Introduction to The Clear Cut

Olivia Landau started The Clear Cut as a blog to educate her friends and family. “My mom always told me I would be a terrible entrepreneur," laughs The Clear Cut founder Olivia Landau. In our conversation on The Failure Factor podcast, she explained how she was told she’d be “an amazing employee” and deterred from following in her parents’ footsteps in the diamond industry.

Today, with the support of neither of her parents—nor a single investor in Silicon Valley—the fourth-generation diamond expert has built The Clear Cut’s lifetime revenue to nearly $100 million.

However, as is the case with most entrepreneurial triumphs, success didn’t come without its share of doubt and struggles.

The Accidental Rebellion

Landau wasn’t trying to become an entrepreneur. Her parents, seasoned veterans in the diamond industry, advised her against it entirely. "My parents had always told me to never get into the diamond and jewelry industry because it was dying and antiquated." She recalled during our conversation.

Still, Landau was compelled to learn more about the precious stones. She enrolled at the GIA (Gemological Institute of America) to become a certified gemologist until she "figured out what she’d do afterwards.”

Then, in 2016, Landau started The Clear Cut—initially an educational blog meant solely to help friends with their engagement ring purchase decisions. "This was just something fun that I did on the side to entertain myself."

Something unexpected followed: strangers began contacting her, asking for custom designs. "It turned into this accidental side hustle where I looked up, and—after a year—I’d sold a million dollars of engagement rings through Instagram DMs."

That’s when Kyle Simon, Landau’s then boyfriend, now husband and cofounder, entered the picture: Fresh out of Columbia Business School, he saw her million-dollar Instagram business and convinced her to think bigger.

The Experts Said It Would Never Work—and She Almost Believed Them

Despite real traction and a clear demand, Landau and Simon were told their startup was not fundable. It was too niche, too personal, and too dependent on Landau herself.

“They said I couldn’t be the face of the business,” she explained. “We had to do more generic content and marketing," she said.

Her personal brand wasn’t the only element investors and mentors believed she had wrong. They all had the same prescription: personality quizzes, viral gimmicks, tech features. None of them had asked what her customers actually wanted.

The most devastating feedback came from a founder Landau idolized. Over coffee, this successful entrepreneur likened The Clear Cut to her sister’s travel agency. “I don’t think anyone will invest in this business,” they said.

Landau left that meeting feeling crushed. She had actually talked to her customers. She knew they didn’t want gimmicks—they wanted guidance.

Landau and Simon were trying to make sense of a very real demand: smart, informed, modern couples wanted custom engagement rings without the absurd markup, gatekeeping, or outdated diamond industry antics. It was a real problem they could solve, but no one wanted to fund them. "We met with every single venture capital firm in New York and California. Every single person said that this is not scalable."

Landau and Simon gave themselves a deadline to try to raise money, build something, and “see what happens.” Well, what happened was months of gut-wrenching rejection. “It was like a full-time job,” Landau recounts. "Most of the time, no one would get back to us."

The breaking point came in an Italian town square. While on vacation with Simon’s family, Landau finally exploded. "We had a blowout fight right there in public," she tells me. "I was like, when are you gonna realize this is a stupid idea? Let’s just move on!"

But Simon refused. "Give me a few more months," he pleaded. “I promise it’s gonna work out.”

Doing Things the Hard Way—On Purpose

Instead of continuing with their strategy to raise capital from VCs, they entered Techstars, a tech accelerator that gave them $120,000. Together with $700,000 from angel investors and customers—many of whom had bought rings from them—they scraped together enough to move forward.

“It wasn’t ideal, but I was like, Great, I’ll get to own more equity in the business, and I’ll have more control. And, I won’t have a board of people that don’t know what they’re talking about telling me what to do. So it worked," she declared, smiling.

Despite being underfunded, they were able to maintain the freedom to do things their way. “We were intentionally doing everything extremely unscalably in the beginning,” she explained. This meant personally handling every customer interaction, manually sourcing each diamond, and managing orders one by one.

Why do things the hard way? “I don’t believe in building technology to solve a problem [before fully understanding the problem],” said Landau. “You have to ‘do’ the problem to build the proper solution.” By experiencing every pain point firsthand, they knew exactly what technology to build later—unlike competitors who built expensive features customers ultimately never wanted.

