SN 1 EP 2

Risk Taking

Feat. Chelsea Moore, co-founder and CEO of BOXFOX

Being a founder is all about taking risks. You may risk your financial stability, your lifestyle, or your career. Either way, you can’t build a business without taking risks. And sometimes, leaps of faith far outweigh calculated decision-making.

Chelsea decided that creating her own company instead of following a more traditional career path was a risk worth taking.

Chelsea Moore was born and raised in Los Angeles, where she attended UCLA. After graduating, Chelsea and her now co-founder Jenni Olivero moved to Venice Beach. That’s where the idea for BOXFOX, an online personalized gift box service, was born.

The duo spotted a gap in the lifestyle and service space for elevated and effortless gifting, and knew they had something to offer.

On this episode

Chelsea talks with Katie and Jenny about:

  • The audacity it takes to veer from a traditional career path
  • A moment that felt like an enormous risk
  • A decision she made that didn’t pan out as she expected

Top takeaways

Editor’s Note: We’ve edited and condensed the questions and answers slightly for clarity.

When you’re young and naïve, you can be oblivious to the potential ramifications of a major risk, like leaving the professional workforce. Sometimes that’s a blessing and other times it’s a curse. Tell us what it took for you to quit.

One night, I was in the production room of the ad agency I worked for. It was 3:00 a.m. and I was waiting for a creative team member to put their final blessing on something so I could hand it off to a courier to get on a flight. I realized I was doing this for a mattress brand and I thought, “What am I doing here? This is not going to be my life.”

It took Jenni [co-founder and COO] and Sabena [co-founder] over a year to quit their full-time jobs, but I felt like we couldn’t fail. I thought we had a great idea and we were the first to do it. We were convinced it was going to take off.

There was a lot of insecurity, too, because we came from a very successful group of friends—we’re close with doctors, lawyers, consultants. We’re all overachievers. They were going to these amazing schools and getting great jobs. And Jenny and I felt a little insecure.

You really have to be super vulnerable to want to start something of your own and be willing to ride that wave for a year and a half of getting it off the ground.

It’s this weird combination of having audacity and thinking that we can’t fail, and the vulnerability of understanding that we’re not doctors, but we think this is going to work. It was an interesting time. If I was later in my career, I might have approached it differently.

What are some of the biggest risks you’ve taken along the way as your company has grown over the past seven years?

When we were first working out of my apartment, Jenny and I realized we needed to find a place with three bedrooms so we could have one bedroom dedicated to working on BOXFOX and two bedrooms for ourselves. We were annoying all of our other roommates with all the stock we had in our apartment.

We decided we would pay the rent for the third room through the income we were earning with BOXFOX, and that was the scariest financial moment. We realized we were signing this lease, saying that this one room was going to pay for itself. It was such a monumental moment for us—we were super nervous.

We then moved into an official warehouse a year and a half later. But every time we sign a retail or commercial lease, it’s been scary because we’re putting our personal credit guarantee on the line.

Now we’re at 15,000 square feet. This move in 2018 was one of the scariest things for me because it was a 5-year commitment and we didn’t have clarity on how we were going to grow within those five years.

Has there ever been a risk that you’ve taken where you’ve regretted the decision?

I wouldn’t say there’s ever anything we’ve regretted. I would say there are things we thought we should do that we wouldn’t do again.

For example, our business isn’t set up for resale within a big retailer. But being in a big retailer is such a mark of success for some consumer packaged goods (CPG) and direct-to-consumer (DTC) brands. You want the clout and the history and the legacy you get with big retailers.

But we found it doesn’t really move the needle for our business. And the work that goes into it is insane. We realized we prefer to focus on the existing customers we have.

There was a time when we went all out trying to get into a retailer and we learned that it really wasn’t something we needed to do. I wouldn’t say there’s anything we regret, but I’m glad we definitely know now that’s how we feel about retail.

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