Making Money Online Is EASY (If You Do This) | Hudson Leogrande

The Urgency of Embracing AI

Hudson opens with a passionate argument on the necessity of learning artificial intelligence for entrepreneurs and business owners. He emphasizes that those who leverage AI tools can operate at an unprecedented speed and efficiency, whereas companies doing things manually will struggle to keep up. He illustrates how his brand uses AI not just for content creation but for data-driven optimization, such as analyzing thousands of user-generated videos weekly and letting an AI rate and predict their success before deployment. Hudson highlights how AI automates outreach, facilitates influencer selection on platforms like TikTok Shop, and fundamentally transforms marketing and scaling, making it an essential skill for survival in today's business climate.

Building Comfort

Hudson recounts the humble beginnings of Comfort, starting with sourcing manufacturers through Alibaba and sending samples of his favorite hoodies to find suppliers who could meet his criteria for fabric softness, weight, and quality. Their goal was to craft a hoodie softer than anything else on the market, inspired by brands such as Abercrombie & Fitch. The initial manufacturer quickly grew alongside the brand, necessitating expansion to multiple factories, even tapping into production facilities in Cambodia and Vietnam. Hudson shares that negotiating favorable payment terms with manufacturers was a key learning curve, moving from paying upfront to much longer net terms that better supported cash flow during rapid scaling.

The Power of Influencer Content

When reflecting on marketing tactics, Hudson focuses on the trio of exceptional product quality, community-building, and outstanding marketing, predominantly through influencer-generated content. Early on, he tested various formats to discover what actually resonated with audiences. He found that authentic, conversational videos where creators spoke candidly about their experience with Comfort's products worked best, often using casual street interviews or podcast clips to generate engagement. He emphasizes the importance of emotional triggers that prompt customers to hit "buy," such as scarcity and social proof, and how successful content combines strong hooks with genuine storytelling.

Hudson stresses that the brand originally relied mainly on micro-influencers and creators who might have been initially unsure about speaking to the camera. Gradually, the brand educated their content creators, providing loose scripts and showing them proven high-performing videos to replicate. Over time, the content strategy evolved to take risks with unique ideas, like hoodies with built-in eye masks and multiple innovative pockets. This iterative testing—failing fast and learning quickly—has been integral to Comfort's growth.

The Challenge of Media Buying

Hudson candidly admits that he is not a media buying expert himself but understands the fundamentals well enough to evaluate hires and results critically. His company spends substantial amounts daily on digital ads, particularly on Meta platforms, where advertising is still the gold standard for scalability. He explains how ads tend to lose effectiveness as budgets grow but that continuous testing and attribution tools like Northbeam, WorkMagic, or Triple Whale help them optimize cross-channel marketing efforts and calculate real profitability beyond platform-reported data.

He believes a great media buyer is adaptable and continuously learning, as old tactics quickly become outdated with algorithm changes. His approach combines data-driven insights with creative marketing and embraces new tools like AI for automating and refining campaigns.

Navigating Social Media Platforms

Hudson discusses how TikTok Shops have created new opportunities but also limitations. While TikTok is excellent for launching brands quickly with viral content and direct in-app shopping, its infrastructure and algorithms are still maturing and capped in scaleability and breadth of audience compared to Meta platforms. TikTok Shops may help startups gain fast traction, but for sustained scaling to hundreds of millions in revenue, Meta's robust ad platform remains superior.

He also touches on the differences between platforms and how content strategy and creator selection must adjust to platform-specific audiences and engagement patterns. Authenticity is vital across all platforms, especially with upcoming live streaming commerce, which demands real-time, unedited interaction.

Purely White Deluxe

Delving into Hudson's second venture, the teeth-whitening brand Purely White Deluxe, he acknowledges it is a smaller business compared to Comfort but still a success story. The product faced more limited total addressable market challenges compared to apparel, as fewer people become repeat customers and whitening products face heavy competition. Unlike Comfort's dominance on Meta ads, Purely White initially thrived on Snapchat influencer marketing, pioneering exclusive traffic through Snapchat story ads—a platform often overlooked in e-commerce.

However, algorithm changes at Snapchat forced them to pivot toward TikTok, where relatable, non-celebrity-driven content proved highly effective. Today, Purely White is reportedly the number one oral care brand on TikTok Shop, showing Hudson's adaptability and commitment to finding the right channel for each product.

Humility, Hiring, and Team Dynamics

Hudson paints an honest picture of startup life, explaining the initial fear he had in delegating tasks because of a belief he could do it best himself. Over time, he surrounded himself with talented specialists who handle complex areas like finance, product design, and supply chain. He stresses the importance of hiring passionate, aligned in-house staff over agencies, which he criticizes for lack of commitment and understanding of the brand's soul.

His team operates remotely but is tightly knit through frequent communication and shared culture, including collective learning via coaching materials and goal alignment. Hudson also reveals his emphasis on transparency and accountability, especially with high-stakes hires whose roles directly influence the company's growth and financial health.

Entrepreneurship Mindset

Throughout the conversation, Hudson repeatedly returns to the mindset required to succeed in e-commerce and online business. He talks about sacrificing much of his twenties for grinding 12-hour days with no breaks. He acknowledges the emotional toll entrepreneurship takes, describing it as lonely and stressful but worth the financial and geographical freedom it can eventually deliver.

He encourages entrepreneurs not to be afraid of failure, sharing stories of others who pivoted multiple times before finding their breakthrough. Hudson underscores that most millionaires and successful founders have failed hundreds or thousands of times but kept learning and adapting. This fearless experimentation mindset is central to his advice for anyone wanting to make money online and scale sustainably.