Today's Guest

Jackie Reses is a fintech entrepreneur, former Head of Square Capital, and Chairman of the Economic Development Council for the Federal Reserve. Lauren Weinberg is the Chief Marketing Officer of Square, where she leads global Marketing and Communications. Lauren and Jackie are the co-authors of SELF-MADE BOSS: Advice, Hacks, And Lessons from Small Business Owners, a fascinating book that provides first-hand accounts of small business owners who have built their companies from the ground up.

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Episode Summary

Jackie and Lauren worked together at Yahoo and later at Square, where they spent a lot of time talking to small business owners. During the pandemic, they started discussing how during an economic downturn, a lot of people generally start their own businesses, and wouldn’t it be great if they could package together what they had learned working with small businesses. This idea was what led to the authors researching and writing Self-Made Boss.

But both Jackie and Lauren had significant backgrounds in small business long before they conceived of writing this book. Jackie relates in this episode how when she was growing up, her parents and grandparents owned small businesses and she started her own small businesses in high school and then college. After college, Jackie transitioned to Wall Street and spent time creating financial products and working on mergers and acquisitions. She then moved into technology, first at Yahoo and then at Square, and then she left to start her own business once again. While at Square she was involved in the lending and banking aspect. One of the most emotional parts of the journey for a small business owner is when they receive credit or capital to fund their business. Those stories that Jackie and Lauren heard working with small business owners inspired them to write Self-Made Boss.

The ideal reader for the book is anyone who is thinking about or currently running a small business. The book is designed as part starter-kit, part encyclopedia. Each chapter covers a specific area of running a business that the entrepreneur may need to learn or brush up on, such as Creating a Business Plan, Legal Matters, Brand Building and Marketing, Hiring and HR, and Growth and Scale. But each chapter is also sprinkled with real-life stories of fascinating entrepreneurs whose tales will resonate with small business owners and inspire them to continue on their journey.

The authors know from experience that it can feel lonely running your own business and Self-Made Boss aims to show small business owners that they are not alone and that many of the challenges they face are shared by other entrepreneurs. Through the book, they package together insights and lessons on how to overcome these challenges. Listen to Jackie and Lauren in this entertaining and fascinating discussion and you will undoubtedly want to read Self-Made Boss.

Resources Shared

• Self-Made Boss by Jackie Reses and Lauren Weinberg
• SelfMadeBoss.com
• Thryv
  

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