Jonathan Wolfson, Chief Legal Officer and Policy Director at the Cicero Institute


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In this episode, Jonathan Wolfson, Chief Legal Officer and Policy Director at the Cicero Institute, comprehensively analyzes the freelance economy from legal and governmental perspectives. As we all know, compliance is a massive blocker in adopting freelancers at scale. Jonathan breaks down the policy side of how legislation is influenced, formalized, and leads to compliance regulations. While Jonathan is based in the US, understanding the forces of freelance legislation is applicable globally. 

More than today’s current legislation, Jonathan will also outline the history of employment law, which was established in the 1940s and does not accommodate today’s modern workforce. From this historical perspective, we’ll understand the government’s opposition to freelancing.

Last, Jonathan will highlight the challenges and opposition to freelancing, the risks and liabilities for businesses, the impact on business transactions, potential solutions and future outlook, the legislative landscape and regulatory changes, and actions individuals can take to make an impact.

Key takeaways: 

  • Legislative and regulatory changes are necessary to address the challenges of independent contracting, though the future remains uncertain
  • Current employment laws, dating back to the 1940s, fail to address the modern freelance economy
  • Misconceptions, political motivations, and concerns about tax collection and worker protection fuel opposition to freelancing
  • Businesses face significant risks and liabilities if workers are misclassified as independent contractors


00:00 – Introduction and Background

03:45 – Freelancers Choose to Freelance

14:27 – The Evolution of Independent Contracting

29:52 – Opposition to Freelancing

31:28 – Challenges and Opposition to Freelancing

33:26 – Risks and Liabilities for Businesses

36:05 – Impact on Business Transactions

40:36 – Potential Solutions and Future Outlook

52:27 – Legislative Landscape and Regulatory Changes

59:29 – Actions for Individuals to Make an Impact

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