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ShearShare's founders climbed Mount Kilimanjaro. Here's what they learned.


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The Caldwells at the top of Mount Kilimanjaro.
Courtney & Dr. Tye Caldwell

As Courtney Caldwell stood more than 19,000 feet above sea level, she felt at peace.

She was surrounded by glaciers and pure white snow. The scene looked like uncharted territory with few people and no sense of time or a reason to rush, just like heaven.

They’d done it. Courtney and her husband, Tye, had climbed Mount Kilimanjaro.

“What you see at the top, you won’t see looking at the mountains,” she said. “You’re up there in the clouds.”

It’s not the first mountain the Caldwells have climbed together. They’ve done marriage together, parented together, and together they started ShearShare, a web-based platform that connects barbers and stylists with empty chairs at existing salons. Last year, they moved to Buffalo together after winning $500,000 in the 2021 43North competition.

The more they reflected on the seven-day mountain journey, which they took in December, the more similarities they see between their trying trek and running a startup.

“It’s overwhelming to see what you’re getting ready to tackle,” Tye said. “We stayed close to one another, valued our opinions and thoughts. … We know we can be champions for one another.”

• • •

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A team helped the group of travelers climb Mount Kilimanjaro.
Courtney & Dr. Tye Caldwell

To make the decision (let alone actually finish the journey) to climb Mount Kilimanjaro, the world’s largest free-standing mountain, the Caldwells had to have the right environment, the right team.

They didn’t do it alone. They had a crew of 27 people, from porters to guides to cooks, helping them up the mountain.

They also had the camaraderie and support of the group they were trekking with, which included Mike Wisler, M&T Bank chief information officer and member of the 43North board of directors. He had climbed Mount Kilimanjaro before and was used as a sounding board” for those who hadn’t completed the journey before.

The seven-day climb up and then down the mountain in Tanzania was a slow trek. Every time they passed someone along the way, they were met with the friendly Swahili greeting “jambo jambo” and “pole pole,” which means go slow.

“You have to just put one foot in front of the other and focus on the risk that you can control,” Courtney said.

The same can be said for running a tech startup. It's crucial to have the right team and great mentors who have been on the same path as you.

Along the way, slow growth is good growth. Not everything will be in your control — like an international pandemic, for example — but focus on the risk that you can control.

“Your journey won’t look the same as everyone else’s,” said Tye.

• • •

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Tye Caldwell during his Mount Kilimanjaro trek.
Courtney & Dr. Tye Caldwell

Climbing over 19,000 feet takes climbers through a wide range of terrain and weather conditions. The Caldwells experienced sweltering heat, rainforest, moorland and, of course, the top of the mountain.

At its peak, Mount Kilimanjaro is freezing and snowy, but because it’s so close to the sun, it’s also very bright.

As they climbed, the Caldwells gradually put on layers, from shorts to pants, adding on a raincoat and then a winter coat. By the time they got to the top, Courtney said, she had three layers, a coat and face goggles, and she was still freezing.

To battle the cold at night, they stuffed hot water bottles into the bottom of their sleeping bags along with their clothes for the following day. That way, they’d be putting on warm clothes in the morning.

“That’s life in general,” Courtney said. “The business slapping you across the face, but you still have to do what you can for your users.”

With a looming economy and companies doing layoffs, entrepreneurs must adjust to each changing condition, sometimes adding a layer and sometimes removing one.

“Do what you have to do to keep the company alive,” Tye added.

• • •

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The Caldwells climbed Mount Kilimanjaro last month.
Courtney & Dr. Tye Caldwell

The goal of their journey was clear: reach the top of Mount Kilimanjaro.

It’s a lofty plan in and of itself, but naturally there were challenges to overcome along the way and unexpected struggles.

Like day four, when they faced the Barranco Wall, over 800 feet high, and had to tackle steep and narrow paths that require using all four limbs to navigate. Some maneuvers involved climbing down in order to continue ascending the wall.

Or day six, when they reached Stella Point and had about 45 more minutes to go before reaching the top of the mountain. But they had already been climbing for several hours that day, starting at midnight, and they were so high up that the air was low on oxygen.

“It’s not about how fast you’re going,” Tye said. “It’s about rest, walking. I think a couple times I walked five steps and rested. It was a challenge.”

“For me, getting up to the summit was a big deal,” Courtney added. “That was the goal. No one had to remind each other of that. There were so many other accomplishments you’ll run into, though.”

For a tech startup, there are obvious goals, like raising funding and hiring staff, as well as bigger-picture goals like getting acquired or going public. There are stepping stones along the way, but there are also unexpected triumphs that should be celebrated

The Caldwells didn’t plan on being a married couple who run a startup or to represent minority-owned businesses successfully raising money. But they celebrate those parts of their story.

“Whatever comes of it, we’re going to be ready,” said Tye. “We’re excited for what’s to come."


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