Before we jump in:
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I had breakfast with a mentor of mine in Ithaca, New York the summer after I started my first business. He ran the entrepreneurship program at Cornell.
Two minutes in, before he'd even asked what I wanted to order, he asked me a question. "Nick, do you like sales? Would you consider yourself a good salesman?"
I could tell he wanted me to say yes. I was honest instead and I said no, I don't like confrontation, I don't like rejection, I'm more of a visionary, an operator, the guy at the whiteboard. I spent two or three minutes trying to explain why sales wasn't really my thing.
He rolled his eyes and said, "Nick, if you don't like sales, you need to go get a job now!"
I was 23, running a pick up and delivery student storage business with no cash, and he walked me through exactly why sales was crucial for my success.
How was I going to convince someone to lease me a warehouse?
How was I going to convince U-Haul to give me credit on trucks?
How was I going to convince a box company to sell me $20,000 of inventory with no money down?
How was I going to convince twenty employees to join a company that might not make payroll, when they could go wait tables for the same money with none of the risk?
He never even got to customers, because by then I already understood the point.
I walked out of that breakfast wanting to crawl into a hole.
It took about two weeks for the lesson to fully click. Life is all about sales.
So I went to work and I learned to sell.
The next fifteen years have been all about getting in more reps.
You don't get strong by watching workout videos, you get strong by going to the gym and lifting the damn weights, so I put myself in hard sales situations early and kept going instead of quitting, which is what most people do the moment it gets uncomfortable.
Somewhere in those years I landed on a framework that still works for me.
The old school pitch is to talk up all of the positives and go for the close, but I've had far more luck doing the opposite.
Instead, you should show people you know your stuff, then tell them what could go wrong before they ask.
When I was raising money for storage deals at 25, I'd tell investors exactly what worried me, the debt risk, the operational risk, what happens if rates double and we're stuck for a decade.
Then I'd go quiet and ask, "So why are you still interested?"
More often than not, they'd sell themselves, because naming the downside up front is how you avoid creating expectations you can't live up to later.
This builds enormous trust before you ever make the ask.
A few years later, I had a wealth manager friend named Jim sit me down in his conference room. He spent a full hour breaking down my entire financial life for free. He didn't try to pitch me. He was just giving away free value.
He told me the people who walk into his office already have money and influence. He doesn't sell them on the first meeting, he builds trust first.
He told me that 30-40% sign up on the spot anyway. The rest call him back six months later when a new problem hits and they sign up then.
It was the same lesson my mentor in Ithaca had given me at that breakfast, just from the other side of the table.
You have to prove that you're worth trusting before you ever ask for anything.
I still use both halves of that lesson today, even when I'm the one buying instead of selling.
I recently mailed a handwritten note to a self-storage owner in Ohio not too long ago. It said "My name is Nick, I own a storage company, I'd love to talk if you're open to it." and then it had my contact information.
Weeks later they called, and I spent 45 minutes being asked about my values, my background, my family, before they'd even consider my offer.
They weren't going to hand over their life's work to just anybody, which meant that even as the buyer with the checkbook, I had to sell myself on why I was the right fit.
You have to understand that getting people to trust you and to want to do business with you is sales, whether you're buying or selling, whether it's a warehouse lease or a marriage.
Everything in life is about getting better at and utilizing the skill of sales.
If you feel uncomfortable about trying to make a sale, you need to practice the muscle and put in the reps. Nobody is born good at it. I wasn't, but I practiced, I learned, I improved, and ultimately sales became the foundation of everything I have built today.
Onward and upward,
Nick
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A few posts from this week.
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Onward and upward,
Nick Huber
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