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Shay Brown and Cassie Torrecillas on building a business with your best friend

Podcast episode 75

Running a business with your BFF can be a dream come true, but it also comes with a unique set of challenges. In this episode, I sit down with Shay Brown and Cassie Torrecillas, best friends turned co-founders of Bucketlist Bombshells.

They share their incredible journeys, how they navigate friendship and business, and how they’ve turned their passion for travel into a thriving business venture.

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From friends to business partners

Eleven years ago, Cassie and Shay serendipitously met at a coffee shop in Mexico. They had both recently graduated from college and booked one-way tickets to Mexico with dreams of starting their own businesses instead of working for someone else.

During the first few years of their friendship, Shay and Cassie each started their own businesses and would collaborate on projects together. They also began traveling together while they built their businesses, and met other digital nomads along the way. 

They met several women who wanted to work online and travel but weren’t interested in affiliate marketing. They wanted to do something that felt purposeful and used their skills instead. 

Shay and Cassie launched a Facebook group called Bucketlist Bombshells to help teach people they met how to build online businesses while they traveled the world. From there, they decided to launch online courses, which officially launched their business together. 

Navigating friendship and business

The secret to building a business with your best friend is being able to have tough conversations. Cassie and Shay frequently talk about their vision for their company, what would happen if they ever wanted to sell it, their values, how they protect themselves, and more.

Over the years, they’ve also worked on their communication, which has helped build trust between them. 

Another thing that makes their partnership work is the fact that they have opposite strengths and can support each other’s weaknesses. However, they share similar values and a long-term vision for their business. They realized that they could go further together than they could on their own.

Defining their roles has also helped them work side by side and take advantage of their individual strengths. Reading the book Rocket Fuel by Gino Wickman helped them conclude that Shay should be the COO of the business and Cassie should be the CEO. 

The importance of shared values

Any time you go into business with someone, whether or not they’re your best friend, it’s crucial that you have shared values. As your business grows, your vision can change and pivot throughout different seasons. Your products and services may change over the years as well. However, your values should stay the same.

For example, Shay and Cassie share the value of supporting women in the online entrepreneur space. 

Your values are the north star of your business, so everything will be much smoother when you share values with your partner. It’s also helpful to have similar goals for your personal lives as well since your business is supposed to support the life you want to live. 

We have very opposite strengths and we support each other’s weaknesses, but together we are like superfire. We like to do opposite things, but we have similar values and we have a shared vision. All of those things coming together led us to recognize like, ‘hey, like we could go further together.’ Cassie Torrecillas
– Cassie Torrecillas

Lifting each other up in difficult seasons

Every business owner experiences a moment when they want to throw in the towel, and it happens in partnerships too. However, the great thing about having a partner is that they can encourage you when you are ready to quit. Cassie and Shay often experience an ebb and flow in this regard: when one of them is ready to give up, the other can be the encourager, and vice versa. 

Cassie and Shay have a helpful tip that they share with clients for navigating low seasons. When you are in survival mode, you do not have to try to get your business to thrive. Instead, you simply need to get to a neutral place. Getting back to neutral will help you remember your vision and gain energy, which will then propel you back to thriving. 

It’s common for business owners to experience simultaneous low seasons in their businesses and their lives. When this happens to Cassie or Shay, they give each other grace and support each other. 

How pivoting your services can reignite your passion for your business

For several years, Cassie and Shay sold courses that taught women how to launch online businesses. However, the online space underwent significant shifts during the pandemic, and Cassie and Shay realized that they needed to pivot how they served their community. People became more familiar with remote work, and online entrepreneurship, and were overwhelmed by courses teaching them get-rich-quick schemes.

Cassie and Shay wanted to service their clients in a deeper way, so they shifted to one-on-one coaching, group masterminds, and in-person retreats. Instead of solely teaching women how to start businesses, they taught them how to scale their businesses to six figures. 

Changing their business model took two years, but it reignited both of their passions for the work. Experimenting with different offerings has been creatively freeing for both of them, especially since they both consider themselves to be recovering perfectionists. Instead of being led by the next milestone to hit, they are now led by what sounds fun and what will serve their clients in the best way. 

The biggest differentiator between the businesses that succeed and the ones that fail

Cassie and Shay believe that the biggest differentiator between the businesses that succeed and the ones that fail is resilience. You have to allow yourself to fail and use your failures as data so that you can get back up and get it right. 

The joy of entrepreneurship is the journey, which is why you need to learn to enjoy the highs and the lows. Each experience is an opportunity to learn, experiment, and grow. 

Important sections of the conversation

  • [1:51] From friends to business partners
  • [19:48] Navigating friendship and business
  • [24:26] The importance of shared values
  • [28:39] Lifting each other up during difficult seasons
  • [38:35] How pivoting your services can reignite your passion for your business
  • [57:20] The biggest differentiator between the businesses that succeed and the ones that fail

Resources mentioned

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