YouVersion Bible App

About Dr. Gloria Esoimeme

Dr. Gloria Esoimeme is a physician and researcher with expertise in clinical medicine and public health. She has contributed to peer-reviewed publications and is passionate about advancing healthcare access, quality, and education. With a strong commitment to community health initiatives, Dr. Esoimeme focuses on bridging the gap between research and practice to improve patient outcomes and empower future healthcare leaders.

Connect with Dr. Gloria

• Podcast: Negotiation Secrets With Dr Gloria Esoimeme | Apple Podcasts
• Facebook: ​​DrGloria Esoimeme
• Instagram: @gloriaesoimeme
• LinkedIn: Dr Gloria Esoimeme

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

Tad Fallows lays out how sophisticated LPs actually build resilience. Start with human networks, target low-correlation, equity-like returns, and never forget the unsexy stuff. Dial in as we cover private-market due diligence, when a wealth manager does (and doesn’t) add value, raising grounded kids around wealth, and how to apply the “holy grail” of diversification without turning your portfolio into a museum of asset classes.

Key takeaways to listen for

• [10:42] The most overlooked risk tool for affluent families
• [18:43] Low correlation to public markets with equity-like returns
• [23:59] Why you should diversify by operating exposure
• [27:22] Wealth manager vs. DIY: similarities and the edge
• [34:17] How to raise grounded kids with wealth

Resources mentioned in this episode

• [50:08] Raised Healthy, Wealthy & Wise by Coventry Edwards-Pitt | Kindle and Paperback
• [50:08] Albion’s Seed by David Hackett Fischer | Kindle, Paperback, and Hardcover

[16:32] Apply to Long Angle, the trusted community for navigating wealth. Access member research, benchmarking reports, and curated investment opportunities while connecting with high-net-worth peers for authentic insights and relationships. Start your application at longangle.com.

About Tad Fallows

Tad Fallows is the Co-Founder and Managing Director of Long Angle, a private community for financially independent individuals and families. Long Angle provides a trusted space for members to connect, share insights, and learn from each other on topics ranging from investing and tax strategies to philanthropy, family governance, and personal fulfillment. Tad’s background includes building and leading businesses in the technology and financial sectors, with a focus on creating platforms that foster collaboration and knowledge sharing among high-net-worth families.

Connect with Tad

• Website: Long Angle
• LinkedIn: Tad Fallows | Long Angle

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

Former nurse leader Savannah Arroyo reveals how she jumped from running orthopedic practices to running multimillion-dollar real estate syndications, while raising two kids. Hear how COVID lit the fuse, why she structures 506(b) deals to include non-accredited nurses, the conservative playbook behind multiple full-cycle wins, and her assisted-living thesis that fuses clinical insight with cash-flowing operations. So, better tune in now!

Key takeaways to listen for

• [03:47] The moment Savannah pivoted from hospital leadership to building multiple income streams
• [06:35] Why she launched Net Worth Nurse during COVID to fix the financial literacy gap in healthcare
• [15:46] Why Savannah raises are 506(b) so unaccredited nurses can participate
• [28:40] A full-cycle case study: 24-unit Oregon turnaround
• [33:12] Fixed-debt rule that protected LPs when rates spiked

Resources mentioned in this episode

• [18:55] Passive Profits by Savannah Arroyo | Kindle and Paperback
• [41:49] Think and Grow Rich by Napoleon Hill | Kindle, Paperback, and Hardcover
• [41:49] Flow by Mihaly Csikszentmihalyi| Paperback

About Savannah Arroyo

Savannah Arroyo, known as the Networth Nurse, is a former healthcare administrator turned real estate investor and the founder of Willow Investment Group. She built a multimillion-dollar real estate portfolio while working full-time and raising two young children, proving that financial freedom is possible without quitting your job. Savannah specializes in syndications and has led investments in multifamily and assisted living assets across multiple markets. Through Networth Nurse, she empowers medical professionals and busy working parents to grow generational wealth through passive investing, education, and mindset transformation.

Connect with Savannah

• Website: Networth Nurse | Willow Investment Group
• Instagram: @networthnurse
• LinkedIn: Savannah Arroyo, MSN, RN
• YouTube: Networth Nurse

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

Tech founder turned LP, Pascal Wagner, breaks down a no-nonsense framework for evaluating sponsors, reading loan tapes, and building an LP pipeline that actually compounds. From “business-casual” relationship building on LinkedIn to why transparency beats glossy decks, he shows physicians and busy pros how to underwrite people first, structure cash reserves, and avoid shiny-object mistakes. So, better tune in!

Key takeaways to listen for

• [05:40] Why relationships beat ads for sourcing deals
• [13:40] The transparency test that reveals red flags instantly
• [20:55] How to skim a loan tape to spot risk fast
• [33:19] Must-have diligence docs every operator should share
• [44:18] Portfolio guardrails to cap per-deal exposure

Resources mentioned in this episode

• [03:30] Techstars
• [05:40] Gobundance
• [24:10] DLP Capital
• [46:52] The Hands-Off Investor by Brian Burke | Paperback and Kindle

[48:15] Get Pascal’s Passive Investing Starter Kit, a free LP toolkit at growyourcashflow.io. Designed for high-income professionals, it shows you how to turn a volatile stock portfolio into predictable cash flow with the right education, systems, and investments. Start building six figures in passive income today!

About Pascal Wagner

Pascal Wagner is a Techstars-backed entrepreneur, a limited partner in real estate, and the founder of Grow Your Cash Flow. He created the Passive Investing Starter Kit to help busy professionals confidently evaluate syndication deals and sponsors, analyze debt structures, and build a consistent pipeline of passive investments. Pascal hosts the Best Ever Passive Income Playbook, where he interviews top LPs and GPs to uncover strategies for building long-term wealth. With a background in tech startups and a data-driven approach to investing, he empowers others to achieve financial freedom without sacrificing their time.

Connect with Pascal

• Website: Grow Your Cashflow
• Podcast: The Passive Income Playbook | Apple Podcasts and Spotify
• Instagram: @pascalwagner
• LinkedIn: Pascal Wagner
• YouTube: The Grow Your Cashflow Podcast

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here