Épisodes

  • 151 | The Future of Tax Strategy: AI, the IRS, and What Entrepreneurs Need to Know

    151 | The Future of Tax Strategy: AI, the IRS, and What Entrepreneurs Need to Know
    Sep 29 2026

    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
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    52 min
  • 152 | The Exit Plan Nobody Tells You About with Sarah Friedell O'Connell

    152 | The Exit Plan Nobody Tells You About with Sarah Friedell O'Connell
    Oct 6 2026
    Why do 75% of business owners who successfully sell their company feel profound regret within the first year? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Sarah Friedell O'Connell, founder and president of ChangePoint Advisors, to unpack the side of exit planning most entrepreneurs never prepare for: life after the sale. Sarah is a certified retirement coach and executive transition coach, a former Fidelity Investments executive, and a former spokeswoman for the president of Harvard University. She has guided hundreds of business owners and senior executives through one of life's most stressful transitions. Together, Patrick and Sarah explore why selling a business or retiring can leave even financially secure entrepreneurs without identity, purpose, and connection, and what to do about it before the deal closes. Whether you're five years from exiting your business or just starting to think about succession planning, this conversation offers a practical roadmap for a fulfilling next chapter. Sarah walks through the four phases of retirement and how to skip the painful one. She explains why your spouse needs to be part of your exit strategy from day one, and why turning a hobby into a business often backfires. Patrick shares Vital Wealth's REACH framework for building wealth around what matters most, and Sarah closes with a simple self-reflection exercise any entrepreneur can start today. If you're building wealth with an eventual exit in mind, this episode will help you make sure your life is as ready as your balance sheet. Key Takeaways Exit planning has three legs: business, financial, and personal. The personal plan is the one most often ignored.Post-sale regret rarely comes from the deal terms. It comes from losing identity, purpose, structure, and community.Retirement ranks among the top 10 most stressful life events, alongside divorce and the death of a loved one.Most people move through four phases after they stop working: vacation, loss, experimentation, and a new life. With a plan, you can skip the loss phase.Bring your spouse into the conversation early. Mismatched expectations are part of why "gray divorce" is rising among people over 50.Test new pursuits in small ways before committing. Don't buy the gym just because you love working out.A life planner should be at the table alongside your financial and tax advisors, ideally about five years before an exit.Start now: audit how you spend your time, notice what energizes you, and invest in your life outside the business. Learn More About Sarah: ChangePoint Advisors: changepointadvisors.comSarah's email: sarah@changepointadvisors.comSarah Friedell O'Connell on LinkedIn: Sarah Friedell O'Connell | LinkedIn Books: From Strength to Strength by Arthur C. BrooksDesigning Your Life by Bill Burnett and Dave EvansDie With Zero by Bill PerkinsThe Good Life by Robert Waldinger and Marc SchulzThe Monk and the Riddle by Randy KomisarWild at Heart by John EldredgeTransitions by William BridgesHappier Hour by Cassie Holmes Resources: Visit vitalwealth.com/resources to download FREE resources Follow on Instagram at https://www.instagram.com/vitalwealthstrategiesFollow on Facebook at https://www.facebook.com/VitalStrategiesPodcastFollow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ Credits: Sponsored by Vital WealthMusic by CephasAudio, video, research and copywriting by Victoria O'Brien
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    1 h et 3 min
  • 153 | The Charitable Tax Mistake That Could Cost You Millions with Phoenix Hafen

    153 | The Charitable Tax Mistake That Could Cost You Millions with Phoenix Hafen
    Oct 13 2026

    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
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    46 min
  • 155 | The $500K Family Feud That Good Estate Planning Could Have Prevented with Lauren Klein

    155 | The $500K Family Feud That Good Estate Planning Could Have Prevented with Lauren Klein
    Oct 27 2026

    Does your will keep your family out of probate? For most entrepreneurs, the answer is no, and that misunderstanding can cost their families time, money, and privacy. On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Lauren A. Klein, Esq., LL.M., an estate planning and tax attorney, founder of Flourish Law Group, and adjunct law professor of wills and trusts. Pat and Lauren break down estate planning for entrepreneurs in plain language. They cover the foundational documents every adult needs, the difference between revocable and irrevocable trusts, and the trust-funding mistake Lauren calls the industry’s “dirty secret.” Pat also shares a personal story of a family that burned through roughly half a million dollars in legal fees because the hard conversations never happened.

