What Climbing Kilimanjaro Taught Tyler Woodall About Running a 100-Person Company
I climbed Mount Kilimanjaro while running a company with more than a hundred people on the payroll.
Six days up to Uhuru Peak, 19,341 feet, and for most of it no signal at all. No Slack, no email, no “quick question” calls. Just walking slowly uphill and finding out, in real time, whether the business I’d built was a business or a very elaborate job.
The test you can’t fake
Every owner says their company could run without them. Almost none of them have checked.
A mountain checks for you. There’s no option to pop in for ten minutes and unblock somebody. Whatever is documented, gets done. Whatever lives only in your head, stops.
Here’s what I found when I came down:
What kept running: quoting, service requests, onboarding, payroll, client check-ins. Every process we’d actually written down and trained people against ran fine. Some of it ran better, because nobody was waiting on me to weigh in.
What stopped: every decision I’d never defined a rule for. Pricing exceptions. Anything a client escalated. Which clients got priority when two things landed at once. None of that was written anywhere. It was just me, and the team had learned to wait for me.
That list was the real output of the trip. Not the summit photo — the inventory of everywhere I was still the bottleneck.
Why I built the business that way on purpose
I’ve been to more than forty countries. Not after an exit, not on a sabbatical. Most of it was while running the company, from a laptop, in whatever time zone I landed in.
People hear that and assume it’s a story about discipline or hustle. It isn’t. It’s the whole argument behind what I do for a living.
If a business only works while you’re watching it, you don’t own a business. You own a job that happens to carry a lot of extra risk, because you can’t get sick, you can’t take a real vacation, and you certainly can’t sell it. Buyers aren’t paying for your personal work ethic. They’re paying for a thing that produces money without you in the chair.
Documented processes plus a trained team — much of mine remote — is what converts one into the other. I don’t have a cleverer answer than that. It’s just that most people never do it, because writing an SOP is boring and doing the task yourself is faster today.
The altitude version of delegation
There’s a thing guides on Kilimanjaro say constantly: pole pole. Slowly, slowly.
You climb far slower than feels necessary, for days, because going at the pace you could go is exactly how you end up turning back at 17,000 feet with altitude sickness. The people who summit are almost never the fittest. They’re the ones who accepted a frustratingly slow pace early.
Building a business that runs without you works the same way. Documenting a process takes four times as long as just doing the task. Training someone to quote properly takes weeks you don’t feel you have. Every week you’d go faster alone.
And then a year later one person is doing forty hours of your work, correctly, and you’re somewhere with no signal while the thing keeps running.
What I actually changed afterward
Three things, within a month of getting back:
- Wrote down every decision rule I’d been making by feel — pricing exceptions, escalation thresholds, who gets priority. If it lived only in my head, it became a documented rule with a named owner.
- Gave every recurring process a named owner, not a team. “The team handles it” means nobody handles it when you’re gone.
- Started treating my own absence as a test, not a risk. Now I’ll deliberately go dark for a few days to find the next bottleneck. It’s cheaper to find it on purpose than during an emergency.
The part that isn’t about business
I didn’t climb it to prove a point about delegation. That’s just what I learned.
I climbed it because of a line I’ve carried around for years: don’t tiptoe through life to arrive safely at death. I’d hit the version of success I’d been chasing — business running, money coming in, freedom on paper — and found I wasn’t especially happy. The things in my life I’d actually call joyful were almost never about money. They were about service, and about doing things that scared me a little.
That’s the question I ask every guest on my podcast now: how do you define success? Not the version you’d put on LinkedIn. The real one.
Most people, if they sit with it for a second, find they’re still running on a definition they set at twenty-five and never revisited. The mountain is a good place to notice that. So is anywhere with no signal.
Tyler Woodall is the founder of ScaleOps and Agency Aid. Read his story or browse more articles.