In this episode of the NASPP Equity Expert Podcast, we are joined by Jonathan Fish, the CEO and co-founder of Cap Gains. Jonathan brings his extensive experience as a CPA and public accountant, focusing primarily on venture funds and private equity funds. He shares insights into the world of Qualified Small Business Stock (QSBS), a powerful tax incentive that can offer 100% capital gains tax savings.

The key points of this episode include:

1. Introduction to QSBS
   • Understanding QSBS and its benefits
   • Historical context and changes over time
   • Importance for venture funds, entrepreneurs, and early employees
2. Corporate and Shareholder Level Requirements
   • Requirements at the corporate level, such as being taxed as a C Corp and having less than $50 million in gross assets
   • Shareholder requirements, including original issuance of stock and a five-year holding period
   • Common pitfalls and misconceptions around QSBS eligibility
3. Navigating QSBS Regulations and IRS Audits
   • The role of private letter rulings from the IRS in determining qualified trades or businesses
   • Potential complications from actions like stock redemptions, S elections, and exceeding asset thresholds
   • Recent changes in tax legislation affecting QSBS, such as the capitalization of R&D expenses
4. Market Trends and Awareness
   • The impact of market liquidity and legislative changes on the popularity and understanding of QSBS
   • Strategies for maintaining eligibility and maximizing benefits, including the Section 1045 rollover provision for gains reinvestment

Additional Resources:

• Founders, Unlock Big Tax Savings with Qualified Small Business Stock (QSBS)

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In this episode of the Equity Expert Podcast, we are joined by DeRonnie Pitts of Fidelity Private Shares where we discuss his experience with Cap Tables and their affects on fundraising rounds and investor perception.

The key points of this episode include:

• Guest Introduction and Background: 0:00 - 4:01
  
  
• Importance of Cap Table Management: 4:02 - 12:43
  
  
• Role of Equity in Motivating Employees: 12:44 - 18:15
  
  
• Discussion on "Salary Men" and Investor Expectations: 18:16 - 21:24
  
  
• Best Practices for Cap Table Management: 21:25 - 25:55
  
  

Additional Resources:

Solution Showcase: Cap Table Event
Best Way to Prepare For an Exit? Get Your Cap Table Right From The Start!
Founders Mistakes - Cap Tables

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In this episode of the Equity Expert podcast, we are joined by Chris Hoffman the founder of Equity Admin co. A Cap Table specialist with extensive experience in managing the equity of companies ranging from newly incorporated startups to some of the largest private companies in the world.

The key points of this episode include:

• What is a cap table?
• Common mistakes founders make
• Best Practices

Additional Resources:

https://www.naspp.com/blog/the-crucial-role-of-cap-tables
https://info.naspp.com/cap-tables-showcase

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