The Clear Cut Co-Founder & CEO Olivia Landau on Growing an "Accidental Side Hustle" to Nearly $100M, Myths of Diamond Industry, and Proving Investors Wrong

The Failure Factor

Olivia Landau, Co-Founder and CEO of The Clear Cut—the largest digitally native natural diamond jewelry company in the United States—shares how a side hustle selling engagement rings through Instagram DMs transformed into a company that's hitting $100M in revenue.

Despite being dismissed by venture capitalists and warned by her family not to become an entrepreneur, Olivia Landau chose to bet on herself. Alongside her then-boyfriend (now husband and co-founder), Kyle, she took a leap of faith, walking away from the safe path and rejecting startup “best practices” that didn’t feel aligned.

Instead of following the noise, she doubled down on what felt right: human connection, deep education, craftsmanship, and building slow and intentionally. Her voice is a powerful reminder of what can happen when you block out the noise, trust your gut, and build your way—even when everyone says you’re doing it wrong.

Key Takeaways and Topics:

• How The Clear Cut started as an educational blog and Instagram side hustle

• Olivia’s generational roots in the diamond industry and how that shaped her approach

• The myths around lab-grown vs. natural diamonds—and why she refuses to sell lab-created stones

• Fundraising rejection: Why no VCs would invest and how they raised $700K from angels and customers instead

• The Clear Cut’s breakthrough moment during the pandemic and how their custom-built tech scaled the business

• Why “unscalable” things are worth doing first

• The emotional toll and impostor syndrome that come with fundraising and startup leadership

• How Olivia navigates being a new mom, co-founder, and CEO

• Debunking ethical misconceptions about natural diamonds—and why the real story matters

• Why having a personal brand and showing your face on social media can be a competitive advantage

• Her advice to aspiring founders: Don’t wait for perfection, just take the first step

Disclaimer:

Olivia shares her view that natural diamonds can be more ethical than lab-grown alternatives. This is a nuanced topic; what is “ethical” depends on your values. Natural diamonds may support economies like Botswana’s, while lab-grown stones produced with renewable energy may appeal to those prioritizing environmental impact.

Some stats shared from memory have been clarified:

• Diamonds make up 25–30% of Botswana’s GDP, not 80% as mentioned (that figure refers to exports).

• Diamond revenues fund free primary education, subsidized secondary education, and universal healthcare in Botswana.

• While “stipends” aren’t standard, the government provides scholarships and financial support to students and select groups.

We’ve included these clarifications to support informed decision-making.

The Failure Factor Podcast was brought to you by Off The Field Coaching. Explore working with one of our coaches at http://offthefieldcoaching.com

Hosted by Megan Bruneau: therapist, executive coach, speaker, Forbes contributor, and host of The Failure Factor. For more info, visit https://meganbruneau.com

Follow Olivia and The Clear Cut

Her Ig: https://www.instagram.com/olivialandau The Clear Cut: https://www.instagram.com/theclearcut

Follow Megan Ig: https://www.instagram.com/meganjbruneau/ In: https://www.linkedin.com/in/megan-j-bruneau-m-a-rcc

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Themes: entrepreneurship, diamond industry, The Clear Cut, venture capital, scaling a startup, personalized luxury, ethical sourcing, tech, jewelry, women founder, e-commerce, working with a partner, motherhood, impostor syndrome, custom jewelry, resilience, lab-grown diamonds, natural diamonds, storytelling, brand building