Grit

Guest: Lauren Weinberg, CMO and Global Head of Marketing and Communications at Square

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); and how Square “earns the right” to show up for social causes (56:50)

Show Notes

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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What is Grit?

Grit explores what it takes to create, build, and scale world-class organizations. It features weekly episodes highlighting the leaders who are pushing their companies to make a difference. This series is hosted by Joubin Mirzadegan, go to market operating partner at Kleiner Perkins, a venture capital firm investing in history-making founders.