Brian Smith tried to quit. Multiple times. He literally could not go out of business.
Every time he was ready to walk away from UGG — the sheepskin boot company he'd started out of the trunk of his car — the phone would ring. Twenty messages from surf shop owners: "Brian, the store's been full of people asking for UGGs today. I've run out. Can I come get more?"
As Brian told me on The Decidedly Podcast: "I realized I can't even go out of business properly. So I figured if I can't quit, I'm gonna have to make a really big move here and create a proper company."
That proper company eventually became a global brand worth hundreds of millions. And Brian's journey from car-trunk startup to successful exit is one of the best case studies I've ever heard on what it takes to build — and sell — something real.
The demand was there. The plan wasn't.
Brian had an incredible product. Americans just didn't understand sheepskin boots yet. Surf shops didn't have the money for big inventory. Ski shops were the same story. And to sell one pair of size 10, you needed sizes 6 through 12 on the shelf because you don't know what's walking through the door.
The product was expensive, the financing was brutal, and Brian was working on a golf course during the summers just to stay alive.
Sound familiar? A lot of business owners I work with are in a version of this. They've built something valuable, but the business runs on willpower instead of systems. The demand is real, but the infrastructure isn't there to capture it — let alone sell it.
Relationships drove every key decision.
One of the things that struck my dad Shawn and me the most was how every critical moment in UGG's story came back to a relationship. Brian's partnership with the guy selling flip-flops — they had inverse seasonality, which was brilliant. His knowing when to bring someone into a negotiation and when to keep them out.
Every key decision point in the progression of that company — all the way through the sale — ties back to a relationship. Knowing when to draw somebody close and when to do the opposite.
For business owners thinking about their own exit, this is critical. Your relationships are part of your business value. Your clients' trust, your team's loyalty, your vendor partnerships — these aren't just nice-to-haves. They're what a buyer is paying for.
The struggles never go away.
My biggest takeaway from Brian's story is that the challenges don't disappear as you grow. Brian struggled to raise capital at the beginning, and he struggled to raise capital later. Different amounts, different stakes, same fundamental tension.
If you're waiting for things to "settle down" before you start planning your exit, you'll wait forever. There's no magical moment when the business runs itself and you can calmly think about the future. The best time to plan is while you're in the thick of it — because that's the only time there is.
What this means for you.
You don't have to be building the next UGG for these lessons to apply. Whether your business does $500,000 or $50 million, the principles are the same:
- You can't sell what you haven't built properly. Brian had to turn a hustle into a company before anyone would buy it. Do you have documented processes, a team that can operate without you, and clean financials?
- Relationships are assets. Transferable client and vendor relationships increase your business value. Personal relationships that only you hold decrease it.
- Don't wait for comfort. Start your exit planning while the business is strong, not when you're burned out.
- Know what you're going toward. Brian didn't just sell UGG and disappear. He had a next chapter. Do you?
Start the conversation.
If Brian Smith had quit UGG that summer on the golf course, nobody would know his name. The boots would be gone. The brand would be gone. Hundreds of millions in value — gone.
He didn't quit. But more importantly, when it was time, he had a plan to exit.
If you're a business owner and you've been thinking about what comes next — even casually — I'd love to have that conversation with you. Book a free conversation and let's talk about your five key decisions.
This article is based on a conversation from The Decidedly Podcast. Insights, advice, and comments provided by Sanger Smith, Shawn Smith, and guest speakers should not be considered personalized financial advice or recommendations. This content is produced solely for informational and educational purposes. For personalized guidance, book a free conversation.
