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Self-Made Boss: Advice, Hacks, and Lessons from Small Business Owners by Jackie Reses & Lauren Weinberg

April 3, 2022 Melanie Hawken

Book Review

When it comes to getting practical advice, small business owners too often don’t know where to look, but Longtime Square executives Jackie Reses and Lauren Weinberg, authors of the book Self-Made Boss: Advice, Hacks, and Lessons from Small Business Owners, want to change all that. Part starter-kit, part encyclopedia, and part inspiration, Self-Made Boss is an essential survival guide for small businesses. 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, authors of the book Self-Made Boss: Advice, Hacks, and Lessons from Small Business Owners, 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. 

Author Quotes

Many entrepreneurs start their companies for the same reason…they see a problem in the world and decide to become part of the solution.

Throughout this book, you’ll hear from entrepreneurs who took a leap of faith to start a company…in every instance, they had an idea they were excited about and a plan to bring it to life.

No matter what kind of business they’re in, or why they started it, all small business owners have a common struggle. They’re all working to figure out how to best take an idea and turn it into reality - and make a living while they’re at it.

About the authors

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.


Why LoA loves it…

We know that small businesses are the backbone of the economy, but we also know it’s a hard journey for many women entrepreneurs who are launching their businesses to get the right support and guidance in those early days. Usually, some of the best advice comes from those who have been there and done it before, felt the start-up pain, and have the experience to know how to learn the right lessons for next time. So Jackie and Lauren in their new book, Self-Made Boss, have brought together some of those personal experiences of small business owners who have built their companies from the ground up. This is a great book that feels like having a team of experienced business building cheerleaders on your side. — Melanie Hawke, founder & ceo, Lionesses Africa

In Essential Tags Books
← Aurora Matavel, an award-winning Mozambican entrepreneur building a successful eco-cleaning businessGwendolyn Mahuma-Madida, a visionary in South Africa’s infrastructure sector  →

CELEBRATING 10 YEARS


LATEST PODCAST

LIONESSES OF AFRICA · AI Series Ep. 2 : AI-Human Collaboration in the Workplace

Lioness Radio Show: AI Series Ep. 2 : AI-Human Collaboration in the Workplace - Tune in for an engaging conversation designed to equip you with the knowledge to embrace AI and unlock its possibilities for your business.


LIONESS WEEKENDER COVER STORIES

LIONESS WEEKENDER COVER STORY
Retang Phaahla, a pioneer for South Africa’s indigenous teas
Retang Phaahla, a pioneer for South Africa’s indigenous teas
Dr Margaret Kemigisha, a publishing entrepreneur passionate about childrens’ literacy
Dr Margaret Kemigisha, a publishing entrepreneur passionate about childrens’ literacy
Sydelle Willow Smith, a pioneer of solar-powered mobile cinema in Africa
Sydelle Willow Smith, a pioneer of solar-powered mobile cinema in Africa
Babette Kourelos, a passionate artisanal bread-baking business builder
Babette Kourelos, a passionate artisanal bread-baking business builder
Thandekile Moloko, an entrepreneur empowering her clients’ financial futures
Thandekile Moloko, an entrepreneur empowering her clients’ financial futures

IMAGE OF THE DAY. CELEBRATING WOMAN MADE IN AFRICA.

Image of the Day / Midunu Chocolates

Chocolate love…We are big chocolate lovers at Lionesses of Africa, so we love these beautiful looking and fabulous tasting chocolates from Midunu Chocolates in Ghana, handcrafted by entrepreneur and chocol
Image of the Day / Adele’s Mohair

Mohair magic….Lovers of fine mohair will adore these beautiful, luxury yarns, courtesy of Adele’s Mohair, founded by Adele Cutten in the Eastern Cape of South Africa. She has built a highly succes
Image of the Day / Kwesh

Relaxed style…We love these stylish yet relaxed Kwanza pants and matching tops from Juliana Nasasira, the Ugandan fashion designer and founder of Kwesh. Juliana launched Kwesh in 2012, a fashion brand focused on creat
Image of the Day / Dvyn Treat Batamba’s

Premium Coffee Experience…We love a great cup of coffee in a morning at Lionesses of Africa, and so we are fans of Dvyn Treat Batamba’s great coffee brand in Mozambique, co-founded by Emilia
Image of the Day / Eloli

African luxury couture…For those who want to stand out from the crowd, Dibo Ndumbe Eyoh, co-founder and co-creative Director of Eloli, an award-winning luxury African fashion brand in Cameroon, has just what you need.
Image of the Day / Happy Coffee

