Tag: Business Exit Planning
What Happens After You Sell Your Business? (Ep. 32 | Pt. 8)

What Happens After You Sell Your Business? (Ep. 32 | Pt. 8)

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Selling your business may feel like the finish line, but for many owners, it can mark the start of a completely new chapter. One surprising statistic discussed in this episode: nearly 70% of business owners report regretting the sale within a year. In many cases, owners may feel unprepared for what comes next.

In this episode, Dan Reese wraps up the business exit-planning series by exploring the emotional, financial, and personal realities that follow a business sale. From the shift in identity that happens after stepping away from daily operations to the challenge of transitioning from entrepreneur to investor, Dan explains why many business owners find that a successful transition involves more than just the valuation.

Dan discusses:

  • Why many business owners experience emotional challenges after selling
  • The difference between building wealth and preserving it
  • How fear and emotion can impact investing after a liquidity event
  • Why tax planning can play an important role before and after a sale
  • And more!

If you’re a business owner thinking about an exit, or already navigating life after one, this episode offers perspective on navigating the transition after a business sale. 

Whether you’re years away from selling your business or already thinking about life after work, this episode offers insight into building a retirement plan designed to align with your financial goals, personal priorities, and long-term legacy.

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Choosing the Right Exit Path for Your Business (Ep. 31 | Pt. 7)

Choosing the Right Exit Path for Your Business (Ep. 31 | Pt. 7)

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Selling a business involves both financial and personal considerations, and the transition path you choose may influence your long-term business, employee, and personal goals.

In this episode, the seventh in the business exit planning series, Dan Reese walks through the most common exit paths available to business owners, including strategic sales, private equity, ESOPs, management buyouts, and family transitions. He breaks down the pros and cons of each, explains how payment structures like earnouts and lump sums work, and addresses what buyers are actually looking for. 

Dan also highlights the biggest mistakes owners make, from waiting too long to ignoring tax planning and cultural fit.

Dan discusses:

  • How a strategic sale may result in higher valuations when a buyer sees immediate synergies with your existing business and processes
  • Why private equity may involve a larger upfront payment structure, and how earnouts and equity shares factor into the deal structure
  • How ESOPs may provide tax-related considerations, employee ownership opportunities, and continuity planning benefits for some companies for owners who want a gradual exit
  • Why the highest purchase price may not align with an owner’s broader priorities when legacy, culture, and employee impact matter to you
  • How procrastinating on exit planning and value acceleration may limit flexibility and preparation during a future transition
  • And more!

Resources:

Connect with Dan Reese CFP®:

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Managing Business Risk Before an Exit (Ep. 29 | Pt. 5)

Managing Business Risk Before an Exit (Ep. 29 | Pt. 5)

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Growth gets most of the attention, but what happens when hidden risks start to impact what an outside buyer may consider when evaluating your business?

What would an outside buyer see that you might be overlooking today?

In this episode, Dan Reese breaks down the fifth part of the business exit series, focusing on how business owners can help address risks that may affect value before a sale. He explains how risks like key person dependency, customer concentration, and weak systems may influence what buyers are willing to pay. 

The conversation highlights practical ways help to identify and manage these risks, including building leadership depth and improving processes. Dan also shares why viewing your business through a buyer’s lens can change how you prepare for an exit.

Key takeaways:

  • How reliance on one person can limit business value and create challenges when transitioning ownership
  • Why customer concentration and inconsistent revenue streams raise concerns for potential buyers
  • The impact of undocumented processes on hiring, training, and overall operational stability
  • How regulatory and legal exposure can influence valuation and ongoing profitability considerations
  • Practical steps to help reduce risk, including leadership depth, audits, and working with specialists
  • And more!

Resources:

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What’s Your Number? The Key to Selling Your Business Without Regret (Ep. 27 | Pt. 3)

What’s Your Number? The Key to Selling Your Business Without Regret (Ep. 27 | Pt. 3)

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Thinking about selling a business is one thing; knowing what you actually need from it is another.

How do you move from guessing a number to having greater clarity about your financial future and lifestyle?

In this episode, Dan Reese breaks down Part 3 of the business exit series, focused on defining “your number” through personal financial planning. He explains how business owners can identify their true financial needs, account for concentration risk, and understand the gap between what they have and what they may need. The conversation also highlights the importance of tax planning, building the right advisory team, and preparing well in advance to help reduce the likelihood of costly mistakes and uncertainty.

Key takeaways:

  • Why business owners should not rely on rough estimates when deciding how much they need from a sale
  • How personal financial planning can reveal true lifestyle costs and hidden benefits from a business
  • The role of concentration risk when most wealth is tied to a single company asset
  • Why taxes and deal structure can significantly reduce what you actually receive after a sale
  • How having the right team helps improve clarity and support more informed decision-making
  • And more!

Resources:

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Life After the Sale: Designing Your Next Chapter Before You Exit (Ep. 26 | Pt. 2)

Life After the Sale: Designing Your Next Chapter Before You Exit (Ep. 26 | Pt. 2)

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What happens when the title you have carried for decades suddenly disappears? How do you prepare for the emotional shift that comes after stepping away from your business?

In this episode, Dan Reese, CFP®, continues the business exit series by focusing on the personal side of transition. He explains why identity, routine, and purpose play such a critical role in life after a sale. Dan shares practical exercises to help business owners design their ideal week, align with their spouse, and prepare emotionally for what comes next. He also discusses research suggesting that many owners experience regret after selling and how intentional planning may help reduce the likelihood of regret.

Key takeaways:

  • Why identity transition is one of the biggest hurdles after selling a business
  • How routine and decision-making impact emotional well-being in retirement
  • The importance of lifestyle design and structuring your ideal week
  • Why spousal alignment and family communication matter before exiting
  • How proactive exit planning strategies can help business owners prepare emotionally and financially for transition
  • And more!

Resources:

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Are Business Owners Ready for the $14 Trillion Exit Wave? (Ep. 22)

Are Business Owners Ready for the $14 Trillion Exit Wave? (Ep. 22)

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Most business owners say they feel prepared to step away, but available data suggests gaps in readiness.

In this episode, Dan Reese breaks down insights from the National State of Owner Readiness Report and explains common areas where small and mid-sized business owners may lack preparation for a significant financial transition. With a large portion of many owners’ net worth tied up in their business, exit planning often involves business, personal, and financial considerations.

Dan walks through common elements often associated with readiness, including understanding business value, identifying wealth gaps, and planning considerations for life after the business following a transaction.

Dan discusses:

  • The role small and mid-sized businesses play in the U.S. economy
  • The commonly referenced three legs of exit planning: business, personal, and financial considerations
  • The role formal business valuations can play in exit planning
  • The wealth gap and how lifestyle expectations may affect a transition
  • And more

Resources:

Connect with Dan Reese CFP®:

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