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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 - Navigating Artificial Intelligence In The Workplace

Lioness Radio Show Special Episode: Navigating AI 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
Zanele Njapha, a transformational business leadership coach
Zanele Njapha, a transformational business leadership coach
Mekdes Mesfin, a proudly Ethiopian fashion designer and manufacturer
Mekdes Mesfin, a proudly Ethiopian fashion designer and manufacturer
Emilia Chisango, a multi-faceted business empire builder
Emilia Chisango, a multi-faceted business empire builder
Morongwe Mokone, a passionate champion of artisanal homeware
Morongwe Mokone, a passionate champion of artisanal homeware
Tshego Molefi, a pioneer transforming the waste management industry
Tshego Molefi, a pioneer transforming the waste management industry

IMAGE OF THE DAY. CELEBRATING WOMAN MADE IN AFRICA.

Image of the Day / Adèle Dejak

Big bold accessories…We are big fans of luxury jewellery and accessories made with love and passion on the African continent, and Adèle Dejak in Kenya is the epitome of handmade luxury. The brand c
Image of the Day / ReelFruit
 
Healthy snack treats…We love showcasing Africa’s women agribusiness builders, and ReelFruit, founded by Affiong Williams, is inspirational - it’s the largest fruit processing, packaging and distributi
Image of the Day / Dokmai Rwanda

Made in Rwanda Handbag…A passion for handcrafted accessories, combined with a sense of pride for ‘Made in Rwanda’ products, inspired Dokmai Rwanda founder, Bernadette Umunyana, to create a company
Image of the Day / Eki Silk

Silk Serenity…Nothing is quite as luxurious as silk, that’s why we love the ‘Africa on Silk’ collections from Eki, founded by Hazel Eki Osunde. Her latest Deep Dive Collection is inspired by the p
Image of the Day / The Nanjala Company

Pot plants delivered… Give gifts that will last, such as these stunning plants in individual pots from The Nanjala Company in Kenya, founded by Teresa Nanjala Lubano. This online store creates customized
Image of the Day / Sari for Change

Sustainable Sari Glamour - If you want to wear a robe that makes you feel and look glamorous, then Rayana Edwards, founder of Harem in South Africa, has a range of fabulous robes all made from sari fabrics. She has
Image of the Day / MonChoco

Pure chocolate heaven…If you are a chocolate lover, then you need to experience raw chocolate at its finest, and Dana Mroueh, founder of MonChoco an artisan chocolatier in Côte d’Ivoire, has just what y
Image of the Day / Mulandi Brindes

Say it with flowers…If you want to make someone feel special, then there is no better way than with the gift of fresh flowers, and Mulandi Brindes in Mozambique, founded by Vanessa Guilherme Nhabete, creates
Image of the Day / Mariée Eventos

The Wedding Planner…Every big celebration day needs great organization, and that’s where Iris Lezi Munguambe, founder of Mariée Eventos in Mozambique, is your go-to person. She launched he
Image of the Day / Dounia Home

Statement lighting… from Dounia Home, the home of innovative, handcrafted and ethically made Moroccan lighting and home decor founded by Dounia Tamri-Loeper. Her company designs, produces and brings to market hi
Image of the Day / Adèle Dejak

Big bold accessories…We are big fans of luxury jewellery and accessories made with love and passion on the African continent, and Adèle Dejak in Kenya is the epitome of handmade luxury. The brand c Image of the Day / ReelFruit
 
Healthy snack treats…We love showcasing Africa’s women agribusiness builders, and ReelFruit, founded by Affiong Williams, is inspirational - it’s the largest fruit processing, packaging and distributi Image of the Day / Dokmai Rwanda

Made in Rwanda Handbag…A passion for handcrafted accessories, combined with a sense of pride for ‘Made in Rwanda’ products, inspired Dokmai Rwanda founder, Bernadette Umunyana, to create a company Image of the Day / Eki Silk

Silk Serenity…Nothing is quite as luxurious as silk, that’s why we love the ‘Africa on Silk’ collections from Eki, founded by Hazel Eki Osunde. Her latest Deep Dive Collection is inspired by the p Image of the Day / The Nanjala Company

Pot plants delivered… Give gifts that will last, such as these stunning plants in individual pots from The Nanjala Company in Kenya, founded by Teresa Nanjala Lubano. This online store creates customized Image of the Day / Sari for Change

Sustainable Sari Glamour - If you want to wear a robe that makes you feel and look glamorous, then Rayana Edwards, founder of Harem in South Africa, has a range of fabulous robes all made from sari fabrics. She has Image of the Day / MonChoco

Pure chocolate heaven…If you are a chocolate lover, then you need to experience raw chocolate at its finest, and Dana Mroueh, founder of MonChoco an artisan chocolatier in Côte d’Ivoire, has just what y Image of the Day / Mulandi Brindes

Say it with flowers…If you want to make someone feel special, then there is no better way than with the gift of fresh flowers, and Mulandi Brindes in Mozambique, founded by Vanessa Guilherme Nhabete, creates Image of the Day / Mariée Eventos

The Wedding Planner…Every big celebration day needs great organization, and that’s where Iris Lezi Munguambe, founder of Mariée Eventos in Mozambique, is your go-to person. She launched he Image of the Day / Dounia Home

Statement lighting… from Dounia Home, the home of innovative, handcrafted and ethically made Moroccan lighting and home decor founded by Dounia Tamri-Loeper. Her company designs, produces and brings to market hi

STARTUP STORIES. MEET THE WOMEN WHO’VE LAUNCHED.

Featured
Suné Theisinger and Dr Juanri Jonck, two dynamic players in the aesthetic industry in South Africa
Suné Theisinger and Dr Juanri Jonck, two dynamic players in the aesthetic industry in South Africa
Tania Kabeya, a passionate chef and entrepreneur building a uniquely African culinary brand
Tania Kabeya, a passionate chef and entrepreneur building a uniquely African culinary brand
Aasiyah Adams, a visionary South African tech founder helping individuals and organisations to thrive in the digital economy
Aasiyah Adams, a visionary South African tech founder helping individuals and organisations to thrive in the digital economy
Komeshni Patrick, a tech legal consultancy founder empowering forward-thinking tech businesses to grow
Komeshni Patrick, a tech legal consultancy founder empowering forward-thinking tech businesses to grow
Lebo Biko, a South African champion of women-led innovation in Africa’s agri-food value chain
Lebo Biko, a South African champion of women-led innovation in Africa’s agri-food value chain

LIONESS DATA & INSIGHTS


LIONESS PLAYBOOKS



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