Ep 259 | Cathryn Lavery

Written By Yasmin Nouri

How Testing Out Countless Side Hustles Helped This Founder Go From Being Broke to Building an 8-Figure Business

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Cathryn Lavery is the founder of BestSelf Co., a productivity tool-based business that sells journals, planners and conversation decks to help people achieve their goals and be their best selves. 

Cathryn moved to New York City from Ireland with only $758 and after the challenges she faced in her role as an architect and not making a livable wage, she was forced to find other means of income on the side. Despite having 7 years under her belt she realized this line of work was not the path for her. She eventually decided to go off on her own and transformed herself into an 8-figure founder. 

Going back to the early days, her side hustle eventually grew into something much bigger and that’s when Cathryn launched her Kickstarter campaign in 2015 to crowdfund her first product. BestSelf Co. sold $45 million in products before getting acquired in 2022, but recently Cathryn repurchased back her company to do things differently. 

In this week’s episode, Cathryn walks us through how she was forced into entrepreneurship because of necessity when she received a massive pay cut and the steps she took to figure things out when it was the most challenging for her. Cathryn dives into the details of how the idea for BestSelf was born, what she did to build up her confidence to take the leap, the early days of the business, and how she and her team managed to raise over $300,000 on her Kickstarter campaign with the goal only being $15k. We talk about her top productivity tips and lifestyle hacks that can help all of us be our best selves. She tells us about steps to take to make sure you’re finding the right business partner, why she decided to repurchase her company after 2 years of it being acquired, what it’s like to juggle being a new mom and founder, and so much more. 

Show Notes:

  • The "100 Days of Doing Challenge" and how it changed Cathryn’s life. [02:59]

  • How Cathryn balances being a high achiever yet exploring the uncomfortable. [04:47]

  • The benefits of entering the industry without prior knowledge. [07:12]

  • Cathryn’s childhood and upbringing. [08:15]

  • Where Cathryn got her self-confidence in taking the leap. [11:34]

  • Moving to New York, Cathryn’s internship experience, and getting her first job. [15:27]

  • Working as an architect while having a side hustle. [19:04]

  • The preparations Cathryn did before taking the entrepreneurial leap. [20:01]

  • Books that have been impactful for Cathryn. [22:26]

  • Shifts Cathryn discovered in her own productivity system and structure. [24:02]

  • How Cathryn deals with emotional aspects in life. [27:00]

  • Importance of structure and managing one’s energy. [29:22]

  • Starting BestSelf Co. as a side hustle and how it flourished. [32:31]

  • What resonated with BestSelf Co.’s product. [35:00]

  • Key takeaways that can improve daily productivity. [36:01]

  • Cathryn’s biggest lessons from having a business partner. [40:02]

  • Selling the business and buying it back from a private equity firm. [47:04]

  • Doing things differently for the business and enjoying the journey. [52:25]

  • Cathryn’s perspective on team productivity and outcomes. [54:47]

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Ep 258 | Nicole Bendayan