This Aspect Hustle Highlight Q&A options Colorado-based entrepreneurs Boone Whiteside, 29, and Ben Medalie, 28. Whiteside and Medalie are the co-founders of Highland, a haircare model that began as a DIY ardour venture in a Denver residence and has grown into an eight-figure enterprise in three years. Responses have been edited for size and readability.
Picture Credit score: Courtesy of Highland. Boone Whiteside, left, and Ben Medalie, proper.
When did you begin your aspect hustle, and the place did you discover the inspiration for it?
Whiteside: When Ben and I turned finest pals throughout our junior 12 months at CU Boulder, one of many issues that introduced us shut was our shared aspiration of constructing our personal factor — in not strolling a 9-5 path engaged on another person’s dream. This shared ardour would not manifest till a lot later, although.
After I first began dreaming of a hair product firm that went past styling one’s hair with poisonous sh*t, I used to be working at an ecommerce startup in a advertising and marketing and operations position. We have been a small workforce, and the corporate was struggling arduous to ascertain itself. I discovered a ton about problem-solving by the early levels of enterprise, however I had one foot out the door, pulling me towards my calling of being my very own entrepreneur.
Ben was working at a payroll tech firm in an analyst position, however the precise position modified a lot throughout his tenure as a result of he hated doing the identical factor day-after-day. Juggling gross sales, learning to code, dealing with danger evaluation, dabbling in advertising and marketing and progress… his managers have been consistently respiration down his neck to “JUST FOCUS” on “his important position.” Neither of us have been proud of these profession trajectories.
Sick of the archaic legacy manufacturers that dominated the hair styling house with low-cost, chemical-based formulations and wasteful packaging, and unsuccessful in my seek for a model that was disrupting the trade, I stumbled into an concept that may remedy my very own client want. I had a hunch this drawback would resonate with individuals like me.
What have been among the first steps you took to get the aspect hustle off the bottom?
Whiteside: The primary steps have been hitting the Google machine (BAI, or earlier than AI) to uncover naturally occurring, plant-based components that might substitute plastic, endocrine-disrupting formulation. And not using a lick of chemistry or cooking expertise to my identify, I started ordering waxes, clays, oils and different botanical components and began mixing them on my stovetop.
Happily I’ve all the time been a weirdo, so I used to be bizarre sufficient to begin placing these failed concoctions into my hair, bizarre sufficient to make all of my pals do the identical and provides me suggestions and peculiar sufficient to be unbothered by my roommate, Ben telling me how bizarre I’m… quickly to develop into a hair weirdo himself.
Picture Credit score: Courtesy of Highland
Are there any free or paid sources which have been particularly useful for you in beginning and working this enterprise?
Medalie: Some tech standouts embrace: Klaviyo for e-mail advertising and marketing, Shopify (and all its superior plugins) to energy our website, Triple Whale for attribution metrics, Amped (now Mailchimp) for lead seize, Adobe Premiere for content material creation and at last Figma for making the non-designer feel and appear like Rembrandt.
Whiteside: Ben lined many of the paid ones. Without spending a dime, the most effective useful resource we tapped into was our well mannered persistence in demanding assist from different enterprise builders. Folks typically need to assist, however you’ll be able to’t be afraid to ask. We lately grabbed espresso with Justin Gold, founding father of Justin’s, the peanut butter model, and he summed it up properly: “Be unreasonable.” This mentality has been instrumental in constructing an unbelievably useful community of people that have helped us construct the Highland technique from the bottom up and in avoiding errors different founders have made. So go be unreasonable — simply be well mannered about it.
When you may return in your online business journey and alter one course of or method, what wouldn’t it be, and the way do you would like you’d finished it otherwise?
Whiteside: I feel Highland will get excessive marks for doing this early, however I want we would finished it even earlier. Get very critical about your unit economics from day one. Study what your gross margins are. Make a plan for a way you’ll carry down COGs over time, and know that each penny counts. Get critical about your funds, and determine how and when you may make your online business worthwhile. For now, the times of elevating capital and determining easy methods to develop into worthwhile later are gone, as are many of the companies that took this route.
Some of the magical days of Highland was when the June 2023 books closed, and we had $113 in revenue. We would discovered easy methods to make the enterprise self-sustaining, and that meant our runway was limitless. Become profitable, do not die, then determine easy methods to successfully scale.
