This Side Hustle Spotlight Q&A features Cathryn Lavery, founder of BestSelf Co.a planner and conversation card deck company that sold $45 million in product before being acquired in 2022. Answers have been edited for length and clarity.
Image Credit: Courtesy of BestSelf Co. Cathryn Lavery.
When did you move to New York City, and what inspired you to start your work? side hustle there?
I moved to New York City in 2011 for an architecture internship. In 2012, I was offered a full-time position, but at the last minute salary cut and the late start date left me in a precarious financial situation. With less than $800 to my name in a town where I knew basically no one, I needed to act fast to start a side hustle. Plus, as an Irish immigrant, I could only legally work for that company because they were sponsoring my visa, so finding a temporary job was off the table.
My first side hustle I used my design skills from architecture. I dabbled in graphic design, logo creation, and even learned how to format Kindle books. I took on any design-related job I could find—building websites, formatting books, or creating graphics. If you needed something done, I would figure out how to make it happen.
This experience opened my eyes to the possibilities beyond traditional employment and set the stage for my entrepreneurial journey.
How did you develop the productivity journal you listed on Shopify?
The idea for Self Journal came from a personal need. After realizing I had ADHD later in life, I struggled with it staying organized. I created the journal by combining frames from various personal development books I would read and putting them in. It was designed to help manage me productivity challenge, but I quickly realized that it could benefit others as well.
Interestingly, my history of architecture played a crucial role. In school, I designed a yearbook that taught me layout and layout design—skills that proved invaluable in creating the journal. like Steve Jobs said, “You can't connect the dots looking forward; you can only connect them looking back.”
People often ask if I regret studying architecture as it seems unrelated to what I'm doing now. But the truth is that I often find myself using the skills I learned during my studies. This experience taught me that skills are compounded over time, and the more diverse your skill set, the better equipped you are for different challenges.
When I first ventured into entrepreneurship, I thought my lack of formal business education would be a huge disadvantage. However, I soon understood business skills can be learned through reading and practice. Meanwhile, my design skills gave me a significant advantage, allowing me to take action and move faster than colleagues who needed to be hired.
This journey has reinforced my belief that no knowledge or skill is ever wasted. Each new skill you acquire adds to your toolkit, often in unexpected ways. For aspiring entrepreneurs, I would encourage embracing different experiences and skills – you never know how they might combine to give you a unique advantage in the future.
How did the business continue to take off from there? What roles did Daymond John and Tony Robbins play?
of Kickstarter The campaign for Self Journal was pivotal, raising over $326,000 and bringing BestSelf Co. to life. Our rapid growth saw us win the Shopify Build a Business Award a year after launch, which opened doors to incredible opportunities.
At the awards ceremony, I had the chance to meet Daymond John. During a game of Monopoly, he recognized my strategic skills, which led him to become an affiliate of our products. This endorsement from a “Shark” was an important boost for our brand.
I have a relationship with Tony Robbins, however, it goes much deeper. I had been an admirer of Tony's work and attended many of his events even before starting BestSelf. Our paths crossed again at the Build a Business Award, where he spent a day mentoring the winners. As our company continued to grow, we achieved something unprecedented – winning the Build a Business and Build a Bigger Business award a year later as we grew over 300% in one year.
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The Build a Bigger Business Award led to an incredible experience: flying to Fiji, staying at Tony's private resort and receiving personal mentoring from him. This time with Tony was transformative for both me and the business. He helped me understand that we needed to focus not only on loving our product, but also on loving our customers.
This change in perspective led me to think more broadly about how we can serve our audience. What other problems could we solve for them? How can we expand beyond our initial magazine offering? Tony's mentoring it was important to make me think more and consider our current business model and future directions.
Why did you decide to sell the company in 2022?
After seven intense years of building BestSelf Co., I reached a point where I needed a break. The industry had evolved significantly and my personal life had changed – I was married with a 6 month old.
Previous years had been particularly challenging, with a business partner split, acquisition issues, supply chain disruptions and Covid obstacle. Selling the company in October 2022 allowed me to take some money off the table and recharge. At that time, I thought I was ready for a new chapter in my life.
You bought the company back. How did this happen?
In mid-December 2023, the CEO of the company that bought BestSelf approached me about buying it back. of private capital the firm was facing financial difficulties – its promised investment had not materialized and it was winding down operations.
At first I was hesitant. Most of my original team had left after their retention bonuses expired. However, as I explored the options, I realized I had a unique advantage negotiations. I could take over without a transition period, which was crucial given the skeleton crew running the business.
The deal we negotiated was very favorable. like Warren Buffett said, “Danger comes from not knowing what you are doing.” With my years of experience with the brand, this felt like a low-risk, high-potential opportunity. It was a chance to apply new skills I had developed in coding, AI and automation to a real business scenario.
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What are some of the most valuable lessons you've learned on this journey? side hustle for full time business?
This trip has been a masterclass in entrepreneurship, teaching me the importance of sustainability and ELIGIBILITYnegotiation, continuous learning, solving problems and balancing ambition with well-being. And these lessons shape the way I run the company now. I am focused on creating a more sustainable and sustainable business model, using new technologies and approaching challenges with new perspectives. I'm excited to prove that I can do things even better this time.