Is your business exit on the horizon, and have you already decided that some of your wealth will one day go to causes you care about? On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan, founder of Vital Wealth and advisor to high-level entrepreneurs, sits down with Phoenix Hafen, Director of Advisor Solutions at UI Charitable. UI Charitable manages more than $550 million in donor-advised funds for high-net-worth individuals and families. Together they break down why cash is the least tax-efficient asset you can give, and how entrepreneurs can donate appreciated stock, private business interests, real estate, and even venture fund stakes to a donor-advised fund to avoid capital gains tax and capture a charitable deduction.

Pat and Phoenix walk through the real mechanics of charitable planning before a liquidity event. They cover why the IRS wants the deal “still at risk” when you give, how qualified appraisals work, the AGI deduction limits that can catch donors off guard, and when a private foundation makes more sense than a donor-advised fund. Phoenix also shares a creative example of a venture investor who turned illiquid LP interests into a charitable deduction, and he explains how families use donor-advised funds to bring the next generation into philanthropy. If you’re charitably minded and expecting a significant sale in the next few years, this episode shows you how to give more intentionally and more tax-efficiently. For more on tax strategy and wealth building, visit vitalwealth.com/resources, and send your own questions for future episodes to vitalwealth.com/questions.

Key Takeaways

• Never donate cash. Appreciated assets with large capital gains are usually the most tax-efficient gifts.
• Donate appreciated stock and use the cash you would have given to buy it back. You keep your exposure and reset your cost basis.
• Almost anything that can be appraised can go into a donor-advised fund, including private business interests, real estate, precious metals, and LP interests.
• Give before the sale, not after. The IRS wants the deal to still be at risk when you make the gift.
• For a charitable gift, you want the appraisal as high as possible, the opposite of estate planning, where you often seek discounts.
• AGI limits apply to charitable deductions, but unused deductions can carry forward up to five years.
• A donor-advised fund fits most donors. A private foundation is mainly needed to pay staff or give grants directly to individuals.
• Measure charitable impact by outcomes, not outputs.

Resources to Link

• UI Charitable: uicharitable.org

Resources:

• Visit vitalwealth.com/resources to download FREE resources
• Follow on Instagram at https://www.instagram.com/vitalwealthstrategies
• Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast
• Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/

Credits:

• Sponsored by Vital Wealth
• Music by Cephas
• Audio, video, research and copywriting by Victoria O'Brien

What if the very thing you've spent your career trying to eliminate, discomfort, is actually the thing driving your growth? On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Darshan "Dave" Patel, co-founder of BuildRite, a healthcare billing company he has run alongside his business partner Soren for nearly three decades. Dave's story starts in a lower middle class household in India, where he repeated two grades in school before finding his footing not in a classroom, but with his hands, fixing broken equipment in his father's small service business. That early spark set off a winding path through Canada, several failed and successful ventures in Florida, and eventually a company built on client trust that grew into an international, India-based team.

Throughout the conversation, Dave and Patrick unpack what it really takes to build a business that lasts two decades and beyond. They dig into how Dave and Soren figured out scaling without a playbook, why they brought in outside consultants even when results were strong, and the real distinction between outsourcing work overseas versus building a genuinely owned and operated team abroad. Dave also opens up about raising financially secure kids without raising entitled ones, why he intentionally spent a month living without air conditioning in India with his entire family, and what he believes AI means for the next generation of entrepreneurs and their sense of purpose. Entrepreneurs looking to scale past themselves, build international teams the right way, or simply rethink their relationship with comfort will find plenty to take away from this episode.

Key Takeaways:

• Growth often requires choosing discomfort on purpose rather than optimizing for ease
• Scaling a business means shifting from being "in" the business to being "on" the business
• Building an owned team overseas is fundamentally different from simply outsourcing work
• Bringing in outside consultants, even during success, can reveal blind spots founders can't see themselves
• Raising financially secure kids requires intentional boundaries to avoid entitlement
• AI is changing the value of traditional education, making purpose more important than credentials
• Long-term business partnerships thrive on radical, no-sugarcoating communication

Credits:

• Sponsored by Vital Wealth
• Music by Cephas
• Audio, video, research and copywriting by Victoria O'Brien

Should entrepreneurs trust AI with their tax strategy, or is that a risk too big to take? On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Ricky Lavigna, a CPA and the founder of TaxFyle, to separate the hype from the reality of AI in tax filing. Lavigna started his career at PricewaterhouseCoopers before founding TaxFyle in 2015, and today serves on the IRS's Electronic Tax Administration Advisory Committee (ETAC), giving him a rare, inside perspective on how both the private sector and the federal government are approaching the future of tax technology.