But in addition, no regrets. The journey was the journey, and it formed us. Let yours form you.
Relating to this particular enterprise, what’s one thing you have discovered significantly difficult and/or shocking that individuals who get into one of these work ought to be ready for, however seemingly aren’t?
Medalie: Formulations (of any form, however particularly in magnificence) which are actually pure are extremely arduous to get proper. We discovered quick why all of those that got here earlier than us reduce the corners they did, and we have been provided the identical formulation shortcuts that guarantee consistency and so-called “efficiency.”
In being adamant that our merchandise could be completely different, we bumped into points left and proper. Our components are unstable and misbehaving; early batches would range significantly, they usually had a a lot shorter shelf life than the merchandise we have been going up in opposition to. A number of instances, we misplaced 1000’s of items to failed batches, went out of inventory consequently and questioned if it was all price it. In the long run, we broke by on the opposite aspect of this problem, now redefining what innovation is feasible inside “higher for you, higher for the planet” formulation.
Picture Credit score: Courtesy of Highland
Are you able to recall a selected occasion when one thing went very flawed? How did you repair it?
Whiteside: We have by no means raised a multi-million-dollar spherical — not less than, not but — however that hasn’t spared us from dealing with critical money stream challenges. Proper after our family and friends spherical, we hit a tough patch. We have been burning about $10,000 a month as we labored towards decreasing our losses and slowly ramped up our marketing spend. Nonetheless, we weren’t too frightened. We had three months of runway and what felt like the proper investor lined up — somebody prepared to write down the total examine and produce trade experience and mentorship that Ben and I had solely ever hoped for. We have been set. Till, all of a sudden, we weren’t.
The method dragged on for months. Our checking account drained. The deal in the end fell by. We needed to cease paying ourselves, reduce bills to the bone, delay progress plans and pressure relationships with our manufacturing companions. It was the primary time we actually confronted the potential of dropping the corporate, and it was a intestine examine.
Medalie: So, we scrambled. We raised much less capital than we had deliberate, however we made it work. We stored a assured entrance for our buyers, obtained lean and stayed scrappy. Wanting again, it was top-of-the-line issues that might’ve occurred. It pressured us to show our path to changing into cash-flow optimistic and helped us retain extra possession. However it was a hard-earned lesson: Fundraising is not actual till the cash hits the financial institution. And regardless of how promising a deal appears to be like, you’ll be able to’t construct a enterprise on potential alone.
How lengthy did it take you to see constant month-to-month income? How a lot did the aspect hustle earn? What does progress and income seem like now?
Whitside and Medalie: We did not begin incomes constant month-to-month income ($10,000-$20,000 per thirty days) till mid-2023. The aspect hustle kicked off all the way in which again in 2021, when Ben and I have been making the batches of our Glacial Clay Pomade in our KitchenAid mixer, packing the items by hand and promoting them on our Shopify storefront and to a few salons and barbershops. The side hustle in all probability generated a mean 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 worthwhile for almost two years straight. It isn’t a race. Turn out to be an in a single day success in 5 to 10 years.
What do you take pleasure in most about working this enterprise?
Medalie: Truthfully, scorching take… getting to do that complete factor with the individuals we love and cherish most in life. Folks all the time warn in opposition to stepping into enterprise with finest pals or household, however this half has been probably the most enjoyable. Each single day is completely different, and attending to see your self and pals develop, thrive and even fail in entrance of one another is extremely highly effective and motivating.
Whiteside: What I take pleasure in most is waking up every day with a objective, fixing difficult issues with my finest good friend and co-founder and selecting our personal journey in each side of what we do. Being your own boss is NOT an overrated a part of being an entrepreneur. It is extremely arduous, but it surely’s additionally the most effective.
Picture Credit score: Courtesy of Highland
What’s your finest piece of particular, actionable enterprise recommendation?
Whiteside: Getting began is usually the toughest half, but when somebody has, I might provide a chunk of recommendation from my pricey good friend and Shopbop founder, Bob Lamey: “Beware the incoming name.” It means to be laser-focused on what you suppose the roadmap is for your online business and striving towards these objectives with intention. Many emails, cellphone calls, pitches and day-to-day duties develop into a distraction from what you should be engaged on.
This does not imply to disregard alternatives as they come up — it’s a name to define your vision and maintain your self accountable in working to carry it to life. You understand what you should be doing; do not let the noise distract you.
