This Side Hustle Spotlight Q&A features Colorado-based entrepreneurs Boone Whiteside, 29, and Ben Medalie, 28. Whiteside and Medalie are the co-founders of Highland, a haircare brand that started as a DIY passion project in a Denver apartment and has grown into an eight-figure business in three years. Responses have been edited for length and clarity.

^{Image Credit: Courtesy of Highland. Boone Whiteside, left, and Ben Medalie, right.}
When did you start your side hustle, and where did you find the inspiration for it?
Whiteside: When Ben and I became best friends during our junior year at CU Boulder, one of the things that brought us close was our shared aspiration of building our own thing — in not walking a 9-5 path working on someone else’s dream. This shared passion wouldn’t manifest until much later, though.

When I first started dreaming of a hair product company that went beyond styling one’s hair with toxic sh*t, I was working at an ecommerce startup in a marketing and operations role. We were a small team, and the company was struggling hard to establish itself. I learned a ton about problem-solving through the early stages of business, but I had one foot out the door, pulling me toward my calling of being my own entrepreneur.

Related: This 17-Year-Old High School Student Has a $20,000-a-Month Side Hustle — and It All Started With a Skill He Learned in Class

Ben was working at a payroll tech company in an analyst role, but the actual role changed so much during his tenure because he hated doing the same thing every day. Juggling sales, learning to code, handling risk analysis, dabbling in marketing and growth… his managers were constantly breathing down his neck to “JUST FOCUS” on “his main role.” Neither of us were happy with those career trajectories.

Sick of the archaic legacy brands that dominated the hair styling space with cheap, chemical-based formulations and wasteful packaging, and unsuccessful in my search for a brand that was disrupting the industry, I stumbled into an idea that would solve my own consumer need. I had a hunch this problem would resonate with people like me.

What were some of the first steps you took to get the side hustle off the ground?
Whiteside: The first steps were hitting the Google machine (BAI, or before AI) to uncover naturally occurring, plant-based ingredients that could replace plastic, endocrine-disrupting formulas. Without a lick of chemistry or cooking experience to my name, I began ordering waxes, clays, oils and other botanical ingredients and started mixing them on my stovetop.

Fortunately I’ve always been a weirdo, so I was weird enough to start putting these failed concoctions into my hair, weird enough to make all of my friends do the same and give me feedback and weird enough to be unbothered by my roommate, Ben telling me how weird I am… soon to become a hair weirdo himself.

^{Image Credit: Courtesy of Highland}

Are there any free or paid resources that have been especially helpful for you in starting and running this business?
Medalie: Some tech standouts include: Klaviyo for email marketing, Shopify (and all its awesome plugins) to power our site, Triple Whale for attribution metrics, Amped (now Mailchimp) for lead capture, Adobe Premiere for content creation and finally Figma for making the non-designer look and feel like Rembrandt.

Whiteside: Ben covered most of the paid ones. For free, the best resource we tapped into was our polite persistence in demanding help from other business builders. People generally want to help, but you can’t be afraid to ask. We recently grabbed coffee with Justin Gold, founder of Justin’s, the peanut butter brand, and he summed it up nicely: “Be unreasonable.” This mentality has been instrumental in building an unbelievably helpful network of people who have helped us build the Highland strategy from the ground up and in avoiding mistakes other founders have made. So go be unreasonable — just be polite about it.

Related: This Couple Started a Side Hustle to Improve a ‘Terribly Made’ Bathroom Essential. Now the Business Earns More Than $3 Million a Year.

If you could go back in your business journey and change one process or approach, what would it be, and how do you wish you’d done it differently?
Whiteside: I think Highland gets high marks for doing this early, but I wish we’d done it even earlier. Get very serious about your unit economics from day one. Learn what your gross margins are. Make a plan for how you will bring down COGs over time, and know that every penny counts. Get serious about your finances, and figure out how and when you can make your business profitable. For now, the days of raising capital and figuring out how to become profitable later are gone, as are most of the businesses that took this route.

One of the most magical days of Highland was when the June 2023 books closed, and we had $113 in profit. We’d figured out how to make the business self-sustaining, and that meant our runway was unlimited. Become profitable, don’t die, then figure out how to effectively scale.

