As the CMO for Square, Lauren Weinberg spends a lot of her time talking to new and inexperienced small business owners — and she knows that each of them has wisdom that the others could benefit from. So, Lauren and her former colleague Jackie Reses wrote a book pooling all that wisdom into one place, Self-Made Boss: Advice, Hacks, and Lessons From Small Business Owners
In this episode, Lauren and Joubin discuss why Lauren never leaves home without sneakers post-9/11; how she maintains discipline in her schedule, and how her priorities have changed over the years; how Lauren overcame three back-to-back challenges in her personal life; why she took a job at Square — after initially turning them down; and the importance of competition for any business.
In this episode, we cover:
- Weekend date nights and the best restaurants in New York City (10:04)
- How Lauren creates her own time and recharges (15:15)
- Moving to California to work at Yahoo, and finding a new community (19:32)
- “The worst year of my life” and going into “survival mode” (22:52)
- The difference between Square and its newly re-christened parent company, Block (30:22)
- Why our culture is galvanized by small business stories (36:05)
- What inspired Lauren and Jackie to write “Self-Made Boss,” and the surprising parts of publishing a book (39:52)
- Why Lauren includes sad or funny personal stories in every marketing email (42:26)
- Square’s secret superpower in the company’s early days (49:27)
- The planning “manifesto” Lauren sent to Square’s executive team shortly after joining (53:31)
- How Square “earns the right” to show up for social causes (56:50)
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