Simply Tax® Episode 55: I ♥ ESOPs

Thoughtware Podcast Published: Feb 14, 2019
Simply Tax Episode 55

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An employee stock ownership plan (ESOP) is a tax-advantaged succession-planning vehicle and retirement plan that’s sometimes overlooked. Guest Cara Benningfield joins host Damien Martin to explain how ESOPs can help preserve the culture and legacy of a business and discuss the pros, cons and risks of an ESOP transaction.


  • Leveraged ESOPs @1:48
  • Contributory ESOPs @3:41
  • How ESOPs work @5:28
  • Where to start when evaluating an ESOP transaction @10:56
  • Situations where an ESOP isn’t a good fit @12:36
  • Benefits of an ESOP @15:46
  • Gain deferral under §1042 @22:15
  • Situations where ESOPs are particularly effective @29:24
  • ESOPs after tax reform @32:14
  • Common ESOP myths @42:47
  • A practical example of an ESOP success @45:48
  • Figure out what’s important @51:20
  • It takes a team @52:48


Cara Benningfield is a partner in BKD’s Bowling Green, Kentucky, practice and leader of BKD’s ESOP transaction services team. She structures and facilitates the creation of new ESOPs and works with existing ESOPs in matters ranging from acquisition structuring to repurchase planning and analysis. Cara’s experience with ESOPs also includes providing financing assistance, tax planning, ongoing plan administration, employee communication and structuring of executive incentive plans.


Bonus Discussion: Why Cara Benningfield ♥s ESOPs

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Video: Impacts of Tax Reform on ESOP Companies 
Webinar archive: ESOPs: Continuing a Legacy



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