Throughout the conversation, Lonergan and Lavigna dig into what AI can realistically do for tax preparation today, why human accountability remains essential even as accuracy improves, and how the IRS itself is deploying AI to close a tax gap worth tens of billions of dollars. The episode also tackles the difference between legitimate tax strategy and the kind of aggressive tax gimmicks that can land entrepreneurs in serious trouble, along with a practical framework for thinking through which tax moves require IRS guidance versus real investment versus sophisticated entity structuring. Entrepreneurs and financial advisors alike will walk away with a sharper understanding of where AI genuinely adds value in tax planning, and where it falls dangerously short.

Key Takeaways:

• AI is highly accurate at document reading, calculations, and data aggregation, but remains fundamentally predictive in nature and cannot be wholly relied upon for tax filing decisions
• The IRS's known tax gap sits at roughly $90 billion or more, and the agency is leaning on AI to reconcile 1099s and flag discrepancies amid staffing shortages
• Accountability, meaning a licensed professional with "skin in the game," remains the key differentiator between AI-assisted tax prep and simply outsourcing to AI or offshore labor
• Tax strategy exists on a spectrum: from IRS-guided moves requiring no investment (like optimizing the QBI deduction), to moves requiring capital (401(k)s, SEP IRAs, cash balance plans), to advanced strategies that combine multiple sections of the tax code
• Documentation is increasingly critical as AI makes it easier for the IRS to flag returns for review, particularly around gray-area claims like real estate professional status
• The line between smart tax strategy and tax gimmicks matters, since not every deduction an AI surfaces is one an entrepreneur should actually take
• Financial advisory and tax preparation are converging, as entrepreneurs increasingly want one trusted partner managing tax, investment, and wealth strategy together

Learn More About Ricky:

• TaxFyle

Resources:

• Visit vitalwealth.com/resources to download FREE resources
• Follow on Instagram at https://www.instagram.com/vitalwealthstrategies
• Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast
• Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/

Credits:

• Sponsored by Vital Wealth
• Music by Cephas
• Audio, video, research and copywriting by Victoria O'Brien

What if the same Airbnb everyone scrolls past on vacation could be the reason your next tax bill drops by six figures? On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Nick Korom, CEO of MyBnBAccelerator.com, to break down exactly how entrepreneurs are using short-term rentals to legally slash their tax liability without becoming a full-time real estate professional. Nick has helped close over 500 short-term rental properties for more than 300 clients, and in this conversation he pulls back the curtain on the strategy, the numbers, and the mistakes that turn a promising deal into a costly one.

Patrick and Nick walk through the mechanics of the short-term rental loophole, how a cost segregation study can accelerate hundreds of thousands of dollars in depreciation into year one, and the three non-negotiables - market, property type, and design, that separate a cash-flowing investment from a regretted purchase. Listeners will also hear real underwriting numbers, which markets are quietly heating back up, and the red flags that should make any investor walk away from a deal. Whether you're actively building a real estate portfolio or just tired of watching your tax bill climb every year, this episode lays out a clear, actionable framework for turning real estate into one of the most powerful wealth-building and tax-saving tools available to entrepreneurs.

Key Takeaways:

• The short-term rental loophole lets entrepreneurs unlock major tax benefits without qualifying as a full-time real estate professional (no 750-hour requirement)
• A cost segregation study can accelerate a large percentage of a property's value into year-one depreciation, creating significant upfront tax savings
• Success in short-term rentals comes down to three factors: the right market, the right property type, and the right design and design is the most commonly underestimated
• Target underwriting benchmarks include 8–15% cash-on-cash return and 50%+ ROI on tax savings
• Foundation issues are the number one reason deals get killed during inspection
• Not every market or every entrepreneur is a fit, this strategy works best for high income earners with liquidity and a longer-term investment mindset
• Local design and property management teams consistently outperform large national firms on quality and attention to detail

Resources Mentioned:

• MyBnBAccelerator.com Nick Korom's short-term rental investment company
• AirDNA short-term rental market data and analytics
• Rabbu short-term rental data and underwriting tool
• Mashvisor real estate and STR market data platform
• Furnished Finder medium-term rental platform
• Padsplit medium-term/room rental platform
• Purple Cow by Seth Godin

Resources:

• Visit vitalwealth.com/resources to download FREE resources

Credits:

• Sponsored by Vital Wealth
• Music by Cephas
• Audio, video, research and copywriting by Victoria O'Brien

What if the best real estate deal in Europe cost a fraction of what the same property would run in Sedona or Santa Barbara? On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Mike Stohler of Gateway Private Equity to unpack why he's moving beyond the traditional US real estate playbook and into international hotel investing, specifically historic boutique properties in Spain. Stohler shares his journey from financing his first units on a credit card in the pre-Google era to building a portfolio that spans multifamily, senior housing, and hotels across the US and Europe.

