Why do 80% of business owners regret their exit within a year?

In this episode, Joe LoPresti, founder of Arlington Wealth Management, shares why success doesn’t always equal freedom — and the $2 million mistake that keeps many entrepreneurs stuck. 

Joe introduces the "Freedom Point" concept—a framework encompassing financial, time, relationship, and purpose freedom that goes beyond traditional retirement math. He also reveals how fragmented advisor relationships have cost business owners millions and why coordinated planning is essential.

Key topics include three critical exit mistakes, why revenue growth provides marginal returns compared to optimizing enterprise value, and why one-third of business exits are unplanned. Joe discusses building a coordinated advisory team that functions as your "personal Chief Financial Officer."

🎧 Listen now to learn how to design your exit strategy that protects your wealth—and secures your freedom. 

“What happens if you’re not here tomorrow?”

In this eye-opening episode, Joe LoPresti reveals how one question can stop a business sale in its tracks—and why even profitable companies often fail the tests buyers truly care about.

Joe unpacks four hidden deal-breakers, the Freedom Point calculation most owners miss, and how siloed advisors quietly erode your business’s sellability.

🎧 Listen now to discover what you can start fixing this week to build real exit value—before it’s too late.

Joe LoPresti, founder of ClearPoint Family Office and Arlington Wealth Management, joins M&A Masters to explore why even successful business owners often feel unprepared during the final stages of an exit. He discusses how siloed advice can lead to costly gaps, and why coordinated planning is essential.

Joe introduces the “Sully Principle,” the “red zone” of exits, and how fractional family offices provide elite-level support without the overhead. He also covers how rep and warranty insurance is now accessible for smaller deals—and the one question that reveals major blind spots in exit strategies.

🎧 Listen now to learn how to exit on your terms and avoid costly mistakes.

In this episode of Behind Their Success, Joe LoPresti, founder of Arlington Wealth Management, joins host Paden Squires to discuss why many successful entrepreneurs struggle to transition from business ownership to lasting financial freedom.

Joe breaks down the “20-yard line problem” and shares how having a “personal CFO” can bring your accountant, attorney, and financial advisor together—finally getting everyone aligned around what really matters to the owner. He also talks about how starting early can open up more exit options and how clarity often leads owners to keep their business—once they’ve achieved the freedom they were seeking.

🎧 Listen now to learn how aligned advice helps avoid costly mistakes during life’s biggest transition.

In this episode of Master Your Millions, Joe Lopresti, founder of Arlington Wealth Management, reveals why 80% of business owners regret their exit—often within a year. It’s not bad timing or market forces—it’s a lack of awareness around critical strategies they never knew existed.

Joe dives into key topics, including the 3 “soft factors” buyers prioritize beyond financials, how to define your Freedom Point, why a 2–5 year runway is essential, and how fractional family offices eliminate the pitfalls of conflicting advice.

🎧 Listen now to learn how to take control of your exit—and your future—with intention and clarity.

In this episode of M&A Talk, Joe Lopresti, founder of Arlington Wealth Management, dives into the top reasons business owners often walk away from their exit with regret. Drawing from decades of experience, Joe outlines four common mistakes—like failing to define a clear Freedom Point, underestimating planning complexity, misunderstanding buyer valuation, and relying on siloed advice.

Jacob shares a real-world example of how uncoordinated guidance nearly cost him during his own exit planning, underscoring the need for a fully integrated advisory team.

🎧 Listen now to discover how to avoid costly missteps and create a more confident, regret-free transition.

In this insightful episode of the Financial Survival Network, Joe LoPresti, founder of Arlington Wealth Management, shares proven strategies to help business owners plan and execute successful exits. Drawing from over 40 years of experience advising entrepreneurs, Joe explains why most business transitions fall short—and how to avoid the common pitfalls that lead to regret.

He explores three critical areas every owner must address: clarifying your next act, identifying your freedom point, and understanding the true market value drivers of your business. Joe also outlines various exit paths, from management transitions to private equity sales, and emphasizes the importance of designing your exit intentionally—not by default.

🎧 Tune in now to learn how to maximize your business’s value and transition into your next chapter with confidence and clarity.

In this powerful episode of The Exit Plan podcast, Joe LoPresti shares hard-won insights from his 40+ years guiding business owners through high-stakes transitions. Joe dives into a critical but often overlooked issue: the “dumb tax” entrepreneurs pay when they don’t fully understand the tax, legal, and financial strategies available during a business exit.