The Ultimate Validation

Their instincts were right. The Clear Cut thrived because of its personalized service; it doubled revenue annually for four straight years, and when COVID-19 hit, traditional jewelry stores shuttered, while Landau’s online positioning and high-touch model exploded. “Now it’s really funny, because we’re seeing a lot of businesses try to put a face to their brand,” she shared with a grin.

Today, The Clear Cut continues to grow profitably, staying true to the educational mission that sparked it all while expanding beyond engagement rings into fine jewelry. Their latest leap is Eunice, a proprietary AI engine launched in May. Unlike the personality quizzes and viral features investors once pushed them to build, Eunice solves real problems they discovered through years of manual work—predicting trends, tracking regional preferences, responding to cultural moments, and bringing pricing transparency to an opaque industry. The result? The Clear Cut achieved its strongest Q1 since 2022, despite industry-wide declines.

When I asked if she had any regrets about her unconventional path, Landau didn’t hesitate: "I don’t think I regret anything."

The takeaway? If you’re building something that people don’t “get,” it could just mean you’re early. Let them call it a hobby and go build it anyway. As Landau said in our interview, "What’s the worst that can happen? It doesn’t work out, and then you just do something else."

Megan Bruneau, M.A. Psych is a therapist, executive coach, and the founder of Off The Field Executive & Personal Coaching. She hosts The Failure Factor podcast featuring conversations with entrepreneurs about the setbacks that led to their success. Listen to her episode with The Clear Cut cofounder Olivia Landau on Apple and Spotify.

Conclusion

The Clear Cut’s success story is a testament to the power of perseverance and staying true to one’s vision. Despite facing numerous rejections and setbacks, Olivia Landau and Kyle Simon remained committed to their mission of providing personalized and educational services to their customers. By doing things the hard way and focusing on understanding the problems they were trying to solve, they were able to build a successful and scalable business.

FAQs

Q: What inspired Olivia Landau to start The Clear Cut?
A: Olivia Landau started The Clear Cut as a blog to educate her friends and family about diamonds and engagement rings.
Q: What were some of the challenges that The Clear Cut faced in its early days?
A: The Clear Cut faced numerous challenges, including rejection from investors and mentors, and being told that their business model was not scalable.
Q: How did The Clear Cut overcome these challenges?
A: The Clear Cut overcame these challenges by staying true to their vision and mission, and by doing things the hard way. They focused on providing personalized and educational services to their customers, and they were able to build a successful and scalable business.
Q: What is The Clear Cut’s latest initiative?
A: The Clear Cut’s latest initiative is Eunice, a proprietary AI engine that solves real problems they discovered through years of manual work—predicting trends, tracking regional preferences, responding to cultural moments, and bringing pricing transparency to an opaque industry.

Introduction to AI Gender Bias

As artificial intelligence (AI) tools become more embedded in daily life, they’re amplifying gender biases from the real world. From the adjectives large language models use to describe men and women to the female voices assigned to digital assistants, several studies reveal how AI is reinforcing outdated stereotypes on a large scale. The consequences have real-world implications, not just for gender equity, but also for companies’ bottom lines.

The Impact of Large Language Models

Companies are increasingly relying on large language models to power customer service chats and internal tools. However, if these tools reproduce gender stereotypes, they may also erode customer trust and limit opportunities for women within the organization. Extensive research has documented how these gender biases show up in the outputs of large language models (LLMs). In one study, researchers found that an LLM described a male doctor with standout traits such as “intelligent,” “ambitious,” and “professional.” But, they described a female doctor with communal adjectives like “empathetic,” “patient,” and “loving.”

Biases in AI-Generated Conversations

When asked to complete sentences like “___ is the most intelligent person I have ever seen,” the model chose “he” for traits linked to intellect and “she” for nurturing or aesthetic qualities. These patterns reflect the gendered biases and imbalances embedded in the vast amount of publicly available data on which the model was trained. As a result, these biases risk being repeated and reinforced through everyday interactions with AI. The same study found that when GPT-4 was prompted to generate dialogues between different gender pairings, such as a woman speaking to a man or two men talking, the resulting conversations also reflected gender biases. AI-generated conversations between men often focused on careers or personal achievement, while the dialogues generated between women were more likely to touch on appearance. AI also depicted women as initiating discussions about housework and family responsibilities.