    For business owners approaching an exit or building significant wealth, this episode is a masterclass in proactive estate tax planning. Lauren explains how moving business interests into an irrevocable trust before a liquidity event can keep future growth permanently outside the 40% federal estate tax. She also covers how valuation discounts and spousal lifetime access trusts (SLATs) work, and how to structure a trust so it builds wisdom in the next generation instead of entitlement. With the 2026 federal exemption at $15 million per person, and its future tied to politics, Pat and Lauren make the case that the best time to start planning is now. For more tools on tax strategy and wealth building, visit the resource vault at vitalwealth.com/resources, and submit your own questions for future episodes at vitalwealth.com/questions.

    Key Takeaways

    • A will does not avoid probate. Assets avoid probate only when they are titled to a trust, have a named beneficiary, or are held with a joint owner.
    • Every adult 18 and older needs a financial power of attorney and healthcare documents, and most entrepreneurs need at least a revocable trust.
    • Signing the trust is only step one. Assets must be retitled into it, or they can still go through probate.
    • Most people have three estate plans: the one they want, the one they think they have, and the one they actually have. Regular reviews bring them back into alignment.
    • In 2026, the federal estate and gift tax exemption is $15 million per person ($30 million per married couple), and the annual gift exclusion is $19,000 per recipient.
    • Moving business interests into an irrevocable trust before an exit can shift all future appreciation outside the taxable estate.
    • Valuation discounts for lack of control and lack of marketability can stretch your exemption further when supported by a qualified appraisal and a properly filed Form 709.
    • Couples creating SLATs for each other need meaningful differences between the two trusts to avoid the IRS reciprocal trust doctrine.
    • Equal is not always fair. Equalization clauses, letters of wishes, family constitutions, and corporate trustees help preserve both wealth and family relationships.
    • Lauren’s single best piece of advice is to just get started.

    Learn More About Lauren:

    • Flourish Law Group: flourishlawgroup.com
    • Lauren Klein on Instagram: instagram.com/lawyerlaurenklein
    • Lauren Klein on LinkedIn: Lauren A. Klein, Esq., LL.M. | LinkedIn

    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
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    1 h et 1 min
  • 154 | Your Business Isn't Worth What You Think It Is with David Barnett

    154 | Your Business Isn't Worth What You Think It Is with David Barnett
    Oct 20 2026
    Do you know what your business is actually worth to a buyer, or just what it’s worth to you? On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan welcomes back David C. Barnett, one of the show’s very first guests, to unpack one of the most important questions every entrepreneur eventually faces: “What is my business worth?” David is a business consultant, author, and equipment appraiser who has sold 36 businesses as a broker, spent years as a banker, and has advised on more than a thousand deals. In his new book, Business and Asset Values, he explains why business valuation is never a single number but a conclusion tied to a decision, and why owners, buyers, lenders, and advisors can all arrive at different, defensible answers for the same company. Patrick and David dig into why a business can be highly profitable for its current owner yet worth far less to the next one, what goodwill really means, how lenders evaluate a deal through debt service coverage and SBA guidelines, and how machinery and equipment values can shift overnight. David also shares what he calls the most lucrative exit strategy available to business owners, and the exact steps an entrepreneur should take today to position a company for a sale ten years from now. Whether you plan to sell, buy, or simply build a stronger and more transferable business, this conversation will change how you think about enterprise value and exit planning. For more tax strategy and wealth-building tools, explore the resource vault at vitalwealth.com/resources, and share the questions you want answered on future episodes at vitalwealth.com/questions. Key Takeaways: Value is a conclusion, not a number. What a business is worth depends on who is asking, for what purpose, and under what assumptions and terms.Buyers ask two questions. First, what is the demonstrable, provable cash flow? Second, will that cash flow continue under new ownership?Profitability is not transferability. A business that depends on its owner shrinks its pool of buyers and lowers its price.Goodwill has to be proven. Real goodwill shows up as higher margins than competitors, not as years of history or a well-known name.Volatile businesses shouldn’t carry debt. Lumpy, project-based cash flow usually calls for equity, seller financing, or staged transactions instead.Lenders look for strong debt service coverage. 1.25x is the minimum, many banks want 1.5x, and David prefers 2.0x for smaller Main Street deals.Four of the top five reasons owners sell are unplanned. Burnout, divorce, and poor health rank ahead of retirement, so being sale-ready protects your options.The most lucrative exit is retiring to ownership. Build the systems, team, and reporting so the business runs without you while you keep the cash flow.Exit tax planning takes years. Many strategies to reduce tax on a sale require multiple years of advance preparation. Learn More About David: Business and Asset Values: How Owners, Buyers, Sellers, Lenders and Advisors Should Think About Small Business and Equipment Value: Amazon.com: Business and Asset Values: How Owners, Buyers, Sellers, Lenders, and Advisors Should Think About Small Business & Equipment Value eBook : Barnett, David: Kindle StoreDavid YouTube channel: David C Barnett Small Biz and Deal Making Channel IntroDavid’s website: BookDavidCBarnett.com - BookDavidCBarnett.com Resources: Visit vitalwealth.com/resources to download FREE resources Follow on Instagram at https://www.instagram.com/vitalwealthstrategiesFollow on Facebook at https://www.facebook.com/VitalStrategiesPodcastFollow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ Credits: Sponsored by Vital WealthMusic by CephasAudio, video, research and copywriting by Victoria O'Brien
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    1 h et 12 min
  • 139 | How to a Build a Sales Team so the Business can Scale with Mike Huey