He introduces the concept of the Freedom Point—the financial threshold where business owners can live life on their terms—and explains why most entrepreneurs struggle to reach it. From assessing your business’s true sellability to designing a Lifetime Cash Flow Plan, Joe discusses how to align your business and personal financial planning to avoid regret and maximize value.

Whether you’re planning an exit or just starting to think about it, this episode is packed with actionable advice for protecting the wealth you've worked so hard to build.

Joseph LoPresti recently appeared on The Richer Geek podcast with host Michael Stohler, sharing critical insights about financial opportunities that many business owners overlook. Drawing from his 39 years of experience in financial services, Joe discussed how proper financial guidance can help business owners identify and capitalize on significant savings opportunities.

Key Topics Covered:

• Why many business owners miss crucial financial opportunities
• The impact of having coordinated financial guidance
• How timing affects wealth-building potential
• Real examples of substantial savings through proper financial planning

The discussion offers valuable guidance for entrepreneurs seeking to maximize both their business and personal wealth. Joe shares concrete examples, including how one business owner discovered $80,000 in annual savings opportunities through professional financial guidance.

This conversation provides actionable insights for business owners at any stage of their journey, whether they're growing their business or planning their eventual exit.

To listen to the full episode and gain deeper insights into maximizing your business's financial potential, click the button below.

Joseph LoPresti recently appeared on "Get Down To Business" with Scott "Shalom" Klein to discuss a critical challenge facing business owners: the hidden costs of uncoordinated advice. Drawing from his wealth management and business consulting experience, Joe shared insights on how breaking down advisory silos can lead to more successful business transitions.

The podcast episode explores why traditional fragmented advisory approaches often fall short for business owners. Joe shares expert insights on several crucial topics, including:

• The Siloed Advisory Challenge: Why having multiple expert advisors isn't enough if they're not working together.
• The Personal Action Plan: Creating a comprehensive framework that considers:
  • Business readiness: Maximize your company's value before transition.
  • Owner readiness: Ensure you're financially and emotionally prepared.
  • Business attractiveness: Structure your business to attract premium offers.
  • Employee treatment: Maintain team stability through the transition.
  • Post-sale planning: Design your ideal lifestyle after the sale.
• The Freedom Point: Understanding the financial milestone that allows business owners to live life on their terms
• The Generational Shift: How newer business owners are approaching exit planning differently than their predecessors

This discussion offers valuable guidance for business owners at any stage of their journey. Joe emphasizes the importance of coordinated planning, stating, "The business is going to sell based on the readiness of the business to transition, the readiness of the owner to transition, and the attractiveness of the business—not the way the owner looks at it, but the way a potential buyer looks at it."

Listen to the full episode and gain deeper insights into successful business exit strategies.

Joe recently appeared on Exit Strategies Radio Show to share crucial insights about what drives business owners: the desire for freedom. As founder of Arlington Wealth Management with 25 years of experience, Joe revealed how business owners can coordinate their wealth planning with business strategy to achieve true freedom.

In this enlightening conversation, Joe explains:

• Why freedom encompasses relationships, purpose, and financial independence.
• The "Freedom Point" - when you've accumulated enough wealth to do whatever you want, whenever you want.
• Why siloed professional advice from accountants, attorneys, and financial advisors can miss opportunities.
• The "dumb tax" - the cost of what you don't know when planning your exit.
• How do you design your exit before circumstances force one upon you?

Joe shares, "Most owners value personal freedom above all else," and explains how understanding your Freedom Point changes how you make crucial business decisions.

Listen to the full episode to learn how to design your exit on your own terms.

Joseph LoPresti, founder of Arlington Wealth Management and author of "Exit by Design," was recently featured on The Profit Accelerator Podcast. In this insightful interview, Joe discusses the critical role of a personal Chief Financial Officer (CFO) for business owners.

Key Topics Covered:

• The limitations of traditional, siloed financial advice for business owners
• How a personal CFO coordinates business and personal financial strategies
• The concept of the "dumb tax" and its impact on business exits
• Ideal timing for engaging a personal CFO
• Arlington Wealth Management's unique "virtual family office" approach

Joe shares his expertise on why a personal CFO is crucial for business owners, especially those approaching age 55 or considering an exit in the coming years. He explains that a personal CFO does more than just manage income or investments; they combine all aspects of a business owner's financial life, including tax planning, business strategy, risk mitigation, legal needs, and estate strategies.

