We recently connected with Jon Skubis and have shared our conversation below.

Jon, thanks for joining us, excited to have you contributing your stories and insights. What do you think it takes to be successful?

To me, success is persistence over perfection. It’s showing up when everything feels like it’s falling apart, when money’s tight, a launch flops, or you start questioning whether you’re crazy for chasing your vision. It’s not glamorous. It’s a war of attrition. Most people quit long before they get close. People love the “overnight success” story. What they don’t see are the years of grinding it out, the sleepless nights, and the moments when you seriously consider giving up. That’s the real story behind most entrepreneurs.
When we started Sierra Whiskey Co., we didn’t have outside investors or industry connections. Just conviction, and an idea: build tough, reliable gear for men who actually give a damn. And when you’re bootstrapping a product-based business, you hit brutal cashflow bottlenecks. Things can be working perfectly — inventory moving, customer feedback strong, marketing firing — and you still find yourself strapped for capital. Growth creates its own pressure.
That’s one of the hardest parts of entrepreneurship no one talks about. You’re constantly asking: “Where does the next dollar go, inventory? Ads? R&D?” It’s like walking up to the roulette table with your life’s work and putting it all on red, again and again, hoping your bet on the future pays off.
And when sales slow, self-doubt creeps in. You tie your identity to the business without realizing it. When things are up, you’re flying. When they dip, you’re wondering what you screwed up.
What it really takes to succeed? Relentlessness. Fix problems as they come. Stay mission-focused. Tell the truth. And never forget who you’re building for.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’m a former government sales director who worked with Tier 1 military units and special operations groups. I’ve spent years around men who operate at the highest levels, men who value grit, discipline, and integrity. And one day I realized: the gear they wore, the basics, like underwear, socks, and tees, was mostly garbage. Overpriced. Weak. Designed by marketing departments, not people who actually use the gear. So I started Sierra Whiskey Co. with one mission:
Build premium performance apparel for men who still believe in honor, courage, and country. No fluff. No virtue signaling. Just gear that’s built to perform, and built to last.
Our flagship product is Undertac Tactical Underwear, which includes a hidden Escape & Evasion Pocket, originally inspired by Special Forces operators and tested by those same men in one of the harshest terrains, Africa. We’ve since expanded into FURY PT socks, Exfil Boot Socks, rugged EDC tees, premium hoodies, and a full line of apparel designed for everyday freedom-focused living.
What sets us apart?
Everything we make is built with function and purpose — not trend chasing. Most of our products are made in the USA, and the ones that aren’t are tested relentlessly and vetted for performance. We don’t apologize for being pro-America, pro-freedom, and pro-free speech. And we’re proud to donate a portion of profits to veteran-run organizations fighting human trafficking.
Our customers aren’t chasing hype, they’re living life with intent. Whether they’re veterans, backcountry hunters, first responders, ranchers, small business owners, blue collar workers, firefighters, or just guys who still stand for something, we make gear that’s got their back.
What am I most proud of?
We’ve built Sierra Whiskey Co. from the ground up with no outside investors, no fancy marketing agency, and no safety net. Just hard work, loyal customers, and a mission worth building around. Every time a customer tells us our gear served them perfectly during a deployment, a ruck, on duty, a 105 degree workday, or just made them feel damn proud to wear it, that’s the win.
If there’s one thing I want you to know, it’s this:
We’re not just selling apparel. We’re building a movement of men who still give a damn, and we’ve got the gear to prove it.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

I used to believe that if you built the best damn product possible, the market would just show up. So that’s what I did. I obsessed over the design, tested it in brutal conditions, and had some of the toughest men on the planet run it through hell in one of the harshest places on Earth. They loved it. I thought, “We’re about to have a big problem… how the hell are we going to keep up with all the orders?” Then… crickets.
A few friends bought. A couple family members. And that was it.
That’s when the lesson hit me hard: You can have the best product in the world, but if no one knows about it, they can’t buy it.
Marketing isn’t optional, it’s everything.
You’ve heard the cliché: awareness is the top of the funnel. But it’s not a cliché because it’s wrong. It’s a cliché because most people learn it the hard way, just like I did.
It’s like being the greatest artist on Earth and locking your masterpiece in the garage. Doesn’t matter how good it is, if no one sees it, no one knows it exists. That’s the mistake I made. I put everything into building the perfect product, but I didn’t save enough gas in the tank to let the world know it was there.
So I cashed out my retirement fund and went all in on learning how to market. And yeah, it felt like legal gambling. Some things worked. Some didn’t. Some campaigns that looked bulletproof flopped. Others I had zero faith in turned into five-figure weeks. That’s the game.
What I learned is this:
A great product is the foundation of a real business, but without marketing, it’s just a well-kept secret.
I used to loathe marketing, with so many companies it felt cheap and tacky. Marketing isn’t a dirty word. It’s really just potential customer education if you do it right. It’s how you earn attention, build trust, and give people the chance to try your masterpiece. And if you’re lucky, and relentless, they’ll come back for more. The trust is not given, it’s earned.

What else should we know about how you took your side hustle and scaled it up into what it is today?

Absolutely, though not in the way I planned. Originally, Sierra Whiskey Co. was meant to be a slow-burn side hustle. The idea was to build it gradually while keeping my full-time job until it could stand on its own. Safe, smart, steady. Then 2020 hit.
We’d just launched the business, but it wasn’t doing much yet, partly because I hadn’t learned the most important lesson: marketing matters. I remember thinking, “Well, at least I still have my job.” It was the start of “two weeks to slow the spread,” which turned into working from home for a month… and then the world started to feel upside down.
Then I got the call.
No warning. No feedback. No reason. Just: “Thanks for your service to the company. If you sign an NDA, we’ll give you two months’ severance.”
That was it. I got downsized, a week after the company had just announced that no one would be losing their job. Half my team was let go. I’d been breaking sales records, doubling performance targets… and none of it mattered.
So I had a choice: panic or bet on myself.
I cashed out my retirement account and went all in on Sierra Whiskey Co. No backup plan. No guarantees. Just the fire to build something real. It wasn’t some overnight success story, it took a solid year of trial and error to find the right marketing and reach the right audience.
I’ll never forget that first major campaign. The media company wanted me to prepay for four ad spots, and each one cost more than I’d paid for my car. It felt like walking up to a roulette table and putting everything on red.
By the grace of God, it worked. Orders started coming in. I scaled it from there. Slowly, painfully, methodically.
And here we are.
There’s been no shortage of tough lessons, but I’ve never looked back. Getting laid off was one of the best worst things that ever happened to me. It forced me to take control. Now, I don’t answer to a boss, I answer to my customers. Tens of thousands of them. And there’s a kind of freedom and responsibility in that that I wouldn’t trade for anything.
I get to serve the best damn people on earth. That’s the mission now. And I couldn’t be more grateful for it.

Contact Info:

• Website: https://www.sierrawhiskeyco.com/
• Instagram: https://www.instagram.com/sierrawhiskeyco/?hl=en
• Facebook: https://www.facebook.com/SierraWhiskeyCo/
• Twitter: https://x.com/sierrawhiskeyco
• Youtube: https://www.youtube.com/c/sierrawhiskeyco