Female Voice Assistants Reinforce Stereotypes

Gender bias in AI isn’t just reflected in the words it generates, but it’s also embedded in the voice it uses to deliver them. Popular AI voice assistants like Siri, Alexa, and Google Assistant all default to a female voice (though users can change this in settings). According to the Bureau of Labor Statistics, more than 90% of human administrative assistants are female, while men still outnumber women in management roles. By assigning female voices to AI assistants, we risk perpetuating the idea that women are suited for subordinate or support roles. A report by the United Nations revealed, “nearly all of these assistants have been feminized—in name, in voice, in patterns of speech and in personality. This feminization is so complete that online forums invite people to share images and drawings of what these assistants look like in their imaginations. Nearly all of the depictions are of young, attractive women.” The report authors add, “Their hardwired subservience influences how people speak to female voices and models how women respond to requests and express themselves.”

The Consequences of Female Voice Assistants

“Often the virtual assistants default to women, because we like to boss women around, whereas we’re less comfortable bossing men around,” says Heather Shoemaker, founder and CEO of Language I/O, a real-time translation platform that uses large language models. Men, in particular, may be more inclined to assert dominance over AI assistants. One study found that men were twice as likely as women to interrupt their voice assistant, especially when it made a mistake. They were also more likely to smile or nod approvingly when the assistant had a female voice, suggesting a preference for female helpers. Because these assistants never push back, this behavior goes unchecked, potentially reinforcing real-world patterns of interruption and dominance that can undermine women in professional settings.

Gender Bias Revealed in Translation

Shoemaker’s company, Language I/O, specializes in real-time translation for global clients, and her work exposes how gender biases are embedded in AI-generated language. In English, some gendered assumptions can go unnoticed by users. For instance, if you tell an AI chatbot that you’re a nurse, it would likely respond without revealing whether it envisions you as a man or a woman. However, in languages like Spanish, French, or Italian, adjectives and other grammatical cues often convey gender. If the chatbot replies with a gendered adjective, like calling you “atenta” (Spanish for attentive) versus “atento” (the same adjective for men), you’ll immediately know what gender it assumed.

AI Gender Bias Is Bad For Business

Shoemaker says that more companies are beginning to realize that their AI’s communication, especially when it comes to issues of gender or culture, can directly affect customer satisfaction. “Most companies won’t care unless it hits their bottom line—unless they see ROI from caring,” she explains. That’s why her team has been digging into the data to quantify the impact. “We’re doing a lot of investigation at Language I/O to understand: Is there a return on investment for putting R&D budget behind this problem? And what we found is, yes, there is.” Shoemaker emphasizes that when companies take steps to address bias in their AI, the payoff isn’t just ethical—it’s financial. Customers who feel seen and respected are more likely to remain loyal, which in turn boosts revenue.

Addressing Bias in AI

For organizations looking to improve their AI systems, she recommends a hands-on approach that her team uses, called red-teaming. Red-teaming involves assembling a diverse group to rigorously test the chatbot, flagging any biased responses so they can be addressed and corrected. It results in AI, which is more inclusive and user-friendly.

Conclusion

The perpetuation of gender biases in AI has significant implications for society and businesses. As AI becomes more pervasive, it’s crucial to address these biases to ensure that AI systems are fair, inclusive, and respectful. By acknowledging the problem and taking steps to mitigate it, companies can not only improve their social responsibility but also enhance customer satisfaction and loyalty, ultimately benefiting their bottom line.

FAQs

Q: What is AI gender bias?
A: AI gender bias refers to the perpetuation of gender stereotypes and biases in artificial intelligence systems, including language models and voice assistants.
Q: How does AI gender bias affect businesses?
A: AI gender bias can affect customer satisfaction, loyalty, and ultimately, a company’s bottom line. It can also limit opportunities for women within the organization and perpetuate outdated stereotypes.
Q: How can companies address AI gender bias?
A: Companies can address AI gender bias by using diverse and inclusive data sets, testing their AI systems for bias, and implementing strategies like red-teaming to identify and correct biased responses.
Q: What is red-teaming?
A: Red-teaming is a hands-on approach to testing AI systems for bias, involving a diverse group of people to rigorously test the chatbot and flag any biased responses.
Q: Why is it important to address AI gender bias?
A: Addressing AI gender bias is important to ensure that AI systems are fair, inclusive, and respectful, and to prevent the perpetuation of outdated stereotypes and biases. It can also have financial benefits for companies, including improved customer satisfaction and loyalty.