Throughout the conversation, Stohler breaks down exactly what separates a hotel from a typical real estate investment, why it functions as both a business and an asset, and what that means for financing, tax treatment, and long-term returns. He and Lonergan dig into the due diligence mistakes that sink deals, the surprising economics behind buying a centuries-old Spanish property for a fraction of its US equivalent, and how currency diversification, favorable interest rates, and cross-border tax treaties are reshaping how entrepreneurs think about protecting and growing their wealth outside the United States. For entrepreneurs sitting on free cash flow and looking for a way to diversify beyond the usual multifamily deal or stock portfolio, this episode offers a rare look at an opportunity most investors have never considered.

Key Takeaways:

• A hotel is not just real estate. It's an operating business layered on top of real estate, which changes financing options, tax treatment, and risk profile.
• Post-COVID, the strongest hotel investments have at least three independent demand drivers rather than relying on a single source of traffic.
• Reconciling a property's P&L against its actual tax returns is one of the most overlooked and most important due diligence steps in any real estate acquisition.
• Historic boutique hotels in Spain can be acquired for a fraction of the cost of comparable properties in the US, with favorable financing rates and a US-Spain tax treaty that prevents double taxation.
• International real estate offers entrepreneurs a way to diversify their wealth outside typical US concentration risk while gaining a genuine lifestyle benefit.
• Choosing the right due diligence team, including local expertise, is essential when investing in an unfamiliar market.

Learn More About Mike:

• Gateway Private Equity: gatewaype.com
• International Opportunity: https://gatewaype.portal.agorareal.com/#/public/brochure/1/efe09f68-c50c-4526-b729-06a94715c665

Resources:

• Visit vitalwealth.com/resources to download FREE resources

Credits:

• Sponsored by Vital Wealth
• Music by Cephas
• Audio, video, research and copywriting by Victoria O'Brien

What happens when a "genius" tax write-off you saw on TikTok turns out to be the same strategy that landed two professionals in federal prison for over 20 years each? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with colleague Michael to unpack the difference between smart, compliant tax strategy and the sham strategies that can trigger IRS penalties, audits, or worse. From viral myths about writing off G-Wagons and vacation homes to real-world fraud cases involving KPMG, syndicated conservation easements, and abusive trust structures, this conversation separates the tax moves that build real wealth from the ones that build a case file.

Pat and Michael break down five of the most common tax "myths" circulating online today, explain what actually makes a deduction legitimate under the IRS's own rules, and walk through several high-profile case studies where aggressive tax planning crossed the line into fraud. Entrepreneurs making seven figures or more will walk away with a practical framework for evaluating any tax strategy before they implement it, including the exact questions to ask an advisor and the red flags that separate a smart move from a dangerous one. Whether you're considering a cost segregation study, putting your kids on payroll, or wondering if an S-election makes sense for your business, this episode gives you the guardrails to pursue aggressive tax savings without putting your business, or your freedom, at risk.

Key Takeaways:

• Why "it's a write-off" doesn't mean it's free, and how the math on tax deductions actually works
• The truth about writing off vehicles over 6,000 lbs, and why depreciation recapture can undo the benefit
• How cost segregation studies really work, and what's required to use the deduction against active income
• The right and wrong way to put your kids on payroll for tax savings
• Why not every entrepreneur should rush to file an S-election
• Real case studies: the KPMG tax shelter scandal, syndicated conservation easement fraud, and abusive trust schemes
• The critical difference between tax avoidance and tax evasion
• A five-question framework for vetting any tax strategy before you implement it

Resources:

• Visit vitalstrategies.com to download FREE resources
• Listen to the podcast on your favorite app: Vital Wealth Strategies Podcast | Tax & Financial Strategies for Entrepreneurs
• Follow on Instagram at https://www.instagram.com/vital.strategies
• Follow on Facebook at https://www.facebook.com/VitalStrategiesPodcast
• Follow on LinkedIn at https://www.linkedin.com/in/patricklonergan/

Credits:

• Sponsored by Vital Wealth
• Music by Cephas
• Art work by Two Tone Creative
• Audio, video, research and copywriting by Victoria O'Brien