    139 | How to a Build a Sales Team so the Business can Scale with Mike Huey
    Jul 7 2026
    Are you still the most important person in your sales process? For most entrepreneurs, the honest answer is yes and it's the single biggest thing capping their revenue, their company's value, and their freedom. In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Mike Huey, founder of Scalable Sales Solutions and a sales veteran with 30 years of experience building, breaking, and rebuilding sales organizations from coast to coast. Mike has taken companies from founder-led sales to national scale, including growing a seven-employee facility services business into a nationwide operation and today he helps business owners get the sales hat off so they can build something that runs, grows, and eventually sells without them. Patrick and Mike dig into the exact system that attracts A-player salespeople (and why hiring from inside your own industry almost guarantees you a B or C player), the compensation structures that actually drive new business instead of rewarding the wrong behavior, and the five sales metrics every owner should be tracking. They also cover the recruiting trick Mike uses to screen hundreds of applicants down to true A players, why you have to be willing to fire your top performer over a values violation, and how to know when your business is truly ready to scale or sell. Whether you're stuck as the bottleneck in your own company or preparing for an exit in the next five years, this conversation is a blueprint for turning a personality-driven business into a transferable asset. Key Takeaways: If your business can't grow without you personally closing every deal, you own a high-paying job, not a transferable assetA-player salespeople are attracted by five things: a sales playbook, a lead generation system, a CRM everyone uses, scorecards and accountability, and a compensation plan that rewards the right activitiesHiring salespeople from within your own industry usually lands you B and C players, true A players won't leave a strong book of businessCompensation plans should adjust every year; stairstep and hurdle models push reps toward new accounts, new territories, and new productsTrack five metrics: sales activity, average deal size, close rate, repeat purchase rate, and referral rateCulture comes down to two things, the right scorecards and core values and you must be willing to fire top performers over value violationsA business is only ready to scale when it cash flows completely with the owner stepped out of the processStart exit planning long before the emergency: "life after the business" is one of the biggest reasons deals fall apartThis week's action step: identify the two or three things you're doing that hold the company back, and build a plan to offload them Learn More About Mike: Mike Huey's website / consultation: mikehuey.comLeadership Blueprint: Accountability in Action by Mike HueyThe Art of War for Business by Mike HueyMake Your Company Scalable and Saleable by Mike Huey Resources: Visit vitalstrategies.com to download FREE resources Listen to the podcast on your favorite app: Vital Wealth Strategies Podcast | Tax & Financial Strategies for EntrepreneursFollow on Instagram at https://www.instagram.com/vital.strategiesFollow on Facebook at https://www.facebook.com/VitalStrategiesPodcastFollow on LinkedIn at https://www.linkedin.com/in/patricklonergan/ Credits: Sponsored by Vital WealthMusic by CephasArt work by Two Tone Creative Audio, video, research and copywriting by Victoria O'Brien
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    54 min
  • 140 | Business Fuel: How to Find the Right Capital for Every Stage of Growth with Levi King

    140 | Business Fuel: How to Find the Right Capital for Every Stage of Growth with Levi King
    Jul 14 2026

    What does it actually take to get a business loan and why are so many successful entrepreneurs getting denied? In this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Levi King, co-founder of Nav and one of the foremost experts on small business credit and financing in the country. Levi brings a rare combination of real-world experience, having started five businesses, secured over forty commercial loans across multiple industries, and built Lendio, the nation's largest commercial loan broker and the technical depth of a fintech founder who has spent a decade solving the financing gap for millions of small business owners. This conversation goes far beyond the basics and delivers a masterclass on what lenders are actually looking at, why most entrepreneurs are flying blind, and what to do about it.

