How We Built a Business That Ran Even When We Were an Ocean Away.

2 days ago
6 min read

We didn't just take a vacation from Hawaiian Vacations. We moved our whole life hundreds of miles away and found out our business didn't need us in the room after all.

In Anchorage, Alaska in the early 1980s, John started Hawaiian Vacations as a bootstrap operation, packaging Hawaii vacation rental condos, rental cars, and inter-island air into vacations for Alaskans who wanted out of the snow. I was his advisor from the start and later joined him in running the company. For years, the two of us led the whole operation. John negotiated all the contracts, signed every check and replaced burned-out light bulbs, while I did the hiring, marketing, and oversight of every department. We needed to be on hand to answer questions, put out fires, and generally guide the company every step of the way. We were the mom-and-pop operators, each of us wearing several hats at all times.

We grew that little tour business into a scheduled charter airline flying DC-8s, then widebody jets, carrying 30,000 to 35,000 passengers a year between Anchorage and Honolulu. Eight figures in annual revenue, eventually. But for the first dozen years, we were exhausted, unhealthy, and raising a young daughter who wasn't getting the best of either of us, because there was no “us” left over after the business took what it wanted.

We believed, like most owners do, that the business needed us on-site, that if we weren't there answering the questions and making the calls only we could make, everything would fall apart before lunch. For years, that belief was true, mostly because we'd built it to be true. We hadn't given anyone else the tools to make those calls.

Then came the moment that changed things for us. We realized the business wasn't fragile because it needed us; it was fragile because we'd never let it be anything else. I wrote more about that turning point in The Moment I Realized My Business Didn't Support the Life We Wanted, if you want the fuller version.

A business that needs you in every room isn't a business. It's a very demanding job you created for yourself.

Where in your business are you still the answer to every question — not because you have to be, but because no one's ever been trained or given the authority to answer it instead?

So we set out, deliberately, to build Hawaiian Vacations around six principles: systems, measuring performance, leverage, culture, team, and customer service. Not one of them optional, not one of them a quick fix. We worked on all six for years before the business could run without us being in the room.

Systems came first, and by systems I mean something specific: standardized policies people could actually find, training that didn't live only in our heads, and enough documentation that a decision could get made by looking something up instead of hunting one of us down. We mapped almost everything we did, eventually, and it's still the piece I'd tell any owner to start with. I walked through more of that process in We Mapped Every Process in Our Business and Gained New-Found Freedom.

If a decision requires finding you, you haven't built a system. You've built a bottleneck with your name on it.

If you disappeared for a week starting tomorrow, how many decisions in your business would simply wait for you to come back?

Back then, we could not buy a ready-made automated online reservation system. We had to custom design one just for us. It cost us over six figures and took two years of development. Expensive, slow, yet it was the single best form of leverage we ever employed. We no longer faced the constraint of needing reservations staff on duty to take a booking. We didn't have to worry about long phone hold times or people waiting in our lobby for a free reservations agent. Bookings (and revenue) flowed in 24 hours a day, 7 days a week, even while we were sleeping!

That kind of leverage doesn't have to cost that much today; with what AI and automation can do now, most owners could build a version of that same freedom for a fraction of the cost and time, if they took the time to look for it.

If you're not sure where you're still doing work a system or a tool could be doing for you, the free Owner Diagnostic will show you in about three minutes what needs attention. It's the fastest way I know to see it in black and white.

I wrote more about what that kind of leverage actually bought us in How One Leveraging Tool Cut Overhead and Multiplied Revenue.

Leverage isn't the reward for scaling. It's the thing that makes scaling possible in the first place.

What's the one task in your business that, if you automated or delegated it tomorrow, would buy you back the most hours?

It took us about five years to build enough structure to hire a chief operating officer and a chief financial officer and actually step away from day-to-day operations. Five years of establishing systems, nurturing our culture, building our team, and creating daily, weekly, and monthly reports.

The reports gave us real numbers, not guesses, so we always knew how the business was doing even when we weren't there to watch it happen. And those reports did double duty. They told us the truth about the business, and they told our team the truth about themselves: how they were doing, where they stood, and what accountability actually looked like in real numbers, rather than vague feedback. That combination is what allowed us to trust the people we'd hired, and it's what I wrote about in The Moment I Knew Our Team Could Run the Business Without Us.

Trust but verify isn't a lack of faith in your team. It allows your faith to take root.

Does your team see the same clear numbers you do, or are you the only one who actually knows how the business is doing?

When we hired our COO and the CFO, we bought a second home on Maui, an ocean away from our company headquarters. We visited Maui frequently during the winter months and split the rest of our time between our Anchorage home and a yacht we cruised on in Alaska during the summers. And nothing broke!

So a few years later, we made a bigger move: we left Anchorage entirely and relocated to Sitka, Alaska, 600 air miles from the business we'd spent 25 years building.

And nothing happened. Actually, that's not quite true; what happened was the business kept growing, year over year, without us standing in the room making it happen. That's not luck. That's six principles, employed on purpose for years, before we ever tested them by putting a thousand miles between us and the day-to-day.

We didn't leave the business behind. We built it well enough that it didn't need us to stay.

If you moved hundreds of miles away tomorrow, would your business grow, or would it wait for you to come home?

This Week’s Exercise

Pick one decision this week that currently requires you personally, and write down who else could make it if given the right information.
Choose one process you've never documented and put it in writing, even roughly, before Friday.
Look at your last month of numbers and ask: could your team see this same report without you sending it to them?
If you took an unplanned week away starting Monday, list what would break, then pick one item off that list to fix first.

Final Thoughts

Back to the miles between Sitka and Anchorage: it wasn't the distance that made the business run without us. It was the five years before it — the systems, the reports, the team we trusted enough to hand real decisions to. The distance was just how we found out it had actually worked.

This week, pick one place where your business still needs you in the room, and start building the thing that would let it not need you there. You don't have to move hundreds of miles away to test it. You just have to be willing to find out what happens when you step back.

To your freedom,

Ral West

Livin’ the Dream