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

Subscribe to the podcast newsletter at https://thefailurefactorpodcast.com

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

Scott Harrison is the founder and CEO of charity: water, a nonprofit that has funded over 171,000 projects to bring clean, safe, drinkable water to more than 20 million people across 29 countries.

Unfulfilled from a decade of living the fast-paced extravagance of a nightclub promoter, he decided to seek a more purposeful life. He parted toward West Africa to serve as a volunteer in a hospital, where he witnessed first hand the devastating impacts of dirty water on the health and lives of people in developing countries. Join us as we unravel Scott’s journey –how this experience began a profound transformation so he turned his life around and built an organization dedicated to providing drinking water to millions around the world.

We discuss the challenges faced in this transition, the global water crisis, the role of women in water collection, and the importance of education and sanitation. Scott also reflects on his childhood experiences and the pivotal moments that led him to seek true happiness beyond material success.

Scott is the author of the New York Times bestselling book "Thirst" and has been recognized in Fortune Magazine’s 40 under 40 list, the Forbes Magazine Impact 30 list, and in Fast Company's 100 Most Creative People in Business issue.

Listen to the story that will challenge you to think differently about giving and inspire you to create meaningful change in the world.

Key Takeaways and Topics:

• Scott Harrison’s transitioning from nightclub promoter to philanthropist.
• Charity Water's vision was to provide clean water to every person in the world.
• 703 million people currently drink contaminated water.
• 80% of those without water live in rural areas.
• Women and girls bear the burden of water collection.
• Lack of water and sanitation leads to girls dropping out of school.
• Scott's childhood shaped his caregiving role and independence.
• A moment of clarity led Scott to seek fulfillment beyond wealth.
• True happiness is found in purpose, not material possessions.
• The pivotal moment that led to a desire to serve others.
• Scott’s experiences in Liberia highlighted the dire need for clean water.
• Sharing stories helped build awareness and engagement.
• Art exhibitions became a means to raise funds for humanitarian efforts.
• Scott’s vision to reimagine charity with creativity and transparency.
• Promoting the right cause is crucial for impact.
• Visual storytelling can evoke stronger emotional responses.
• A clear solution to a problem can drive donations.
• Creating a business model that ensures transparency builds trust.
• Emotional experiences can motivate people to take action.
• The 100% model attracted donors who wanted to see direct impact.
• Financial crises can lead to innovative solutions and growth.
• Learning from failures is essential for organizational improvement.
• Effective risk management is key in charity work.
• Building strong relationships with donors can lead to long-term support.
• Failures can lead to significant growth and learning.
• Radical transparency is essential for restoring trust.
• The subscription model significantly increased revenue.
• Personal fulfillment often outweighs financial gain.
• Integrity is the most important value in leadership.
• Perseverance is key during challenging times.

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

Learn more about Charity: Water: https://www.charitywater.org
Sponsor a water project: https://www.charitywater.org/donate
Buy the book: https://www.charitywater.org/thirst
Ig: https://www.instagram.com/charitywater
In: https://www.linkedin.com/company/charity-water

Follow Scott
Ig: https://www.instagram.com/scottharrison
In: https://www.linkedin.com/in/scottharrison1

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

Subscribe to the podcast newsletter at https://thefailurefactorpodcast.com

Themes: Charity Water, Scott Harrison, clean water, global philanthropy, water crisis, women empowerment, education, sanitation, personal journey, faith, personal growth, humanitarian work, clean water, charity, transformation, service, awareness, community, mission, charity, fundraising, storytelling, business model, emotional impact, nonprofit, marketing, visual communication, donor engagement, innovation, entrepreneurship, integrity, failure, purpose.

Alexandra Zatarain is the co-founder and VP of Brand and Marketing of Eight Sleep, the world's first sleep fitness company. With accolades like being named to Forbes 30 Under 30 and Inc’s 100 female founders lists, Alexandra is the marketing genius that helped put Eight Sleep on the map. 

Starting Eight Sleep with minimal marketing experience, she managed to redefine their product category through a long process of trial and error. Alexandra shares her thoughts about the importance of feedback, effective communication, humility, and long-term planning while emphasizing the need to embrace challenges, learn from failures, and maintain a growth mindset.

Listen to her insights on navigating the complexities of entrepreneurship and innovation, particularly in the tech space.

Key takeaways:

• The journey of entrepreneurship is often messy and filled with failures.
• Understanding customer needs is crucial for product development.
• Feedback from early users can guide product improvements.
• Positioning is critical for startup success.
• Growth comes from learning through challenges and failures.
• Embracing feedback as a learning opportunity can lead to growth.
• Humility is a key trait for effective leadership.
• Scaling a business introduces new complexities and challenges.
• Long-term planning is necessary for sustainable growth.
• Feedback should be immediate and constructive, not just negative.
• Assuming good intentions helps in receiving feedback positively.
• Continuous learning is vital in entrepreneurship.
• Building a supportive community can alleviate the fear of failure.

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

Learn more about Eight Sleep: https://www.eightsleep.com
Ig: https://www.instagram.com/eightsleep
In: https://www.linkedin.com/company/eight--

Follow Alexandra
Ig: https://www.instagram.com/alexzatarainj
In: https://www.linkedin.com/in/alexandrazatarain

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

Subscribe to the podcast newsletter at https://thefailurefactorpodcast.com 

Themes: entrepreneurship, sleep technology, Eight Sleep, failure, innovation, marketing, crowdfunding, product development, difficult conversations, leadership, entrepreneurship, feedback, leadership, scaling, business growth, humility, team dynamics

Serial entrepreneur Tara Simich launched Mermade Hair's hero product, the Mermade Waver, right before the pandemic hit. The brand became an overnight success, blowing up on Instagram to the point at which she and her team couldn't keep up with supply. The supply chain issues were wildly exacerbated by the pandemic, and she was soon faced with unhappy customers calling the product a sham – which, given the main marketing platform was Instagram, threatened to bring down the brand. Listen in to hear how Tara managed the stress of the supply issues and trolling customers, how she mitigates "mom guilt," and the growth mindset she brings to entrepreneurship that's been at the root of her success. 

Nicci Levy is the founder and CEO of Alchemy 43, a DryBar-meets-Botox-and-fillers concept transforming the experience of cosmetic injectables. In this episode, she shares the story behind Alchemy43; how she and her team almost had to close their doors because they ran out of money; and the empowering wisdom for taking risks and persevering through challenges that she learned along the way.