    Patrick and Levi unpack why business credit and personal credit operate by entirely different rules, how a single bounced check can quietly disqualify an otherwise strong borrower, and why the way a business is structured legally can make or break a loan application before it ever reaches an underwriter. With credit markets expected to tighten in the months ahead, Levi makes a compelling case for why right now, not when you need capital, is the time to build your financial foundation. Whether you are actively seeking financing or simply want to be prepared when the opportunity arises, this episode will change the way you think about capital, credit, and the financial infrastructure of your business.

    Key Takeaways:

    • Business credit and personal credit are completely different, low data consistency across commercial bureaus means a strong D&B score does not guarantee strong Experian or Equifax scores
    • The Fair Credit Reporting Act does not apply to business credit, disputes move slower and protections are weaker
    • Bounced checks are one of the most common and costly mistakes, even three per month can disqualify an otherwise strong borrower from many lenders
    • Lenders use AI and trending deposit data to determine whether a business is growing or quietly in distress
    • Sole proprietors face significant financing disadvantages, forming a legal entity is critical for access to business loans and credit cards
    • Mixing personal and business finances is an automatic decline with most lenders
    • Get a line of credit before you need one, in a tightening credit cycle, existing facilities stay active longer than new approvals get through
    • Nav aggregates personal credit, all three commercial bureau data sets, and cash flow data via Plaid to show business owners exactly how a lender sees them
    • The best time to build your financial profile is before you need capital, subprime emergency loans often accelerate business failure rather than prevent it
    • Customer revenue is always the best capital, financing should be a growth lever, not a lifeline

    Learn More About Levi:

    • Nav platform: nav.com

    Resources:

    • Visit vitalwealth.com/resources to download FREE resources
    • 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
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    46 min
  • 141 | The investing Lesson Every Entrepreneur Learns the Hard Way with Andrew Horowitz

    141 | The investing Lesson Every Entrepreneur Learns the Hard Way with Andrew Horowitz
    Jul 21 2026

    What happens to an entrepreneur's wealth the day they finally step back from the business they spent decades building? On this episode of the Vital Wealth Strategies Podcast, host Patrick Lonergan sits down with Andrew Horowitz, a nearly 40-year veteran of the financial services industry and host of The Disciplined Investor podcast, to break down why so many successful business owners struggle to invest their wealth with the same discipline they used to build their company.

    Horowitz and Lonergan dig into why an entrepreneur's own business behaves like one of the riskiest assets in their portfolio, the real math behind a market drawdown, and a practical dollar-cost-averaging strategy called "one foot in, one foot out" that helps investors get off the sidelines without the fear of a lump-sum decision gone wrong. Whether an entrepreneur is still building free cash flow inside the business or preparing for a future liquidity event, this conversation lays out a clear framework for separating business risk from investment risk, building an all-weather portfolio, and making decisions based on process instead of emotion.

    Key Takeaways:

    • Why business owners often confuse business success with investing skill, and why that gap creates unnecessary risk
    • How a founder's business behaves like a micro-cap stock, exposed to shocks that can undo years of hard work
    • The real math behind a drawdown: why a 50% loss requires a 100% gain just to break even
    • The psychology of a liquidity event, and why mark-to-market investing feels different than watching a home value rise
    • The "all-weather portfolio" (or "flower garden") approach to true diversification
    • The "one foot in, one foot out" dollar-cost-averaging strategy for investing without the fear of bad timing
    • Why waiting for a market pullback can end up costing more than staying invested
    • How to separate business risk from investment risk after selling or exiting a company

    Learn More About Andrew:

    • The Disciplined Investor podcast / Andrew Horowitz
    • DH Unplugged podcast (Andrew Horowitz & John C. Dvorak)

    Resources:

    • Visit vitalwealth.com/resources to download FREE resources
    • 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
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    51 min