SelfMade Boss: Advice, Hacks, and Lessons from Small Business Owners

Part starter-kit, part encyclopedia, and part inspiration, Self-Made Boss is an essential survival guide for small businesses

When it comes to getting practical advice, small business owners too often don’t know where to look. Sure, you can find all sorts of high-level strategic tips from Fortune 500 CEOs. But what if you own a restaurant, and you’re trying to figure out how to source good fish, or if you’re looking to increase revenue from your plumbing supply store? You’ll be running a lot of Google searches before you hear from someone who’s actually stood in your shoes.

Longtime Square executives Jackie Reses and Lauren Weinberg want to change this. So they reached out across the country, talking to dozens of entrepreneurs with valuable businesses―and invaluable advice. This book is the product of that research. Part starter-kit, part encyclopedia, part inspiration, Self-Made Boss is filled with information not just about who these small business owners are, but how they built their companies, step by step.

How did they get their start? When did they decide to hire more staff? How did they set a course for growth? And when problems arose, how did they fight through them? You’ll hear from a second-generation ice cream shop owner on how to manage price increases; an oyster farmer finding new ways to stay afloat in the middle of a global pandemic; a roofer who refused to be denied or defined by her race and gender―and dozens of other small business owners making a big difference in their communities.

No matter the size of your business today―or where you’re thinking about taking the jump tomorrow―you’ll find answers you can apply right away.

Because there’s a common purpose that all small business owners share: the drive to build something from the ground up; the relentless pursuit of turning obstacles into opportunities and roadblocks into stepping stones. It’s tough and messy, hard-fought and hard-won. And above all, it’s something you can’t have when you work anywhere else―or for anyone else.

That’s what it means to be a Self-Made Boss.

About the Author

Jackie Reses is the Chief Executive Officer of Luna Financial Group, a fintech building banking-related financial infrastructure for tech and crypto companies and the Chair of the Economic Advisory Council of the Federal Reserve Bank of San Francisco. Previously, she was the Executive Chairman of Square Financial Services, Capital Lead and Head of the People Team at Square Inc. (Block Inc). She has been named one of Forbes "Self Made Women," Fast Company’s “Most Creative People in Business,” and American Banker's “Most Powerful Woman in Finance." Prior, she had leadership positions at Yahoo! and was a Partner at Apax Partners Worldwide, one of the largest private equity firms in the world. Jackie is also on the board of directors of Endeavor, Affirm and Nubank.

Lauren Weinberg is the Chief Marketing Officer of Square, where she leads global Marketing and Communications for the $100B company that provides business solutions for millions of small business owners all over the world. She has been named on Forbes “CMO Next,” Brand Innovators “Top Women in Marketing,” and Fintech Hub’s “30 Most Influential Fintech Marketers.” Prior, she held leadership roles at Yahoo, MTV, and AOL. She is an AdWeek Executive Mentor and advises early stage startups.

About the Author

Jackie Reses is the Chief Executive Officer of Luna Financial Group, a fintech building banking-related financial infrastructure for tech and crypto companies and the Chair of the Economic Advisory Council of the Federal Reserve Bank of San Francisco. Previously, she was the Executive Chairman of Square Financial Services, Capital Lead and Head of the People Team at Square Inc. (Block Inc). She has been named one of Forbes "Self Made Women," Fast Company’s “Most Creative People in Business,” and American Banker's “Most Powerful Woman in Finance." Prior, she had leadership positions at Yahoo! and was a Partner at Apax Partners Worldwide, one of the largest private equity firms in the world. Jackie is also on the board of directors of Endeavor, Affirm and Nubank.

Lauren Weinberg is the Chief Marketing Officer of Square, where she leads global Marketing and Communications for the $100B company that provides business solutions for millions of small business owners all over the world. She has been named on Forbes “CMO Next,” Brand Innovators “Top Women in Marketing,” and Fintech Hub’s “30 Most Influential Fintech Marketers.” Prior, she held leadership roles at Yahoo, MTV, and AOL. She is an AdWeek Executive Mentor and advises early stage startups.