But also, no regrets. The journey was the journey, and it shaped us. Let yours shape you.

When it comes to this specific business, what is something you’ve found particularly challenging and/or surprising that people who get into this type of work should be prepared for, but likely aren’t?
Medalie: Formulations (of any kind, but especially in beauty) that are truly natural are incredibly hard to get right. We learned fast why all of those who came before us cut the corners they did, and we were offered the same formulation shortcuts that ensure consistency and so-called “performance.”

In being adamant that our products would be different, we ran into issues left and right. Our ingredients are volatile and misbehaving; early batches would vary greatly, and they had a much shorter shelf life than the products we were going up against. Multiple times, we lost thousands of units to failed batches, went out of stock as a result and questioned if it was all worth it. In the end, we broke through on the other side of this challenge, now redefining what innovation is possible within “better for you, better for the planet” formulation.

^{Image Credit: Courtesy of Highland}

Can you recall a specific instance when something went very wrong? How did you fix it?
Whiteside: We’ve never raised a multi-million-dollar round — at least, not yet — but that hasn’t spared us from facing serious cash flow challenges. Right after our friends and family round, we hit a rough patch. We were burning about $10,000 a month as we worked toward reducing our losses and slowly ramped up our marketing spend. Still, we weren’t too worried. We had three months of runway and what felt like the perfect investor lined up — someone ready to write the full check and bring industry expertise and mentorship that Ben and I had only ever hoped for. We were set. Until, suddenly, we weren’t.

The process dragged on for months. Our bank account drained. The deal ultimately fell through. We had to stop paying ourselves, cut expenses to the bone, delay growth plans and strain relationships with our manufacturing partners. It was the first time we really confronted the possibility of losing the company, and it was a gut check.

Medalie: So, we scrambled. We raised less capital than we had planned, but we made it work. We kept a confident front for our investors, got lean and stayed scrappy. Looking back, it was one of the best things that could’ve happened. It forced us to prove our path to becoming cash-flow positive and helped us retain more ownership. But it was a hard-earned lesson: Fundraising isn’t real until the money hits the bank. And no matter how promising a deal looks, you can’t build a business on potential alone.

Related: After Losing $5 Million Overnight at Age 25, He Started a Business on Track for $50 Million. Here’s the ‘Lightbulb Moment’ That Made It Happen.

How long did it take you to see consistent monthly revenue? How much did the side hustle earn? What does growth and revenue look like now?
Whitside and Medalie: We didn’t start earning consistent monthly revenue ($10,000-$20,000 per month) until mid-2023. The side hustle kicked off all the way back in 2021, when Ben and I were making the batches of our Glacial Clay Pomade in our KitchenAid mixer, packing the units by hand and selling them on our Shopify storefront and to a couple of salons and barbershops. The side hustle probably generated an average of $1,000-$3,000 a month between 2021 and 2023.

Now in 2025, after launching our third-ever SKU, we hit our first million-dollar month and have been profitable for nearly two years straight. It’s not a race. Become an overnight success in five to 10 years.

What do you enjoy most about running this business?
Medalie: Honestly, hot take… getting to do this whole thing with the people we love and cherish most in life. People always warn against getting into business with best friends or family, but this part has been the most fun. Every single day is different, and getting to see yourself and friends grow, thrive and even fail in front of each other is incredibly powerful and motivating.

Whiteside: What I enjoy most is waking up each day with a purpose, solving challenging problems with my best friend and co-founder and choosing our own adventure in every facet of what we do. Being your own boss is NOT an overrated part of being an entrepreneur. It’s incredibly hard, but it’s also the best.

^{Image Credit: Courtesy of Highland}

What is your best piece of specific, actionable business advice?
Whiteside: Getting started is often the hardest part, but if someone has, I’d offer a piece of advice from my dear friend and Shopbop founder, Bob Lamey: “Beware the incoming call.” It means to be laser-focused on what you think the roadmap is for your business and striving toward those goals with intention. Many emails, phone calls, pitches and day-to-day tasks become a distraction from what you know you need to be working on.

This doesn’t mean to ignore opportunities as they arise — it is a call to define your vision and hold yourself accountable in working to bring it to life. You know what you need to be doing; don’t let the noise distract you.