Happy Coffee Experiences…If you are a fan of great coffee you will love Happy Coffee, founded by Princess Adeyinka Tekenah in Nigeria. She is a Coffee Entrepreneur and a Mom, and the founder of this growing ind
Image of the Day / Yococo

Vegan ice-cream heaven…If you are ice cream lovers like we are here at Lionesses of Africa, you will love the vegan ice cream from Yococo in South Africa, created by the talented Sinenhlanhla Ndlela. She is proving t
Image of the Day / The Joinery

Mini Box Tote…We have always been big fans of The Joinery, the sustainable and ethical product design brand based in South Africa founded by Natalie and Kim Ellis, and their exciting Future Tex™ fabric con
Image of the Day / Margaux Wong

Sustainable statement jewellery…We love the strong designs of the hugely talented Margaux Rusita, founder of Margaux Wong in Burundi. This international, multi-cultural jewellery and accessories brand was found
Image of the Day / Nokware Skincare

Sustainable skincare…We love to see natural cosmetics companies with a sustainable approach to business succeeding in Africa, and Nokware Skincare, founded by Tutuwa Ahwoi in Ghana is a great example. She f
Image of the Day / Midunu Chocolates

Chocolate love…We are big chocolate lovers at Lionesses of Africa, so we love these beautiful looking and fabulous tasting chocolates from Midunu Chocolates in Ghana, handcrafted by entrepreneur and chocol Image of the Day / Adele’s Mohair

Mohair magic….Lovers of fine mohair will adore these beautiful, luxury yarns, courtesy of Adele’s Mohair, founded by Adele Cutten in the Eastern Cape of South Africa. She has built a highly succes Image of the Day / Kwesh

Relaxed style…We love these stylish yet relaxed Kwanza pants and matching tops from Juliana Nasasira, the Ugandan fashion designer and founder of Kwesh. Juliana launched Kwesh in 2012, a fashion brand focused on creat Image of the Day / Dvyn Treat Batamba’s

Premium Coffee Experience…We love a great cup of coffee in a morning at Lionesses of Africa, and so we are fans of Dvyn Treat Batamba’s great coffee brand in Mozambique, co-founded by Emilia Image of the Day / Eloli

African luxury couture…For those who want to stand out from the crowd, Dibo Ndumbe Eyoh, co-founder and co-creative Director of Eloli, an award-winning luxury African fashion brand in Cameroon, has just what you need. Image of the Day / Happy Coffee

Happy Coffee Experiences…If you are a fan of great coffee you will love Happy Coffee, founded by Princess Adeyinka Tekenah in Nigeria. She is a Coffee Entrepreneur and a Mom, and the founder of this growing ind Image of the Day / Yococo

Vegan ice-cream heaven…If you are ice cream lovers like we are here at Lionesses of Africa, you will love the vegan ice cream from Yococo in South Africa, created by the talented Sinenhlanhla Ndlela. She is proving t Image of the Day / The Joinery

Mini Box Tote…We have always been big fans of The Joinery, the sustainable and ethical product design brand based in South Africa founded by Natalie and Kim Ellis, and their exciting Future Tex™ fabric con Image of the Day / Margaux Wong

Sustainable statement jewellery…We love the strong designs of the hugely talented Margaux Rusita, founder of Margaux Wong in Burundi. This international, multi-cultural jewellery and accessories brand was found Image of the Day / Nokware Skincare

Sustainable skincare…We love to see natural cosmetics companies with a sustainable approach to business succeeding in Africa, and Nokware Skincare, founded by Tutuwa Ahwoi in Ghana is a great example. She f

STARTUP STORIES. MEET THE WOMEN WHO’VE LAUNCHED.

Featured
Gladys Kgorane, an entrepreneur creating special events and wellness retreats for those looking for rest and relaxation
Gladys Kgorane, an entrepreneur creating special events and wellness retreats for those looking for rest and relaxation
Drienie Botes, an entrepreneur empowering women to achieve economic independence through beekeeping
Drienie Botes, an entrepreneur empowering women to achieve economic independence through beekeeping
Tumelo Tshwagong, a South African agri-entrepreneur contributing to finding sustainable local solutions to addressing food insecurity
Tumelo Tshwagong, a South African agri-entrepreneur contributing to finding sustainable local solutions to addressing food insecurity
Gloria Sellwane Phala, a South African entrepreneur helping clients benefit from the transformative impact of yoga
Gloria Sellwane Phala, a South African entrepreneur helping clients benefit from the transformative impact of yoga
Nondumiso Leshaba, a South African business builder providing professional business advisory and accounting services to SMEs
Nondumiso Leshaba, a South African business builder providing professional business advisory and accounting services to SMEs

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LIONESS PLAYBOOKS



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