Building A Business With Your Best Friend

1 2 Building A Business With Your Best Friend

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Kristen and Megan first bonded over their love of travel and shared study abroad experiences. Now, more than 10 years later, they are not just best friends but business partners. In 2016 they founded Legit Trips,  a boutique tour operator specialising in group trips for 30-40 somethings.

The idea for the business came about on a beach in Belize, at the tail-end of a stressful trip with 18 of their friends. Knowing that the experience would have been much better if they had organised everything on behalf of everyone but also understanding the insane amount of work that would entail, Kristen and Megan came up with a plan: “we’re coming back here next year and people will pay us for it.”

Organic business growth

A year later, they were back in Belize with 30 people on a trip that they had planned. It was hugely successful, and soon friends of friends began asking if they could join the next one.  “We didn’t set out with this intention of running 30 trips a year,” Kristen laughs.

Though their guests in the first 3 years were almost exclusively people they knew, transitioning from planning trips for fun to running a tour business was still a huge learning curve. Megan and Kristen admit that they made lots of mistakes along the way, particularly in terms of pricing and added costs.

However, they never let their lack of experience or the fear of failure stop them. “When we want to do something, we go for it,” says Megan. And so, their little passion project evolved into a successful business.

What it’s like building a business with your best friend

When asked about their experience working together as co-owners of Legit Trips, Megan says, “everybody I talk to — female entrepreneurs who want to go do something. I’m like, get a partner you trust! Because doing everything yourself is exhausting.”

Not only do Kristen and Megan get along extremely well on a personal level, but they also have different strengths and roles in the business. Furthermore, they know they can rely on the other person to pick up the slack whenever required.

However, they also recognise that their partnership is seemingly rare in the business world. Kristen describes an interaction she had with a lawyer in which he strongly advised that one of them have a majority stake in the business in case they ever disagreed on something. But for Kristen and Megan, that was never an option. “We are in it together, 50 50, and I don’t think that will ever change,” says Kristen.

Investing in brand identity

One of the best decisions Kristen and Megan made at the start of their business was investing in their brand identity. Both their logo and website were professionally designed, and they paid a branding consultant to help develop their voice and tone, as well as a style guide.

“It was an investment early on that felt really expensive at the time, however we haven’t had to think about it since,” says Kristen. They still refer to the guides on a regular basis today.

Additionally, they paid video interns to create cool videos about the trips and themselves, which has massively helped them to attract the right types of customers.

More From This Episode

Want to know how they found their first tour guides? What advice they have for hiring staff? What marketing strategies they use to attract new clients? How do they choose which destinations to offer? How has their business evolved over the last 5 years? Tune in to learn more from Kristen and Megan of Legit Trips!


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kara blythe creative

Kara Myers


I’m a former tourism professional turned web designer and podcaster. Tune in each week as I interview inspirational women crushing it in the travel industry. 

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