Episode 64

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Published on:

4th Aug 2025

Contractor vs Employee for Small Business Owners with Leah Weinberg

In this eye-opening episode of the Wealth Witches Podcast, Katelyn sits down with Leah Weinberg, a lawyer, author, and former wedding planner, to unpack one of the most misunderstood topics in the business world: the legal and financial differences between employees and independent contractors.

Whether you’re hiring your first team member or reviewing your current structure, Leah breaks down what every small business owner needs to know to stay compliant, avoid costly fines, and make confident decisions.

They also dig into the real risks of misclassification, why a contract doesn’t automatically protect you, and how your business might accidentally be waving red flags without even realizing it.

Key Takeaways

  • Why misclassifying a contractor as an employee can trigger audits, fines, and back taxes.
  • How to proactively audit your working relationships before the government does.
  • The surprising red flags that can expose your business to legal risk.
  • Identifying when it’s time to reassess, reclassify, and maybe even "tell on yourself" to the IRS.

Guest Bio:

Leah Weinberg is the founder of Weinberg Legal, an attorney, a recovering wedding planner, and the author of The Wedding Roller Coaster. 

After nearly a decade running her New York-based wedding planning company, Color Pop Events, she returned to her legal roots to support creative entrepreneurs and event professionals.

She’s also a longtime WeddingPro Educator with The Knot and WeddingWire, and speaks at industry events all over the world.


Connect with Leah Weinberg:

Website: https://www.weinberglegal.com/

Instagram: https://www.instagram.com/theLeahWeinberg

LinkedIn: https://www.linkedin.com/in/leah-weinberg-50655a19/


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Thanks so much for listening to our podcast! If you enjoyed this episode and think that others could benefit from listening, please share! Follow us on Instagram @WealthWitchesPodcast or drop us a message with your questions and episode requests. Looking for more finance tips, visit our main Instagram @thefreelancecfo.


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Stay magical and empowered, and remember, wealth isn't just about dollars in the bank – it's about creating abundance in all aspects of your life.

DISCLAIMER: This Podcast may receive compensation for promoting or recommending products or services through affiliate links. We only recommend products and services that we believe are of value to our listeners. The content provided in this podcast is for informational purposes only and does not constitute professional financial, accounting, or legal advice. Listeners are advised to consult with qualified professionals before making any financial decisions. The Freelance CFO is not responsible for any actions taken based on the information provided.


Music credit: Neon Fairies by Wolves 

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About the Podcast

Wealth Witches
Where financial empowerment meets magic!
Welcome to the Wealth Witches™ podcast, where financial empowerment meets magic! I'm Katelyn Magnuson, your guide on this enchanted journey to holistic wealth and prosperity. Here, we honor all identities and invoke our inner witches to create a community where everyone feels welcome and inspired.

Formerly known as the Confident Money podcast, we've transformed into Wealth Witches™ with Katelyn Magnuson. This change is about embracing the once-taboo topics of money and magic, blending them into a powerful mix of practical advice and mystical insights. Whether you're here for financial tips or to explore the magical side of life, this podcast is your new home.

What can you expect from Wealth Witches™? We combine actionable financial advice with a holistic approach to life. You'll hear from guests like astrologers, neurodivergent business owners, and magical creatives, discussing everything from business requirements to the latest trends in holistic wealth. We're breaking down the barriers that make finance feel dry and inaccessible, making it exciting and relevant to your life.

This podcast is for anyone who feels out of place in the traditional financial world. If you've ever felt like your interests in magic, human design, or holistic living didn't belong in a financial conversation, this is the podcast for you. We're here to tell you that you can embrace all parts of yourself and still be financially successful. We're not just talking about money – we're talking about creating a life of abundance and freedom. Our community is dynamic, diverse, and inclusive, and we want you to be a part of it.

Join us as we explore new ways to think about money and life. We're here to challenge the status quo and help you embrace your inner witch on your financial journey. Each episode is designed to inspire, educate, and empower you to take control of your financial destiny.

🔮 Wealth Witches™ Monthly Membership Program 🔮
Are you ready to take your financial journey to the next level? Join the Wealth Witches™ membership for exclusive access to live training sessions on money, taxes, retirement, and business support. You'll also gain entry to our inclusive community where you can connect with like-minded individuals and get even more out of your financial journey. We're a community of passionate, purpose-driven entrepreneurs who see creating wealth holistically rather than stuck in another crypto-bro investing black hole membership. Join today: www.thefreelancecfo.com/wealth-witches-podcast-member

Follow us on Instagram @WealthWitchesPodcast or drop us a message with your questions and episode requests. If you want more advice, visit our main Instagram @thefreelancecfo.

🌟 Enter to Win a Free Month of Wealth Witches™ Membership! 🌟
Leave a 5-star review and include your IG handle to enter. We draw the winner at the beginning of each quarter.

Stay magical and empowered, and remember, wealth isn't just about dollars in the bank – it's about creating abundance in all aspects of your life. Let's conjure some financial clarity together.

DISCLAIMER: This Podcast may receive compensation for promoting or recommending products or services through affiliate links. We only recommend products and services that we believe are of value to our listeners. The content provided in this podcast is for informational purposes only and does not constitute professional financial, accounting, or legal advice. Listeners are advised to consult with qualified professionals before making any financial decisions. The Freelance CFO is not responsible for any actions taken based on the information provided.

About your host

Profile picture for Katelyn Magnuson

Katelyn Magnuson

Katelyn, the driving force behind The Freelance CFO and creator of Wealth Witches, is revolutionizing accounting with a sprinkle of magic. With a decade of experience, she’s not your typical number cruncher. Her unique blend of expertise and approachability, infused with a touch of spiritual insight, has made her a go-to authority. Katelyn believes finance should be a stepping stone to success, not a barrier. With a judgment-free ethos, she simplifies complex financial topics, making them actionable for entrepreneurs and small businesses. Her ultimate goal? To empower you to manifest your authentic life—not a cookie-cutter one!