How She Left 25 Years of W-2 Life to Buy and Build a Tour Business in Hawaii

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Meet Tania.

Tania spent 25 years as an employee. Different industries, different titles, different companies. None of it really stuck.

"Any role I had, nothing was ever that satisfying. I always had side hustles because I felt this need for more autonomy and a sense of ownership."

Three years ago, she acquired a tour and transportation company operating across the Hawaiian Islands.

"Over the past three years, I've grown in my self-confidence. My decision-making. And interestingly, I am so much happier."

She's quick to add that it hasn't been easy. There are challenges regularly, every day.

"But because I'm in alignment with what I'm doing, it just feels right. The work doesn't feel hard. I'm just engrossed in what I'm doing."

After three years of ownership, here's where Tania stands:

This is the story of how she figured it out, one hard month at a time.

LESSON

The previous owner was retiring and had wound the business down significantly during COVID.

"In a way, it almost feels like a bit of a startup because he had pared it down so much. I really had a chance to kind of start fresh."

The business boasted some signature tours. A small fleet. A handful of CDL drivers. A lot of room to build. What it didn't have was much runway, and Tania's first and most expensive lesson was the importance of cash.

"Most of my available cash went into acquiring the business. If I had known about the Growth Boardroom before, I would have done things the smart way."

She hadn't fully accounted for how capital-intensive the day-to-day would actually be. Insurance adds up. Payroll for CDL drivers doesn't pause. Vehicles break down.

"The first two years, I was doing a lot of catch-up. Constant catch-up. I was amazed we would survive every month."

If she could do it over, she told us, she would have negotiated a lower upfront payment or a dedicated operating reserve after closing.

BREAKTHROUGH

Tania joined the Growth Boardroom right at the inflection point of a pivot to B2B. She had just landed lucrative cruise ship contracts, but cruise lines don't pay immediately.

That created a two-month window where money was going out on operations but not yet coming in from the new contracts.

Within the first weeks in the Boardroom, she learned how to leverage a 13-week cash flow forecast.

"To this day, it is the backbone of my business."

The tool gave her a framework to make daily decisions in real time: what had to be paid now, what could wait, where the gaps were forming. Eventually, she got through that window. The cruise ship revenue started flowing. The business stabilized.

"If I didn't have that, I don't think I would have been able to manage that very precarious time where there wasn't enough money coming in."

KEY DECISION

For the first year and a half, Tania kept her day job. But running a multi-island business while holding down a full-time W-2 is rough, to put it lightly.

She was living and working her day job on a different island from the one the business operated on. Logistically and mentally, she just couldn't be where she needed to be to grow the business.

"There was just a point where I stretched myself with trying to physically be at the job and then make time. The level of stress I had accumulated at that point, I was like, I just can't do this."

One weekend, something shifted.

"I had this identity shift. I just cannot go back to being an employee anymore. I'm just not one. I'm a business owner, and that's where I need to focus."

She had about six months of savings. She gave notice. She'll tell you it wasn't necessarily the "smartest" move.

But within four months, she was paying herself from the business. "Everything started to get better and better after that."

LESSON

Tania is a relationship builder. She has a background in marketing, spent time as a CRM administrator, and brings strong people and technology skills to the table.

What she is not, by her own assessment, is a daily tour business operator.

For two years, she acted like one anyway, doing everything except driving the buses and fixing them: scheduling, vendor relationships, booking inter-island flights for drivers, managing the fleet. It was wearing her down and preventing the business from growing.

"The feedback I'm getting, and internal feedback from myself and the team, is: it's time to hire an operations person."

She's now running the search using the Cheetah vs. Cat interviewing framework for evaluating fit.

Both are cats, but they’re not equals.

A house cat is needy and risk-averse. It waits to be fed. It stays in its lane. It does just enough. A cheetah? It hunts. It adapts. It moves fast.

Your business will be built on one of these two types of people. Hire house cats, and you’ll spend your life managing them. Hire cheetahs, and you’ll build something that can scale beyond you.

With the ops manager hire nearly closed, her time will shift toward what comes next: continued growth on the B2B cruise model that changed the trajectory of the business.

LOOKING BACK

Tania’s fleet manager once told her she had a lot of grit. She didn't disagree.

"I just kept going. Whatever happens, happens. Tomorrow's another day."

She doesn't stop to reflect on how far she's come nearly enough, she'll admit.

"I do not step back enough. But it's always a great thing to look back and see how far you've come. I've come very far, and the business has come very far.”

"The Boardroom is great because not only do we have access to the amazing team of advisors, but also the community of other business owners and the wealth of information, knowledge, and experience that they all bring to help with these things."

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