This interview offers valuable insights for business owners looking to maximize their potential and ensure all aspects of their financial life are working together effectively. Joe's practical advice and real-world experience shine through as he discusses the importance of proactive financial planning.

Listen to the full episode to learn how a personal CFO could transform your approach to wealth management and business strategy.

Recently, Joe had the privilege of joining Gary Wilson on the Massive Passive Cashflow podcast. They explored the crucial topic of "Designing Your Perfect Business Exit," drawing from Joe’s experience in wealth management and business consulting.

The podcast episode sheds light on the intricacies of a fulfilling exit strategy, discussing why many owners feel unprepared for this significant transition. Joe shares expert insights on proactive planning, including developing a personal action plan, optimizing your business for sale, and the importance of collaborative advisory teams.

Key topics covered include:

• The concept of the "Freedom Point" and its importance in planning
• Understanding and improving your business's sellability score
• The role of a Personal Chief Financial Officer in coordinating your key decisions
• How a Virtual Family Office can provide creative financial solutions
• The importance of pre-sale wealth planning in maximizing your potential

This discussion offers valuable guidance for entrepreneurs aiming to maximize their business value and ensure a smooth transition that aligns with their personal and financial goals. Joe emphasizes the importance of proactive planning, stating, "If you don't design your exit, one will be designed for you. Every business owner is going to transition out of their business one day, so be proactive about it."

The conversation also touches on the emotional aspects of selling a business, with Joe and Gary sharing anecdotes that highlight the challenges many business owners face when contemplating their exit.

To listen to the full episode and gain deeper insights into successful business exit strategies, click the button below.

Joseph LoPresti was recently interviewed in the Business Creators Radio Show, hosted by Adam Hommey. They delved into the critical topic of "Business Exit Planning," drawing from Joe’s wealth of experience accumulated over nearly four decades in wealth management and business consulting.

The podcast episode explores crafting a fulfilling endgame strategy, addressing why many owners feel unprepared for this transition. Joe shares expert insights on crucial topics. He discusses the statistic that 80% of business owners regret selling within a year and offers strategies to avoid this pitfall. He introduces the "Freedom Point," helping owners determine when they can sell their business and live their ideal life.

Joe delves into boosting one's "Sellability Score," explaining key metrics buyers care about. He provides strategies for small teams to build value beyond owner dependency. Additionally, he explores the Virtual Family Office approach and its potential to save millions in taxes.

This discussion offers invaluable guidance for business owners at any stage of their exit planning journey. It aims to help maximize company value and ensure a smooth transition aligning with personal and financial goals. Joe’s insights provide a roadmap for designing an exit strategy that leads to true freedom and financial success.

To listen to the full episode and gain deeper insights into successful business exit strategies, click on the button below.

Recently, Joseph LoPresti had the privilege of joining George Grombacher on the Money Alignment Academy podcast. They explored the crucial topic of "Business Exit Planning," drawing from Joseph's 38 years of experience in wealth management and business consulting.

The podcast episode sheds light on the intricacies of a fulfilling endgame strategy, discussing why many owners feel unprepared for this significant transition. Joseph shares expert insights on proactive planning, including developing a personal action plan, optimizing your business for sale, and the importance of collaborative advisory teams.

This discussion offers valuable guidance for entrepreneurs aiming to maximize their business value and ensure a smooth transition that aligns with their personal and financial goals. Joseph introduces concepts like the "sellability score" and the benefits of a "virtual family office" approach to comprehensive planning.

To listen to the full episode and gain deeper insights into successful business exit strategies, click on the button below.

Considering a business exit but uncertain about optimizing your financial freedom? Recently, Joseph and Marissa LoPresti had the pleasure of joining Paul G. McManus on his podcast. They explored their co-authored book, "Exit by Design: Integrating Elite Wealth Management and Proactive Business Exits to Secure Your Freedom."

The book highlights the seamless integration of wealth management and business exit strategies, aiming to ensure a smooth and profitable transition for business owners.

The book insightfully merges wealth management with strategic business exit planning, tailored to ensure a smooth and profitable transition for entrepreneurs.

To listen to the full episode, click on the button below.