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 it was acquired in 2022. Responses 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 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 a last-minute salary reduction and delayed start date left me in a precarious financial situation. With less than $800 to my name in a city where I knew basically no one, I needed to act fast on starting a side hustle. Plus, as an Irish immigrant, I could only legally work for that company because they were sponsoring my visa, so getting a temporary job was off the table.
My first side hustle leveraged my design skills from architecture. I dove into graphic design, logo creation and even learned Kindle book formatting. I took on any design-related work I could find — building websites, formatting books or creating graphics. If you needed something done, I would figure it out how to get it done.
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 the Self Journal stemmed from a personal need. After realizing I had ADHD later in life, I struggled with staying organized. I created the journal by combining frameworks from various personal development books I’d read and putting my own spin on them. It was designed to help manage my own productivity challenges, but I soon realized it could benefit others too.
Interestingly, my architecture background played a crucial role. In school, I designed an annual book that taught me typesetting and layout design — skills that proved invaluable in creating the journal. 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 since it seems unrelated to what I’m doing now. But the truth is, I frequently find myself using skills I learned during my studies. This experience taught me that skills combine over time, and the more diverse your skill set, the better equipped you are for various challenges.
When I first ventured into entrepreneurship, I thought my lack of formal business education would be a huge disadvantage. However, I quickly realized that 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 peers who needed to hire out.
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’d encourage embracing diverse experiences and skills — you never know how they might combine to give you a unique edge in the future.
How did the business continue to take off from there? What roles did Daymond John and Tony Robbins play?
The Kickstarter campaign for the Self Journal was pivotal, raising over $326,000 and giving birth to BestSelf Co. Our rapid growth led to us winning the Shopify Build a Business Award a year after we launched, which opened doors to incredible opportunities.
At the award event, I had the chance to meet Daymond John. During a game of Monopoly, he recognized my strategic skills, which led to him becoming an affiliate for our products. This endorsement from a “Shark” was a significant boost for our brand.
I have a connection with Tony Robbins, however, that 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 both the Build a Business and Build a Bigger Business Award a year later as we scaled over 300% in a year.
Related: How Tony Robbins Overcame His 5 Biggest Setbacks
The Build a Bigger Business Award led to an incredible experience: flying to Fiji, staying at Tony’s private resort and receiving personal mentorship from him. This time with Tony was transformative for both me and the business. He helped me realize that we needed to focus not just on loving our product, but on 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 offering of journals? Tony’s mentorship was instrumental in pushing me to think bigger and to consider both 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 baby.
The preceding years had been particularly challenging, with a business partner breakup, embezzlement issues, supply chain disruptions and Covid hurdles. Selling the company in October 2022 allowed me to take some money off the table and recharge. At the time, I thought I was ready for a new chapter in my life.
You bought the company back. How did that happen?
In mid-December 2023, the CEO of the company that bought BestSelf approached me about buying it back. The private equity firm was facing financial difficulties — its promised investment hadn’t materialized, and it was shutting down operations.
Initially, I was hesitant. Most of my original team had left after their retention bonuses expired. However, as I explored options, I realized I had a unique advantage in negotiations. I could take over seamlessly without a transition period, which was crucial given the skeleton crew running the business.
The deal we negotiated was incredibly favorable. As Warren Buffett said, “Risk comes from not knowing what you’re doing.” With my years of experience with the brand, this felt like a low-risk opportunity with high potential. It was a chance to apply new skills I’d been developing in coding, AI and automation to a real business scenario.
Related: I Negotiated With Warren Buffett and Here’s the One Thing the Oracle of Omaha Cared About
What are some of the most valuable lessons you’ve learned over the course of this journey from side hustle to full-time business?
This journey has been a masterclass in entrepreneurship, teaching me the importance of resilience and adaptability, negotiation, continuous learning, problem-solving and balancing ambition with well-being. And these lessons shape how I run the company now. I’m focused on creating a more sustainable and supportable business model, leveraging new technologies and approaching challenges with fresh perspectives. I’m excited to prove that I can do things even better this time around.