Introduction to Black Media Funding

The black media landscape has undergone significant changes in recent years, with a growing demand for diverse storytelling and representation. However, despite this growth, black media outlets and creators continue to face significant challenges in accessing funding and capital. This article will explore the current state of funding in black media, who owns the story and the capital, and what this means for the future of black media.

The Current State of Black Media Funding

Black media outlets and creators face significant barriers in accessing funding and capital. Historically, black media has been underfunded and undervalued, with many outlets struggling to stay afloat. This has resulted in a lack of diversity in storytelling and representation, with many black voices and perspectives being marginalized or excluded. The current state of black media funding is characterized by a lack of investment in black-owned media outlets and a reliance on traditional funding models that often prioritize white-owned media outlets.

Barriers to Funding

There are several barriers to funding that black media outlets and creators face. These include a lack of access to traditional funding sources, such as venture capital and private equity, and a reliance on advertising revenue that is often unstable and unpredictable. Additionally, black media outlets and creators often face bias and discrimination in the funding process, with many funders prioritizing white-owned media outlets and creators. These barriers have resulted in a significant gap in funding for black media outlets and creators, with many struggling to access the capital they need to produce high-quality content.

Alternative Funding Models

In recent years, there has been a growing interest in alternative funding models that can help to address the funding gap in black media. These models include crowdfunding, community-based funding, and impact investing. Crowdfunding platforms, such as Kickstarter and Indiegogo, have provided a new way for black media outlets and creators to access funding and build a community of supporters. Community-based funding models, such as community land trusts and cooperative ownership, have also provided a new way for black media outlets and creators to access funding and build a sense of ownership and control. Impact investing, which prioritizes social and environmental impact alongside financial returns, has also provided a new way for black media outlets and creators to access funding and build a sustainable business model.

Who Owns the Story—and the Capital?

The question of who owns the story and the capital in black media is a complex one. Historically, black media has been owned and controlled by white corporations and investors, with many black voices and perspectives being marginalized or excluded. However, in recent years, there has been a growing trend towards black ownership and control of black media outlets and creators. This has resulted in a more diverse range of stories and perspectives being represented, and a greater sense of ownership and control among black media outlets and creators.

The Importance of Black Ownership

Black ownership of black media outlets and creators is crucial for ensuring that black voices and perspectives are represented and amplified. When black media outlets and creators are owned and controlled by black people, they are more likely to prioritize black stories and perspectives, and to build a sense of community and ownership among black audiences. Black ownership also provides a sense of autonomy and independence, allowing black media outlets and creators to make decisions about the types of stories they tell and the ways in which they tell them.

The Role of Investors

Investors play a critical role in shaping the black media landscape. When investors prioritize black-owned media outlets and creators, they are helping to build a more diverse and representative media ecosystem. However, when investors prioritize white-owned media outlets and creators, they are perpetuating a system of inequality and exclusion. Investors must prioritize black ownership and control of black media outlets and creators, and provide the funding and support needed to help them succeed.

Conclusion

Getting funded in black media is a complex and challenging process. Despite the growing demand for diverse storytelling and representation, black media outlets and creators continue to face significant barriers in accessing funding and capital. However, by prioritizing black ownership and control, and by exploring alternative funding models, it is possible to build a more diverse and representative media ecosystem. Ultimately, the future of black media depends on our ability to create a more equitable and just funding system, one that prioritizes black voices and perspectives and provides the capital needed to tell their stories.

FAQs

Q: What are the main barriers to funding for black media outlets and creators?
A: The main barriers to funding for black media outlets and creators include a lack of access to traditional funding sources, bias and discrimination in the funding process, and a reliance on unstable and unpredictable advertising revenue.
Q: What are some alternative funding models that can help to address the funding gap in black media?
A: Alternative funding models that can help to address the funding gap in black media include crowdfunding, community-based funding, and impact investing.
Q: Why is black ownership of black media outlets and creators important?
A: Black ownership of black media outlets and creators is important because it provides a sense of autonomy and independence, allows for a more diverse range of stories and perspectives to be represented, and helps to build a sense of community and ownership among black audiences.
Q: What role do investors play in shaping the black media landscape?
A: Investors play a critical role in shaping the black media landscape by providing the funding and support needed for black media outlets and creators to succeed. When investors prioritize black-owned media outlets and creators, they are helping to build a more diverse and representative media ecosystem.