Why do entrepreneurs who start businesses for freedom end up more trapped than they were as employees?

In this Scaling with People episode, Joe LoPresti explores the freedom paradox—and why exit planning should begin the day you launch.

When Gwenevere asks when founders should start thinking about exit, Joe's answer surprises her: "You should start the day you launch." Her response reveals every entrepreneur's challenge: "But Joe, most business owners don't do that..."

Joe introduces the "Freedom Point" framework with four dimensions: financial, time, relationship, and purpose freedom. He explains why most owners have 80% of wealth tied to their business—creating anxiety during the transition from something they control to markets they can't.

The conversation covers three critical tracks: business-level planning focused on enterprise value, personal wealth planning requiring 2-3 years lead time for tax strategy, and personal action planning answering: "What are you going to do Monday morning after the business is sold?"

Joe shares that one-third of exits are unplanned—triggered by the "Five Ds" (death, disability, divorce, disagreement, distress)—making early preparation essential. He addresses the "dumb tax"—costly decisions from lack of awareness—and why qualified advisors aren't enough if they're not coordinating.

Key topics: how owner dependency destroys value ("If it's very dependent on you, it's not very valuable to them"), why buyers evaluate businesses differently than owners, the 3-5 year timeline separating success from regret, and how fractional family offices serve owners with $5-75 million.

"People who aren't proactive end up exiting by default. And that's when something usually leads to regret."

🎧 Listen now to design your exit from day one—and build a business that serves your freedom.

In this eye-opening episode, Joe LoPresti explores the paradox facing business owners: why entrepreneurs who built companies for freedom often find themselves trapped by it. Drawing from decades of experience, Joe reveals why 80% of businesses never sell and the invisible coordination problem that costs owners millions.

The conversation covers Joe's fractional family office model, the lifetime cash flow planning process, and why the "forgotten market" of $5-75 million business owners needs specialized attention. Jeff and Joe dive deep into the difference between building wealth and securing true freedom, exploring why most owners get stuck in the "red zone" of exits.

Key insights include the diagnostic question every owner should ask their advisors, why traditional planning fails business owners, and how to design your exit rather than default into one.

🎧 Listen now to discover why most business exits fail and the coordination strategies that separate success from regret.

“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.

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 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 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 "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.

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.

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.

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.