This episode of Side Hustle Spotlight features Cathryn Lavery, founding father of BestSelf Co.a company that makes planners and conversation card decks that sold $45 million value of products before being acquired in 2022. Answers have been edited for length and clarity.
Photo credit: Courtesy of BestSelf Co. Cathryn Lavery.
When did you progress to New York and what inspired you to start your side hustle there?
I moved to New York City in 2011 for an architectural internship. In 2012, I used to be offered a full-time position, but a last-minute pay cut and delayed start date put me in a tough financial situation. With lower than $800 to my name in a city where I knew almost no one, I had to act quickly and start earning extra cash. Plus, as an Irish immigrant, I used to be only legally allowed to work for the company because they sponsored my visa, so temporary work was out of the query.
My first side job used my design skills from architecture. I dabbled in graphic design, logo design, and even taught myself how to format Kindle books. I took on any design job I could find—building web sites, formatting books, creating graphics. If something needed doing, I discovered how to do it.
This experience opened my eyes to opportunities beyond traditional employment and set the stage for my entrepreneurial journey.
How did you create the productivity journal that you just hosted on Shopify?
The idea for Self Journal got here from a personal need. After realizing later in life that I had ADHD, I had trouble staying organized. I created the journal by combining frameworks from various self-development books I had read and adding my very own twist. It was designed to help me deal with my very own productivity challenges, but I quickly realized that it may very well be useful for others as well.
Interestingly, my architectural training played a key role. In school, I designed a yearbook that taught me layout and layout—skills that proved invaluable in creating a magazine. As Steve Jobs said, “You can’t connect the dots looking forward; you can only connect them looking backward.”
People often ask if I regret studying architecture because it seems unrelated to what I do now. But the truth is that I often use the skills I learned during my studies. This experience taught me that skills compound over time, and the more diverse your skill set, the higher prepared you are for different challenges.
When I first got into entrepreneurship, I believed my lack of formal business education could be a huge drawback. However, I quickly realized that business skills will be acquired through reading and practice. Meanwhile, my design skills gave me a significant advantage, allowing me to take motion and move faster than peers who had to hire someone.
This journey has reinforced my belief that no knowledge or skill is ever wasted. Every latest skill you acquire adds to your toolbox, often in unexpected ways. For aspiring entrepreneurs, I might encourage embracing a number of experiences and skills—you never know how they could mix to offer you a unique advantage in the future.
How did the business proceed to develop? What roles did Daymond John and Tony Robbins play?
The Kickstarter campaign for Self Journal was pivotal, raising over $326,000 and launching BestSelf Co. Our rapid growth led to us winning the Shopify Build a Business Award a yr after launch, which opened the door to incredible opportunities.
At the awards ceremony, I had the opportunity to meet Daymond John. He appreciated my strategic skills during a game of Monopoly, which led him to develop into a partner of our products. This endorsement from “Shark” was a significant boost for our brand.
But I have a connection with Tony Robbins that goes much deeper. I used to be a fan of Tony’s work and attended many of his events before I founded BestSelf. Our paths crossed again at the Build a Business Award, where he spent a day mentoring the winners. As our business continued to grow, we achieved something unprecedented—a yr later we won each the Build a Business and Build a Bigger Business Awards because we grew over 300% in a single yr.
The Build a Bigger Business Award was an incredible experience: flying to Fiji, staying at Tony’s private resort, and receiving one-on-one mentoring from him. That time with Tony was transformational for me and the company. He helped me understand that we’d like to focus not only on loving our product, but also loving our customers.
This shift in perspective prompted me to think more broadly about how we could serve our audience. What other problems could we solve for them? How could we expand beyond our initial magazine offering? Tony’s mentorship was instrumental in pushing me to think more broadly and consider each our current business model and future directions.
Why did you select 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 modified—I used to be married and had a 6-month-old baby.
The previous years were particularly difficult, due to a business partner breakup, fraud issues, supply chain disruptions, and Covid-related obstacles. Selling the business in October 2022 allowed me to save some money and regain my strength. At the time, I believed I used to be ready for a latest chapter in my life.
You bought the company. How did that occur?
In mid-December 2023, the CEO of the company that bought BestSelf approached me about buying it back. The private equity firm was struggling financially—the promised investment had fallen through, and the company was closing down.
I used to be initially hesitant. Most of my original team had left after their retention bonuses expired. But as I considered my options, I noticed I had a unique advantage in the negotiations. I could transition easily without a transition period, which was key given the skeleton crew running the company.
The deal we negotiated was incredibly good. As Warren Buffett says, “The only risk is not knowing what you’re doing.” Given my years of experience with the brand, this gave the look of a low-risk, high-potential opportunity. It was a likelihood to apply the latest skills I used to be developing in coding, AI, and automation to a real-world business scenario.
What are the most precious lessons you have learned on this journey from side hustle to full-time business?
This journey has been a masterclass in entrepreneurship for me, teaching me the importance of resilience and adaptation, negotiation, continuous learning, problem-solving and balancing ambition with well-being. And these lessons shape the way I run my business now. I’m focused on creating a more sustainable and supported business model, embracing latest technologies and approaching challenges with fresh perspectives. I’m excited to prove that this time I can do things even higher.
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