From DIY to Eight-Figure Success: The Journey of Highland Haircare

In this edition of Side Hustle Spotlight, we explore the story of Boone Whiteside and Ben Medalie, the dynamic duo behind Highland, a rapidly growing haircare brand. Starting as a humble DIY project in a Denver apartment, Highland has transformed into an eight-figure business in only three years. Responses from the founders have been edited for brevity and clarity.

Inception and Inspiration

Boone Whiteside recounts how he and Ben Medalie became close friends during their time at CU Boulder, united by their desire to pursue entrepreneurship. Whiteside’s vision for a cleaner, non-toxic hair care alternative spurred while he worked at an ecommerce startup that faced significant challenges. He notes, “I had one foot out the door, pulling me toward my calling of being my own entrepreneur.”

Meanwhile, Medalie was laboring through a monotonous analyst role at a payroll tech company, yearning for a more dynamic and fulfilling path. “Neither of us were happy with those career trajectories,” he shares. Frustrated with legacy brands using harmful chemicals in their products, Whiteside sought to create a solution that met his own consumer needs, believing it would resonate with like-minded individuals.

Getting Started

The initial steps toward launching Highland involved extensive online research to find natural, plant-based ingredients that could create effective hair products. With no formal chemistry background, Whiteside began experimenting with various materials in his kitchen. “I was weird enough to start putting these failed concoctions into my hair,” he admits. This led to gathering feedback from friends, further enhancing product development.

Resources for Growth

According to Medalie, various tools significantly aided their business operations:

• Klaviyo for email marketing
• Shopify for ecommerce
• Triple Whale for sales metrics
• Amped (now Mailchimp) for lead capture
• Adobe Premiere for content production
• Figma for design purposes

Whiteside adds that the most crucial free resource was their determination to seek assistance from seasoned entrepreneurs. “People generally want to help, but you can’t be afraid to ask,” he emphasizes.

Learning from Experience

If they could revisit any strategy from their journey, Whiteside would prioritize understanding their unit economics earlier. “Get very serious about your unit economics from day one,” he advises. The founders eventually achieved self-sustainability and profitability, a significant milestone for their venture.

Challenges Faced

Medalie notes that achieving consistent formulations for their natural products proved to be a daunting task. “We learned fast why all those who came before us cut the corners they did.” Throughout their journey, they faced numerous setbacks, including significant losses from failed product batches.

Overcoming Financial Difficulties

A specific challenge for the team was navigating cash flow issues right after their initial funding. “The process dragged on for months, and ultimately, the deal fell through,” Whiteside recalls. They adapted by reducing expenses and focusing on becoming cash flow positive despite the setbacks. Medalie reflects, “It forced us to prove our path to becoming cash-flow positive and helped us retain more ownership.”

Revenue Progression

After launching in 2021, Highland faced modest monthly earnings of $1,000 to $3,000 until mid-2023, when consistent monthly revenue began to emerge, averaging between $10,000 and $20,000. By 2025, Highland marked a significant milestone with a million-dollar month and has been profitable for nearly two years.

What They Enjoy Most

Both founders express their enjoyment of working together with friends and family. “Every single day is different, and getting to see yourself and friends grow is incredibly powerful and motivating,” Medalie shares. Whiteside echoes this sentiment, highlighting the importance of purpose and problem-solving in their entrepreneurial journey.

Advice for Aspiring Entrepreneurs

Whiteside concludes with a valuable piece of advice: “Beware the incoming call.” He emphasizes the importance of staying focused on your business goals and not letting external noise distract from your vision. This clarity in purpose is vital for driving success.

As Highland continues to innovate in the haircare space, their journey serves as an inspiring blueprint for aspiring entrepreneurs. Through dedication, adaptability, and a commitment to their values, Whiteside and Medalie have built a brand that stands for quality and sustainability.