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In this Side Hustle Spotlight Q&A, BestSelf Co., Ltd.is a planner and conversation card deck company that sold $45 million in products before being acquired in 2022. Answers have been edited for length and clarity.
Image courtesy of BestSelf Co. via Cathryn Lavery.
When did you move to New York and what made you decide to start a side business there?
I moved to New York City in 2011 for an architecture internship. I was offered a full-time position in 2012, but a last-minute pay cut and postponed start date left me in a financially precarious situation. In a city where I barely knew anyone and with less than $800 in assets, I needed to act fast to start a side hustle. Additionally, as an Irish immigrant, I could only legally work for a company that sponsored my visa, making temp work impossible to come by.
My first side hustle was leveraging the design skills I had developed in architecture. I dove into graphic design, logo creation, and even learned Kindle book formatting. I took on any design job I could get, whether it was building websites, formatting books, or creating graphics. If something needed doing, I would figure out how to get it done.
This experience opened my eyes to possibilities beyond traditional employment and inspired me to embark on my entrepreneurial journey.
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How did you develop the Productivity Journal that you posted on Shopify?
The idea for the Self Journal was born out of personal need. Later in life, after I discovered I had ADHD, I struggled to stay organized. I created this journal by combining frameworks from various self-help books I’d read and adding my own twist to it. I initially designed it to help me manage my own productivity challenges, but quickly realized it could be useful to others too.
Interestingly, my background in architecture played a key role. At school, I designed yearbooks and learned typesetting and layout design, skills that were extremely helpful in creating the journal. As Steve Jobs said, “You can’t connect the dots looking forward, you can only connect the dots looking backwards.”
People often ask me if I regret studying architecture because it seems unrelated to what I do now. But the truth is, I use the skills I learned during my studies a lot. This experience taught me that skills combine over time and the more diverse your skill set is, the better you’ll be able to handle different challenges.
When I first started my company, I thought that not having a formal business education would be a big disadvantage, but I quickly realized that business skills can be acquired through reading and doing, while my design skills were a big advantage, allowing me to move faster and take action than my peers who had to outsource.
This journey has further strengthened my belief that knowledge and skills are never wasted. Every new skill you acquire adds to your toolkit, often in unexpected ways. I encourage aspiring entrepreneurs to embrace diverse experiences and skills. You never know how they may combine to give you a unique advantage in the future.
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How did the business grow from there? What role did Daymond John and Tony Robbins play?
Self Journal’s Kickstarter campaign was pivotal, raising over $326,000 and thus was born: BestSelf Co. Rapid growth led to the company winning a Shopify Build a Business Award a year after launching, opening the door to amazing opportunities.
At the awards ceremony, I had the opportunity to meet Daymond John. During a game of Monopoly, he recognized my strategic skills and that led him to become an affiliate for our products. This endorsement from a “Shark” was a big boost for our brand.
But my connection with Tony Robbins goes much deeper. I had admired Tony’s work and attended many of his events even before I started BestSelf. We met again at the Build a Business Awards, where he spent a day mentoring the winners. Our company continued to grow and achieve unprecedented results. A year later we won both the Build a Business Award and the Build a Bigger Business Award, and we had grown over 300% in one year.
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The Build a Bigger Business Award gave me an amazing experience. I flew to Fiji, stayed at Tony’s private resort and received personal mentorship from him. This time with Tony was a turning point for me and my business. He helped me realize that I need to focus not only on loving my product, but also on loving my customers.
This shift in perspective forced me to think more broadly about how we could serve our readers. What other problems could we solve for them? How could we expand beyond the journal we initially offered? Tony’s mentorship played a huge role in helping me think bigger and consider both our current business model and our future direction.
Why did you decide to sell your company in 2022?
After spending seven years building BestSelf Co., I needed a break. The industry had evolved a lot and my personal life had changed too: I got married and had a 6-month-old baby.
The past few years have been particularly challenging, with a breakup with a business partner, embezzlement issues, supply chain disruptions, and the hurdles of the COVID pandemic. Selling my company in October 2022 allowed me to secure some capital and recharge. At the time, I thought I was ready for a new chapter in my life.
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You bought the company back. How did that happen?
In mid-December 2023, the CEO of the company that had acquired BestSelf approached me about a buyback. The private equity firm was experiencing financial difficulties, had not delivered on its promised investment, and had ceased operations.
I was hesitant at first because most of my former team members had left when their retention bonuses expired. But as I explored my options, I realized I had a unique negotiating advantage: I could take over seamlessly with no transition period, which was crucial in running a business with skeleton staff.
The deal we negotiated was incredibly favorable. As Warren Buffett said, “The only risk is not knowing what you’re doing.” With my years of experience with the brand, I felt this was low risk, high potential. It was a chance to apply my new skills in coding, AI, and automation to a real business scenario.
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What is the most valuable lesson you’ve learned on your journey from side hustle to full-time business?
This journey has been a master class in entrepreneurship, teaching me the importance of resilience and adaptability, negotiation, continuous learning, problem-solving, and balancing ambition and happiness. And these lessons have shaped how I run my company now. I’m focused on creating a more sustainable and supportable business model, leveraging new technologies, and approaching challenges with a fresh perspective. I’m excited to prove that we can do things even better this time around.
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