Rebuilding After Setbacks: An Entrepreneur Journey

I joined Jake and Gino to talk about building a multi-million dollar travel business from a side hustle, surviving COVID, and scaling through team building.

How did I get my start in the travel industry?

I was a high school English teacher running our school's travel club, and my husband's aunt, who owned her own agency, saw what I was doing with students and told me I could sell that same kind of travel to people who could actually afford it. I spent my summers learning the ropes from her.

What happened to my business when COVID hit?

It collapsed completely, right after I'd just had my son. I made almost nothing that year and went back to teaching temporarily to keep our family afloat, holding onto the belief that travel would eventually come back.

What was the turning point that got my business back on track?

A FAM trip to Cabo in 2021 changed everything. I realized I needed to build my own personal brand instead of relying entirely on my agency's identity, so I built my own website and started attracting the kind of clients I actually wanted.

Why did I build a team instead of continuing to do everything myself?

Revenge travel hit so hard after COVID that I became the bottleneck in my own business. I had to learn to say no to the trip types that weren't my strength and bring in people whose superpowers covered those gaps, which is what actually let me scale.

What's my advice for someone thinking about starting their own business?

Be willing to put in the unglamorous work for little to no payoff in the beginning. I made pennies an hour for years before this became sustainable, and staying relentless through that season is what separates the people who make it from the people who give up.

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Rebuilding a Travel Business From Scratch With Ali Raymer: Surviving and Thriving After COVID

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