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This Side Hustle Spotlight Q&A features Colorado-based entrepreneurs Boone Whiteside, 29, and Ben Medalie, 28. They are the co-founders of Highland, a haircare brand that began as a DIY project in a Denver apartment and has rapidly expanded into an eight-figure enterprise within three years. Responses have been edited for brevity and clarity.
When did you start your side hustle, and what inspired it?
Whiteside: Our friendship blossomed during our junior year at CU Boulder, where we connected over our shared ambition to create something of our own, moving away from the typical 9-to-5 grind of pursuing someone else’s dreams. However, it took a while for that aspiration to take shape.
As I envisioned a hair product company that would prioritize natural ingredients over harmful chemicals, I was working at an ecommerce startup facing its own struggles. This experience taught me invaluable lessons about business hurdles but left me longing for the entrepreneurial path.
Ben, meanwhile, was entrenched in his role at a payroll tech firm, where the monotony of daily tasks was stifling. He was balancing various responsibilities from sales to marketing, but the pressure to conform to a rigid job description made it less fulfilling for him. We both realized we weren’t satisfied with our respective career paths.
Frustrated with traditional hair styling products dominated by chemical-laden formulas and excessive packaging, I saw a gap in the market that echoed my needs as a consumer. Inspired, I believed this problem could resonate with a broader audience.
What initial steps did you take to launch your side hustle?
Whiteside: My first move was to scour the internet (long before AI) for natural, plant-based ingredients to create formulations free from harmful materials. Lacking any chemistry or culinary background, I started experimenting with waxes, clays, and oils on my stovetop.
Embracing my quirks, I was unafraid to test my unusual blends on my own hair and enlisted my friends to do the same, gathering their feedback. Ben, my roommate, was initially amused by my antics but soon joined in on the fun.
Are there any resources that have been particularly helpful for running your business?
Medalie: We rely on several standout tech tools, such as Klaviyo for email marketing, Shopify for our ecommerce platform, and Triple Whale for tracking metrics. Additional tools like Adobe Premiere have proven invaluable for content creation.
Whiteside: While Ben covered many paid resources, our most effective free resource has been our persistence in seeking advice from seasoned entrepreneurs. Most people are open to sharing their insights if you are willing to ask. A recent coffee meeting with Justin Gold, founder of Justin’s, encapsulated this attitude well: “Be unreasonable.” This approach has fostered a supportive network that has been instrumental in refining our business strategy while helping us learn from others’ missteps.
If you could revisit your business journey and change one aspect, what would it be?
Whiteside: We were diligent in understanding our unit economics, but I wish we had prioritized this even sooner. Grasping the importance of gross margins from the onset is crucial. Establish a clear plan to reduce costs over time, as every penny impacts the sustainability of the business. Understanding finances is essential to achieving profitability sooner rather than later, especially given the shifting landscape of fundraising.
Achieving profitability was a significant milestone for us, highlighted when we closed our June 2023 books with a modest profit of $113, paving the way for sustained growth.
What challenges and surprises should entrepreneurs in this field expect?
Medalie: The challenge of formulating truly natural products, especially in the beauty industry, cannot be overstated. We quickly learned why many predecessors opted for shortcuts in formulation—they often lead to more reliable results. Our commitment to authenticity brought unexpected hurdles, from ingredient instability to shorter shelf lives than conventional products. Despite significant losses due to batch failures, we ultimately emerged with a renewed vision for sustainable beauty.
Can you share a specific incident where you faced a setback and how you overcame it?
Whiteside: Although we haven’t raised a multi-million-dollar investment yet, we’ve encountered significant cash flow obstacles. Following our friends and family round, we faced a challenging period where we were losing around $10,000 monthly while we worked to optimize costs and marketing.
We believed we had a promising investment secured, but the deal took months to materialize and ultimately fell through, depleting our funds. We had to make tough decisions, such as pausing salaries and cutting expenses ruthlessly, testing our resolve and pushing us to rethink our growth strategy.
Medalie: In response, we adapted by raising smaller amounts of capital than anticipated but managed to stay afloat. This experience forced us to streamline operations and reach cash-flow positivity, solidifying our ownership stake in the company. A vital lesson emerged: fundraising is not real until funds are in your account.
When did you begin to see consistent monthly revenue, and what does growth look like now?
Whiteside and Medalie: We didn’t achieve consistent monthly revenue—around $10,000 to $20,000—until mid-2023. The venture commenced in 2021, when we produced our Glacial Clay Pomade in a humble kitchen setup, selling directly to consumers and salons. In the early years, our earnings fluctuated between $1,000 and $3,000 per month.
Now, in 2025, after launching a third product line, we celebrated our first million-dollar month and have maintained profitability for almost two years. This journey reinforces that success is not instantaneous—often taking five to ten years.
What do you find most rewarding about running Highland?
Medalie: Surprisingly, the highlight is sharing this journey with loved ones. While people often caution against mixing business with friendship, we find it rewarding and enjoyable. Each day presents new challenges and opportunities to grow together.
Whiteside: My greatest satisfaction comes from tackling complex problems alongside my best friend and co-founder. The freedom to chart our path and take on challenges bolsters our collective sense of purpose. Being your own boss is both demanding and the most liberating aspect of entrepreneurship.
What is your best piece of actionable business advice?
Whiteside: Initiating a venture can be daunting, but I advise focusing intently on your strategic roadmap. A mentor once told me, “Beware the incoming call,” emphasizing that distractions can derail you from your objectives. While it’s important to remain open to new possibilities, it’s crucial to stay aligned with your vision and diligently work to bring that to fruition.
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